11 / The story behind my latest project, Hoo Boy.

Welcome to Issue #11!

Captain's Log: October 23, 2022, San Francisco, CA, written entirely by a human.

The star of this issue is my latest project: Hoo Boy. It’s a newsletter I send every other week where I write for founders navigating how to manage (1) themselves, (2) their team, and (3) their company. If that sounds fun, sign up here or read an issue here.

Two newsletters from one person might be confusing, but I’m keeping Captain’s Log and Hoo Boy separate. Captain’s Log is personal (and sent ~2-4x / year), and Hoo Boy is about my work (and sent 2x / month). Sometimes there will be overlap, but I figured folks would prefer to opt-in to something sent more frequently.

One of the main reasons I write Captain’s Log is that I think people dig reading an honest perspective from someone trying to figure out their life and career. So, below, you can read about where Hoo Boy came from and why it’s something you can count on to stick.

Where Hoo Boy Came From

I began coaching founders in the summer of 2020. I immediately found that I loved it and was pretty good at it. But I’ve felt like something is missing in the two years since. It was like nachos without tortilla chips, Oreos without the cream filling, a Rick without his Morty. These things are all good, but they’re incomplete.

I’ve been trying (and failing) to fill that void with creative stuff ever since, so when I felt stuck again in April, I slowed down, zoomed out, and took everything I’ve learned about helping clients and applied it to myself. And it turns out the stuff works.

My biggest insight was that I needed to find a topic that I found so interesting that it could readily compete with just about anything else for my attention and win. When studying the research on human motivation, Dean Keith Simonton (Greatness, p. 141) wrote:

“…we might do better to say that all the motives that can stimulate the energies of the human being all converge on a single activity, a monomaniacal preoccupation.”

The normal-person language version of this is probably “obsession,” but obsession calls to mind the lady in the Starbucks line talking too loud on her phone, “Oh my god, I am obsessed with oat milk.”

To be monomaniacally preoccupied hits different. If there’s a spectrum from 0 - 100 of how monomaniacally preoccupied you are, at 100, you’d always choose to spend time on that thing over your family, friends, Netflix, exercise, or anything else. I think my optimal level of preoccupation is north of 50 and under 100—the thing would be able to compete (and win) most of the time, but I wouldn’t be a slave to it.

After some digging, I found that almost all the work I’ve loved doing the most has to do with understanding how people effectively organize to solve problems for other people in a way that doesn’t suck for the people involved. Some people might call this “management,” but it’s probably “management that doesn’t suck.”

I keep coming back to this topic for at least two reasons: one from watching my Dad work as I grew up and one from my own experience starting and building companies.

First, I grew up watching my Dad come home from work in a foul mood that made it clear “work” must essentially be Mordor, and I’d later listen to him advise me to choose work I’d enjoy. To some extent, I want to save all the parents and kids from stress, dark moods, ensuing arguments, and so on. To call it easing suffering feels dramatic, but that’s what it is.

Second, I’ve started three companies and coached more than 30 founders. Quitting your job, coming up with an idea, and getting product-market-fit (”PMF”) is hard enough. But after a founder gets PMF, they have to become reasonably competent in an uncanny number of new areas and skills in a short period or face the market’s gallows.

They have to understand the essential functional components of a business: sales, marketing, finance, engineering, product, operations, and more. But wait, there’s more: learning about performance management, hiring, firing, handling gossip, interpersonal conflict, time management, planning and retrospectives, and structuring meetings is a lot.

Now, management that doesn’t suck is something many of people could get interested in, but if I’ve learned one thing from my experience founding companies and coaching others, it’s that a broad audience may as well be no audience. So instead of starting with an ambition to create a grand unified theory of management for all millennial managers, I’m starting with the folks who’ve taken the leap to start their own business and have self-selected into being willing to try their best to learn whatever they need to for their business to succeed.

Hoo Boy is where I’ll be writing about that journey, and while I have other aligned project ideas, I’m going to let those marinate for a bit longer before sharing anything about them publicly.

Why You Can Count on Hoo Boy Not to Disappear

To learn from past experiences, I did two things differently with Hoo Boy. First, I slowed myself down after feeling “ready,” making myself wait two months before getting started to make sure my whole heart was in Hoo Boy. Second, I made sure I was committing not just to start the newsletter, I was committing to publishing for at least a full year.

I’ve quit a lot of stuff, and I wanted this newsletter to be different. All three companies I started, I quit. The first, I quit after a year. The second and third, after four years each. And since the third, I’ve started and stopped several projects after only a few months.

When I looked for patterns, I discovered that when I find myself in-between projects, the anxiety of doing nothing leads me to rush into something my whole heart isn’t in. Months (or years) later, I inevitably decide to be honest with myself, and then I quit.

The most interesting part is I always knew the thing wasn’t right for me really fast after committing, but then I couldn’t get over the sunk costs and summon the courage to call it quits.

So this time, I put myself on pause when I felt “ready” to get started on Hoo Boy, redesign my website, announce the thing, and write the first issue. I committed to waiting two months before writing my first issue. If I were still excited on July 15th, I’d have passed the period where I’d usually have realized I’d committed to something halfheartedly, and it was safe it proceed.

