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.

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.

It’s really hard to be a CEO. Becoming a great CEO takes a lot of time, work, focus, coaching, and introspection.

My very close friend Jerry Colonna is hosting his second CEO Bootcamp from April 2 – April 6. Several CEOs from the Foundry Group portfolio went last year and each had an amazing time. This year I’m going to be attending as a special guest and participating throughout the four day program.

I’ve learned an enormous about from Jerry over the past 20 years.  We first met in 1994 when I was a chairman of NetGenesis. Jerry had recently invested in a company called eShare, which ended up buying a product called net.Thread (one of the first, if not the first, threaded discussion group system – which was written in Perl) from NetGenesis. I joined the eShare board as part of the deal and a very deep friendship and working relationship ensued.

When Jerry told me about the first CEO Bootcamp a year ago I encouraged a number of CEOs in our portfolio to attend. Each one came back saying some version of “it changed my life”, which wasn’t really a surprise to me knowing Jerry but was a strong positive affirmation of the experience.

This year, when Jerry told me the dates for CEO Bootcamp and asked me to spread the word, I asked if I could come and participate. It’s in Colorado at an awesome place called Devil’s Thumb Ranch so I can drive to it and is a topic that’s front of mind for me given my relationship with the various CEOs in our portfolio.

I try hard to develop a deep personal relationship with the CEOs I work with. I’ve written in the past about Being Vulnerable and think it’s one of the most important qualities of a leader. As Jerry says so well in the overview of the requirements for attendees, “you may be tired, but you must be vulnerable, curious and courageous.” The full list of requirements follows:

• You’re the CEO of a tech start­up that has employees.
• This is the first time you have been a CEO within a company of this scale.
• You’ve logged immeasurable hours and have made tremendous sacrifices.
• You’ve had success with your company. You realize there is more to this game than “success.”
• You may be tired, but you must be vulnerable, curious and courageous.

I’m planning on participating in the entire event. The agenda is still being finalized, but the current plan is for me to do a joint talk with Jerry on Friday, fireside chats with Jerry on Friday and Saturday, and hikes after the main sessions.

I know two of Jerry’s three partners in this endeavor and think Sam Elmore and Ali Schultz are dynamite. To be clear, I’m volunteering my time and participating – this is Jerry, Sam, Ali, and Michael’s gig so I’m going to do whatever they want me to – or not to – do.

Registration is open until 2/9/14 at midnight MST. 20 CEOs will be accepted. I hope to see you there.

Jerry Colonna spent a few hours with me and Amy on Saturday at our house. Jerry is one of our closest friends on this planet so any time we get time with him is a treasure for us. It was a cold-ish, snowy, gloomy Colorado early winter day. Amy and I were pretty off-balance due to my blood clot so it was especially nice to be with him as he always helps rebalance us.

We talked some about his new company Reboot. I’m a huge supporter of Jerry’s work – recommending many of the CEOs we work with to him, or his associates, for coaching. I attended a recent CEO Bootcamp as a special guest and it was amazing – I recommend it to every CEO.

Jerry mentioned that the recent Reboot podcasts were doing great and really fun. I noticed this morning that the podcast he did with Rand Fishkin, another close friend, titled #7 Depression and Entrepreneurship – With Jerry Colonna and Rand Fishkin, came out today. So I read the transcript (I can read a lot faster than I can list) and thought it was dynamite.

As usual, Jerry goes deep and intimate – very quickly. So does Rand – total, extreme, full transparency. Enjoy!

Of all the podcast interviews I’ve done over the years, I think the one I recently did with Jerry Colonna on his Reboot podcast series is my favorite.

In the podcast show notes, Jerry links to a fun post by Fred Wilson titled Sixteen Years Ago (which is now 19 years ago…) We’ve known each other for a very long time and I treasure Jerry as one of my best friends on this planet.

Enjoy the week. Hopefully this will provide some thoughts as well as some fuel for you. And, if you aren’t a regular listener to the Reboot podcast, I encourage you to subscribe to it as a source of deep insights from Jerry every few weeks. There are 25 episodes so far since Jerry started it with his gang in September 2014 – I’ve listened to and benefited from every one of them.

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.

• #GivingThanks: Jerry Colonna and Naropa University
• The CEO Whisperer
• Love and Venture Capital

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.

I saw a great job title this morning when I was looking someone up on LinkedIn. It was “CTO Whisperer.”

As I’m getting deeper into meditation. I hear the word “teacher” a lot. I’d never thought much about it before, but it’s used in a similar way to how we use the word “mentor” at Techstars. When we started to use the word mentor in 2007, it required defining. Now mentor is getting overused by the broad entrepreneurial landscape. I have no idea whether teacher is overused as well, but the parallel got me thinking about the idea of a CEO Whisperer.

I’ve always been fascinated by the idea of The Horse Whisperer or a Dog Whisperer. A person who has a special, magic skill that certain animals respond to. A unique ability to calm and teach. A style about them that is unique, loving, and kind, even in difficult circumstances.

As I was mulling this over, my friend Jerry Colonna popped into my mind. While Jerry is referred to as a CEO coach, he most certainly is a CEO Whisperer. And for those who don’t know Jerry’s past, he was an extremely successful venture capitalist, founding Flatiron Partners with Fred Wilson in the mid-1990s before retiring from venture capital in the early 2000’s.

I count Jerry as a very close friend. As a mentor. As a teacher. And, with all great mentor / teacher relationships, we learn from each other. Which led me back to the idea of a CEO Whisperer.

In the 1990’s, Jerry and I worked together on several investments and were on a few boards together. Our styles were very complementary – we both had a soft touch and were supportive of the CEO, but had different things we could help with. I know that my involvement on these boards deeply shaped my role and approach as a board member and investor, as I thought Jerry was the best board member I’d ever worked with at that point in time.

I’ve met – and worked with – a few other people who I’d consider CEO Whisperers, but none compare to Jerry. And when I think about how I want to be viewed by the CEOs I work with, the idea of mentor and teacher immediately comes to the forefront of my mind.

The world of entrepreneurship needs more CEO Whisperers. Thanks Jerry for leading the way. On multiple fronts.

As an unrepentant Ben and Jerry’s worshiper (thanks to my dad for my ice cream addiction). I’m always sad when my favorite flavor disappears.  I like everything chocolate – the stranger the better – and they’ve had some strange ones (Makin’ Whoopie Pie or Reverse Chocolate Chunk anyone?)

These flavors got sent to the Ben and Jerry Cemootary.  I guess enough folks like me believe in ice cream resurrection so you can now vote to have them come back to life.  Vote now.

And – in a hat tip to Seth Godin’s Cow – it’s Purple!

On my run this morning (yay – I’m running again) I listened to a wonderful podcast between Jerry Colonna and Bijan Sabet called Investors are Human Too – with Bijan Sabet.

If you follow me, you know that I’m incredibly close friends with Jerry (he’s one of the people on this planet that I comfortably say that I love). I’m also a huge fan of his company Reboot.io. If you want a taste of what they do, listen to a bunch of the Reboot podcasts (I’ve listened to them all and the least interesting one is still excellent.)

I’m also a big fan of Bijan. We’ve had a number of great conversations over the years. While we haven’t sat on a board together, I have deep respect for how he functions as a VC – and as a human.

At Foundry Group, we’ve done a number of investments with Bijan’s firm Spark Capital, including AdMeld (sold – very successful investment), Trigget (sold, but not a successful investment), and most recently Sourcepoint. We’ve also got another one in the works together that should close by the end of August.

Unlike so many podcasts with VCs where you get lots of personal history followed by advice, prognostications, bloviating, and predications, this one was all about being human. Bijan and Jerry explored things in the context of the relationship between a founder and a VC. They covered things generally, had some great examples (including Jerry and Mainspring, which was a blast from the past for me), and then Bijan went deep on his own journey to figure this out over the past ten years.

My favorite line came near then end when Bijan talked about encountering VCs who hide behind the phrase “fiduciary responsibility” to justify their actions, when in fact they should just say:

“I have a fiduciary responsibility to treat you like shit.”

Even though I was huffing and puffing on my run, I laughed out loud.

If you are a podcast listener, spend 45 minutes of your life on this. It’s worth it. Bijan and Jerry – thanks for the conversation and for brightening up my run.

Several years ago, Alex Iskold wrote a great overview of What It Is Like To Sell Your First Company. I thought it was a great description and encourage every entrepreneur who has never been through the sale of a company to read it.

Rereading Alex’s post inspired me to write my first person account of selling my first company. I’m sure I’ll get stuff wrong since it was over 21 years ago (I was 27.) But I’ll try to capture the good stuff that I can remember, especially since I know I had absolutely no idea what I was doing and could only rely on verbal conversations with other entrepreneurs I knew to help me figure things out since there was no web, no real books to read, and entrepreneurship still wasn’t a word being used regularly. When I reflect on it, independent of the modest economics, the experience changed the trajectory of my life in a very powerful and positive way, even though it was an extremely confusing time for me.

It 1993, I sold my first company, Feld Technologies, to a company called Sage Alerting Systems (which, after several name changes, became AmeriData Technologies.) It was a six month journey for me and my partner Dave Jilk which was at some points exciting, often stressful, and occasionally extremely confusing. It didn’t help that I was in the middle of a deep two year depression which I kept hidden from everyone in the world except Dave, Amy (who I was living with at the time before we got married), my parents, Eric von Hippel (my PhD advisor), and my therapist.

It started, like many things, completely randomly. When we installed a network for a client, we used a company called Allcom (run by two brothers – Jim Galvin and Mike Galvin.) They were great guys, easy to work with, and we sent some business back and forth. This was before WiFi networks so the cabling jobs, especially in downtown Boston, were never trivial, especially in the older buildings. One day, Jim called me and said something like, “Brad – we’ve been acquired and the chairman of the company wants to get together with you for lunch.” At the time I had no real idea what this meant, but figured, what the hell, I’ve got to eat.

