Tag: reboot

Sep 12 2018

Acknowledging The Value of Coaching and Therapy for Founders

I’ve long written about the stigma around entrepreneurship and depression / other “mental health-related issues.” I was delighted to see two articles in the last day about others addressing this.

First, Felicis Ventures is committing 1% on top of every check the firm writes in non-dilutive capital earmarked for “founder development” in coaching and mental health. I love the way Aydin Senkut has characterized what they are doing and why they are doing it.

“Felicis’ bet is that by making such resources available and publicly known, founders won’t feel too proud, or too much pressure to seem successful, to address personal and team issues. Tactical marketing help can only go so far, Senkut says, when founders aren’t telling their investors that they’re unable to sleep from anxiety, or not speaking to their cofounders.”

Next, Mahendra Ramsinghani has a long article in Techcrunch titled Investors are waking up to the emotional struggle of startup foundersIn it, he references a bunch of stuff, including work that Jerry Colonna and the team at Reboot have been doing around this issue. He also points to the survey he is doing for his new book titled Depression: A Founders Companion.

If any of this resonates with you as a founder, (a) go complete Mahendra’s survey, (b) connect with Reboot, or (c) send me an email to connect you with Mahendra or Reboot.

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Feb 27 2018

Book: A Second Chance

Cat Hoke’s book A Second Chance: For You, For Me, And For The Rest Of Us is out.

I wrote a long post about it in October when I read a draft of it. Cat is remarkable and she lucked out by partnering with the amazing Seth Godin on this book (Seth is the publisher).

I’m sending a copy to every CEO in our portfolio. We’ve got a pretty regular Foundry Group book club thing going at this point, as I know Rajat Bhargava and Will Herman’s book The Startup Playbook is also going out to a bunch of the CEOs. And each of my partners is getting a copy of Lee McIntyre’s Post-Truth this week.

I read a lot and encourage everyone around me to join in on the good stuff. Cat’s book is definitely good stuff. She mixes her own life journey with the mission of Defy Ventures along with the impact that Defy has had on so many people – both “entrepreneurs-in-training” and the volunteers who work with the EITs.

I’ve talked about Defy Ventures a lot on this blog and Amy and I have become significant supporters through both The Anchor Point Foundation and my volunteer engagement. I’m particularly proud, however, of my partner Jason and his wife Jenn who have picked up the mantle as co-chairs of Defy Ventures Colorado and launched the Colorado program. I was in prison with them, 50 volunteers, 50 EITs, ten people from the Defy team (including Cat), and Governor Hickenlooper two weeks ago.

All of this has been inspired, and led, by Cat. I didn’t know much about the US prison system prior to meeting Cat several years ago. My own journey with this has been incredibly powerful. Being able to experience it with other entrepreneurs and investors, including Jason and Jenn, a number of the Techstars team, and many others who I know has been wonderful.

If you want a pre-book taste, the Reboot podcast that I did with Jerry Colonna and Cat is a good start.

But, do yourself a favor. Buy Cat’s book A Second Chance. Read it, let it into your life, and ponder what a second chance really means.

P.S. I have several people in my life who I need to give a second chance to. I’m not ready yet, but I hope I will be at some point. And yes, the book will help you go deep on what this means for you.

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Feb 26 2018

Interviewing Jerry Colonna About Heart – His!

If you are a regular listener of the Reboot Podcast, you’ve heard Jerry Colonna masterfully interview many people. And – if you aren’t a regular listener, go sign up and give it a try.

In Episode 78: When Did You Start to Listen to Your Heart, I turned the tables on Jerry and interviewed him. We’ve been close friends for 22 years and I felt like it was time someone interviewed him on his podcast. I suggested it to him and his team, who either rolled their eyes or jumped for joy. Either way, it is now up.

I listened to the final version during my run yesterday. I smiled a lot, snickered a little, and grimaced a few times. If you want a taste to entice you to listen, here are a few of the quotes from the show highlights that jumped out at me.

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

It’s all Jerry for an hour with a little bit of me nudging the discussion along. None of it is scripted. We didn’t discuss anything in advance. Just two guys, who have known each other, worked together, and have had a deep emotional intimacy together – for 22 years – talking about some things that come to mind about what they think matter.

If you are a reader instead of a podcast listener, the transcript for Reboot Podcast 78: When Did You Start to Listen to Your Heart is also available.

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Dec 26 2017

A Cold Reboot

I’m on day 8 of a cold, which in retrospect has been possibly the harshest cold I’ve ever had. I felt worse when I had salmonella poisoning in Adelaide in 2016 and I remember a childhood flu over the holidays that had me throwing up for days. But, on Friday, when I had some existential dread, I realized I was really sick and crawled back in bed for the rest of the day.

