Remembering When Elon Almost Went Under

To all the aspiring entrepreneurs battling through COVID: With the hopeful Crew Dragon launch on Saturday, Elon will show us yet again what the human spirit is capable of and usher in manned space flight’s next chapter. However, I remember & experienced when not one but all three of his companies were on the brink […]

The Two Arrows: Productive Pain vs Unnecessary Suffering

A lot of things seem upside down in the world right now. Many plans or dreams are deferred, if not upended and we feel anxiety in the face of uncertainty. However, this is a core part of flourishing. In entrepreneurship and in life, disappointment (AKA pain) is inevitable. However, suffering, which drives most of our […]

Embracing Life’s 8-10 Year Cycle

Roughly, every eight to ten years, life seems to cycle through like a brush fire to clean up the excesses of the past decade. I’ve experienced this both on a personal and business level four times now (in addition to the 1987 one day 23% market drop).  The Great Financial Crisis cycle has abruptly ended […]

If I Lose My Fear, Do I Lose My Drive?

I hear this a lot from entrepreneurs and students. “If I lose my fear, do I lose my drive?”.  Two things are implicit in this question…1) fear/anxiety is an essential motivator for success and 2) being driven by anxiety & fear (often a default) has an unsustainable & unacceptable cost. This is a false trade-off…success […]

Hypothesis: Do You Know the Bet You’re Making?

Since the future is unknowable, by definition, we are all making bets in our life, testing hypotheses and probabilities. However, often, we aren’t aware we are making a bet or what that bet is. As a result, we don’t prioritize nor focus on the key things. This applies to careers, relationships, schools or starting companies […]

Enough: Your Savior or Your Demon

My partner, Carter, has hypothesized “…that behind every driven CEO is a 6 year old child seeking its parents’ approval”. In these formative years, we start the dance with being enough (and feeling we aren’t enough). We create coping mechanism to deal with this discomfort whether it be over-achieving, addictions, Instagram posts, compulsive behavior, etc. […]

The Dawn of a New Era in VC & Tech

Tech and VC are entering the Dawn of a New Era. Our industry goes through thematic cycles roughly every 10 years (in addition to the “15 year tech” cycle).  The 2020’s will be known for the rise of Stakeholder Capitalism. We will significantly change how we build companies and what their greater roles are. There […]