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.

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.

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.

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.

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.

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.

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.

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.