Nov 13, 2015 · 26m · 20vc
20 VC FF 021: From TechCrunch to Founder to TechCrunch with the legend, Steve O'Hear
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this Founders Friday episode of The 20 Minute VC, host Harry Stebbings interviews tech journalist and former startup founder Steve O'Hear about his career at TechCrunch, his experience founding Beeple, and key insights into media relations, fundraising, and startup growth.
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 26.2% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 3.3 Guest disagreement 2.0 Harry pushing back 0.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:50 Disagreeing on press power
Steve explicitly rejects Harry's framing that TechCrunch holds the power to alter a startup's trajectory, stating that media influence is largely a myth.
Hardest push from Harry ▶ 22:56 Territorial banter on podcastingHarry jokingly checks Steve for branching into audio interviews by pointing out that Steve is stepping onto his turf.
Biggest teaching moment ▶ 12:25 Product-market fit versus media coverageSteve schools Harry on why media hype does not guarantee startup success, citing how his own startup received massive media coverage across major outlets yet still failed due to a lack of product resonance.
Harry holds his own ▶ 23:24 Demonstrating high-profile podcast guest rosterHarry asserts his credentials as an accomplished host by listing prominent venture capital figures he has interviewed, such as Brad Feld, Guy Kawasaki, and Mark Suster.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Steve O'Hear's Entrance into Tech Journalism | 1 | 1 | 0 | 0 | Harry welcomes Steve and asks standard biographical questions regarding his entrance into journalism and transition to founding Beeple. Steve shares his backstory amicably without conflict or deep technical probing from the host. | |
| Expectations vs. Reality of the Entrepreneurial Life | 2 | 3 | 1 | 0 | Harry prompts Steve on the comparison between consumer tech in Europe versus the US. Steve educates Harry on network effects, single-language markets, and European strengths in enterprise software. | |
| Fundraising Realities and the Investor Relationship | 2 | 4 | 1 | 0 | Harry asks about fundraising realities and TechCrunch's reach. Steve articulates the psychological shift and potential conflict of interest when closing VC rounds. | |
| Press Coverage vs. Product-Market Fit | 2 | 6 | 6 | 1 | When Harry asserts that Steve holds the power to change startup trajectories, Steve directly refutes the premise, calling media influence a slight myth. Steve uses his own failed startup Beeple as evidence that press coverage cannot overcome a lack of product-market fit. | |
| Editorial Independence and TechCrunch's Business Model | 2 | 4 | 3 | 1 | Harry inquires about TechCrunch's monetization model given declining ad revenue, but Steve politely undermines the premise by highlighting the strict separation between editorial and business ops. Steve later explains how listicles subsidize longform journalism. | |
| Quick-Fire Round: Books, Icons, Pitch Red Flags, and Seed Trends | 2 | 2 | 1 | 0 | Harry guides Steve through a quick-fire round covering books, inspirations, pitch red flags, and seed trends. The dynamic is lighthearted and informative. | |
| Future Outlook, Audio Journalism, and Interview Dynamics | 5 | 3 | 2 | 2 | Harry and Steve engage in peer-level banter over audio interviewing techniques and podcast turf. Harry demonstrates domain clout by naming high-profile guests he has successfully booked. |
Statements from this episode (15)
O'Hear: To Become a Journalist, Start Calling Yourself One
“He was basically like, Steve, there's way worse writers than you, and he was like, if you want to be a journalist, just start calling yourself a journalist, so that's what I did.”
O'Hear: Building Consumer Startups Is Significantly Harder in Europe
“When you write about this stuff every day, you're under no illusions about how difficult it will be, about how arduous the fundraising process will be, and how most consumer startups fail, right? Especially coming from Europe, it's much harder.”
O'Hear: US Single Market and VC Reach Accelerate Consumer Startups
“I think because America is a single market with one language, and you've got a lot more high-profile VCs on Twitter, you know, other, like other entrepreneurs, that they can, like, amplify your message a lot quicker in the consumer space.”
O'Hear: Europe's Tech Sector Historically Excels in Enterprise Software
“If you look at what Europe does best, or has historically done best, it's a lot of enterprise software, and sort of less You know, less consumer and less sexy.”
O'Hear: Fundraising Creates Conflict When Founders Pitch VCs
“There's, like An absolute conflict of interest in that stage when you're fundraising, because essentially you're telling your VC, in a way, you're trying to tell them what they want to hear, because you want to close the round. But the minute you close the rou…”
O'Hear: TechCrunch Coverage Drives Initial Investor and Media Interest
“Is I think the biggest impact my coverage made on a startup was often that we would, like my coverage would either lead to the first interest the startup had from investors or from mainstream media.”
O'Hear: Press Outlets Like TechCrunch Do Not Make or Break Startups
“And I don't think TechCrunch or anyone like TechCrunch Makes or breaks a startup. I think that's a slight myth.”
O'Hear: Great Products Earn Press While Weak Products Fail Regardless
“If you make a really awesome product, you'll get found out by the press because we can't ignore it. And if you make a bad product, You'll get found out by your customers or users, regardless of how much publicity you've gone out.”
O'Hear: Widespread PR Coverage Made Little Difference for Startup Beeple
“Beeple was covered everywhere. Like, because of my journalist background, we got in anywhere from CNN to Next Web, TechCrunch, obviously Fast Company magazine. Like, we were, at one point, we were everywhere for about two days, and I can tell you it made very …”
O'Hear: Unrestricted Early Community Onboarding Loses Conversational Tone Control
“You think that the way to launch a community is just to like invite everyone in. Everyone's welcome and the more the merrier, right? Especially when you're trying to grow your user numbers. But it's really interesting how, if you're not careful, you do lose co…”
O'Hear: Media Publications Enforce Tighter Editorial Control as They Grow
“I think as publications grow, then more structure or more editorial control is put in place, and we just seem to strike a really good balance.”
O'Hear: Cheap Listicles Subsidize Expensive Long-Form Journalism
“So, I don't know BuzzFeed's model entirely, but I would imagine that perhaps The listicles, in a sense, subsidize the long-form content, because the latter is much more expensive to produce.”
O'Hear: Citing Prior Press Coverage Is a Major Pitch Red Flag
“When someone says, hey, you should, like, cover my product or my startup, because we've just had coverage in, and then they list five other publications. That is probably the biggest red flag, you know, because we like to be first.”