The first thing I love about startups is that you get to stand for something.
I don’t think that this is true of every startup, and I don’t think that startups are the only place you can truly stand for something, but, I think startups are a fertile place to say, “this is what I believe in, and I’m going for it.”
The first match that I made with CoLife (we match renters to the massive supply of owner occupied homes) made me cry. We’ve had racial issues in Charleston, South Carolina, where I live, for a very long time (40% of all North American slaves came through Charleston, and 80% of African Americans can trace someone in their family to Charleston). The first match I made was with my retired, white, high school history teacher who lived in a suburb of Charleston that had KKK rallies within the last 25 years, with an African American 28 year old male who was saving money to buy an engagement ring. They both attended the same military college in Charleston, The Citadel. I still have a photo of the two of them meeting.
After I made that match I realized that for all of my ranting about racial issues in my city, one small act of entrepreneurship had done more to concretely express my beliefs. I quit ranting and got to work.
One of the two things that I care most about is human connection. It brings me joy. I think so many of the world’s problems—loneliness, housing, mental health, elder care, even climate issues—result in part because of a lack of it. In my personal life I throw parties, I talk to strangers, I ask questions to really try to get to know people. I write books about it. I try to live by the mantra that I want my desire to be known to be greater than my fear of being judged.
To me, CoLife is far less of a housing company than it is a company about human connection. And I think that if we can solve for that, and we can, that we’ll not only solve a large portion of our nation’s housing problem but also create a very large and successful business.
Startups create an actionable way to stand for something.
The second thing I love about startups is that it creates focus and simplicity.
In startup land, the question you get asked a lot is how long is your runway. It basically means, how long can you stay alive? There are three ways to stay alive in startup land. You can spend less money. You can raise more money. Or you can generate revenue.
The beautiful thing about this is that it brings massive focus (or at least it should) into what’s most important to stay alive and create success. We have to watch our expenses. We have to convince people to invest in what we’re doing. We have to build success fast enough to create a thriving business before we run out of time.
And I love this, because, while I unfortunately waste time every day staring at my phone, trying to focus on the things I want to do and avoid the things I don’t want to do, the startup life reminds me that all of life is a runway.
We ought to do things to prolong the amount of time we can be here, like eat well, work out, drink less, and meditate. We ought to convince others to join us and invest, the people we want in our lives, our friends, our family, our coaches and advisors and the people that bring us joy. We ought to do something meaningful with our lives, something that fits our calling, our skills, our gifts, that positively impacts the world, that regardless of its success or failure, brings us purpose.
I put aside money for retirement, and I have long term goals, but to be honest, a lot of that has always felt like a bit of a scam asking me to trade my present for a not guaranteed future. Startups are the opposite of that. In startup land, you only live to see the future if you take the right action in the present. It’s a better life, in my view. So get focused, and cut out what isn’t necessary.
The third thing I love about startups is that they are a calling, and a calling makes you grow.
A calling speaks for itself. Again, there’s a lot of startups that have nothing to do with a calling, and there’s a lot of callings that have nothing to do with startups, but the overlap is that startups create fertile ground for a calling, because the fundamental requirement of a calling is courageous, deep perseverance in the face of fear and the unknown.
I’ve chosen a number of difficult journeys and long projects, living homeless, driving a car from Mongolia to London, writing books and starting businesses, because I see them as part of my humble calling. I’ve also found them to be great tests of emotional, psychological, and spiritual growth. It’s in the face of the unknown that you get to test your courage. It’s in the loss of approval that you get to test your values. It’s in the risk of losing security that you discover a deeper security.
Startups provide fertile ground for growth because there is no guarantee and they are exceptionally challenging. The stats are that your startup will fail. Some days you feel certain you’re going to be a billionaire, and within 36 hours you’re certain you’re going out of business and your life is over.
The entry point to startup land is being smart. The entry point is being exceptionally hard working. The entry point is being resilient. But beyond all that, there are simply things that are out of your control, like luck, and fate, and having the right idea at the right time.
And well, all of life is like that. You might get hit by a bus. You might win the lottery. You might have a building fall on you in your sleep. You might have a child with a disability. People, like they did with Vincent Van Gogh, may never recognize your work.
But if you stay with it, you get the chance to grab life by the horns and grow in a way that only a calling can make you grow, and you just might find that a calling is its own reward.
Each of these things, getting to stand for something, living a life of focus, and choosing a calling that makes you grow, might seem dangerous, but it’s a far better life, I’d argue, than standing for nothing and letting others decide your fate, living a life of distraction and procrastination, and giving up the thing you’re meant to do but might fail at for the thing you can be successful at but doesn’t challenge you or make a difference in the world.
And so that’s what I love about startups. Pick the thing you think you’re meant to do with your life and go do it, in the rain or the snow, good times or bad, living in a mansion or a ditch, and you just might find that you’re standing for something that really matters while living a life of focus and a calling, and, just maybe, there you’ll discover joy.
P.S. If you liked that, here are free downloads for the books I wrote: The Definition of Success tells the story of the year I voluntarily lived homeless and how I believe we can redefine success. Driving w/ Strangers is a book of meditations about my drive from Mongolia to London.
