Thoughts on startups by investors that
fund them & entrepreneurs that run them

If you could work at any startup in New York City, where would you choose and why?

Well, I’m biased, but let me just describe yesterday’s Summer Outing at Gust:

For background, you should know that by long-standing company tradition, our outings are surprises. And that means a complete and total surprise to everyone, as in “not a single person knows a single thing about it in advance”…except for the CEO, who personally sets everything up, from designing the t-shirts to chartering the buses.

So all that anyone on the team knew was that they were supposed to show up at 9:00 am at the Bayview Correctional Facility.


At 9:00 am precisely, instead of entering the prison, we did an about-face, learned (while passing by) about both the hidden Venus mural on the prison’s wall, andEdward Tufte‘s gallery showcasing his seminal book The Visual Display of Quantitative Information, and proceeded across the street to Chelsea Piers.

Once there, we found awaiting us a full buffet breakfast, and a sign-up poster for the morning’s optional activities, from which everyone got to make multiple choices from among golf, bowling, massages, rock climbing, sand volleyball, a brewery tour/beer tasting, and a super-cool tech-company tour:

At 12:30, the group reassembled and set off for a walking tour of ‘neat things along the Hudson’, including Hudson River Park, a lightship, a fire boat and a caboose, and then followed the train tracks from the Hudson rail barge inside a building, through a restored terminal warehouse, and then across the street past the McKittrick Hotel (the home of Sleep No More.) Rounding the corner, we were met by senior executives from the High Line, who took us up into the park for a VIP guided tour:

At the end of the High Line at Chelsea Market, we found box lunches waiting for us at Terroir Restaurant, and had an hour of free time to relax and enjoy lunch and the park. At that point we descended from the High Line to find a bus waiting, which took us down past the Freedom Tower to the marina at World Financial Center, where we boarded the yacht Shearwater:

With a spectacular day and a brisk wind, our team received a seafaring lesson from the crew, helped haul up the sails, and away we sped for an exhilarating five hour sail out through New York Harbor past the Verrazano Narrows Bridge to the South Bay and the Gateway National Recreation Area.

In the late afternoon, after several hours of deep conversations, dozing on the deck, and making new friendships (our coding teams, bus dev folks and interns don’t see too much of each other during the work day), we sailed back at a leisurely pace as we enjoyed a sumptuous buffet dinner on board.

Finally, as the sun touched the horizon in the West, we sailed home by way of Lady Liberty, in awe of how lucky we were to be living and working in the world’s greatest city, with amazing teammates, doing amazing things:

And that was just yesterday!

*original post can be found on Quora @ *

Written by David S. Rose

user David S. Rose Founder and CEO,

David has been described as "the Father of Angel Investing in New York" by Crain's New York Business, & a "world conquering entrepreneur" by BusinessWeek. He is a serial entrepreneur & Inc 500 CEO who chairs New York Angels, one of the most active angel investment groups. David is also CEO of Gust.

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