How 19 Year Old Harry Stebbings Became a Venture Capital Star

A few weeks ago, Brad FeldFred 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 1 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!]

This post was originally published on Ty’s blog

Every Damn Imaginable Startup Podcast Reviewed

As a long-distance commuter, I listen to a LOT of podcasts. And given the explosion in podcasts on tech startups, it’s hard to keep track of them all. There really isn’t a good discovery source, although Product Hunt and The Podcast Wire come closest.  So here’s the survey we’ve been missing. I have left out general business podcasts and most of the podcasts for small business (although I kept those few specializing on women entrepreneurs, whose focus is mostly on small bootstrapped companies,) and focus on the ones relevant for the founders of VC-backed startups who are looking to go big.

Before we hit the ranked list of 75, yes, 75! podcasts below, a few thoughts.

A) The formats of almost all of the best podcasts are interviews or taped lectures. 16 of the 24 podcasts graded A- or better are one or the other.

B) Interview quality varies greatly, even with the same host. Jason Calacanis (This Week in Startups) and Andrew Warner (Mixergy) each have done many hundreds of podcasts. So not only can the quality of the guests vary, sometimes the hosts has a bad day. (A guest like Chris Sacca or Danielle Morrill brings out Jason’s best, at which times there is no one better. But when he’s not really into the guest, he reverts to constant name-dropping and “me-me-me” mode. That’s why he has a massively polarized audience, with 90 5 star iTunes ratings…but 30 1 stars. He’s someone I love and hate at the same time…so “A” Jason + “C” Jason resulted in a B rating from me.)

C) The podcasts available in both audio and video versions generally are better than audio-only podcasts. Better production value, better preparation, better guests. Similarly, the video content on Youtube for any one speaker is superior to the audio podcasts. Best example: Eric Ries videos (like this talk at Google) are preferable to his podcast. Why? I think people just work harder on videos. Another example, discussed below: Y Combinator’s “How to Start a Startup” video podcast is great, but it’s audio-only “StartupSchoolRadio” is lacking.

D) If the podcast comes from a blogger, the blog is better crafted and quicker to consume. One example is Steve Blank’s podcast, which is delivered unconvincingly by a voice actor reading over the excellent blog. It’s lost in translation. Similarly, John Gruber’s Daring Fireball blog is incisive and readable, but his podcast meanders forever. One possible exception is the output of Ben Thompson: while his outstanding Stratechery column is superior to his podcast, the two ARE additive. If you don’t subscribe to Stratechery, at least check out his Exponent podcast; it is free and features the most incisive thinking in tech.

E) VC and company-sponsored podcasts generally are solid, but accelerator-sponsored podcasts don’t cut it. 3 out of the 6 A+ rated podcasts come from VCs.  The VC winners: “Ventured” from Kleiner Perkins, “A16Z” from Andreessen Horowitz, and “Traction” from NextView Ventures. They are putting their reputations on the line, and podcasting is one way they try to attract the best entrepreneurs. Similarly, the better corporate podcasters (e.g., Hubspot, InsightSquared, Intercom, 37 Signals) are trying to gain goodwill by being thought leaders more than just shilling their product. But the podcasts from the accelerators inexplicably are so-so to poor, with a B going out to Seedcamp, a B- to the (discontinued?) 500 Startups podcast, and a generous C+ to the tone-deaf StartupSchoolRadio from Y Combinator. To be fair, Sam Altman of YC organized a Stanford lecture series “How to Start a Startup” which featured great lectures from incredible speakers. However, the podcast shows the damage a mediocre host can do. The host, (who incidentally was only in one startup, which cratered quickly in spite of raising a bunch of money,) tries to parrot Paul Graham’s more famous sayings onto any conceivable example, without nuance or in some cases understanding. Just go to the source and read Paul’s brilliant essays instead. And going back to point C), check out 500 Startups terrific Youtube video channel for great lectures on growth-hacking.

F) Anything Stanford touches is gold. How to Start a Startup and especially Entrepreneurial Thought Leaders are awesome. It’s not just the household name speakers. Wondering about what goes into acquisitions of startups by larger tech companies? Check out Jeff Seibert’s wonderful lecture, dealing with the good and bad he learned from selling 2 companies (to Box and Twitter) and buying some for his new bosses. (BTW, if you want the best digital startup education out there, StartupSecrets films a great class by VC/HBS Prof Michael Skok and puts it on the web. Not a podcast, not on iTunes, so not included on list below, but otherwise A+! Curriculum/readings included.)

Explanation of the Table

The podcast name and its embedded link is followed by my personal, subjective grade, along with the number of podcasts in the series , the number of 5 star ratings/total ratings in the iTunes Store for consensus opinion, and date of the last podcast to show frequency.

