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Aug 31, 2016 · 30m · 20vc

20VC: Why Great Founders Are Both Visionary & Stubborn, The Investment Mindset Shift From Angel To VC & How To React When The 'S*** Hits The Fan?' with Jesse Middleton, General Partner @ Flybridge Capital Partners

Jesse Middleton · 22m spoken Harry Stebbings · 6m 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, Flybridge Capital General Partner Jesse Middleton shares insights from his transition from early WeWork executive to institutional venture capitalist. He discusses evaluating founder resilience, balancing conviction with adaptability during pivots, managing operational crises, and adapting to institutional venture capital economics.

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 21.6% of the talking time here. How this is scored →

Harry as informed peer 2.4 Guest teaching 2.4 Guest disagreement 0.7 Harry pushing back 0.7
05100:0010:0020:0030:001:47–4:14 · Harry as informed peer 1/10 WeWork Founding Story and Transition to Venture Capital Harry welcomes Jesse and asks a standard opening question about WeWork's founding and his transition into venture capital. Jesse responds with an agreeable narrative overview of his career path without any tension.4:14–8:07 · Harry as informed peer 4/10 Operational Insights and Identifying Outlier Founders Harry introduces the case study of Kevin Systrom pivoting Burbn to Instagram to challenge the line between founder vision and stubbornness. Jesse provides a nuanced breakdown of how hypotheses must be paired with self-reflection.8:07–12:35 · Harry as informed peer 3/10 Transitioning from Angel Investor to VC Fiduciary Duty Harry probes how Jesse's mindset shifts when managing institutional money versus personal capital. Jesse details the mathematical imperative of fund-returning outlier investments compared to angel investing.12:35–16:17 · Harry as informed peer 3/10 Building Pattern Recognition and Adapting to VC Pace Harry jokes about Jesse acting like AI processing historical deal data, maintaining an engaged dialogue. Jesse explains the core difficulty of VC, which is the long feedback loops compared to operating a business.16:18–20:35 · Harry as informed peer 2/10 Problem-Solving Aptitude and Staying in the Weeds Harry asks whether Jesse will miss operational problem-solving. Jesse shares a personal story about childhood aptitude tests to highlight his framework for breaking complex problems into actionable parts.20:35–23:48 · Harry as informed peer 2/10 Navigating Crisis and Turning Failures into Opportunities Harry asks a personal advice question about how to handle crisis situations when websites go down. Jesse explains his mindset of searching for hidden operational opportunities during chaos, citing early WeWork facility failures.23:48–28:40 · Harry as informed peer 2/10 Quickfire Round: Books, Productivity Hacks, and Squire Harry runs through quickfire questions, bringing up a Fast Company headline comparison to Jack Dorsey. Jesse lightheartedly dismisses the premise of the headline before answering with practical productivity habits.1:47–4:14 · Guest teaching 1/10 WeWork Founding Story and Transition to Venture Capital Harry welcomes Jesse and asks a standard opening question about WeWork's founding and his transition into venture capital. Jesse responds with an agreeable narrative overview of his career path without any tension.4:14–8:07 · Guest teaching 3/10 Operational Insights and Identifying Outlier Founders Harry introduces the case study of Kevin Systrom pivoting Burbn to Instagram to challenge the line between founder vision and stubbornness. Jesse provides a nuanced breakdown of how hypotheses must be paired with self-reflection.8:07–12:35 · Guest teaching 3/10 Transitioning from Angel Investor to VC Fiduciary Duty Harry probes how Jesse's mindset shifts when managing institutional money versus personal capital. Jesse details the mathematical imperative of fund-returning outlier investments compared to angel investing.12:35–16:17 · Guest teaching 3/10 Building Pattern Recognition and Adapting to VC Pace Harry jokes about Jesse acting like AI processing historical deal data, maintaining an engaged dialogue. Jesse explains the core difficulty of VC, which is the long feedback loops compared to operating a business.16:18–20:35 · Guest teaching 2/10 Problem-Solving Aptitude and Staying in the Weeds Harry asks whether Jesse will miss operational problem-solving. Jesse shares a personal story about childhood aptitude tests to highlight his framework for breaking complex problems into actionable parts.20:35–23:48 · Guest teaching 3/10 Navigating Crisis and Turning Failures into Opportunities Harry asks a personal advice question about how to