Oct 14, 2024 · 1h 30m · news

David Frankel, MP @Founder Collective: Investing Lessons from Seeding Coupang, Pillpack & Suno|E1214 · 20VC with Harry Stebbings

David Frankel · 1h 4m spoken Harry Stebbings · 16m spoken
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In this episode of the 20VC podcast, host Harry Stebbings interviews David Frankel, Managing Partner at Founder Collective, to dissect the mechanics of disciplined seed investing, contrarian deal-making, reserve strategies, and the operational realities of supporting founders.

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 20.8% of the talking time here. How this is scored →

Harry as informed peer 4.9 Guest teaching 4.9 Guest disagreement 3.4 Harry pushing back 3.5
05100:0020:0040:001:00:001:20:000:39–5:47 · Harry as informed peer 5/10 In-Person Welcome & Seed Round Sizing Concerns Harry challenges David's rule-breaking $100k check in a high-valuation AI deal. When David mentions his partners criticized the decision as foolish, Harry pushes back strongly, arguing the brand signaling of backing a category winner like Suno justifies the price.5:47–9:28 · Harry as informed peer 4/10 The Illusion of Brand Name VCs and Being Orphaned Harry posits that VCs know within three months whether a portfolio company will succeed. David reframes the premise by contrasting consumer feedback velocity with enterprise SaaS, citing Olo to illustrate how enterprise turnarounds require extreme patience.9:28–13:16 · Harry as informed peer 6/10 Why Harry Hates Reserves & Saving The Trade Desk Harry forcefully states his strategy of zero reserves, citing losses in Hopin and Clubhouse. David counters by demonstrating how breaking Fund 1's no-reserve rule to follow on into The Trade Desk saved the company and generated enormous fund returns.13:16–17:31 · Harry as informed peer 4/10 Delivering Hard Feedback & The Cash-Burning Treadmill Harry asks about giving hard feedback to struggling founders. David explicitly rejects Jason Lemkin's view that feedback is futile, sharing how he confronted Running Tide's founder about cash burn prior to shutdown.17:31–20:06 · Harry as informed peer 5/10 Pro Rata Rights: VCs' Free Option on Founders Harry critiques pro rata rights as a lazy default for venture funds. David strongly agrees, labeling pro rata as the original sin against entrepreneurs because it acts as a free option that creates stalking horses.20:06–23:28 · Harry as informed peer 5/10 Stalking Horses and the Danger of Transactional Founders Harry and David discuss founder transactionality in fundraising. David details preferred stock mechanics, illustrating how heavy preferred stacks in late rounds turn early preferred shares into effective common stock.23:28–26:53 · Harry as informed peer 5/10 SaaS Multiples Drop and the Monthly Burn Rule David explains why 2018-vintage funds are struggling to produce DPI due to Zerp-era overvaluation. He educates on how private equity buyers are now restructuring M&A via rolling liquidation preferences.26:53–30:45 · Harry as informed peer 6/10 Opening the IPO Floodgates for LP Liquidity Harry pushes back on the DPI narrative, suggesting funds face permanent capital loss rather than a mere liquidity delay. David reframes fund return dynamics, explaining how multiple $100M-$250M exits reliably return sub-$100M seed funds.30:45–34:36 · Harry as informed peer 7/10 The Tyranny of Fund Size: Why Smaller Seed Funds Win Harry demonstrates deep knowledge of LP allocation models, criticizing institutional investors for attempting to replicate Yale's Swanson model in illiquid venture markets without appropriate hit rates.34:36–37:42 · Harry as informed peer 4/10 Navigating Secondary Markets, Down Rounds, and VC 'Quiet Quitting' Harry asks about secondary illiquidity and whether VCs are quiet quitting on plateaued companies. David candidly acknowledges that investors disengage when commercial momentum stalls.37:42–40:28 · Harry as informed peer 4/10 IPO Liquidation Strategies and Selling Moat Companies Harry asks about IPO exit execution frameworks. David details WeatherGage CIO Tim Blyamptus's advice that post-IPO selling decisions are always second-guessed, expressing regret over selling moat companies like Uber early.40:28–43:47 · Harry as informed peer 4/10 LEACH Legacy Companies and the Ticketmaster Monopoly David introduces his LEACH framework for legacy monopolies and describes giving formal testimony to the DOJ regarding Ticketmaster's anti-competitive pressure on venues. Harry declares he avoids investing against monopolistic moats.43:47–47:48 · Harry as informed peer 5/10 The VC War Playbook for Defeating Incumbents in the AI Era Harry suggests startups battling entrenched incumbents like Live Nation or Booking almost always lose. David forcefully rejects the premise, pointing to Suno AI and outlining the multi-front VC war playbook required to defeat incumbents.47:48–53:10 · Harry as informed peer 7/10 Capital Efficiency vs. Hyperscale Capital in the AI Era Harry demonstrates strong investment discipline by detailing his early meeting with Mistral AI, explaining why he passed on a $250M pre seed round due to ownership math and dilution models.53:10–57:47 · Harry as informed peer 5/10 AI Market Dynamics, Humility, and the 10x Underwriting Rule Harry praises David's extraordinary hit rate across tech cycles. David diffuses the compliment by crediting partner Eric Paley's strict 10x underwriting heuristic and recalling Eric's intellectual humility regarding Uber's unpredictable rise.57:47–1:02:29 · Harry as informed peer 5/10 Downside Protection, Risk-Taking, and the Red/Green Button Framework Harry quotes Index partner Shardul Shah regarding low loss ratios. David responds by detailing Josh Kopelman's red-button versus green-button founder test and arguing that VCs who don't lose money aren't taking enough risk.1:02:29–1:05:51 · Harry as informed peer 6/10 Founder Secondaries and the 'Sin' of Overfunding Harry vents against growth investors who forced excessive capital onto founders during the bull market and now criticize secondary liquidity. David validates the frustration, sharing an example where a founder was offered $20M on $80M in a single phone call.1:05:51–1:10:18 · Harry as informed peer 6/10 The Future of Vertical SaaS, Data Enrichment, and AI Pricing Power Harry cites Canva's 300% price increase and quotes David Friedberg on AI killing vertical SaaS. David rejects Friedberg's view, drawing on his past experience building an ISP to explain why customer inertia prevents internal tech replacement.1:10:18–1:12:46 · Harry as informed peer 4/10 Board Effectiveness, Economic Alignment, and Seed-Stage Dilution Harry asks how to excel as a board member. David stresses that board service requires at least 15% economic fund alignment to ensure patient, long-term dedication to the founder.1:12:46–1:16:31 · Harry as informed peer 4/10 VC Value Add, Portfolio Frauds, and a Wild Bankruptcy Story Harry brings up Vinod Khosla's claim that 90% of VCs add negative value. David proves high value-add by recounting a portfolio company failure involving CFO suicide and KPMG fraud, where he voluntarily returned $4M in secondary proceeds on legal advice.1:16:31–1:18:37 · Harry as informed peer 4/10 The Role of Seed Funds as Matchmakers David explains that seed funds operate primarily as dedicated matchmaking engines for follow-on rounds, contrasting their incentives with multi-stage funds that hold competing internal priorities.1:18:37–1:22:52 · Harry as informed peer 5/10 The Art and Science of Testimonial Sales Harry dismisses TAM sizing at the seed stage, arguing that elite founders expand markets. David agrees, sharing how Bessemer rejected Media Radar due to print magazine TAM calculations before the company pivoted online and reached multi-billion value.1:22:52–1:25:49 · Harry as informed peer 4/10 Quick Fire: Private Equity, Board Members, and Sourcing Zoom In the quick-fire round, David praises Emergence partner Jake Saper for sourcing Zoom and delivering exceptional, hands-on support to portfolio companies.1:25:49–1:30:41 · Harry as informed peer 4/10 Quick Fire: ZERP Era, Non-Binary Decisions, and What Matters Most Harry asks David about his most difficult unmade decisions. David explains that critical venture choices are rarely 100% binary, requiring investors to act on 51% conviction while balancing intellect and visceral emotion.0:39–5:47 · Guest teaching 4/10 In-Person Welcome & Seed Round Sizing Concerns Harry challenges David's rule-breaking $100k check in a high-valuation AI deal. When David mentions his partners criticized the decision as foolish, Harry pushes back strongly, arguing the brand signaling of backing a category winner like Suno justifies the price.5:47–9:28 · Guest teaching 5/10 The Illusion of Brand Name VCs and Being Orphaned Harry posits that VCs know within three months whether a portfolio company will succeed. David reframes the premise by contrasting consumer feedback velocity with enterprise SaaS, citing Olo to illustrate how enterprise turnarounds require extreme patience.9:28–13:16 · Guest teaching 6/10 Why Harry Hates Reserves & Saving The Trade Desk Harry forcefully states his strategy of zero reserves, citing losses in Hopin and Clubhouse. David counters by demonstrating how breaking Fund 1's no-reserve rule to follow on into The Trade Desk saved the company and generated enormous fund returns.13:16–17:31 · Guest teaching 4/10 Delivering Hard Feedback & The Cash-Burning Treadmill Harry asks about giving hard feedback to struggling founders. David explicitly rejects Jason Lemkin's view that feedback is futile, sharing how he confronted Running Tide's founder about cash burn prior to shutdown.17:31–20:06 · Guest teaching 5/10 Pro Rata Rights: VCs' Free Option on Founders Harry critiques pro rata rights as a lazy default for venture funds. David strongly agrees, labeling pro rata as the original sin against entrepreneurs because it acts as a free option that creates stalking horses.20:06–23:28 · Guest teaching 5/10 Stalking Horses and the Danger of Transactional Founders Harry and David discuss founder transactionality in fundraising. David details preferred stock mechanics, illustrating how heavy preferred stacks in late rounds turn early preferred shares into effective common