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Feb 18, 2015 · 26m · 20vc

20 VC 012: Angel Investing, Accelerators and AdTech with Clark Landry

Clark Landry · 18m spoken Harry Stebbings · 4m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, host Harry Stebbings interviews serial entrepreneur and angel investor Clark Landry to discuss his career in AdTech, the psychological realities of startup acquisitions, and his criteria for evaluating early-stage investments.

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 17.8% of the talking time here. How this is scored →

Harry as informed peer 2.0 Guest teaching 3.2 Guest disagreement 2.0 Harry pushing back 2.0
05100:0010:0020:000:45–4:48 · Harry as informed peer 1/10 Clark Landry's Entry into AdTech and Early Startup Successes Harry introduces Clark and asks about his entry into adtech and angel investing. Clark recounts his early days at iWin and Traffic Marketplace, detailing early web advertising arbitrage. Harry mostly listens with minimal follow-up on the dot-com bubble.4:50–8:12 · Harry as informed peer 2/10 Early Angel Investing and Founding Social Network TagWorld Harry asks whether exiting a startup feels like achievement or losing a baby. Clark reframes the experience, explaining that due diligence is so exhausting that exiting brings relief rather than emotional loss. The tone remains collaborative and reflective.8:14–12:24 · Harry as informed peer 3/10 Bridging Empathy Between Startup Founders and Venture Investors Clark discusses mutual empathy between founders and investors. Harry presses on whether empathy makes investors lenient when targets are missed, but Clark shuts down that assumption by clarifying that missing targets is never acceptable.12:24–18:08 · Harry as informed peer 2/10 Startup Evaluation Criteria, Co-Founder Dynamics, and Startup Failure Harry asks if failure is necessary for startup success. Clark rejects this popular Silicon Valley premise, explaining survivor bias and how media only interviews successful winners. Harry yields, admitting it was a strange question.18:10–25:32 · Harry as informed peer 2/10 Evolution of Advertising Technology and Operational Roles Harry moves into the quick-fire round, prompting Clark on books, accelerators, and recent investments like DSTLD. When Clark hesitates on tech accelerators, Harry presses him to name specific LA programs.0:45–4:48 · Guest teaching 2/10 Clark Landry's Entry into AdTech and Early Startup Successes Harry introduces Clark and asks about his entry into adtech and angel investing. Clark recounts his early days at iWin and Traffic Marketplace, detailing early web advertising arbitrage. Harry mostly listens with minimal follow-up on the dot-com bubble.4:50–8:12 · Guest teaching 3/10 Early Angel Investing and Founding Social Network TagWorld Harry asks whether exiting a startup feels like achievement or losing a baby. Clark reframes the experience, explaining that due diligence is so exhausting that exiting brings relief rather than emotional loss. The tone remains collaborative and reflective.8:14–12:24 · Guest teaching 4/10 Bridging Empathy Between Startup Founders and Venture Investors Clark discusses mutual empathy between founders and investors. Harry presses on whether empathy makes investors lenient when targets are missed, but Clark shuts down that assumption by clarifying that missing targets is never acceptable.12:24–18:08 · Guest teaching 5/10 Startup Evaluation Criteria, Co-Founder Dynamics, and Startup Failure Harry asks if failure is necessary for startup success. Clark rejects this popular Silicon Valley premise, explaining survivor bias and how media only interviews successful winners. Harry yields, admitting it was a strange question.18:10–25:32 · Guest teaching 2/10 Evolution of Advertising Technology and Operational Roles Harry moves into the quick-fire round, prompting Clark on books, accelerators, and recent investments like DSTLD. When Clark hesitates on tech accelerators, Harry presses him to name specific LA programs.0:45–4:48 · Guest disagreement 1/10 Clark Landry's Entry into AdTech and Early Startup Successes Harry introduces Clark and asks about his entry into adtech and angel investing. Clark