The Man Who Interviewed 107 Billionaires: The Real Formula for Getting Rich

Chapter 1 · Narration: WOW Mentor

The Man Who Interviewed 107 Billionaires: The Real Formula for Getting Rich

Venture capitalist Harry Stebbings interviewed 107 billionaires and observed the repeating patterns of wealth — and at nineteen he turned a listener-less podcast into £1.75M in 24 hours to pay for his mother's medication. WOW Mentor unpacks his core claims: that sales is a learnable process, that social proof and compounding relationships build empires, and that distribution now decides value more than technology. Watching bailiffs take his grandparents' home taught him that money is security, and he protects his reputation with a 'would this be in the New York Times' test and a rule to only take advice from people whose life he wants. He also reports that only one of the 107 billionaires was happy, framing money not as a goal but as a luxury that buys freedom. From AI arbitrage and the creator economy to a pointed debate on ethics and taxation, this episode lays out a working formula for escaping poverty.

Today, WOW Mentor breaks down the conclusions of a man who sat across from 107 billionaires and asked each of them, point blank, how they got rich. His name is Harry Stebbings — a venture capitalist and interviewer who has put everyone from Sam Altman to Revolut founder Nik Storonsky in front of a microphone to extract their formulas for success. But what WOW Mentor wants to notice first is not the stories of the billionaires he interviewed. It is a single case study the interviewer himself proved at the age of nineteen. A boy with no followers and no name generated £1.75 million — well over two million dollars — in twenty-four hours. Inside that one event, nearly every principle this episode is trying to teach is already compressed and waiting. Behind that story was desperation. Harry's mother had multiple sclerosis, and the medication she needed cost roughly $750,000. All Harry had at the time was what he himself calls a useless podcast — one with essentially no listeners. How do you turn a channel that earns zero dollars into three-quarters of a million? He went up to his bedroom and emailed twenty-five of the biggest CEOs in technology. The core of the message was this: your biggest competitor wants to sponsor this podcast, but I am a fan of your product, so I am offering it to you first. He priced each sponsorship at $95,000. And here is the number WOW Mentor insists you do not skate past. In large companies, procurement authority typically breaks at around the $100,000 line — below it, a manager can approve a deal alone; above it, sign-off has to climb the ladder. $95,000 sat deliberately just beneath that $100,000 threshold, targeting the maximum a decision-maker could approve without asking anyone above them. The result: nineteen of the twenty-five said yes. And so $1.75 million was created in a single day. The first cut WOW Mentor makes here is into FOMO — the deliberate engineering of the fear of missing out. Harry planted the frame that a competitor had already shown interest, creating the tension that if the recipient hesitated, they would hand the slot to their rival. This is not a lie; it is psychological framing. In this conversation, Harry argues flatly that sales should be taught in school. Sales is not a talent, it is a process, and school skips the two most important subjects of all. One is sales; the other is public speaking. Then he adds a third: personality — likability. People, in the end, want to work with people they like. That element of likability is the second thing to dissect. Harry attached a P.S. to the end of every email: "I know the Macallan 75 is your favorite whiskey. I'd love to have one with you next time you're in London." The moment you add that line, he says, you literally triple your chances of a response. What WOW Mentor wants to highlight is that this is, at its heart, effort applied to detail. The work of researching what someone loves and writing one personalized sentence for them. So few people bother that the bother itself becomes the differentiation. The host, Simon Squibb, recalls the same pattern: the people he has hired messaged him on LinkedIn having genuinely understood what he was trying to build and bringing real value in the message itself. A note that says "Hi, I'd love to work with you because I can learn so much" is, in the end, only about taking from the other person. Harry summarizes it by borrowing Seth Godin's phrase: if you want to win, be a purple cow. Just be different.

The third weapon under the knife is social proof. Asked how he managed to book 107 billionaires, Harry's answer comes down to relentless, well-crafted cold emails. A good cold email is short, concise, has a clear ask, and is personal. On top of that, you layer social proof as a weapon: "I just interviewed Richard Branson, and I'd love to have you on." Very few entrepreneurs are unwilling to be associated with a name of Branson's caliber. Harry used that social validity to signal that his channel was a strong, good environment people wanted to be linked to. Simon shares the identical experience from his own agency, Fluid. When it was unknown, he called a company saying "I'd love to work with you," and they said, "Sorry, we're busy." So he called back and said, "Hi, I'm working with CNN." Suddenly the answer changed: "Oh, you're working with CNN? Sure, come on in." What WOW Mentor wants to stress is that sales is not a synonym for being sneaky. Using social proof is not the slick trick of a car salesman; it can be an honest way of transmitting trust in compressed form. To this Harry adds the concept of the flywheel. At the end of every show, he asked the guest: "Who are three people you think I should have on?" The instant the guest named three, he followed up: "If I send you an email you can forward on to them, would you mind making the intro?" Once a person has said three names out loud, they are psychologically committed to the introduction. So every single show produced three new introductions. The core point WOW Mentor draws out is that a good business must be designed with a flywheel structure, where one success feeds the next. Introductions begetting introductions, guests begetting guests — that rotation is what made the number 107 possible in the first place. The fourth thing to dissect is the claim that Harry raised £70 million on WhatsApp. People hear that and marvel, "How do you raise seventy million on WhatsApp?" — but the real truth sits underneath. Between sets at the gym, during his two-minute rest breaks, he would message wealthy individual investors: "I'm going out to raise a new fund and I'd love to have you in." Back would come the replies: "Count me in for a million." "Count me in for two." But what WOW Mentor insists you look at alongside this is the ten invisible years that came before. That one two-minute message only worked because a decade of relationship-building preceded it. And here he names a decisive habit: get people off email. At the end of every call and meeting he says, "Simon, I'm terrible at email. Let's jump to WhatsApp." Then, on a weekend walk with his mother, he snaps a photo of the two of them eating a donut and sends it: "Loved our meeting this week. Next time you have to join us on the walk." People resonate with people. He built those personal relationships on WhatsApp in a way few others do. But hearing all of this, someone will object: "Of course he can raise money over WhatsApp — he already has a big following." That is exactly why the nineteen-year-old story is the decisive one. Back then he had no following at all. What he leveraged was the ego and insecurity of famous, successful people — their fear of falling behind a competitor, their desire to be linked with a good brand. And his motivation was not mere desire; it was need. This is the distinction WOW Mentor asks you to hold onto. He did not merely want a million pounds — he needed it. That difference between wanting and needing, the moment that switch flips, may be the only trigger that truly sets a person in motion.

… The rest of this chapter continues in the full edition, available with a subscription.

Listen to this chapter