As East-Coast based founders (albeit transplanted from sunny Southern California to Vermont and New York City), one of the most productive rhythms we’ve established over the years is a founder’s trip.
While a good founder’s trip can take us anywhere, it mainly means one thing: West Coast! And one of the great things about Silicon Valley and San Francisco is that folks are willing to meet up, even if they barely know you. It’s part of the DNA of the place, and I love it.
Our trips got started in 2015 when Zac and I were fundraising for Packet. Bare metal was a tough sell to Sand Hill Road at the time (we got dozens of passes for our Series A), but fundraising was never the only activity. We spent most of our time with customers, partners, silicon providers, and visiting our SJC1 datacenter (plus the In-N-Out nearby) and filled in the gaps with the great folks at Dell Technologies Capital, Third Point, SoftBank, Samsung Ventures, and others.
Now that we’re building Datum, we’re back in the Founder’s Trip habit. So how does it work?
First, it’s my job to look ahead a few months, map out schedules, and put holds on our calendars. No easy task! In fact, it’s amazing that it ever works out between personal stuff (college trips, holidays, nonprofit board meetings, community orchestra performances, etc) and East Coast requirements (we host meetups in Boston and NYC). If I’m able to line trips up with notable conferences, industry events, and business milestones (product, fundraising, board meetings, etc), then I know I’m on the right track.
This year I planned out October (5th-9th), November (2nd-5th), and December (7th-10th) all at once. I’m about to be locked in on March, April and May for 2027.
Clearly you can’t plan everything in advance but I have found that rhythm matters more than basically anything else. If you get something in Zac’s calendar early enough, you have a shot.
The next step is always the same: dive into a Google doc (tabs are super helpful) and start stubbing out potential logistics, including flights, Airbnb location, and where to focus each day (the Valley vs downtown). We usually stay near the airport for maximum flexibility.
After that it is an exercise in brainstorming and playing Tetris, with me running point and Zac feeding things my way (usually looping me into an email thread or group text chat).
- I tend to lock a few things in and send calendar holds, knowing they will move around
- I group multiple meetings at the same coffee shop
- I put a happy hour and a small dinner on the books, scooping folks into each of those
I’ve learned not to be too ambitious with geography (especially in the Valley). Don’t move physically around more than you have to!
Above all, our secret strategy remains a willingness to divide and conquer. Inevitably meetings move around, new opportunities crop up at the last minute, or customers have more important things to do. I’m fortunate to have a co-founder / brother I can tap in or out as needed, and while we try to do meetings together, we end up splitting the schedule at least 30-40% of the time.
This past week we were in Las Vegas and San Francisco. By my count we met with just over 30 distinct companies. Not bad!
