Good Work №8

Andy Sparks
Mar 24 · 4 min read

This week’s soundtrack: 🎶 Ballad of the Beaconsfield Miners by Foo Fighters

>> Good Work is a hand-curated newsletter by Holloway devoted to exploring how each of us choose to spend the 90,000 hours that will make up our careers. Not getting Good Work regularly? Click here to subscribe!

Our brave hero prepares to face the world of work.

“One of the few appealing things about him was that he had figured out that his personality was a problem and, in classic ‘get it done’ style, had hired a coach to make him less of an asshole. She could see that working in his face.” — Neal Stephenson, Seveneves (p. 119)

Tyler Lyman, a new Good Work subscriber, wrote us on Monday asking if we had plans any time soon to explore the relationship between startup founder and executive coach. I hadn’t decided what to write about for this week’s Good Work yet and thought tackling the subject would be a breeze — my co-founder, Josh, and I happened to be headed in to see our coach the next day.

Inspired, I dashed off my thoughts on how working with our amazing coach, Christina Harbridge, has been one of the most valuable professional experiences in my life, when Josh pointed out that most people — even those who can afford it — don’t ever get a therapist, let alone a professional executive coach.

“Are coaches like having a butler or a gardener — things certain rich people have but only because they have a mansion or a big estate?” he asked.

While not quite like having a butler or a gardener, Josh was of course right in pointing out that access to executive coaching is a privilege. In that moment, he also acted as a great coach to me, showing me a blindspot but not making me feel ashamed of it. The best coaches, whether they’re a paid executive coach, a parent, or just a friend who listens earnestly over a few pints, perform the same function. Put one way, “A coach is someone who can give correction without causing resentment.” (attributed to John Wooden, source unknown). They’re there to help you be successful, and to do this they tactfully help you become aware of behavior that’s impeding your goals.

While coaches can be valuable regardless of your position in a company, they can be immensely valuable to CEOs, as the nature of their role leaves them without a manager to mentor them. If you’re calling the shots on whether you or someone on your team gets a coach, think about it as an investment, not a one-time cost.

Growth necessitates a trail of trials — you must always be starting over, learning new things, and true mastery requires the wisdom of knowing that nothing can ever be truly mastered. In addition to acting as a mirror for you to see who you are and the path to becoming the person you need to grow into, coaches can help soften and shorten the cycles of repeatedly being bad at things.

This Week


Aside from my coach, Christina, I’ve had the privilege of spending time with Jerry Collona and Khalid Halim of Reboot. All three of them are absolutely delightful people. I also frequently refer to parts of executive coach Matt Mochary’s book, The Great CEO Within (available as a free Google Doc here).

  • [15m] Wired’s profile on Jerry Collona, This Man Makes Founders Cry, by Jessi Hempel, will give you a close look at the man who has worked with the likes of Etsy CEO Chad Dickerson and Gimlet Media co-founders Alex Blumberg and Matt Lieber.
  • [16m] The Science of Speaking is the Art of Being Heard, a piece about Khalid Halim of Reboot in First Round Review, unpacks several of Halim’s favorite frameworks and tools he uses when working with his clients. After re-reading this piece this week, I think I’m going to setup a reminder to frequently refer to it.


  • [6m] A transcript of a short podcast with Naval Ravikant, Play Long-term Games With Long-term People is a great distillation of a principle I’ve applied at conferences ever since I met Danielle Morrill at SXSW in 2010: meet one person who I believe I could be friends with for more than ten years.
  • 🎥 [27m] Eight years later, I met Michael Shearn at a conference using this method, and I had the privilege of spending several days with him last week in Austin. Michael runs an investment firm where he focuses on doing an immense amount of research on the CEO before investing. He’s a fascinating guy, and you should watch this interview with him (transcript also available on the page).
  • [24m] On a similar thread, I’m constantly looking to learn from leaders who don’t fit the Silicon Valley mold. This interview with Brunello Cucinelli by Om Malik is full of ideas about running a business that you don’t hear in Northern California. Thanks to Julian Targowski for pointing this one out.

That’s Good Work for this week. Looking forward to what’s next.

Andy and the Holloway Team

>> Good Work is written and curated by Andy Sparks with help from Courtney Nash, Dmitriy Kharchenko, Hope Hackett, Joshua Levy, and Rachel Jepsen.


Insights and thoughts from the Holloway team.

Andy Sparks

Written by

I like my beer cold, conversation challenging, and work fulfilling. Aún aprendo. Buckeye. Current: Co-Founder & CEO, Holloway. Past: Co-Founder, Mattermark.



Insights and thoughts from the Holloway team.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade