Sources of Insecurities

When I was in LA last week, I had breakfast with Nick Grouf. We’ve been friends for 20 years and, while we don’t see each other often, it’s the kind of friendship that immediately lets you talk about deep, interesting things with almost zero foreplay.

At a small Coffee Bean coffee shop in Hollywood, with a music track from our childhood playing over and over again (I’ll spare you the track so it doesn’t get stuck in your head also), we ended up in a discussion about sources of insecurities.

Nick made the assertion that unless you fundamentally don’t feel safe on this planet (e.g. you experienced death of a child or were raped as a kid), there are two primary sources of insecurities.

Either:

  1. You don’t feel lovable or
  2. You feel like a fraud

We then went through a list of people we knew and tried to come up with another primary source of insecurity. Nick was clear that his source of insecurity is that he doesn’t feel lovable. We quickly were able to label a few of our good friends this way. The second – you feel like a fraud – is widely understood and expressed through the startup community as imposter syndrome. We bounced around this for a little while and then went on to the next topic.

But, this stuck with me. While I’ve never struggled with either of these, like all other humans I know, I definitely have some insecurities.

As I pondered this, I came up with the notion that my insecurities are driven by my feeling of being overly responsible for things, especially those I am not responsible for, and cannot impact in any way. This was one of the sources of my first major depression in my 20s and over the years has resulted in multiple situations where I’m completely worn myself out trying to “fix things” that were broken.

At 50, I’ve mostly let go of this. I rarely find myself in a situation where I feel like I’m being overly responsible for something I shouldn’t be, or cannot impact. I also rarely feel insecure anymore, although I attribute that more to me working on the issue, rather than just aging out of the emotion.

There’s a cliche in business that you should always try to surround yourself with people who are smarter and more capable than you are. I’ve never felt like it was a very nuanced cliche, as different people have very different strengths and weaknesses and the “more capable” person is going to be very context specific.

As we were talking about sources of insecurities and this cliche came up, Nick made a different suggestion which I hope is either a cliche or will become one. It’s that when you are in a foxhole in battle, you want the person with the strongest arm to throw out the grenade.

Ponder whether one of these sources of insecurities apply to you. I’d love to hear if you think there are other fundamental sources of insecurities. And, when you are next sitting with your team (regardless of your role), observe whether the person with the strongest arm is throwing the grenade out of the foxhole.

Up Close and Personal: Conversations on Entrepreneurship and Mental Health

I’ve talked openly about my struggles with depression over the years and have engaged deeply in an explorations of entrepreneurship and mental health through several different organizations I’m involved in.

On February 16th, from 3pm to 5pm, I’m doing a free public event with the Carson J Spencer Foundation about entrepreneurship and mental health. For some quick context, they did a short intro video with me on the topic.

If you are interested in participating, please register and join us on February 16th at the Museum of Boulder.

Upfront and the Power of Startup Community in LA

I’m finally home after three solid weeks on the road which included Austin, Dallas, New York, Boston, Philadelphia, and Los Angeles. It’s delightful to sit in my green zebra chair in Amy’s upstairs office, with a cup of tea, the Diana Krall channel playing on Pandora, and just catch up on stuff.

The extra points from my trip was getting to spend some face time with close friends and family that I haven’t seen in a while. Amy joined me in LA and we had dinner with Fred and Joanne Wilson and then went art shopping with Fred on Sunday. I spent a weekend in Dallas with my parents and went to Dairy Queen for Blizzard’s three times with my dad (my mom tagged along and even had a Blizzard one night.) I had dinner with my Uncle Charlie, Aunt Cindy, Cousin Jon, and his son Jack. You get the picture – even though the travel was intense I got some time with humans I love and don’t get to smell as often as I’d like to.

At the end of the trip, I spent two days at the Upfront Summit in LA. This comes on the heals of Upfront managing director Mark Suster’s great post titled Embracing Your Community as a Strategy which I encourage you to read as it is magnificent.

I have a long relationship with LA. In my first company (Feld Technologies) my first large client was in LA (Bellflower Dental Group). While the company – a large 100 person dental practice – was based in Bellflower, the dentist that owned it lived in Mandeville Canyon and I usually stayed at his house when I was in LA (he was the step-father of a fraternity brother, which is how we got connected in the first place.) I drove a lot in LA and learned things like how the 10 connects to the 5 to the 605, or the 405 to the 605. I learned that if you left at the right time, each route was only 30 minutes, but if you left at the wrong time, it was over two hours. I heard about Wolfgang Puck before he was in airports everywhere. I enjoyed the non-meat dishes at Hamburger Heaven, went to The Palm when there was only one location, and hung out in Santa Monica before it was techie cool and the only thing around was Peter Norton.

