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

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 is a General Partner @ Flybridge Capital Partners. Prior to joining Flybridge, Jesse was an early executive at WeWork, one of the fastest growing and most valuable startups in history. He co-founded WeWork Labs in 2011, and ran WeWork X, M&A, startup investments, business and digital product development as well as inside sales during his five-year tenure at the company. Prior to WeWork, Jesse was the co-founder and CEO of Backstory, a venture backed startup. Jesse also has experience as a prolific angel investor having invested in the like of Fitmob (acq by ClassPass) YourTrove acq by LiveNation and inDinero, who you might remember we had Jessica Mah, Founder @ inDinero on the show.

In Today's Episode You Will Learn:

1.) How Jesse made the transition from operator with WeWork to General Partner @ Flybridge?

2.) At what stage does founder vision transition to become stubbornness? How does Jesse approach the situation of telling a founder when it is not working?

3.) How does Jesse's investment mindset shift from making the move from angel to VC with fiduciary responsibility?

4.) How does Jesse look to develop pattern recognition as a new entrant to VC? How important a role does mentorship play for Jesse?

5.) What are the characteristics Jesse looks for in a founder that suggest an innate problem solver? How does Jesse deal with problems when the 'shit hits the fan?'

Items Mentioned In Today's Show:

Jesse's Fave Blog and Newsletter: Purple, The Skimm

Jesse's Fave Book: Leadership & The Challenge of Self Deception

Jesse's Most Recent Investment: Squire

As always you can follow Harry, The Twenty Minute VC and Jesse on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer

20Product: Why You Should Not Go Into Product Management, Why the CEO is Always the CPO, How to Build the Best Product Teams & Why You Should Hire People Who Aren't In Product Already with Databricks SVP Product, David Meyer

David Meyer is the SVP Products at Databricks where he drives product strategy and execution. He previously ran Engineering and Product Management at OneLogin, where he grew the company to thousands o...

1 Marras 20231h 2min

20VC: Should Large Crypto Funds Give Money Back to LPs | What Will the Next Generation of Crypto Funds Look Like | What Should Happen with FTX; Who Should be Held to Account | The Future of NFTs & What Happens to Opensea w/ Nick Tomaino @ 1confirmation

20VC: Should Large Crypto Funds Give Money Back to LPs | What Will the Next Generation of Crypto Funds Look Like | What Should Happen with FTX; Who Should be Held to Account | The Future of NFTs & What Happens to Opensea w/ Nick Tomaino @ 1confirmation

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M in backing from individua...

30 Loka 202355min

20VC: The Three Types of Seed Round Today, Why Seed Has Never Been More Competitive, Why Pricing Has Never Been Higher, Why Boards at Pre-Seed Can Be Helpful & How Too Much Cash Too Soon Can Harm Companies with Ed Sim, Founder @ Boldstart

20VC: The Three Types of Seed Round Today, Why Seed Has Never Been More Competitive, Why Pricing Has Never Been Higher, Why Boards at Pre-Seed Can Be Helpful & How Too Much Cash Too Soon Can Harm Companies with Ed Sim, Founder @ Boldstart

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the las...

27 Loka 202347min

20Growth: Should Startups Hire Advisors? When is the Right Time? How Much Should They Be Paid? How Should Founders Approach the Hiring Process for Advisors? What Should They Expect From Them? What are the Biggest Mistakes Made and more with Ely Lerner

20Growth: Should Startups Hire Advisors? When is the Right Time? How Much Should They Be Paid? How Should Founders Approach the Hiring Process for Advisors? What Should They Expect From Them? What are the Biggest Mistakes Made and more with Ely Lerner

Ely Lerner is an EIR at Reforge and an advisor for startups transitioning from traction to hypergrowth. Previously he was Head of Consumer Product at Chime, and before that spent an incredible 8 years...

25 Loka 202351min

20VC: Scaling to $50M ARR in 3 Years, Scaling to $20M ARR with Just $2M Invested; The Story of PhotoRoom, Is This YC's Most Capital Efficient Company with Matthieu Rouif, Co-Founder & CEO @ PhotoRoom

20VC: Scaling to $50M ARR in 3 Years, Scaling to $20M ARR with Just $2M Invested; The Story of PhotoRoom, Is This YC's Most Capital Efficient Company with Matthieu Rouif, Co-Founder & CEO @ PhotoRoom

Matthieu Rouif is the Co-Founder and CEO @ PhotoRoom, one of the fastest-growing YC companies having scaled to an astonishing $50M in ARR in just 3 years. Their capital efficiency is immense having sc...

23 Loka 202343min

20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open

20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open

Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has f...

20 Loka 202327min

20VC: Are LPs Open For Business? What Does it Take to Raise a Fund Today? How Has What LPs Want to See in Fund Investments Changed? Why Do LP Incentive Mechanisms Need to Change? Which Funds Will be Hit Hardest with Beezer Clarkson @ Sapphire Partners

20VC: Are LPs Open For Business? What Does it Take to Raise a Fund Today? How Has What LPs Want to See in Fund Investments Changed? Why Do LP Incentive Mechanisms Need to Change? Which Funds Will be Hit Hardest with Beezer Clarkson @ Sapphire Partners

Beezer Clarkson leads Sapphire Partners' investments in venture funds domestically and internationally. Beezer has invested in some of the best firms of a generation including USV and Point Nine to na...

18 Loka 202349min

20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare

20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare

Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 empl...

16 Loka 202354min

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