StarZero All shows Try the podcast clipper →

Sep 4, 2017 · 24m · 20vc

20VC: True Ventures Founder, Phil Black on 4 Major Risk Categories for Startups, Why The Funding Gap Is At The "Rational B" Round & Why VCs Must Start Small But Think Big

Phil Black · 16m spoken Harry Stebbings · 7m 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 Twenty Minute VC, host Harry Stebbings interviews True Ventures co-founder Phil Black about navigating early-stage venture capital, managing risk, and building fund strategy. Phil breaks down the four core categories of startup risk, optimal capitalization strategies, and how True Ventures identifies high-potential opportunities in an evolving seed market.

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 30.1% of the talking time here. How this is scored →

Harry as informed peer 3.2 Guest teaching 3.0 Guest disagreement 1.2 Harry pushing back 2.4
05100:0010:0020:002:27–7:18 · Harry as informed peer 2/10 Phil Black's Entry into Venture Capital Harry introduces Phil's background and asks open-ended questions about his early career, dot-com bubble experiences, and running Blacksmith Capital. Phil provides educational background on financing risk and fiduciary duties without any host conflict.7:18–13:43 · Harry as informed peer 6/10 The Role and Mechanics of a Fund Manager Harry demonstrates solid industry knowledge by citing Jeff Clavier on runway lengths, Mike Maples on bridge rounds, and citing Namely as a counter-example. Phil educates on the fund manager lifecycle and breaks down the four risk categories of venture investing.13:44–19:04 · Harry as informed peer 5/10 Seed Landscape Evolution and True Ventures' Strategy Harry asks sharp questions about seed market inefficiencies and probes how True Ventures handles portfolio construction with growing AUM. Phil explains the 'rational B round' gap and clarifies True's ownership-focused strategy.19:04–22:42 · Harry as informed peer 3/10 Quick Fire Round with Phil Black A lighthearted quick-fire round covering convertible notes, books, mentors, and predictions. Phil candidly shares how his Jet.com prediction aged poorly when Walmart acquired it for three billion dollars.22:42–23:05 · Harry as informed peer 0/10 Interview Conclusion and Social Media Handles This brief concluding segment consists of episode wrap-up notes, social media plugs, and sponsor reads. Host-side and guest dynamic scores are zero as it is pure monologue.2:27–7:18 · Guest teaching 3/10 Phil Black's Entry into Venture Capital Harry introduces Phil's background and asks open-ended questions about his early career, dot-com bubble experiences, and running Blacksmith Capital. Phil provides educational background on financing risk and fiduciary duties without any host conflict.7:18–13:43 · Guest teaching 5/10 The Role and Mechanics of a Fund Manager Harry demonstrates solid industry knowledge by citing Jeff Clavier on runway lengths, Mike Maples on bridge rounds, and citing Namely as a counter-example. Phil educates on the fund manager lifecycle and breaks down the four risk categories of venture investing.13:44–19:04 · Guest teaching 4/10 Seed Landscape Evolution and True Ventures' Strategy Harry asks sharp questions about seed market inefficiencies and probes how True Ventures handles portfolio construction with growing AUM. Phil explains the 'rational B round' gap and clarifies True's ownership-focused strategy.19:04–22:42 · Guest teaching 3/10 Quick Fire Round with Phil Black A lighthearted quick-fire round covering convertible notes, books, mentors, and predictions. Phil candidly shares how his Jet.com prediction aged poorly when Walmart acquired it for three billion dollars.22:42–23:05 · Guest teaching 0/10 Interview Conclusion and Social Media Handles This brief concluding segment consists of episode wrap-up notes, social media plugs, and sponsor reads. Host-side and guest dynamic scores are zero as it is pure monologue.2:27–7:18 · Guest disagreement 1/10 Phil Black's Entry into Venture Capital Harry introduces Phil's background and asks open-ended questions about his early career, dot-com bubble experiences, and running Blacksmith Capital. Phil provides educational background on financing risk and fiduciary duties without any host conflict.7:18–13:43 · Guest disagreement 2/10 The Role and Mechanics of a Fund Manager Harry demonstrates solid industry knowledge by citing Jeff Clavier on runway lengths, Mike Maples on bridge rounds, and citing Namely as a counter-example. Phil educates on the fund manager lifecycle and breaks down the four risk categories of venture investing.13:44–19:04 · Guest disagreement 2/10 Seed Landscape Evolution and True Ventures' Strategy Harry asks sharp questions about seed market inefficiencies and probes how True Ventures handles portfolio construction with growing AUM. Phil explains the 'rational B round' gap and clarifies True's ownership-focused strategy.19:04–22:42 · Guest disagreement 1/10 Quick Fire Round with Phil Black A lighthearted quick-fire round covering convertible notes, books, mentors, and predictions. Phil candidly shares how his Jet.com prediction aged poorly when Walmart acquired it for three billion dollars.22:42–23:05 · Guest disagreement 0/10 Interview Conclusion and Social Media Handles This brief concluding segment consists of episode wrap-up notes, social media plugs, and sponsor reads. Host-side and guest dynamic scores are zero as it is pure monologue.2:27–7:18 · Harry pushing back 1/10 Phil Black's Entry into Venture Capital Harry introduces Phil's background and asks open-ended questions about his early career, dot-com bubble experiences, and running Blacksmith Capital. Phil provides educational background on financing risk and fiduciary duties without any host conflict.7:18–13:43 · Harry pushing back 5/10 The Role and Mechanics of a Fund Manager Harry demonstrates solid industry knowledge by citing Jeff Clavier on runway lengths, Mike Maples on bridge rounds, and citing Namely as a counter-example. Phil educates on the fund manager lifecycle and breaks down the four risk categories of venture investing.13:44–19:04 · Harry pushing back 4/10 Seed Landscape Evolution and True Ventures' Strategy Harry asks sharp questions about seed market inefficiencies and probes how True Ventures handles portfolio construction with growing AUM. Phil explains the 'rational B round' gap and clarifies True's ownership-focused strategy.19:04–22:42 · Harry pushing back 2/10 Quick Fire Round with Phil Black A lighthearted quick-fire round covering convertible notes, books, mentors, and predictions. Phil candidly shares how his Jet.com prediction aged poorly when Walmart acquired it for three billion dollars.22:42–23:05 · Harry pushing back 0/10 Interview Conclusion and Social Media Handles This brief concluding segment consists of episode wrap-up notes, social media plugs, and sponsor reads. Host-side and guest dynamic scores are zero as it is pure monologue.

