Scott Galloway’s been around the block. He’s founded nine companies, watched two fail, and built a second act that actually matters: media, money, and people paying attention.
Since moving from the US to London, he’s gone from founder with scars to podcast philosopher, with no-BS shows like The Prof G Pod and Pivot (with Kara Swisher), plus newsletters like No Mercy/No Malice and Prof G Markets.
“The old dawg” (as he refers to himself) is loud, sharp, flawed, and consistently worth listening to.
In recent years, he’s also stepped into a new space: rethinking what healthy masculinity, success, and resilience look like in an age where too many young men are stuck. He’s debated this twice with Steven Bartlett on Diary of a CEO, most recently after the Adolescence Netflix series, which, if I’m being honest, was overhyped. It lacked teeth and a good twist. Scott didn’t.
I’ve followed Prof G’s work for a while now. He’s always been transparent about the advantages that shaped him: being white, straight, and born in the right country at the right time (he’s 60). But he’s also clear-eyed, self-aware, and often painfully honest about what matters in the long run.
That’s why I picked his two most personal books for this Millennial Masters Booksmart edition. The Algebra of Happiness came out in 2019. The Algebra of Wealth followed in 2024. Together, they’re an attempt to answer two questions that matter to every millennial and Gen Z builder: What makes life worth it? And how do you build wealth without burning out or selling yourself short?
This Booksmart piece unpacks both: not just summarising the books, but pulling out the hard truths, smart strategies, and relevant lessons for our generation. I wish I’d read this earlier. I ignored what mattered, and burnt out fast. It’s not a lesson you want to learn the hard way, but most of us do.
Whether you’re scaling a business, building a career, or just trying to get a handle on what matters, this one’s for you. 👇🏻
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Let’s start with the thing people chase hardest but understand least: happiness.
The algebra of happiness
What really matters, and what people realise too late
Scott Galloway’s The Algebra of Happiness opens with a truth that punches through years of polished ambition: success isn’t a clean line. Most people chase grades and titles, then realise they don’t mean much.
For millennial and Gen Z professionals chasing big outcomes, this book is a reminder to zoom out. Galloway doesn’t pretend there’s a single formula. Instead, he offers brutal clarity on what builds a good life, and what doesn’t.
Resilience beats balance in your early years
One of Galloway’s strongest arguments is that “balance” is the wrong goal. That means pushing hard in your 20s, building credibility in your 30s, and buying freedom in your 40s. Comfort comes later, if you’ve earned it.
He doesn’t glamourise hustle. He just argues that discomfort early on buys you degrees of freedom later. The people with the happiest midlives? They leaned in hard during their career-building years. Galloway calls it “sweat equity,” and he treats it like compound interest: the sooner you start, the bigger the upside.
Avoid the mirage of prestige
A recurring theme is mistaking credentials for identity. Galloway tears into elite schools, brand signalling, and inflated egos built on proximity to power. He admits he bought into it all until life, failure and loss stripped it back.
His point is sharp: likes, logos and job titles don’t make you like your life. It’s a trap that costs years.
Invest in deep connections
Love, family, and enduring friendships deliver the greatest returns. That’s not sentimentality, it’s strategy. Galloway argues that intimacy is the strongest predictor of long-term happiness, and that too many people wake up wealthy but alone.
He’s not offering relationship hacks, but telling ambitious readers to start treating relationships as seriously as business. Call your parents. Spend time with people who don’t need anything from you. Choose a partner who energises you. Nothing else will matter as much.
Know when to quit
Ambition can turn toxic when it becomes inertia. Galloway describes moments when he stuck with companies, cities, or relationships too long out of pride or fear. His advice: quitting isn’t failure. Sometimes it’s the most rational move you can make.
And for entrepreneurs, this hits hard: success isn’t always persistence. It’s judgement. Learn when to walk, not just when to double down.
Don’t confuse intensity for depth
In the chase for big wins, many people ignore the slow, unsexy work of showing up. Galloway writes about being present at school drop-offs, calling friends back, visiting ageing parents. None of it goes on your LinkedIn. But it’s what life’s made of.
The algebra of happiness takeaway? Some of the most powerful decisions you make won’t show up on LinkedIn. Make them anyway.
Now let’s turn to the part everyone wants but few actually secure: lasting wealth.
