A couple years ago, my wife Crystal and I were cleaning out our garage in Truckee when we came across an old notebook of mine from when I lived in Ireland at age 20. Back then, a friend had asked me, “What do you want to be when you grow up?”
Despite never having heard of venture capital, I went on to describe a job that would involve “a lot of time on the phone negotiating” and overall “high risk, high reward.” I envisioned it as a very lean operation, possibly working out of a bare warehouse, and I would do it half-time from the mountains and half-time from the beach. Last, I predicted that whatever this job was, I would “be the best” at it and then “quit at 40 to try my hand at something else entirely.”
Well, though these days most of the negotiation takes place over email, I did go on to risk every dime I had, more than once, and build Lowercase Capital. As prophesied, Lowercase has earned its spot among the best funds ever despite never having formal office space. Instead, I’ve always worked out of my homes in Truckee, California, and Big Sky, Montana (mountains), and Los Angeles near the water (beach).
And underlying all of this? In a matter of days, I am going to be 42 years old. Two years late.
Thus, to dig up the deeply buried lede…
I am retiring from startup investing.
It’s hard to leave all this behind right when things are going so well. I’m good at what I do and still improving as I learn from mentors, founders, partners, friends, family, strangers, my own investors, and the experience itself. The better I get at investing in and helping companies, the result is more founders who are excited to work with me and more of my wonderful limited partners insisting I take piles of their loot to keep it all going. People offering you risk-free money is generally considered a positive thing. But, as I have increasingly realized…
Startup investing is one of my things, but it is not my everything.
For the last few years, I’ve tried to do this job part-time. Crystal and I brought on our partner Matt Mazzeo to take over the day-to-day deal leadership for our most recent fund. He’s great and that fund is already doing exceptionally. But my personal style of startup investing doesn’t work when I’ve just got toes dangling in the water.
The only way I know to be awesome at startups is to be obsessively focused and pegged to the floor of the deep-end gasping for air. I succeeded at venture capital because, for years, I rarely thought about or spent time on anything else. Anything less than that unmitigated full commitment leaves me feeling frustrated and ineffective.
As you’ve heard me say on the show, if I’m not all-in, I’m out.
So what does this mean for Lowercase Capital itself?
We will continue to passionately support our current portfolio companies. When we invest in a startup, we make a commitment to help them for years and years. That isn’t changing. We just aren’t going to invest in any more companies going forward and we won’t be accepting any money from investors.
In addition, our partner Matt Mazzeo has something exciting to announce soon. I don’t want to steal his thunder. So, I’ll just note that Mazz has been a spectacular investor and an even better friend and collaborator. Crystal and I deeply appreciate his insight, his humor, his hustle, and above all, his high integrity. We couldn’t imagine building this business with anyone else, and especially not with better hair.
So, all this sad news aside, when do you start filming Shark Tank again?
I’ve decided not to film Shark Tank again this season. There simply isn’t a way to do the show without investing in a bunch more companies.
The love I got from you guys during my two seasons on the show was incredible. It choked me up at times. When I first sat in that chair, I wasn’t sure what might happen and what you all might think. Turned out, the Twitter feedback was teeming with high fives, my episodes’ ratings were strong, the critics loved it, I invested in some fantastic companies, and most importantly, I had so damn much fun. You all made Friday nights so special for me.
Funny enough, the person who is most bummed out to hear I won’t be back is Mark Cuban. Despite what you might surmise from on screen, he and I are actually good friends, just really competitive good friends. I’ll miss working with Mark, and all of the other Sharks. Each of them has been incredibly generous and warm to me and I am proud of all the episodes we made together.
Wait, really? You’re just walking away from Shark Tank?
I love taping the show. You can’t necessarily tell when watching at home, but those pitches are usually an hour long each and many are emotional, hilarious, and inspiring. Watched by millions every week, across red and blue states alike, it’s refreshing how many new people from outside my bubble continually reach out to talk with me. The show quite simply embodies the American Dream.
