Photo by Stephanie Hau on Unsplash
In 2018 Dan Berger sold Social Tables, a SaaS business, for $100M. He didn’t know it then, but since his entire life was the business, he “lost” everything when it sold and inadvertently began a journey that led to a book, then to his current business, Assemble.
Dan started a side business that was a wedding seat chart app. It started over anxiety about an upcoming wedding he was invited to and he wondered who he might be sitting next to. Eight years later, the app was generating $20M in recurring revenue across 6000 customers.
The app had started as a B2C play, aimed at brides at a cost of $49, but pretty quickly, Dan saw that wasn’t the play and moved to selling to wedding planners and ultimately to hotels. As a generalist, he felt he had the competencies to keep guiding the business forward on all fronts and so really only wanted money rather than technical help when he went out for raises. He got $8M in a Series A and another $13M in the Series B.
By the time he went to market to sell the business, he only held about 20% of the business, but the business commanded 5X revenue, which meant that some of the institutional investors saw a 2.5x return on their investments and some of the angel investors saw 14x. 20% of $100M meant that Dan walked away with roughly $20M, though some of that was tied up in his working for a couple years for the new company, and he left before completing the second year, leaving about $1M on the table. Convinced he was a builder and not a worker bee, he couldn’t stay any longer.
Indeed, Dan was already gearing up to buy Meetup.com, which was being divested by WeWork. One of the investors got cold feet, and the deal collapsed shortly before Covid, and instead of “going on to the next thing,” as many entrepreneurs do, Dan had to sit, as many of us did, during Covid.
During and after Covid, Dan sought consolation in drugs and meaningless relationships. He had built a socially oriented business, but while doing so, he had built his own social life into the business. His best friend was a co-founder; he enjoyed the accolades and handshakes at conferences and media events, and every day, he enjoyed interactions with the various members of his team. All that came to a screeching halt when he exited, and he had no family, relationships, children, or peer group to fall back on.
He did eventually find his footing, going on to write a book called The Quest, which addressed what had happened to him after the exit: he had lost a sense of belonging, which Berger claims all of us need, no matter where we are in our lives. That sense of belonging, as well as his experience in helping to bring people together in Social Tables, led to his current venture, Assemble, which is building retreat centers around the US. “I may not cure cancer,” Berger opines, “but perhaps I can create a space for someone who does after connecting better with his team and those that matter to him.” The flagship location in Boise opens on November 1st.
Perhaps his most interesting take post-exit is the disdain he has for founders who immediately move on to a project post-exit. “It’s like finishing a meal and then going to another meal right afterwards.” To Berger, such a move doesn’t really take account of all that has happened: he wants founders to hold space for the journey that has just ended before jumping into something new.
Key Lessons
Dan Berger leaves us with some unusual takeaways:
- What starts as a side hustle can turn into a nine-figure exit. Don’t be dismissive about how much a business can grow if you put the proper time and energy into it.
- Even as you systematize your business, don’t underestimate the sense of belonging you gain from operating it. Prepare yourself for that to end.
- Question assumptions: Does it really make sense to “go on to the next thing” right as a significant chapter in your life closes? Perhaps taking some time for yourself will make that next chapter that much richer and more significant.
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