In my car on the way back and forth between Denver and Boulder the past few days, I listened to The Steve Ballmer Interview on the Acquired podcast by Ben Gilbert and David Rosenthal. If you aren’t a subscriber, it’s in the category of a “must-listen to podcast.” I’ve known Ben and David for many years from their time at PSL and Madrona, and they’ve created an outstanding new media property with Acquired.

While their two-part series on Microsoft (Microsoft Volume I and Microsoft Volume II) is excellent, The Steve Ballmer Interview is extraordinary.

While I doubt Steve ever thinks of me, I have enormous respect for him. I met him for the first time in the early 1990s on a trip to Microsoft when I was running my first company (Feld Technologies). Dwayne Walker had organized an event for the early group of Microsoft Solution Providers, and we were one of them. It was the first time I had been on the Microsoft campus, which was growing like crazy. Steve spoke at one of the events and I got to shake his hand. I was the President (we didn’t have a CEO) of this tiny little company in Boston, and I was in awe of him.

The next time I met him was after AmeriData acquired Feld Technologies. My company had become the consulting division (AmeriData Consulting), I was the CTO, and on the deal team. AmeriData was the largest Novell NetWare reseller in the world, and Microsoft was working hard to get us to be a significant Windows NT Server reseller. AmeriData and Microsoft held a day-long meeting that included approximately a dozen AmeriData leaders and an equal number of Microsoft leaders. I was part of the AmeriData delegation, and Steve was standing at the head of a very long table. As people went around the room introducing themselves, he stopped at me and said, “Is your dad Charlie Feld?” I responded with “He’s my uncle.” Steve, in his thunderous voice, said, “That guy is single-handedly keeping OS/2 alive!” My AmeriData colleagues were likely uncomfortable and regretted that I came. Steve then laughed and said, “Tell Charlie hello.”

In the mid-2000s, after the internet bubble had collapsed, Dan’l Lewin organized a group of VCs that included me to be part of a Microsoft VC Advisory board. We had quarterly meetings with different teams at Microsoft as they attempted to win back the hearts and minds of VCs and the developer community, who had turned against them aggressively during and after the internet bubble. We split our meetings between Redmond and the Microsoft office in the Bay Area.

These were fun meetings where, with Scott Maxwell, the two of us endlessly played the role of provocateur because neither of us needed anything from Microsoft, couldn’t restrain ourselves, and just had fun riffing off each other. Dan’l encouraged us with setups like, “Brad and Scott, please, no BS today, just tell us why we are going to get our clocks cleaned in Mobile by Apple now that the iPhone is out.” Or, “Please tell us what is wrong with Project Red Dog when compared to AWS.”

I recall Steve attending at least one of these, and Scott Guthrie serving as a proxy for Steve at another one. They were rambunctious and fun. Steve was trying to convince us of the Windows three-screens and the cloud strategy, and Maxwell and I pulled out our iPhones and said, “Nope – not gonna happen.” (The three-screens part didn’t, but the cloud part did.)

Even though Steve made a lot of mistakes, he was super clear about what his strategy was and how he was trying to get this huge company to shift and move and dodge and evolve and survive in what is one of the roughest markets ever for incumbents. I adored his energy, his willingness to debate and keep searching for answers, and his ability to engage deeply with people, even when they challenged every aspect of what he was doing. Oh, and his boisterous and self-deprecating personality.

You’ll feel the same energy and intellect from Steve in this episode, including deep discussions about things he got wrong. And, even though he has been extraordinarily successful, you can hear his humility come through in how he discusses his experiences—good and bad—with his incredible journey at Microsoft spanning over 34 years.

Tim Ferriss did one of his very long-form (150 minutes) podcast with me last week. I met Tim for the first time in 2007 and we’ve been friends since, although we’ve spent relatively little time together in person. Like many of my friends, I have a very comfortable remote relationship that has a lot of emotional intimacy in it. While many humans find this difficult, I never have and enjoy it a lot.

I think this comes through nicely in the podcast. It helps that Tim is particularly amazing at the long-form podcast interview. While the setup was around my new book, The Startup Community Way, which comes out tomorrow (please pre-order – authors love pre-orders), I don’t think we talked about the book at all until around hour two!

The following are the show notes. I hope you get a chance to listen to this. And, if you have any thoughts or feedback, drop me a note!

Tim – thanks for doing this. I’m honored to be part of your podcast cannon (#448!)

The phrase “contemporary mentors” popped into my head on loop number six of eight on my morning run. I’m training for a Covid marathon, which is 27 loops around my property.