The other insight I had was that it’s really easy to start something if you think of it as an experiment, and that’s a good thing. But this time, I didn’t want an experiment, I wanted something I could commit to and others could rely on. So instead of committing to start writing a newsletter, I committed to publishing it for an entire year.

So that’s a long-winded way of saying this thing ain’t going anywhere, at least for the year. But so far, I’ve been lovingwriting it in a big way, so I anticipate it will go on much longer.

The first issue went out July 24th, and issue eight goes out next Sunday. Sign up here.

Major Events

  • Summer Vacation: In July, I took two concurrent weeks off for summer vacation for the first time since grade school (and even then, I worked 40+ hours most of the last few summers). For the first week, I flew out to Columbus, Ohio, a full week before one of my best college friend’s wedding. I caught up with a ton of old college friends who I hadn’t seen since before the pandemic. After that, Kate and I visited her family in New England. But the best choice of all, I think, was to come back home on a Thursday, so I still had a three-day weekend ahead to settle back in.


  • Hoo Boy: I already told you about this in the preamble. So sign up!
  • Continuing Education: I came across the word philomath a few years back. It means “lover of learning,” and it continues to resonate. There are three big areas I’ve spent the last six or so months learning more about: design (I do all my graphics & website), writing, and management. Some books I’ve been making my way through: Greatness, Grid Systems in Graphic Design, Quit, The Ancient City, The History of Management Thought, The Managerial Grid, and A Game Free Life.
  • Being a Better Boyfriend: Kate and I crossed our three-year anniversary this July, and we’re both big believers in actively investing in learning how to be better partners. We recently found it helpful to learn more about attachment theory through Dr. Sue Johnson’s ******Hold Me Tight. I also continue to find Ester Perel’s belief that when couples argue, it’s almost always about one of three things: (1) power and control, (2) closeness and care, or (3) respect and recognition.
  • Blue Dot: In 2021, I announced a new brand for my coaching work, Blue Dot. I went all in on becoming “the climate coach.” I was hot off of seeing the sky turn Blade Runner orange in San Francisco, reading apocalyptic climate fiction, and I was really enjoying working with a couple of clients addressing climate change in some way. In retrospect, I went all in too soon. It’s not that I suddenly don’t care about Climate Change (I do). I continue to work with several climate-focused founders, but folks continue to introduce me to great founders outside of climate, and it feels strange to say no if I feel like there’s a fit. On top of that, while I enjoy my work with climate founders, I’m drawn to learning and teaching about management more than I am to do the same for climate. So I’ve decided to sunset the Blue Dot brand and keep all of my work on andysparks.co.

Top 5 Recommendations

  1. The Realm of the Elderlings Series by Robin Hobb: I’ve spent the last year reading all twelve books in this series. Twelve books are enough to make most people say, “Aw hell naw.” But Robin’s broken the series up into four trilogies, each of which I turned through faster than a ten-year-old powering through a new Harry Potter release the day it came out. I genuinely spent an entire hour-long bus ride crying as one of the trilogies wrapped up. The series follows Fitz from boyhood to old age in a world with mysterious magic, realistic politics, wonderful friendships, and characters you won’t forget. This is now my favorite fantasy series of all time.
  2. Lex—AI Powered Writing Assistant: Last week, my friend Nathan DM’d about a “thing he was coding” to get some feedback. Turns out, that thing turned out to be a basic but cleaner version of Google Docs with a GPT-3 integration to help you get unstuck when you’re writing or brainstorming title ideas—check out the demo here. Nathan’s went from launch to having his logo on Sequoia Capital’s Generative AI Market Map in under 24 hours, so needless to say, the hype is real with this one. But having given it a shot, it’s one of those things that, after you use it, you say, “Of course this was going to exist.” And I look forward to seeing it get better.
  3. Grapefruit + Mangosteen Candle: I’ve no idea what mangosteen is, but what I can tell you is that this candle smells incredible. Our downstairs neighbor had been burning it last month, I asked about it and immediately bought one from the shop down the street.
  4. Smart Brevity: If you’ve ever read a newsletter by Axios, you’ve seen Smart Brevity in action, as it’s their methodology for writing in a way that captures people’s attention. I decided to pick the book up and give the style a whirl in my last issue of Hoo Boy, and I found it was a helpful way to keep myself honest about whether I was filling my writing with fluff or not. At a minimum, it’s a helpful companion for anyone interested in becoming a more succinct and clear communicator.
  5. A Travel Bag for All Your Cables: When I travel, I bring my phone (and cable), my Kindle (and charger), my battery pack (for my phone that doesn’t hold a charge), my AirPods, my watch (and charging cord), and so on. My backpack used to be a mess of cords, usually some missing. I saw a buddy had this bag for his cables on a trip in May and decided to get one for myself and pre-stock it with all the cords I need for travel so I’d never have dead batteries again. Top 5 summer purchase.


  • New Coaching Slot: A client of mine recently “graduated,” and I have a new slot opening up in November. If you know any founders who are at or near product-market fit, looking for a coach, and loves the learning process, I’d love to speak with them. You (or anyone else) can learn about my coaching here.

That’s all for this week. I’m looking forward to what’s next!