My dad’s posts over the past two days put me in a reflective mood about work.
I’ve been working hard around computers and entrepreneurship since the summer between my senior year in high school and my freshman year at MIT. That first real job was as the first employee of Petcom, a company started by a husband and wife team that grew to about 20 people before the oil and gas market for software evaporated in 1985.
Since then, I’ve been a founder of a number of companies, a CTO of a public company that acquired my first company, an angel investor, a VC in two different firms that I helped start, and an LP in a bunch of VC firms. I’m also a writer, run a foundation with my wife Amy, and do a lot of random things that support entrepreneurship.
I’ve tentatively explored a number of different activities that are adjacent to my daily work world, including academia and politics, neither of which are interesting to me in any meaningful way.
Whenever I reflect on my work over the last 36 years (going back to that first summer at Petcom when I was 17 years old), I end up thinking about which parts of my work I love. As I get older, I’m trying to spend most of my time on things I love, even if they are hard or unsuccessful, and with people who I enjoy being with. There’s always a non-zero percentage of my time that I have to spend on stuff I don’t like and with people I don’t like, but I’ve tried to structurally minimize that.
While it’s easy to make decisions around people, especially given all the mistakes I’ve made (and hopefully learned from) in the last 36 years, it’s been harder for me to figure out the specific work activities and cadence that bring me sustainable joy. I’ve had this come up in a number of conversations in the past few years with other entrepreneurs, especially ones who have either gone through a transition in their company or are burned out and exhausted from the intensity of their work.
In these conversations, the question of how I shifted from “operator” to “investor” inevitably comes up. One of the concluding lines in my dad’s Birth of an Entrepreneur post stood out to me.
“I am convinced that by creating an environment in which my sons can be creative and innovative, I have learned more from them than I have taught them.”
I had one of those tingly moments where I realized I was able to trace the roots of my philosophy of #GiveFirst back to my dad. If you are familiar with the concept of servant leadership, the sentence above will resonate with you.
I was president of my first company (Feld Technologies). My partner Dave was vice president. We didn’t use the CEO title because we didn’t know to, think to, or really care. We were partners and the titles demarcated something that might have been useful, but I remember that we behaved like partners.
While Feld Technologies was a successful company, and I was an effective president for seven years, with the benefit of hindsight I realize that I didn’t like my job very much once we had more than a few people working for us. At the time, I didn’t have a sense of what I wanted to do, I just worked incredibly hard.
After I sold my company, I went on a journey that included working for a public company, being part of the M&A deal team for a very acquisitive business, making a bunch of angel investments, starting a number of companies, and being chairman or co-chairman of several of these companies.
I straddled the operator / investor world until 2001 when the Internet bubble burst and my work world exploded into tiny pieces that collected into a huge mountain of shit that I had to work through. I finally realized a limit, and choose to abandon my operating roles and just be an investor.
Even then, there we many periods of time where I couldn’t answer “yes” to the question “do you love your job?” Instead, I just worked as hard as I knew how to work, independent of my emotional state around what I was doing.
Throughout all of that, I maintained that I was fundamentally motivated by learning. When I got depressed in 2013, I realized that I needed to modify the statement to say that “I am fundamentally motivated by learning and teaching.” That brings my back to my father’s quote.
“I am convinced that by creating an environment in which my sons can be creative and innovative, I have learned more from them than I have taught them.”
If you substitute “entrepreneurs” for “my sons”, you get the part of the job the I love.
“I am convinced that by creating an environment in which entrepreneurs can be creative and innovative, I have learned more from them than I have taught them.”
If you are familiar with servant leadership, you’ll recognize this concept. While my environment extends beyond just entrepreneurship, the construct of “creating an environment where <x> can be creative and innovative” has become foundational to my way of being. When I’m doing that, I love my job.
My dad clearly helped put me on this path, as did Len Fassler, who bought my first company and has continuously modeled this behavior for me. And, I often think of my uncle Charlie Feld (my dad’s brother), who taught me a lot and who still loves his job every day at age 76.
Do you love your job?
Today’s #GivingThanks post is for my dear friend Jerry Colonna. When I make a list of non-family members and non-partners who I would want to be stranded on a desert island with, Jerry is at the top of the list.
