Do achieving career milestones and hitting goals produce lasting fulfillment for founders?

Sebastian Siemiatkowski · Mar 1, 2021

Striving for excellence in whatever you do, regardless of the field, produces deep fulfilment, learning and happiness

He experiences that fulfilment himself from the pursuit of excellence and hopes his children will too

Scope: field-agnostic — the domain doesn't matter, only the striving

30:38 20VC: Klarna Founder Sebastian Siemiatkowski on Scaling Europe's Most Valuable Private Tech Company, How To Motivate and Challenge Your Team Most Effectively & The Biggest Lessons From Working with Mike Moritz

Eiso Kant · Oct 7, 2024

Reaching the outcome you're chasing is never the interesting moment — the goal is always moving, so the value is in the daily work with the people

Outcomes are part of the obsession that makes you want to build, but the goalpost always moves; the experience comes from picking the hardest possible problem and doing it with great people

64:12 20VC: Raising $500M To Compete in the Race for AGI | Will Scaling Laws Continue: Is Access to Compute Everything | Will Nvidia Continue To Dominate | The Biggest Bottlenecks in the Race for AGI with Eiso Kant, CTO @ Poolside

Severin Hacker · May 19, 2025 · hedged

Success has made him somewhat happier, driven mostly by a durable sense of achievement rather than money

The sense of having tried and had it work will never go away even if Duolingo collapsed tomorrow; moments like seeing a stranger use Duolingo on a Venice water bus are what land

Scope: says he was already fairly happy in his twenties; hard to disentangle money from success and self-knowledge

81:58 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Fernando Fanton · Jul 27, 2025

The value in a career comes from growing through difficulty, not from hitting milestones — most people around him vehemently disagree with this

When he joined Microsoft he thought he had made it and nobody cared afterwards; the things you thought were important are forgotten quickly, while health, friendships and family endure because you never know what will happen

Scope: accepts the lesson is unlearnable when young and irrelevant once old, so people may not follow it

63:58 20Product: Should We Kill the PM Role Entirely | How Does Product Design Change Most in a World of AI | How Do Monzo Build Product Today: What Works, What Does Not | Why Most Product Sucks and What Makes Truly Great Product

Parker Conrad · Apr 26, 2021

The thing that ends up mattering most in building companies is working with a set of people you genuinely enjoy spending time with

Looking back across three startups, the experiences he most enjoyed were about the people; his biggest wins at Rippling have been bringing in people he was excited to work with and his biggest disappointments have been those who turned him down

Scope: personal retrospective across his own career

29:13 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"

Parker Conrad · Apr 26, 2021

The lesson he most wishes he'd known at the start is that working with people you enjoy spending time with is the most important thing

Despite sounding like a cliche, those relationships have been the most fun and most important part of his last ten to fifteen years in his career

Scope: acknowledges it sounds like a cliche

33:50 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"

Mike Cannon-Brookes · Oct 13, 2025

If you don't enjoy the people you work with, nothing else about the founder journey matters — and it's the founder's job to ensure there is no seat at the company dinner table they wouldn't want to sit in

All technology is built by people; the joy and lasting memories come from the team, not from the bank balance, which is only an external scoreboard

52:43 20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes

Tracy Lawrence · Jul 27, 2020

Building a company out of your own unhealed wounds is double-edged: it fuels a beautiful mission and culture, but it means failure of the company feels like failing your younger self

Her company's mission that nobody eats alone came from being bullied and eating lunch alone in the bathroom, which powered the culture but also fused her identity to the outcome

Scope: drawn from her own case

23:18 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Harry Stebbings · May 19, 2025

When a founder's identity is tied to their company, the company's performance determines their personal happiness — and that is a hard way to live

From his own experience: 20VC is the only job he's had, and when the fund or media company isn't doing well he gets depressed

77:31 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Severin Hacker · May 19, 2025 · hedged

Roughly half of founders who leave their company fall into depression because their identity was the company

Their identity is the company, so leaving removes it

Scope: based on founders he has personally talked to

77:47 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Miki Kuusi · Nov 28, 2022

