Harry Stebbings on Raising $400M for 20VC and 53 Emails to Benioff

Summary

• The origin story is the whole method in miniature: at 19, needing $750K for his mother’s MS medication, Stebbings emailed 25 tech CEOs claiming their biggest competitors wanted to sponsor his zero-listener podcast, priced sponsorship at $95K each — “just under the £100,000 procurement budget” — and got 19 yeses: “$1.75 million in 24 hours.” The tradeable insight: he leveraged “ego and insecurity of famous people” with no listeners, using FOMO and a personalized PS.
• Cold outbound is a compounding asset, not a numbers game. Emails must be short, concise, with a clear ask, personal — and a PS (“I know that Macallan 75 is your favorite whiskey”) “literally trebles your chances of getting a response.” He emailed Marc Benioff 53 times, every single Sunday, before getting “Yeah, I’m in” — and had already planned the next step: the viral tweet about the 53 emails, which itself becomes social validity to land “the next Marc Benioff.”
• He raised $70M on WhatsApp while fundraising for a $400M fund, messaging individuals between gym sets (“Count me in for a million”). The mechanic: “Get people off email… People resonate with people” — weekend donut photos with his mum help build relationships. The caveat he insists on: “What people don’t see is the 10 years of relationship building before that.”
• “Distribution is the biggest determinant of value.” Everyone has a venture fund now; not everyone has distribution. Proof point: one LinkedIn post about portfolio company Fixa (email auto-complete) drove $4 million in revenue — “for an investor to bring you four million from one post… that’s actual value. And we have data to prove it.” The corollary thesis: creators become companies (CR7 “is a brand as big as Starbucks”), so why promote someone else’s brand when you can own one — with MrBeast Burgers as the product-selection cautionary tale.
• Never accept no: after two LPs turned him down, he emailed back — “I have missed $500 million of investments… because I thought the person was great, but I did not like the market” — called both the next morning and closed $5M and $7M. “If you accept no, I would’ve not had 12 million there for the fund.”
• The wealth mechanics he calls unfair but real: “aggressively chase making your first million” because it’s the hardest by far, and “the world makes richer people get richer” — better banks, better rates, better access. But don’t chase money itself: his first million found him alone on a Fulham balcony with tequila and cigarettes; his actual happiness is “5 pound 60” — two espressos walking Hyde Park with his mother.
• The survival math of content: $50 Amazon microphone, three years to get good, four years to 1,000 plays — “this is a game of who can survive the longest,” and “if you fail, it’s because no one cares. And if no one cares, no one will know that you failed. So why don’t you do it anyway?”

Deep dive

1. $1.75 million in 24 hours at 19 — the FOMO trade that started everything

• The setup, as told: his mother’s MS medication cost $750,000, and he had “this useless podcast at the time which had no listeners.” From his bedroom he emailed 25 of the biggest CEOs in technology saying their biggest competitors wanted to sponsor the podcast but he preferred their product — would they take it? Priced at $95,000 each, “just under the £100,000 procurement budget,” 19 said yes: “$1.75 million in 24 hours.”
• The two ingredients he isolates: manufactured FOMO, plus personality — “everyone wants to work with someone who they like.” Every email ended “P.S. I know that Macallan 75 is your favorite whiskey. I’d love to have one with you when you’re next in London.” That one line “literally trebles your chances of getting a response.”
• Simon’s framing of why it worked — worth keeping: Harry didn’t just want the money, he needed it. “I think that’s the only flip switch people need to have.” Harry’s own gloss is blunter: “I leveraged ego and insecurity of famous people and successful people to make money.”

2. Cold outbound as craft: 53 emails to Benioff and the social-validity flywheel

• How he got 107 billionaires on the show: cold emails that are “short, concise, a clear ask, and personal,” then social validity as a weapon — “I just interviewed Richard Branson, and I would love to have you on the show. Who is not wanting to be tied to the brand of Richard Branson in the same caliber?” Simon’s parallel from founding Fluid: a prospect who said “we’re busy” said “sure, come on in” once he could say “I’m working with CNN.”
• The Benioff story in full: 53 emails, every single Sunday, each with a fresh personalized PS (“I hope the weather in X is nice — I knew you had a holiday home there”). On the 53rd: “Yeah, I’m in,” CC-ing his team. Harry’s own admission: “I would’ve blocked me.”
• The meta-lesson is thinking one step ahead in content: the moment Benioff said yes, “do you know what I’m thinking? Fucking viral Twitter” — the 53-email thread converts “someone worth $100 billion” into proof that compounds: “you can take it to the next Marc Benioff and be like, hey, I go viral with tweets like this.”
• The guest flywheel: at the end of every show he asked for “three people you think I should have on,” then — once names were committed — “would you mind making the intro?” “You always wanna create flywheels in any business where one leads to more success. With every show, I got three more intros.”

3. $70M raised on WhatsApp — and why to chase your first million anyway

• The mechanics: between sets at the gym, in two-minute breaks, he messaged rich individuals — “Hey, I’m going out to raise a new fund, and I’d love to have you in” — and got back “Count me in for a million,” “Count me in for two million.” His discipline: get people off email. “At the end of calls I always say, ‘Simon, I’m terrible at email. Let’s jump to WhatsApp’” — then weekend photos of him and his mum eating a donut. “People resonate with people.”
• The hedge he attaches himself: “What people don’t see is the 10 years of relationship building before that.”
• On wealth compounding, stated as uncomfortable fact: “aggressively chase making your first million… the hardest to make is your first million, by far. And the world makes richer people get richer” — posh banks, higher interest rates, better products, access. “It feels wrong. But the world is unfair and wrong… it unlocks so much more than you could anticipate.”

4. The UK’s negativity problem — and why his biggest failures became his biggest successes

• His diagnosis: “The biggest problem with the UK is that we are negative… you say an idea and we go, ’that’s not gonna work.’ In America we say, ’that’s gonna work.’” His answer is Project Europe, a $10 million fund giving 200 grand to incredibly young people “to do unreasonably ambitious things.” The second UK disease is snootiness — why would a Cambridge physicist open a bakery? “What happens if you open the most successful bakery in London… and become the next Cédric Grolet?”
• The failure-to-success chain, as told: “Getting kicked out of boarding school for being bulimic led to my entire life. I would never have started the media company… I would’ve been a mid lawyer.” His mother’s standing quote, from Scarlett O’Hara: “Tomorrow’s another day” — never let the prior day infect the next.
• The line worth putting on the wall: “If you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason. Embrace it.” And on self-belief: “This sounds arrogant, but I always knew I would be successful. It never dawned on me that it wouldn’t work.”

5. Just start, burn the boats, de-risk with one customer

• The start-anyway math: 99% of people never start; “just take the first step and you’re better than 99% of people.” He was terrible — $50 ice ball microphone from Amazon, “it took me three years before I probably got good… four years before I got 1,000 plays.” Simon matches it: six years building, “first three years, nothing.” Harry’s conclusion: “Most people give up. This is a game of who can survive the longest.”
• The freedom in obscurity: “The lovely thing about content — if you fail, it’s because no one cares. And if no one cares, no one will know that you failed. So why don’t you do it anyway?”
• The dropout decision, with its de-risking: a scholar at King’s doing law, he got a $100,000 sponsorship call, Googled how to write the contract himself, then asked his law professor’s salary — “82,000” — “and I thought, okay, well, that’s my answer.” Simon’s generalization: you can mitigate the risk of starting by getting one customer first — Harry’s version: pitch a company “I can revolutionize your hiring using AI,” get 30 grand committed, then leave the job. “Sometimes you have to burn the boats to encourage action.”

6. Distribution is the biggest determinant of value

• Why his funds work: “Everyone has a venture capital fund today, sadly. But not everyone has distribution.” The data point: one LinkedIn post about portfolio company Fixa, an email auto-complete tool, generated “four million in revenue from one LinkedIn post… that’s actual value. And we have data to prove it.”
• The creator-as-company thesis, jointly built with Simon: platforms captured attention (Facebook, then Snapchat/Instagram); Simon thinks the next big platform is a creator. Simon is launching a Starbucks competitor rather than taking sponsor fees from a brand he doesn’t believe in; Harry agrees — “People are companies today. Cristiano Ronaldo, CR7, is a brand as big as Starbucks… he’s not a person anymore.” The caution: MrBeast Burgers — “bad product to choose, difficult to monitor quality” — choose products well, since quality and delivery can be difficult to monitor.
• Against copying: most aspiring creators “just copy what works.” Simon’s street hook — “What’s your dream?” — is the counterexample: “I’m like, fuck, I’m in.” But Simon’s correction matters: the hook was iterated, not designed — his first version, “what business would you start?”, “wasn’t quite working… I just literally executed every day until it got better.”
• On moats, quoting his “dear friend” Gustav Söderström, CEO of Spotify [stated as CEO as spoken]: “The details are not the details. They are the product.” Harry’s version: “The defensibility of a company is the daily processes… sustained over long periods of time. It’s rarely actually the product. The product is the output.”

7. Money, happiness, and the operating frameworks: Pat Grady, pillow talk, four hobs

• Never accept no, with receipts: two people turned him down; he replied, “I have missed $500 million of investments… because I thought the person was great, but I did not like the market that they were in. I fear you are making the same mistake right now” — called both next morning, closed $5M and $7M. “If you accept no, I would’ve not had 12 million there for the fund.”
• The money paradox, told against himself: “chasing money will not lead to money… when you enjoy the art of doing, the money is the output.” His first million left him on a Fulham balcony with tequila and cigarettes and no friends to fill the club table he could now buy. What truly makes him happy: espressos with his mother in Hyde Park — “the espressos are 2 pounds 80… 5 pound 60 is my happiness.”
• The decision framework: pick someone whose whole life you’d want — for him, Pat Grady at Sequoia (“great father, great investor, great husband”) — and ask “What would Pat do?” It “generally always leads me to make the right and honorable decision when I might have otherwise made a different decision.”
• The influence and life-architecture hacks, rapid-fire: the Hitch lesson — befriend the partner of the person you want to influence, because “the power of the car journey home is what dictates what Simon actually does.” And his business partner’s four-hobs model — family, friends, work, fitness, “you can only keep two on at the same time” — solved by hiring his mum and brother and working with his best friends: “four become two.” The unpopular truth underneath it all: “Most people say they want it, but they actually don’t want what it takes — it’s every weekend,” and he says he has worked every Sunday, struggling on holidays because “you basically stare into the abyss and you don’t have anything staring back at you.”