Registration is open for the 2022 Q4 Leadership Bootcamp, which is happening in Boulder, Colorado, on Nov 10-13, 2022.
Regular readers of this blog know about my long-time (back to 1996) friendship with Reboot co-founder and CEO Jerry Colonna. What you may not know is that several years ago, Jerry and his partner Ali Schultz moved exactly 0.8 miles away from me (there is one 40-acre parcel of land between us.) In the evening, when we are both in Boulder (well, Longmont), he sits under his Cottonwood Tree, I sit 0.8 miles away on my couch next to my pool, and we text and wave at each other.
I’ve been to several Reboot Leadership Bootcamps as a special guest. They are unique and powerful experiences for entrepreneurs. As a bonus, the Reboot Retreat Center is actually on my property in a building called “The Carriage House.” Amy and I don’t charge Reboot for the use of The Carriage House – it’s our gift to entrepreneurs and Reboot for this amazing experience.
If you’re looking to reboot and refresh your leadership, join Team Reboot this November 10-13, 2022, in Boulder, CO, for their fall Leadership Bootcamp.
Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up.
Seriously, go buy it right now. I’ll be here when you return.
Regular readers of this blog know that Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who we still work with as CEO of Blocknative). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis, but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with my 23 official years of marriage to Amy.
If you want to get a feel for Jerry, listen to one of my favorite Reboot podcasts, where we flip the script and I interview Jerry.
Jerry has been on the road promoting the book the past few weeks. Dip into a few of the podcasts and interviews or get a taste on the CNN interview that he did.
Reboot: Leadership and the Art of Growing Up is extraordinary. It’s 100% Jerry, on every page, and is the book he was put on this planet to write.
If you are an entrepreneur, investor, leader, or human being, do yourself a favor and read Reboot: Leadership and the Art of Growing Up. I’m serious – it will change how you think about yourself, leadership, and life.
I’ve long written about the stigma around entrepreneurship and depression / other “mental health-related issues.” I was delighted to see two articles in the last day about others addressing this.
First, Felicis Ventures is committing 1% on top of every check the firm writes in non-dilutive capital earmarked for “founder development” in coaching and mental health. I love the way Aydin Senkut has characterized what they are doing and why they are doing it.
“Felicis’ bet is that by making such resources available and publicly known, founders won’t feel too proud, or too much pressure to seem successful, to address personal and team issues. Tactical marketing help can only go so far, Senkut says, when founders aren’t telling their investors that they’re unable to sleep from anxiety, or not speaking to their cofounders.”
Next, Mahendra Ramsinghani has a long article in Techcrunch titled Investors are waking up to the emotional struggle of startup founders. In it, he references a bunch of stuff, including work that Jerry Colonna and the team at Reboot have been doing around this issue. He also points to the survey he is doing for his new book titled Depression: A Founders Companion.
If any of this resonates with you as a founder, (a) go complete Mahendra’s survey, (b) connect with Reboot, or (c) send me an email to connect you with Mahendra or Reboot.
If you are a regular listener of the Reboot Podcast, you’ve heard Jerry Colonna masterfully interview many people. And – if you aren’t a regular listener, go sign up and give it a try.
In Episode 78: When Did You Start to Listen to Your Heart, I turned the tables on Jerry and interviewed him. We’ve been close friends for 22 years and I felt like it was time someone interviewed him on his podcast. I suggested it to him and his team, who either rolled their eyes or jumped for joy. Either way, it is now up.
I listened to the final version during my run yesterday. I smiled a lot, snickered a little, and grimaced a few times. If you want a taste to entice you to listen, here are a few of the quotes from the show highlights that jumped out at me.
It’s all Jerry for an hour with a little bit of me nudging the discussion along. None of it is scripted. We didn’t discuss anything in advance. Just two guys, who have known each other, worked together, and have had a deep emotional intimacy together – for 22 years – talking about some things that come to mind about what they think matter.
If you are a reader instead of a podcast listener, the transcript for Reboot Podcast 78: When Did You Start to Listen to Your Heart is also available.
At 18 minutes into this awesome talk that Fred Wilson did at MIT a few weeks ago, he finishes the statement “The best time to invest in something is ...”
“… when nobody wants to invest in it but you.” He adds “And – you have to believe in it and know why.”
Truer words have never been spoken about investing as, or in, VC. Just don’t forget the phrase “and – you have to believe in it and know why.”
Fred is one of my closest friends in the VC business and someone I’ve learned an amazing amount from him since first meeting him in 1996 when he was just starting to work with one of my male soulmates Jerry Colonna.
Watch the video. Listen carefully. Learn from his experience.
Fred – thank you for everything you’ve done for and with me over the years.
Jessi Hempel from Backchannel just wrote an amazing profile piece on my close friend Jerry Colonna. It’s titled This Man Makes Founders Cry. Medium estimates that it’s an 18 minute read and I assert that it’s worth every minute.
I’ve known and worked with Jerry since 1996. I now get to call him my neighbor as he moved from New York to Boulder a few years ago. If you want a taste of our relationship, I’ve written a lot about him over the years. Following are a few recent ones.
There are a few people other than Amy and my family who I love. For example, I love my partners. I love Len Fassler, who remains to this day my most influential mentor. And I love Jerry.
There are many choice quotes in the article, but to give you a taste, here are a few.
Go read the entire article on Jerry. And, if you want more, go listen to the Reboot podcast.
On Saturday night I got on a plane and flew to the other side of the planet, where I am now. I’m in Melbourne, finishing my coffee, getting ready for one last meeting here before I fly with David Cohen to Adelaide for the day.
When I left, I had the voices and energy of 25 people in my head. Last Thursday evening was the beginning of the second Reboot VC Bootcamp at my house just outside Boulder.
Amy and I have a second house on our land, which we refer to as “the Carriage House” and the Reboot gang calls “Chez Feld.” The first floor is an event center that we use for non-profit events. The second floor was going to be a man cave, but my idea of a man cave is carrying my laptop around the house wherever Amy goes and sitting down next to her. The idea of hiding out from her a separate place has never made any sense to me so we turned the second floor into a retreat center which friends and companies in our portfolio are starting to discover and use, especially since it’s a lot less expensive (free) than renting a hotel conference room for the day – and a lot more pleasant.
About 20 VCs from around the world showed up for an intense four day experience lead by Jerry Colonna and his Reboot team. The website is understated about the experience.
“Over this long weekend with Jerry, Brad Feld and Team Reboot, we’ll work to uncover your authentic leadership style and teach practical skills for managing the array of feelings that can be triggered–all in the name of helping you become the best investor/board member/supporter you can be.”
To really understand it, read the following four posts from attendees of the second bootcamp.
I was a little sad to leave Saturday and not be part of everything, but reading each of these posts this morning made me very happy. It’s not just that “VCs are people too”, but that the 20 people who showed up in Boulder for four days opened themselves up completely as they each went down their own path of radical self-inquiry. Jerry and the Reboot team continue to amaze me (and many others) in their magical abilities around personal exploration and growth in a professional context (well – and a personal context.)
For everyone who showed up – thank you for coming and letting me be a part of it. As I sit here on the other side of the world with my soul gradually catching up with me from the jetlag, it’s powerful to ponder that we are all just bags of chemicals.
I recently joined the Defy Ventures board. If you aren’t familiar with Defy Ventures, here’s a post that I wrote after my first prison trip with them at the end of last year.
Early this morning, on my run in Melbourne as I tried to shrug off jet lag, I listened to a Reboot podcast that Jerry Colonna did with me and Cat Hoke, the CEO of Defy Ventures, a few weeks ago.
I had tears in my eyes while running, and I don’t think it was from my pace. Among other things, I’ve committed to bring Defy Ventures to Colorado in 2017. If this is something that is interesting to you either reach out to me or keep your eyes open for a broader fundraising initiative coming up (we’ve already raised 40% of the money needed to do this.)
And – enjoy the podcast. I think it’s one of the most powerful (at least to me) that I’ve participated in.