Founders driven to build never feel they have 'made it' — every milestone reveals a bigger, steeper next mountain

He has reread passages like 'the struggle', firing an executive, demoting a loyal friend and wartime vs peacetime CEO each time he faced those situations

51:28 20VC: Wolt CEO, Miki Kuusi on Leadership Lessons Scaling to a Reported $8.1BN Exit to Doordash, Building Teams not Families, The Difference Between Trust and Safety Within Companies, How To Use Compensation to Create Culture & Why You Should Not Be Lookin

Harry Stebbings · Jun 6, 2025 · hedged

Fulfilment and hunger are close to mutually exclusive, so you never want to feel content

Like a dog, you want to stay always hungry; contentment would cost him ambition

Scope: 'I almost do' — he stops short of full certainty

80:54 20VC: The Science of Storytelling: Three Steps to Master the Perfect Story | From Near Death Experience to Unicorn Startup: The Untold Story of Omaze with Matt Pohlson

Peter Rahal · Aug 8, 2025 · hedged

An inability to ever be satisfied is on balance a blessing for a builder

It functions like an obsession or itch that produces an irrational sense of urgency

Scope: has to be kept in check; he hasn't done much introspective work on it

44:57 20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal

Roger Ehrenberg · Feb 19, 2024 · speculative

His next major milestone will come from building something — a seed investment becoming a wildly successful company or his Detroit economic development work — not from money-derived perks like owning sports teams

Sports team investments only came because he has money and people value him at the table, which isn't what motivates him

Scope: 'I'll know it when I feel it'; unsure which it will be

54:16 20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

Richard Socher · Apr 18, 2025

Success should be measured by positive impact significant enough that future people remember it — and being remembered only by the people in the know is enough

Most people can't name who invented penicillin or the cure for their cancer, yet those in the field know, and that suffices

55:35 20VC: Foundation Models: Who Wins & Who Loses | How Economies and Labour Markets Need to Change in a World of AI | China vs the US in an AI Race: What You Need to Know | Rich Socher, Founder @ You.com

Nick Frosst · Sep 1, 2025

Building something that outlasts you — a company, a work of art, an idea — is inherently human and rewarding, even though everything ultimately decays

Participating in the construction of something bigger than yourself is fundamentally human; both the reward and the eventual ruin are true at once

Scope: 'generational' means on the timescale of generations, not personal legacy; accepts that all such works eventually fall

45:39 20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

Jerry Colonna · Jul 27, 2020

The biggest misconception about mental health is that there is an achievable state in which everyone feels great and happy all the time

That myth actually exacerbates our search for mental well-being

Scope: applies to mental health in general, not just in tech

41:37 20VC: Brad Feld, Jerry Colonna and Tracy Lawrence on Depression and Mental Health, The Dangers of Tying Happiness To Milestones & Why Fear, Anxiety and Guilt Are Useless Emotions

Craig Courtemanche · Dec 4, 2023

The founder's story that someday the company reaches a state of nirvana is false, just as it is in marriage; both are a permanent slog that is hopefully net positive

Founders and newlyweds both tell themselves it will eventually be perfect, but neither story is ever true

60:24 20VC: From Construction Worker to Billionaire CEO; The 21-Year Epic Journey of Procore to an $8.6BN Company, Advice from Tobi at Shopify on Being a Great CEO & Why The Idea of "Becoming an Entrepreneur" is BS with Tooey Courtemanche

Harry Stebbings · Oct 2, 2023

The joy of the work is in the doing and in building relationships, not in the outputs, titles or trappings

He got lost when he focused on show outputs and realized the friendships are what he values

Scope: reflection on his own experience running the podcast

58:41 20VC: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help, The Most Important Signals to Assess When Meeting Founders & Why Kids Bring Less Happiness and More Joy with Phin Barnes @ TheGP

Phin Barnes · Oct 2, 2023

Focusing on the process and finding happiness and joy in it is the key, and outcomes take care of themselves

59:08 20VC: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help, The Most Important Signals to Assess When Meeting Founders & Why Kids Bring Less Happiness and More Joy with Phin Barnes @ TheGP

Sebastian Siemiatkowski · Mar 1, 2021

Money does meaningfully improve life because it removes a whole category of worry, and wealthy people who claim money doesn't make you happy have lost touch with normal life

He no longer worries about bills and can take his kids anywhere; that freedom is an immense thing that's easy to forget once you have it

Scope: retracting his earlier public answer that money doesn't make you happy; concedes happiness isn't entirely tied to your bank balance and money couldn't help with his father's problems

26:17 20VC: Klarna Founder Sebastian Siemiatkowski on Scaling Europe's Most Valuable Private Tech Company, How To Motivate and Challenge Your Team Most Effectively & The Biggest Lessons From Working with Mike Moritz

Roger Ehrenberg · Feb 19, 2024

Accruing significant wealth changed remarkably little about him beyond removing money worry; drive, humility and desire to learn are largely unchanged

He feels like the same person he was in 1987, is married to the same woman, and people with far less money have the same things he has

Scope: personal account

55:16 20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

Harry Stebbings · Aug 15, 2025

The most important thing in life is to run your own race rather than benchmark against others

Comparison to others can make you feel terrible or amazing arbitrarily

71:39 20VC: 15 Term Sheets in 7 Days and Choosing Benchmark | Harvey vs Legora: Who Wins Legal and How to Play When You Have $600M Less Funding | Are AI Models Plateauing Today | Building a 9-9-6 Culture From Stockholm with Max Junestrand

Max Altman · Nov 21, 2025

Venture is a dangerous environment for staying off the hedonic treadmill, and consciously resisting it matters both for personal happiness and for performance at work

You are constantly around people who have done extremely well, which makes it hard not to want more and more

Scope: describing his own situation being close in age to very wealthy peers

67:24 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Nigel Morris · May 24, 2021

Once you cross the 'f-you money' threshold, additional money stops mattering and nourishment has to come from relationships and coaching people rather than more zeros

Beyond basic Maslovian needs and financial escape velocity, whether a given investment does brilliantly or merely well no longer changes his life; helping people half his age navigate mistakes is higher up the hierarchy of needs

Scope: threshold is debatable, maybe $15-20M; speaking about his own fortunate position, not prescribing it for everybody

14:09 20VC: Why Bundling Does Not Work, How The Best Founders Analyse Unit Economics, Why The Way We Approach Mental Health in Venture and Startups is Wrong with Nigel Morris, Co-Founder & Managing Partner @ QED Investors

Harry Stebbings · May 19, 2025 · hedged

The happiness returns to wealth come in steps and plateau early — going from $10-20M to $100M changes very little in lived experience

At a couple of million you can live how you want but still need to work; at 10-20 you're comfortable with a nice house, and the extra 80 mostly buys jets

Scope: framed as his own personal ladder

81:33 20VC: Duolingo Co-Founder on Why $3M is Harder than $100M to Raise | Why You Should Always Take Tier 1 VCs Even at Worse Terms | Why Europe Can't Win Unless the US Screws Up | How AI Impacts the Future of Work and Education with Severin Hacker

Harry Stebbings · Nov 21, 2025

Of all the billionaires he knows, only one is happy

Scope: based on his own acquaintances

68:46 20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster

Avishai Abrahami · Jul 13, 2026

Happiness is not correlated with money or place, and the happiest people he has seen anywhere are in Brazil

He has observed happy people in many places regardless of wealth, which is why he can always tell himself the worst case is moving to Brazil

Scope: based on personal experience; disputes Finland's happiest-country ranking

47:20 20VC: Wix's Founder on What Wall St Gets Wrong About AI and Wix | Will Base44 Win the Vibe Coding Wars | The Truth About the Economics of Vibe-Coding | The Buyback Disaster: Lessons Learned with Avishai Abrahami

Roger Ehrenberg · Feb 19, 2024

Large windfalls mattered to him as durable validation of skill rather than as short-term joy or spending power

The first big bonus felt like proof he was valued and capable, and it changed something inside him — the same thing the TTD IPO later did