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

0:00 · Harry 84.8% · guest 15.2%0:00 · Harry 84.8% · guest 15.2%3:00 · Harry 13.5% · guest 86.5%3:00 · Harry 13.5% · guest 86.5%6:00 · Harry 22.6% · guest 77.4%6:00 · Harry 22.6% · guest 77.4%9:00 · Harry 13.2% · guest 86.8%9:00 · Harry 13.2% · guest 86.8%12:00 · Harry 12.8% · guest 87.2%12:00 · Harry 12.8% · guest 87.2%15:00 · Harry 12.9% · guest 87.1%15:00 · Harry 12.9% · guest 87.1%18:00 · Harry 23.9% · guest 76.1%18:00 · Harry 23.9% · guest 76.1%21:00 · Harry 46.7% · guest 53.3%21:00 · Harry 46.7% · guest 53.3%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 11:14 Phil reframing bridge rounds

Phil counters the broad dismissal of bridge rounds by arguing that failed outcomes are labelled bridge notes in hindsight, explaining how short rounds like Namely's strategic tech buy differ.

 Hardest push from Harry ▶ 10:54 Harry pushing on bridge round failures

Harry actively pushes back against bridge rounds by citing Mike Maples' 'pier to nowhere' quote and presenting Namely as a specific counter-example to probe Phil's thesis.