Before I tell a story, if you want to participate in #GivingThanks to Jerry, please make a donation to Naropa University where Jerry is the chair of the board. I was going to try to create some kind of complicated matching donation scheme since I hadn’t made a gift to Naropa yet this year but I decided to just gift them $10,000 (which I just did now through the website) so I encourage you to support at any level if you want to participate in my not-so-complicated match.
I met Jerry in 1995. I was chair of NetGenesis, which was the first angel investment I’d made after selling Feld Technologies (my first company). NetGenesis had raised some money and had created three different products – net.Forms (a web form manager), net.Thread (a web threaded discussion board), and net.Analysis (a weblog analysis tool). While our customer for each product was the same (a webmaster or a company trying to build a website), we were having trouble leading with all three products. Allaire was eating our lunch on .Form, a company called eShare was picking us apart on .Thread, and this new company called WebTrends was torturing us on .Analysis. A year earlier, none of this had existed – now we realized we needed to focus on one product. We chose net.Analysis and went about selling the other two products to different companies.
Jerry had just invested in eShare. Somehow Raj Bhargava (the NetGenesis CEO) had connected with Jim Tito (the eShare CEO) and worked a deal to sell him net.Thread. NetGenesis got some of eShares equity, eShare got the net.Thread product, and I joined the eShare board.
That started a 20+ year relationship between me and Jerry that I comfortably use the word “love” to describe.
Jerry became partners with Fred Wilson and they started Flatiron Partners. We all started working with SoftBank as affiliates (along with Rich Levandov). I eventually co-founded SoftBank Technology Partners (which became Mobius Venture Capital) and SoftBank (the corporation) became a 50% LP in Flatiron with Chase. We made more investments together. As Jerry and Fred’s relationship evolved, so did mine (with each of them) as we had different kinds of professional and personal connections.
I remember a moment in what must have been 1999, sitting at Jerry’s desk in NY in a dark office (I never really like office lighting so I work without it on and it had turned into evening in NY.) I was trying to get a deal done and it was a stressful mess. The tension of the Internet bubble bursting hadn’t started yet, but I was already exhausted and negotiating basically all the time with everyone about everything. I hung up the phone and put my head down on Jerry’s desk. I wasn’t crying, but I was probably in a parallel emotional zone. Jerry walked in the room, saw me, and wrapped his whole body around me and just covered me up. It was one of those moments I’ll never forget – total, compete emotional intimacy in the context of support. I’m sure he was feeling the same kind of stress and in the moment we just hugged. And then I cried.
Jerry has a super power – he makes grown men (and women) cry in a business context. But that’s the super power – it’s not a business context, it’s life, and he helps us understand that in powerful, unique, and profound ways.
In 2002 Jerry retired from venture capital and went on his own personal journey for meaning. He was an extremely successful VC but woke up one day hating the work, feeling unfulfilled, and struggling with what became a deep depression. I was fighting my way through my own dark shit then so we didn’t see each other often, but when we did it was extremely helpful to me. There was an immediate sense of comfort, of love, of empathy, and of understanding. It didn’t matter what we talked about – we were just there, together, in the moment.
Today, Jerry runs a CEO coaching company called Reboot. Their mission – front and center on their website – says it all.
“We believe that in work is the possibility of the full realization of human potential. Work does not have to destroy us. Work can be the way we achieve our fullest self. Reboot is a coaching company. We help entrepreneurs and their teams deal with the internal ups and downs of entrepreneurship and support the growth they need to improve their performance and their life.”
I believe that Jerry is the best CEO coach on this particular planet. I’ve seen, and experienced, his magic many times. He’s found his purpose in life, and it’s wonderful to see him practice it every day.
Jerry also moved to Boulder last year. That means I see him a lot more in person that I used to. I still have to make a mental adjustment when Amy and I run into him and Ali on the Pearl Street Mall heading off to different restaurants for dinner, but an enormous smile always crosses my face when it happens.
Jerry – thank you for being you. And for everything you do in this world.
After spending most of the day at littleBits yesterday, I finished it with an annual tradition that is one of my favorites.
At 6:45pm Amy and I met Joanne Wilson, Fred Wilson, Matt Blumberg, and Mariquita Blumberg at Marea for dinner. Fred and I are both on the board of Return Path, the company Matt has been running since he co-founded it in 1999. For over a decade, we’ve been having an annual dinner as a group when Amy and I are in NY, usually in the fall.
Joanne generally picks the restaurant and Amy and I are happy to defer to her excellent taste. We are staying at Columbus Circle so this year Joanne picked something within walking distance for us. As Amy and I were walking home around 9:30, we each commented on how wonderful this tradition is.
I woke up this morning thinking about annual traditions. I’m not a Hallmark holiday person, I don’t like Christmas (although I’ve learned not to be grumpy about it), Thanksgiving crushes my soul, and I’ve never really understood Easter. I’ve learned how to give awesome presents on Valentine’s Day, but I think that’s more because I’m uxorious and well-trained. So I like annual traditions that are out of step with everyone elses.
When I reflect on our dinner, and the conversation, the six of us are enjoying marking the passage of time with this tradition. We are all getting older together, a little softer looking (at least me and Matt), greying at the temples and in the beard (again for me and Matt). We started doing this before Matt and Mariquita had kids and when Fred and Joanne’s kids were pre-teens. All three of Fred and Joanne’s kids are now out of the house and they are starting the empty nest phase of their life.
While it’s amazing to watch time pass, it’s even more powerful to experience the passage of time together. While we all interact regularly, this annual dinner, which is a deeply engaged three-ish hour meal, gives us a chance to really be together, in the moment, and share what is going on. When you link it together over a decade of more of three hour slices, along with all of the other interactions, it allows us to know each other in a uniquely intimate way.
I felt real love and real joy last night. Joanne, Fred, Matt, and Mariquita – y’all are awesome friends. Thanks for being part of my life.
This morning’s question during my Headspace meditation session was “Who or what would you miss the most if you weren’t here.”
Over the last few months, my meditation practice has been spotty. Something indeterminate happened and I just fell out of the routine. I’ve been told by my meditating friends that this happens often and not to worry about it, but rather just to start practicing again when you feel like it.
I’m feeling very maxed out right now. I know there’s some cliche about VCs taking it easy in August but that never seems to be my reality. For the past 45 days I’ve pretty much been saying “no” or “I don’t have any time” to anything new that has come up. I don’t really see that changing – I feel full – so this morning I sat down to meditate for 20 minutes.
As I sat down and got comfortable, I realized how incredibly tense I was. Not just physically tense, but mentally and emotionally tense. I carry a lot of tension in my shoulders and when there was a big pop, it was more than physical. I settled into the meditation session and a few minutes in was confronted with the question “Who or what would you miss the most if you weren’t here.”
Amy and Brooks immediately came to my mind. Bing bing bing – I got the right answer. But I know it’s not about that so I just let the thought float away.
Robin Williams came into my mind. I was sad that he was in such distress that he took his own life.
A friend who is going through a divorce surfaced. The pain from my first marriage and divorce jolted through me.
Amy and Brooks came to my mind. I held them there for a few moments.
A work issue that is front of mind intruded. I observed that I was having the thought and let it float away.
Amy and Brooks again.
I felt the tension leaving my shoulders. I sat a little deeper. I listened to what Andy from Headspace was saying, but I didn’t really hear it.
I tried on the feeling of what it would be like to not be here. I wasn’t hear, but was somewhere else, observing here. That became really uncomfortable, so I let it go.
Amy and Brooks.
As I finished the session and stretched, I felt everything soften. My shoulders are less tight. My gaze is softer. I’m clear about who I would miss the most and am going to go spend a little time with them before the day starts in earnest.
Who would you miss the most if you weren’t here?
I’ve been thinking a lot about human – computer love recently given my obsession with Battlestar Galactica. It evolved from “can Cylons have feelings?” to “can Cylons and humans love each other?” to “what changes when Cylons become mortal?”
So – when I saw the trailer for Her, I thought – yup – this is our future, and we’d better start getting our minds around it.
I look forward to Siri starting to sound like Samantha.
Owen’s rules of love are (1) Don’t limit your love, (2) Let yourself be loved, and (3) Never give up. Good lessons for all human beings.
Now, while I know it’s Valentine’s Day (and I’ll behave appropriately), I am very much looking forward to Valentine’s Day for Guys which happens in a month. In the mean time, remember that all you need is love.