Scope: personal account

51:34 20VC: Why VC Returns Will Get Worse, Why LP Incentive Structures are so Broken, What is the Answer to Liquidity with No M&A or IPOs, When to Sell vs Hold Your Winners & Turning $5M into $250M with The Trade Desk | Roger Ehrenberg, Eberg Capital

Harry Stebbings · Jun 20, 2026

For a venture capitalist, self-worth is legitimately tied to financial outcomes because unlike other professions your performance is directly measured in money

A general's professional success doesn't correlate to their financial statement, but a VC's does — the clue is in the name

Scope: says he'd lose ~90% of his self-esteem if he lost 90% of his money

11:36 20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Brad Feld · Jul 27, 2020

After achieving a milestone people often hit a massive emotional down cycle, driven by exhaustion rather than unhappiness per se

You are exhausted by the time you get there

17:13 Post milestone crash is exhaustion not unhappiness

Jerry Colonna · Jul 27, 2020

The problem is not having goals — goals and milestones are good — the problem is making your worthiness of love, safety and belonging conditional on achieving them

Non-attachment is often misread as goallessness, but the trouble lies in the worthiness linkage

19:31 Goals are fine conditional worthiness is the problem

Tracy Lawrence · Jul 27, 2020

Selling the company doesn't resolve the underlying hyperachiever pattern; the achiever simply transfers identity to the next pursuit and keeps generating unhappiness and unworthiness

After selling her company her sense of worth attached to getting better at surfing, so a bad surf day now makes her feel unworthy

21:29 The achiever pattern simply transfers to the next goal

Nikesh Arora · Jun 22, 2026

You should not get hung up on where you'll be in one or five years; the right approach is to focus on finding something to enjoy each day and cultivating an optimistic, grateful state of mind.

The future is unknowable and, running a cybersecurity company, he has more than enough things to worry about — worry would put him in the wrong headspace, whereas state of mind is the thing he can actually control.

69:48 Drop the goal horizon and cultivate daily gratitude

Guillaume Moubeche · Dec 13, 2024

Money functions as chains on freedom in the modern world, and becoming financially independent forces existential questions most people never have to confront

Once he became financially independent and had a lot of cash, the obligation to earn disappeared and he had to ask what the meaning of his life and mission was, which pushed him toward spirituality

59:23 Financial independence forces existential questions about lifes meaning

Tom Blomfield · May 13, 2024

Achieving money and external success did not deliver the happiness he expected; letting go of the drive for external validation has been freeing and he is happier now than ever

He was raised to equate success in life with being rich, which drove him to build Monzo and stay long after he was happy; now that the drive has faded he has intellectually stimulating work plus hobbies and friends

58:24 Letting go of external validation after wealth brings real happiness

Matt Pohlson · Jun 6, 2025 · hedged

Founders can learn to separate their identity from company performance, though never completely

He used to tie his happiness 100% to company performance; he now cares about serving a mission bigger than any individual rather than his own identity

57:18 Founders can learn to partially separate identity from company performance by serving a larger mission

Matt Pohlson · Jun 6, 2025

You can be fulfilled and remain just as hungry — and you'll enjoy the pursuit more

He has changed his mind on this, crediting the Hoffman process

81:17 Fulfilment and hunger can coexist and enhance pursuit

Johannes Reck · Jun 23, 2025

Founders who get consumed by tech wealth and status won't be successful; Europe's most successful founders instead stay focused for long periods and reinvest their wealth into the startup ecosystem

That world doesn't bring joy or fulfilment — what does is seeing the next founder succeed

61:46 Seeing other founders succeed not personal wealth status is the source of fulfilment

Andrew Feldman · May 26, 2026

A CEO who does not take pride in making their team wealthy has no business being CEO and is not a real leader

Delivering for the team — 800 millionaires created at Cerebras, many of whom bet long stretches of their careers on him — is what should feel good every day

53:05 Making the team wealthy is the real source of satisfaction

Max Altman · Nov 21, 2025 · hedged

He would be less happy as a billionaire than he is now, and the billionaires who are happy are the ones who prioritized family

He would constantly want to upgrade — a nicer house, a boat — and comparison with even wealthier friends makes contentment very hard

68:57 Wealth fuels endless upgrading only family prioritizers stay happy