My 20 Minute VC Interview from September 2019

Harry Stebbings just released a new episode with me on the 20 Minute VC. I love how Harry uses all caps to title the episodes.

20VC: BRAD FELD ON WHY MARKET SIZE AT EARLY STAGE IS NOT HELPFUL, HIS BIGGEST LEARNINGS FROM THE BOOM & BUST OF THE DOT COM AND HOW THE BEST VCS WORK FOR THEIR CEOS

I adore Harry. I did an interview with him early on (#65) so it’s particularly fun to do an interview number that is great than this year.

We cover the following topics, among others. Plus, there is a special book giveaway and a few other gems buried in the episode.

1.) How Brad made his way into the world of venture following 40 angel checks and how that led to his co-founding Foundry Group? Why did Brad find the transition from angel to VC in the early days such a challenge? What 2 core things did he focus on when writing angel checks? How has that changed now as a VC?

2.) How did seeing the boom and bust of the dot com impact Brad’s investing mindset today? How does Brad think about investing through market cycles and the right way to think about investment cadence? Why does Brad believe that to be successful as a VC you have to be fundamentally optimistic?

3.) Where does Brad believe we are today in the cycle? Does he agree with Bill Gurley on the biggest challenge being the “oversupply of capital”? What must entrepreneurs understand with regards to market cycle dynamics and how they can and need to future-proof their business?

4.) From analysing his best investments, why has Brad come to the conclusion that TAM in the early days is really not helpful? What are the commonalities in how Brad’s most successful companies approach experimentation?

5.) What does Brad mean when he says, “don’t have fake CEO or fake VC days”? What does he mean when he often says, “run your fucking business”? What in Brad’s mind would constitute a “fake day” vs moving the needle for your business? What does Brad think is the best way for VCs to truly get to know one another? Why is, “hey let’s do a deal together one of the most hollow and fake statements in venture?”

6.) Brad has sat on some of the most meaningful boards of the last 2 decades, what have been Brad’s biggest learnings on what it takes to be a great board member? How does that change with the progression of your career? What advice would Brad give to me, having just gained my first board seat? If the VC does not support the CEO, what is the right process? Why does Brad believe the VC should work for the CEO?

7.) What is Brad’s biggest advice when it comes to learning how to say no? What advice does Brad hear most often that he commonly disagrees with? Why does Brad feel we are in a moment of peak noise in the ecosystem today? To be a great leader, what 2 skills does Brad believe you need to have?