handle crisis situations when websites go down. Jesse explains his mindset of searching for hidden operational opportunities during chaos, citing early WeWork facility failures.23:48–28:40 · Guest teaching 2/10 Quickfire Round: Books, Productivity Hacks, and Squire Harry runs through quickfire questions, bringing up a Fast Company headline comparison to Jack Dorsey. Jesse lightheartedly dismisses the premise of the headline before answering with practical productivity habits.1:47–4:14 · Guest disagreement 0/10 WeWork Founding Story and Transition to Venture Capital Harry welcomes Jesse and asks a standard opening question about WeWork's founding and his transition into venture capital. Jesse responds with an agreeable narrative overview of his career path without any tension.4:14–8:07 · Guest disagreement 1/10 Operational Insights and Identifying Outlier Founders Harry introduces the case study of Kevin Systrom pivoting Burbn to Instagram to challenge the line between founder vision and stubbornness. Jesse provides a nuanced breakdown of how hypotheses must be paired with self-reflection.8:07–12:35 · Guest disagreement 1/10 Transitioning from Angel Investor to VC Fiduciary Duty Harry probes how Jesse's mindset shifts when managing institutional money versus personal capital. Jesse details the mathematical imperative of fund-returning outlier investments compared to angel investing.12:35–16:17 · Guest disagreement 1/10 Building Pattern Recognition and Adapting to VC Pace Harry jokes about Jesse acting like AI processing historical deal data, maintaining an engaged dialogue. Jesse explains the core difficulty of VC, which is the long feedback loops compared to operating a business.16:18–20:35 · Guest disagreement 0/10 Problem-Solving Aptitude and Staying in the Weeds Harry asks whether Jesse will miss operational problem-solving. Jesse shares a personal story about childhood aptitude tests to highlight his framework for breaking complex problems into actionable parts.20:35–23:48 · Guest disagreement 1/10 Navigating Crisis and Turning Failures into Opportunities Harry asks a personal advice question about how to handle crisis situations when websites go down. Jesse explains his mindset of searching for hidden operational opportunities during chaos, citing early WeWork facility failures.23:48–28:40 · Guest disagreement 1/10 Quickfire Round: Books, Productivity Hacks, and Squire Harry runs through quickfire questions, bringing up a Fast Company headline comparison to Jack Dorsey. Jesse lightheartedly dismisses the premise of the headline before answering with practical productivity habits.1:47–4:14 · Harry pushing back 0/10 WeWork Founding Story and Transition to Venture Capital Harry welcomes Jesse and asks a standard opening question about WeWork's founding and his transition into venture capital. Jesse responds with an agreeable narrative overview of his career path without any tension.4:14–8:07 · Harry pushing back 2/10 Operational Insights and Identifying Outlier Founders Harry introduces the case study of Kevin Systrom pivoting Burbn to Instagram to challenge the line between founder vision and stubbornness. Jesse provides a nuanced breakdown of how hypotheses must be paired with self-reflection.8:07–12:35 · Harry pushing back 1/10 Transitioning from Angel Investor to VC Fiduciary Duty Harry probes how Jesse's mindset shifts when managing institutional money versus personal capital. Jesse details the mathematical imperative of fund-returning outlier investments compared to angel investing.12:35–16:17 · Harry pushing back 1/10 Building Pattern Recognition and Adapting to VC Pace Harry jokes about Jesse acting like AI processing historical deal data, maintaining an engaged dialogue. Jesse explains the core difficulty of VC, which is the long feedback loops compared to operating a business.16:18–20:35 · Harry pushing back 0/10 Problem-Solving Aptitude and Staying in the Weeds Harry asks whether Jesse will miss operational problem-solving. Jesse shares a personal story about childhood aptitude tests to highlight his framework for breaking complex problems into actionable parts.20:35–23:48 · Harry pushing back 0/10 Navigating Crisis and Turning Failures into Opportunities Harry asks a personal advice question about how to handle crisis situations when websites go down. Jesse explains his mindset of searching for hidden operational opportunities during chaos, citing early WeWork facility failures.23:48–28:40 · Harry pushing back 1/10 Quickfire Round: Books, Productivity Hacks, and Squire Harry runs through quickfire questions, bringing up a Fast Company headline comparison to Jack Dorsey. Jesse lightheartedly dismisses the premise of the headline before answering with practical productivity habits.

