Boston: INBOUND Again

Second year in a row at HubSpot INBOUND. This time at the Omni Boston Hotel at the Seaport, which had the advantage of being directly connected to the convention center. You walk from your room to the keynote stage without going outside, which in early September in Boston doesn't matter (the weather is perfect) but which matters enormously for the five days when your schedule is back-to-back panels, meetings, and the speed-walking between rooms that conferences demand.

The Omni Seaport is a newer hotel, opened in 2021, and it feels like it. Everything works. The lobby is large and open with enough seating that it became an unofficial meeting spot for half the conference. The rooms are clean, modern, well-soundproofed (essential when you're sleeping in the same building as several thousand people who are networking until midnight). The views from the upper floors face the harbor, and watching the boats come in while drinking coffee before the morning session became my ritual.

I came straight from Vienna, which is a transition that deserves its own article. You go from sitting in a Heuriger courtyard drinking wine under chestnut trees to standing in a convention center hallway holding a lanyard and a lukewarm coffee, talking to someone about marketing automation. The whiplash is real. It took about a day and a half to recalibrate. G had flown home to Miami from Vienna the day before I flew to Boston, so we'd been together for three weeks straight and suddenly we were in different time zones with different schedules. The first night at the Omni I ordered room service and fell asleep at 8 PM, still running on Vienna time.

The conference was good. Bigger than the year before, or it felt bigger. The main stage production had leveled up. The sessions I spoke at went well. The hallway conversations were, again, the most valuable part. I'm increasingly convinced that the ROI of conferences is 20% content and 80% proximity. You can watch the talks on YouTube later. You can't recreate bumping into someone at the coffee bar and having a 15-minute conversation that turns into a partnership. I had a conversation with a founder from Austin on the second day that started with "I've been thinking about something you said on stage" and ended 45 minutes later with a handshake and an actual plan. That doesn't happen on Zoom.

Boston in early September is still summer. The harbor breeze keeps the Seaport comfortable and the light on the water in the late afternoon makes the whole district look better than it probably deserves. I ran along the harbor one morning before the sessions started, about four miles out and back along the waterfront path. The Seaport has that new-development energy where everything is clean and modern and slightly lacking in personality, but the water views and the running path along the harbor are excellent.

For food, the Seaport District has filled in over the past few years. It used to be empty waterfront and parking lots. Now there's enough to eat within a few blocks that you don't need to leave the neighborhood. I went back to Row 34 for oysters and beer, because it worked last year and I saw no reason to fix what wasn't broken. I also found Committee, a Greek restaurant near the convention center with a meze spread and grilled lamb chops that made me wish I had a longer dinner window. Most conference dinners happen in 45-minute gaps between sessions and after-parties, which is not enough time for Greek food. Greek food needs two hours and no agenda.

One evening a group of us walked to the North End, about a 25-minute walk from the Seaport through downtown and past Faneuil Hall. The North End is Boston's Italian neighborhood, narrow streets, fire escapes, old women sitting in chairs on the sidewalk watching the world go by. Giacomo's on Hanover Street was the pick. No reservations, cash only, tiny restaurant, line out the door. We stood outside talking about everything except marketing for 40 minutes, which was its own kind of therapy after four days of panels. The butternut squash ravioli in brown butter and sage is one of those dishes that's so simple it shouldn't be as good as it is. We ate in 30 minutes and it was worth the ratio. After dinner, Mike's Pastry for a cannoli, because you don't walk through the North End without one. The line at Mike's is always absurd but it moves fast. Lobster tail pastry is the sleeper pick over the cannoli.

The walk back to the Seaport after dinner, through downtown Boston at 10 PM on a weeknight, is one of those conference moments that stays with you. The city is quiet enough that you can actually hear your group talking. The Financial District is empty. The streetlights on the old cobblestone streets near Faneuil Hall look like they've been there since 1776, and some of them have. Someone in the group made a joke about the Founding Fathers and email marketing that was funnier than it had any right to be at that hour.

My last morning I walked to Tatte Bakery in the Seaport for a shakshuka and a coffee. Israeli-inspired bakery, excellent pastries, a place where you see people on their laptops at 7 AM and feel like you're back in a coworking space. But the shakshuka was great and the morning light through the windows was good and sometimes the last meal of a trip is the one that bookmarks it in your memory.

Five days. Spoke, networked, ate, walked, flew home.