I had lunch with Jim and Len Fassler at a restaurant near our office by South Station in downtown Boston. I can’t remember the name but it was a funky place I went to all the time. Jim and Len showed up a few minutes after me and we sat at a table. Len looked like a cross between a powerful New Yorker and Yoda – sharply dressed in his jacket and tie but short and with a friendly face weathered from experience. I was nervous. Very nervous.

We ordered and chatted for a little while. Len asked me softball questions about myself, Feld Technologies, what we did, how we did it, how many people we had, and what our backgrounds were. I can’t remember if Dave was there, but I don’t think he was. In the middle of lunch, Len said, “Jim speaks very highly of you. We’d like to buy your company.”

I was in the middle of a bowl of soup. I remember having to use all my self control so it didn’t get spit out all over the table. I wasn’t expecting this in any way, shape, or form.

We kept talking. I asked a bunch of naive questions, in the form of “What do you mean?” I remember feeling completely clueless and out of my depth. Len explained Sage Alerting Systems’ strategy, talked about how as a public company they were doing a rollup and growing quickly through acquisition, and said they were looking for a lot of small companies in the IT services business. They’d acquired a few companies so far and had LOIs out to a few more. They were really happy with Jim, Mike, and Allcom and wanted to buy more companies in Boston. I learned that they weren’t in New York, but were in Stamford, Connecticut, which I’d never been to.

Lunch ended and Len told me to think about it and call him if we were interested. I don’t really remember the next few conversations with Dave and my Dad (who was an advisory and co-owner) but I do remember a lot of vacillation on my part. Eventually Dave and I decided to go to Stamford to visit Len and his partner Jerry Poch.

We made the drive down on what I remember was a brilliantly sunny day. We didn’t really know what to expect, but when we got to Sage’s office, it was a mad-house of phone calls, people moving from room to room with stacks of paper, and rapid discussions. It was a small but lovely office overlooking the Stamford Canal (I think the address was 700 Canal Street). Len’s assistant Mildred, who I ended up getting to know pretty well over the years, greeted us and put us in the big conference room, which wasn’t very big. A new guy I hadn’t heard of yet named Jerry LeBow came in. Jerry, along with Len and Jerry Poch became a very close friend over time, but in this meeting we just sat and listened to him tell us about Sage Alerting Systems (which he was President of), the emergency warning system (which he knew more about than anyone else on the planet), and the technology he was working on. It was a one-way conversation and it became clear at some point that Lebow was filling up airtime while we were waiting for Len, but that was ok because it was interesting and we were nervous.

Eventually Len came in, apologized for keeping us waiting, and sat down to business. He’d asked us to bring our financing statements so he could look at them to come up with an offer. We gave them to him (no NDA required – we didn’t even know, or care, what an NDA was) and he started going through them. We always had very clean financials because we took it seriously so he quickly sized up our income statement and balance sheet. He asked us a few confirmatory questions, including how much salary we were each getting paid, separate from any distributions from the business, which was $100,000 / year each.

He turned over a piece of paper and scribbled an offer on it. It was 40,000 shares of Sage stock, options for another 40,000 shares of Sage stock, the cash and working capital on the balance sheet (which was about $250,000), salaries of 100k for year 1, 110k for year 2, and 120k for year 3, and 10% of the profits of our group going forward. I’m 99% sure that was the offer, although Dave might remember something different, so it’ll be interesting to see if he weighs in here and corrects us.

Len explained that was their formula for doing deals – 2x multiple of Net Income + balance sheet cash + a three year employment deal. At the time, Sage stock was around $6 / share so it was like a $500,000 offer for the business, half with cash that we’d already earned but had tied up in the business, but upside in the stock and the options. Len made the point that the stock and the options had a lot of upside.

By this point I think Len could have offered us $1 for the business and we would have taken it. We were both totally burned out running the company, had never really thought about the business, were excited about the idea of being able to sell it, and entranced by what was going on around us. Remember that I was very depressed (although I used up all my energy not showing it) and I’m sure Dave was totally worn out from dealing with me. I knew I liked Len from lunch and fell in love with him in that meeting, a love which endures to this day.

Len didn’t propose this as a “bid/ask” type offer – it was a very soft, straightforward “take it or leave it” offer – and it was clear that they were doing lots and lots of transactions and if we weren’t interested, that was fine and they’d quickly move on.

Suddenly Jerry Poch came in the room. In contrast to Len’s calm fatherly approach, Jerry was awesomely full of fire, power, and energy. He was loud, aggressive, and enthusiastic. He knew about us, even though we hadn’t met yet, told us how excited he was to be talking to us, and mentioned how the Galvin’s thought we were great and hoped we could do a deal together. And, before I knew it, he was gone, off to the next thing.

I remember meekly telling Len to send us an offer. I remember shaking hands and vaguely felt like we’d just agreed to a deal. We said our goodbyes, Dave and I left the office, and went to our car for the three hour drive back to Boston.

to be continued…