At the bottom. I have more detailed notes. Let me know which ones I’ve missed or where you disagree in the comments.

Name Summary Itunes
Ventured A+ From Kleiner Perkins: Randy Komisar and friends. Check out Bill Campbell episode. 14 5/9
How to Start a Startup A+ The biggest names in Silicon Valley take on a topic in this Stanford lecture series 20 21/39
Startup Podcast A+ Following 1 startup a year, NPR-style storytelling 32 4004/4027
Entrepreneurial Thought Leaders A+ More talks at Stanford by Steve Blank, Elon Musk, Reid Hoffman, etc. 251 166/256
Traction A+ Getting growth between seed and A round 16 64/64
Dorm Room Tycoon A+ The biggest names, interviewed skillfully 131 24/24
Work in Progress A 37 Signals execs talk openly and honestly about running the company 59 6/6
Design Details Podcast A Designers at GoPro, Etsy, Pinterest talk shop 93 141/152
Product People A Emphasis on virality and engagement; Aimed at bootstrappers 75 44/47
UX and Growth Podcast A Hubspot Designers/Developers talk their subjects 15 n/a
A16Z A A16Z partners talk about current tech topics 187 18/28
Tech In Boston A- Interviews of players in the Boston tech ecosystem 57 18/18
Bothsides TV A- Mark Suster and guests. I’ll consume anything Mark puts out. 19 3/6 Podcast A- Product management, design, and marketing 11 n/a
Exponent A- Tech and Society: Ben Thompson and James Allworth’s weekly discussion 62 54/61
The Tim Ferriss Show A- Author/investor Tim Ferriss interviews world class performers 132 1855/2822
Foundation with Kevin Rose A- Terrific TV from the very connected investor Kevin Rose 43 12/14
Founder Calls with Aaron Levie A- Fun but still meaty. Aaron Levie of Box interviews his peers 6 n/a
Re/Code Decode A- More journalism than education:stars interviewed by Kara Swisher 33 32/50
The Rocketship Podcast A- Lots of accelerator grads and MDs; ability to search by topic 106 126/126
Venture Studio A- Dave Lerner’s terrific interviews primarily with NY-based investors 16 14/14
Customer Success Radio A- Interviews about growth and metrics with solid guests 25 10/10
The Growth Show (Hubspot) A- Interviews from Warby Parker to Facebook to AirBnB to Heady Topper 59 111/125
The Startup Chat A- Two pros chat about SaaS, metrics, Growth 67 94/96
VentureBeat’s What to Think A- Tech news 61
Full Ratchet A- Interviews with partners at Spark, Social Capital, other cutting edge VCs 88 41/41
This is Product Management B+ Everything through the eyes of Product. One guest per week
Hallway Chat B+ Fun. Two Spark Capital VCs discuss trends. (But most shows dated) 21 n/a
Million Dollar Insights B+ Top SaaS practitioners interviewed 24 70/72 B+ Discussion of European startup news 25
The Pitch B+ Like SharkTank, with guest VCs–easy, fun listening 14 75/83
Collective Wisdom for Tech Startups B+ VCs doing a deep dive with startup CEOs 8 13/16
From Scratch Podcast B+ Half startup gods, half inspirational people from the real world 85 20/22
Product Hunt Radio B+ Hippest podcast going, interviews by Ryan Hoover. 38 n/a
Reboot B+ CEOs baring their souls to Jerry Colonna, a top Executive Coach 30 13/13
The James Altucher Show B+ Quirky writer/entrepreneur interviews A-listers 149 321/381
HBR IdeaCast B+ HBR editors discuss their articles–can be dry 504 108/182
Venture Voice B+ Plenty of interesting guests–albeit from 7 years ago 60 19/22
Startup Grind B Live interviews from conferences of bigger names 100 16/16
Seedcamp Podcast B Good guest list, mostly Americans being interviewed by British accelerator 69 n/a
Startups for the Rest of Us B Small business approach rather than venture-backed startups 270 279/296
LeanStartupCo B Interviews with practitioners of Lean Startup techniques by Eric Ries & co 174 n/a
Acquired B Tech acquisitions that actually went well 5 n/a
Mixergy B From big names to unknowns–check transcripts first. More details below. 1249 226/264
The App Guy Podcast B Startup discussion revolving around mobile apps 401 39/39
TwentyMinuteVC B VCs fawned over by an overenthusiastic Brit. 20 19/21
Developer Tea B Quick topics for coders 178 135/140
This Week in Startups B The best guests ever. The polarizing Jason Calacanis as host. Highest highs, frequent lows 611 91/137
The O’Reilly Data Show Podcast B Data Scientists. Pretty dry. 20
500 Startups Podcast B- Not as good as their YouTube stuff. Discontinued? 53 18/18
The Talk Show with John Gruber B- Discussion with Guest Pundits. Too longwinded and rambling 141 717/1785
Hack the Entrepreneur B- mixed crowd 173 288/305
Hack to Start B- Plenty better than this 78 n/a
Seth Godin’s Startup School B- Very basic. One topic per lecture. If you like Godin (I don’t), it’s an A- 15 94/122
NYRD Radio B- A discontinued but fun podcast with Alexis Ohanian of Reddit 9 14/15
Perpetual Traffic B- Panel discusses getting paid traffic to websites. 27 366/405
Startup Nation B- Israeli entrepreneurs 4 n/a
Women Who Startup Radio B- Panel style discussion of, by and for women entrepreneurs 10
Startup School Radio C+ Interviews mostly of YC alums and staff 30
Angel Insights C+ European/British Angels 29 n/a
The Competitive Edge C+ A few good names, but generally schlocky 61 n/a
SaaS Revolution Show C+ Probably the weakest of the SaaS specialty broadcasts, but not just SaaS 32 n/a
She Did It Her Way C+ Interviews with female entrepreneurs 53 21/22
The Gently Mad C+ “Inspirational” startup stories with soul-searching 60 108/126
The Slow Hustle Podcast C+ Founder lessons on “managing the pendulum swing” 62 31/33
Ask Gary Vee C Over-caffeinated celebrity-investor host offers good insights delivered like AM radio. Not my style, but plenty love him. 192 536/558
Angel Investing with Tatyana Gray C For beginning angels…by a relatively new investor. 15 40/41
Entrepreneur on Fire C Popular for reasons beyond me. Pass. 1175 2079/2169
Steve Blank Podcast C Voice-overs of Steve’s blogposts by other people 68
Zen Founder C The soft stuff: how to survive as a founder, by a psychologist 50 28/28
The Struggling Entrepreneur C For solo, underfunded entrepreneurs 284
Go For Launch D Total “Get Rich Quick” crap. Avoid at all costs 45 43/44
Freelancers Show NR Had technical problems, didn’t review 183 5/5
Venture Confidential NR Silicon Valley VCs, just started. First guest: Bessemer VC 1 n/a
The Changelog NR What’s new in open source for hard core techies 189 13/15


