bookspersonal development

Summa Read, Summa Listen

It’s been a bit, but I promise I’m not asleep… and my brain has also yet to “turn to mush”, as one PE guy asked me recently. I guess everyone just expects you’re playing Xbox all day when you have a home office.

This summer has been active with exec coaching and a mixture of leadership changes, fundraising and exec hiring across the handful of organizations I’m involved with. My favorite moments have been the moments where everyone is learning or contributing together and it’s clear the teams I’m focused on are growing themselves.

Remember, my wife and I also have 5 kids under the age of 12, who have been delightfully underscheduled and home. So I took a moment (July) to be as fully present with them and my wife as I could be. I gave myself permission to just “be”. (Thanks, Jerry Colonna.) My favorite family moments have been the moments where everyone I love is experiencing the joy of doing meaningful things (growing?) together.

I do notice that none of my favorite moments happened solo, but it bears mentioning that I found myself alone, but content, at least half of the time.

A younger me would have sought to fill that time with people, external stimuli and moments of entertainment or extroversion — but this version of me was perfectly fine thinking, learning or discovering on my own. I believe that’s the byproduct of the last two years of recalibration and an increased comfort with my current blend of focuses (work, family, self-development). It’s no longer one “scoreboard” to rule them all. Everyone is (hopefully) better with me, but no one is going to die or go out of business without me… and to be fair the latter was probably never the case. Funny, how a little bit of space and perspective can go a long way.

So while I kept my cadence steady with my current work, I did say no or not yet to most new opportunities. I think 90% of them will still be there when the kids are back to school and it’s cold and dark in the Northeast afternoons again — or I may have crushed the top of my funnel for new opportunities. If I’m writing about sweat pants vs. joggers this winter, we’ll know that the funnel had a shorter expiration date than I thought.

One of the things I found most enjoyable this summer was how great good weather, a fire and the overlay of crickets pair so wonderfully with learning in book and podcast form.

Here is a list of some of the best of what I’ve been consuming with a little extra texture.


Trillion Dollar Coach (Eric Schmidt) — I continue to be a leadership geek and read leadership geek stuff even while I “grandparent” (advise) other leaders and companies. And, while many trite leadership books articulate differently named solves for the same universal and recurring people patterns we see everywhere, “Trillion Dollar Coach” beats that baseline. Bill Campbell died in 2016 after being the CEO of Intuit, but more interestingly he was the CEO whisperer for so many of tech’s Mt. Rushmore. From Jobs to Zuck to Google, he was unorthodox in his approach and seemingly as loved as he was effective. This will probably be my holiday book this year. Go snag it.

Reboot (Jerry Colonna) — Jerry’s book made me appreciate how simple my life and leadership journey have been comparatively. He’s had a wild and sometimes surprisingly rough ride. It’s also one of the more introspective and inwardly focused reads from the leadership and exec coaching catalog. Jerry believes there is no paint-by-number path to transition from founder to great leader or CEO — the only way to do it is to look inward, understand what’s misaligned about yourself and strive to actually become a better human being. He also spends a lot of time unpacking what he believes drives the irrationally ambitious entrepreneur, which — *surprise, surprise* — all center on the things that were most difficult for us when we were young people. In short, if you don’t know yourself and what drives you, how do you mitigate your blind spots or have any hope you won’t project your “issues” onto your team or decision making. A few years into RevZilla, I took an inventory on where I sucked as a leader and manager. After wincing my way through the feedback, I worked on those things and everything got easier or improved. Seriously, everything. I didn’t enjoy this book as much as “Trillion Dollar Coach”, but I still recommend it, especially for first-time founders scaling their teams and themselves.

The Fifth Risk (Michael Lewis) — Non-fiction, fascinating and terrifying. If you want to understand more about how the government, its departments and programs actually work to protect us from things we haven’t imagined but could wipe us out, this is the read. It also focuses heavily on how each new presidency handles (or doesn’t) the transition of leadership of these government agencies without threatening the efficacy of programs in place protecting our country.

Secrets of Sandhill Road (Scott Kupor) — I’m not a VC, but I read a ton of VC. I’m always fascinated by this tiny industry and group of people that essentially serves as the R&D for our global economy. Look at a huge percentage of the growth in the S&P over the last 2-3 decades and how many of those companies have been backed and grown by venture capital. There was a book by Brad Feld called “Venture Deals” that came out about decade ago and accurately reflected the VC climate and the mechanics of the typical deal and VC-backed company life cycle. I’d consider “SoSHR” the successor read. It’s more timely and less dry from the perspective of the founding CFO of Andreesen Horowitz. It moves fast and Scott’s wit and personality come through even as certain elements can be very dry as topics on their own. Based on my experiences with RevZilla and goPuff, I actually started at the end of the book focusing on later-stage companies and M&A to compare notes. I then circled back and completed the read. A must read if you are a founder thinking about raising capital.

Never Split the Difference (Chris Voss) — Recommended by a buddy in YPO (thanks Andy L.). I haven’t finished it yet but it’s another quick read. Written by a 30-year FBI hostage negotiator who challenges academia on their premise that rational outcomes and cost / benefit are the basis of good negotiating. This book is all about behavioral psychology, our “lizard brain” and how to disarm and build rapport to find productive resolution with even the most confrontational of parties. I’m a third of the way through this and nearly everything I’m reading could be used in a hostage negotiation, with a management team or with my kids at bed time. Universally useful.

Side Note – I don’t read for entertainment, my goal is typically to learn something. I’m “investing” my time with the expectation of growth. So I don’t audiobook as I find that I lose focus and will not retain nearly as much as if I read something with focus. If I’m listening, I’m “snacking”. Hence the list of podcasts below.


a16z — Andreesen Horowitz is only getting better and more useful as a platform to serve companies and entrepreneurs in all areas in the tech and startup ecosystems. What started as 30-minute podcast deep dives on a mix of interesting and diverse topics has now also increased its frequency to cover weekly happenings from their sphere.

Pivot — Galloway and Swisher can be redundant at times but the focus is typical big tech, current events and politics on a week-to-week cadence. I do love the absurdity, ranting and intellectual horsepower of the “big dog” (Galloway) although Pivot still won’t ever fill the shoes of L2’s Winners and Losers during its heyday.

How I Built This — NPR’s series of deep interviews with founders of merit from a diverse set of companies. Typically entertaining, insightful and introspective. My short list of faves: Nolan Bushnell (Atari), Marc Cuban, Mike Dubin (Dollar Shave Club), Andy Dunn (Bonobos). Did you know Chuck E. Cheese, founded by Bushnell, was originally called “Rick Rats Pizza”?

Happy summer people. I hope you are in rhythm and kicking ass.


Back to top button