Brad Feld

Tag: jerry colonna

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.

Gartner Hype Cycle

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.


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.


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.


I was catching up on a bunch of reading on the web from last week and came across a post by Lars Dalgaard titled Thoughts on Building Weatherproof CompaniesI don’t know Lars, but know of him as the founder/CEO of SuccessFactors and now a partner at A16Z, and was curious after recently reading a Forbes article about Zenefits a few weeks ago titled ‘A Lot Of Things Went Wrong’: Lars Dalgaard On Zenefits Scandal.

Any CEO I’ve ever worked with has heard me say “build the company and make decisions as though you’ll be running it forever” many times. While forever is a very long time and so far the idea of running a company forever hasn’t happened, it’s a great frame of reference for a CEO to operate from. So, I found myself nodding at a bunch of things Lars wrote in his post and I encourage you to read it.

Following are a few of the headlines of the points that resonated with me along with my quick thoughts.

Successful companies are bought, not sold: This cliche is said 100x per day by VCs. And it happens to be true. Build something great and important and opportunities to be bought, whether you want to pursue them or not, will come to you.

Develop a perpetual, aggressively help-seeking mindset: A simpler way to say this is “learn quickly, do it continuously, and surround yourself with people you can learn from.” There’s a subtext about sublimating your ego and fears, which appears in several other parts of the post and is a characteristic of everyone I know who is a learning machine.

Invest in a coachMany of the CEOs (and founders, and execs) we work with have coaches. We strongly recommend them. My partners and I have used Nancy Raulston since we started Foundry Group and my extremely close friend Jerry Colonna is someone I describe as “the best startup CEO coach on the planet.” I have a running coach, even though all I do is run marathons, and not competitively. I’ve never understood why people who are trying to be excellent at something don’t recognize the value of a coach.

Build a real board of directors … and use itI’ve long been an advocate of building a real board early in the life of your company. Lars talks about adding non-VC directors early and I strongly agree. I’ve seen too many boards that are just gradual expansions of the number of VCs around the board table with each successive round of financing. While the CEO works for the board, a great board effectively works for the CEO also, doing whatever it can (as individuals and collectively) to help the CEO be successful with one fundamental governance role – that of insuring that if the CEO is not being effective, the board can take action to change this, which often, but not always, means replacing the CEO. If you want to go deeper on this, I’ve written a book on it called Startup Boards: Getting the Most Out of Your Board of Directors.

Kill the monsters of the mind, while preserving your spiritWhile a provocative title, I’m not sure your goal should be to kill the monsters of the mind. In my post titled Something New Is Fucked Up In My World Every DayI tell a short version of the Buddhist saint Milarepa’s story Eat Me If You WishComing to terms with the monsters (or demons) is much more powerful (and efficient) than killing them, since it often makes them simply disappear.

Don’t lie to yourselfI remind you of the great John Galt quote “Nobody stays here by faking reality in any manner whatever.” If you ever stay in my guest condo in Boulder, you’ll see a painting by my mother with this quote incorporated into it hanging on the wall.

It’s Sunday – if you are reading this, take some time to read Thoughts on Building Weatherproof Companies and ponder it in the background, instead of burning brain cells on whatever political crap is discussed on the internets today. Lars, thanks for taking the time to write 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.


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.


I got the following email recently, titled “Unicorns Without The Magic.”

“With the rise in venture capitalism it’s hard to say the word “start up” and not be offered an abundance of accelerator programmes, free office space, free apartments & a free bible of connections. I myself have felt the pressures of the world of start up wonders & the prospects of investment. Whilst finishing my finals at university, I created my own algorithm for a business model to achieve a sustainable competitive advantage in a digital space. Through this I’m now building my first digital ecosystem, but along with it I’ve been offered numerous places in accelerator programmes, numerous loans and a wave of unicorn magic dust that seems to be collecting in my inbox. I’m not complaining, but what happens if the purpose of a business is greater than ones own self interest and certainly greater than a VCs interest? Our purpose is to give other people the tools to create their own opportunities, which is not necessarily in line with most VCs sentiments. I know in the next five years my company will make a lot of money, but what I don’t know is how as a 23 year old entrepreneur to says yes to the right VC and no to all the magic dust.”

