Harry Stebbings is the future of Venture. Here 10 things you should learn from him
My full notes from Harry Stebbings interview by Wouter Teunissen
(My notes from a full weekend studying Harry Stebbings’ Biography Podcast interview)
I spent the whole weekend studying Harry Stebbings‘s interview by Wouter Teunissen. It’s the most honest and value packed interview I’ve ever watched in business.
Harry is undoubtedly one of the most driven, ambitious and relentless venture capitalists in the world and after watching this interview I can only think he’s still early & I can’t wait to see what he’s going to be able to build in the next 5 years.
I broke down (for myself) the most practical insights of the interview.
This is so valuable I didn’t want to share it, but here it goes:
1. The Psychological Profile of Decacorn Founders
Harry has interviewed almost every $10B+ founder on earth — and he says they all share three traits:
1. A superiority complex
They fundamentally believe they are better. More capable. Able to do what others can’t.
2. A deep inferiority complex at the same time
This one is almost painful:
They constantly feel they’re not doing enough, not moving fast enough, not achieving what they should.
3. A form of masochism
Not in the weird sense — in the sense that they push themselves so hard it leaves scars.
But it’s the engine that keeps them improving.
And Harry openly says he has all three.
That’s why this interview was so brutally honest.
2. LP Discipline: Speak to 2 LPs Every Week (Even When Not Raising)
This one is insane.
Harry speaks to:
✔ 2 LPs every week, even between fundraises
✔ Always ends the call with: “Who do you think I should spend time with?”
✔ Keeps a CRM of 400 LPs
✔ Sends quarterly updates to all of them
✔ Writes hundreds of personalized notes in one day
This is how he raised:
$8M → $140M → $400M
Sometimes in days, not months
Sometimes $75M raised on WhatsApp
But it only works if the relationships are built over years — not when you suddenly need money.
3. When Choosing Between Two Options, Take the One That Opens More Options Later
This one is so simple and so good:
Pick the option that increases the probability of another option opening.
Stay home vs go to the event.
Rest vs meet someone.
Comfort vs surface area of luck.
It applies to everything.
4. Don’t Wait Until Tomorrow to Send the Email
After a dinner with 12 people, he will:
Visualize the table
Email each person personally
Do it in the Uber home
Never the next day
Because:
It shows intensity
It shows you’re “on it”
And 90% of people never do it the next day
5. How Harry Cold Emails (the exact formula)
This one is gold because it’s exactly how he built 20VC at 18.
Rule #1: Clear subject line
→ “20VC Podcast Appearance”
Rule #2: Never say “I hope this email finds you well.”
Rule #3: State your objective immediately.
Example:
That’s it.
Simple. Direct. High-conviction.
6. How to Invest at Pre-Seed or Seed
Harry’s view is extremely pure and extremely rare:
Only the founder matters. Nothing else.
Not:
Market
Product
Early traction
Deck quality
TAM slides
Just:
1. Founder quality
2. Complete unhinged-ness
3. Obsession that makes people uncomfortable
He said his biggest mistakes were:
Saying no to Vanta
Saying no to Deel
Because he didn’t like the market
But the founder was right in front of him.
7. Why Being an Interviewer Makes You a Better Investor
This part is fascinating.
Harry explains interviewing gives you:
1. The ability to make people comfortable enough to tell you anything
It takes 3–5 minutes.
2. You learn to bring your own vulnerability first
Talk about your own trauma, your mistakes, your failures — then they open.
3. Ask for advice
This instantly places the other person in a position of superiority
→ they become far more open.
And this skill transfers directly to evaluating founders.
8. My Favorite Lesson from Harry: Never Brainstorm. Just Go.
Never brainstorm.
Go, learn, iterate.
The speed of iteration is everything.
“Speed gives you more at-bats.”
“Activity drives outcomes.”
“It’s not speed — it’s velocity.”
And he hates when people sit in a room and try to “figure it out.”
You figure it out by moving.
9. How to Increase Your Surface Area of Luck
Harry intentionally designs his life to create luck.
Three concrete examples:
A. Interview decacorn founders weekly
At the end of every interview he asks:
→ “Who’s an incredible hidden talent no one talks about?”
This gives him 3 new high-quality intros per week.
B. Host niche meetups
He hosts a healthcare founder meetup every month.
He’s met 1,000 top founders in a single year.
C. Surround yourself with intensity
He explicitly seeks out founders who are uncomfortable to others.
10. You Have to Be a Masochist
The best founders:
Enjoy getting punched in the face
Thrive on “no”
Work harder than everyone
Are unshakeable in the face of rejection
And after 1,000 interviews, Harry sees three childhood traits almost every time:
1. They moved a lot in childhood
Constant assimilation and rejection built resilience.
2. They were part of gaming clans
Competition, teamwork, stress, strategy.
3. They started something entrepreneurial early
Side projects at 12. Building something at 14. Hustling at 16.
Not one great founder he’s interviewed started at 25.
Hope you found this as valuable as I did. Enjoy!
Best,
Guillermo
1. What makes Harry Stebbings such a successful venture capitalist?
Harry Stebbings attributes his success to relentless discipline, deep founder empathy, extreme work ethic, and long-term relationship building with LPs and founders. His approach combines intensity, speed, and a rare willingness to do high-effort tasks others avoid (e.g., personalized outreach, weekly LP calls, constant iteration).
2. What psychological traits do billion-dollar (decacorn) founders share?
According to Harry Stebbings, nearly every $10B+ founder has:
A superiority complex (a belief they can do what others can’t)
A deep inferiority complex (feeling they’re never doing enough)
A masochistic driver (pushing themselves to uncomfortable levels)
This combination makes them uniquely resilient, obsessive, and capable of non-linear output.
3. How does Harry Stebbings build relationships with LPs so effectively?
He speaks to two LPs every week, year-round — not only during fundraising. He keeps a CRM of 400 LPs, sends quarterly updates, asks every LP who else he should meet, and writes hundreds of personalized notes in one day. This compounds over years and makes fundraising happen in days, not months.
4. How does Harry Stebbings raise capital so quickly?
Harry’s fast raises (e.g., $75M via WhatsApp) come from long-term trust compounding. Because he consistently nurtures LP relationships over years, he never starts from zero when launching a new fund.
5. What is Harry Stebbings’ decision-making framework for opportunities?
He chooses the option that opens the most future options.
If one path expands surface area for luck, relationships, or opportunities, he chooses that — even when it’s uncomfortable.
6. What is Harry Stebbings’ cold email formula?
His winning cold email playbook includes:
A clear subject line
Zero fluff or pleasantries
Stating the objective immediately
Short, direct, high-conviction communication increases reply rates dramatically.
7. How does Harry evaluate founders at pre-seed and seed?
Harry ignores almost everything except the founder.
He optimizes for:
Founder quality
Unhinged intensity
Deep obsession
He considers market analysis, TAM slides, and early traction far less important at this stage.
8. Why does Harry believe interviewing makes you a better investor?
Interviewing teaches you to:
Make people comfortable fast
Build trust by exposing your own vulnerability
Get people to open up by asking for advice
These skills transfer directly to founder assessment.
9. What does Harry Stebbings mean by “Never brainstorm. Just go”?
He believes velocity beats planning.
Instead of sitting around ideating, you learn by moving, iterating, and accumulating at-bats. Speed creates outcomes.
10. How does Harry intentionally increase his surface area of luck?
He designs his life to maximize high-quality collisions through:
Weekly interviews with decacorn founders
Hosting niche meetups (e.g., healthcare founders)
Surrounding himself with intense, driven people
Luck is built, not found.
11. What early-life patterns do top founders share, according to Harry?
After 1,000 interviews, he sees consistent childhood traits:
Moving frequently (building resilience through constant assimilation)
Being part of gaming clans (teamwork, competition, strategy)
Starting projects or side hustles early (early entrepreneurial wiring)
Almost no great founder starts late.
12. How does Harry follow up after events or dinners?
He visualizes the table and emails each person in the Uber ride home — never the next day.
This signals intensity, professionalism, and reliability, and differentiates him from 90% of people who follow up too late or not at all.
13. Why do VCs say Harry Stebbings has “velocity advantage”?
His operational tempo — rapid interviewing, constant relationship-building, immediate follow-ups — compounds into more opportunities, more information flow, and faster deal access.
14. What are Harry Stebbings’ biggest investing mistakes and why?
He regrets:
Passing on Vanta
Passing on Deel
Both decisions came from overthinking the market instead of focusing on the founders.
15. What can founders learn from Harry Stebbings’ approach to intensity and work ethic?
Founders can emulate:
Relentless follow-through
Continuous outreach
High-frequency iteration
Turning discomfort into advantage
Systematic luck creation
Intensity compounds — and Harry operationalizes it daily.