Sadly, like I mentioned above, more investments makes it impossible for me to move on. So it’s time to walk away. Or, as we would say on the show, “I’m out.”
So, Chris, you’re done with media and entertainment?
Whoa, let’s not get ahead of ourselves. I’ve been enjoying the hell out of these new experiences. TV stuff can be a hoot and I learn so much by interacting with audiences outside of my bubble. Even the quirkiest opportunities, like my upcoming appearance on Celebrity Family Feud, have taught me something and brought me a lot of laughs.
In one particular example, I’m very excited about Zach Braff’s new pilot for ABC based on The Startup Podcast. Zach, ABC, and Sony cast me to play myself. Imagine having to memorize lines that are actually things you’ve already said before in real life. Shooting that first episode was a thrill. We will know soon if the series gets picked up. Exciting stuff. Stay tuned.
I’m also launching a podcast. Because, I mean, the world desperately needs another podcast, am I right? Not to be a tease, but the format is different from anything else I’ve seen out there and the subject matter is hopefully boundless, eye-opening, and a little cathartic. Did I already say stay tuned? Well then, glad I don’t have to mention it again.
Wait, is quitting all this stuff a prelude to running for political office?
If you follow my Tweets, you know, my attention and anxiety have been increasingly focused on the plight of our democracy. I don’t say that lightly. I think the institutions, principles, norms, and traditions that make the United States of America genuinely exceptional are at serious risk. It has been hard to think about anything else.
As a rich white guy, being an activist/loudmouth in the #resistance often means taking up political positions that are against my own apparent self-interest. These oppressive zealots in the White House are giving people like me a massive tax break and adopting policies that make my already charmed life even easier all at the expense of those Americans who most need our help. But I was raised by parents who instilled in me a deep sense of gratitude and an obligation to give back the gifts I’ve received. My life has been guided by experiences here and abroad that highlight how much we are all in this together.
This is a good time to note that my success would not have been remotely possible without robust public education, access to healthcare, government creation and nurturing of the Internet, federally funded research and science, and the talents of brilliant people from literally around the world. My career would not have progressed without the leadership and contributions of immigrants of virtually every race, ethnicity, and faith. Period.
So, I owe it to do what I can to help, now more than ever.
That kinda sounds like you’re running for office.
I assure you, that’s not going to happen. Nevertheless, I am spending a great deal of time meeting with all of the beautifully spontaneous and decentralized organizations that have been popping up in the wake of our electoral calamity as well as dozens of candidates at all levels of government. I find so much hope in the new wave of leaders and builders who are standing up during these times and I want to be there to support them. I will have more to say about this in the days ahead, but, you know the drill.
So how else are you going to spend your time?
You mean beyond fighting a despotic regime, doing more television, launching a podcast, all while raising three wonderful kids under six? Fair question. My favorite author, Buckminster Fuller, wrote:
“We are blessed with technology that would be indescribable to our forefathers. We have the wherewithal, the know-it-all, to feed everybody, clothe everybody, and give every human on Earth a chance. We know now what we could never have known before-that we now have the option for all humanity to make it successfully on this planet in this lifetime. Whether it is to be Utopia or Oblivion will be a touch-and-go relay race right up to the final moment.”
Crystal and I are committed to doing all we can to ensure Utopia wins. We are passionate about solving our climate disaster, criminal justice reform, and women’s issues and we have a couple irons in the fire. We are also deeply committed to paying forward the luck and opportunities we have enjoyed in our space. So we’ve been quietly backing the next generation of investors, but specifically women and people of color who have been starting venture funds. A lot more to come across all of these fields.
Anything else to add, Chris? Or are you just stalling?
Someone must be dicing onions in this room because it’s getting hard to see my screen.
I feel so grateful for all you have given me. Not just our investors and entrepreneurs. But all of you. I am very lucky.