stock.23:28–26:53 · Guest teaching 6/10 SaaS Multiples Drop and the Monthly Burn Rule David explains why 2018-vintage funds are struggling to produce DPI due to Zerp-era overvaluation. He educates on how private equity buyers are now restructuring M&A via rolling liquidation preferences.26:53–30:45 · Guest teaching 6/10 Opening the IPO Floodgates for LP Liquidity Harry pushes back on the DPI narrative, suggesting funds face permanent capital loss rather than a mere liquidity delay. David reframes fund return dynamics, explaining how multiple $100M-$250M exits reliably return sub-$100M seed funds.30:45–34:36 · Guest teaching 4/10 The Tyranny of Fund Size: Why Smaller Seed Funds Win Harry demonstrates deep knowledge of LP allocation models, criticizing institutional investors for attempting to replicate Yale's Swanson model in illiquid venture markets without appropriate hit rates.34:36–37:42 · Guest teaching 4/10 Navigating Secondary Markets, Down Rounds, and VC 'Quiet Quitting' Harry asks about secondary illiquidity and whether VCs are quiet quitting on plateaued companies. David candidly acknowledges that investors disengage when commercial momentum stalls.37:42–40:28 · Guest teaching 5/10 IPO Liquidation Strategies and Selling Moat Companies Harry asks about IPO exit execution frameworks. David details WeatherGage CIO Tim Blyamptus's advice that post-IPO selling decisions are always second-guessed, expressing regret over selling moat companies like Uber early.40:28–43:47 · Guest teaching 6/10 LEACH Legacy Companies and the Ticketmaster Monopoly David introduces his LEACH framework for legacy monopolies and describes giving formal testimony to the DOJ regarding Ticketmaster's anti-competitive pressure on venues. Harry declares he avoids investing against monopolistic moats.43:47–47:48 · Guest teaching 6/10 The VC War Playbook for Defeating Incumbents in the AI Era Harry suggests startups battling entrenched incumbents like Live Nation or Booking almost always lose. David forcefully rejects the premise, pointing to Suno AI and outlining the multi-front VC war playbook required to defeat incumbents.47:48–53:10 · Guest teaching 4/10 Capital Efficiency vs. Hyperscale Capital in the AI Era Harry demonstrates strong investment discipline by detailing his early meeting with Mistral AI, explaining why he passed on a $250M pre seed round due to ownership math and dilution models.53:10–57:47 · Guest teaching 5/10 AI Market Dynamics, Humility, and the 10x Underwriting Rule Harry praises David's extraordinary hit rate across tech cycles. David diffuses the compliment by crediting partner Eric Paley's strict 10x underwriting heuristic and recalling Eric's intellectual humility regarding Uber's unpredictable rise.57:47–1:02:29 · Guest teaching 5/10 Downside Protection, Risk-Taking, and the Red/Green Button Framework Harry quotes Index partner Shardul Shah regarding low loss ratios. David responds by detailing Josh Kopelman's red-button versus green-button founder test and arguing that VCs who don't lose money aren't taking enough risk.1:02:29–1:05:51 · Guest teaching 4/10 Founder Secondaries and the 'Sin' of Overfunding Harry vents against growth investors who forced excessive capital onto founders during the bull market and now criticize secondary liquidity. David validates the frustration, sharing an example where a founder was offered $20M on $80M in a single phone call.1:05:51–1:10:18 · Guest teaching 6/10 The Future of Vertical SaaS, Data Enrichment, and AI Pricing Power Harry cites Canva's 300% price increase and quotes David Friedberg on AI killing vertical SaaS. David rejects Friedberg's view, drawing on his past experience building an ISP to explain why customer inertia prevents internal tech replacement.1:10:18–1:12:46 · Guest teaching 4/10 Board Effectiveness, Economic Alignment, and Seed-Stage Dilution Harry asks how to excel as a board member. David stresses that board service requires at least 15% economic fund alignment to ensure patient, long-term dedication to the founder.1:12:46–1:16:31 · Guest teaching 7/10 VC Value Add, Portfolio Frauds, and a Wild Bankruptcy Story Harry brings up Vinod Khosla's claim that 90% of VCs add negative value. David proves high value-add by recounting a portfolio company failure involving CFO suicide and KPMG fraud, where he voluntarily returned $4M in secondary proceeds on legal advice.1:16:31–1:18:37 · Guest teaching 4/10 The Role of Seed Funds as Matchmakers David explains that seed funds operate primarily as dedicated matchmaking engines for follow-on rounds, contrasting their incentives with multi-stage funds that hold competing internal priorities.1:18:37–1:22:52 · Guest teaching 5/10 The Art and Science of Testimonial Sales Harry dismisses TAM sizing at the seed stage, arguing that elite founders expand markets. David agrees, sharing how Bessemer rejected Media Radar due to print magazine TAM calculations before the company pivoted online and reached multi-billion value.1:22:52–1:25:49 · Guest teaching 4/10 Quick Fire: Private Equity, Board Members, and Sourcing Zoom In the quick-fire round, David praises Emergence partner Jake Saper for sourcing Zoom and delivering exceptional, hands-on support to portfolio companies.1:25:49–1:30:41 · Guest teaching 4/10 Quick Fire: ZERP Era, Non-Binary Decisions, and What Matters Most Harry asks David about his most difficult unmade decisions. David explains that critical venture choices are rarely 100% binary, requiring investors to act on 51% conviction while balancing intellect and visceral emotion.0:39–5:47 · Guest disagreement 4/10 In-Person Welcome & Seed Round Sizing Concerns Harry challenges David's rule-breaking $100k check in a high-valuation AI deal. When David mentions his partners criticized the decision as foolish, Harry pushes back strongly, arguing the brand signaling of backing a category winner like Suno justifies the price.5:47–9:28 · Guest disagreement 3/10 The Illusion of Brand Name VCs and Being Orphaned Harry posits that VCs know within three months whether a portfolio company will succeed. David reframes the premise by contrasting consumer feedback velocity with enterprise SaaS, citing Olo to illustrate how enterprise turnarounds require extreme patience.9:28–13:16 · Guest disagreement 4/10 Why Harry Hates Reserves & Saving The Trade Desk Harry forcefully states his strategy of zero reserves, citing losses in Hopin and Clubhouse. David counters by demonstrating how breaking Fund 1's no-reserve rule to follow on into The Trade Desk saved the company and generated enormous fund returns.13:16–17:31 · Guest disagreement 4/10 Delivering Hard Feedback & The Cash-Burning Treadmill Harry asks about giving hard feedback to struggling founders. David explicitly rejects Jason Lemkin's view that feedback is futile, sharing how he confronted Running Tide's founder about cash burn prior to shutdown.17:31–20:06 · Guest disagreement 4/10 Pro Rata Rights: VCs' Free Option on Founders Harry critiques pro rata rights as a lazy default for venture funds. David strongly agrees, labeling pro rata as the original sin against entrepreneurs because it acts as a free option that creates stalking horses.20:06–23:28 · Guest disagreement 4/10 Stalking Horses and the Danger of Transactional Founders Harry and David discuss founder transactionality in fundraising. David details preferred stock mechanics, illustrating how heavy preferred stacks in late rounds turn early preferred shares into effective common stock.23:28–26:53 · Guest disagreement 3/10 SaaS Multiples Drop and the Monthly Burn Rule David explains why 2018-vintage funds are struggling to produce DPI due to Zerp-era overvaluation. He educates on how private equity buyers are now restructuring M&A via rolling liquidation preferences.26:53–30:45 · Guest disagreement 4/10 Opening the IPO Floodgates for LP Liquidity Harry pushes back on the DPI narrative, suggesting funds face permanent capital loss rather than a mere liquidity delay. David reframes fund return dynamics, explaining how multiple $100M-$250M exits reliably return sub-$100M seed funds.30:45–34:36 · Guest disagreement 3/10 The Tyranny of Fund Size: Why Smaller Seed Funds Win Harry demonstrates deep knowledge of LP allocation models, criticizing institutional investors for attempting to replicate Yale's Swanson model in illiquid venture markets without appropriate hit rates.34:36–37:42 · Guest disagreement 3/10 Navigating Secondary Markets, Down Rounds, and VC 'Quiet Quitting' Harry asks about secondary illiquidity and whether VCs are quiet quitting on plateaued companies. David candidly acknowledges that investors disengage when commercial momentum stalls.37:42–40:28 · Guest disagreement 3/10 IPO Liquidation Strategies and Selling Moat Companies Harry asks about IPO exit execution frameworks. David details WeatherGage CIO Tim Blyamptus's advice that post-IPO selling decisions are always second-guessed, expressing regret over selling moat companies like Uber early.40:28–43:47 · Guest disagreement 3/10 LEACH Legacy Companies and the Ticketmaster Monopoly David introduces his LEACH framework for legacy monopolies and describes giving formal testimony to the DOJ regarding Ticketmaster's anti-competitive pressure on venues. Harry declares he avoids investing against monopolistic moats.43:47–47:48 · Guest disagreement 5/10 The VC War Playbook for Defeating Incumbents in the AI Era Harry suggests startups battling entrenched incumbents like Live Nation or Booking almost always lose. David forcefully rejects the premise, pointing to Suno AI and outlining the multi-front VC war playbook required to defeat incumbents.47:48–53:10 · Guest disagreement 3/10 Capital Efficiency vs. Hyperscale Capital in the AI Era Harry demonstrates strong investment discipline by detailing his early meeting with Mistral AI, explaining why he passed on a $250M pre seed round due to ownership math and dilution models.53:10–57:47 · Guest disagreement 3/10 AI Market Dynamics, Humility, and the 10x Underwriting Rule Harry praises David's extraordinary hit rate across tech cycles. David diffuses the compliment by crediting partner Eric Paley's strict 10x underwriting heuristic and recalling Eric's intellectual humility regarding Uber's unpredictable rise.57:47–1:02:29 · Guest disagreement 3/10 Downside Protection, Risk-Taking, and