My pace is tentative as I’m still gearing up after a long break due to a back injury, but I’m letting the miles and the time on my feet build on the weekends.

Running in circles for hours is different than running in the mountains in Aspen during the summer. But, I’m afraid of going to Aspen right now because of Covid, and I’m afraid of leaving my property and running on the roads or the trails near Boulder.

So, I’m embracing the circles. Amy likes it because she can keep an eye on me and let Cooper come out for the last couple of loops. While I think he could run with me forever, she worries about him when he goes for more than three loops, which is about six miles for him given all the back and forth he does.

I’ve decided that I’m going to approach the second half of 2020 differently than I approached the first half. This weekend, I turned off a bunch of inputs. I had several long conversations with Amy, right after I meditated, but before I did anything else, including one today where I acknowledged that the organizing principle I’ve been operating with for the last year isn’t working for me. I spent a lot of time outside, but without feeling tethered to anything. I allowed myself to feel what I was feeling, instead of trying to catch up or get on top of the stuff. I laughed at the few absurd things that crossed my path, rather than letting them aggravate me. I thought some more about what I wanted to spend my time on and what I was going to delete.

None of this is new for me – it’s a regular repeating cycle. Sometimes it’s part of my burnout loop or a boom-bust work cycle. Other times it’s a function of not knowing my limits and getting depressed. Once it was a function of a self-induced depressive episode because I stupidly took Ambien for two weeks on an international trip. And sometimes it’s just random.

A little more than a year ago, I came up with a new organizing principle for how I was going to address my work. I thought it was clever, was proud of myself for coming up with it, and tried it for a while. About a month ago I realized that it was a failure and that I wasn’t happy with it. While several aspect were working, several weren’t, but most importantly I realized that my frustration with it and my determination to try to make it work, even when it wasn’t, was making me unhappy.

So, about a month ago, I threw it away. I didn’t stop any of the activities I was doing, but I threw away the organizing principle.

This morning, I told Amy that I had thrown it away. It was the first time I was able to articulate this clearly. I don’t have a new organizing principle yet, but I knew the one I was using wasn’t working.

When my running loops increased, I realized I needed to listen to something while I’m running. Usually, I run “naked” (without headphones), especially when I’m in the mountains or on trails. But, after a few 0.95-mile loops, I want some stimuli other than “another loop.”

I decided to go through some Tim Ferriss podcasts and listen to some of my friends that he interviewed. I think the world of Tim and have learned a lot from him, even though we haven’t spent a lot of time together. And, whenever I listen to any of his podcasts, I learn at least one thing, and they often cause me to think about a few things.

In order, over the past few longer runs, I’ve listened to:

• Secretary Madeleine Albright — Optimism, the Future of the US, and 450-Pound Leg Presses (#437)
• Jerry Colonna — The Coach with the Spider Tattoo (#373)
• Ryan Holiday — How to Use Stoicism to Choose Alive Time Over Dead Time (#419)
• How Seth Godin Manages His Life — Rules, Principles, and Obsessions (#138)
• Jim Collins — A Rare Interview with a Reclusive Polymath (#361)

It was in the middle of Seth’s interview that the phrase “contemporary mentors” popped into my head.

I was searching in the background for a phrase different than “entrepreneurial heroes.” I started my first business in the 1980s and my entrepreneurs heroes include Bill Gates, Mitch Kapor, Steve Case, and Dan Bricklin.

But Seth, Jerry, Ryan, Tim, Madeleine, and Jim are in a different category. They are mentors of mine, in a long list of mentors. Some – like Jerry – are soulmates. Others, like Madeline and Jim, are people I know a little bit but respect enormously. And Ryan and Tim are contemporaries on a different vector entirely.

Aha – “contemporary mentors.” The ideal mentor-mentee relationship is when the mentor and mentee become peers and learn from each other. But peer mentorship has never become an easy category for me to explain as it implies an evolution from a mentor-mentee relationship. What if that’s not what happened.

Tim and Seth – thank you. As I listened to you today on my run, I learned from each of you, while having a close emotional connection from my own relationship with each of you. And from it came a new phrase for me: “contemporary mentors.”

I do a lot of random podcasts and especially like to be an early guest on new ones to help get them started.

001 – Brad Feld

The first five episodes are with me, David Cohen, Susan Conover, Amos Schwartzfarb, and Charlie O’Donnell.

