Reboot Podcast Episode #119 – Investing in Trust – with Fred Wilson (re-release)

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Episode 119 // February 14, 2020


Fred Wilson

Fred Wilson

Managing Partner at Union Square Ventures

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Episode Description

In 19 years of friendship and partnership in the startup world, Jerry and Fred Wilson have seen just about everything.  In this conversation, they share some stories from the Flatiron Partnership days, what makes a perfect board, the importance of trust in investing, and what makes a good leader. They even discuss the sheer terror they felt on their own entrepreneurial journey.

Fred Wilson on Twitter | The Perfect Board | Reboot Your Board |

Other Reboot Podcast Episodes that feature Fred: #70 – The Inner-Workings of a Good Board – with Brad Feld & Fred Wilson | Extras #4: 360 Reviews with Fred Wilson | #45 – What’s Love Got to Do with It?- with Fred Wilson & Brad Feld |

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Show Highlights

Top Quotes:

“People don’t think of VCs as entrepreneurs.” – Jerry Colonna

“We stuck with the founders as the leaders of the company for too long, when it was abundantly clear that they were incapable of managing the business at the scale that they were operating.” – Fred Wilson

“We did not live up to our duty and obligation as a board. We knew that the founders were in over their heads and we knew that they weren’t really running the company properly. We should have stepped in and done something about it and we didn’t do it until it was too late.” – Fred Wilson

“When you know that you’re doing the right thing and that there are lots of people who are depending on you to do the right thing then it makes it easier to have that conversation.” – Fred Wilson

“As an investor in a company you must establish trust with the entrepreneur and the only way to do that is with your actions.” -Fred Wilson

“The moral obligation isn’t just to the company per se, or to the stakeholders, but it’s to the community, to the ecosystem of human beings that are surrounding that.” – Jerry Colonna

“I think that the internal hire if you can do it, is the better move because there’s already an understanding of that person that they’ve already demonstrated their leadership skills.” – Fred Wilson

“There is no perfect CEO. Everybody is going to have certain strengths and certain weaknesses. And what the board does to understand that openly and do something about it is very important.” – Fred Wilson

“There is no formula for leadership. Different companies require different kinds of leaders and different stages require different kinds of leaders.” – Fred Wilson

“When you show up on a board of a company, there’s no chance that you know as much about the company as the person who is running it – who has founded it.” – Fred Wilson

“You have to earn the trust of the entrepreneur and you earn the trust of the entrepreneur with actions.” – Fred Wilson

“If there’s any single lesson, whether it’s you – as a board member or as a mentor or even as a coach or as a CEO,  you’ve got to take your seat. It’s your life. It’s your job to do that.” – Jerry Colonna