the Red/Green Button Framework Harry quotes Index partner Shardul Shah regarding low loss ratios. David responds by detailing Josh Kopelman's red-button versus green-button founder test and arguing that VCs who don't lose money aren't taking enough risk.1:02:29–1:05:51 · Guest disagreement 3/10 Founder Secondaries and the 'Sin' of Overfunding Harry vents against growth investors who forced excessive capital onto founders during the bull market and now criticize secondary liquidity. David validates the frustration, sharing an example where a founder was offered $20M on $80M in a single phone call.1:05:51–1:10:18 · Guest disagreement 5/10 The Future of Vertical SaaS, Data Enrichment, and AI Pricing Power Harry cites Canva's 300% price increase and quotes David Friedberg on AI killing vertical SaaS. David rejects Friedberg's view, drawing on his past experience building an ISP to explain why customer inertia prevents internal tech replacement.1:10:18–1:12:46 · Guest disagreement 3/10 Board Effectiveness, Economic Alignment, and Seed-Stage Dilution Harry asks how to excel as a board member. David stresses that board service requires at least 15% economic fund alignment to ensure patient, long-term dedication to the founder.1:12:46–1:16:31 · Guest disagreement 4/10 VC Value Add, Portfolio Frauds, and a Wild Bankruptcy Story Harry brings up Vinod Khosla's claim that 90% of VCs add negative value. David proves high value-add by recounting a portfolio company failure involving CFO suicide and KPMG fraud, where he voluntarily returned $4M in secondary proceeds on legal advice.1:16:31–1:18:37 · Guest disagreement 3/10 The Role of Seed Funds as Matchmakers David explains that seed funds operate primarily as dedicated matchmaking engines for follow-on rounds, contrasting their incentives with multi-stage funds that hold competing internal priorities.1:18:37–1:22:52 · Guest disagreement 3/10 The Art and Science of Testimonial Sales Harry dismisses TAM sizing at the seed stage, arguing that elite founders expand markets. David agrees, sharing how Bessemer rejected Media Radar due to print magazine TAM calculations before the company pivoted online and reached multi-billion value.1:22:52–1:25:49 · Guest disagreement 2/10 Quick Fire: Private Equity, Board Members, and Sourcing Zoom In the quick-fire round, David praises Emergence partner Jake Saper for sourcing Zoom and delivering exceptional, hands-on support to portfolio companies.1:25:49–1:30:41 · Guest disagreement 2/10 Quick Fire: ZERP Era, Non-Binary Decisions, and What Matters Most Harry asks David about his most difficult unmade decisions. David explains that critical venture choices are rarely 100% binary, requiring investors to act on 51% conviction while balancing intellect and visceral emotion.0:39–5:47 · Harry pushing back 6/10 In-Person Welcome & Seed Round Sizing Concerns Harry challenges David's rule-breaking $100k check in a high-valuation AI deal. When David mentions his partners criticized the decision as foolish, Harry pushes back strongly, arguing the brand signaling of backing a category winner like Suno justifies the price.5:47–9:28 · Harry pushing back 3/10 The Illusion of Brand Name VCs and Being Orphaned Harry posits that VCs know within three months whether a portfolio company will succeed. David reframes the premise by contrasting consumer feedback velocity with enterprise SaaS, citing Olo to illustrate how enterprise turnarounds require extreme patience.9:28–13:16 · Harry pushing back 6/10 Why Harry Hates Reserves & Saving The Trade Desk Harry forcefully states his strategy of zero reserves, citing losses in Hopin and Clubhouse. David counters by demonstrating how breaking Fund 1's no-reserve rule to follow on into The Trade Desk saved the company and generated enormous fund returns.13:16–17:31 · Harry pushing back 3/10 Delivering Hard Feedback & The Cash-Burning Treadmill Harry asks about giving hard feedback to struggling founders. David explicitly rejects Jason Lemkin's view that feedback is futile, sharing how he confronted Running Tide's founder about cash burn prior to shutdown.17:31–20:06 · Harry pushing back 2/10 Pro Rata Rights: VCs' Free Option on Founders Harry critiques pro rata rights as a lazy default for venture funds. David strongly agrees, labeling pro rata as the original sin against entrepreneurs because it acts as a free option that creates stalking horses.20:06–23:28 · Harry pushing back 3/10 Stalking Horses and the Danger of Transactional Founders Harry and David discuss founder transactionality in fundraising. David details preferred stock mechanics, illustrating how heavy preferred stacks in late rounds turn early preferred shares into effective common stock.23:28–26:53 · Harry pushing back 2/10 SaaS Multiples Drop and the Monthly Burn Rule David explains why 2018-vintage funds are struggling to produce DPI due to Zerp-era overvaluation. He educates on how private equity buyers are now restructuring M&A via rolling liquidation preferences.26:53–30:45 · Harry pushing back 5/10 Opening the IPO Floodgates for LP Liquidity Harry pushes back on the DPI narrative, suggesting funds face permanent capital loss rather than a mere liquidity delay. David reframes fund return dynamics, explaining how multiple $100M-$250M exits reliably return sub-$100M seed funds.30:45–34:36 · Harry pushing back 5/10 The Tyranny of Fund Size: Why Smaller Seed Funds Win Harry demonstrates deep knowledge of LP allocation models, criticizing institutional investors for attempting to replicate Yale's Swanson model in illiquid venture markets without appropriate hit rates.34:36–37:42 · Harry pushing back 3/10 Navigating Secondary Markets, Down Rounds, and VC 'Quiet Quitting' Harry asks about secondary illiquidity and whether VCs are quiet quitting on plateaued companies. David candidly acknowledges that investors disengage when commercial momentum stalls.37:42–40:28 · Harry pushing back 2/10 IPO Liquidation Strategies and Selling Moat Companies Harry asks about IPO exit execution frameworks. David details WeatherGage CIO Tim Blyamptus's advice that post-IPO selling decisions are always second-guessed, expressing regret over selling moat companies like Uber early.40:28–43:47 · Harry pushing back 4/10 LEACH Legacy Companies and the Ticketmaster Monopoly David introduces his LEACH framework for legacy monopolies and describes giving formal testimony to the DOJ regarding Ticketmaster's anti-competitive pressure on venues. Harry declares he avoids investing against monopolistic moats.43:47–47:48 · Harry pushing back 5/10 The VC War Playbook for Defeating Incumbents in the AI Era Harry suggests startups battling entrenched incumbents like Live Nation or Booking almost always lose. David forcefully rejects the premise, pointing to Suno AI and outlining the multi-front VC war playbook required to defeat incumbents.47:48–53:10 · Harry pushing back 4/10 Capital Efficiency vs. Hyperscale Capital in the AI Era Harry demonstrates strong investment discipline by detailing his early meeting with Mistral AI, explaining why he passed on a $250M pre seed round due to ownership math and dilution models.53:10–57:47 · Harry pushing back 3/10 AI Market Dynamics, Humility, and the 10x Underwriting Rule Harry praises David's extraordinary hit rate across tech cycles. David diffuses the compliment by crediting partner Eric Paley's strict 10x underwriting heuristic and recalling Eric's intellectual humility regarding Uber's unpredictable rise.57:47–1:02:29 · Harry pushing back 4/10 Downside Protection, Risk-Taking, and the Red/Green Button Framework Harry quotes Index partner Shardul Shah regarding low loss ratios. David responds by detailing Josh Kopelman's red-button versus green-button founder test and arguing that VCs who don't lose money aren't taking enough risk.1:02:29–1:05:51 · Harry pushing back 4/10 Founder Secondaries and the 'Sin' of Overfunding Harry vents against growth investors who forced excessive capital onto founders during the bull market and now criticize secondary liquidity. David validates the frustration, sharing an example where a founder was offered $20M on $80M in a single phone call.1:05:51–1:10:18 · Harry pushing back 4/10 The Future of Vertical SaaS, Data Enrichment, and AI Pricing Power Harry cites Canva's 300% price increase and quotes David Friedberg on AI killing vertical SaaS. David rejects Friedberg's view, drawing on his past experience building an ISP to explain why customer inertia prevents internal tech replacement.1:10:18–1:12:46 · Harry pushing back 2/10 Board Effectiveness, Economic Alignment, and Seed-Stage Dilution Harry asks how to excel as a board member. David stresses that board service requires at least 15% economic fund alignment to ensure patient, long-term dedication to the founder.1:12:46–1:16:31 · Harry pushing back 3/10 VC Value Add, Portfolio Frauds, and a Wild Bankruptcy Story Harry brings up Vinod Khosla's claim that 90% of VCs add negative value. David proves high value-add by recounting a portfolio company failure involving CFO suicide and KPMG fraud, where he voluntarily returned $4M in secondary proceeds on legal advice.1:16:31–1:18:37 · Harry pushing back 2/10 The Role of Seed Funds as Matchmakers David explains that seed funds operate primarily as dedicated matchmaking engines for follow-on rounds, contrasting their incentives with multi-stage funds that hold competing internal priorities.1:18:37–1:22:52 · Harry pushing back 4/10 The Art and Science of Testimonial Sales Harry dismisses TAM sizing at the seed stage, arguing that elite founders expand markets. David agrees, sharing how Bessemer rejected Media Radar due to print magazine TAM calculations before the company pivoted online and reached multi-billion value.1:22:52–1:25:49 · Harry pushing back 2/10 Quick Fire: Private Equity, Board Members, and Sourcing Zoom In the quick-fire round, David praises Emergence partner Jake Saper for sourcing Zoom and delivering exceptional, hands-on support to portfolio companies.1:25:49–1:30:41 · Harry pushing back 2/10 Quick Fire: ZERP Era, Non-Binary Decisions, and What Matters Most Harry asks David about his most difficult unmade decisions. David explains that critical venture choices are rarely 100% binary, requiring investors to act on 51% conviction while balancing intellect and visceral emotion.