My short answer was:

“My advice is simple – if it doesn’t feel good / right, say no. Keep focusing on building your business. Don’t avoid the interactions, but use your filter – which seems well tuned and appropriate – to make sure you are only spending time with people who you want to spend time with.”

I was reminded of this by Fred Wilson’s post this morning Go East Young Man (or Woman). He tells Henry Ward’s story of the financing for eShares.

“We were 0 for 21 with Silicon Valley VCs. I never got close. Most of the big firms wouldn’t even meet. A few had an associate do a Skype call even though we were 20 minutes away.

After 21 meetings in SV, I took a Hail Mary trip to the east coast and met with 3 funds. All 3 invested.”

We see this all the time. Founders who are entranced with Silicon Valley VCs. They pursue them with no focus on anyone outside of the bay area, get rejected right and left, often by associates, and end up feeling like they’ve failed. Fred’s post – and Henry’s at eShares Series A – has a great punch line that reinforces the importance of a founder having an effective filter.

“Fundraising is simple: find investors that get excited about your company. It is a filtering exercise. Too many founders believe they have the wrong pitch instead of realizing they have the wrong audience.”

Special bonus points (and some 1990s nostalgia for you): Do you remember the other company named eShares which Fred previously invested in via Flatiron Partners? I sat on the board of with Fred’s partner at the time Jerry Colonna. (a) What did they do? (b) Who acquired them? (c) How much where they acquired for? (d) Who did they compete with and what happened to their competitor?


I’ve been very open about my struggles with depression over the years. A few weeks ago, I participated in a Q&A with Greg Avery at the Denver Business Journal titled Brad Feld Q&A: Bringing depression out of the shadows in startups. It was part of a more extensive series on Depression, entrepreneurs and startups.

Since I’m still getting emails about it, I thought I’d republish the Q&A here.

Q: How common is the issue of depression in the startup world?

A: Very common, although it is rarely discussed. While the line between stress, deep anxiety, and depression often blurs, most entrepreneurs struggle with broad mental health issues at various points in their lives.

Q: How hard was it to acknowledge your struggle to yourself? And how hard was it to explain it to your partners and your peers?

A: Initially it was extremely hard. When I was in my mid-20s, running a successful company and clinically depressed, I was afraid to talk to anyone other than my psychiatrist about it. I was ashamed that I was even seeing a psychiatrist.

I was afraid people wouldn’t take me seriously, or would stop respecting me, if I talked about how bad I was feeling. The only people I talked openly about it with was my business partner, Dave Jilk, and my girlfriend — now wife — Amy Batchelor. They were amazingly supportive, but even then I was deeply ashamed about my weaknesses.

Q: When did you start to be so open about it?

A: After I became depressed for the second time, in my mid-30s — in 2001 just after Sept. 11 through the end of the year. The last three months of 2001 were awful for me after an 18-month stretch from the peak of the Internet bubble — spring 2000 through Sept. 11, 2001. That was a relentless slide downhill on all fronts.

Sept. 11 was the trigger point for this depression. I was in New York City after a red-eye from San Francisco, landing at 6 a.m. on 9/11. I was asleep in my hotel room in midtown [Manhattan] when the World Trade Center towers collapsed. While I was never in harm’s way, I was terrified, exhausted, and emotionally distressed.

Once I got back to Boulder, I didn’t travel for the rest of the year. In 2002, when most of my VC and entrepreneurial colleagues were having a terrible year, I acknowledged how much I had struggled in 2001, although I was still relatively discreet about it.

When I got depressed again at the end of 2012, I was open about it this time as it was happening and throughout the process. I knew at this point how to handle it and that it would pass.

I also knew many, many entrepreneurs also struggled with depression but, like I had been earlier in life, were afraid to discuss it.

Q: How much does the issue of mental health differ in startups from the world at large?

A: In general, I don’t know. But leaders and entrepreneurs are programmed to “never show weakness”, so I expect there’s much more pressure to keep it hidden and suppressed, which if you’ve ever been depressed, can make things much worse.

Q: Looking back, how much has your work, or work style, been a factor in your depression?

A: There are many things about my depressions that I still don’t understand. I have been able to identify trigger points for the various depressions, which include physiological exhaustion, boredom, and major life changes [divorce, dropping out of a Ph.D. program].

Most recently, things started with a 50-mile race I did in April 2012 that I never physiologically recovered from, followed by a near-death bike accident in September 2012, a very intense stretch of work which included writing two books in the midst of everything — “Startup Communities” and “Startup Life” — the death of my dog, and ultimately a kidney stone that required surgery.

At one level, I was exhausted. I was also bored — my work was fine, but I wasn’t learning very much. I’m hugely intrinsically motivated and have always believed that I’m fueled and motivated by learning. In this case, I was teaching a lot, mostly around “Startup Communities”. But I wasn’t spending any time learning. After coming out of the depression, I realized this was a huge part of things and have subsequently redefined my intrinsic motivation as a combination of learning and teaching. Now that I’m 49, I realize this makes a lot more sense.

Q: How well does the startup and VC world handle issues of mental health? What would you change about it?

A: Until a few years ago, we generally sucked at it. The philosophy around leaders and entrepreneurs never showing weakness dominated and we were told never to let ourselves be vulnerable. Fortunately, leaders like [venture capitalist and professional coach] Jerry Colonna have helped many leaders and entrepreneurs understand the power of being vulnerable and we now at least have an open and productive conversation around it.

Q: Can an executive afford to show any vulnerability and still hope to succeed in leading employees and attracting funding?

A: Yes absolutely. It’s all about culture, style, and self-awareness. And, it’s much easier to be yourself, allow yourself some vulnerability, intellectual and emotional honesty on your path to being a great leader.

Q: What would you say to a founder who’s grappling with depression but feeling their success might hinge on not letting it be known?

A: I mostly try to listen, be empathetic, and introduce the person to other peers who have struggled with the same thing. I talk openly about my experiences, but claim them as mine, rather than suggest that there are generic solutions.

When ask directly what to do, I offer opinions, but I don’t lead with them, nor do I expect that I will — or that I can — solve the person’s problem. I can simply be a resource for them.

Q: Have you actually had these conversations?

A: I’ve had these conversations many, many times.

Q: What do you suggest to people who need help?

A: Talk to your mentors, your peers, and your partners. Take the risk of being vulnerable.

Q: Are there resources you’ve discovered that are particularly geared or well-suited to entrepreneurs?

A: Jerry Colonna’s Reboot.io is the best organization in the world for this.


In The Cave of DemonsThis is one of my favorite lines to use to explain the business life I live. When asked what it’s like to be a partner in a VC firm, be on a bunch of boards, and have a continuous stream of random interaction come my way, I like to level set my reality.

It’s simple. Something new is fucked up in my world every day.

Now, just because something new is fucked up, doesn’t mean I’m unhappy. Quite the opposite – I’m usually happy, although when the pile of fuckedupness gets high enough I get tired. And day after day after day of 12+ hour days also make me tired. I used to be able to work through the weekends – now at 49 years old I need them to recover, get patched up by Amy, and get ready to go back out there.

Jerry Colonna at Reboot.io tells a wonderful story about the crucible of leadership on Fred Wilson’s blog with a section titled Eat Me If You Wish (read the whole post but the parable is about half way through.) It’s worth repeating here. Take your time reading it.

“One day,” begins a story re-told by Aura Glaser in the latest issue of Tricycle Magazine, “[the Buddhist saint] Milarepa left his cave to gather firewood, and when he returned he found that his cave had been taken over by demons. There were demons everywhere! His first thought upon seeing them was, ‘I have got to get rid of them!’ He lunges toward them, chasing after them, trying forcefully to get them out of his cave. But the demons are completely unfazed. In fact, the more he chases them, the more comfortable and settled-in they seem to be. Realizing that his efforts to run them out have failed miserably, Milarepa opts for a new approach and decides to teach them the dharma.

“If chasing them out won’t work, then maybe hearing the teachings will change their minds and get them to go. So he takes his seat and begins… After a while he looks around and realizes all the demons are still there…At this point Milarepa lets out a deep breath of surrender, knowing now that these demons will not be manipulated into leaving and that maybe he has something to learn from them. He looks deeply into the eyes of each demon and bows, saying, ‘It looks like we’re going to be here together. I open myself to whatever you have to teach me.’

“In that moment all the demons but one disappear. One huge and especially fierce demon, with flaring nostrils and dripping fangs, is still there. So Milarepa lets go even further. Stepping over to the largest demon, he offers himself completely, holding nothing back. ‘Eat me if you wish.’ He places his head in the demon’s mouth, and at that moment the largest demon bows low and dissolves into space.”

I put my head in a demon’s mouth every single day. Often, it’s a different, or new, demon. Sometimes it takes me a few days to get ready for this so the demons back up. Other days two or three new demons appear and I can only deal with one of them so the others hang around.

I learned how to deal with this in 2001. That year started out miserable with companies I was involved failing all around me. I did everything I knew how to do to help. I’d go to bed at the end of the day thinking, “Ok, that totally sucked, but tomorrow will be better.” It wasn’t – each day was worse. By about June I realized that every single day of 2001 had been worse than the previous day. I finally metaphorically threw up my hands and internally said, “Fuck it, let’s see what the world can bring on today.” That’s when I started to sit with the demons.

Up to that point, I was fearful of what the day would bring. I would fight against it. I would thrash around looking to solve every problem, chasing the demons around my cave trying to get them to leave. And then 9/11 happened, on a beautiful morning in New York, while I was fast asleep in a hotel room in midtown Manhatten at The Benjamin Hotel after taking a redeye from San Francisco. As the planes crashed into the World Trade Center towers, Amy frantically called me from the road as she was driving to the airport to come visit me in New York. I had turned off my phone so I expect I snored happily away as the first tower fell. When I finally woke up I to whatever station the clock radio was on, I thought it was all a joke. For about a minute, I struggled through the post redeye haze that enveloped me, along with the existential fatigue I was feeling from nine months of companies failing everywhere, people being angry, unhappy, depressed, stressed, scared, and under immense pressure, and then I realized it wasn’t a dream.

When I finally woke up enough to turn on my phone and call Amy, I was lucky enough to get through. She pulled over to the side of the road and cried. She was sure I had been on one of the planes that had crashed. After a few minutes, we realized a trip to NY was silly so she turned around and went home. I then took a shower and tried to process what was going on and figure out what to do next.

There’s a lot more from that day that shaped me, like it shaped so many others, but suddenly many of my demons just disappeared and went to torture other people. I realized that as fucked up as my world was, it was trivial compared to what was going on 60 blocks away. While I was terrified and trapped in The Benjamin for a while, I had at least four hours before I took action to just sit and process things.

Dealing with the particular set of demons in my cave at this point to another three months. That period was my second of three clinic depressions that ended around my birthday on December 1st. I spent these three months sitting with all of my demons, welcoming more into my world, and just learning from them.

When the really scary ones showed up, I didn’t fight. I just placed my head gently in each of the scary demons’ mouthes and said “eat me if you wish.”

Just like with Milarepa, it worked. And it’s now how I live every day.