Today’s #GivingThanks post is for my dear friend Jerry Colonna. When I make a list of non-family members and non-partners who I would want to be stranded on a desert island with, Jerry is at the top of the list.
Before I tell a story, if you want to participate in #GivingThanks to Jerry, please make a donation to Naropa University where Jerry is the chair of the board. I was going to try to create some kind of complicated matching donation scheme since I hadn’t made a gift to Naropa yet this year but I decided to just gift them $10,000 (which I just did now through the website) so I encourage you to support at any level if you want to participate in my not-so-complicated match.
I met Jerry in 1995. I was chair of NetGenesis, which was the first angel investment I’d made after selling Feld Technologies (my first company). NetGenesis had raised some money and had created three different products – net.Forms (a web form manager), net.Thread (a web threaded discussion board), and net.Analysis (a weblog analysis tool). While our customer for each product was the same (a webmaster or a company trying to build a website), we were having trouble leading with all three products. Allaire was eating our lunch on .Form, a company called eShare was picking us apart on .Thread, and this new company called WebTrends was torturing us on .Analysis. A year earlier, none of this had existed – now we realized we needed to focus on one product. We chose net.Analysis and went about selling the other two products to different companies.
Jerry had just invested in eShare. Somehow Raj Bhargava (the NetGenesis CEO) had connected with Jim Tito (the eShare CEO) and worked a deal to sell him net.Thread. NetGenesis got some of eShares equity, eShare got the net.Thread product, and I joined the eShare board.
That started a 20+ year relationship between me and Jerry that I comfortably use the word “love” to describe.
Jerry became partners with Fred Wilson and they started Flatiron Partners. We all started working with SoftBank as affiliates (along with Rich Levandov). I eventually co-founded SoftBank Technology Partners (which became Mobius Venture Capital) and SoftBank (the corporation) became a 50% LP in Flatiron with Chase. We made more investments together. As Jerry and Fred’s relationship evolved, so did mine (with each of them) as we had different kinds of professional and personal connections.
I remember a moment in what must have been 1999, sitting at Jerry’s desk in NY in a dark office (I never really like office lighting so I work without it on and it had turned into evening in NY.) I was trying to get a deal done and it was a stressful mess. The tension of the Internet bubble bursting hadn’t started yet, but I was already exhausted and negotiating basically all the time with everyone about everything. I hung up the phone and put my head down on Jerry’s desk. I wasn’t crying, but I was probably in a parallel emotional zone. Jerry walked in the room, saw me, and wrapped his whole body around me and just covered me up. It was one of those moments I’ll never forget – total, compete emotional intimacy in the context of support. I’m sure he was feeling the same kind of stress and in the moment we just hugged. And then I cried.
Jerry has a super power – he makes grown men (and women) cry in a business context. But that’s the super power – it’s not a business context, it’s life, and he helps us understand that in powerful, unique, and profound ways.
In 2002 Jerry retired from venture capital and went on his own personal journey for meaning. He was an extremely successful VC but woke up one day hating the work, feeling unfulfilled, and struggling with what became a deep depression. I was fighting my way through my own dark shit then so we didn’t see each other often, but when we did it was extremely helpful to me. There was an immediate sense of comfort, of love, of empathy, and of understanding. It didn’t matter what we talked about – we were just there, together, in the moment.
Today, Jerry runs a CEO coaching company called Reboot. Their mission – front and center on their website – says it all.
“We believe that in work is the possibility of the full realization of human potential. Work does not have to destroy us. Work can be the way we achieve our fullest self. Reboot is a coaching company. We help entrepreneurs and their teams deal with the internal ups and downs of entrepreneurship and support the growth they need to improve their performance and their life.”
I believe that Jerry is the best CEO coach on this particular planet. I’ve seen, and experienced, his magic many times. He’s found his purpose in life, and it’s wonderful to see him practice it every day.
Jerry also moved to Boulder last year. That means I see him a lot more in person that I used to. I still have to make a mental adjustment when Amy and I run into him and Ali on the Pearl Street Mall heading off to different restaurants for dinner, but an enormous smile always crosses my face when it happens.
Jerry – thank you for being you. And for everything you do in this world.