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

0:00 · Harry 19.4% · guest 80.6%0:00 · Harry 19.4% · guest 80.6%3:00 · Harry 24.9% · guest 75.1%3:00 · Harry 24.9% · guest 75.1%6:00 · Harry 14.9% · guest 85.1%6:00 · Harry 14.9% · guest 85.1%9:00 · Harry 38.9% · guest 61.1%9:00 · Harry 38.9% · guest 61.1%12:00 · Harry 24.2% · guest 75.8%12:00 · Harry 24.2% · guest 75.8%15:00 · Harry 21.9% · guest 78.1%15:00 · Harry 21.9% · guest 78.1%18:00 · Harry 16.7% · guest 83.3%18:00 · Harry 16.7% · guest 83.3%21:00 · Harry 19.2% · guest 80.8%21:00 · Harry 19.2% · guest 80.8%24:00 · Harry 6.8% · guest 93.2%24:00 · Harry 6.8% · guest 93.2%27:00 · Harry 25.9% · guest 74.1%27:00 · Harry 25.9% · guest 74.1%30:00 · Harry 25.5% · guest 74.5%30:00 · Harry 25.5% · guest 74.5%33:00 · Harry 34.2% · guest 65.8%33:00 · Harry 34.2% · guest 65.8%36:00 · Harry 19% · guest 81%36:00 · Harry 19% · guest 81%39:00 · Harry 12.6% · guest 87.4%39:00 · Harry 12.6% · guest 87.4%42:00 · Harry 15.7% · guest 84.3%42:00 · Harry 15.7% · guest 84.3%45:00 · Harry 21.8% · guest 78.2%45:00 · Harry 21.8% · guest 78.2%48:00 · Harry 26% · guest 74%48:00 · Harry 26% · guest 74%51:00 · Harry 12.9% · guest 87.1%51:00 · Harry 12.9% · guest 87.1%54:00 · Harry 28.3% · guest 71.7%54:00 · Harry 28.3% · guest 71.7%57:00 · Harry 23.2% · guest 76.8%57:00 · Harry 23.2% · guest 76.8%1:00:00 · Harry 22.8% · guest 77.2%1:00:00 · Harry 22.8% · guest 77.2%1:03:00 · Harry 18.8% · guest 81.2%1:03:00 · Harry 18.8% · guest 81.2%1:06:00 · Harry 30.4% · guest 69.6%1:06:00 · Harry 30.4% · guest 69.6%1:09:00 · Harry 21.3% · guest 78.7%1:09:00 · Harry 21.3% · guest 78.7%1:12:00 · Harry 10.4% · guest 89.6%1:12:00 · Harry 10.4% · guest 89.6%1:15:00 · Harry 7.2% · guest 92.8%1:15:00 · Harry 7.2% · guest 92.8%1:18:00 · Harry 27.4% · guest 72.6%1:18:00 · Harry 27.4% · guest 72.6%1:21:00 · Harry 27.6% · guest 72.4%1:21:00 · Harry 27.6% · guest 72.4%1:24:00 · Harry 18.6% · guest 81.4%1:24:00 · Harry 18.6% · guest 81.4%1:27:00 · Harry 6.5% · guest 93.5%1:27:00 · Harry 6.5% · guest 93.5%1:30:00 · Harry 22.9% · guest 77.1%1:30:00 · Harry 22.9% · guest 77.1%
Sharpest disagreement ▶ 46:19 David rejects Harry's claim that disruptors always lose to monopolistic incumbents

David forcefully refutes Harry's defeatist assertion that startups cannot defeat monopolistic incumbents, declaring 'there's no fun in entrepreneurship if you believe that' and pointing to Suno AI as proof.

Hardest push from Harry ▶ 4:28 Harry challenges David's partners' criticism of writing $100k checks in hype rounds

Harry refuses to accept David's partners' framing that writing a small check in a high-priced AI round was foolish, arguing forcefully that securing a stake in a category-defining winner like Suno yields critical brand value for future deal sourcing.

Biggest teaching moment ▶ 1:14:28 David details navigating a KPMG portfolio fraud and returning secondary funds

David educates Harry on extreme crisis management by recounting a catastrophic portfolio fraud involving CFO suicide, KPMG forgery, and his choice to voluntarily return $4M in secondary payouts on expert bankruptcy advice.

Harry holds his own ▶ 50:18 Harry explains passing on Mistral AI based on seed fund ownership math

Harry demonstrates high domain mastery by recounting his early meeting with Mistral AI and laying out the precise dilution and return models that led him to pass on a $250M valuation seed round.

the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
In-Person Welcome & Seed Round Sizing Concerns 5446 Harry challenges David's rule-breaking $100k check in a high-valuation AI deal. When David mentions his partners criticized the decision as foolish, Harry pushes back strongly, arguing the brand signaling of backing a category winner like Suno justifies the price.
The Illusion of Brand Name VCs and Being Orphaned 4533 Harry posits that VCs know within three months whether a portfolio company will succeed. David reframes the premise by contrasting consumer feedback velocity with enterprise SaaS, citing Olo to illustrate how enterprise turnarounds require extreme patience.
Why Harry Hates Reserves & Saving The Trade Desk 6646 Harry forcefully states his strategy of zero reserves, citing losses in Hopin and Clubhouse. David counters by demonstrating how breaking Fund 1's no-reserve rule to follow on into The Trade Desk saved the company and generated enormous fund returns.
Delivering Hard Feedback & The Cash-Burning Treadmill 4443 Harry asks about giving hard feedback to struggling founders. David explicitly rejects Jason Lemkin's view that feedback is futile, sharing how he confronted Running Tide's founder about cash burn prior to shutdown.
Pro Rata Rights: VCs' Free Option on Founders 5542 Harry critiques pro rata rights as a lazy default for venture funds. David strongly agrees, labeling pro rata as the original sin against entrepreneurs because it acts as a free option that creates stalking horses.
Stalking Horses and the Danger of Transactional Founders 5543 Harry and David discuss founder transactionality in fundraising. David details preferred stock mechanics, illustrating how heavy preferred stacks in late rounds turn early preferred shares into effective common stock.
SaaS Multiples Drop and the Monthly Burn Rule 5632 David explains why 2018-vintage funds are struggling to produce DPI due to Zerp-era overvaluation. He educates on how private equity buyers are now restructuring M&A via rolling liquidation preferences.
Opening the IPO Floodgates for LP Liquidity 6645 Harry pushes back on the DPI narrative, suggesting funds face permanent capital loss rather than a mere liquidity delay. David reframes fund return dynamics, explaining how multiple $100M-$250M exits reliably return sub-$100M seed funds.
The Tyranny of Fund Size: Why Smaller Seed Funds Win 7435 Harry demonstrates deep knowledge of LP allocation models, criticizing institutional investors for attempting to replicate Yale's Swanson model in illiquid venture markets without appropriate hit rates.
Navigating Secondary Markets, Down Rounds, and VC 'Quiet Quitting' 4433 Harry asks about secondary illiquidity and whether VCs are quiet quitting on plateaued companies. David candidly acknowledges that investors disengage when commercial momentum stalls.
IPO Liquidation Strategies and Selling Moat Companies 4532 Harry asks about IPO exit execution frameworks. David details WeatherGage CIO Tim Blyamptus's advice that post-IPO selling decisions are always second-guessed, expressing regret over selling moat companies like Uber early.
LEACH Legacy Companies and the Ticketmaster Monopoly 4634 David introduces his LEACH framework for legacy monopolies and describes giving formal testimony to the DOJ regarding Ticketmaster's anti-competitive pressure on venues. Harry declares he avoids investing against monopolistic moats.
The VC War Playbook for Defeating Incumbents in the AI Era 5655 Harry suggests startups battling entrenched incumbents like Live Nation or Booking almost always lose. David forcefully rejects the premise, pointing to Suno AI and outlining the multi-front VC war playbook required to defeat incumbents.
Capital Efficiency vs. Hyperscale Capital in the AI Era 7434 Harry demonstrates strong investment discipline by detailing his early meeting with Mistral AI, explaining why he passed on a $250M pre seed round due to ownership math and dilution models.
AI Market Dynamics, Humility, and the 10x Underwriting Rule 5533 Harry praises David's extraordinary hit rate across tech cycles. David diffuses the compliment by crediting partner Eric Paley's strict 10x underwriting heuristic and recalling Eric's intellectual humility regarding Uber's unpredictable rise.
Downside Protection, Risk-Taking, and the Red/Green Button Framework 5534 Harry quotes Index partner Shardul Shah regarding low loss ratios. David responds by detailing Josh Kopelman's red-button versus green-button founder test and arguing that VCs who don't lose money aren't taking enough risk.
Founder Secondaries and the 'Sin' of Overfunding 6434 Harry vents against growth investors who forced excessive capital onto founders during the bull market and now criticize secondary liquidity. David validates the frustration, sharing an example where a founder was offered $20M on $80M in a single phone call.
The Future of Vertical SaaS, Data Enrichment, and AI Pricing Power 6654 Harry cites Canva's 300% price increase and quotes David Friedberg on AI killing vertical SaaS. David rejects Friedberg's view, drawing on his past experience building an ISP to explain why customer inertia prevents internal tech replacement.
Board Effectiveness, Economic Alignment, and Seed-Stage Dilution 4432 Harry asks how to excel as a board member. David stresses that board service requires at least 15% economic fund alignment to ensure patient, long-term dedication to the founder.
VC Value Add, Portfolio Frauds, and a Wild Bankruptcy Story 4743 Harry brings up Vinod Khosla's claim that 90% of VCs add negative value. David proves high value-add by recounting a portfolio company failure involving CFO suicide and KPMG fraud, where he voluntarily returned $4M in secondary proceeds on legal advice.
The Role of Seed Funds as Matchmakers 4432 David explains that seed funds operate primarily as dedicated matchmaking engines for follow-on rounds, contrasting their incentives with multi-stage funds that hold competing internal priorities.
The Art and Science of Testimonial Sales 5534 Harry dismisses TAM sizing at the seed stage, arguing that elite founders expand markets. David agrees, sharing how Bessemer rejected Media Radar due to print magazine TAM calculations before the company pivoted online and reached multi-billion value.
Quick Fire: Private Equity, Board Members, and Sourcing Zoom 4422 In the quick-fire round, David praises Emergence partner Jake Saper for sourcing Zoom and delivering exceptional, hands-on support to portfolio companies.
Quick Fire: ZERP Era, Non-Binary Decisions, and What Matters Most 4422 Harry asks David about his most difficult unmade decisions. David explains that critical venture choices are rarely 100% binary, requiring investors to act on 51% conviction while balancing intellect and visceral emotion.

