A New Approach to Venture

I have been developing a different approach and strategy for venture investing (and life in general) for almost a decade. In addition to investing at Pritzker and Crown, I have been evolving this new venture model with personal capital. Entrepreneurs (and humans in general) are given an oxygen mask and told that the Everest Summit is a day’s hike and are sent on their way. We have our strategic and everyday frameworks, tools, and experiences. We have patterns and behaviors set decades ago within our families and schools. However, within half a day, the first Everest storm hits hard, and we realize that we are missing the most important tools of all…the human ones. We wonder why the journey seems complex, uncertain, and draining.

Being a human centric design enthusiast, I wondered: What if a leadership/coaching platform had a child with a venture fund to help guide or Sherpa entrepreneurs, students and others on their journey? What if Jerry Colognna of Reboot was right when he said: “We believe that in our work lies the possibility of the full realization of human potential. Work doesn’t have to destroy us. Work can be the way we achieve our fullest selves.”

I also wondered what the end goal of life (and work) was. What is true success? I have spent the past eight years reading hundreds of books going back thousands of years on “the good life.” These ranged from Aristotle & Socrates to the Stoics (Aurelius, Seneca) to the Upanishads, Buddha, Confucius, and Tzu to, Emerson, Thoreau, Campbell, and Frankl. I added books on specific foundational areas like Sleep by Matthew Walker, Meditation by Chodron, Davidson, Habits by Duhigg, and Clear and nutrition by Pollan. I seeded a company that is the best I’ve found on “Blinkist-like summaries” of these great texts for everyone (get the Heroic app here). In the end, wisdom has not changed over the centuries, just the metaphors. If you read Meditations by Marcus Aurelius (emperor of Rome and the most powerful man in the world), it reads like the challenges of a modern-day executive, parent, and spouse.

I wanted to create an essential guidepost to measure progress to simplify all of this. I wrapped it in what I call the Saint Peter test (you can replace this with whatever metaphor works for you…Eulogy test seemed too depressing!). If you got hit by a bus today and were in front of the proverbial Pearly Gates and had to describe how you had lived your last month or two, how would that go? Would you feel that you “owned every second that this world could give,” or were you stressed, drained, reacting, waiting for tomorrow to be your time? Did you appreciate and were grateful for all the people and wealth in your life, or were you heads down battling yet another drama?

In the end, I settled on three parts to the test: Energy, Impact, and Presence. ENERGY: life is simply energy…when we are energized, we are happy, and when we are drained, we are depressed. So, does what we do in business, family, and life increase or decrease our energy daily? IMPACT (campground): in his bestselling book, How Will You Measure Your Life, the iconic HBS professor Clayton Christensen posited that the ultimate measure is not money or houses or titles but How Many People’s Lives have you changed for the better while on earth? Today, did I leave the campground cleaner than when I arrived in the morning? PRESENCE: did we show up to our own movie today, or were we down some rabbit hole? My favorite coaching program (one of the top platforms in the Valley), CLG (Conscious Leadership Group), asks how intentional we are in living our daily lives (reactively/impulsively or proactively). Are we coming from a place of trust/abundance that life works for us OR below the line, from a place of fear/scarcity that life happens to us? Was I the architect of my life today? Said more elegantly by OneRepublic (click on the link below for their outstanding, award-winning music video on living life).

I owned every second that this world could give
I saw so many places
The things that I did
Yeah, with every broken bone
I swear I lived

– OneRepublic, I Lived

I believe that entrepreneurship is a proxy for life. The future is opaque and we are faced with daily challenges that test our resilience, our talents and our values. These are just stations at the gym to grow. Ironically, venture capital has approached this highly human endeavor with a somewhat harsh, quantitative, and dehumanizing approach. This mirrors how many of us approach life. We have our responsibilities, our goals and our resources. But when the 8-10 year cycle of life (heck, just daily life) comes swinging through to clear out the brush (if not the forrest) like it is currently doing, we realize that we are missing many of the most important tools.

I was curious if this was just me, so we interviewed over 100 entrepreneurs and asked them one simple question: To help you most, how do you want your VC to show up? Ironically, few had ever been asked this question (I have to love the cobbler’s kids having no shoes). The top response was not to help with hiring or fundraising or strategy (though all are important) but rather, “Who can I turn to, and what can I do on a Sunday Night when the ghosts and demons are running through my thoughts and sleep?” The second response was, “Scaling from $1m to $10m to $50m to $100m is brutal. Can you help me become a Superhero/the highest version of myself? I am dog-paddling in the rapids and need to learn and grow into being a leader (or parent or spouse or…).” Both of these fall into the Human column, not the traditional buckets of Strategic or Tactical.

So the hedonic game plan seems to be breaking down in a big way…that happiness is the next blue ribbon, that vulnerability is a weakness, being right is a necessity, anxiety & fear win out every time. That life is dangerous & happens to us. I have spent years building out alternative tools, modules, and exercises. These are based on wisdom across thousands of years, are tested effective in the application (not just concept), and are self-sustaining (vs. the grinding anxiety models).

To be clear, I don’t have all the answers. My kids joke, “Dad, do you ever listen to your own advice?” However, I do know that the traditional models taught to us as kids and school are broken, and there are age-old, consistent wisdom and tools, as well as modern-day leadership platforms that work much better.

FORGE: personal growth and excellence are forged in the fires of entrepreneurship and life. Here’s to an energetic, impactful, and intentional next chapter!

The power of the Entrepreneurial Mindset

Coming

How to realize it?

Coming