Learning from the Fire Hose

I am a first time founder & CEO, but I am not new to the world of tech companies. However, even with my…ahem…decades of experience, I am amazed at the volume of learning I am managing on a weekly basis. Being a startup founder is for you if you love to learn, perhaps more than you can handle.

When I first got into venture capital, I often heard young VCs and the Kauffman Fellows Program staff refer to the program as “drinking from the fire hose.” I think there were elements of truth to that with regard to the VC world, but I think it pales in comparison to the volume that comes with being a first time founder and CEO.

I read somewhere that in a startup, the term “CEO” actually stands for Chief Everything Officer. It is true that you wear so many hats in the course of a day, week or month. You are working on product, marketing, finance, hiring, board management, team management, legal, vendor management–all of it.

But man, what learning. In each of these areas, you may bring some skills, perhaps even advanced skills. But even if you do, your skills are in a different context, under different time pressures, with (generally) more help. For me, I am learning hands-on specifics about PPC, email marketing, A/B testing, project management, site design, and so much more.

Beyond the business and skill learning, I am also learning a ton about myself. About better personal time management discipline, about needing to continually keep my motivation high, about powering through moments of procrastination, about brutal focus. I often ask, “What is the single most important thing to do to advance the business?” But then, how do I allocate time for networking, which I know I need for perspective, emotional support, and to broaden my view, but which may not qualify to advance the business today?

I struggle with enjoying the journey, and not just the destination. I need to keep reminding myself how much I am learning.

Finding the RIGHT investors

I recently went through a low point, a crisis of confidence in our startup’s plan, the team, and myself.

Anyone who has been through startups knows that this happens in the seed phase, often multiple times. (As an aside, I am amazed at how few people admit it.  Everyone else seems to be “crushing it.”)

After multiple phone conversations, I had a Board sit-down meeting where I led the board through a number of alternatives. Our seed stage VC was such a voice of calm reason, helping to guide the conversation and helping me to see the big picture.

It struck home with me how lucky I am to have this VC investor and mentor.

While I know he has a duty to look out for his investment, I never felt that he was doing so during this conversation or the follow ups. What I felt was his concern, guidance, and empathy.

So entrepreneurs, do heed the guidance of those who tell you to do your due diligence on your investors- check with other management teams how your investors have acted when things are not going well. It will give you a sense of what support you are likely to get when you go through it.

Feeling Blessed

I did not wake up today remembering that it was 9/11.

Instead, I woke thinking about my blessings: my family, my health, my supportive wife, my entrepreneurial journey (which I try to remember is a blessing despite the wild ups and down of the business and my psyche). I am so incredibly grateful for these blessings and so many more. I am trying to use gratitude as a way of channeling my energy, anxiety, and ADD tendencies. I think it’s working.

But realizing that is it 9/11 prompted all kinds of other feelings and memories:

Twelve years ago today, I was attending a board meeting as a VC.  Another board member was attending the meeting by phone and alerted us that a plane had flown into the World Trade Center. We all thought it was a small craft and kept going with the meeting. When he informed us that another plane had hit the Center, we adjourned the meeting. I spent the afternoon and evening watching the news with my wife, feeling numb and helpless.

-Realizing how thankful I am that I am in good health. I am rather lucky that my genetics enable me to keep my weight stable despite not working out anywhere near enough and with high levels of stress. I really need to change my workout pattern, for stress and sleep benefits. Today I re-committed to that.

-I am trying to enjoy the journey, the learning, the personal growth, especially that which comes from being an entrepreneur.  As a goal driven person, it has been quite a challenge for me to embrace the uncertainty, the downs (that of course go with the ups), and the feeling that, some days, I don’t know what I’m doing. This has arguably been one of the toughest things I have ever done. Through another blog, I came upon these beautiful words from Antonio Machado- “Traveler, there is no path. The path is made by walking.”

-Thankfully, 9/11 didn’t impact me directly too much. But thinking further about my blessings has heightened my understanding of how precious my relationships are with family and friends. I have not done a particularly good job in including the friend part of my life with business and family. It’s tough to do, but I am increasingly realizing that it is something I need. As driven as I am, and as much as I attach self-worth to my work, it is family and friends that really give life meaning. I don’t have enough friend connectedness right now. That needs to change.