Statements from this episode (79)

Opinion
Frankel: Pro-rata rights are the original sin against entrepreneurs
“I still think of, like, pro rot as, like, the original sin against entrepreneurs.”
David Frankel Oct 14, 2024 ▶ 0:05
Opinion
Frankel: Venture capital DPI could be dead
“I think that DPI could be dead.”
David Frankel Oct 14, 2024 ▶ 24:23
Opinion
Frankel: Tiger Global operated like a casino
“Those guys were just like a casino. One call to John at Tiger. Like, 20 on 80, no problem.”
David Frankel Oct 14, 2024 ▶ 0:22
Assertion Supported
Harry Stebbings: Seed rounds are reaching $6M to $10M
“We are seeing these massive seed rounds, like six to ten million dollars.”
Harry Stebbings Oct 14, 2024 ▶ 0:51
Assertion Not publicly verifiable
Frankel: Smalls reached $50M ARR but couldn't raise capital in December
“We try to raise money for this business, Smalls, right? Doing fifty million ARR. Try to raise money in December. Nobody would look at us.”
David Frankel Oct 14, 2024 ▶ 2:54
Disclosure
Frankel: Founder Collective broke rules to invest $100K at $100M valuation
“In that situation, I broke every rule under the sun, and we put in a hundred K check, right? I broke my rules. But we don't do that.”
David Frankel Oct 14, 2024 ▶ 4:12
Insight
Frankel: VCs cannot justify board seats for $500K or smaller checks
“If I'm on your board, I can't write a hundred K check. I can't write a 500 K check anymore because you need my time and you need my interest.”
David Frankel Oct 14, 2024 ▶ 5:23
Prediction Not checkable as stated
Frankel: Founders will always prioritize brand-name VC firms like Sequoia
“I think some founders still see, you know, a name in lights, and they go, I want that name beyond anything. I, if it's Sequoia, A-sixting Z, Accel, you name it, I want that name, and I think there will always be a steady supply of founders who think that way.”
David Frankel Oct 14, 2024 ▶ 5:51
Insight
Frankel: Rejection by a Top VC Creates Severe Signaling Risks
“You know, you're in a world of hurt because someone that the world thought was, like, very, very serious and very smart about you just said no to you. Go try sell against that. I think it's very, very difficult.”
David Frankel Oct 14, 2024 ▶ 6:18
Assertion Partly supported
Frankel: 90% of VC-Backed Founders Do Not Receive Follow-On Funding
“They didn't do, but I was, they don't understand that 90% don't get follow on funding.”
David Frankel Oct 14, 2024 ▶ 6:35
Disclosure
Frankel: Founder Collective passed on Pinterest due to portfolio conflict
“The first thing that comes to mind is like Pinterest. The founders came to us and we had a conflict. We had a very strong associate in Zach Klein, who was the chairman of supply. We, we'd invested in supply. We couldn't make the investment.”
David Frankel Oct 14, 2024 ▶ 6:55
Disclosure
Frankel: I believed my early investment in Olo was a total loss
“I remember saying to my wife on Olo, this is done. We've lost a lot. This was pre-founder collective saying, we have lost our money. Like, Noah is never going to get there.”
David Frankel Oct 14, 2024 ▶ 8:04
Disclosure
Stebbings: I avoid reserves after losing money on Hopin, Clubhouse, BeReal
“I do not do reserves, and I don't because I was in Hopin, I was in Clubhouse, I was in Be Real, all lost money, and then I've got a load of companies which were much slower In enterprise and a phenomenal investments.”
Harry Stebbings Oct 14, 2024 ▶ 9:30
Disclosure
Frankel: Founder Collective kept zero reserves in its first fund
“We did no reserves in fund one, zero.”
David Frankel Oct 14, 2024 ▶ 10:00
Disclosure
Frankel: Founder Collective funded The Trade Desk when nobody else would
“Eric invests in Trade Desk as a follow on because nobody else was going to give them money.”
David Frankel Oct 14, 2024 ▶ 10:45
Disclosure
Frankel: Founder Collective maintains 1-to-1 reserve ratio but struggles to deploy it
“We still have this kind of one-to-one reserve policy, but we actually struggle on our reserves, because a lot of the time, our good companies get bit up fast.”
David Frankel Oct 14, 2024 ▶ 11:50
Disclosure
Frankel: Running Tide shut down with $10M left, burning $3M monthly
“Running Tide, we just closed down the business. This was a carbon sequestration business, ag, literally ag in the ocean. Unbelievable business. We've got ten million dollars, and he's burning three million dollars a month.”
David Frankel Oct 14, 2024 ▶ 13:48
Insight
Frankel: Founders Fail to Cut Burn Due to Loyalty and Overconfidence
“But these founders get onto this treadmill, and it's just, it's almost impossible to slow this thing down. I think what they feel like is their, and their loyalty is to the team that they've put in place, their loyalty is to the last set of capital that still …”
David Frankel Oct 14, 2024 ▶ 14:31
Insight
Frankel: Backing successful second-time founders hasn't worked out due to hubris
“I would say generally founders who've had enormous, enormous success and exits come to the next opportunity with some degree of hubris. I speak about this personally. I sold my first business And I thought I could conquer anything. And they look at any vertica…”
David Frankel Oct 14, 2024 ▶ 15:22
Insight
Frankel: Failed repeat founders who retain their team make exceptional investments
“Entrepreneurs who tried their asses off, raised money, and for some reason or another, it didn't work out. They come back hungrier. They come back, they want that prize. They want to prove. Chip on the shoulder. And if they can bring back the team somehow, so …”
David Frankel Oct 14, 2024 ▶ 15:46
Opinion
Stebbings: "What themes do you like?" is the worst question LPs ask
“Worst question LPs ask, and I get in trouble for this, is, What themes do you like?”
Harry Stebbings Oct 14, 2024 ▶ 17:27
Assertion Partly supported
Frankel: Coupang raised from BlackRock at a $4B valuation
“So I remember, I think of Coupang, and, you know, Coupang came, went to Sequoia and said, look, it's a four billion pre BlackRock will put in a billion, right?”
David Frankel Oct 14, 2024 ▶ 19:25
Insight
Frankel: Founders shopping early term sheets reveal transactional character early
“I think it's a good signal to investors early if that happens. Like, do you want to be in business with that entrepreneur? So, I'd rather it happens early to me. It happens to everyone. But I'd rather it happens early to me than later on, because it was pretty…”
David Frankel Oct 14, 2024 ▶ 20:36
Assertion Not publicly verifiable
Frankel: First Round Capital offered uncapped checks to top portfolio companies
“Josh Koppenman, I remember him saying to me, I'll give you two million dollars uncapped note ahead of the next round. A lot of this was in his portfolio already, where he went, like, what's the quadrant that's really killing it? What first round used to do is,…”
David Frankel Oct 14, 2024 ▶ 20:54
Opinion
Frankel: Liquidation preferences are a fundamental and fair venture capital mechanism
“Well, I would disagree with Nick, because I would say, prefs are fundamental. Saying, you should give your investor your, their money back, right, before you kind of, you know distribute the spoils to everybody. I think that's a fair tenet.”
David Frankel Oct 14, 2024 ▶ 21:48
Prediction Didn’t hold up
Frankel: Pari passu terms are ending as strict preference stacks return
“And the PREF stack, like peri-passu, feels like something of the past. There's a real PREF stack coming.”
David Frankel Oct 14, 2024 ▶ 23:05
Assertion Supported
Frankel: Public SaaS multiples dropped from 20x in 2021 to 5-6x
“So if you look at SAS multiples in 21, 20, Where that was 20 X, and then you look at those SAS multiples as five, six X, that trickles down.”
David Frankel Oct 14, 2024 ▶ 23:31
Disclosure
Frankel: Founder Collective's 2018 Fund III has generated zero DPI
“Fund, our Fund Three is a 20 18 vintage. No DPI yet.”
David Frankel Oct 14, 2024 ▶ 24:37
Disclosure
Frankel: Founder Collective holds PE acquisition LOI for vertical SaaS portfolio company
