Dear Stakeholders,
an update

I left Twitter five months ago; here’s where we’re at

So much has happened since last time.

The recent months have formed Phase 2 of unemployment, and as you remember Phase 2 is about

  • making exercise a habit
  • cementing family bonds
  • pursuing some personal projects
  • finding a job

I’ll update you briefly on progress in each area below.


I’m proud to say that I go the gym seven days per week, and exercise is firmly part of my routine. I even brought workout clothes with me on my current trip to San Francisco, which is a habit I’m nearly a decade out of practice with. Hotel elliptical, I’m coming for you.

I feel significantly better. I’ve still a good way to go but over the last 162 days I’ve lost 36lb — which, somewhat astonishingly, is the weight of my five-year-old daughter. With some disbelief I remember this fact each time I carry her up the stairs at bedtime.

Also! My buddy Rob loaned me one of his many fancy road bikes… and Rob has very good taste in bikes. First time in 25 years I’ve even had a bike with drop handlebars; first time in five I’ve had one with even gears or a freewheel hub. Exciting times ahead.


The very hardest thing about giving up unemployment will be spending less time with my family. I mean really:

The last five months has been an incredibly valuable demonstration of the things that matter most, and what lovely and loving times one can have if one can only make time for them. I’ve struggled with this in the past, and the reminder is timely.

It’s not lost on me, the fortune I’ve had to take these last five months to focus more on those I love the most. I plan to ensure I don’t lose this awareness and focus.

Personal Projects

I noted last time that my Pocket queue was still growing, and now it’s not. Best book I’ve read while unemployed? Traffic, by Tom Vanderbilt. Also noteworthy: Brad Feld’s Venture Deals (foreword by @dickc!); in reading it I felt like I’d gotten a solid education in the field.

I wrote up “Unusual Twitter Alerts”, finally.

I did a speaking gig in LA:

(I presented on “Hypergrowth in a Product Company”. AMA)

More recently I wrote @congratsbot on a lark but it’s actually been a pretty interesting lesson in many things (and thanks @rklau)

…not least of which the shame one feels in releasing code on Github as an utter dilettante.

Gaining Employment

I recently looked back on the last time I did this

and realized in retrospect that my goals, strategy and tactics five years later were — unconsciously — uncannily similar. And just like before I found myself looking for

  • a tech company;
  • a transformative product;
  • a kick-ass team; and
  • a strong top-down vision.

I spoke with many interesting folks in Boulder, and a handful elsewhere. A few cool opportunities crystallized, actually much more quickly than I was expecting — which, I guess, is a good problem to have. And along the way I discovered that the Boulder tech community is remarkably welcoming in a way which was equal parts surprising and delightful.

There was one company which stood out in particular, though, and so here I am today on my first day at Stripe, working as a Product Manager. I’m genuinely thrilled.

Looking forward

I’ll be staying in Boulder, working mostly from home, but traveling to San Francisco regularly to be at Stripe’s HQ.

Expect brief updates on Twitter, and a few longer ones here.

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