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Wonder Women Entrepreneurs! This is the place to join conversations with thought leaders who amaze, astonish and inspire you. Listen each week as entrepreneur and host Kalika Yap explores the challenges, wisdom and breakthroughs of extraordinary people. (An Entrepreneurs’ Organization production)

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Feb 9, 2018

Brad Feld, early stage investor and entrepreneur, co-founded Foundry group, Techstars, Mobius Venture Capital, and Intensity Ventures. Today on the Wonder podcast, Brad discusses how to execute your business better, how to properly raise money, and why radical self-inquiry is critical if you truly want to be successful. Tune-in to learn how Brad’s businesses are supporting women in IT, why hiring a “culture fit” is actually a bad idea, and how he is breaking the stigma around mental health issues.


Time Stamped Show Notes:


  • 00:52 – In his book “Startup Opportunities” he discusses the difference between a startup and a small business; what’s the difference?
  • 01:07 – The definition of entrepreneurship in government and the discussion of “mainstream business” and “startups”
  • 01:50 – 2 categories: local business and startups (high-growth entrepreneurial businesses with an aspiration to grow very large and aren’t geographically bound)
  • 03:04 – “Know When to Quit Your Day Job”
  • 03:15 – Sean, his coauthor, had a book that talked about 100 or so characteristics of successful companies
  • 03:30 – There are lots of good books on entrepreneurship, but the challenge with those is that people don’t know if the actual idea is any good
  • 04:10 – “Startup Opportunities” is a book that says the execution is what’s important and gives advice on what to think about to increase your chances of starting a good business
  • 04:36 – Brad’s biggest takeaway from the book is the notion that your idea needs to be 10x better than the existing ideas; not just incrementally better
  • 04:50 – Local businesses are different, as they are geographically-based and don’t have to be 10x better
  • 05:08 – It gets you out of incrementalist thinking
  • 05:20 – How can people execute better?
  • 05:26 – Founders can surround themselves with people who have been successful; build a mentor network of people who will put energy into what you are doing
  • 05:45 – Mentorship doesn’t have to be hierarchal; mentors can be successful peers, too
  • 06:06 – Its difficult to be a solo founder; most successful businesses have multiple founders or people that were there and instrumental at the beginning
  • 06:56 – Don’t do it all yourself; get others to help you execute better
  • 07:14 – Radical self-inquiry: Constantly try to learn more about yourself as you develop your practical skills
  • 08:19 – Brad’s experience with radical self-inquiry
  • 08:24 – Brad was president of a company for 7 years; he didn’t like the job and reflected on it after they sold the business and he had a staff role with the company that acquired them
  • 08:56 – He was an angel investor and an active VC; it made him realize that he didn’t like being a CEO and that he couldn’t do both effectively
  • 09:38 – Another example of radical self-inquiry was the decision to move based upon where they wanted to live instead of moving based on work
  • 10:50 – Boston was never home; they wanted to choose a place, not be forced into a place
  • 11:30 – Techstars has accelerator programs and activity all over the world and Foundry Group is based out of Boulder; it all came out of his own sense of self and importance
  • 12:00 – What are the realities of capital raising that entrepreneurs need to understand and accept to be successful at it?
  • 12:10 – Do or do not, there is no “try”
  • 12:27 – Envision that you’ll be successful, but accept that you may not be successful
  • 12:40 – Understand what you’re raising, why, and from whom; define your own next level
  • 13:50 – Focus on investors that are appropriate based on your amount and your “why”
  • 14:23 – View your fundraising as a key milestone; use the money to build something useful and don’t put too much weight on just the fact that you raised the money
  • 14:56 – Brad’s latest investment: Looking Glass Factory
  • 15:10 – They make a 3D holographic image display that you can interact with spatially; HoloPlayer One and SuperPepper (experimental) are a couple of their products
  • 16:11 – Computer-human interaction creates an immersion collaboration experience
  • 17:12 – Why do women entrepreneurs only get 2-3% of the funding, and how can that change?
  • 17:18 – Brad’s been a part of the National Center for Women Information Technology for a long time where the discussion has been prevalent
  • 17:29 – The alliance tried to get more women and girls in IT; there weren’t visible heroes for women in IT to look up to
  • 18:10 – They found women that worked in IT and had successful businesses to interview and showcase
  • 18:22 – Misogyny and bias (conscious and unconscious) create a power dynamic between men and women that inhibits the growth of women
  • 19:00 – Men tend to select men; the venture business tends to be an apprenticeship business
  • 19:38 – Brad hopes that we are in a societal shift that eliminates the frame of reference around power to have a gender link
  • 19:53 – He read Susan Brownmiller’s Book “Against our Will” to understand the objectification of women in war and sports; he feels like we are going through a shift
  • 20:40 – He’s hoping the Trump presidency has caused a tipping point, but it is still a long-term process
  • 21:34 – Does the Foundry Group or Techstars have an effort to improve the odds for women needing investors?
  • 21:36 – Techstars has a number of female managing directors, an aggressive diversity and inclusion initiative, and is working towards changing the behavior around all sorts of things so there isn’t gender conflict
  • 22:38 – The Techstars Foundation’s mission is to improve diversity in entrepreneurship; this goes beyond gender to include people that are incarcerated