“We've got an LOI in a vertical SaaS business right now. LOI. We haven't got, this is not there yet. The company's done tens of millions. It's got a good valuation. It's PE.”
David Frankel Oct 14, 2024 ▶ 26:09
Prediction Not checkable as stated
Frankel: Strong post-election IPOs will trigger a broader public market reopening
“I think pre-election in the US, IPOs are pretty much closed for now. I think post-election, one or two or three great IPOs, every single, you're going to have like this swarm of JP Morgan and Goldman Sachs bankers coming to tell you, like, it is open.”
David Frankel Oct 14, 2024 ▶ 27:25
Assertion Not checkable as stated
Frankel: SeatGeek has been IPO-ready for two years
“SeatGeek's been IPO ready for two years.”
David Frankel Oct 14, 2024 ▶ 27:48
Insight
Frankel: Seed funds can return capital via multiple moderate exits, not just mega-unicorns
“Fund returners, you need four or five good fund, good companies. If we sell four companies at two hundred fifty million dollars each, right, we can return a fund. If we sell 10 companies at a hundred million each, like, nobody cares about that, we can return a…”
David Frankel Oct 14, 2024 ▶ 29:18
Disclosure
Frankel: Trade Desk was a bigger outcome for Founder Collective than Uber
“Trade Desk was a bigger outcome for us. Coupang returned the fund, right? Like if, and multiple times.”
David Frankel Oct 14, 2024 ▶ 30:10
Disclosure
Frankel: PillPack single-handedly returned Founder Collective's second fund
“PillPack returned fund two.”
David Frankel Oct 14, 2024 ▶ 30:23
Opinion
Frankel: Large VC checks without board seats signal low commitment
“And if entrepreneurs get a ten million dollar, you know, check from XYZ, you know, large scale fund, And a partner doesn't join the board. That is not a good signal.”
David Frankel Oct 14, 2024 ▶ 31:10
Disclosure
Stebbings: 20VC wrote a Series A check equal to 7.5% of fund
“We just won a series A, and I said, you should take our check. Because this is seven and a half percent of our fund. Like, you really matter to me.”
Harry Stebbings Oct 14, 2024 ▶ 32:10
Insight
Frankel: Check-to-fund size ratio reveals true investor alignment
“I think for entrepreneurs and for LPs, right, size of fund, check in company versus size of fund tells you everything. Everything.”
David Frankel Oct 14, 2024 ▶ 32:18
Disclosure
Frankel: Founder Collective has completed fewer than ten secondary deals ever
“Like if I think of the secondary we've had over our entire kind of, you know over a career, I can count it maybe on two hands.”
David Frankel Oct 14, 2024 ▶ 35:00
Assertion Not checkable as stated
Frankel: Secondary share liquidity is almost impossible for smaller private startups
“Like in your high flyers, so in your really well-known companies, there's a real secondary market. Try to get secondary in your smaller private company. It's almost impossible. So I found secondary to be very, very difficult. Where we've done secondary, they'v…”
David Frankel Oct 14, 2024 ▶ 35:16
Opinion
Frankel: VCs are quiet quitting on struggling portfolio companies
“I do. I do. You know, I think it's for the entrepreneur, It's like, there comes a point where it's like, you can have, it goes back to your earlier question, you can have words, you can have as many discussions. If the business is just not working out, like, d…”
David Frankel Oct 14, 2024 ▶ 36:48
Disclosure
Frankel: Founder Collective liquidates smaller IPO stakes for cash but distributes stock for large positions
“The answer there typically has been with big distributions, with large positions, so fund movers, or it's half the fund, we distribute, and we say it's up to you. With smaller positions, when at IPOs, so desktop metal, for instance, it got to the point where i…”
David Frankel Oct 14, 2024 ▶ 38:55
Insight
Frankel: Investors should never sell shares in companies with real moats
“If I look back, I go, like, never sell a single thing. If you could, and, you know, people have to live and People have various desires, but if you could, never sell a share. And I know we've gone through the up and the down cycle, but great companies, compani…”
David Frankel Oct 14, 2024 ▶ 39:30
Opinion
Frankel: Sequoia's evergreen fund strategy was sound despite poor timing
“Well, I think the timing was problematic, right? Clearly. But I think the theory that they had, I'm impressed with them that they thought about that, and they executed on it. I think the timing was unfortunate.”
David Frankel Oct 14, 2024 ▶ 39:59
Opinion
Frankel: Pharmacy benefit managers hold huge market caps while adding no value
“And these are these legacy companies, a great example of them is the PBMs, the Pharmacy Benefit Managers. Companies that were very innovative 40 years ago, So a PBM connects the pharmacy to the insurer. You know, 40 years ago or 30 years ago, they were great c…”
David Frankel Oct 14, 2024 ▶ 40:45
Disclosure
Frankel: I testified to the DOJ regarding Live Nation and Ticketmaster
“I actually gave I gave testimony to a panel of lawyers for the Department of Justice.”
David Frankel Oct 14, 2024 ▶ 42:02
Opinion
Frankel: Live Nation and Ticketmaster merger should never have been allowed
“So Live Nation Ticketmaster, that merger should never have been allowed. But once it's allowed, we will occupy, monopolize that position all day long.”
David Frankel Oct 14, 2024 ▶ 42:59
Assertion Partly supported
Frankel: Suno's legal battles target training inputs while OpenAI's focus on outputs
“So the OpenAI challenge is on the output, right, the LLM. Suno, the challenge is on the input, and Suno's going back and saying, we're training on the open internet.”
David Frankel Oct 14, 2024 ▶ 44:09
Insight
Frankel: AI Startups Can Reach Early Product-Market Fit Capital Efficiently
“And even in AI, Like, the teams have to get some kind of product market fit, some before, I think that can still be done reasonably capital efficiently.”
David Frankel Oct 14, 2024 ▶ 48:13
Prediction Held up
Frankel: Thrive Capital LPs will make a 2x return on OpenAI
“Is Josh in the winner there going to make two X, and maybe much more than that, but bet against the two X? I wouldn't bet against the two X. I think his LPs will make two X on that.”
David Frankel Oct 14, 2024 ▶ 48:44
Prediction Not checkable as stated
Frankel: Founder Collective passes on AI seed rounds at $100M valuations
“When I see those rounds at like 25 on a hundred, pretty much we're out. We're pretty much out. Again, team versus theme. So, you know, there are rare instances where we see someone who's just like, you cannot ignore, you wake up in the morning, you go, oh my g…”
David Frankel Oct 14, 2024 ▶ 49:47
Insight
Frankel: Seed funds cannot rely on chasing high-valuation outliers as a strategy
“Rearview mirror on this, you can't build a fund on this. Rearview mirror, you can think about that one that you missed, and they're one or two in a generation. There are these generational companies, or maybe there is one a year, and if you're in that company,…”
David Frankel Oct 14, 2024 ▶ 50:47
Prediction Not checkable as stated
Frankel: Short-Term AI Earnings Will Disappoint Relative to Massive Capex
“So I think in short term, we're going to be, you know, underwhelmed right now. I think if you look at like the amount of capex that's being spent, and you look at the actual earnings that will be generated in the short term, there's just no way it makes sense.”
David Frankel Oct 14, 2024 ▶ 53:23
Disclosure
Frankel: Founder Collective Only Invests When Seeing 10x Potential
“We look at a company and go, can we 10 X that? Can we 10 X? And if we can't, then we shouldn't invest.”
David Frankel Oct 14, 2024 ▶ 56:01
Opinion
Frankel: Aiming Exclusively for 'Unicorn or Bust' Seed Returns Is Insane
“I think it's insanity. I just think it's insanity. Like, I think when, I think you market those winners, and again, it's great PR fodder, it's great to, like, attract the investors in the next fund, but I think it's insanity to go, it's like that huge, you kno…”
David Frankel Oct 14, 2024 ▶ 57:09
