That’s usually where things start slipping. The pitch gets stronger, the business underneath it gets harder to explain, and one simple question can give that away very quickly.

That’s why I asked Susan Montgomery to write this guest piece. She’s backed multiple companies that reached billion-dollar outcomes, writes the Angels and Unicorns newsletter, and has a new book coming out under the same name.

What she gets into here is one of the clearest investor tells I’ve read in a while. 👇🏻

The pitch is working 🔍 The business isn’t

The pitch was excellent. It had a tight narrative, a clear picture of the market, and the founder knew their fundraising history cold. He also had a decent answer on competition.

He was also wearing a Patagonia vest, which somehow felt on-brand for the whole thing. By the time the deck ended he’d said the word “momentum” five times. I remember because it’s one of the words I always keep a tally of when I’m being pitched.

I made one request. “Walk me through last month.”

The long pause was eventually followed by, “We’re seeing really strong traction across multiple channels and the market response has been very positive.” I stopped taking notes.

That’s not a business update, it’s a brand statement. I’ve heard a version of it in more first meetings than I care to count, usually from founders who’ve spent three months on the pitch narrative and about seven minutes on their numbers.

What I’m actually watching for

By the time I’ve agreed to meet you, I’m not really watching the deck. The deck is what got us in the room in the first place.

I’m watching for the gap between what you’re saying and what’s actually happening in the business. This is easier to spot when I’m tired and grumpy, which probably says something unflattering about late afternoon slots.

A deck is designed to close that gap. If it got us together, then it’s a good deck. You’ve worked hard on it. But the gap shows up in how you answer the question that wasn’t in the prep and that no deck ever covers.

So I make the same request in every first meeting. Not because I’m so smart, but because it works and I haven’t found anything better.

Walk me through last month

Founders who know their business can usually answer in under sixty seconds. They give me one number and what moved it, or one decision they made or didn’t.

Whether the number is good or bad is almost beside the point, which still surprises some people when I say it. What I’m looking for is operational clarity.

Founders who are running on narrative answer with narrative. Trends. Channel response. Market signals. Healthy pipeline. No number, no cause, no decision.

The longer the answer, the wider the gap. I’ve never had a founder answer like that and turn out to be running a tight business underneath it.

Maybe the exception exists somewhere. I’ve mostly stopped expecting it.

The thing I don’t know how to fix

Most founders in a fundraising process have spent more time on the pitch than on their operating data in the months leading up to it. I understand why. The pitch gets you in the room. Nobody schedules a meeting because your MRR tracking is clean.

But somewhere in the preparation, the pitch stops being a representation of the business and starts replacing it. The story becomes load-bearing and the founder starts knowing their TAM better than what happened last month.

The strange thing is that by the time they’re in front of me, they’re not exactly lying. They’ve just been in pitch mode long enough that the pitch feels like truth.

I don’t have a clean answer to this. The obvious one is “stay close to your numbers”, but founders raising a round are doing twelve things and the numbers rarely feel like the most urgent one.

What I can tell you is that the founders who stay in contact with their operating data during a raise are noticeably easier to talk to. The meeting just feels different, more relaxed and less performative.

If you’ve already closed a round

Don’t think this stops applying once you’ve raised. You’ll likely raise again.

The next round’s investors will be later stage, less patient with narrative, and quicker to spot the gap. What passes at seed doesn’t pass at Series A.

Not because Series A investors are smarter, but because they’ve sat through more of these meetings and the filter gets tighter with exposure.

Run the test on yourself now. What’s your answer? Pick last month. One number and what caused it. One decision you made as a result. Say it out loud. Time it. If you can’t do it cleanly in sixty seconds, it’s worth asking why before someone else does.

The pitch should be good. That part’s not wrong. It just shouldn’t be the thing you know best when you walk in.

👤 Susan Montgomery backed 13 unicorns at pre-seed and seed. In Angels and Unicorns, she writes about what investors are actually clocking in those first ten minutes, and why founders often miss it until it’s too late. Subscribe for a clearer view from the other side of the table.

Susan | Angel Investor

I backed 13 ‘unicorns’ at pre-seed and seed. Writing for angels who want better returns and for startup founders who want their attention.

Two more reads before your next investor pitch:

I’ve been there, and it’s frustrating.

That’s why I asked executive coach and adviser Kathy Wu Brady to write about how to get aligned with your team and clear confusion before it turns into culture.

Kathy is a 2x CEO and COO, writes the Lead Without Limits newsletter, and works with leaders on fixing themselves before they start trying to fix everyone else. 👇🏻

Where confusion starts

When teams start missing things or doing work twice, the problem often starts earlier than you think.

The instruction sounded clear enough in the room. But once the work got moving, it turned out not to be clear at all.

That’s because capable people still need to know what’s actually being asked of them.

You thought you were clear

If you are a leader, especially early in your career, there is a bias a lot of organisations push on you: sound more confident than you feel.

I got that advice in my mid-twenties, just after stepping into my first executive role at a large media company.

My boss told me I would be more effective if I answered questions with more confidence and fewer caveats. What I heard was simple: stop sounding uncertain.

When I pushed back and said, what if I don’t know the answer, what if I’m not sure, he said to come off as sure. That’s what people expect.

What happens next is harder to notice. You get used to sounding certain, and after a while you stop checking whether people understood what you meant in the way you thought they would.

That’s where the question starts to matter. Instead of asking yourself whether you said it clearly, ask what the other person actually heard.

The team fills in the gaps

This problem doesn’t stop with the leader. It moves through the team as well.

In some teams, people learn quite quickly that asking too many questions makes them look slow or unsure. After a while, they stop asking and just try to keep up.

That’s one of the biggest gaps inside a team. People start acting as if they should already know what the leader meant and move forward without needing much else.

Something else happens as well. People learn to talk about what is going fine and stay quiet about the rest. Anything messy, unclear, or unfinished gets left unsaid.

Over time, fear starts shaping what people say and what they hold back. The team gets less honest about what is not working, and problems stay untouched for longer than they should.

Where the damage shows up

This starts in a very ordinary way. Someone gives direction too quickly, assumes it was clear enough, and moves on.

I know because I was one of those leaders. My to-do list was so long it could not be done in a day, sometimes not even in a year.

In a startup environment, it can feel like the whole organisation is sitting on your shoulders. When that pressure builds, speed feels like the only sensible response because everyone is waiting on you.

That’s when the direction goes out too quickly and some of the detail gets lost.

The team feels the rush as much as they hear the words, so people stop looking for more context and move ahead with whatever they think they understood.

Then it spreads. One unclear conversation becomes several, and by the time it reaches vendors or partners, people are already working from different versions of the same expectation.

You start seeing work repeated, and people get frustrated with each other because they don’t realise they’re working on the same thing.

After a while, trust starts to go because nobody is completely sure what was meant to happen or who was meant to do it.

You don’t need a weak team for that to happen. It can happen with good people when the expectation was never as clear as everyone thought.

Most “clarifying” makes it worse

One of the biggest mistakes you can make at this point is deciding for yourself what needs clarifying instead of finding out what the other person actually took from it.

You can try to fix the problem by explaining more, but that does not always help.

Sometimes you answer the original question, add extra detail around it, and leave people more confused than they were to begin with.

Or you can say a lot more and still leave the real point untouched. What matters is whether you dealt with the part that had actually gone wrong.

That’s why the better question is not did I say it clearly? Ask what the other person actually heard.

The other mistake is treating clarification like another announcement. It works much better when it becomes a conversation.

Support is not control

Not everyone on your team needs the same level of oversight.

A newer team member who is still learning the role usually needs more check-ins. Someone experienced and motivated can work with much lighter ones.

I think about it as an 80/20 problem. For someone who needs more support, I might stay close to roughly 80% of the work in progress. For someone stronger and more self-directed, maybe 20%.

The numbers are not really the point. The point is that different people need different levels of support, and a lot of leaders forget that.

The next part gets missed a lot. Don’t just tell people when you will check in. Ask what helps them do the work well.

People don’t all need the same thing. One person may prefer to give updates in writing, while someone else works better by talking things through.

Someone learning something new might need a daily check-in for a while, and another person may find that amount of contact suffocating.

You don’t have to follow every preference, but it helps to understand what makes the work easier for each person to do well.

What will make a difference is building a way of working that gives people the support they actually need.

Silence is not alignment

When nobody has any questions, don’t assume that means things are clear. More often, people don’t feel safe enough to say what’s not making sense yet.

If everyone walks away from an important conversation saying “that was fine” or “sounds good,” and nobody has anything they want to push on, that should worry you.

A team that’s really thinking something through will want to test at least one part of it. They might ask what happens if this goes wrong, or whether something has been missed.

The same thing applies in one-to-ones. If you want the real answer, give people a heads-up that you want their honest read on something specific, and be clear about what you are asking. Then ask and pause.

It’s easy to rush in and fill the silence too quickly. Leave it there for a moment, and that’s usually when people say what they really think.

Start where the cost is highest

Start with one or two things, not ten.

Sit down and ask where the biggest gap is right now. You don’t need the full picture straight away. Focus on the area where unclear expectations are causing the most trouble or wasting the most time.

Write it down, be honest about what is not working, and then do the part most leaders resist by naming it openly with your team.

You don’t have to have it figured out. You can say: I’m not sure I’ve been setting clear enough expectations in this area. I want to do better, and I’d like to understand what you need.

That kind of honesty doesn’t weaken your authority. It gives people room to tell you what is actually getting in the way.

Then get specific about the gap. Are you clear on the outcome but vague on how people should get there? Or have you been clear on behaviour without explaining why it matters? Start there.

Build in one way of checking this and actually use it, starting with the area that matters most and the team closest to it.

Change shows up in the work first

You’ll feel the difference before you can measure it properly.

People start saying sooner when something is unclear, and problems get picked up before they have had time to spread.

That’s the first sign things are getting clearer. The team spends less time cleaning up confusion later because more of it gets dealt with properly at the start.

Lead without Limits

Find your path to meaning and success with the help of a 2x CEO & COO, executive coach, and artist who's been in the arena.

By Kathy Wu Brady

Kathy Wu Brady is an executive coach and adviser, a 2x CEO and 2x COO, and the writer behind Lead Without Limits. She has spent 20 years launching, scaling, and reshaping businesses across five industries, and now helps leaders make clearer decisions and lead with more courage. Connect with Kathy on LinkedIn.

If AI keeps giving you bland writing, obvious ideas, and work you still have to rescue, the problem usually is not the model.

You haven’t really trained it, briefed it, or given it enough context to do the job well. You’ve been throwing work at it and hoping for the best.

You wouldn’t onboard a human hire this way. AI is no different.

To get real value from it, you need to treat AI more like staff and take the time to train it properly. That’s the point Millennial Masters guests keep coming back to.

A better question is what a new hire would need to know in order to do this well. Ask it that way and the mistake becomes obvious. 👇🏻

You skipped the onboarding

Carly Meyers explained it in the clearest way I’ve heard: “Think of it like one person. Think of it like you’ve just hired someone.

“Say you just hired a sales and marketing person. They’ve walked into your office for the first time. You sit them down and say, right, this is what I want you to do.”

That’s the part most founders skip. They don’t explain the business properly or spell out who the customer is.

They also don’t show the AI what the brand sounds like, what counts as good work, what needs approval, or where it should stay in its lane.

They start with tasks, which is the same mistake people make with new hires when they are moving too fast. Things get messy quickly.

That’s not new. Strong hires still need context, and good employees take time to become useful. Throw someone into the middle of the business without proper onboarding and the work usually comes back half-baked.

Then AI gets treated as if none of that applies. The expectation is close to finished output on day one, and when it disappoints, the tool gets the blame.

This is a management problem

Damon Flowers was direct: “AI is like a staff member and it can do anything. It can do finances, it can do marketing, it can have a conversation with you and negotiate stuff.

“But you’ve got to be really good at training it around who it is, what’s the role, what context you’re giving it, and what do you specifically want it to go do for you.”

That’s the shift a lot of founders still haven’t made.

If AI is sitting inside your workflow like a member of staff, the output depends on the job you have given it and how clearly you have set it up.

If that setup is vague, the output usually comes back vague too. You get writing, research, strategy, and sales copy that could belong to almost anyone.

Jess Jensen made the same point: “I think of AI as almost like a junior employee. The more that I train and invest in that junior employee to get them to understand our strategy, our goals, our vision, who I am, the better the output’s going to be because now they’re really tracking with me.”

That’s a much better approach than treating AI like a one-shot tool. The quality improves when it starts following how you think and the standards you work to.

Open a fresh window, type a request, get something back, and judge the whole experience on that one exchange. Of course the output will disappoint.

There’s no real context, no memory worth using, no examples from previous work, and no proper explanation of how the business operates.

Ryan Carruthers described AI as “a marketing or copywriting assistant right now… like having a graduate, someone who’s just getting into it, who’s starting to learn the frameworks.”