I woke up this morning still sick but feeling on the mend. I’ve been at home for a week and haven’t been doing much other than sleeping, reading, responding to email, eating mac and cheese, and sleeping some more. I’ve been a sub-optimal companion for Amy, but Brooks and Cooper have filled in pretty well for me.

I’m glad the world is taking a break for the holidays. 2017 was an intense year in many dimensions. Our society changed in ways that feel extremely uncomfortable to me, but I’ve tried to process it with a long view. Long-simmering conflicts that were just under the surface explosively broke through and forced us to confront them and our collective behavior, and reactions, to them. I’ve continued to do what felt important and right to me while listening and learning. I worked hard to eliminate the noise and concentrate on the signal. To do this, I withdrew on several dimensions, especially via social media and online channels, which diminished my experience, but allowed me time and space to think.

I’ve been metabolizing my emotions at a new level. I’ve always been able to handle a huge amount of stress and anxiety, and part of my role has been to absorb the stress in the system, stay calm, and help the people around me work through whatever we are confronting. I’ve learned that when this gets to a certain level in me, it can trigger a depressive episode, so I’ve been working on understanding my limits better and how to address them more effectively. The broader cultural challenges of 2017 have just piled onto this, so I had to learn a new set of skills around this. If anyone is curious, the magic gateways for me have been meditation and therapy.

This cold forced some downtime on me. As I’m recovering, I’m going to savor the rest of the week and prepare for 2018. It feels like a cold reboot is in order.

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Jan 24 2017

The Second Reboot VC Bootcamp

On Saturday night I got on a plane and flew to the other side of the planet, where I am now. I’m in Melbourne, finishing my coffee, getting ready for one last meeting here before I fly with David Cohen to Adelaide for the day.

When I left, I had the voices and energy of 25 people in my head. Last Thursday evening was the beginning of the second Reboot VC Bootcamp at my house just outside Boulder.

Amy and I have a second house on our land, which we refer to as “the Carriage House” and the Reboot gang calls “Chez Feld.” The first floor is an event center that we use for non-profit events. The second floor was going to be a man cave, but my idea of a man cave is carrying my laptop around the house wherever Amy goes and sitting down next to her. The idea of hiding out from her a separate place has never made any sense to me so we turned the second floor into a retreat center which friends and companies in our portfolio are starting to discover and use, especially since it’s a lot less expensive (free) than renting a hotel conference room for the day – and a lot more pleasant.

About 20 VCs from around the world showed up for an intense four day experience lead by Jerry Colonna and his Reboot team. The website is understated about the experience.

“Over this long weekend with Jerry, Brad Feld and Team Reboot, we’ll work to uncover your authentic leadership style and teach practical skills for managing the array of feelings that can be triggered–all in the name of helping you become the best investor/board member/supporter you can be.”

To really understand it, read the following four posts from attendees of the second bootcamp.

I was a little sad to leave Saturday and not be part of everything, but reading each of these posts this morning made me very happy. It’s not just that “VCs are people too”, but that the 20 people who showed up in Boulder for four days opened themselves up completely as they each went down their own path of radical self-inquiry. Jerry and the Reboot team continue to amaze me (and many others) in their magical abilities around personal exploration and growth in a professional context (well – and a personal context.)

For everyone who showed up – thank you for coming and letting me be a part of it. As I sit here on the other side of the world with my soul gradually catching up with me from the jetlag, it’s powerful to ponder that we are all just bags of chemicals.

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Jan 23 2017

Joining the Defy Ventures Board

I recently joined the Defy Ventures board. If you aren’t familiar with Defy Ventures, here’s a post that I wrote after my first prison trip with them at the end of last year.

Early this morning, on my run in Melbourne as I tried to shrug off jet lag, I listened to a Reboot podcast that Jerry Colonna did with me and Cat Hoke, the CEO of Defy Ventures, a few weeks ago.

I had tears in my eyes while running, and I don’t think it was from my pace. Among other things, I’ve committed to bring Defy Ventures to Colorado in 2017. If this is something that is interesting to you either reach out to me or keep your eyes open for a broader fundraising initiative coming up (we’ve already raised 40% of the money needed to do this.)

And – enjoy the podcast. I think it’s one of the most powerful (at least to me) that I’ve participated in.

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Aug 11 2016

Love and Venture Capital

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

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

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

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

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

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

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

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May 26 2016

The Next Reboot VC Bootcamp

Signups are open for the second Reboot VC Bootcamp happening January 19-22, 2017. It will – once again – be at my house in Longmont, Colorado.

If you are interested, here are some reactions to the first Reboot VC Bootcamp.

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Apr 25 2016

Reactions To The First Reboot VC Bootcamp

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

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

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

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

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

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

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

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

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

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

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

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Oct 19 2015

A Conversation With Jerry Colonna About Life

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.

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