Insight
Frankel: Venture funds aren't taking enough risk if they aren't losing money
“But I think it's the most unfair feature of capitalism, Harry, is the most you can lose is all your money. The most you can make is three, you know, 3000 X, right, or unlimited. If you just look at that, it is such an unfair feature of capitalism, and my LPs m…”
David Frankel Oct 14, 2024 ▶ 57:59
Insight
Frankel: Backing product ideas without founder chemistry is a major VC mistake
“When I look at it and I go, I fell in love with a what? Like, I fell in love with a what, but I really didn't love the entrepreneur at the beginning, and I wasn't, you know, the chemistry wasn't there, that's a mistake.”
David Frankel Oct 14, 2024 ▶ 59:31
Assertion Not checkable as stated
Frankel: Competitive market heat does not correlate with deal quality
“No, not at all.”
David Frankel Oct 14, 2024 ▶ 1:01:13
Insight
Frankel: High market heat is the ideal moment to take secondary liquidity
“In fact, in an ideal situation when there's insane heat in something that we've gotten earlier, like that's a great moment to take secondary if you can.”
David Frankel Oct 14, 2024 ▶ 1:01:20
Disclosure
Frankel: Founder Collective regrets selling any secondary shares in Trade Desk and Uber
“Well, Trade Desk, I regret every single share I sold. Uber, I regret every single share I sold.”
David Frankel Oct 14, 2024 ▶ 1:02:13
Insight
Frankel: Founders selling under 10% secondary equity face minimal investor backlash
“If you take, you know, less, 10% or less off the table, Nobody's gonna really mind too much.”
David Frankel Oct 14, 2024 ▶ 1:02:52
Insight
Frankel: A founder's first $1M in secondary liquidity is life-altering
“By the way, I always say the first million dollars, like when the first million dollars makes, like, it's binary. It makes all the difference.”
David Frankel Oct 14, 2024 ▶ 1:03:10
Opinion
Stebbings: Growth investors are hypocritical for criticizing founder secondaries
“I am pissed off, and I'm pissed off with growth investors who were shoveling cash down founders throats in the good times, and are now going, I can't believe all these founders that took all that money off the table.”
Harry Stebbings Oct 14, 2024 ▶ 1:03:52
Opinion
Frankel: Excessive capital deployment was venture capital's biggest recent sin
“The biggest sin of the last era has been Just the huge amounts of capital.”
David Frankel Oct 14, 2024 ▶ 1:04:09
Opinion
Frankel: Writing off Salesforce in AI ignores their massive proprietary data advantage
“So Mark Benioff, Salesforce, you write that off at your peril, because the amount of data they have, right, they throw in these AI tools, they're doing their own stuff, right? That is, that, like, their opportunity is enormous”
David Frankel Oct 14, 2024 ▶ 1:06:43
Prediction Not checkable as stated
Frankel: LLM tools will commoditize, letting SaaS companies buy AI infrastructure cheaply
“I think the tools, I actually think some of the LLM and the, you know, I think some of the tools are actually very commoditized. So I think that the vertical SaaS or horizontal SaaS or data owners We'll be able to access the underlying tools reasonably cheaply…”
David Frankel Oct 14, 2024 ▶ 1:08:39
Opinion
Stebbings: Enterprise clients lack the technical sophistication to build in-house AI solutions
“I think we drastically overestimate the technology sophistication of these companies. To be able to build with AI their own vertical solutions. Are you kidding me? They struggle to onboard Slack.”
Harry Stebbings Oct 14, 2024 ▶ 1:09:13
Insight
Frankel: Taking a VC board seat with under 15% ownership is problematic
“If you kick off and you own on a board, like, less than 15% of that company, I think it's problematic.”
David Frankel Oct 14, 2024 ▶ 1:10:59
Disclosure
Frankel: Founder Collective does not worry about dilution
“We don't think about dilution much. We really don't. Our MO has been, we dilute alongside the founder. As a seed stage fund, we get involved at the beginning, and it's been a strategy, and we don't think about dilution.”
David Frankel Oct 14, 2024 ▶ 1:11:58
Insight
Frankel: Seed funds cannot afford maintaining ownership in successful markups
“I, by the way, I can't afford in my fund, if I've done my job right, and you are, you know, raising your next set of capital at three X or four X, I just can't afford to actually maintain my percentage ownership.”
David Frankel Oct 14, 2024 ▶ 1:12:26
Assertion Contradicted
Frankel: I've had only one bankruptcy across hundreds of investments
“You know, I, I've, in a career, I've been through one bankruptcy. Like, one bankruptcy. So in a career, in hundreds of investments, I've had one bankruptcy.”
David Frankel Oct 14, 2024 ▶ 1:14:28
Disclosure
Frankel: I returned millions in secondary payouts after discovering startup fraud
“I'd been paid out a couple of million dollars. The first thing Lou said to me is, you're gonna give back every last cent. You're gonna be the first person who gives back all the money, and in the end, and all the other investors are gonna hate you for it, but …”
David Frankel Oct 14, 2024 ▶ 1:15:20
Prediction Not checkable as stated
Frankel: More ZIRP-era startup portfolio frauds will come to light
“I think they could come out. I think the era gave, you know, gave, I think, Harry, I think the era gave rise to that, unfortunately.”
David Frankel Oct 14, 2024 ▶ 1:16:20
Opinion
Frankel: Multi-stage VC firms have no incentive to matchmake for startups
“Sequoia will, it doesn't matter, by the way, I don't want to single out Sequoia here, but it doesn't matter if you take your check from Andreessen, Sequoia, Axel, you name them, right? They will never, they have no incentive to matchmake. They have no incentiv…”
David Frankel Oct 14, 2024 ▶ 1:17:17
Disclosure
Frankel: Founder Collective built dedicated systems and staff for partner matchmaking
“So, Harry, I promise you, I imagine a lot of your time is like, oh, think about that fund, think about that partner, to the point that over 15 years we've operationalized this. Like our software, I don't care if you use Monday, Airtable, we use Airtable. But o…”
David Frankel Oct 14, 2024 ▶ 1:18:09
Insight
Stebbings: VCs often force sub-optimal angels onto founders to repay favors
“Especially on structuring rounds, people will bring in people who are maybe not the best fit for the company, But they owe them for a deal that was done before, or they want to curry favors with people. I see this a lot where I'm like, hey, hey, the head of gr…”
Harry Stebbings Oct 14, 2024 ▶ 1:19:35
Assertion Partly supported
Frankel: Olo raised $600M at 10% dilution in its IPO
“Noah raised six hundred million for 10% dilution when he IPO'd, right?”
David Frankel Oct 14, 2024 ▶ 1:22:39
Opinion
Frankel: Private equity firms can add significant value to VC portfolio companies
“I used to think that PE firms were like the enemy of the seed stage, and I've changed my mind on that. We've got some PE firms in two vertical SaaS companies that I'm involved in, and their rigor, their financial discipline, and the help they've given to those…”
David Frankel Oct 14, 2024 ▶ 1:23:04
Insight
Frankel: Major decisions are made on 51% conviction, not certainty
“The, every great decision was never binary. It was always weighing up scales, and I think getting to conviction is confusing for people because they listen to this and they go, oh, you were binary about that. Like, you knew unequivocally, and the truth was, li…”
David Frankel Oct 14, 2024 ▶ 1:26:37
Disclosure
Frankel: I must strong-arm my partners to write $5M seed checks
“I have to, like, strong arm my partners into, like, putting five million dollars into a company.”
David Frankel Oct 14, 2024 ▶ 1:30:29

Shorts cut from this episode

▶ Is capitalism broken? 💸 · 20VC with Harry Stebbings (@58:03) ▶ How to evaluate VC offers 🤔 · 20VC with Harry Stebbings (@31:14) ▶ Investing Lessons from Uber 🚖 · 20VC with Harry Stebbings (@0:16)
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