The algebra of wealth
A playbook for getting rich (slowly)
Galloway doesn’t romanticise in The Algebra of Wealth. He reduces it to its essence: “Wealth is independence.” Not yachts, not watches; time, security, and the ability to say no. That’s the baseline. And unlike a lot of financial advice dressed up in mysticism, this is brutally simple: build character, pick a lane, play the long game.
Character before capital
Most people think wealth starts with the right stock pick. Galloway disagrees. He starts with discipline, grit, and delayed gratification. His point? You can’t build wealth if you don’t have the character to stick with boring things for a long time.
He lays it out plainly: “What we do is an expression of who we are.” Which means your habits (what you do when no one’s watching) shape your financial future. Want more money? Show up, consistently, to things that compound: work, saving, learning. Especially when it’s hard. Most people don’t have a money problem. They have a patience problem.
Pick a wave early
Galloway doesn’t tell you to follow your passion. He says to follow your talent, and then pick an industry where the tide is rising. He calls it ‘getting on a wave.’ Join a sector before it gets hot, and stay put. You don’t need to invent the wave. You just need to ride it early and stick around.
That’s how you build equity. People chasing quick wins burn out. People who get good at something useful, in a growth industry, quietly become rich.
He’s blunt: stamina is more important than genius. The winners aren’t always the smartest, they’re the ones who stay in the game. The longer you stay, the more asymmetric the rewards.
Sweat equity > stock picks
Wealth doesn’t come from being clever with money. It comes from owning part of something that grows. That means equity and ideally, equity you earned by building something, not just buying in.
Galloway’s framework is clear:
Get good at something hard.
Work somewhere with upside.
Buy ownership where you can — shares, property, side ventures.
Don’t sell when you’re bored. Sell when you have options.
He calls out the bullshit: crypto gambling, influencer culture, and short-term plays. The maths rarely adds up. Instead, he’s preaching slow compounding over sudden jackpots. The key to wealth he argues is to own something that increases in value while you sleep.
Don’t spend like you’re rich
Here’s one of Galloway’s most uncomfortable truths: many people look rich but aren’t. They lease the car, wear the brand, take the photo, but they’re drowning in debt. That’s not financial independence. That’s theatre.
His fix? Spend less than you make, always. And be aggressively boring with your money. Index funds, high savings rates, and low overheads don’t look sexy on Instagram. But they work. And they buy you freedom.
This is about choosing what you value. Galloway argues that the ability to delay consumption is one of the strongest predictors of long-term wealth. And he practises what he preaches. He made his first million in his mid-thirties, not by chasing status, but by saying no to lifestyle inflation.
Avoid lifestyle traps
Every time your income increases, there’s a moment of danger. Do you upgrade your life, or upgrade your savings? Galloway says the second choice is where wealth lives.
“Nothing is ever as good or as bad as it seems,” he says, and this goes for pay rises too. Your life doesn’t get meaningfully better because your sofa is more expensive. It gets better when you stop worrying about money altogether.
His solution? Automate savings. Cap your fixed costs. And get clear on what actually brings you joy, then spend on that, not everything.
What this means for founders and builders
If you’re building a business, Galloway’s message is clear: prioritise ownership and resilience. Don’t give away too much equity too fast. Avoid founder martyrdom: looking busy doesn’t build leverage. Making smart choices early does. The win is owning your time. Not having your inbox run your life.
And if you’re early in your career, prestige fades. Reps build something that lasts. Stay in the game long enough to get good. Pick the right wave. Then ride it with discipline and focus while others get distracted.
Cash buys time. Energy builds empires.
Scott Galloway didn’t write self-help books. He wrote the manual no-one gave you. The lesson? Don’t confuse movement with momentum. Hustling without direction isn’t strategy, it’s noise.
Galloway makes it clear: real success is stacking good decisions, not chasing perfection. The happiest people aren’t the ones who avoid pain. They’re the ones who build resilience and clarity through it.
Wealth, on the other hand, isn’t about luck or genius. It’s about focus, time, and owning something valuable. It’s skipping the status game and playing the long one. Own something real. Spend time where it counts.
For Millennial and Gen Z founders navigating economic volatility, burnout culture, and the pressure to be everything, Galloway’s two books offer something rare: clear maths, grounded advice, and a reality check.
Your twenties and thirties don’t need to be optimised into oblivion. They need to be built on a few things that matter: character, craft, control, and care.
Happiness is energy. Wealth is time. Build both now, or you’ll be chasing them forever.
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