 Biggest teaching moment ▶ 12:36 Phil breaking down four core VC risks

Phil systematically educates the host on the four core risk categories—market, product, execution, and financing—to explain exactly when a bridge round is viable versus fatal.

 Harry holds his own ▶ 18:06 Harry pressing on portfolio construction vs AUM

Harry demonstrates deep venture expertise by pressing Phil on whether small check sizes still make economic sense given True Ventures' increased assets under management.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Phil Black's Entry into Venture Capital 2311 Harry introduces Phil's background and asks open-ended questions about his early career, dot-com bubble experiences, and running Blacksmith Capital. Phil provides educational background on financing risk and fiduciary duties without any host conflict.
The Role and Mechanics of a Fund Manager 6525 Harry demonstrates solid industry knowledge by citing Jeff Clavier on runway lengths, Mike Maples on bridge rounds, and citing Namely as a counter-example. Phil educates on the fund manager lifecycle and breaks down the four risk categories of venture investing.
Seed Landscape Evolution and True Ventures' Strategy 5424 Harry asks sharp questions about seed market inefficiencies and probes how True Ventures handles portfolio construction with growing AUM. Phil explains the 'rational B round' gap and clarifies True's ownership-focused strategy.
Quick Fire Round with Phil Black 3312 A lighthearted quick-fire round covering convertible notes, books, mentors, and predictions. Phil candidly shares how his Jet.com prediction aged poorly when Walmart acquired it for three billion dollars.
Interview Conclusion and Social Media Handles 0000 This brief concluding segment consists of episode wrap-up notes, social media plugs, and sponsor reads. Host-side and guest dynamic scores are zero as it is pure monologue.

Statements from this episode (8)

Disclosure
Phil Black rounded his $4.64M angel fund to $5M to sound bigger
“Oh, it was 4.64 million dollars, and I rounded up to five million to make myself a You know, sound bigger.”
Phil Black Sep 4, 2017 ▶ 5:58
Insight
Founders spend large early rounds over 12 to 18 months regardless
“The problem with saying, well, we'll just raise a whole bunch more on the first round is that it's human nature. You don't divide that number by 36 and spend accordingly. You tend to just Divide that number again by that 12 or that 18. And so then you're spend…”
Phil Black Sep 4, 2017 ▶ 10:29
Insight
Bridge rounds work for product delays, not market or team failures
“If it really is, you know, it took a little longer for the product, but it's awesome. We just need three more months before we can have that customer traction. I think that the bridge round is probably going to be fine. If it's, well, we need six more months b…”
Phil Black Sep 4, 2017 ▶ 13:07
Assertion Not checkable as stated
The primary VC funding gap is the $3M to $7M Series B
“Right now in today's funding market, I, you know, to me, the gap that has been present for a while has been what we've referred to as the rational B round, you know, and that historically has been kind of a three to five, five to seven million dollar round of …”
Phil Black Sep 4, 2017 ▶ 16:01
Prediction Held up
True Ventures will never invest in another fitness step-counter startup
“We're never going to go after another fitness counter, a step counter kind of idea. That's old and in the market now.”
Phil Black Sep 4, 2017 ▶ 17:33
Opinion
Convertible notes and SAFEs are like alcohol: use only in moderation
“Oh, they're okay, but it's kind of like alcohol, and it should only be used in moderation.”
Phil Black Sep 4, 2017 ▶ 19:19
Disclosure
Phil Black named Jet.com, Zenefits, and Magic Leap as struggling unicorns
“So I had a Twitter post about this about, I don't know, nine months ago. And I said my three favorite unicorns that I think are in trouble were at that time, jet.com, Zenefits, and Magic Leap.”
Phil Black Sep 4, 2017 ▶ 20:50
What-if
Walmart could have bought Jet.com for one dollar by waiting
“That would have, they could have had that for a dollar if they just would have waited.”
Phil Black Sep 4, 2017 ▶ 21:17
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more