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.
If investors already know your name, you do not walk in cold.
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
This captures something most fundraising advice glosses over: the compound interest of reputation.
Great tangible tips and advice for founders looking to raise capital!