That’s useful because it brings the expectation back down to earth. A graduate can help and save you time. They can also waste a lot of time if you expect them to understand the business from one instruction and a few scraps of documentation.

You’re expecting senior output from something you barely trained, then blaming the tool when it cannot deliver.

Give it a job first

Start by getting clear on the role. A lot of AI use is still far too broad.

If you ask it to be a strategist, researcher, editor, analyst, and operator all at once, it ends up being none of them properly. If you want better work, define exactly what role it is supposed to play in the business.

That might mean a copy assistant, a research analyst, a sales support function, a coding reviewer, or an editorial second pair of eyes. The more precise the role, the easier it becomes to train well.

Carly Meyers’ framing helps here. One “person” does one type of work. The AI is no longer guessing what it is there to do.

The practical test is simple. If a human joined your team tomorrow and got this exact brief, would they know what role they were in and what good looked like in that role? If the answer is no, the AI will struggle too.

Once the role is clear, context starts doing most of the heavy lifting. A lot of people cut corners here because giving context feels slower than prompting. Skip it and the quality usually falls apart.

Nick Holzherr described AI as “a distributed team member,” which is useful because anyone working outside the room needs clear documentation to do the job properly. Nobody expects remote employees to just pick all of that up on their own.

It has to be written down somewhere, with examples and enough detail for someone to understand how the company operates. AI is no different.

That’s why businesses with decent documentation and defined processes often get stronger results from AI sooner. The material needed to train it already exists.

If everything is still sitting in your own head, the output is usually worse because the AI is being asked to work inside a business that has never been clearly articulated.

Teach it what good looks like

You get weak output when you expect AI to pick up voice and standards from nothing. Give it a clear sense of how the business sounds at its best.

That means showing it strong examples of how you write, sell, and communicate, along with the kinds of phrasing or claims you do not want it using.

This matters because voice is not decoration. In a lot of businesses, it carries judgement. It tells you whether something feels salesy, technical, or generic. Leave that undefined and the model usually fills the gap with average internet sludge it’s been trained on.

Yota Trom uses AI as an editor rather than a creator, saying it helps her because she’s not a native speaker. That’s a useful boundary. It gives the AI a clear job and makes it easier to see what should still stay with the human.

The same thing applies to the goal of the task. If you ask for writing, research, summaries, or strategy thinking without explaining what the work is supposed to achieve, the AI has to guess what good looks like, and the output usually gets weaker.

When the task has a clear purpose, the output usually improves. AI is no different.

Constraints matter too. If it cannot make claims without sources, say that. If it should not sound too polished, say that. If it needs to protect margin, stay within brand language, or avoid legal overreach, make that clear as well.

You don’t need a perfect instruction sheet for every task. You need to stop expecting AI to know the business better than the person using it.

This is where it gets useful

Don’t ignore this part because it is less exciting than trying a new tool.

The quality improves when you start correcting the work and letting that shape the next round. That is how a useful working relationship develops, whether it is a junior hire or a custom GPT.

Jess Jensen’s point about investing in the junior employee matters here. It takes repetition, correction, and enough patience to build something better over time instead of opening a fresh session and starting the whole disappointment cycle again.

What looks like the model getting smarter is often just better management. That is where the gains stop being theoretical.

Once the system is trained properly, more first-pass work gets handled before a human steps in. Drafts come together faster, research is easier to pull together, and more of the admin-heavy work gets moved off people’s plates.

James Augustin thinks about AI automation as taking the admin-heavy parts of a role away so people can focus on the work they are actually good at and paid for.

Ryan Carruthers gave a similar example when he described building an AI that could handle after-hours sales work, gather the right information, and book calls so nobody on the human sales team had to keep carrying that burden late into the evening.

Damon Flowers sees it as getting work to 85 to 95% done before a person even touches it. That number will vary by task, but the principle is right.

At that point, you are reviewing and refining far more often than you are starting from scratch. That’s where the time starts coming back.

The real mistake you are making

AI is starting to expose which businesses are systemised and which still live mostly in the founder’s head.

Weak output comes from shoddy setup. The role is vague, the context is thin, the standards live in your head, and then the tool gets blamed for sounding half-baked.

You’re expecting too much from something you’ve barely trained.

That’s why this is more fixable than you think.

You don’t need a better model to get better results. You need to brief it clearly, train it properly, give it feedback, and hold the standard.

Do that and you’ll get more from AI than most people complaining about it ever will.

I first heard it mentioned in one of my early Millennial Masters interviews with Yehong Zhu, who referenced Nassim Taleb’s Antifragile in her book recommendations.

By then, I had already lived through years where stability disappeared.

The pandemic period, especially 2020 through 2022, was one of the hardest stretches I’ve had in business and in life.

I had seen the shocks, the uncertainty, and plans breaking down without having a useful language for it, let alone a framework for how to respond.

That is why John Brewton’s take stood out. When we spoke about antifragility and I read how he translated it into the day-to-day reality of running a company, I knew it would make a strong guest post for Millennial Masters.

His piece below turns antifragility into something far more useful than theory. It is the practical version of what founders can do when the old playbook stops working. 👇🏻

How you build for shocks

It is easy to get used to a stretch where demand is steady, costs are predictable, and suppliers pick up the phone.

That has not been the world for a while now. Tariffs shift, energy prices move, and supplier pricing changes without much warning.

A Harvard survey of more than 4,000 SMBs found that nearly half of owners misjudged how tariffs were affecting their costs.

That is not because small operators are careless. It is because the world around them is changing faster than most people can track while still trying to run a business day to day.

Last October, I published a detailed piece on Operating translating Nassim Taleb’s ideas on antifragility into business practice. The framework still holds up, but frameworks do not pay invoices.

This is the practical version. It is for the founder with 12 employees, one line of credit, and a Monday morning stand-up with very little patience for theory.

By antifragile, I mean a company that can take a shock and come out stronger on the other side. The goal is to build in a way that leaves you better placed when things move against you.

The 5 buffers that keep you in the game

Buffers are what keep a bad quarter from becoming a crisis.

If they are too thin, one shock can put you on the back foot. If they are strong enough, you have time to respond and, sometimes, enough room to take advantage.

1️⃣ Cash

How many weeks can you operate if revenue drops 30 percent tomorrow? Not based on a trailing twelve-month average, but on your actual weekly burn against your actual cash balance.

If the answer is less than eight weeks, that deserves your attention before almost anything else. When I was scaling R.G. Brewton from $27 million to north of $75 million in industrial distribution, the metric that gave us permission to be aggressive was knowing exactly how many weeks of runway we had.

2️⃣ Time

Slow decisions kill small companies faster than most bad decisions do. How many days does it take you to reprice a product, switch a supplier, or shut down a project that is bleeding money?

If the answer is weeks, you have a problem. Tariff policy changed eleven times in six months last year. The founders who got through it repriced in 48 hours. The ones who waited absorbed the margin hit.

3️⃣ Pipeline

If your top three clients represent more than 50% of revenue, your P&L can look steadier than it really is. It holds until one of them leaves, delays payment, or renegotiates terms.

Concentration risk is one of the most common buffer gaps I see in advisory work. It does not show up on a dashboard. It shows up on a Tuesday morning phone call.

4️⃣ Talent

Name every person in your company who is a single point of failure for a critical process. If that person gets sick, quits, or burns out, what breaks?

That is a structural weakness. Cross-train the role or document the process. Do that this month.

5️⃣ Suppliers

How many of your key inputs come from one source, one country, or one contract with no pre-vetted alternative?

In B2B distribution, we kept backup supplier relationships for every critical SKU category. Not because we assumed we would need them, but because if we did, there would be no time to start from scratch.

Small bets and fast feedback loops

Taleb’s barbell strategy is simple. Keep 80 to 90% of resources in proven work that pays the bills. Put 10 to 20% into small bets with real upside. The danger sits in the middle: the mid-budget initiative with medium conviction and no kill switch.

For a small company, a small bet is not something you talk about on a strategy retreat. It might be a landing page with $300 in ad spend behind a new offer, a pilot engagement with one client in a new vertical, or a price test on a single product line for two weeks.

What matters is that the hypothesis is written down before you spend the money, the downside is capped, and the timeline is short enough to read before the next move.

The kill rule matters more than the bet itself. Define what failure looks like before you start, not after sunk cost fallacy has you giving it another month. If a test cannot show signal within two to four weeks, it is either too slow or being measured badly.

Review active bets once a week. Spend fifteen minutes looking at what is still open, what should be killed, and what is showing enough signal to push harder.

Done properly, this is how small wins start to stack without small losses quietly piling up underneath them.

Guardrails to stop a bad month from spiralling

One bad month is manageable. The problem starts when a second bad month passes with no real response and a third is allowed to land on top of it. What matters most is how quickly you react.

This comes down to urgency, both yours and your team’s.

Three triggers should force a same-week decision:

• Cash drops below your minimum weeks-of-coverage threshold

• A top-three client signals churn or payment delay

• The cost of a key input spikes by more than 15% with no clear date for it to come back down

When one of those triggers fires, do not leave it hanging. Make the call that week. The response might be small. Reprice one line, pause one project, or call one client. What matters is that you move.

Run a subtraction audit once per quarter. List every recurring cost, meeting, subscription, and initiative, then cut the bottom 10 to 15%. This is not about being tidy. It is about reducing the number of places where a shock can hurt you.

Every unnecessary cost gives rising prices another place to squeeze margin. Every unnecessary meeting takes time away from fixing what matters when something breaks.

Before any commitment above a number that matters to your business, spend ten minutes writing down how it could fail and whether the structure of the bet protects you if it does. It is Taleb’s premortem at founder scale.

It takes ten minutes. It has saved me from more bad decisions than any financial model.

5 items. 10 minutes. Weekly.

That is the entire system. No single review will change much on its own. The value comes from doing it 52 weeks in a row.

The forecast is dead. Your business shouldn’t be.

You cannot run a company as if conditions will stay still long enough for the spreadsheet to catch up.

What matters more is whether the business can absorb pressure, respond quickly, and adjust when something changes.

This is practical, not theoretical. The founders who keep moving well under pressure are usually the ones who have already built for it.

👤 About John Brewton

John Brewton writes Operating, a bestselling Substack newsletter documenting the history and future of operating companies. He is a graduate of Harvard University and began his career as a PhD student in economics at the University of Chicago. After selling his family’s B2B industrial distribution company in 2021, he has spent the years since helping business owners, founders, and investors improve how they operate. He is the founder of 6A East Partners, a research and advisory firm focused on the future of companies. He still cringes at his early LinkedIn posts and loves making content every day, despite protests from his wife, Fabiola. Connect with John on LinkedIn.

Operating by John Brewton

Weekly Reporting on the History & Future of Operating Companies

More smart strategy from Millennial Masters:

I spent years watching startups burn through funding, trying to out-build incumbents, and I made the same mistake on products I worked on.

The teams that lasted focused on less.

That lesson is why I asked Mike Goitein to come back and break down how lean teams build competitive advantage.

In his last guest post, he broke down how to find gaps in a competitor’s strategy. This time, he walks through what to do once you find them. 👇🏻

The edge comes from precision

The trap most teams fall into with AI

Building an impressive demo is easier than ever with AI.

Competitors can spin up tools in a weekend that look great on the surface. But those screens rarely integrate with a customer’s existing setup, so they fall apart in real production.

Big competitors optimise for speed and broad appeal. Lean teams win by spotting small friction points those tools ignore and building around them.

AI design platform Magic Patterns reached $1M in ARR with no team. Co-founders Alexander Danilowicz and Teddy Ni built and scaled it on their own, managing to raise a $6M Series A.

Tools like v0, Bolt, and Lovable generate interfaces from prompts, but the output often feels generic and disconnected from the actual product.

Danilowicz and Ni came from front-end development, which shaped how they approached the problem.

They focused on design system integration, letting teams import their own components, so prototypes match the existing product from the start.

That focus created an advantage broad tools struggle to replicate without changing how they work.

How lean teams build moats

Saying no matters

Lean teams work within constraints, which forces focus.

Magic Patterns said no to customers who wanted backend support. They focused on product teams of 5–50 people working with existing design systems.

Each decision made the positioning clearer. Product teams with design systems created better expansion and retention than one-off project work.

A customer might start with a couple of licences and expand across the team as the product proves itself. You see the same pattern elsewhere.

In the AI meeting space, Granola made a similar decision. They ignored the mass transcription market and focused on C-level executives and VCs in sensitive meetings.

Both companies built multi-million-dollar businesses by committing to very specific customers, which shaped everything else they built.

Where the advantage actually comes from

Magic Patterns focused on understanding what product teams were trying to build and preserving that in the output.

The Chrome extension pulls structure from existing sites and reuses components so outputs match the product.

That keeps them strong in a specific part of front-end work where generic tools struggle.

Changing what each role can do

Speed doesn’t hold for long, so advantage comes from somewhere else.