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

0:00 · Harry 63.5% · guest 36.5%0:00 · Harry 63.5% · guest 36.5%3:00 · Harry 7.3% · guest 92.7%3:00 · Harry 7.3% · guest 92.7%6:00 · Harry 24.4% · guest 75.6%6:00 · Harry 24.4% · guest 75.6%9:00 · Harry 8.8% · guest 91.2%9:00 · Harry 8.8% · guest 91.2%12:00 · Harry 18% · guest 82%12:00 · Harry 18% · guest 82%15:00 · Harry 11.5% · guest 88.5%15:00 · Harry 11.5% · guest 88.5%18:00 · Harry 17.3% · guest 82.7%18:00 · Harry 17.3% · guest 82.7%21:00 · Harry 5.5% · guest 94.5%21:00 · Harry 5.5% · guest 94.5%24:00 · Harry 10.6% · guest 89.4%24:00 · Harry 10.6% · guest 89.4%27:00 · Harry 50% · guest 50%27:00 · Harry 50% · guest 50%
Sharpest disagreement ▶ 24:26 Jesse rejects Fast Company headline premise

Jesse politely pushes back against Harry's citation of a Fast Company article, clarifying that the claim comparing his work ethic to Jack Dorsey definitely was not true.

 Hardest push from Harry ▶ 6:04 Harry challenges founder vision vs stubbornness

Harry brings up Kevin Systrom's pivot from Burbn to Instagram to challenge the idea of stubborn conviction, forcing Jesse to define where vision ends and stubbornness begins.

 Biggest teaching moment ▶ 10:18 Jesse details VC fund economics vs angel investing

Jesse breaks down the fiduciary realities of VC investing, explaining how seed dilution and fund payback requirements mandate searching for massive outliers compared to personal angel checks.

 Harry holds his own ▶ 6:04 Harry offers historical pivot counterexample

Harry demonstrates strong industry knowledge by introducing the specific historical example of Instagram's pivot to test Jesse's thesis on great founders.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
WeWork Founding Story and Transition to Venture Capital 1100 Harry welcomes Jesse and asks a standard opening question about WeWork's founding and his transition into venture capital. Jesse responds with an agreeable narrative overview of his career path without any tension.
Operational Insights and Identifying Outlier Founders 4312 Harry introduces the case study of Kevin Systrom pivoting Burbn to Instagram to challenge the line between founder vision and stubbornness. Jesse provides a nuanced breakdown of how hypotheses must be paired with self-reflection.
Transitioning from Angel Investor to VC Fiduciary Duty 3311 Harry probes how Jesse's mindset shifts when managing institutional money versus personal capital. Jesse details the mathematical imperative of fund-returning outlier investments compared to angel investing.
Building Pattern Recognition and Adapting to VC Pace 3311 Harry jokes about Jesse acting like AI processing historical deal data, maintaining an engaged dialogue. Jesse explains the core difficulty of VC, which is the long feedback loops compared to operating a business.
Problem-Solving Aptitude and Staying in the Weeds 2200 Harry asks whether Jesse will miss operational problem-solving. Jesse shares a personal story about childhood aptitude tests to highlight his framework for breaking complex problems into actionable parts.
Navigating Crisis and Turning Failures into Opportunities 2310 Harry asks a personal advice question about how to handle crisis situations when websites go down. Jesse explains his mindset of searching for hidden operational opportunities during chaos, citing early WeWork facility failures.
Quickfire Round: Books, Productivity Hacks, and Squire 2211 Harry runs through quickfire questions, bringing up a Fast Company headline comparison to Jack Dorsey. Jesse lightheartedly dismisses the premise of the headline before answering with practical productivity habits.

Statements from this episode (6)

Assertion Not checkable as stated
WeWork was conceived as a global entrepreneur network from its inception
“Adam Miguel's vision was always to build a company that was going to be this global professional network of entrepreneurs and small business owners”
Jesse Middleton Aug 31, 2016 ▶ 2:34
Assertion Not checkable as stated
Flybridge invested in roughly 80 of 19,000 evaluated companies over 15 years
“There's also, we actually have a lot of data. Flybridge has been around for 15 years. In, in our deal flow product, we have We've documented over 19,000 companies that we've looked at. That's an incredible number. I mean, I wouldn't have guessed that if you wo…”
Jesse Middleton Aug 31, 2016 ▶ 13:19
Insight
Evaluating venture capital investor performance takes five to ten years
“Knowing if you're any good at venture takes, you know, five years, seven years, sometimes 10 years, so I can't really speak for if I'm”
Jesse Middleton Aug 31, 2016 ▶ 14:48
Assertion Not checkable as stated
WeWork's second location opened with unfinished construction for 220 members
“In that moment, a story that I can't think about is, is the way that our members handled when we moved to our second We work labs location, which was on Varick street. And we walked into the building on opening day and construction wasn't done. We had 220 peop…”
Jesse Middleton Aug 31, 2016 ▶ 21:55
Assertion Not checkable as stated
WeWork tests and iterates on physical spaces directly with live members
“And we learned that people were more resilient than we thought, which actually led us down the path of now we're able to test and iterate on physical spaces inside of WeWork with real members sometimes because we know they're willing to sort of participate in …”
Jesse Middleton Aug 31, 2016 ▶ 22:40
Assertion Not checkable as stated
YC startup Squire grew revenue 40x within months of Middleton's investment
“One of my more recent investments And so it's a company called Squire, who is currently in Y Combinator about the demo in a couple of weeks. And these are just two incredible founders, Dave and Song, who have started from zero startup experience to now having …”
Jesse Middleton Aug 31, 2016 ▶ 27:40
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