Harry Stebbings on Mindset, Systems, and Outlier Results
The ideas in this conversation will shape how you build and invest. They did for me.
I listen to podcasts every week and have done so for more than ten years. It is very rare to find an episode that stays with you for days. This one did.
In this conversation, Wouter Teunissen sits down with Harry Stebbings, the creator of 20VC, and the depth of the exchange surprised me.
Harry launched 20VC from his childhood bedroom at age eighteen. Within a few years, he turned it into the most influential podcast in venture capital, a place where the world’s top founders and investors go to share how they think, decide, and build. That audience eventually became the foundation for 20VC Fund, which has now raised more than $800 million to back early-stage companies.
Harry’s reach is enormous. Every major investor has been on his show. Every decacorn founder knows who he is. Yet in this interview, he opened up in a way I had never heard from him before. Each sentence felt like a masterclass. It felt like listening to someone who has studied the psychology, systems, and reality of building at the highest level and is finally ready to say the quiet part out loud.
I listened to the entire episode twice in the last three days. That is how dense and powerful it is. Many of the ideas he shared are lessons I am already using, and others will shape how I operate for years.
I respected Harry before this. After listening to this conversation, that respect reached a different level…
And now, I’m sharing the 18 most powerful moments and learnings from the podcast:
1. The Psychological Profile of Every Decacorn Founder
After interviewing almost every $10B+ founder, Harry noticed something disturbing.
They all have the same two traits: a superiority complex where they inherently believe they are better, more capable, able to do what others can’t, and simultaneously a deep inferiority complex where they constantly feel they’re not moving fast enough, not achieving what they should be.
Harry says: “It’s this deep masochism or sadism towards themselves, which is deeply psychologically scarring. But it drives you to be better and better. I sadly have both in spades. And I think really it’s just a lack of self-love in any way.”
This isn’t motivational, it’s clinical, and you’re always better than everyone else yet never good enough for yourself.
This isn’t sustainable and it’s not healthy, but it’s what separates $10B outcomes from $100M outcomes, and if you recognize these traits in yourself, understand that this is your competitive advantage and your Achilles heel.
The founders who win channel this into systems, not burnout.
2. Why Harry Cuts 30% of Every Podcast Episode
This one shocked me.
Harry removes 30% of every single episode, and not because the content is bad, but because it’s not exceptional enough to make the final cut.
“Would you ever let your product be released if 30% of it was meh? Can you imagine if Sam Altman came out and said, 30% of the GPT is meh, but 70 is pretty good. You don’t ship it.”
Most people ship “good enough” and they have “good enough” follow-ups, “good enough” emails, “good enough” preparation, but Harry understands that every interaction is product and every sentence in his podcast, every email he sends, every meeting he takes needs to be exceptional or it gets cut.
Before you send that email, ask yourself if every sentence is valuable, and before you ship that feature, ask if you’d be embarrassed if this was the only thing you’re remembered for.
Mediocrity is a choice hidden in efficiency.
3. “Moderation Is Largely for Cowards”
When Harry was 16, he saw a girl at school and thought she was the most beautiful thing in the world, but he weighed 125 kilos.
So he decided to lose weight.
“Anything that I do, I will overdo. I think moderation is largely for cowards. I hit the gym very hard and stopped eating, and within five months I lost 40 to 50 kilos.”
He went from 125kg to 75kg in 5 months, and this isn’t a health recommendation but a window into the psychology of extremity.
Elon sleeps at the factory, Jensen Huang works 7 days a week, Brian Chesky reviews every detail, and the people who build legendary companies don’t do moderation but rather obsession with guardrails.
Find the thing that makes you willing to go to extremes, then build systems so extremity doesn’t destroy you.
4. Your Mind Gives Up Before Your Body Does
Harry runs 100-mile ultramarathons and his knees are those of a 90-year-old and he has severe psoriasis, but he still runs.
“Your mind always gives up before your body does. If I can control my mind, there is nothing that my body cannot do.”
Physical suffering is training for mental endurance, and when you run 100 miles with destroyed knees, you’re not training your body but training your mind to override the voice that says “quit.”
Fundraising is painful, rejections are painful, pivots are painful, layoffs are painful, and the founders who win aren’t less afraid but have just trained their minds to override the quit signal.
You don’t need to run ultramarathons, but find something that teaches you that discomfort is temporary and you control the shutdown switch.
5. How Harry Raised $800M (The LP Relationship System)
This system is insane.
Harry speaks to 2 LPs every single week, even when he’s not fundraising, and at the end of every call he asks: “Who are three people you love to hang out with that you think I should spend time with?”
That’s 2 calls times 3 introductions equals 6 new relationships every week, which equals 312 per year, and he keeps a CRM of 400 LPs.
Every quarter, he sends personalized updates with specific details about their lives: “Hey, I hope your parents are still enjoying Amsterdam. I loved going with my mother last time we did the marathon there.”
The results speak for themselves: he raised $8M, then $140M in just 7 days, then $400M in 3 months, and $75M of that was raised on WhatsApp.
“The conversion rate is so, so high when you let them follow your journey across time. It’s not just, hey, we’re fundraising.”
90% of VCs fail at fundraising because they only talk to LPs when they need money, but if you build relationships when you don’t need them, when you do need them it’s a 7-day raise instead of a 7-month one.
6. Never Run Out of Capital (Or You Lose Forever)
“People fail in this business because they run out of capital supply. They get a chance to do $100 million into OpenAI and they’ve got 12 hours for it and they don’t have $100 million. My job is to make sure we never run out of money when great opportunities come.”
The best deals happen on the worst timelines, like getting 12 hours to decide on OpenAI or 24 hours to lead the next Stripe’s seed round, and if you don’t have capital available, you lose the opportunity forever.
Replace “capital” with “optionality” and the principle applies everywhere: founders need runway to say no to bad deals, operators need savings to leave a comfortable job for a risky bet, creators need attention to launch something new.
Always keep your “option tank” full so when the exceptional opportunity appears, you can act.
7. Fuck Visions (Why Harry Doesn’t Believe in Long-Term Planning)
This one is so contrarian.
“I think visions are one of the most dangerous things. We’re always told you should have a vision. Fuck visions. It’s so damaging. When I started, if I had accepted my vision, I would have capped my potential so much. Visions set these artificial ceilings on your potential.”
Every startup book tells you to start with the vision, but Harry says visions are ceilings disguised as inspiration.
“You should be micro-ambitious. Chase very close targets with incredible fervor and not have this ridiculous vision. Every year my vision unlocks a completely new layer that I never anticipated.”
Harry never envisioned raising $800M but focused on getting one great guest, he never envisioned Project A but focused on being valuable to founders, he never envisioned being a top 3 VC podcast but focused on cutting boring content.
Don’t ask “Where do I want to be in 10 years?” but instead ask “What’s the most ambitious thing I can accomplish in the next 90 days?” because micro-ambitions stack and each one reveals a new ceiling you couldn’t see before.
8. When Choosing Between Two Options, Pick the One That Opens More Doors
“When you’re faced with two options, choose the option that has a higher chance of opening another door. You’ve got two options tonight: you can rest up at home and have that delivery and chill out. Or you can go to that drinks party that may not lead to something, but you don’t know. It’s a pain and you’re tired. But it could also have that person that changes your career.”
If you choose the door-opening option 80% of the time over 365 days, you create 292 chances for serendipity versus just 73, and luck isn’t random but a surface area you intentionally expand.
Tonight you decide: stay home or go to the event, this weekend: Netflix or reach out to that person, this month: comfortable path or uncomfortable growth.
Choose the door.
9. Never Wait Until Tomorrow to Send the Email
This changes everything.
“After that dinner I will literally in my head visualize the table. I will go around and I will email each one personally: ‘It was so great to see you tonight. I’m so pleased that Max is enjoying Imperial.’ I do it that night. Never do it the next day.”
It shows them you’re on it and it’s fresh in their mind, and here’s the kicker: “90% of people don’t actually do it the next day. Something happens. It’s a busy day.”
He visualizes the table after the event, writes a personalized email to each person, and does it in the Uber home, never tomorrow, and sometimes it can be a copy and paste where you just make the first line personalized.
Action delayed is action diminished, and the person who executes tonight beats the person who plans for tomorrow.
10. How Harry Cold Emails (The 53-Email Strategy)
Harry emailed Mark Benioff 53 times, once every single week, and every time he would A/B test different personalizations: his favorite drink, his holiday home, his favorite holiday destination, Salesforce quarterly results, absolutely relentlessly never giving up.
Here’s the exact formula he uses:
Clear subject line like “20VC Podcast Appearance” (not clever, just clear), and never say “I hope you’re well” because everyone says this and it’s meaningless, instead say “Hi Mark. Keeping short out of respect for your time.”
State your objective immediately: “I would love to have you on 20VC,” add social proof like “We have X subscribers and I’ve had guests like Y and Z,” make a clear commitment: “We simply require 30 minutes of time and it’s done on Riverside,” and add a personalized PS: “If you do it, I’ll send you a bottle of your favorite Macallan 75.”
He uses LLMs to research: “What are five things very few people know about Mark Benioff that would really impress him at a layer of personalization that not many people engage with?” and then puts it in the PS.
Most people quit after 2 emails, but Harry sent 53 with different angles each time, and eventually persistence becomes impressive.
11. The Best Founders Make You Feel Uncomfortable
“Peter Fenton taught me that the very best founders make you feel incredibly uncomfortable. The intensity with which they bring their energy is just very, very tangible. I think that’s the same for fund managers. I’m not sure that I make all of my LPs feel comfortable. That’s not your job. But they definitely feel the intensity.”
If everyone feels comfortable around you, you’re not intense enough to build something legendary, and uncomfortable doesn’t mean being an asshole but rather being a force of energy that demands excellence and makes comfort impossible.
Do investors feel your intensity in pitches, do employees feel your intensity in meetings, do partners feel your intensity in negotiations?
The best founders don’t make you feel at ease but make you feel like you need to match their energy or get out of the way.
12. The Only Thing That Matters in Venture (According to Doug Leone)
“I’ll never forget Doug Leone from Sequoia telling me that the only thing that matters in venture capital is finding the very best founders before anyone else. And that’s why Sequoia will always do pre-seed investing.”
Find the best [X] before anyone else: founders for VCs, engineers for CTOs, customers for salespeople, ideas for writers.
If you find them after everyone else, you’re competing on price and not relationship, but if you find them before, you’re the obvious choice.
Where are you looking that others aren’t?
13. The North Star Metric (Everything Else Is Distraction)
“The most important thing for any business is to understand the north star metric from which everything else cascades. The north star metric for the fund is: we must find the best founders in the world and make them want our money. That’s it. If we do that, everything else works. The best companies really don’t need you.”
For 20VC Fund, best founders choosing them equals everything working, and for 20VC Media, best guests equals audience growth equals more guests equals more revenue, and for your business you need to figure out what is the one metric that cascades everything else.
The most common mistake is confusing activity metrics like meetings held and emails sent with the north star metric like best founders choosing you.
Every week, ask yourself: “Did this activity drive the north star metric?” and if the answer is no, stop doing it.
14. My Favorite Lesson: It’s Not What You Say, It’s How You Make People Feel
Harry’s grandfather was a hotel manager and he taught Harry something that changed everything:
“It’s not what you say, it’s not what you do, but it’s how you make people feel. When they come into my hotel, they have to feel like it’s a home just like their real home.”
Harry applies this to every interaction, making people feel heard, making them feel safe, making them feel like they’re the smartest person in the room.
People don’t remember what you said in the meeting but they remember how they felt during it, and this is why founders take his calls, this is why LPs invest, this is why guests say yes, not because of what he says but because of how he makes them feel.
15. Why Having Bulimia Led to Building a $800M Fund
“When I had bulimia, I don’t think I would have my life at all if I didn’t have bulimia. I had bulimia when I was kicked out of this school. Because I was kicked out, I had to go to this other school where they only had two hours of lessons a day. Because I only had two hours of lessons a day, I had all of this free time. Why don’t I start that podcast I’ve been wanting to start?”
The chain reaction went: Bulimia led to getting kicked out of school, which led to a new school with 2-hour days, which created free time, which led to starting 20VC, which built into a $800M fund.
“The greatest challenges can lead to the greatest opportunities if you let them.”
Your struggles aren’t obstacles to success but often the unlock, like how Airbnb was born because founders couldn’t pay rent or how WhatsApp was built because Jan Koum grew up poor and hated ads.
Constraint leads to creativity leads to competitive advantage.
What struggle are you currently facing that could be the unlock for your biggest opportunity?
16. Everyone Is Fucked Up (Give Them More Patience)
“When someone is unreasonably different from how you thought, most often it has nothing to do with you. Actually everyone is fucked up in their own way. We’ve all got cracks and we’ve all got our insecurities and flaws. Give people more patience than one would initially give them. Because you have no idea what they’re going through.”
When someone is short with you or drops the ball, your first instinct is “They don’t respect me,” but the truth is they’re probably dealing with something you can’t see.
The person who extends patience when others don’t builds loyalty, and before you get angry, ask yourself: “What might they be going through that I can’t see?”
People remember who was kind when they were struggling.
17. Culture Is Winning (Why Revolut Doesn’t Have Free Lunch)
This one is controversial.
“I think we spend far too much time on culture. Culture is, for me, winning. People are fundamentally driven by development and growth. That is the number one driver of human happiness. That happens in companies that win. You know what culture wins? Revolut. Revolut does not have a culture. It wins. And that’s all that fucking matters.”
Ping pong tables don’t create culture, winning creates culture, and most startups focus on free lunch, team offsites, and “culture decks,” but people are miserable because the company isn’t winning.
The real drivers of happiness at work are: Am I learning, am I growing, are we winning, and if yes to all three, culture takes care of itself.
Revolut is famous for being “brutal” yet people want to work there because they’re winning, and winning feels better than free lunch.
“One of the biggest challenges with a lot of people is they’ve never won. So they don’t know how good it feels to win.”
Stop optimizing for comfort and start optimizing for wins.
18. The Tokyo Test (How Harry Decides Who to Hire)
“It’s the Tokyo test. You have to fly to Tokyo with them and on that flight you have to be engaged and entertained enough for the entire flight. The marathon is a wonderful thing. I walk a marathon every weekend with my mother. And I do it for hires and investments. Because after an amount of time, the facade drops. You can only uphold that persona for an hour, for two hours, for three hours. You’re going to be walking for six and a half hours.”
Instead of doing 3 interviews plus reference checks, do a 6.5-hour activity together, because in hour 1 they’re performing, in hour 2 they’re still holding it together, in hour 3 the facade starts cracking, and in hours 4 through 6 you meet the real person.
Harry walks marathons with potential hires, walks marathons with founders before investing, walks marathons with his mother (because by age 18, you’ve spent 92% of the time you’ll ever spend with your parents).
Time reveals character, and the longer the exposure, the more accurate your assessment, because the person who seems perfect in a 1-hour interview might be unbearable on a 6-hour flight.
What Harry Makes Impossible to Ignore
After going through these 18 lessons, one thing becomes clear. Harry operates with a level of intensity and consistency that very few people can sustain. His psychology, his routines, and the way he applies pressure to himself create a compounding effect that eventually becomes impossible to compete with.
He does the work that others postpone. He builds the systems that others avoid. He pushes into discomfort long after most people pull back. And he does all of this with a level of intentionality that turns habits into leverage.
This is what creates outliers!
What I Am Putting Into Practice
I’m applying the lessons that stood out most.
The email rule where the follow-up happens the same night.
The focus on one clear North Star metric.
Choosing the option that opens more doors.
Building relationships long before you need them.
Spending more time with people before making decisions.
None of this is complicated. It simply requires a level of presence and discipline that most people never commit to.
Harry chose that path. And the results speak for themselves.
Here is the full interview that inspired all of this. It is worth every minute :)
👉 Listen to the full conversation between Harry Stebbings and Wouter Teunissen
Excellent interpretation, Great!
Firstly, just know I do not say these things in a mean spirited way. I wish only the best for these people. Okay.
An alternative title this could be called 18 lessons on how to not live ones life.
It's pretty clear from this that Harry (and all these Deca founders they discuss) lead miserable lives. These are people not so much deserving of respect as they are of pity.
If you can live your life any other way from these people I implore you to do so. If you cannot. If you are someone who saw the movie Whiplash and thought, what an inspirational tale I think I'll go that route, seek out help. If upon receiving therapy you still cannot help but to go this route, I hope you find the fortune you seek. You'll still be miserable but at least you'll be miserable with money. However, a warning, there is a strong presence of survivor ship bias in the examples we see and just because the ultra wealthy have these traits doesn't mean there aren't 1000 others for everyone one of them that also have these traits, and who are also miserable, but in addition are broke because they failed. You don't hear from them on podcasts.