6 / Captain's Log: December 2020

Each of us needs our own village of people, and 2020 has made that particularly hard. Even before COVID, I would often cite a quote from Kurt Vonnegut:

“When a couple has an argument nowadays they may think it’s about money or power or sex or how to raise the kids or whatever. What they're really saying to each other, though without realizing it, is this: ‘You are not enough people!’”

For the last six weeks, Kate and I have been staying with Danielle and Kevin Morrill at their house in Denver. It’s been refreshing to have someone other than Kate to talk to on a regular basis—COVID has left us putting an awful lot of pressure on our significant others. But we couldn't shake the desire to be home, to have a quiet breakfast in our sun-filled breakfast nook, and ironically ready to have fewer people.

When I wrote the first edition of Letters nearly a year ago, I wanted to use the format to build new friendships and help water relationships I’d neglected—I wanted to find more people. I modeled my newsletter after Tobias Van Schneider’s newsletter, which is a blend of personal and professional.

Now, more than 2,000 people are subscribed and I’m not really sure what for. It feels self-indulgent to write to 2,000 people just telling them what I’ve been up to and what I’ve been thinking about. But this self-indulgence has led to beautiful new friendships, coaching clients, and encouraging responses that I'm plain addicted to now.

So I guess I'll keep doing this for a while.

As I sat down to write, wiggling my fingers to loosen ‘em up, I realized the last six weeks have been some of the most exciting and productive of my life. Not only have I made a lot of progress, I’ve learned enough to transform my thinking on more than one subject.

Short Updates

  • Coaching: Over the last six weeks, I went from having ~8 coaching clients to having 17. I’m almost at my max. A huge thank you goes out to Kevin Lee, who graciously referred a boatload of people to me after his thread on the value of coaching. I did not expect to grow this brand new business so quickly. It’s incredibly cool that learning to be a coach teaches you so much about yourself—and it’s useful at home, too. The school I’m starting in January, The Hudson Institute, has a saying (even the title of a book), Self as Coach, Self as Leader. It starts with you. How you show up. And every time I open a coaching book or start a session, I now know I’m about to learn something about myself. I feel like I’ve gotten 5 years of personal reflection and growth packed into three months.

  • Incorporating: I incorporated an LLC to handle the business, Sparks Industries, LLC (hat tip to Marvel there). I’m grateful I was able to use my experience as a COO & CEO to get things spun up, otherwise this would have been daunting.

  • Wealth (for the romantics): Over the last 10 years, I’ve lived in San Francisco. As a startup founder, I went through periods where I earned a more than healthy salary, and other periods where I had no income for entire quarters at a time. I didn’t save much money, and I’m conflicted on how to feel about that. On the one hand, I wish I had a nest egg to go buy a house and begin, well, nesting. On the other hand, in my twenties I used this Robert Greene quote as my own personal mantra: “All that should concern you in the early stages of your career is acquiring practical knowledge in the most efficient manner possible.” I focused on new skills, knowledge, deepening friendships and building new ones with creators I respected. In those domains, the domains of knowledge and relationships, I feel wealthy.

  • Wealth (for the econ-geeks): I’ve been reflecting on how compounding applies to other forms of capital beyond financial capital (as in a 401k). Social capital is “the durable network of social and professional relationships through which founders can identify and access resources” (Wasserman, loc. 770) and “human capital is human capability based on knowledge, education, training, skills, habits, etc.” (Goodwin, 2003). While I haven’t saved much money to compound, transitioning to a career as a coach has shown me that I’ve certainly compounded social and human capital.

  • Independence: Depending if you count the “brewery” from college, this is my fourth or fifth company I’ve started. But this one is different: no partners—just me. This is a deliberate experiment to own all the success (and the failures). So far, I’m enjoying the freedom to set my own schedule and do things “my way.”

  • Studying: There’s an ancient Chinese expression, “Theory without practice is foolish; practice without theory is dangerous.” While I’m doing about ~20 hours of coaching per week now, I’m churning through the curriculum books for Hudson and others that pique my interest like main and side quests in an RPG. At past companies, I would read a book on marketing here, a book on CEO-ing there, but studying was never as formal of a part of my work as it is now. Reading felt like it was something I’d do “when the real work was done,” but I have a strong hunch that was pretty backwards.

  • Rhythm vs. Schedule: In November, I completed a prerequisite for my coaching certification program with The Hudson Institute called “LifeForward.” It’s a program to help expose aspiring coaches to their method in practice, but it’s also like getting a concentrated shot of coaching in 5 days. One coach, Deb, introduced me to the idea of a rhythm vs. a schedule. As a CEO, my days were scheduled to the minute. As I began coaching, I fell into that old habit. But Deb helped me realize the need for rhythm, which includes the flexibility of jazz. So I blocked off Wednesdays for “play days,” where I wake up and decide what I want to do without anything scheduled.