  • 23:38 – Foundry as a firm didn’t have the goal to grow, the partners that are there have been there since the beginning and the pool of female VC’s is small
  • 24:44 – With Foundry they focus on other things like advocacy activities and support of female GPs
  • 25:10 – They constantly look for opportunities to invest in women; women in their portfolio has grown over the years
  • 26:03 – They are taking action to participate and behave in a way that is consistent and supportive
  • 25:25 – He is learning and wants to increase his understanding of the issues
  • 27:30 – Brad’s thoughts on business-led apprenticeships
  • 27:50 – The notion of apprenticeships is powerful; you want people to learn and grow despite whether you’d actually hire them
  • 28:03 – The phrase “culture fit:” Hiring for “culture fit” is wrong, you should hire for “culture add”
  • 28:20 – Find people that subscribe to your cultural norms but extend it with new thoughts, ideas, and perspectives; cultural fits decreases diversity characteristics
  • 29:08 – Ask what you can invest in that will add to your experience and perspective instead of simply reinforce it; this can be at any level in your business that you see fit
  • 29:52 – Example: Return Path company that he invested in
  • 30:05 – The CTO’s wife had been out of the workforce for 10-15 years and when she tried to return, it was very difficult due to the “resume gap”
  • 30:40 – Things in the workforce had changed so much as well (skills, technology, etc)
  • 31:00 – Return Ships program: An internship program where they get back into the workforce, get paid, have a role, and hopefully get hired after the program
  • 31:30 – Path Forward nonprofit does “Return Ships” and is doing well
  • 32:00 – Change your culture by bringing in a different kind of person; they can add a new dimension to your organization and change the way it functions
  • 32:24 – Brad’s view on the importance of community and the role of the entrepreneur in their community
  • 33:46 – In EO from early 90s to late 90s, community wasn’t a category
  • 34:00 – Entrepreneurs often feel too maxed out to invest time in their community
  • 34:20 – Some entrepreneurs don’t have a frame of reference to understand what would give them joy in this context: His book coming out that discusses this is called “Give First”
  • 34:55 – When you give first you don’t know what you are going to get back; get a bunch of people to give first so they can get back a significant amount
  • 35:27 – Most successful communities of people have the giving characteristic; entrepreneurs can more clearly define the benefit to themselves
  • 36:04 – Example: An entrepreneurial friend said he didn’t have time to give first and his biggest problem in business was that he couldn’t find any iOS developers
  • 36:35 – He suggested a monthly iOS development meet-up where he could serve pizza, drinks, and beer to his iOS guy and his friends and connections
  • 37:03 – After a year, he was doing well, was giving back to the community, the meet-up was successful and had grown, and his company was known as the one doing “cool iOS stuff”
  • 27:30 – He didn’t know this would happen on day one, but it definitely benefited the business and community
  • 37:46 – Most entrepreneurs spend 20-40% wasting their time; figure out how to spend 10% of your time doing something in the community
  • 38:50 – The contribution to your community shouldn’t take away from you, it should feed your soul and give you joy
  • 39:35 – Are there ways that people give that isn’t “correct”?
  • 39:55 – On a personal level, Brad believes in Adam’s take in his book “Give and Take”: The people in life that are givers are happier and more successful
  • 40:20 – If you are giving out of obligation rather than through radical self-inquiry, it won’t work for you or your success
  • 41:25 – External reasons and justifications are not good or sustainable reasons; success in the absence of joy is pointless
  • 42:31 – What is Brad’s view on depression?
  • 42:37 – He talks openly about it because he believes it should be destigmatized
  • 42:44 – Most entrepreneurs that he’s worked with have depression, anxiety, or simply low mental health
  • 43:10 – The challenges of human society are nontrivial; he has clinical obsessive compulsive disorder and was very ashamed of it when he was diagnosed
  • 43:45 – The shame is unhealthy and a societal norm that has been created; people have trouble accepting it and realizing that they can be successful and still manage these issues
  • 44:25 – For Brad, he destigmatizes it by being open about it and discussing it with other entrepreneurs and their teenagers
  • 45:18 – He helps entrepreneur parents understand their children
  • 45:40 – This goes back to diversity; he can’t speak for women or people of color, but he can speak about his own diversities like his OCD and Jewish background
  • 46:30 – He tries to learn, teach, and get rid of stigma and bias how he can
  • 47:31 – Brad has had one suicidal ideation that he wrote about in his book “Startup Life”
  • 47:40 – He and his wife made a rule that he would always tell her if he had suicidal thoughts
  • 48:00 – The one time he had that thought, he told her and felt supported and safe
  • 48:25 – His great-grandfather committed suicide during the Great Depression; he was an entrepreneur
  • 49:00 – Processing this information helped him understand his own psychology, identify with it, and soften the relationship with it
  • 49:58 – Speaking openly about mental health is important during the journey; EO groups have helped create the space for support in that realm
  • 52:15 – He started the Boston and Colorado EO chapters; he was also very active in YEO


Key Points:

  1. Surround yourself with people who have been successful; work directly with others to help you execute better, and always participate in “radical self-inquiry.”
  2. When trying to raise capital, understand what you’re raising, why, and from whom; you must define your own next level.
  3. Contribute to your community in a way that feeds your soul and gives you joy.


Resources Mentioned: