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.
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).
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.
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.
I don’t listen to that many podcasts, but I like ones that are a short (< 45 minute) interview format. I can listen to one of these on a run or a drive to/from my office.
Until recently, the only one I was listening to regularly was the Reboot.io podcast. Jerry Colonna, the co-founder of Reboot.io is a dear friend and his interviews are often magical.
A few months ago I noticed The Twenty Minute VC by Harry Stebbings. I can’t remember which one was the first one I listened to, but I thought his style and interview approach was great. It was fast, started with an origin story, but quickly moved on to the present and then ended with a set of short questions.
Jon Staenberg, a long-time friend from Seattle who did an interview with Harry on episode 034, dropped me the following email at the end of April:
He seems like a good guy, want to be part of his podcast?
Ever in seattle?
I told Jon I’d be game. Harry responded immediately and we did a podcast together six weeks ago. I’d been listening regularly since Jon introduced us and heard several great podcasts, including mentions of me in 055 with Jonathon Triest and 059 with Arteen Arabshahi.
Last week Harry releases two episodes 065 with me and 066 with my partner Seth Levine. I had fun doing mine but absolutely loved listening to the one with Seth, especially around his version of the Foundry Group origin story.
Harry promises to interview our other two partners – Ryan McIntyre and Jason Mendelson – so he’ll ultimately have a triangulation (or maybe a trilateration) of our origin story.
In the mean time, enjoy the interviews with me and with Seth if you are looking for a podcast to listen to.
Jonathon Triest and Brett deMarrais of Ludlow Ventures are doing a fun video podcast series called Carpool.VC. As Jonathan and Brett drive to work, they do a podcast interview. It’s hilarious, fun, and informative.
I did it early (6am California Time) on Tuesday. In it, you’ll learn my spirit animal, doppelganger, how Jonathon and I met (I’m now an investor in Ludlow Ventures), and a bunch of other random things. I also agreed to sponsor the episode for $1.70.
Last week I participated in a podcast hosted by A16Z titled How Innovation Ecosystems Grow Around the Globe.
I got to talk with AnnaLee Saxenian, the Dean of the UC Berkeley School of Innovation. Her book, Regional Advantage, had a huge impact from on my thinking around Startup Communities. From a 2010 blog post of mine about a bunch of books that I had read on a week off the grid.
Regional Advantage: A+: I’ve read bits of Annalee Saxenian’s seminal book about the differences between the evolution of Silicon Valley and Route 128, spent a tiny bit of time with Annalee at a Silicon Flatiron event, and have thought hard about this, but I had actually never read her book. It’s awesome – anyone that cares about how entrepreneurial communities work must read this.
The other guest was Chris Schroeder who recently wrote a book titled Startup Rising: The Entrepreneurial Revolution Remaking the Middle East. I’m definitely going to spend more time with Chris in the future – he’s been spending a lot of time in the Middle East exploring entrepreneurship and has deep current experience and ideas that I’m interested in.
If you are interested in startup communities, I hope you will listen to this podcast. It’s one of the better ones I’ve done around the topic.