Andrew Waine is the producer. He’s currently a senior at the University of Florida finishing his Bachelor’s degree in the Summer of 2020.

He reminds me of a young Harry Stebbings of the 20 Minute VC who reached out to me early (I was on Harry’s 65th episode in 2015), hustled, and did a fun interview with me where we cover the following topics.

• What is in the new edition of Venture Deals
• My time as an entrepreneur and entry into venture capital
• Advice from Jack Tankersley, an early mentor
• The differences between raising fund I vs. fund II at a VC Firm
• How fund sizes impact investing strategies
• How a startup can weather the storms of an economic downturn and the characteristics of the companies that survived the 2008 recession
• My opinion on USV founder Fred Wilson’s blog post about the importance of follow-on capital
• Why Foundry Group invests capital into other VC funds
• What startup accelerator Techstars looks for in its applicants
• Some resources and advice for a young person looking to gain knowledge about VC and Startups

You will even find out where I learned that “even pigs can fly in a hurricane” around minute six.

Amy and I driving to dinner with Ben Einstein and Grace Livingston a few months ago. Amy generally dislikes podcasts so she was annoyed with me as I fiddled with my iPhone and Carplay which kept opening my podcast app.

Ben said, “Have you listened to The Anthropocene Reviewed?”

I responded, “The what what?”

Amy said, “Put some music on.”

Ben tried again. “Put on The Anthropocene Reviewed Scratch ‘n’ Sniff Stickers and the Indianapolis 500.”

15 minutes later Amy said, “Not bad” and I was hooked.

Several of my favorites have been Notes App and Sports Rivalries, Hot Dog Eating Contest and Chemotherapy, Gray Aliens and Rock Paper Scissors, and Teddy Bears and Penalty Shootouts.

If you are looking for a new podcast, give The Anthropocene Reviewed a try.

When David and I started doing the #GiveFirst podcast, I was told by a long-time podcaster that it takes about 20 episodes to hit your stride. Since then, several other podcasters have told me that the number is actually closer to 100. Given that hurdle, David and I are 20% of the way there.

In Episode 22, we review the last dozen podcast guests including Josh Hix, Rajat Bhargava, Elizabeth Kraus, Jason Mendelson, Jannet Bannister, Heidi Roizen, Marc Nager & Dave Mayer, John China, Sherri Hammons, Rebecca Lovell, and Harry Stebbings.

I’m enjoying co-hosting the #GiveFirst podcast with David. I hope you are enjoying listening to it.

In 2010, David Cohen and I wrote a book titled Do More Faster. It was filled with stories and advice from founders, investors, and mentors from around the first two years of Techstars.

This was the first book I wrote. David and I learned the joy and pain of writing a book. We were lucky to get to work with Bill Falloon, who has been my long-time editor on all the books I’ve written. Bill guided us through the process and helped us understand what was required to put together a real book.

Last month we released Do More Faster, 2nd Edition. We’ve freshened it up with new content, some new stories, and updates on where everyone is from the first edition.

We just released an episode of the Give First podcast with some behind the scenes back and forth on the book. Enjoy the Give First Do More Faster podcast episode and go grab a copy of the new and improved 2nd Edition of Do More Faster.

Today’s Give First podcast features Harry Stebbings of the 20 Minute VC and a partner at Stride.vc on committing to building a network & giving first.

Harry is probably best known for his podcast, The Twenty Minute VC, the world’s largest media asset in venture capital, with over five million downloads per month. He’s talked with amazing VCs and entrepreneurs on over 2,800 shows.

When he was 13, Harry watched “The Social Network,” the movie about Facebook, and it inspired him to become an entrepreneur and investor. At 18, he set up the Twenty Minute VC podcast.

I was interviewed on Harry’s 65th episode in 2015. It was fun to travel back in time and listen to it. And, I love Harry’s Google Glass picture.

Harry is on episode 11 of the Give First podcast. We’ve made it to double digits which I’ve heard is a milestone for a lot of podcasts that stall out before that. Next step – triple digits. If you missed the last few along the way during my blogging vacation, they include John China (SVB), Sherri Hammons (The Nature Conservancy), and Rebecca Lovell (Create33).

I’m a huge fan of Elizabeth Kraus, Sue Heilbronner, and the work they do through MergeLane.

Recently Elizabeth started a platform for the next generation of venture capitalists called Fund81. It includes a podcast, which has both a public section for everyone and a private section for the Fund81 members.