Today, our current investments in LA include OblongNix Hydra, and recently Two Bit Circus. In the last five years, there has been an explosion of startup activity in LA that continues to be exciting as the startup community grows and evolves. Mark and his gang at Upfront Ventures are in the middle of it and are having a huge positive impact on things.

Over the last 20 years, I’ve attended and hosted many VC annual meetings. I’m an investor in many early stage VC funds and, while I’m not a rigorous annual meeting attender, will go if one of the GPs asks me to. I always offer to be part of the content of whatever meeting / summit / dinner they do if it’s useful to them.

Since I was already in LA on Monday, I told Mark I’d stick around for the Summit if he thought it’d be useful to him and the team. He immediately programmed me into the content for Wednesday (LP/GP day) and Thursday (entrepreneur day). Mark also invited me to the Upfront annual meeting given (a) our Next strategy and (b) my new partner Lindel Eakman being a prior investor in Upfront when he was at UTIMCO.

The annual meeting was solid and consistent with high quality annual meetings. But the Summit on the follow two days was easily the best VC-driven summit that I’ve ever attended. The content was incredibly high quality, diverse, and stimulating. There was plenty of networking time organized around the content. The venues were awesome. The coordination and organization was first class. The attendee list was dynamite. My understanding is that Mark / Upfront are going to post the content online and I’d encourage you to watch many of the videos when this happens.

It being LA, the special bonus things I got to do, like the one pictured below, was about as good as it gets. Yes, Kevin Spacey is extremely smart, interesting, and extremely articulate – as I expected, but there’s nothing like getting to spend a few minutes with someone you admire (he’s always been one of my favorite actors), but have never met.

Kevin Spacey with Fanboys

Mark, Greg, Stuart, and gang – thank you for including me in this. You are doing amazing things in the LA startup community.

Introducing The Dial Telephone

If you are over 80 years old, you experienced the transition from the non-dial telephone to the dial telephone, which included the magic “finger stop.”

If you are 30, imagine what you will be reflecting on 50 years from now.

Is History A Guide In Business?

I was at a fascinating dinner with a bunch of founders and investors last night. Until I was 35, I was often the youngest guy in the room. While this was a seasoned crowd, much of the experience – both around creating companies and funding companies – started around the mid-2000s. As someone who has been doing this since the late 1980s (I started my first company in 1987) I definitely felt like one of the old guys in the room.

At some point, the conversation turned to the current state of things in the broad entrepreneurial ecosystem – both company-side and investor-side. It rambled around for a while but kept locking down on specific issues around the current state of financings and exits, alignment between founders/investors/acquirers, cultural norms that were front and center in today’s startup communities, and a bunch of other issues that tied back to the wonderful Game of Thrones line “winter is coming.”

Throughout the evening, I was regularly reminded of my favorite BSG quote. “All of this has happened before, and all of it will happen again.”

Another one of my favorite quotes is the one attributed to Mark Twain, “History does not repeat itself, but it rhymes.Phil Weiser, Dean of the CU Law School and a good friend, often pulls this one out to remind us to look to the past to understand the future.

While we’ve been in a particular strong part of the startup / entrepreneurship cycle for the past four years, many people are nervous, talking about it, reacting to it, and getting confused, frustrated, and scared by what is going on. Others are in total denial of reality, which never works out well in the long run. Whether you follow the BSG theology or subscribe to Mark Twain, or are somewhere in-between, you recognize the value of understanding the past to exist in the present and deal with the future.

I came out of dinner with about 20 topics for blog posts, many which reflect on lessons I’ve learned multiple times over the past 30 years, which can be applied to today, and tomorrow, and the next few years, regardless of what actually happens. Until last night I wasn’t particularly motivated to blog around this stuff, but the discussion, and people in the room, really stimulated me to put some energy into this. So I plan to.

But remember, all of this has happened before, and all of it will happen again. So if you are impatient, I encourage you to go look at posts from me, Fred Wilson, and David Hornik from 2004 – 2007 for a taste of what I would characterize of “the re-emergence from winter.”