Magic Patterns shifts what different roles can do inside a team. When Zeal’s CTO Pranab Krishnan started using it, he stopped writing long UX descriptions and began building interactive prototypes himself.

Engineers no longer wait on design handoffs, and they build with a clear sense of what can actually ship. Even product managers can lay out requirements visually. The product team can do more without adding new roles.

That kind of shift makes a tool hard to remove once a team adopts it. I break down the full strategy of Magic Patterns in more detail in Product Strategy Decoded.

The lean team’s competitive advantage audit

Here are three quick tests you can run on your product:

1️⃣ The rejection test

Who are you explicitly saying “no” to? If your product tries to serve very different customers at once, the focus disappears.

Pick the customer you understand best and build for them. Every customer you turn away sharpens how well you serve the ones you keep.

2️⃣ The workflow test

Does your product fit into how people already work? Magic Patterns integrated into the design systems teams already use.

AI tools that ignore existing context are easy to replace. The closer you are to real workflows, the harder it is to replace you.

3️⃣ The capability test

Are you only speeding things up, or changing who can do the work? Tools that only save time compete on shrinking margins.

Tools that let non-specialists contribute become part of how teams work. Does your product let new roles do work they couldn’t before?

The real advantage

Building advantage as a small team comes down to focus, not feature volume.

It comes from a clear understanding of the customer and helping them do things they couldn’t before.

Every market leader operates on a set of assumptions. Over time, those assumptions stop matching reality.

That’s where lean teams find their opening. They spot constraints larger competitors ignore and build for the customers who feel that gap most.

Start with one question: what are the biggest players in your market not set up to solve? That gap is where your advantage sits.

👤 About Mike Goitein

Mike is the author of Product Strategy Decoded, where he reverse-engineers the strategy of products, startups, and creators each week using a proven framework.

He’s a Certified Strategy Professional with more than 15 years of experience helping Fortune 200 companies and startups alike sharpen their choices and deliver measurable results. Connect with Mike on LinkedIn.

Product Strategy Decoded

Every week, I pull back the curtain and make strategy easier using a proven framework. You'll get insights of what works today and why, with powerful takeaways you can apply to your own business.

By Mike Goitein

Over the last two years I’ve lost a significant amount of weight using GLP-1 medications. They definitely work. The part nobody explains comes after.

I’ve tried all three of the big ones along the way: Ozempic, Wegovy and Mounjaro. I now stay on a small maintenance dose because the main thing people say about them is actually true.

Weight-loss injections quiet the constant thinking about eating. When that noise fades, a surprising amount of attention comes back to the work you actually care about. Anyone running a company knows how valuable that mental space can be.

The part people talk about less is what the process feels like while the weight is coming off. These drugs work by pushing your calorie intake down automatically.

When that happens your body runs on less fuel, which means energy can dip, mood can wobble a bit and exercise is usually the first thing that disappears from the week.

That’s usually the moment you realise the injection handles the appetite, while everything else still depends on you. You feel lighter on the scale while your body sometimes feels worse.

Another practical point is cost. Unless you have them prescribed, GLP-1s can become a serious monthly expense (up to £400). When you are spending that kind of money, it makes sense to think about how to get the best outcome from them instead of hoping the injection will solve everything on its own.

And sooner or later most people face the same question: what happens when you stop or reduce the dose, because the food noise returns and the habits underneath start running the show again.

That’s why I asked Tom Hutchinson-Smith about this.

Tom is a personal trainer I interviewed previously on Millennial Masters and he works mostly with founders and operators whose schedules look messy from the outside but still want their body to keep up with the demands of running a business.

I asked him to explain how GLP-1s actually fit into that reality and how training and nutrition keep the process from weakening the system underneath. 👇🏻

Why the injection suddenly makes sense

Founder life rarely supports neat routines around food.

The day fills with calls, travel, meetings and deadlines. Meals happen wherever they fit and hunger tends to appear at inconvenient moments.

Over time eating becomes something that constantly interrupts the day. GLP-1 medications change that environment quickly.

Hunger fades into the background and the urge to snack stops driving the schedule.

Meals shrink naturally and eating becomes something you do when needed rather than something you think about all day.

For someone already juggling a company that change feels like relief.

What the scale doesn’t show you

GLP-1 drugs make eating less much easier to maintain. That part works very well.

What they don’t do automatically is protect strength or muscle while bodyweight falls.

When calorie intake drops for months at a time the body adjusts. Muscle can shrink along with fat and strength in the gym slowly slips.

The scale continues moving in the direction people want, so this often goes unnoticed.

For founders that matters more than it might seem. Your body is the machine that carries long days, travel, pressure and constant decision making.

When strength fades the work feels heavier even though nothing in the calendar has changed.

The training that keeps your body intact

Tom’s advice to founders is deliberately simple because complicated plans rarely survive busy schedules.

Three strength sessions during the week keep muscle active while weight comes down. Each session fits inside an hour and focuses on movements that train large parts of the body at once.

The real focus is keeping the engine running properly while the rest of the business keeps moving.

When founders travel frequently Tom usually gives them a shorter hotel-gym version of the same routine so the habit doesn’t disappear during busy weeks.

Tom shared the exact framework he gives founders using GLP-1s. 👇🏻

Download The Lean Leader Program and use it as a practical guide.

What to eat when you barely feel hungry

When GLP-1s suppress appetite the amount of food drops quickly. That means the food you do eat needs to carry more of the workload.

Protein helps hold on to muscle during the weight loss phase. Vegetables help digestion and keep the body getting nutrients even when meals are smaller.

Dietary fat still matters for hormones and general health even though extremely heavy meals tend to feel uncomfortable on these medications.

Tom usually encourages founders to think less about strict dieting and more about building meals around protein and vegetables first.

This approach usually covers what the body needs without turning food into another project to manage.

The body that runs your business

GLP-1 medications are powerful tools and they genuinely help many people lose weight.

They remove the constant battle with appetite which used to make fat loss extremely difficult to sustain.

What they don’t replace is the physical foundation that keeps someone functioning well while running a business.

Strength training, regular movement and basic nutrition habits protect the body that supports your work. When those stay in place the weight loss process leaves someone lighter without leaving them weaker.

That outcome usually feels very different once the drug is no longer doing the work.

The number on the scale changes quickly. The condition of the body running the company matters far longer.

Discipline still decides the outcome

One part of the conversation that rarely gets mentioned is what happens if you stop taking the drugs.

From my own experience the food noise does not come back overnight, yet after about two weeks the difference becomes noticeable.

Hunger creeps back in, thoughts about snacks start appearing again, and that quiet mental space around food begins to shrink.

That is the reason I now stay on a very small maintenance dose. I do not always follow the seven-day schedule either. Sometimes it stretches to ten days, sometimes fourteen, usually depending on when I feel that background noise returning.

Keeping the result still comes down to discipline.

GLP-1 medications make the early stages of weight loss far easier to sustain, yet keeping the result afterwards depends on the habits that support your body when the drug is no longer doing the work.

If those habits disappear, the body gradually returns to old patterns.

The people who keep the result are usually the ones who built the habits while the drug was helping them.

Because once the noise returns, the discipline is yours.

Quick question for founders reading this:

If you’ve tried GLP-1 injections, what surprised you most about the experience?

I’m curious how others are navigating this.

More healthy stuff from Millennial Masters:

A guest post by Jenny Ouyang: I run Build to Launch, where 5,000+ builders learn to ship real products with AI. I’ve used AI to build and launch 10+ products, publish 100+ articles, and run an AI builder community. None of that happened because AI is magic. It happened because I learned to manage it.

The hire nobody trained you for

Most founders interact with AI the way they’d interact with Google: type something in, hope for the best, get frustrated when the output is mediocre.

That’s like hiring someone talented and never telling them what the company does.

AI is the teammate who never sleeps, has read everything on the internet, works at impossible speed, and has zero judgment about what actually matters to your business.

Left unmanaged, it produces confident-sounding work that misses the point entirely. Managed well, it becomes the most reliable operator on your team.

The shift isn’t technical, but managerial. And if you’ve ever onboarded a brilliant but unpredictable new hire, you already have the instincts for this.

Set direction before you set tasks

When a new team member joins, you don’t hand them a task on day one and expect perfect output. You give them context: what does the company do, what does quality look like here, what are the unspoken rules. AI needs the same onboarding.

In my workflow, I maintain what’s essentially an employee handbook for AI. It’s a document that spells out: who we are, what our voice sounds like, what standards we hold, what mistakes to avoid, and what “done well” looks like. Every single task the AI touches starts from that foundation.

When I skip this step (and I still do sometimes, because speed is tempting), the output is generic. It reads like it could’ve been written for anyone. The moment I set direction first, the output sounds like it came from someone who actually works here.

The management principle: Context before tasks. Always.

If you’re a founder delegating to AI for the first time, write down three things before you open any tool:

1. What does your company/brand actually sound like? (Not “professional.” Be specific. Conversational? Data-driven? Blunt?)

2. What are the non-negotiable standards? (Accuracy over speed? SEO matters? No jargon?)

3. What should AI never do on its own? (Publish without review? Make claims about customers? Touch financials?)

That document becomes your home truth. Write it once, and every interaction with AI improves from that point forward.

Give feedback, don’t start over

Here’s the pattern I see constantly: someone gives AI a task, gets a mediocre result, scraps it, and tries a completely new prompt from scratch.

That’s the equivalent of firing someone after their first draft.

The founders getting real value from AI treat bad output as a feedback opportunity. When the first result misses the mark, they tell it specifically what’s wrong.

Not: “This isn’t good, try again.”

Instead: “The tone is too formal for our audience. Make it conversational, like you’re explaining this to a smart friend over coffee. Also, the second section jumps to a conclusion without enough evidence. Add a specific example.”

That’s a performance review. And it works exactly the way it works with people: specific, actionable feedback produces better results than vague disapproval.

I routinely go three to five rounds of feedback on a single piece of work. Not because AI is bad at its job, but because good output is iterative.

The same is true when you’re managing humans. The difference is AI doesn’t get defensive, doesn’t take it personally, and can turn around revisions in seconds.

The management principle: Iterate, don’t restart. Your feedback is the most valuable input in the system.

Consistency from systems, not supervision

If you’ve ever managed a growing team, you know the moment when things start breaking: when the work depends on you being in the room.

The fix is always the same. You create systems: templates, checklists, standard operating procedures. AI works identically.

I run 15+ specialized AI configurations for different types of work: research, writing, code review, SEO, editing. Each one has its own “job description” with specific instructions, quality standards, and guardrails.

The research agent knows to cite sources. The editing agent knows our style guide. The code review agent knows our security standards.

This means I don’t re-explain the basics every time I start a task. The system holds the standards. I just point it at the work.

For founders and operators, this is the unlock. You don’t need 15 agents. Start with one reusable prompt template for the task you do most often:

• If you write weekly updates, create a template that includes your voice, your format, your typical structure.

• If you review proposals, create a checklist prompt that evaluates against your actual criteria.

• If you do market research, create a research brief that specifies what sources you trust and what depth you need.

Save it, reuse it, and refine it over time. That’s how you scale AI output without scaling your own involvement.

The management principle: Build systems once. Run them repeatedly. Improve them incrementally.

Know when to step in & when to let it run

The hardest management skill, with people or AI, is knowing when to get involved.

Here’s the decision framework I use, and it works the same way any experienced manager delegates:

Let it run when the cost of a mistake is low: internal notes, first drafts, brainstorming, data formatting, meeting summaries. If an error takes 2 minutes to fix, the review isn’t worth your time.

Review before it ships when the output is client-facing, public, or financially significant: proposals, published content, anything with numbers that someone will act on. AI is confident even when it’s wrong. Your job is to catch the difference.

Do it yourself when the task requires your specific judgment, relationships, or lived experience: strategic decisions, sensitive communications, anything where your reputation is on the line in a way that a quick fix can’t undo.

Most founders err in one of two directions. Some review everything, which defeats the purpose of having a fast teammate. Others review nothing, which eventually produces an expensive mistake they could’ve caught in 30 seconds.

The management principle: Delegate based on the cost of failure, not the difficulty of the task.

The job has changed, and that’s the opportunity

Here’s what I want to leave you with.

The founders getting disproportionate results from AI often realised that their role shifted. Their focus moved from doing the work themselves to defining what good work looks like and shaping how it gets done.

That’s a management role. It involves setting direction, giving feedback, building systems for consistency, and deciding where output can run with autonomy and where it needs closer review.

The tools will keep getting better and the models will keep improving. What compounds over time is your ability to manage the process and shape how the work flows. That skill carries forward as the systems evolve.

You’re developing a management capability that scales with each new AI system that ships.

If you’re reading this thinking you already know how to manage, that foundation still applies here. It simply needs to be directed at this layer of work.

Start here

Everything in this article came from doing this hands-on, not reading about it.

If the management mindset clicked for you and you want to see what it looks like in practice, I wrote a companion piece that walks through 12 projects in a deliberate progression: from a 10-minute build to a system that runs your content, research, and publishing without you touching it.

If you’re a founder or operator, skip straight to Tier 3. That’s where the management principles from this article become real infrastructure: a personal command center that encodes your best workflows, a research pipeline that runs autonomously, and a one-center ecosystem where you sit in one place and everything amplifies outward. That’s the part built for people who think in systems, not code.

And if you want this kind of thinking every week with practical AI systems, real examples, that’s what Build to Launch is. 5,000+ founders and builders getting the playbook for making AI actually work.

Build to Launch

Turn AI ideas into shipped products. Proven systems and showcase opportunities for builders who launch.

By Jenny Ouyang

Jenny Ouyang runs Build to Launch, a newsletter and community for builders shipping real products with AI. She’s built and launched 10+ products, published 100+ articles, and created the systems described in this piece, where AI operates as a managed team, not a magic wand. Subscribe to Build to Launch.

You set a direction and nothing openly challenges you, yet weeks later you realise the work has stalled and the idea has been deprioritised.

That kind of resistance can make you question whether you’re actually in control or whether people are simply managing you. If that sounds familiar, you’re not alone.

There’s a name for it: institutional no. It’s the slow, almost invisible way growing organisations block new ideas without openly rejecting them.

That’s why I asked the Strategy Shots newsletter to unpack it for Millennial Masters and show how to stop it before it hardens into culture.

Where ideas go to die

I came across the “institutional no” while reading about Amazon’s internal culture in Working Backwards. I recognised it immediately because it shows up in almost every company.

How ideas die in practice

It’s when a company says no to an idea without ever clearly saying no.

Imagine a scenario where a founder shares an idea with the team and they say they will think about it. Then nothing happens.

The founder follows up once or twice and hears that progress is being made.

A few small steps appear, but not enough to move it forward, and over time the idea fades without discussion or decision.

This is institutional no, resistance to change that hides behind activity.

Why it happens

Institutional no shows up from a few common sources.

Here are the ones I see most often in startups:

When failure isn’t safe

New ideas fail more often than they succeed.

If a founder has not created real psychological safety around failure, institutional no shows up early.

When blame is the first response to failure, people protect themselves instead of learning.

Experimentation is the core of strategy, and experiments are about trying, failing, learning and trying again.

This does not mean lack of accountability, but it’s more about how to hold people accountable.

That’s why you need to focus on safety and not on blame.

When people expect blame, they avoid exposure. Avoiding exposure means avoiding new bets.

Institutional no becomes permanent when middle managers are rewarded for stability instead of progress.

When agreement kills debate

Groupthink is when people want to be more agreeable with each other.

When a founder brings a new idea to the table, the loudest voice may quickly explain why it will not work.

Others often agree, sometimes out of habit, sometimes to avoid friction.

The idea fades before it receives the discussion it deserves.

How to avoid it?

• Don’t let the first voice set the direction.

• Make people write down their view before the meeting. You get better thinking and fewer passengers.

• If everyone agrees too quickly, be the devil’s advocate yourself.

  ---

When process becomes the answer

As a startup scales, processes multiply. They exist to reduce mistakes, but over time they can also reduce initiative.

Introducing strict and overreaching processes too early strengthens institutional no.

Pay attention when people frequently quote process as a reason not to act.

When “the process says no” replaces “does this move us forward?”, growth slows and no one owns it.

This is your sign to do one of two things:

• review the process to see if it is hindering innovation

• review the ask to see if you are indeed asking the wrong thing, time and again.

Why good ideas quietly die

Institutional no usually shows up as drift rather than open resistance, and that distinction matters. It’s because most founders read it as disloyalty when it is often avoidance, fear, or simple overload spreading through the system.

What to do to keep it in control:

• If something matters, assign a single owner.

• Give it a visible deadline.

• Require a written decision: yes, no, or not now.

Silence should never be a valid outcome.

Institutional no is expensive because it kills speed. Startups win on speed.

If ideas cannot be killed quickly or backed quickly, you are already behaving like a large company without the advantages of one.

Subscribe to Strategy Shots for more insights that move your business forward

Strategy Shots Digest

Bite sized strategy bits

🤜🤛 More teamwork from Millennial Masters

It’s easy to believe you can correct things later, once there’s more money or traction, yet the early choices decide who feels comfortable joining next.

When you’re a first-time founder, especially before a fundraise, you don’t fully see how much this shapes everything that follows.

Bringing in strong early hires is hard when money is tight and your name doesn’t yet carry weight.

The people who change the trajectory of a company tend to arrive through trust and reputation, and both of those are rare early on.

That’s why I asked Cris Cafiero to write this guest post. He advises investor-backed companies through his work with Sequoia, helping leadership teams make clearer decisions about hiring as they grow.

Cris also writes the Startup People Spend Substack, where he studies how early people decisions compound over time. 👇🏻

Hiring is a network effect

Five AI startups raised $20b+ with a combined valuation of $206b, all led by former Google employees:

• Anthropic – Dario Amodei was a senior research scientist at Google Brain

• Perplexity – Aravind Srinivas was a research intern at Google

• Mistral AI – Arthur Mensch spent three years at Google DeepMind

• Cohere – Aidan Gomez was a researcher at Google Brain

• Glean – Arvind Jain was an engineer at Google

Welcome to the ‘Google Mafia’. One respected alum starts a company and pulls in former colleagues, who then bring people they already trust. In this case, talent and capital moved together from Google.

I see it in Series A and B companies all the time. Founders raise from people they already know or who trust someone involved early. That backing often brings attention, introductions, and follow-on interest.

The more time I spend around early-stage teams, the clearer it becomes that recruiting success is shaped less by sourcing tactics and more by who shows up first.

Signals

When I ask founders how many early hires came from their own network, the answer is usually most of them.

They’re friends and former colleagues who didn’t hesitate when you told them you had seed funding, a big idea, and almost nothing built yet.

This is where trust starts. It spreads through referrals.

The strongest signal of how someone will perform is often who brought them in. Good people tend to recommend people like them.

There’s another part to this. Your startup sends signals long before anyone talks to you. People decide whether they want in based on what they see from the outside.

Four signals show up again and again: taste, velocity, capital, and values.

Before you have a brand, these signals do most of the work in hiring and early traction. Teams tend to lean harder on the ones they already have while the rest catch up.

Taste

The quality of your product and design pulls people in, especially those who care about craft. They notice it right away, even if they can’t explain why. It’s just good.

A reputation for good taste shows people what you care about. It comes through in the product, the code, the brand, and the details. People who take pride in their work tend to look for teams that do the same.

A few startups that show this well:

• Notion has a product that feels considered from end to end. The design is clear, the experience is calm, and the brand is consistent without trying too hard.

• Clay built something that people can pick up quickly and keep growing into. It has a strong point of view, and the visual choices feel deliberate rather than decorative.

Velocity

The buzz of rapid progress is contagious.

When the product and user base are visibly growing, that growth attracts and retains talent and capital.

Founders who show their progress make it clear how the company operates day to day. That clarity tends to attract builders who care about getting real work shipped.

Startups moving quickly (and publicly):

• Ramp are shipping features faster than anyone on the market, and they’re fundraising at breakneck speed, closing a $500m round 45 days after their previous.

• Perplexity AI is focused on rapid iteration and user-focused launches, posting regular “What We Shipped” posts to their changelog to highlight their pace. Imaginative, hypnotic brand aesthetic too.

Capital

It’s shorthand for credibility.

Funding from the right sources signals to candidates that someone else has already run diligence on you. It reduces personal risk and puts the company on more radars.

A well-known investor (a16z, Sequoia, etc.) or a hefty funding round announcement can pull in people who were not actively looking. It also makes introductions easier, across hiring, customers, and future fundraising.

Companies grabbing headlines with power raises:

• Rillet raised $70m Series B led by a16z and ICONIQ Capital after doubling ARR within just 12 weeks.

• Kalshi raised $165M from Paradigm & Sequoia to be the market for predictions & forecasting.

Values

The boundaries you set early shape how the company behaves day to day and what it stands for. It’s a powerful attractor for talent.

Vague slogans do not hold up here (“work hard, play hard” won’t cut it). Early hires need to live these values because people talk. The people who stay tend to share those standards.

Netflix’s “keeper test” is a clear example. It filters for high-performers who don’t tolerate mediocrity or even “brilliant jerks.” Outsiders judge it as intense or even unfair, but insiders love it.

Here are a couple companies with thoughtful, intentional company values:

• Zapier has been a remote-first organisation since before it was cool. I love how they tout their values in practice and with examples.

• Strava anchors its values in sport and community, which shows up in how it treats both users and employees.

A loop worth protecting

When a respected hire leaves, parts of their network often leave with them.

Future fundraising follows the same pattern. A poor investor choice can limit future funding options.

Protecting the integrity of your network is protecting the future of your team.

If you get it wrong, the loop works against you.

Cris Cafiero works with investor-backed companies at Sequoia, where he helps leadership teams think clearly about hiring, compensation, and people spend as they scale. He also writes the Startup People Spend Substack.

Startup People Spend

From capital to headcount: weekly people spend guidance for early-stage founders, investors, and operators.

By Cris Cafiero

Check out more of Cris Cafiero’s posts:

Startup People Spend

Golden Handcuffs: The Startup Equity Trap & How to Avoid It

Startup People Spend is a weekly newsletter where I share how the best startups manage compensation, benefits, and equity. To receive new posts and support my work, consider becoming a free or paid subscriber…

Read more

3 months ago · 24 likes · 9 comments · Cris Cafiero

Startup People Spend

The Guide to People Spend Strategy

At the end of the article, subscribers get access to the full People Spend Strategy Playbook, a 22 page report on…

Read more

8 months ago · 26 likes · 1 comment · Cris Cafiero

More people wisdom from Millennial Masters:

I’ve lived that version of it. The diary stays busy, the work keeps coming, and the margin still disappears once the real cost of delivery shows up.

That is why I asked Vanessa Ugatti to write this. She is a coach, speaker, and the author of True Worth, and she gets how often service founders mistake demand for a pricing model that actually works.

If you are booked out and still not feeling it in the numbers, this is the reset. 👇🏻

Why your prices keep you stuck

Underpricing usually starts as a shortcut to get a yes, then it becomes the rate you’re scared to move.

It changes the kind of clients you attract and the way you deliver. Scope creeps, clients push for more, and the margin disappears into extra work.

If that pattern feels familiar, pricing has turned into a comfort test rather than a decision you can defend.

That’s how underpricing slowly kills the original deal you made with yourself: freedom, control, and work you can be proud of.

Five moves that change the numbers

You don’t need a complete pricing overhaul to get out of this. You need one reset you can actually hold. Here are five to consider:

1️⃣ Price for reality

Pick a number that holds up when the week gets real. It needs to cover delivery time, overhead, and profit, plus enough spare capacity to keep improving the business. If you’re pricing without a view of your weekly capacity, you’re guessing, and guessing usually lands low.

A simple way to sanity check it: work out how many hours a week you can genuinely deliver at a high level, then divide your monthly target by that capacity. If the number makes you wince, that’s useful data.

2️⃣ Raise prices for new clients first

Start here because it’s clean. Set a new baseline for anyone coming in from today onwards and stick to it. You’ll get less noise, fewer negotiations, and better-fit clients faster than you expect.

If you want a line you can use without over-explaining:

“My pricing has changed to reflect demand and delivery depth. From [date], it’s [x].”

3️⃣ Stop discounting, reshape the job

Discounts feel easy in the moment, then they poison delivery. When someone pushes on budget, change the shape of the work. Reduce deliverables, tighten support, or shorten the timeline. Keep the price tied to what you’re taking on.

A simple line that holds your ground:

“If budget is the constraint, we can reduce scope.”

4️⃣ Choose clients on purpose

Underpricing sticks around when the wrong work keeps getting in.

Put a minimum budget on the table early. Be clear about boundaries that protect your week, like response times and revision limits.

If someone becomes difficult before you’ve even started, take the hint.

A line that saves hours of future pain:

“I’m not the right fit for that budget.”

5️⃣ Stop “free work” taking over

The quickest way to lose margin is by expanding the job.

Define what’s included, what counts as extra, and when the project ends.

If you find yourself doing favours to make a client happy, that’s usually a pricing issue showing up in behaviour.

When a ‘quick extra’ lands, keep it simple:

“Happy to do that. It’s outside the original scope, so I can send an updated quote, or we can swap it in by removing something else.”

Price it like you mean it

Pick one change and lock it in before Friday, whether that’s a higher new-client rate, a minimum budget, tighter scope, or dropping default discounts.

Once the price holds up, you stop packing the calendar to make the numbers work and you can deliver without rushing, which is when the business starts to feel lighter.

Better clients usually follow, because people who pay properly respect boundaries and decide faster, and that’s when it feels like yours again.