  • Resentment & Anxiety: As I’ve been studying coaching methodologies, I’ve been learning about “moods” or “prolonged emotional states.” I’ve learned that I’ve routinely found myself in two ugly and unproductive moods: resentment and anxiety. The first has to do with not accepting facts, things that have already happened. The second has to do with not accepting uncertainty. Once I realized I was thrashing around fighting things entirely out of my control, I was able to find a well of peace.

  • Updating My Captain’s Log: In 2017, I began recording various things in GitHub in what I call my “Captain’s Log.” I keep public reading lists and annual commonplace logs. I just updated 2020 in case you’re interested in browsing.  

  • Annual Review: I’ve done an annual review for four out of the last five years. I skipped last year and wish I hadn’t. This year, I’m drawing inspiration from Jonny Miller’s Reflecting Forwards (paying for his template goes toward supporting his wedding—Jonny is a delightful person, btw)) and Steve Schlafman’s The Ultimate Annual Review(Steve is also a delight, and a fellow traveler on the coach path).

  • Upgrading My Camera Setup: As a coach, I’m now spending a lot of time on Zoom calls. Each session is deeply personal, but I felt like my camera left a lot to be desired in terms of creating an experience closer to sitting in a room together. Each session is “the product,” and I wanted to make sure clients got the best experience possible. So I invested in a new DSLR camera, and it makes a big difference. I created a post with my equipment here.


More Updates

Ask Jerry

In the last edition (October 28th), I announced Ask Jerry and shared a few excerpts of the first edition. We’ve now published four editions:

After edition three, we decided we needed to let the “Jerry Colonna on” headline format die and write better headlines. This paid off big time, with Edition four getting 12K reads vs. the next highest clocking in at 2.1K.

Total subscribers are a little over 3K after 6 weeks, which speaks to the power of the bundle the team at Everything is putting together. For reference, it took almost a year for Holloway’s Good Work to reach ~5K subscribers.

What I've Been Reading


  • Rhythm of War (Brandon Sanderson): I was giddy when the fourth installment of Sanderson’s fantasy epic-novel series, The Stormlight Archive, came out this November. I’ve been waiting for this one for more than a year.


“Anxiety is also evident in excessive time spent on tasks. Anticipating negative criticism from others means that every last detail of what could go wrong has to be exhaustively prepared for, not once but several times … Managers living in a mood of Anxiety find it difficult to develop a long-term strategic focus … they find it difficult to delegate, they micromanage, have a short-term focus and do not develop the resourcefulness of their people.” (Vol.
II, p. 272)

What I've Been Listening To

Things You Can Use

  • Flow: A lightweight work timer and website / app blocker to help you focus. You have to buy Pro to get the URL blocker, but it’s $0.99 / mo. or $19.99 for lifetime access.
  • Forest: Kate and I started using Forest together. Similar to Flow, it’s purpose is to help you focus. The difference with Forest is that it’s not really a work focus app. Instead, it incentivizes you to put your phone down. Kate and I love that we can put a timer on together while we’re having dinner or watching a show together.
  • Fantastical: I now have clients in four time zones, and keeping track of all four is a challenge. Fantastical makes it easy to switch between multiple time zones, whereas Google Calendar only allows you to display two time zones at a time. I also love the visual display for Fantastical, and I recommend it for anyone looking for a calendar upgrade.
  • The Chef'n Citrus Orange Squeezer: If you make cocktails or bake with citrus, this is a must-have for the kitchen. No lie. No affiliate code. Just buy this for yourself or your loved ones. This is legitimately one of my favorite purchases of 2020.
  • The Holloway Guide to Raising Venture Capital: Use this link to get 30% off. Disclosure: this is an affiliate code, but because I'm the guinea pig for Holloway, not because I'm trying to make a buck off you!


  • In Edition 4 (October 20th), I teased some information about a new podcast I was working on. In-between then and now, I named the podcast. It’s called Between, and episodes will live at between.fm.
  • The idea behind the show is that it will be a new podcast about relationships between leaders. My favorite way to pitch it is, "It's kind of like Guy Raz's How I Built This, but about the people and relationships behind the businesses and products.

How You Can Help

  • If you or anyone you know are interested in working with me as a coach. Reply to this email and let me know so we can set up some time!

  • If you, or anyone you know, would be interested in reflecting on your startup experience with an emphasis on the people instead of the idea for the podcast, reply or send folks my way!

  • How was this email? I know it was veeeeeery long. What did you like? What should I keep doing? What should I stop doing?

Looking forward to what’s next,