Book Update #3: Married Twice in One Week

Hey everyone,

One year ago this week, I got married twice.

Literally. I married my beautiful wife Jess on June 28 in London, and officially sold UpdateAI to Gainsight on July 3. A fun story that epitomizes the life of a founder — and our destructive relationship with any attempt at work-life balance:

It was 11PM London time the evening before our wedding. Jess and I were just about to practice our first dance for the next day ("Stand by Me" by Ben E. King). We'd tried six weeks earlier to take a first-dance lesson at the Fred Astaire studio near our apartment in New York, but the instructor just laughed and told us couples usually start six months in advance. So there we were, practicing for the first time.

Then I get a call from our UpdateAI M&A advisor — which I was somewhat expecting, because I knew Gainsight was holding its Q2 board meeting that day, the one where our deal was meant to be officially sealed.

"Hey Josh, it's Peter. Their corp dev called and told me everything went to plan." Then he paused. "There's just one little thing — I truly don't know what it is, and the Gainsight team knows you're getting married tomorrow. They don't want to disturb you, so they say you can catch up about it on Sunday."

And that, verbatim, is what hung over my head during my wedding!

The issue turned out to be benign — in fact, something I was happy about. We had the legal Zoom call to officially sign off on the deal as I stepped outside Dal Bolognese restaurant in Piazza del Popolo, on our honeymoon in Rome.

A year later, I can laugh about it. It's also a fitting preview of what I've been buried in this month — the chapter on founder burnout. More on that, and where the whole book stands, below.

We've now crossed the 50 founder interviews threshold. Since my last update I've had the pleasure of speaking with:

And yet those interviews actually represent a deceleration of my research phase as I've been focused on writing one chapter draft per week.

One chapter per week may sound simple; it is not. I dropped a previous writing program that wasn't serving me and have started working with a new coach named Lori Lynn. She's fabulous and she is making sure that the book stays human. Her overarching guardrail (an ironic word to use these days) is that it reads as though I am speaking one-to-one with someone I'm having coffee with. We are now at 20,000 words of the manuscript (i.e. first draft) and six chapters — including the burnout chapter I finished this month, the one this whole opening story is really about. The book aims to be 50,000–70,000 words and 15–20 chapters. I'm slightly behind pace, but that's okay.

This includes two versions of the intro after this alternative version popped into mind the other night and felt too raw, original, and fun not to write up: Eat Shit Alternative Intro. Feel free to leave your best comments on it!

One lesson that stands out from a recent conversation:

And I realized it's something I naturally do pretty well, too. Some of you may have even received a "Happy Father's Day" text message from me on Father's Day as a result of that lesson, reinforced by Alex.

This week I started writing the chapter on "maintaining healthy co-founder relationships" but then I put it aside. It's such an important topic and I think my content is still a bit thin on it. If you have anything you'd like to share about this topic, I'd love to hear from you. In particular, if as a founder you've had a recurring ritual with any of your co-founders as a way to maintain the health of your relationship (e.g. Danny Wen and Shawn Liu's Tuesday breakfasts while running Harvest).

The pace is frenetic. My Sundays have become full bore writing days (goodbye Summer). But I'm still having so much fun. And really excited by how the stories are turning out.

As always, thank you for being part of this journey.

— Josh