— Vanessa Ugatti teaches the full True Worth approach in her masterclass and shares her best selling book free on her website. You can also find her on LinkedIn.

AI slop is flooding everything, and it’s getting boring fast.

LinkedIn is the worst for it. You’ll see a “thought leadership” post that says absolutely nothing, then 50 comments underneath acting like it changed their life… and they all end with a question, funnily enough.

Substack Notes has plenty of it too, and X is basically a stream of recycled takes with new fonts. It’s as if everyone is using the same AI growth and engagement tools, which they likely do. Whole feeds are turning into churned AI output, and half the time it reads like bots replying to bots.

YouTube and TikTok creators have caught the same bug, you can hear it in the scripts now. A real person on camera, reading lines that sound like they came straight out of a prompt and nobody edited them.

What’s broken here isn’t the tech, because this isn’t an anti-AI rant.

I use AI every day across multiple tasks. It’s the missing judgement.

People outsource the moment where they’re meant to decide what they think. The result looks polished and still feels empty, because nobody made an actual point.

I’ve already written about the telltale ChatGPT voice and how to clean it up. This guest piece takes the next step.

I asked Sam Illingworth from the Slow AI newsletter to lay out a practical framework for bringing judgement back into the process, so your writing has a spine and your comments sound like you actually read the post.

Here’s Sam’s framework, with the gloves off:👇🏻

Why everything reads the same now

— A guest post by Dr Sam Illingworth

Authenticity now depends on judgement. Without it, you’re just filling space.

In 2026, text is basically free to produce, so the feeds are saturated.

You see confident writing with nobody behind it, and you can feel the missing judgement.

Bad AI writing is easy to spot and easy to fix. Slop looks fine on the surface, and it still carries no decision or ownership.

We are supposed to be the point at which judgement enters the system. When we delegate that role away, the result is unforgivable.

When publishing gets too easy

The issue is what happens when publishing stops requiring a choice.

When words arrive instantly, it becomes easy to publish without deciding whether something should exist at all.

Drafts appear finished before anyone has asked what they are for or who they are for. Voice flattens because nothing has been weighed.

This is slop because no one stood behind it. You give up your voice when you stop stepping in.

Write where you have to make a call

Write the first draft on your own. Keep AI out until the point is clear.

This is where judgement begins. The draft can be rough. It needs a point of view, a clear decision about what matters, and a sense of what you’re risking by saying it.

If the draft feels a bit exposed, that’s usually a sign you’ve made a real call.

Bring AI in after that. Use it to edit the work, not to write it for you.

Use AI as pressure to stress-test the argument, spot what you’re avoiding, and see what you’d actually stand behind under pushback.

If AI makes the decision for you, the work is already lost.

Keep AI in its place

AI is useful when it is clearly not in charge.

Used well, AI supports the thinking and stays out of the driving seat.

Use it for three jobs:

• First, challenge. Ask it to identify where your reasoning breaks under scrutiny.

• Second, exposure. Ask it which sentences signal safety rather than intent.

• Third, context. Ask it for cases that complicate your position rather than flatter it.

You’re still responsible for what stays in. That’s the job.

Comments are judgement in public

The same rule applies in the comments.

Generic comments are everywhere, and they read like drive-by approval from people who didn’t read the post.

A good response takes a position and adds something real to the thread, whether that’s a challenge, a useful detail, or a sharper question.

If you’re not willing to use judgement, don’t comment. Silence beats auto-agreeing.

A Slow AI prompt

Use this prompt in your AI tool of choice after you have written a full first draft.

That draft might be a mission statement, a strategy note, a report, or an email you are about to send.

The purpose is to force judgement back into the process.

You are a founder reviewing a first draft. Your task is to interrogate the judgement behind the text, not its writing quality. Write this for a sceptical peer audience. Use a tone that is critical and unsparing.

Read this draft and produce the following: identify the three places where judgement is weakest or most deferred, explain what decision is being avoided in each case and why that matters, and highlight any sentence that reads as publication without ownership.

If the response creates hesitation or discomfort, that is the point.

Judgement is the job

AI slop comes from people giving up agency, then publishing anyway.

You exist to make calls on what gets said and what stays unsaid.

When that responsibility gets handed over, the result can read well and still carry no weight.

Slow AI means you don’t outsource judgement. AI can help you test your thinking, then you decide what stays. The aim is publishing with ownership.

AI can help you think. Responsibility stays with you.

Write as someone who is prepared to stand behind every sentence.

— Slow AI has recently launched a new 12-month programme of critical AI literacy. This is free to all paid subscribers, and Sam has provided all Millennial Masters readers with a 33% discount, so a yearly subscription costs just $70.

See the Slow AI Scholar 100

👤 About Sam Illingworth

Sam is a Professor of Creative Pedagogies at Edinburgh Napier University. His work uses poetry and games to spark dialogue between scientists, technologists, and the public.

He also writes Slow AI, a newsletter that pushes back against urgency and hype in tech. It’s a call to build systems that reflect us carefully, ethically, and on human terms.

Slow AI

Get weekly Slow AI prompts that help you think with more intention, create with less pressure, and develop a calmer, more human way of using AI.

By Sam Illingworth

A guest post by Joel Salinas: I run Leadership in Change, where I help 3K+ mission-driven leaders implement AI without drowning in tool chaos and in risk.

Many founders I work with spend thousands monthly on AI tools and actually add more work to their plates. Something’s broken.

They think it’s a binary choice. Either use AI for everything or avoid it completely. Either give everyone ChatGPT access or ban it entirely. That’s just not how this works.

The real question isn’t whether to use AI, but figuring out what you’re actually good at and protecting that. Everything else around it? That’s where AI belongs.

When Daniel asked me to write about this, I knew exactly what I wanted to get across to founders and operators like you. Here it is: 👇🏻

The work that still belongs to you

Most leaders start automating before they’ve worked out which parts of the job actually need them.

At Atlan (a data startup), they built 152 agents that made 4,000 runs in five weeks (from Carilu Dietrich). They reduced multi-hour processes into faster workflows. Strategic decisions and product direction stayed with the team.

AI handled the repetitive analysis and routine updates.

This worked because the team was clear about where judgment mattered. The founders understood their data infrastructure expertise was irreplaceable. Everything built to support that expertise became a candidate for automation.

This is something I keep going back to: the leaders who get the most value from AI aren’t the most technical, just the most honest about what they’re actually good at.

I watched a 60-year-old nonprofit director with zero technical skills get better results than a 28-year-old SaaS founder who’d been coding since high school. The difference? She knew exactly what her unique value was. He was still trying to do everything himself.

The damage nobody budgets for

Here’s the mistake I see constantly… many leaders give everyone on the team ChatGPT access and call it an AI strategy.

In practice, it adds risk without anyone being responsible for the outcome.

82% of enterprise leaders now use AI at least weekly, but here’s the number that matters more: 72% of organisations now formally measure AI ROI (Wharton).

That shift happened because early adopters learned the expensive lesson that adoption without accountability creates chaos.

Leaders assume AI tools are like email or Slack. Give everyone access, and they’ll figure out how to use it responsibly.

But AI is different, it generates content that looks professional even when it’s factually wrong or tonally off-brand.

AI creates work that passes a quick glance but fails under scrutiny.

The questions that matter first

So how do you avoid this? Forget the tools for a minute.

Answer these four questions first:

1️⃣ What decision or skill made you a founder in the first place?

Write this down, and I mean actually write it. Be specific. “I’m good at business” isn’t an answer. “I can spot inefficient processes in healthcare operations and redesign them” is an answer.

This is your protected zone. AI doesn’t touch this. You might use AI to support it, to research competitors, to analyse data, to draft documentation, but the core insight stays with you.

The reason this matters is simple: if you delegate your core competency, you become replaceable. I’ve seen founders automate themselves into irrelevance because they couldn’t articulate what made them uniquely valuable.

2️⃣ What work surrounds that core skill but doesn’t require your judgment?

Make a list of everything you did yesterday. Circle the tasks only you could do because of your unique insight or relationships. Everything else is a candidate for delegation.

For me, that’s first drafts. I’m good at translating complex AI concepts for mission-driven leaders. That’s the skill that built my publication. But I don’t need to personally type status updates or format spreadsheets. Those tasks don’t require my strategic judgment about what resonates with nonprofit directors or church leaders.

The key distinction is between tasks that require your specific expertise and tasks that require general competence.

AI can handle general competence. Your expertise is what people pay for.

3️⃣ What would you do with 10 extra hours per week?

Stop reading, and try to write down the answer.

This tells you what’s actually valuable. If your answer is “more sales calls,” delegate everything that isn’t sales. If it’s “more time thinking about product strategy,” delegate everything that isn’t strategic thinking.

I answer this question every quarter because the answer changes. Right now, my answer is “more time in actual conversations with leaders.”

That tells me I should delegate anything that keeps me behind a screen when I could be on a call, understanding what leaders actually struggle with.

4️⃣ What’s the cost of getting it wrong?

Some tasks have high costs if AI makes a mistake: client proposals, financial decisions, hiring, anything involving legal issues. These need human review even if AI creates the first version.

Some tasks carry very little downside, like formatting documents, organising files, or drafting social posts. These can be fully delegated because fixing an error takes less time than doing it yourself.

The real question is how much damage a mistake would actually cause.

A formatting error in an internal memo costs you nothing. A factual error in a client proposal costs you the client.

Where teams mess this up

Lastly, I want to go over some of the most common mistakes founders make when it comes to using AI.

Mistake 1️⃣ Delegating without context

“Write me a strategy document” produces garbage. “Write a 3-page strategy document for our Q2 product launch, focusing on enterprise healthcare customers, using data from our last survey” produces something useful.

The quality of AI output is directly proportional to the quality of your instructions. Vague inputs create vague outputs.

Mistake 2️⃣ No guardrails

I recently saw a nonprofit communications disaster, and it happened because they gave everyone ChatGPT without guidelines on voice, fact-checking, or approval processes. The fix is creating simple rules about what needs review and what doesn’t.

Mistake 3️⃣ Not measuring the tradeoff

Crowd Tamers reduced client costs from $8,000 monthly to $1,500 by automating video edits and social posts. They measured exactly where time went and what it cost. Most leaders guess. Successful ones track.

Mistake 4️⃣ Trying to automate everything at once

I spent three months trying to automate something I should not have. Complete disaster. I was spending more time fixing the output than writing from scratch. I wasn’t starting where I needed to start.

That’s it! You are ready to start, wisely and strategically.

Where this goes in 2026

Implementation is messier than it looks on paper. The framework is simple. Applying it to your specific workflow requires knowing what questions to ask.

If you want to walk through this framework for your specific situation, I’m offering 50% off implementation reviews to Millennial Masters readers, starting with a free 15 minute intro.

We’ll create a map of your five highest-leverage AI opportunities and a plan to implement them. Most leaders find at least 10 hours per week.

You can book an intro call here.

Start small. Measure everything. Protect what makes you different.

Leadership in Change

Don’t just read about AI, lead it. Get the weekly playbook for leaders who want to supercharge their expertise and multiply their impact.

By Joel Salinas

No founder I’ve spoken to had a neat starting point with AI.

When GPT arrived, there was no playbook. Just a new tool, a lot of uncertainty, and work that still needed doing. Most people figured it out in spare moments while trying to keep the business moving.

That has been consistent across the 55+ Millennial Masters conversations I’ve had over the past year. Founders did not trust AI first and then use it. They used it on real work, got frustrated, learned where it helped, and came back when the old way felt too slow.

Three years into the GPT era, AI still is not smooth. It can be stubborn, inconsistent, and harder to control than the hype suggests. I’ve spent hours fighting with this very draft while it ignored instructions I was being explicit about.

Even so, it has already worked its way into businesses through the repetitive tasks that quietly drain time.

Here’s where founders are already using it to take pressure out of their work. 👇🏻

The work that disappeared first

AI tends to stick first in work people keep putting off.

Carly Meyers describes the decision happening while the task is already open. “One of the most powerful questions… is when they say, ‘I wonder if AI can do this?’… This thing that I’m doing right now is boring. It’s monotonous… I wonder if AI could help me with this.”

Ryan Carruthers applies the same thinking to sales conversations that would otherwise sit untouched. “I reactivate dead leads via AI… It doesn’t matter if it all goes to pot because they’re dead anyway… then I can start to get rid of some of the repetitive tasks.”

James Augustin uses AI to break down sales call transcripts and flag what worked and what fell flat, without anyone having to trawl through the recordings. “I think the first thing is humans should be doing things that are innately human… they should be going out to sales meetings… recording podcasts… talking about strategy.”

With AI, people stop doing the boring work once they see it doesn’t need them anymore.

Building gets cheap, distribution doesn’t

As the cost of building drops, ideas move sooner. Testing something no longer eats up weeks of time or a large chunk of budget.