recounts his early days at iWin and Traffic Marketplace, detailing early web advertising arbitrage. Harry mostly listens with minimal follow-up on the dot-com bubble.4:50–8:12 · Guest disagreement 1/10 Early Angel Investing and Founding Social Network TagWorld Harry asks whether exiting a startup feels like achievement or losing a baby. Clark reframes the experience, explaining that due diligence is so exhausting that exiting brings relief rather than emotional loss. The tone remains collaborative and reflective.8:14–12:24 · Guest disagreement 3/10 Bridging Empathy Between Startup Founders and Venture Investors Clark discusses mutual empathy between founders and investors. Harry presses on whether empathy makes investors lenient when targets are missed, but Clark shuts down that assumption by clarifying that missing targets is never acceptable.12:24–18:08 · Guest disagreement 4/10 Startup Evaluation Criteria, Co-Founder Dynamics, and Startup Failure Harry asks if failure is necessary for startup success. Clark rejects this popular Silicon Valley premise, explaining survivor bias and how media only interviews successful winners. Harry yields, admitting it was a strange question.18:10–25:32 · Guest disagreement 1/10 Evolution of Advertising Technology and Operational Roles Harry moves into the quick-fire round, prompting Clark on books, accelerators, and recent investments like DSTLD. When Clark hesitates on tech accelerators, Harry presses him to name specific LA programs.0:45–4:48 · Harry pushing back 1/10 Clark Landry's Entry into AdTech and Early Startup Successes Harry introduces Clark and asks about his entry into adtech and angel investing. Clark recounts his early days at iWin and Traffic Marketplace, detailing early web advertising arbitrage. Harry mostly listens with minimal follow-up on the dot-com bubble.4:50–8:12 · Harry pushing back 1/10 Early Angel Investing and Founding Social Network TagWorld Harry asks whether exiting a startup feels like achievement or losing a baby. Clark reframes the experience, explaining that due diligence is so exhausting that exiting brings relief rather than emotional loss. The tone remains collaborative and reflective.8:14–12:24 · Harry pushing back 4/10 Bridging Empathy Between Startup Founders and Venture Investors Clark discusses mutual empathy between founders and investors. Harry presses on whether empathy makes investors lenient when targets are missed, but Clark shuts down that assumption by clarifying that missing targets is never acceptable.12:24–18:08 · Harry pushing back 2/10 Startup Evaluation Criteria, Co-Founder Dynamics, and Startup Failure Harry asks if failure is necessary for startup success. Clark rejects this popular Silicon Valley premise, explaining survivor bias and how media only interviews successful winners. Harry yields, admitting it was a strange question.18:10–25:32 · Harry pushing back 2/10 Evolution of Advertising Technology and Operational Roles Harry moves into the quick-fire round, prompting Clark on books, accelerators, and recent investments like DSTLD. When Clark hesitates on tech accelerators, Harry presses him to name specific LA programs.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 26.1% · guest 73.9%0:00 · Harry 26.1% · guest 73.9%3:00 · Harry 10.7% · guest 89.3%3:00 · Harry 10.7% · guest 89.3%6:00 · Harry 20.9% · guest 79.1%6:00 · Harry 20.9% · guest 79.1%9:00 · Harry 14% · guest 86%9:00 · Harry 14% · guest 86%12:00 · Harry 18.2% · guest 81.8%12:00 · Harry 18.2% · guest 81.8%15:00 · Harry 12.2% · guest 87.8%15:00 · Harry 12.2% · guest 87.8%18:00 · Harry 21.3% · guest 78.7%18:00 · Harry 21.3% · guest 78.7%21:00 · Harry 11.4% · guest 88.6%21:00 · Harry 11.4% · guest 88.6%24:00 · Harry 29.5% · guest 70.5%24:00 · Harry 29.5% · guest 70.5%
Sharpest disagreement ▶ 16:40 Rejection of Silicon Valley failure glorification

Clark explicitly disagrees with Harry's suggestion that failure is necessary for founders, pointing out survivor bias in media interviews.

 Hardest push from Harry ▶ 10:36 Pressing on investor patience regarding missed targets

Harry interrupts Clark's monologue on investor empathy to press whether empathy translates into tolerance when financial targets are missed.

 Biggest teaching moment ▶ 16:40 Explaining survivor bias in tech failure narratives

Clark educates Harry on how public narratives around failure are skewed because media outlets only interview winning entrepreneurs.

 Harry holds his own ▶ 10:36 Formulating precise investor mindset hypothesis

Harry demonstrates domain insight by steering the conversation to how prior founder experience impacts an investor's operational tolerance.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Clark Landry's Entry into AdTech and Early Startup Successes 1211 Harry introduces Clark and asks about his entry into adtech and angel investing. Clark recounts his early days at iWin and Traffic Marketplace, detailing early web advertising arbitrage. Harry mostly listens with minimal follow-up on the dot-com bubble.
Early Angel Investing and Founding Social Network TagWorld 2311 Harry asks whether exiting a startup feels like achievement or losing a baby. Clark reframes the experience, explaining that due diligence is so exhausting that exiting brings relief rather than emotional loss. The tone remains collaborative and reflective.
Bridging Empathy Between Startup Founders and Venture Investors 3434 Clark discusses mutual empathy between founders and investors. Harry presses on whether empathy makes investors lenient when targets are missed, but Clark shuts down that assumption by clarifying that missing targets is never acceptable.
Startup Evaluation Criteria, Co-Founder Dynamics, and Startup Failure 2542 Harry asks if failure is necessary for startup success. Clark rejects this popular Silicon Valley premise, explaining survivor bias and how media only interviews successful winners. Harry yields, admitting it was a strange question.
Evolution of Advertising Technology and Operational Roles 2212 Harry moves into the quick-fire round, prompting Clark on books, accelerators, and recent investments like DSTLD. When Clark hesitates on tech accelerators, Harry presses him to name specific LA programs.

Statements from this episode (8)

Assertion Not checkable as stated
Modern ad arbitrage requires Wall Street-style black-box trading systems
“I mean, at this point, you know, if you want to try and do internet arbitrage you know, most of the most successful guys are using, I mean, Borderline Wall Street style, like, black box trading systems. Back then, you could literally go on a commission junctio…”
Clark Landry Feb 18, 2015 ▶ 2:27
Insight
Startup exits feel more like relief than pure celebration
“I think before you do a startup, you always envision that there's this moment where, you know, everyone is jumping up and down and celebrating, and at least in my experience, it's been, you know, it's obviously very exciting to be involved in a company that ge…”
Clark Landry Feb 18, 2015 ▶ 7:16
Insight
Founders with empathy for investors make delivering returns their top priority
“So I'd say as an entrepreneur, you have a lot more empathy for your investors, and you really get to the point where you want to You know, do well by them, and that, that becomes a very, very high priority, if not your top priority.”
Clark Landry Feb 18, 2015 ▶ 10:03
Insight
Investors should offer active support to struggling portfolio companies
“Even if you might be upset about, you know, maybe one of the companies you invested in, you know, had a bad quarter, a bad half, or a bad year and, you know, it doesn't make it any less concerning, but, you know, I've found myself just trying to get more in th…”
Clark Landry Feb 18, 2015 ▶ 11:36
Insight
Founding team quality matters more than the product for early-stage investments
“That's the most important thing for me is just the founding team over product.”
Clark Landry Feb 18, 2015 ▶ 13:03
Disclosure
Clark Landry prefers investing in multi-founder startups over solo founders
“I mean, I much prefer deals where there are multiple founders .”
Clark Landry Feb 18, 2015 ▶ 14:25
Opinion
Experiencing startup failure is not necessary for entrepreneurial success
“I, I'd say having to fail is not necessarily something that, that is a good thing necessarily.”
Clark Landry Feb 18, 2015 ▶ 17:47
Opinion
Launchpad, Amplify, and Mucker are the top tech accelerators in Los Angeles
“The Launchpad's great. I like Amplify a lot. Mucker is great. Making sure I don't leave any out from before I get yelled at. I think those three are some of the top ones in town.”
Clark Landry Feb 18, 2015 ▶ 21:49
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