My Story

Who I Am

I am obsessed with understanding the drivers & derailers to sustainable entrepreneurial success…what drives success over the long run and how we can enjoy peak performance and drive while minimizing the toxic side effects of fear and avoid exhaustion. How can we escape the syndrome of “Just Getting through (or surviving) the Next xyz Years?” This blog is my journal of this quest.

I have invested in over 70 companies, completed more than 400 financings, looked at over 20,000 business plans across three boom/bust cycles. I grew up in California coding during the PC revolution, worked on Wall Street during the rise of the Buyout shops and started in venture at start of the Internet Revolution almost 25 years ago.  I focus on blockchain, commerce and next gen technologies applied to industry. Companies I’ve backed include:

  • Dollar Shave Club (acq Unilever $1B)
  • Facebook (IPO…yes, still hold my stock)
  • SMS-Assist (valued $1B)
  • Playdom (acq Disney $560m)
  • Mapbox (valued $560m)
  • TicketsNow (acq IAC $350m)
  • Lefthand Networks (acq HP $360M)
  • AwesomenessTV (acq Dreamworks $110m)
  • FeedBurner (acq Google $100m)
  • Others 9 figures include: Honest Company, Signal, Airmap, Performics

My pride and joy are my three wonderful kids. I split my time between California and Chicago…Midwest authenticity meets California optimism/tech DNA.

What I Believe

In the end, contentment, success and purpose come from dedicating ourselves to becoming our highest versions (mastery) in service to others (whether it be customer needs, employee growth, solving world problems or simply raising our families). We feel happy & successful when we have a sense of progress forward…towards Arete (greek concept of personal greatness/highest version).

Companies are living organisms whose primary goal is to solve specific customer needs, to give back to society while elevating its employees through both personal and professional development. Profits and competitive advantage stem from doing this.

Being an entrepreneur is both heroic and really hard. You are creating greatness from an idea/vision but are playing in the most darwinistic of environments.  Everyone is capable of success if he/she is self-aware, embraces personal blindspots, has self-mastery of fears, shadows & emotions and is dedicated to abundant thinking (win-win). My job as a venture capitalist is to help you on this journey (ups & downs) and, thereby, increase the probability of our success.

Iʼve seen too many incredibly successful entrepreneurs reach the finish line but at significant personal cost (health, family, relationships). There is an erroneous belief and cause at its heart: if I lose my fear, I will lose my drive.

I’ve been on this dysfunctional dopamine dog biscuit hamster wheel. “Happiness will be the next win or accomplishment” we tell ourselves.  Iʼve compared notes with many successful entrepreneurs on this unnecessary toxicity. The traditional playbook is about grinding it out, FOMO angst, not being enough and comparative living. While motivating in the short-run, it drains you and sucks the pleasure out of the journey. Itʼs time for the Red Pill and to see the Matrix. We all can be our best selves, realize success while enjoying the ride. It just requires a different playbook and approach. Let’s work on this together.

The Venture Covenant

There is a false dogma around the VC/Entrepreneurship relationship…supported by bad behaviors on both sides. You feel a need to manage your investors & board, to not show weakness and present to us. We fail to fully listen, dictate desires or fears and financially optimize our investments. Trust and open communication are our most precious assets which we squander away as a result. In reality, we are on the journey together with a common enemy (Darwin). We must hang to together or “surely, we will all hang separately.” We need to optimize our chances for success, row together, remove unnecessary drama and minimize self-inflicted wounds (the majority cause of pre-mature death). Over the years, I’ve seen both the good and the awful with this relationship. So, here is my rough draft of a Covenant with My Entrepreneurs

My Promise
My ExpectatioN
Be committed to your personal & the company’s success Be self-aware and embrace your blind spots
Respect that this is your company but provide guardrails & accelerants Don’t self-optimize. Your employees and I depend on you
Show up rationally, empathetically and, “first, do no harm” Don’t let fear or ego dictate how you manage and lead
Be open and frank in my communication Be open and honest in your communications
Seek homework from you to knock down barriers & accelerate growth Say “no thanks” when I’m not helpful
Respect your boundaries Acknowledge when you need help or don’t know
Honor confidentiality Embrace this as a partnership, not as a necessary Evil
Encourage experimentation, quick iterations and respect failure Don’t feel obligated to carry the world on your shoulders