Elizabeth recently interviewed me for Episode 13 where we talked about maintaining mental health in the fast-paced venture capital world while supporting portfolio companies, colleagues, friends, and family wrestling with mental health issues. The public section follows.

Elizabeth and Sue – thanks for everything you and the team at MergeLane do for entrepreneurs and now other VCs.

When I wrote the post Every Lie We Tell Incurs a Debt to the Truth I expected to get some feedback. I got more than I usually do (mostly by email vs. blog comments) and much of it was thoughtful.

One person pointed to the video I embedded, which I thought was great. It’s an extensive explanation of things in HBO’s Chernobyl that were either simply wrong or exaggerated. The video is entertaining as well as substantive, so it’s a good addition to the content from the show.

Separately, I listened to The Chernobyl Podcast on my drive up to Aspen about two weeks ago. If you watched the HBO Chernobyl docudrama, the accompanying podcast is a must listen. Peter Sagal (host of NPR’s “Wait Wait…Don’t Tell Me!) interviews Craig Mazin (Chernobyl Series Creator and Executive Producer.) Peter is an awesome host and he pulls out a ton of interesting, useful, and curious information from Craig.

Next up for me is reading Midnight in Chernobyl: The Untold Story of the World’s Greatest Nuclear Disaster which is near the top of my pile of infinite books to read (right after I finish Black Crouch’s Recursion.)

David Cohen and I just released Episode 4 of our Give First podcast.

We interviewed Mary Grove on the origins of Google for Startups & Startup Weekend among other things. Mary has been a long time friend and supporter of Techstars and is currently a partner at Rise of the Rest Seed Fund, the co-founder of Silicon North Stars, and on the Advisory Board for the Techstars Foundation.

David and I are starting to get better at the podcast thing. It’s a new medium for both of us so we are learning and iterating quickly on what makes a good podcast interview. Any feedback – good and bad – is welcome.

David Cohen and I are doing a podcast together called Give First. Readers of this blog likely know that this is the mantra of Techstars and the title of an upcoming book of mine that will be published in 2020.

While I’ve been interviewed for many podcasts, I’ve never hosted one before. David and I have been massive fans of Harry Stebbing’s 20 Minute VC so we’ve modeled Give First after it. Harry really hit his stride after about 100 episodes so my guess is it’ll take us a while to be in the same zone as he is. It’s good to have something to shoot for!

The first episode is an intro with an overview. We’ve got a steady stream of episodes coming that are already recorded, so subscribe to Give First and give us feedback.

While we aren’t LPs in Eniac Ventures, we are big fans of the team. So, it was my pleasure to be interviewed by Hadley Harris as part of their Seed to Scale Podcast.

The interview ended up being two episodes and, while listening to it in the car, I felt like it was one of the better recent interviews that I’ve done. Hadley and I talked for about an hour and then he edited the discussion down into two ten minute podcasts, so he pulled out the good stuff and left all the garbage on the cutting room floor.

Episode 1 includes advice I’d give to a much younger me and discusses why I think it is important to build long-term fund strategies with conviction and consistency.

Episode 2 covers what makes an excellent board member, the biggest reasons startups fail, and the three machines that must work together in order for a company to scale.

Enjoy!

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.

I’ve become a huge fan of Harry Stebbings, the intrepid entrepreneur turned VC whose age (20) matches the title of his podcast (The Twenty Minute VC.) Today, at SaaStr at 1:40pm in the Hypercritical section, Harry is interviewing me about – well – whatever he wants.

Harry has done hundreds of 20 minute VC interviews over the past few years. It’s a staple of mine on my podcast listening rotation so I’ve heard a bunch of them. It’s fun to watch Harry evolve as an interviewer as his knowledge of the industry has increased dramatically and his point of view about various VC-related things has become crisp and clear. And his hustle is relentless and has led to him also doing the SaaStr podcast and joining Atomico.

All five of the Foundry Group partners have been interviewed at this point. I think our interviews are a great way to get to know us quickly since we each tell our story, our strategy, and our approach in our own words and from different perspectives. Over the past few weeks I’ve probably talked to over 100 VCs between my trip to Australia, LA, and SF. When I find myself telling our story in response to being asked, I often wish I had a short cut to point people to.

This post is now the shortcut. I’ll use Harry’s original titles so you can see how his SEO prowess has evolved.

