Tag: jerry colonna

Sep 12 2018

Acknowledging The Value of Coaching and Therapy for Founders

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 foundersIn 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.

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Feb 26 2018

Interviewing Jerry Colonna About Heart – His!

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.

  • “What I’m trying to do right now is pull myself into the present and be really real.” – Jerry Colonna
  • “I have always given a shit about people.” – Jerry Colonna
  • “Things are fucked up all the time like every day, continually. You can either just react to it, or you can deal with it.” – Brad Feld
  • “I think that there are two things that I would get excited about as an investor. People and product.” – Jerry Colonna
  • “Better humans make better leaders.” – Jerry Colonna
  • “I don’t want to spend minutes with people who I don’t feel are good humans.” – Brad Feld
  • “Good people do shitty things all the time.” – Jerry Colonna
  • “If you’ve got that inquiry process and you remain curious about human beings, you can, with compassion, understand and therefore protect yourself from the bad things that even good people do.” – Jerry Colonna
  • “Men at 40 learn to close softly doors to rooms they will not be going back to.” – Jerry Colonna
  • “This idea that people are fundamentally willing to work on themselves and that they’re there for each other especially when there’s a struggle.” – Brad Feld
  • “When I’m dust and dried up, and I’m dead and whatever, please just keep paying it forward.” – Jerry Colonna

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.

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Apr 26 2017

The Best Time To Invest In Something Is …

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.

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Mar 3 2017

The Magic of Dealing With Your Demons

Jessi Hempel from Backchannel just wrote an amazing profile piece on my close friend Jerry Colonna. It’s titled This Man Makes Founders CryMedium estimates that it’s an 18 minute read and I assert that it’s worth every minute.

Jerry Contemplating Something

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.

  • “Jerry?” he responds. “That guy saved my life.” – Bart Lorang, FullContact CEO
  • “There was this moment where you admitted to each other that you were working with him. It’s not an official thing, but there is this almost secret society of people who’ve been coached by Jerry.” – Chad Dickerson, Etsy CEO
  • “Campbell had a testosterone-infused Silicon Valley kind of model. Jerry’s model is more Buddhism and less football.” – Fred Wilson, USV partner
  • “There are a lot of people you can go to who will teach you to be a better manager. Jerry understands the psychology of leadership.” – Alexander Ljung, Soundcloud CEO 
  • “Until we make the unconscious conscious, we will be dictated by it and call it fate.” – Jerry quoting Jung
  • “The Reboot team possesses an otherworldly talent for coaxing authenticity and truth out of people. They can even coax truths out of people who, like myself, have been lying to themselves for years.” – Jacob Chapman Gelt VC partner
  • “Life sucks and it’s okay. Life is great, and it’s okay. Life goes up and it’s okay; life goes down and it’s okay. If we can instill a sense of resilience in people, we mitigate suffering.” – Jerry

Go read the entire article on Jerry. And, if you want more, go listen to the Reboot podcast.

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Jan 24 2017

The Second Reboot VC Bootcamp

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.

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Jan 23 2017

Joining the Defy Ventures Board

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.

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Nov 24 2016

#GivingThanks: Jerry Colonna and Naropa University

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.

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Oct 23 2016

We Were Right – Just a Decade Early

This is a line my friend Jerry Colonna uses when something like the AT&T – Time Warner deal occurs. As time passes, the line has shifted to “We were right – just fifteen years early.”

Jerry was Fred Wilson‘s partner at Flatiron Partners. We were all investing in Internet-related stuff at the end of the 1990s. Jerry and Fred had one of the most successful VC funds during this time period until the Internet bubble burst and blew us all up for a while. We made plenty of investments together and I sat on a number of boards with Jerry – we had some big winners and a handful of craters in the ground.

At the peak, AOL bought Time Warner for $162 billion. We only know that was the peak in hindsight – at the time it looked like it validated a lot of what we were doing by investing in the Internet.

“This merger will launch the next Internet revolution,” said Steve Case, America Online’s chairman and chief executive, told a news conference Monday. “We’re still just scratching the surface.”

The market responded according to plan.

“Analysts expect competing Internet and entertainment companies to seek similar deals in hopes of keeping pace with AOL and Time Warner, and some of those stocks also got a lift Monday. Disney jumped $4.81 1/4 to $35.93 3/4 and News Corp. rose $7.31 1/4 to 45.06 1/4 on the NYSE. Lycos leaped $9 to $79.75 and Yahoo! climbed $28.81 1/4 to $436.06 1/4 on the Nasdaq Stock Market.”

Yup – you saw that correctly, Yahoo was at $436 / share. I think it split 2:1 twice, which would have made it priced at $109 / share. It’s currently at $42 / share so if I got the splits right, after its collapse in 2001 to a low of around $5 / share it took it 15 years to claw its way back to $42 / share (a 10x from the low, 40% of its high at the peak.)

Ponder Gartner’s Hype Cycle for a moment. You can apply this to pretty much anything in tech.

Gartner Hype Cycle

2000 was the Peak of Inflated Expectations. 2002 was the Trough of Disillusionment.

Now, choose any new and exciting technology now. Apply Gartner’s Hype Cycle to it. Ponder where you end up.

Steve Case wrote a book earlier this year called The Third Wave: An Entrepreneur’s Vision of the Future. In addition to looking forward to the future, Steve uses his lessons from the past to explore how things play out. It spans the time frame from 1985 – 2015 which you can just lay down on the Gartner Hype Cycle.

  • 1985 – 1994 was the initial entrepreneurial Grind
  • 1995 – 2000 was the climb up to the Peak
  • 2001 – 2002 was the collapse to the Trough
  • 2003 – 2012 was the climb to Enlightenment
  • 2013 forward has been the plateau of Productivity

In the context of this, the AT&T – Time Warner deal seems extremely well timed and relevant. Now it’s all about execution.

Consider any of Apple / Google / GM / Ford buying Tesla. Where does that fall on Gartner’s Curve? How about the auto industry. Or drones. Or what people are currently calling AI. Or – well – keep going.

One of the biggest challenges in tech is not being right. It’s being ten or fifteen years too early.

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Aug 11 2016

Love and Venture Capital

If you’ve missed me, it’s because I spent a week in Australia. Ten days ago, after being there for a few days, I came down with salmonella poisoning. I’m finally starting to feel normal again although I’m still exhausted. This has easily been the sickest I’ve ever been.

While I was gone, the gang at Reboot put up the Reboot Podcast #45 – What’s Love Got to Do with It?- with Fred Wilson and Brad Feld which was a delightful conversation between me, Fred, and Jerry Colonna.

The three of us have a 20+ year history that gives me joy every time I think about it.

I first met Fred in the suburbs of Boston at Yoyodyne in 1996. It was also the first time I met Seth Godin. I had just started working with Softbank and had been commanded to go to Yoyodyne and do “due diligence” by Charley Lax. I had no idea what Softbank or Charley wanted in the way of due diligence, so I went, hung out with Fred and Seth, and wrote Charley an email after saying “Looks great – Seth is awesome” or something like that. Softbank (and Fred – via his new firm Flatiron Partners, which was partially funded by Softbank) invested.

I first met Jerry in a conference room at NetGenesis in Cambridge. I was chairman and we has three product lines at that point: NetForm (an HTML form filler that was getting its but kicked by Allaire), NetThread (which was super cool but getting its butt kicked by something – maybe again Allaire), and NetAnalysis, which was the first weblog analysis tool and became the focus of the company. We sold NetForm to a company called Virtuflex (which went on to become Channelwave, which I became an investor in) and NetThread to eShare. Jerry, again through Flatiron (he and Fred had become partners), was an investor in eShare. I joined the eShare board as an outside director. eThread was acquired by Melita International in 1999 after a crazy ride that included a midnight negotiating session on the 173rd floor of some building in midtown Manhattan to try to merge with iChat. I remember walking about at around 2am with Jerry, completely wasted and frustrated. Welcome to 1999.

Over the last 20 years, the three of us have worked on lots of things in different configurations, but I’d put the deep friendship we’ve developed ahead of all of our business deals. We’ve won and lost together, had great moments as well as deep disappointments. But throughout, we’ve stayed best friends.

I enjoyed making the podcast, I hope you enjoy listening to it.

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Apr 25 2016

Reactions To The First Reboot VC Bootcamp

We had the first Reboot VC Bootcamp several weeks ago in Boulder. Based on the feedback and the experience, we’ve already decided to have another one, probably early in 2017.

Three of the participants – Steve Schlafman, Rob Go, and Josh Guttman – wrote posts about the bootcamp. Since the content was confidential, each of them is careful about what they say and does a good job personalizing the experience.

In A bunch of VCs went on a retreat. Here’s what happened Steve lists 16 things he took back with him to New York and his daily life from the bootcamp. To get a feel for them (and hopefully inspire you to go read the whole post), here are the first three:

  • When your inner and outer self aren’t in sync, it creates personal dissonance that results in being afraid, feeling unsafe, etc..
  • If you ask a founder how you can help, it means you haven’t been listening close enough. Be fully present.
  • Being a great board member or investor isn’t about having all the answers and fixing things. Don’t underestimate the power of listening and supporting.

Rob reflected, in his post Reboot, about the Parker Palmer notion of the shadow. 

“The idea is that one’s “shadow” is a deep rooted thing (not necessarily good, not necessarily bad) that exists in one’s psyche that drives your choices, behaviors, or emotions. The shadow is often linked to early, memorable childhood experiences, and is reflected in multiple arenas of life over and over again. The challenge occurs when one is unaware of these influences, and as a result, it drives him/her to make decisions or react to circumstances in a less than ideal way. Often, we can go years not really understanding how major decisions have been guided by hidden motivations, and that can get in the way of being the best leader, friend, or team member one can be.”

Josh wrapped the summaries up in his post Keeping it Real with an overview of the structure we used for the bootcamp

Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership + Greater Resiliency

followed by a good discussion around imposter syndrome, which came up a few different times and manifests itself in many different ways in our daily life, especially around entrepreneurship and investing.

It was deeply enjoyable to host this event at my house and spent a few days at a very emotionally intimate level with some VCs I know and have worked with and others that I met for the first time. I was a player-coach for the weekend – participating instead of facilitating, but also co-hosting with Jerry. I was concerned that this would be a challenge, but in hindsight it felt very natural to me. And, during a session where I became Jerry’s focus, I realized something profound that I had never put together before about my relationship with power.

To everyone who participated – thank you for being brave and taking the risk to engage at the level that a Reboot bootcamp demands.

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