Jan 24, 2026 · 42m · 20vc
20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this special episode of 20VC, podcast host and venture capitalist Harry Stebbings sits down with Simon Squibb to share his journey from starting a podcast at age 18 to managing a $400 million venture fund. Harry breaks down seven critical lessons learned from interviewing over 100 billionaire founders, covering cold emailing techniques, relentless execution, fundraising strategies, and personal resilience.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 68.4% of the talking time here. How this is scored →
Harry as informed peer 7.8 Guest teaching 1.3 Guest disagreement 1.2 Harry pushing back 1.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 27:36 Simon highlights tension in Harry's views on money and happiness
Simon gently challenges Harry's framing on wealth by pointing out the potential contradiction between claiming money buys happiness and earlier asserting that money is not enough.
Hardest push from Harry ▶ 18:42 Harry pushes back on creator product launches using MrBeast BurgersHarry counters Simon's push for creators to build physical product brands instead of taking sponsorships by citing operational failures and quality control traps like MrBeast Burgers.
Biggest teaching moment ▶ 9:07 Simon reminds Harry of his humble Periscope originsSimon educates the audience and reframes Harry's current authority by recounting Harry's eager, over-effusive early days on Periscope 13 years prior.
Harry holds his own ▶ 4:37 Harry details generating $1.75M from 25 cold emailsHarry showcases deep tactical expertise by demonstrating how he structured $95k sponsorship pricing to stay below corporate procurement caps, closing $1.75M in 24 hours.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| How Harry Made $1.75 Million at Age 19 | 8 | 1 | 1 | 1 | Harry details his tactics for securing $1.75 million in sales at age 19 by pitching tech CEOs slightly below procurement limits and adding personalized touches. Simon enthusiastically agrees with Harry's process and sales philosophy. | |
| The Art of Cold Emailing and Leveraging Social Proof | 8 | 1 | 1 | 1 | Harry shares actionable strategies for cold emailing billionaires using social proof, generating referral flywheels, and moving contacts to WhatsApp. Simon validates these strategies with his own anecdotes. | |
| Reflecting on Early Beginnings and the Long Pursuit of Success | 7 | 2 | 2 | 2 | Simon reminisces about meeting Harry on Periscope 13 years prior, prompting Harry to discuss early persistence and why wealth creation should be aggressively pursued to unlock economic advantages. | |
| Cultural Mindsets, Positivity, and Turning Failure into Success | 8 | 1 | 1 | 1 | Harry contrasts UK cultural skepticism with American positive visualization, introducing Project Europe as an initiative to back ambitious young founders while recounting how personal adversity sparked his media career. | |
| Overcoming Adversity and Managing Daily Optimism | 7 | 1 | 1 | 1 | Harry outlines tactics for maintaining daily optimism and notes that early content failure carries zero downside because no audience is paying attention yet. Simon concurs with the leverage of social media. | |
| The Evolution of Creators into Enterprises | 8 | 2 | 2 | 2 | Harry cites driving $4M in revenue for a portfolio company from one post to prove distribution is key. When Simon talks about launching creator brands, Harry offers a measured pushback citing operational pitfalls like MrBeast Burgers. | |
| Lessons 1 & 2: Overcoming Rejection and Relentless Outbound | 8 | 1 | 1 | 1 | Harry delivers specific outreach frameworks, including turning down initial nos to raise $12M and sending 53 weekly cold emails to Marc Benioff to convert him into a podcast guest. | |
| Lesson 3: Action Drives Outcomes and Overcoming Fear of Failure | 7 | 1 | 1 | 1 | Harry advocates for immediate action over fear of failure, noting that action clarifies market needs faster than theoretical planning. Simon strongly echoes this mindset. | |
| Dropping Out of University and De-Risking Entrepreneurship | 8 | 2 | 1 | 1 | Harry describes dropping out of King's College Law after securing a $100k sponsor, using decision frameworks based on role models, and reflecting on why wealth alone failed to bring him early happiness. | |
| Mentorship, Team Building, and Relentless Execution | 8 | 1 | 1 | 1 | Harry reframes mentorship around scalable content and explains his four-burner cooker model for managing family, friends, work, and fitness through integration. | |
| Lesson 6: Execution Over Originality and System Defensibility | 8 | 2 | 1 | 1 | Harry argues that business defensibility lies in daily operational execution and small iterative improvements rather than raw originality, quoting Spotify's CPO on process design. | |
| Breaking Down Massive Visions into Daily Execution | 8 | 1 | 1 | 1 | Harry breaks grand visions down into daily executable steps, shares his interpersonal Hitch networking tactic, and recommends small micro-habits to build daily happiness. |
Statements from this episode (26)
Stebbings: Young VCs Should Return Capital Before Seeking Media Exposure
“I think you have to really return a lot of money to investors before you think you're worthy of being interviewed, and I think too many young VCs are too out there when they haven't made a lot of money for investors”
Stebbings: Sent 53 Cold Emails to Book Marc Benioff on 20VC
“How I got Mark Benioff to come on TwentyVC through 53 cold emails”
Stebbings: Sold $1.75M in Podcast Sponsorships in 24 Hours at Age 19
“I priced it at 95,000 dollars each, just under the hundred grand procurement budget, and I got 19 of them say yes, they would love to, and that was 1.75 million dollars in 24 hours.”
Stebbings: Schools Fail to Teach Sales and Public Speaking
“School misses the two most important things, which is sales and public speaking.”
Stebbings: Adding Highly Specific Personal Details Triples Cold Email Response Rates
“And so at the end of every single email, I'd put, P.S. I know that Mackellan 75 is your favorite whiskey. I'd love to have one with you when you're next in London. The minute that you add that, you literally treble your chances of getting a response.”
Stebbings: Ask Podcast Guests for Three Recommendations to Secure Warm Intros
“At the end of every show, I would say to people, hey, who are three people that you think I should have on that would be fantastic? And the minute people commit to three more names, I would say, hey, if I send you an email that you can forward onto them, would…”
Stebbings: Raised 20VC Capital via WhatsApp Between Gym Sets
“When we fundraise, we raise from very rich individuals, we raise from, you know, institutions, and I would, in between sets in the gym, walk around in my two-minute breaks, and I would message individuals, this was, and say, hey, I'm going out to raise the new…”
Stebbings: Move business contacts off email onto WhatsApp to build genuine rapport
“What people don't see is the 10 years of relationship building before that, but the most important lesson from that, actually, is I always want people off email. Get people off email. People want to work with people who they like”
Stebbings: Built Early Business by Leveraging Famous People's Ego and Insecurity
“Did not have a big following at all, and I leveraged ego and insecurity of famous people and successful people to make money.”
Stebbings: Entrepreneurs Should Chase Making Their First Million Above All
“You should aggressively chase making your first million more than anything else, because the hardest to make is your first million by far.”
Stebbings: Project Europe is a $10M Fund Giving $200K to Young Founders
“It's why I started Project Europe, which is a ten million dollar fund, which gives 200 grand to incredibly young people to do unreasonably ambitious things.”
Harry Stebbings: Being Expelled from School Led Directly to Starting 20VC
“I would never have started the media company. If I hadn't been kicked out of boarding school.”
Harry Stebbings: Mental capacity for optimism mirrors capacity for unprovoked misery
“If you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason.”
Stebbings: 20VC Took Four Years to Reach 1,000 Plays
“It took me four years before I got a thousand plays.”
Stebbings: Content success is about survival; early failures carry zero risk
“This is a game of who can survive the longest, and the lovely thing about content, Simon, if you fail, it's because no one cares, and if no one cares, no one will know that you failed.”
Squibb: Communication and marketing have replaced tech as business barriers
“I used to think technology was going to be the barrier to entry to building businesses. I think now it's the ability to communicate, like you said, the ability to sell, and frankly, Marketing.”
Stebbings: Proprietary Media Distribution Drives 20VC Fund Outperformance
“Well, this is why our venture funds are doing so well right now, which is because everyone has a venture capital fund today, sadly, but not everyone has distribution.”
Stebbings: A Single LinkedIn Post Generated $4M in Revenue for Fixer
“I posted about them on LinkedIn, and they got four million in revenue from one LinkedIn post.”
Squibb: Launching a competitor brand to Starbucks
“I'm launching a competitor to Starbucks as part of my business model.”
Stebbings: MrBeast Burgers was a poor product choice for creator monetization
“Mr. Beast did Mr. Beast Burgers. Bad, and he'll say this himself, bad product to choose, difficult to monitor quality, difficult time delivery.”
Stebbings: Uses "What Would Sequoia's Pat Grady Do?" as Decision Framework
“Think of someone who you deeply respect and admire and you want their life. For me, it's Pat Grady at Sequoia. Three reasons. Great father, great investor, Great husband. And whenever I'm faced with a tough decision, I ask, what would Pat do in this case? And …”
Stebbings: Personal content builds relationships at scale to pre-sell stakeholders
“And it's a great way to pre-sell to have content as your relationship builder at scale.”
Squibb: Top mentors lack time for constant one-on-one meetings
“They think they need to sit down with that person and have one-on-one conversations all the time, but the best mentors haven't got time for that.”
Stebbings: Hires Family and Friends to Bypass Work-Life Balance Trade-Offs
“My business partner always tells me very correctly, life is like a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness, ok? Family, friends, work, and fitness. And the trouble i…”
Stebbings: Improving an existing model by 10-20% yields successful businesses
“Very often you can just take something that works and make it 10 or 20% better. Oh, I love that cafe, but I've always wondered why they don't do really Instagrammable cakes, because the coffee is great. And the location is great. Why don't they do more? Making…”
Stebbings: Befriend a Target's Spouse to Influence Their Final Decision
“At the end of the day, a partner's statements about someone will very often impact their decision. So whenever I go to a dinner or a drinks party or whatever, the partner of the person that I want to influence will be my best friend, because the power of the c…”