Reboot Podcast Episode #45 – What’s Love Got to Do with It?- with Fred Wilson & Brad Feld

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 45 // August, 1 2016

“Wisdom, then, is a deeper way of knowing. Wisdom is the art of living in rhythm with your soul, your life, and the divine. Wisdom is the way that you learn to decipher the unknown; and the unknown is our closest companion. So wisdom is the art of being courageous and generous with the unknown, of being able to decipher and recognize its treasures.”


Brad Feld

Brad Feld

VC at Foundry Group and Entrepreneur

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Fred Wilson

Fred Wilson

VC at Union Square Ventures

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Episode Description

How can you expect to serve others, whether it be customers, portfolio companies, or your organization if your own house is not in order?

We are so fortunate to welcome Brad Feld and Fred Wilson back to the Reboot Podcast.  Jerry, Brad, and Fred have a friendship and history that goes back 20 years, and the wealth of experience between them is truly incredible.  In what we hope will be a series of conversations, Fred, Brad, and Jerry share stories from the past, moments where they were pushed to their limits physically and emotionally.  They talk about the critical steps they’ve taken to being an effective and supportive board member and investor, and how the lessons from past painful experiences show up in the values of their firms.  

To quote Jerry’s blog post on this episode, “What’s love go to do with it? Everything.”


Left to right: Rich Levandov, Fred, Gary Rieschel, Jerry, Brad, and Charley Lax

Brad Feld on Twitter | Fred Wilson on Twitter

Show Highlights

Top Quotes:

“What does it mean to really be a supportive investor?” – Jerry Colonna

“If you are worried about your own investment in the company, you are going to have a hard time being effective.” – Fred Wilson

“If you can think about what’s in the best interest of the people who are running the company and the company itself, that will counterintuitively lead to better outcomes of your financial investment than it would if you were just focused on your financial investment.” – Fred Wilson

“When you are in a group dynamic and you approach things selfishly, it is very hard to be effective.” – Fred Wilson

“When you are in a group dynamic and you can leave your self-interests to the side and think about what’s in the best interest of the group, you can be very effective.” – Fred Wilson

“Once I make an investment, I work for the CEO.”  – Brad Feld

“By definition, if you are working for the company and you are effective, you are working for your investment.” – Brad Feld

“Not having a sense of evolved management of your own psyche leads to a counterproductive management of the investment on the part of the investor.” – Jerry Colonna

“There are a lot of investors who walk into the room, take their seat as an investor, and they are scared shitless.” – Jerry Colonna

“We value the trust we have around the table more than anything.” – Fred Wilson

“It is really hard when you are a young investment professional coming into a dynamic where you have to prove yourself, you are being measured, and you won’t make the cut if you don’t deliver.” – Fred Wilson

“If you are going to lose the money that’s fine, but don’t fuck up the company in the process.” – Fred Wilson

“In that moment of panic, you have got to confront your own fear, your own shit, and what you are bringing into it.” – Jerry Colonna

“It was my own anxiety that I wasn’t admitting to myself. I was trying to hold it in and pretend like I had all my shit together, and then all of the sudden I felt like I couldn’t breathe.” – Fred Wilson

“Anybody who has had a panic attack knows that it is a physical out-of-body experience where you can’t even connect with what is actually happening.” – Jerry Colonna

“You hold a baby bird in your hand and the tighter you squeeze it to try to control it the more you kill it.” – Brad Feld

“There are a lot of problems that have nothing to do with you or your competence as an investor, but you still have the problem to solve.” – Brad Feld

“They can’t kill you, and they can’t eat you.” – Brad Feld

“The thing that drove us was we wanted to create a firm that we wanted to work in, and that was designed from the ground up not to have all those things that all the other places we worked at had.” – Fred Wilson

“By the third time you do something you get it right.” – Fred Wilson

“One of the deeply held beliefs we had from the beginning was that we wanted to be equal partners and we wanted to be best friends.” – Brad Feld

“Every quarter, in addition to focusing on a review of our portfolio and what was going on in our companies, we would also do a review of each other and our relationships.” – Brad Feld

“Having a safe and confidential place with the people who are my equal partners and best friends to deal openly with issues on any dimension is the bedrock of what we have created.” – Brad Feld

“The mistake a lot of people make in our world is to not go deep, and to not invest the right amount of time going deep.” – Brad Feld

“By investing the time in creating a healthy partnership, you are actually able to then put the company’s first.” – Jerry Colonna

“It is very hard for a venture capitalist or a venture capital firm to do right by a company if they don’t have their house in order.” – Fred Wilson

“Brutal honesty delivered kindly.” – Brad Feld

“We will all have crises and the crises will continue. A lot of times they are out of the blue, you can’t control them, and you don’t understand what is actually causing them, but you still have to deal with them.” – Brad Feld

“Try and be observant of the partnership dynamic while you are pitching.” – Fred Wilson

“A healthy functioning partnership helps companies and unhealthy dysfunctional partnerships generally hurt companies.” – Fred Wilson

“Healthy partnerships don’t all look the same.” – Brad Feld

“If we are going to go out on a limb and become entrepreneurs, we have the opportunity to create the kind of company that we want to work for.” – Jerry Colonna