20 VC 065: FOUNDRY GROUP WEEK 1: BRAD FELD

20 VC 066: FOUNDRY GROUP WEEK 1: SETH LEVINE

20VC: THE FUNDAMENTALS TO CREATING A SUCCESSFUL VENTURE PARTNERSHIP & THE OPTIMAL INVESTMENT DECISION MAKING PROCESS WITH RYAN MCINTYRE, CO-FOUNDER @ FOUNDRY GROUP

20VC: HOW 50% OF VCS HURT ENTREPRENEURS, HOW TO BUILD A RELATIONSHIP OF TRUST WITH YOUR VC AND HOW ENTREPRENEURS CAN DETECT VC BS WITH JASON MENDELSON, CO-FOUNDER @ FOUNDRY GROUP

20VC: WHY MANY VCS FAIL TO RAISE, WHY LP COMPENSATION IS A MASSIVE PROBLEM & WHY FUND OF FUNDS WILL BECOME MORE PROMINENT WITH LINDEL EAKMAN, MANAGING DIRECTOR @ FOUNDRY GROUP

Yeah – I don’t love the capital letters either, but there you have it.

In case you are wondering about the tone of the 100 VCs I’ve talked to, I’d rate it as very high on the anxiety meter. Some of the tone is from the macro dynamics post election, but some seems deeper and more unsettled. I don’t know what it is, but I switched my Headspace meditation pack from Motivation (which I don’t need any help with) to Anxiety, just to be proactive.

Last month I had dinner at Pizzeria Locale in Boulder and did a long interview with Nick Chirls and Alex Lines of Notation Capital for their podcast. Dinner was about them and as they learned, if you trek out to Boulder, dinner is on me.

Their podcast series is called Origins and is unique among podcasts as they go deep into the formation history of venture funds, especially from an LP perspective. I was their ninth interviewee following some really great ones including Beezer Clarkson (Sapphire), Naval Ravikant (AngelList), Chris Douvos (VIA), Michael Kim (Cendana), and Judith Elsea (Weathergage).

They walked me through multiple origin stories, including how I started making angel investments (1994), the origin of Mobius / Softbank Venture Capital (1996-1997), the origin of Foundry Group (2007), and the creation of Foundry Group Next (2015-2016).

https://soundcloud.com/notation-capital/origins-episode-9-notation-capital-and-brad-feld-foundry-group

If you want to listen to all of the podcasts, subscribe to Origins on iTunes, Google Play, or SoundCloud.

One of the podcasts in my regular rotation is Turnpikers. Luke Beatty and Danny Newman – both long time friends – are doing an awesome job interviewing interesting people in the Boulder – Denver startup community.

If you don’t know the area, Turnpikers stands for U.S. Route 36 (known locally as “36” or sometimes “Highway 36”). But the locals call it the Boulder Turnpike. So, those of us who travel up and down 36 between Boulder and Denver are known – at least to Luke and Danny – as Turnpikers.

Luke and Danny interviewed me a few weeks ago in a studio at Postmodern Company in Denver. We hung out for an hour in a windowless room talking about whatever came to mind. I never listen to interviews I do before they are published – I like to listen to them after they are out in the world. This interview was one of my recent favorites.

The interview is Episode 18 of Turnpikers. You can listen to it here on the web. Or go to iTunes and download the entire Turnpikers podcast. iTunes gives me a little E for explicit – go figure. If you live in Boulder or Denver, be recursive and listen to it while driving on 36.

My partner Lindel Eakman just did a really fun interview with Harry Stebbings on Harry’s 20 Minute VC Podcast. You can listen to it here or subscribe to the 20 Minute VC on iTunes.

As a Saturday bonus, two of the other podcasts in my regular rotation are the Reboot Podcast and How I Built This. I listened to the VICE: Suroosh Alvi interview yesterday and it was fantastic.

The show notes for Harry’s interview with Lindel follow.

1.) How Lindel made his way into the weird and wonderful world of LPs and then Foundry? What is the origin story behind is first fund investment, Union Square Ventures?

2.) Question from Michael Kim @ Cendana: How is Lindel approaching portfolio construction for Foundry Next? What combination of GP portfolio & direct exposure diversifies the portfolio while retaining upside through individual deal performance?

3.) With the direct co-investment platform how does Lindel look to mitigate the negative signalling that can occur with opportunity funds? Does Lindel agree with Chris Douvos in stating this could lead to the ‘hybridisation of GP and LP’?

4.) Where do most prospective fund managers fail when pitching to LPs? What does Lindel look for in a risk strategy for a potential fund investment?

5.) What are the biggest problems with the LP community today? What would Lindel like to see change? What do the financial compensation plans look like for LPs?

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.

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.