Stray Reviews

The one that got away: Startup Secrets  Unfortunately, this is not included in the table above because it is only available for web viewing, but I have to highlight it. Startup Secrets goes right into serial entrepreneur/VC/HBS professor/Techstars mentor-instructor Michael Skok‘s class at Harvard, recording the lectures. Not just videos, but slideshares, course notes, reading. Simply the best resource I’ve ever seen from one person. Thanks @mjskok!

Venture Studio  Dave Lerner, repeat entrepreneur, prolific angel, and currently Director of Entrepreneurship at Columbia University, assembles a list of sterling, but not necessarily well-known, names of investors who are at the top of their field (like Matt Harris of Bain Capital, considered the best fintech investor around), changing investing paradigms (like Dustin Dolginow of Maiden Lane Ventures and AngelList), or just spearheading NYC’s charge to arguably the 2nd most important region in startups (Alex Iskold of Techstars and David Tisch of Box Group.) Dave is soft-spoken but just as insightful as his guests. My favorite shows: those with John Frankel of ff ventures.

Collective Wisdom Founders Collective’s partners have done it all–success both as entrepreneurs and as VCs, with seed or A round investments in Uber, Buzzfeed, and Hotel Tonight. Eight hourlong fireside chats with founders (TripAdvisorZocDocBehance…), along with short clips of the highlights of the talks with investors, advisors, service providers. I should probably upgrade this–I hope they do more podcasts!

Mixergy. Andrew has amassed an enormous library of interviews. While many are with bootstrapped small business owners, he also has talked, all of them gets down to real details of strategies, and Andrew is fearless of asking any question and getting detailed examples. His two talks with Harley Finkelstein (here and here), head of business development for Shopify, are required listening for any biz dev producer or manager. Unfortunately, most of the archive are behind a paywall–you can try several for free, or subscribe and get current releases without paying. I recommend screening the transcripts before deciding which episodes you want to download.

Re/Code Decode.  Technews journalism from a masterful Kara Swisher. Timely interviews with both Dick Costolo and Ev Williams just after the latest regime change, digging for dirt. Other episodes in the same vein, like when she quizzes Brian Chesky about AirBnB’s future plans. You get the picture. Skilled interviews, but more entertaining than educational by design, and I personally opt more for education.

Thanks to the Techstars Boston Accelerator Program Director, Ty Danco for this post. Originally posted here.