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A Bunch Of VCs Went On A Retreat. Here’s What Happened.

Steve Schlafman
Steve Schlafman
4 min read
A Bunch Of VCs Went On A Retreat. Here’s What Happened.
Photo by Ralph (Ravi) Kayden / Unsplash

This past weekend I had the good fortune of participating in the first RebootVC Bootcamp. For those of you who don’t know Reboot, it’s a values-driven organization led by Jerry Colonna that primarily helps founders and their teams deal with the constant ups and downs of startup life. At the most fundamental level, Reboot is a personal development company that offers bootcamps, executive coaching, 360 reviews and a variety of other programs to help leaders discover their true selves. Reboot also publishes useful and powerful content including a phenomenal podcast hosted by Jerry. I can’t say enough great things about this organization, its team, and their mission.

This formula is the essence of Reboot:



Jerry and Brad Feld, a Partner at Foundry Group and Co-f0under of Techstars, decided to run a bit of an experiment. Instead of facilitating a boot camp for founders, they tailored a program designed specifically for venture investors. Jerry and Brad have over forty years of combined investment experience. They’ve seen the good, the bad and the ugly. Most importantly, they deeply care about the startup ecosystem and believe in paying it forward. When they’re in a room together the discussion is always authentic, insightful and inspirational.

Over the weekend, sixteen investors from funds of all sizes and both coasts descended on Boulder, CO to speak openly about our challenges and to learn how to improve our interactions with our portfolio companies and the founders we work with. Jerry and Brad worked closely with the group to help us uncover our authentic leadership styles and provided practical skills for managing the array of feelings that can be triggered as we navigate the startup ecosystem. The goal of the weekend was to help each of us become the best board member, investor, supporter that we can possibly be.

A few days have passed since the retreat ended and I’m still processing the experience because I found it powerful both personally and professionally. I learned a tremendous amount about myself and the other participants. This was extremely useful for me because I’ve found that investors rarely open up to one another about work, life and everything in between. Throughout the weekend, I was able to recognize that many of the things that I wrestle with as a board member and an investor are quite common. Just as important, I gained more empathy for entrepreneurs and their daily struggles.

As I look back on the weekend, there are many teachings and lessons that I brought back to New York with me.

  1. When your inner and outer self aren’t in sync, it creates personal dissonance that results in being afraid, feeling unsafe, etc..
  2. If you ask a founder how you can help, it means you haven’t been listening close enough. Be fully present.
  3. Being a great board member or investor isn’t about having all the answers and fixing things. Don’t underestimate the power of listening and supporting.
  4. There’s tremendous power in the question, “How are you?” Show you care. Find out what’s really going on. Be human.
  5. Many people, including founders and investors, are dealing with things such as depression, anxiety, imposter syndrome, addiction, etc.. People in the startup community are human…not super human.
  6. Before making a significant decision, visualize the result and impact on your life. In other words, “try on” your decision each morning or night. Act it out. Write it down. Internalize it.
  7. The human soul is resilient and can recover from nearly anything including massive failures and personal adversity.
  8. We’re all learning on the job and no one has all the answers.
  9. Don’t rely too heavily on “playbooks.” You should always question them and / or throw them out the window.
  10. Having a beginner’s mind is a beautiful perspective because it enables continuous fresh thinking.
  11. Don’t hide from your shadow qualities. Instead, learn to shed light on and embrace them.
  12. Be mindful of the pronouns that you use (e.g. you, I, our, etc.) in discussions with founders and partners. There’s a big difference between “I’m sorry” and “How are you doing?”
  13. Sometimes it’s easy to blame changing industry dynamics, the macro environment, and other actors when things aren’t going well. When you find yourself doing this, take a look in the mirror.
  14. Journaling is a wonderful and powerful tool that can extract ideas and emotions.
  15. Finding work / life balance is critical to maintaining healthy relationships and overall wellbeing.
  16. Every firm is a direct extension of the partners and values. Seek to build a firm that you are proud of and would want to work for.

As you can probably see from these learnings, the bootcamp went deep and had a profound effect on me. I should note that I’m speaking on behalf of myself and not the entire group. These are my conclusions based on the experience that I had. I recognize that everyone sees the world in a unique lens and brings a different perspective to the table.

In closing, I’d like to extend a heartfelt thank you to Jerry, Brad and the rest of the participants for creating and embracing such an open and safe space. It was a truly magical weekend. I have no doubt that many of the participants will be co-investing together and positively impacting the startup community for many years to come. If you’re a founder looking for a mindful investor, I highly recommend you seek out any of the Reboot participants. They’re all special individuals who truly care about being great partners, building quality firms and impacting the world. In fact, I believe this crew represents the future of the venture industry because they’re guided by their values and their hearts.

Venture Capital

Steve Schlafman Twitter

Exec coach. Writer. Student of Change.


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