Simon Jenner sees this clearly in early product development. “We’ve got vibe coding, which allows you to use the AI prompt to do it… It gives you the advantages of code, which is scalable.” When building is cheap, it becomes easier to find out quickly whether something deserves more attention.

Gus van Rijckevorsel described how this plays out in game development. “Something that we could have done in four months, we can do it in two weeks.” That removes long (and expensive) stretches where nothing can happen. Teams can test features quickly and spot duds before weeks get burned on them.

As development gets cheaper and faster, the work moves elsewhere. Reaching the right people starts to matter more than perfecting the thing itself.

Distribution, audience fit, and getting in front of a specific group become the harder problems once shipping stops being the bottleneck.

Who’s still needed

You don’t need as many people once AI is doing a meaningful share of the work.

Roles that existed to deal with volume, admin, or routine output start to disappear when the first pass is handled automatically.

Nick Holzherr has been blunt about what he’s seeing. “They’re not hiring junior marketing people anymore. They are hiring more senior people that can use AI. So they just need less people.”

Nick Telson-Sillett described the same pattern in customer support. AI deals with most incoming queries before anyone gets involved, which means people only step in when a conversation needs judgment, reassurance, or experience. “AI handles about 70% of our support tickets,” he said.

The practical result is that teams stay smaller, and the people in them sit much closer to decisions that actually matter. AI absorbs the volume and repetition, while humans focus on the moments where context, trust, or money are on the line.

What doesn’t get delegated

As AI produces more output, deciding what to act on starts taking longer.

This shows up clearly in recruitment. Noel Andrews explained how “resumes and CVs are now 100% useless because of AI… It’s like AI scoring AI. It’s just rubbish.” When applications, cover letters, and even interview answers are generated with the same tools, polish stops being useful. What matters instead is how someone thinks, reacts, and reasons when they don’t have time to outsource the answer.

The same pressure appears when deciding where automation belongs inside a business. Oliver Yonchev talked about how cheap access to thinking tools has changed expectations. “The cost of deep thinking work and planning and strategy and business consulting is a £20 a month subscription on ChatGPT.”

Yota Trom uses AI as a way to refine ideas without handing responsibility over. “My philosophy around that is that AI is my editor, not my creator.” In practice, this keeps judgment with the person doing the work, even when the tool can suggest endless variations.

AI produces material quickly, but someone still has to decide what matters, what gets ignored, and what carries risk if it goes wrong. The work shifts toward judgment, because that part can’t be automated without consequences.

Owning the outcome

As AI takes on more execution, the value in a business shifts away from doing the work and towards owning the outcome.

This comes up most clearly when people talk about software. Thibault Louis-Lucas sees a future where building the product stops being the hard part. “Imagine if… you do not need developers at all to create products. So where is the value then if it’s not in the product itself?” When anyone can prompt a working tool into existence, attention moves to distribution, reach, and trust.

Peter Watson was blunt about what happens to agency businesses built entirely on execution. “I don’t think we’re far away from three button clicks, no advertising agency required.” When the doing gets automated, businesses that sell time or output struggle to justify their place. What survives is direction, taste, and knowing what to do with the tools once they exist.

Nick Telson-Sillett pointed out that high-value sales still hinge on human trust. “If you are selling anything over $50,000 and above, the person taking the bet on buying a software will want to speak to someone.” AI can handle volume and qualification, but the moment risk enters the conversation, people still want a person on the other end.

Jordan Stachini raised concerns about how skills develop when junior roles disappear. Creative work has traditionally relied on people learning by doing, often badly, before getting good. When AI replaces that early stage, the path to senior judgment becomes harder to see.

Some people are already building around this shift. Carly Meyers described running her business by assigning AI agents distinct roles, treating them like an internal advisory layer. She consults them, delegates work to them, and uses their output to inform decisions. In her view, companies built by one or two people will become normal once execution stops being the bottleneck.

As execution keeps getting cheaper, what carries weight is deciding what to build, who it’s for, and how it reaches them.

2026: Still figuring it out

There still isn’t a rulebook for using AI in a business, and after the last year of conversations it’s hard to imagine one that would actually help.

What people are really dealing with is how their role shifts once a lot of the busywork is gone. The time doesn’t magically free up. It gets pulled into decisions they can’t dodge anymore, or choices they used to push down the line.

AI will still dominate the conversation in 2026, mostly because most people are still trying to make it useful without letting it take over their day.

I’ll keep digging into that through Millennial Masters by staying close to how founders and operators actually live with these tools once the novelty wears off and the trade-offs become harder to ignore.

I’ve lived both sides of it. At times, having the right person beside me made uncertainty easier to hold. Long nights locking in felt purposeful rather than isolating. Even small things, someone picking up the tab or saying “keep going,” changed the tone of an entire week.

At other points, that grounding wasn’t there, and setbacks lingered longer than they should have. None of this shows up in founder stories, but it quietly decides how long most people last.

When I asked Millennial Masters about grounding and pressure, the answers weren’t about gym routines or journaling. Those things help, but they’re rarely what carries you when things get tight. What kept coming up was the person closest to them.

The partner who picked up the tab when payroll loomed. The one who held life together while the business took over. The one who stayed steady when confidence dipped. The details varied, but the effect didn’t. Having someone next to you made the uncertainty survivable.

Strip it back far enough and the lesson stops being subtle. The person closest to you often decides how much pressure you can actually survive. 👇🏻

When everything else feels unstable

Nick Holzherr’s answer caught even him off guard. When asked about the best decision he made as a founder, he didn’t mention a product call or a hire. He talked about his wife.

At a point where his work life felt close to collapse, she represented something the startup could not offer: stability. She had a career that did not swing with funding cycles or product-market fit, and that mattered more than any tactical decision inside the business.

“I think to marry my wife, an unexpected answer here, but she’s a doctor, she’s got stable career,” he told me. When Whisk looked like it might fail and money felt uncertain, that stability became the anchor. “She was the stability and also the encouragement.”

What comes through is not romance, but containment. A life outside the business that did not amplify the chaos inside it. Especially early on, that separation gave him space to take risks without everything else collapsing at the same time.

When the noise drops

For Kamal Ellis-Hyman, marriage changed how he related to ambition itself. When asked what advice he would give his 17-year-old self, he framed it as a structural shift rather than an emotional one.

“Marriage is going to be the single most impactful factor of all the things you’re dreaming about right now,” he said. Not because it made him work harder, but because it removed the constant need for approval.

Having his wife next to him changed where validation came from. “I don’t seek approval like I used to because I’ve got my wife next to me. I have a place where I can come and just be me.”

That grounding had knock-on effects everywhere else. Decisions became cleaner. Pressure stopped leaking into every interaction. The business benefited because the person running it no longer needed it to provide identity or reassurance.

When there’s no safety net

Ryan Carruthers is blunt about how misleading the idea of overnight success can be. People see the outcome and invent a story around it. His wife lived the reality.

“We lived off of her savings,” he said. Not briefly, but long enough for it to become normal. They met young, before there was anything to show, and when the business had nothing to offer except a belief that it might work.

That kind of support is rarely visible from the outside. It does not show up in pitch decks or LinkedIn posts. It shows up in rent paid, pressure absorbed, and someone saying go and build this when there is no safety net.

The work nobody sees

Lauren Currie names what often gets left out of founder stories. The invisible systems that make ambition possible.

Her partner was a full-time stay-at-home dad for the first three years of their son’s life. “That’s the only reason I was able to build some of those businesses,” she said. Childcare, domestic labour, and emotional load were not background details. They were the enabling conditions.

“There’s an unspoken infrastructure behind success,” she said. One that is still too often treated as incidental, even though without it many businesses simply would not exist.

Someone who tells you the truth

James Fleming runs his business alongside his wife, Enas. He credits her belief as something more operational than emotional.

“She’s never once doubted me and my abilities to move the needle,” he said. Without her running the business the way she does, he is clear that it would not exist in its current form.

William Stokes describes a similar role from a different angle. His partner Jess acts as counsel, the person he talks problems through before acting. “Ninety-nine percent of the time she’s much more level headed than me,” he said.

In both cases, the partner is not a cheerleader on the sidelines. They are part of the decision-making loop, shaping outcomes long before they become visible.

Taking the doubt for you

Jason Graystone talks openly about the social cost his wife carried while he took risks others did not understand. When you go against the norm, the doubt does not only land on you.

“She’s had to deal with external pressures of her family,” he said. Questions about whether he knew what he was doing. Whether the risks were reckless.

That kind of pressure can fracture relationships. In this case, it reinforced one. The partnership absorbed doubt so the business could continue.

Who lets you lock in

Peter Watson is direct about the impact a partner can have on focus. “The person closest to you often decides how much pressure you can survive,” is the thread he keeps returning to.

He credits past partners for allowing him to build when it mattered. “Both were phenomenal for my business journey,” he said. They allowed him to lock in, rather than pulling attention away when it was needed most.

His warning is equally clear. A toxic relationship drains energy and erodes confidence, and no amount of discipline compensates for that.

Emma Mills saw this from another angle. Before meeting her current partner, relationships were hard to balance with entrepreneurship. Her partner now runs his own business. He understands the trade-offs. “He gets it,” she said. “Prior to Joe, that’s not been an easy thing.”

When work stops being everything

For Kevin de Patoul, family is the fastest way to regain proportion. When work stress spikes, he steps back and checks what actually matters.

“My family is the most important thing in my life, a lot more than my business, to be very honest. So that’s something that helps a lot and gives me perspective to what is actually important when there’s moments of stress at work,” he said.

“I can always just take a step back and say, wait… my kids are fine. So actually everything is fine.” That reset keeps pressure from spiralling and stops the business from becoming the only measure of success.

What changed everything

When I look back at the hardest parts of building, the damage came from how exposed I felt while doing it, and from carrying uncertainty day after day.

Building doesn’t happen in isolation, even if we like to tell the story that way.

How far you push, how long you hold on, and how much risk you sit with is shaped by what life feels like around the work.

And more often than people admit, the person closest to you plays a role in that.

Sometimes you have to carry it alone for a while and give yourself space to lock in.

That stretch feels endless when you’re inside it, but it rarely is.

More raw insights on Millennial Masters:

I know, fundraising is never really off your mind. One round closes and the next one is already looming in the background.

I went back through more than fifty Millennial Masters interviews to pull out the lessons founders said made the biggest difference when trying to move a round.

What stayed with me was how much of it had started earlier than people like to admit.

By the time the deck is doing the rounds, a lot has already been decided by the work that happened before that.

Here’s what founders said worked. 👇🏻

How you get in the room

Warm introductions change the tone of the first conversation.

Tom Wallace-Smith said it well: “The difference in cold introductions versus warm introductions is like night and day. A warm introduction, that person’s almost avowed for you.”

You feel that straight away. The investor is more open, the conversation moves faster, and you spend less time trying to prove you should be in the room at all.

If you do not already have a network, you have to build one. Yehong Zhu talked about finding lists of female founders and investors, adding them on LinkedIn, and starting from there.

“I didn’t have a preconceived network.” It was slow, but it gave her a way in. By the time she reached out for capital, some familiarity was already there.

Kevin de Patoul got at the same thing from a different angle. A lot of the useful relationship-building happens in the quieter periods, before a raise is live and before anyone is asking for money. That is why visibility matters.

Nick Holzherr had an unusual version of that. After appearing on The Apprentice, he could email investors and say, “Hey, I’m Nick, I was on the Apprentice,” and that alone gave him an opening a lot of founders spend years trying to create.

Tom Wallace-Smith also talked about meeting future backers at a house party in Virginia during a conference in Washington. That pushed his round forward too. A lot still comes down to being in the right room often enough for something to happen.

When things go badly, the best founders do not stay still for long. Lara Varjabedian has a habit that kept her moving. “Every time some bad news happens, I reach out to ten potential partners or ten potential investors.”

How a pitch gets better

You almost never start with the version that works.

You get there by having the same conversation again and again, usually with people who are not quite the right fit but are still useful because they show you where the story is weak.

Tom Wallace-Smith said those early investor meetings helped him hear which parts were not landing before the pressure was higher. That works better when you use those conversations to test the pitch instead of trying to perform it perfectly.

Tom made the next part of it very clear: “The stakes have to be high.” Investors pay more attention when the problem feels real, costly, and hard to ignore. They want to hear what actually happens if this does not get solved.

Nick Telson-Sillett had a useful reminder for founders who do not have revenue yet. “If you haven’t sold $1 yet, but you come to me with interviews of a hundred people you’ve spoken to, that’s traction at pre-seed.”

At that stage, traction does not always mean money. Sometimes it just means proof that you understand the problem properly.

Joshua Western talked about how different investors listen for different things. “By an American venture capital firm, I’ll be asked, how big can this be? A British investor will ask me, if everything fails, what’s the value left in the company?”

The pitch gets better when you understand what the investor is actually trying to figure out.

Tom Wallace-Smith also found that investors who passed sometimes still made introductions, and those early calls helped sharpen the pitch and open up the round.

Not every useful conversation ends with a yes.

Choose the right kind of money

Crowdfunding can work well when the round is doing two jobs at once: bringing in money and bringing people in early.

Liam White described it like this: “You get this whole bunch of evangelists who come on board with the journey.”

He was also clear that a campaign does not really start on launch day. If you can raise thirty to fifty percent of the round before it goes public, the whole thing has a much better chance of moving once it is live.

Some founders go private instead because it is simpler and cheaper. Sam Holmes got straight to the point: “Private comes a lot cheaper.”

That matters even more if you think you will raise again later, because fees that look manageable once can get expensive quickly.

What the early years really cost

The earliest stage takes more out of you than most people realise.

Rob Smith worked demanding construction shifts while keeping one day each week for product development. That was how he kept the idea alive while saving for the first build.

Sometimes the cost is more personal than that. James Fleming recalled: “I actually had to sell my watches. My wife sold her gold just to keep the marketing running.”

That’s the kind of pressure a lot of early founders are carrying while still trying to keep the business moving.

Lara Varjabedian talked about one of those moments turning into something useful. She met one of her early angels at an event and closed the commitment over coffee the following week. When there is no safety net, one conversation like that can keep things moving.

Early decisions can do damage too. Gus van Rijckevorsel summed up one of his biggest mistakes in a few words: “A massive cap table with a very large valuation. Never do that.”

Some early mistakes keep showing up long after the round is done.

The work doesn’t stop after the raise

Closing the round does not take the pressure off for long.

Nick Telson-Sillett is very clear about that. “I think it’s criminal for founders that don’t speak to their investors.” He expects monthly updates that cover what is moving, what is not, and where help is needed.

He also pays close attention to what a founder has already had to get through. “The more challenging stories they’ve had to overcome will probably make them a better founder.”

Tom Wallace-Smith made a similar point. He told me there is “not really a pause” once you start raising. He plans for the next round early, so he is not trying to do it all under pressure when cash starts getting tight.

That does not mean turning the business into a loop of spending and fundraising. Nick described that version of it pretty well too: “spend all the money, raise again, spend all the money, raise again.” That pattern catches up with you faster than you think.

Don’t wait until you’re raising

Most of the work that moves a round starts before you are properly raising.

If you take this seriously, start earlier. Build the relationships that might matter later, get yourself into the rooms where useful conversations happen, and keep working on the pitch until it gets clearer each time you explain it.

That is what makes a round feel warmer when it finally opens. You are not arriving out of nowhere, and you are not trying to work everything out at the last minute.

None of this has to be loud. It just has to keep happening.

Early introductions matter. So do the smaller conversations around them. Each time the pitch gets clearer, the next conversation gets easier.

If you leave all of that too late, the round gets harder than it needs to be. If you start earlier, you give yourself more room to move.

Two more reads before your next investor pitch:

If you are raising in 2026, you don’t need more pitch deck tips. You need to understand what the investor across the table is actually judging while you talk.

Chris Tottman has watched thousands of pitches. He’s founding GP at Notion.vc, has backed hundreds of founders, and spends his time close to the reality of early-stage B2B.

I asked him to explain how he really judges founders. What came back was a much clearer picture of what investors like him are actually listening for.

Here’s how he thinks: 👇🏻

1️⃣ Start with pain

“It always starts with the pain,” he told me. When a founder can say “my buyer is losing sleep because…” and back that up with detail, he leans in.

He wants to know what keeps going wrong for the buyer and why they are still putting up with it. The pitch gets much stronger when a founder can walk him through the mess rather than just naming the market.

One founder talked him through the legal spend chaos inside a CFO’s inbox. Chris could see the delays, the handoffs, and how quickly more people got pulled into the problem. It sounded first-hand.

That is usually the difference between a real problem and a nice-to-have. If you cannot paint that picture, he assumes you have not been close enough to the buyer’s world.

Go into a fundraise able to walk an investor through a day in your buyer’s life. Show them where the friction actually sits.

2️⃣ The ‘painful kernel’

Chris uses the phrase “painful kernel” a lot. It is the part that really hurts underneath all the talk about efficiency, automation, or AI.

He is listening for whether you have isolated that pain properly or just wrapped a broad market story around it. To stand out, you need to get specific about what keeps breaking and why the buyer still puts up with it.

He pays close attention to how that understanding was built. Have you interviewed buyers, shadowed teams, or sat with support logs for weeks? Or are you repeating second-hand opinions?

This is where a lot of pitches start to wobble. Big claims about the market, not much understanding of one real user.

Make that painful kernel concrete enough that an investor can see exactly where the pain sits and why it matters.

3️⃣ Better is not enough

Chris comes back to this a lot: the best founders solve unique problems. It connects to another line he uses often: “Don’t be better, be different.”

A bit faster or a bit cheaper is rarely enough now. He is looking for a different workflow, a different way to package or sell, or a corner of the market incumbents keep missing.

That difference might sit in pricing, in distribution, or simply in how the whole thing is framed.

You need to be able to explain that difference in a sentence. Which belief are you pushing against, and why does it matter for the buyer?

If Chris has heard the same angle three times that month, the bar moves.

Write down, in one line, what makes your approach different. If it sounds like everyone else in the market, you are not there yet.

4️⃣ Solo is not the problem

Chris does back solo founders. He just wants proof they are not building everything in their own head.

He asks simple questions. Who challenges you? Where do you get feedback? Then he listens for how real the answer sounds.

The strongest solo founders can point to real people around them: early hires they have already pulled in, operators they message for blunt feedback, and customers who push back like partners. The weak answers sound vague: lots of people, no names.

He is also open about his own dyslexia and pays attention to founders who have had to build around something.

What matters is whether they understand their own limits and have done something about them. “Here is what I am not good at, and here is how I have built around it” is a green flag.

Bring your circle into the story. Show who keeps you honest and how you have built around the parts of the job that do not come naturally.

5️⃣ Obsession sounds specific

Chris is blunt about founder-led sales. If you can’t talk about your customer in depth, the rest of the pitch doesn’t matter.

He starts with one question: when did you last speak to a customer? Then he keeps going. Can you quote what they said? Do you know how they buy, who signs off, where deals stall, and what actually creates urgency?

The founders who impress him can walk through 30 conversations without notes. They can explain where deals begin to slip inside the buyer’s company, which objections are real, and which ones are just smoke.

He is testing whether you have really been doing the selling. The detail tells him that faster than any claim about customer obsession ever will.

Treat customer conversations as your real fundraising prep. Go in ready to talk through them as if the investor were your next sales hire.

6️⃣ Clarity beats hype

The last few years have filled venture with hype cycles. AI now, SaaS before that, something else next. Chris sees all of it, but he keeps coming back to one word: clarity.

He likes founders who can operate in what he calls hard mode. That might mean a messy market, a long sales cycle, or a sector nobody is excited about. He still wants to see that they stay close to value and keep moving.

Presentation style matters less than people think. A lot of the founders who stayed with him were not loud in the room. They came back the second time with more evidence and a clearer sense of the customer. That changed his mind.

Do not over-rotate on performance. Sort your thinking out first. Be clear on the problem, the buyer, and why your wedge matters.

If you are raising this year, read this again before you send the next deck.

Go back to the pain, get closer to the customer, and make sure the pitch is backed by work you have actually done.

That is the bar investors like Chris are setting.

If you want more of Chris’s thinking, his newsletter The Founders’ Corner and his GTM Handbook go deeper on this stuff. Treat them like reference manuals rather than content.

The Founders Corner®

Your weekly BOOST to Raise and Grow Like A Pro. Tips and Techniques used by prolific Founders.

By Ruben Dominguez

Chris Tottman has a new book, The Big Book of Brain Dumps, built from the ideas that shaped his career and the lessons drawn from backing more than 500 founders. It’s for anyone trying to raise, scale, or make better decisions when things get messy.

Two more reads before your next investor pitch:

I started before I felt ready, because the only way to test the idea was to publish it.

Since then, fifty-two episodes have turned into a real body of work. The YouTube channel has reached 27,000 subscribers. The newsletter has grown to more than 5,600. Each week, more than 32,000 people now tune in for unvarnished founder conversations, told while the work is still happening.

Before I publish the next run of episodes, I wanted to take stock of what this year actually produced. Metrics are useful, but they are rarely the point. The point is what you learn when you listen back carefully.

When I revisited the conversations, a pattern became hard to ignore. Founders describe pressure in surprisingly similar terms. They return to the same decisions, even when their industries differ. They are frank about uncertainty in a way that is rare in public settings.

That is what I want to hold onto. What follows are the 25 lessons that stayed with me, and that I intend to carry into the next year. 👇🏻

1️⃣ Your inner operating system

Build fitness into your focus

Many think fitness is all about aesthetics. But the people I interviewed described it as something closer to medicine. Regular training clears the noise, steadies emotions, and creates the headroom you need when everything else is unpredictable. It’s about keeping your mind in a place where you can think clearly and lead without spiralling. Most of the founders who stay calm under pressure have some kind of physical anchor in their routine.

“Fitness is saving my life because it mentally calms me.” – Francesca McClory

---

Use structure to protect your time

Every founder battles interruptions. Structure forces the day to serve your priorities rather than the other way around. Blocking hours for strategy, deep work, or outreach isn’t rigid. It’s what keeps your attention from being eaten by noise. Several guests described this as the moment their output doubled. Clarity comes from defining when you think, not just what you think about.

“Structure creates efficiency. And by having structure, you can be more efficient.” – Will Polston

Steal the shortcuts from people ahead of you

Many guests talked about the years they wasted figuring things out alone. The consistent pattern was learning faster by studying people ahead of them. Not copying, but compressing the timeline by understanding which mistakes are optional. Founders who rise quickly build a habit of seeking reference points. They want the shortcuts that experience can give without waiting a decade to earn them.

“Probably could have reduced 10 years of work into like three years probably.” – Jack Good

---

Keep a habit of honest self-reflection

The founders who move forward fastest are deliberate about how they think. They reflect without punishing themselves and treat reflection as a calibration tool. Daily journaling, end-of-week reviews, voice notes, or short meditations all came up in interviews. It’s how they spot patterns in their reactions and improve their judgement.

“Self-reflection is key. I really think a lot about how I handle situations, how I can better do things next time, but I don’t beat myself up.” – Gemma Price

2️⃣ How you actually make progress

Start with the smallest real version

Action came up more than ambition. The founders who build momentum don’t wait for a perfect plan. They move now, even if the first version looks scrappy. The earliest version is the diagnostic tool. It tells you what matters and what doesn’t. It’s how you find truth quickly.

“What is the minimum viable version? Up front we call it skateboards.” – Lauren Currie

---

Consolidate ideas before overwhelming your team

Many founders drown their own teams in half-formed ideas. The strongest operators filter their thoughts before sharing them. They sit with ideas for a few days, test assumptions, and only escalate the ones worth executing. It protects the team’s capacity and sharpens leadership.

“Founders need to stop caring about ideas, right? Like frankly, no business fails because there’s not enough ideas.” – Harry Sanders

---

Let feedback steer your direction

Starting creates movement, which creates information. That information tells you where to go next. The founders who scale quickly treat feedback as insight. They listen to customers without defensiveness and treat every early conversation as data.

“The reality is the best thing you can do is just start. And through the process of starting, you get feedback. Feedback is insight.” – Oliver Yonchev

---

Test ideas by trying to disprove them

When you want something to be right, you hear what you want to hear. The sharpest founders avoid this trap by trying to disprove their own ideas. They ask harder questions, and seek critics, not cheerleaders. It prevents expensive detours.

“If you’re going out to prove to yourself that it’s a great idea, you will spin stuff. You will ask the wrong questions and you will paint too much of a rosy picture for yourself.” – Nick Telson-Sillett

---

Let the market define success

Team size, office space, brand perception. None of it matters as much as customers paying. The cleanest signal of product value is money. Founders who stay focused on this move faster and waste less.

“People giving you money for your product is the ultimate validation that you are doing something useful.” – Thibault Louis-Lucas

---

3️⃣ How you show up

Repetition builds trust

You don’t earn trust through novelty, but through consistency. Most founders underestimate how often a message must be heard before it sticks. The strongest brands repeat the same truth until the audience can say it back to them.

“The best way to build trust is to say the same thing over and over, over, over again.” – Jason Graystone

---

Lead with value before you ask for attention

Almost every strong marketer on the show said the same thing. Give something useful before you ask for anything back. People follow those who help them first. It also reduces friction in sales because the relationship starts warm.

“Always provide value upfront, wherever you can. That’s how you’re going to get attention.” – Brad Mac

Keep language simple

Complex ideas don’t need complex words. The best communicators strip everything back. They want clarity, not cleverness. If a 15-year-old wouldn’t understand it, it probably needs rewriting.

“The language you use to explain your concepts should never be complex.” – Andrea Pacini

---

4️⃣ The harder parts of the journey

Treat mistakes as materials for growth

Every founder said some version of this. Mistakes aren’t moral failures, they’re inputs. But only if you capture them. Writing them down forces you to learn instead of repeating them.

“It has to be a lesson… let’s keep prepping for that future me that’s always trying to learn.” – Dumi Siwo

---

Build a runway that lets you breathe

A long cash buffer gives you control. It makes hard periods survivable and protects the quality of your decisions. Many guests said they wish they’d built it sooner.

“I did build in my first two years, sort of like a long cash run in the business so I could get more comfortable with [bad times].” – Joe Averill

---

Use your early years for bold risks

Before responsibilities stack up, you have the freedom to swing bigger. Several founders said their biggest regrets were the risks they avoided, not the ones they took.

“What’s the worst thing that’s gonna happen? You go back to your job.” – Peter Watson

---

Accept the irrationality of entrepreneurship

Starting a business rarely makes sense on paper. It requires irrational belief. The people who make it work stay committed despite the odds, not because of them.

“Launching a startup is never the sensible choice. It’s not based on facts. Everybody thinks they’re going to be the one in a million person that pulls it off.” – Andrew Steele

---

Move even when uncertainty stays high

Founders often wait for clarity that never arrives. The uncertainty is permanent. Learning to act inside it is the advantage.

“The level of uncertainty that you have is not going to go away. You continuously have uncertainty and you’re continuously outside of your comfort zone.” – Kevin de Patoul

---

Build resilience through repetition

Real resilience comes from the cycle of setback and recovery. There’s no secret technique, only practice.

“The only way to build resilience is to get knocked down and get back up way more times you got knocked down.” – Carly Meyers

---

5️⃣ People and power

Hire people sharper than you

Delegation is only powerful if the person truly elevates the work. Your job is to find specialists who can outperform you in the areas that matter.

“The role of an entrepreneur is finding people that are smarter than you. That’s it. That’s your role.” – Gus van Rijckevorsel

---

Hire for problems, not positions

Several founders avoid generic job descriptions. They define the problem they need solved and hire someone who can own it from day one.

“Rather than hiring a position I’m hiring a problem. I’m hiring for a problem, hiring a solution.” – Kamal Ellis-Hyman

---

Document everything to scale

Documentation sounds slow until you realise it’s the only way to scale without chaos. It sets standards, reduces onboarding drag, and lets AI handle repetitive work.

“Working in writing a lot is critical to that. There’s also… write, document and create artifacts.” – Nick Holzherr

---

Protect culture at all costs

Technical ability never outweighs attitude. A toxic hire erodes everything you’re trying to build. People with the wrong energy cost more than they contribute.

“If their attitude stinks and they’re bringing toxic behaviours, again, that’s never gonna work.” – Francesca McClory

---

Lead by giving first

Relationships deepen when you help before you ask. Founders who build strong networks make generosity a habit. It comes back later in ways you can’t predict.

“I generally don’t need anything from anyone… it doesn’t cost me anything to give it… you put enough karma out into the world.” – William Stokes

---

Use AI to scale the previously unscalable

AI isn’t a gimmick, but a force multiplier. It turns manual bottlenecks into scalable workflows and frees founders to focus on judgement and creativity.

“AI makes the unscalable scalable.” – Oliver Yonchev

---

Act fast on red flags

Small issues never stay small. Founders who protect their time and culture confront problems early. It prevents long, expensive messes later.

“Every time I see something going wrong, it’s just getting worse and worse.” – Thibault Louis-Lucas

---

A year in, and still the beginning

A year of Millennial Masters feels both tiny and significant. Fifty-two episodes in, and I’m more certain than ever that founders don’t need more theory. They need stories from people who’ve lived the pressure, made the decisions, and carried the consequences. That’s what this project has become. A place where those conversations land.

This community now sits at more than 32,000 across YouTube and the newsletter, and it works because you keep showing up with the same curiosity the guests bring. Every lesson in this edition came from someone who told the truth about their journey. I’m grateful for that honesty, and for the room you’ve all helped build around it.

These conversations changed how I think about ambition, risk, and the weight founders carry quietly. If even one of these lessons steadies your decisions in the weeks ahead, this work is doing what it should.

We’re still early. The next batch of episodes will go deeper, ask better questions, and tell the kinds of stories that stay useful long after the episode ends.

If something in here helped you, pass it on to someone building their own thing. The right lesson on the right day can shift everything.

PS: If you’ve read this far and want to partner with Millennial Masters in 2026, I’m opening a few new spots. If your brand wants to reach founders, builders, and entrepreneurs, let’s talk.

At The Business Show in London I walked into a talk by retail entrepreneur and Dragon’s Den investor Touker Suleyman expecting the usual survival-mode advice… stay resilient, push through, keep grinding… the standard stuff.

Instead, he said something that caught me off guard. He looked across the room and said:

I wish someone had said that to me years ago.

When previous ventures of mine went sideways, the real pain wasn’t the failure. It was the aftermath. The obligations I had signed without thinking. The ones that followed me long after the company was gone.

Most founders I meet never talk about this part. It isn’t exciting and it doesn’t fit the upbeat founder narrative, but it influences your life more than any motivational talk ever could.

Touker’s message deserved more attention, so here’s what he meant and why it matters. 👇🏻

The risk that follows you home

During the session, Touker spoke about banks with unusual honesty. He said:

“Banks today are like pawnbrokers. They want to lend you money. They want your personal guarantee.”

Later he added: “Never, never give a personal guarantee on anything.”

He wasn’t exaggerating. If the business fails, the guarantee doesn’t disappear with it. It stays attached to you. Not your company… you.

Founders often fixate on interest rates or repayment terms and miss the clause that changes everything.

Personal guarantees feel harmless when things are going well. They turn into a trap the moment the market shifts or the business hits turbulence.

Here’s the part most people overlook: personal guarantees aren’t just for loans. They hide inside everyday business agreements.

I’ve seen them in:

• office leases

• serviced workspace contracts

• equipment rental

• accountancy and legal engagement letters

• merchant cash advance deals

• supplier credit agreements

• fit-out and refurbishment contracts

You assume it’s standard paperwork, you sign, and get on with your day. And without realising it, you’ve accepted personal responsibility for something you thought belonged to the company.

Touker’s warning was simple: know exactly what carries your name and push back wherever you can. Many founders don’t realise how much room they have to negotiate until they ask.

The mistake that burns your cash

Later in the talk, Touker turned to a problem he sees repeatedly.

Founders raise money and immediately pour large sums into Meta and Google ads without knowing the true return.

He said that too many businesses treat paid traffic as a shortcut, then discover later that most of the spend went nowhere.

He encouraged the room to look for routes that travel further without draining budgets.

Think influencers, collaborations, and creative ideas that spread because they’re interesting, not because you paid for reach.

It wasn’t anti-marketing, but a reminder to protect your cash when conditions are tough and attention is expensive.

What time in the game teaches you

Touker Suleyman has lived through decades of good markets and bad ones. The message he delivered wasn’t loud or glamorous, but it was the one founders needed to hear.

The hardest setbacks usually pass. The ones that linger are the avoidable commitments and the unnecessary spending that creeps up when you’re moving fast.

So before you sign something new or double your ad budget, take a moment to ask yourself:

Do I understand every liability with my name on it?

And am I investing in growth or just fuelling a habit?

If those answers aren’t clear, pause. Your future self will thank you.

An office move sits at the crossroads of cost, culture, and leadership. Get it wrong and you trap yourself in the wrong space… or the wrong pace. Get it right and your team can finally breathe.

Speaking with Joe Averill, founder of Level Workspace, made one thing clear: too many founders rush leases, over-buy space, or treat the move as a vanity upgrade instead of a strategic one.

Here are the three questions every founder should ask before signing anything. 👇🏻

1️⃣ How much space does growth really need?

Joe’s seen founders double headcount within 18 months and get trapped in long-term leases that suffocate their flexibility.

It’s easy to equate more desks with progress. The smarter move is to think in phases.

Could you start smaller, then expand within the same building? Can rent scale with actual headcount? Are there options to add or release space without painful penalties?

The goal is to stay nimble while your company finds its rhythm.

2️⃣ What’s your office really for?

Most founders still budget for a desk per person. Joe tells them to stop. “If you’ve got fifty people, you probably only need twenty desks,” he said.

“Buildings now come with breakout areas, cafés, and auditoriums. You can bring everyone together once a month without paying for dead space.”

This shift forces a deeper question: what is the office for?

If your team mostly collaborates remotely, the space’s job isn’t to host everyone, but to host moments, whether it’s planning sessions, town halls, or team bonding.

Think about how the environment makes people feel. Are there spaces for deep work and spontaneous chat? Does it match how your team actually operates, not how you wish they did?

3️⃣ What’s the real cost of being here?

Every owner knows the headline rent. Few know what the deal truly costs.

Joe calls the process “a minefield”. Hidden clauses, service charges, dilapidations, maintenance, connectivity, insurance… the list adds up. “Most people don’t know what they don’t know until they’re halfway through the process,” he said.

Before touring anything, ask yourself:

• Do we understand the total cost over three to five years?

• Who owns the relationship with the landlord, and who’s advising us?

• Are we clear on exit options if the business changes?

The right deal protects your cash and your focus. The wrong one will quietly drain both.

Your office is a mirror of your mindset

As Joe talked about his own journey, he said: “You’ve got to back yourself and believe in yourself, because in times of turbulence, that’s all you have.”

That’s why an office move is a statement of intent. It tells your team who you are and what you expect.

It’s the first thing clients and new hires see, and the quiet reminder of what you’re building.

Choose a space that mirrors the business you’re growing into, not the one you’re outgrowing.

Before you sign

Your first office proved you could start.

Your next one proves you can scale.

So before you fall in love with the view or the postcode, pause on these three questions:

• Does it flex with your future?

• Does it bring people together for the right reasons?

• And does the deal truly serve you, or slowly trap you?

If the answers aren’t clear, you’re not ready to sign.

More office life from Millennial Masters:

James Fleming told me: “People go on these leadership programmes, get a nice certificate, go back to work on Monday… and nothing’s changed.”

He’s right. We don’t learn because someone tells us what to do, we learn when a story makes us see something new.

That’s been on my mind all week because it’s exactly why I started Millennial Masters.

I want to know how people got there: the choices, the doubts, the contradictions and the parts they don’t usually talk about.

When someone shares their story, you start to understand the world through experience, and that’s what actually changes people.

Here’s why stories teach you what self-help never can. 👇🏻

Stories change behaviour

When I interview founders, I usually ask which books shaped them. The answers aren’t what you’d expect.

More often they mention a biography or a novel, with stories about people who failed, adapted, and found their way through chaos.

Joshua Western told me he’s read the standard founder canon and found most of it “s**t.” What inspires him are autobiographies and political biographies that reveal character and context.

Jack Good said biographies let him “live that person’s life and think their thoughts,” which is why he reaches for Jobs, Musk, even House of Gucci.

Liam White pointed to Shoe Dog. It is the Nike brand story, but also a collection of hard realities. You come away with a feel for cash crunches and bets that nearly broke the company, which is what most advice glides past.

Oliver Yonchev traced a pivotal spark to the Innocent founders’ story. That book gave him a model for purpose and product that he could test against his own decisions.

William Stokes listens to founder memoirs and life stories on long drives. He mentioned Matthew McConaughey’s book, where the actor shares life lessons and stories from his journey.

Founders keep coming back to the same truth: stories make things real.

Fiction sharpens judgement

Fiction kept coming up in my interviews with Millennial Masters, often with a quiet confidence.

Yehong Zhu recommends it to founders who want more original ideas, alongside timeless Stoic wisdom from Marcus Aurelius and Epictetus.

Rob Smith keeps The Obstacle Is the Way on his shelf for the narrative of setbacks turning into strength.

Andrew Steele drew a personal thesis from Steinbeck’s East of Eden about giving yourself permission to try.

Tom Wallace-Smith said NASA scientists were starstruck by the Star Trek writers because storytelling can frame high-stakes ideas better than a technical brief.

Archie Mackintosh ends his day with stories that switch his brain off; not business, just human stuff.

Ryan Carruthers admitted he used to comb Wikipedia biographies of entrepreneurs to see how they started. Most origin stories were messy. That observation alone reduces the shame of imperfect beginnings.

The real education is in stories

That is why Millennial Masters focuses on journeys. You learn more from the choices, doubts and contradictions than from any tidy framework.

If you want to learn like the people I interview, start collecting stories.

Read biographies that show what decisions cost. Listen to founder podcasts that don’t skip the messy bits. Queue an audiobook that lets you sit inside someone else’s head for a few hours.

Stories stay with you because they make knowledge feel real. They shape how you see and decide, and over time, they turn information into understanding.

More insights from Millennial Masters: