How 19 Year Old Harry Stebbings Became a Venture Capital Star

This past week, Brad Feld, Fred Wilson, Roelof Botha and Marc Andreessen all separately praised the journalism of Harry Stebbings. Who is this guy?

While every Harvard MBA is trying to find a way into venture capital, how did an unknown Brit cut ahead in line and become a go-to-source and door-opener? To paraphrase the cartoonist Peter Steiner, it helps that on the internet, nobody knows you’re a 19 year old.


I was introduced to Harry Stebbings’ work at my lowest moment. I was undergoing chemo and radiation and had little energy. During those long hours with my feet propped up, I checked out every podcast I could find about startups and came across Harry’s “The Twenty Minute VC”.  The earliest podcasts weren’t that great, but they just kept getting better. What became apparent over time was that in interviewing VCs, doing his homework and studying the field, Harry kept applying their teachings to his own business, with spectacular results. While Harry started as a student/groupie, listening to his idols, he now has become the role model: his business can easily be turned into a case study of how to incorporate Lean Startup methodology, inbound marketing, virality, and much of today’s startup gospels and convert it into uncommon reach and influence.

But first, back to how I met Harry.


After recovering from the cancer treatments, I published  highly subjective rankings of 75 startup podcasts. I gave Harry a B, summing up the show as “VCs fawned over by an overenthusiastic Brit”. (He’s a solid A now.) I loved the concept, the structure, the brevity, but a number of characteristics bothered me. Harry actually was doing two podcasts at the time, the other one focusing on European angels; it was justifiably forgettable.  

Startup Lesson #1 Experiment, Iterate, Repeat. Looking back, these early podcasts were classic examples of creating MVPs–essentially Harry executed 2 beta projects, and then focused on improving the more successful VC podcast. The angel podcast just wasn’t attracting as many downloads for predictable reasons. Interviews of low profile angels investing small amounts of money couldn’t compete with shows with higher profile VCs investing big buckets of money. Harry analysed the data, and ditched what wasn’t working.

Startup Lesson #2  Market Research and Customer Discovery. After my blogpost, Harry contacted me, saying “Hi–I’m that ‘overenthusiastic, fawning Brit’ you reviewed. What can I do to make my show better?” and we had a nice discussion. I admired that he took the time and risk to his ego to get feedback from critics. He asked me perceptive questions about other startup broadcasts competing for my attention, trying to determine how his show could be sufficiently better or differentiated to keep my attention. He asked about a competitive VC interview show (one that was a little longer and more ponderous) that I’d given higher grades to, and wanted to know why. He changed some things (no longer effusively praising any minor league VC with no meaningful exits as a “legend”), but also stood his own ground when I suggested that he ask more hardball questions. He–quite correctly, given his stage–didn’t want to risk pissing off his guests, for fear of getting a bad rep and losing referral intros. (Harry, I know you’re reading this–you’d become my favorite podcaster of all time if you get another interview with Tim Draper and ask “What is it with this Ayn Randian bullshit about all government is bad, Silicon Valley should secede from the US so you don’t have to support less advantaged parts of the country, and your refusal to admit that Theranos’ management made egregious errors?” Just asking!)

What has happened, though, is that as Harry himself has gotten wiser and more confident, he now draws on his previous interviews to diplomatically bring up the opposing viewpoint and incorporate it with some authority without overtly confronting his subject. “You know, xyz was on the show and makes the different case that…”

Startup Lesson #3: Customer Acquisition and Virality. How did you hear about the 20 minute VC? A tweet or blog from a venture capitalist you follow? Postings on Product Hunt? The Mattermark Daily? Whatever the means, I’m sure that Harry’s listener acquisition cost is zero. He’s ballooned to 100k downloads per show, getting bumps from social media mentions of people with large followings. VCs who have been interviewed naturally publicize the show, looking to capture the attention of the many young startup founders who comprise a good part of the audience. This didn’t come easily, although I admit most VCs chase publicity like a politician chases votes. The Twenty Minute VC’s first big break came from establishing a cross-platform partnership Mattermark, which knows a thing or two about growing a loyal audience of VCs and startup folks. Which goes back to…

Startup Lesson #4: Inbound Marketing Simply put, this concept requires quality content to be put out regularly to build an audience. From sheer hustle, Harry has created enough of a backlog of shows that not only can he publish on a steady, 3x a week schedule, and now has enough shows in the wings that he can do quality control and simply not publish the dogs. And he posts on all the major social media channels.

Startup Lesson #5: Leveraging Networks How has a 19 year old outside of Silicon Valley gotten so connected? Well, one interview leads to another…and he’s always quick to thank and give public credit to the introducer. While no stranger to cold-calling prospective subjects, he knows a warm intro is always the best way to gain access. The latest example: Harry now also hosts the SaaStr podcast, bringing in the enormous audience, influence and contacts of Jason Lemkin. And Harry’s impact just keeps snowballing…

Startup Lesson #6: Branding  Just think of that great name: “The Twenty Minute VC Podcast” says it all in 5 words. While not all shows actually stick to twenty minutes, it seems to be just the right amount of time for a listener to digest a show during a commute and for the interview to contain something of substance. Right concept, communicated perfectly.

Startup Lesson #7 Breaking New Ground Ever see much content on, say, the perspective of a VC fund’s limited partners–i.e., the source of all the money? I thought not. Harry filled the gap, with examples like this show with my favorite LP/blogger, Chris Douvos, of Venture Investment Associates.

Startup Lesson #8 Give First  I have yet to have a conversation with Harry where he did not ask “How can I help you?” Before Chris Sacca and Mike Maples earned their reputations and dealflow, they made themselves valuable to others any way they could. Paying it forward is always rewarded in the end.

This is just Part I of the Harry Stebbings Saga     I get asked all the time by young grads “How do I get into VC?” I used to talk about getting operating experience, blogging to create a personal brand, networking…all the usual cliche advice. Now I just tell them to consider how a 19 year old who skipped college has become a household name with VCs. Be like Harry.

There are many investors who started as journalists–Michael Moritz, Esther Dyson, Stuart Alsop, Jason Calacanis, Semil Shah, MG Siegler… the list goes on. I have ZERO doubt that Harry soon will not be able to escape the allure of venture. He has an audience, he understands what it is to be a founder, he has influential fans, knows how to ask questions, and works his ass off.  If I were a VC, I’d be recruiting him as hard as possible.


Harry, in the words of your countryman Ali G, “Respek”!

[Postscript–after seeing the published post, Harry informs me he is no longer a teenager, having turned 20 two weeks ago. But in my book he is still a wunderkind!]



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