Taking Over a Beloved Business: Dan Perry and Michael Serapiglia
Updated: 4 days ago
Dan Perry and Michael Serapiglia did not set out to buy a company. Dan had lost his job at an LGBTQ+ travel company and wrote to others in the industry asking for work. One reply came from Dan Ware, who had run Toto Tours by himself for 35 years and was ready to retire. He asked if Dan wanted to take it over. Michael's first answer was to pump the brakes. A few conversations and one riverboat trip in Belgium later, they said yes. Their story speaks to any owner taking over something loved by its customers. How do you keep what made it special, reach new people, and grow your impact while staying intentionally small? Their napkin offers a hint. If you get lost, enjoy the view around you.
Inspired by Paper Napkin Wisdom Episode 319 with Dan and Michael.
Why getting lost can be the best part of the plan
The napkin came from a trip to Venice. Michael and Dan were trying to find one place, got turned around, and chose to stay off their phones. They stopped and asked themselves how they could be lost just because they had not found what they were looking for. So they got a coffee and enjoyed the view.
That changed how they travel. When you are lost, you meet people you did not expect to meet. You find shops and restaurants you would never have seen. Michael describes walking up to a local, asking if they speak English, and striking up a conversation.
Dan has always been this way. As a kid he left the hiking trail to explore caves and see what was around the next corner. Now, on most trips, they ask where they are going to get lost today.
I noticed how close this is to their own path into business. Dan was looking for a job, one thing led to another, and he liked the view.
How to decide whether to buy a business you never planned to run
Running a company was not Dan's first choice. He did not think it was his cup of tea. The more he talked it over with Dan Ware and with Michael, the more it looked like a path that would let them live the life they wanted, travel, meet people, and keep the business small.
Michael needed more convincing. Buying a business seemed a little crazy at first. What moved him was time. Talking with Dan Ware, talking with Dan, and letting the thought sit until it started to make sense.
The real test was experience. Dan Ware had space on a tour after some cancellations, so they joined a riverboat trip in Belgium. They may have been the only first timers on board. Everyone else had been on at least one Toto tour, and some had been on 15 or 20. Sitting in the small hot tub at the front of the boat, Michael asked Dan if they could do this. Dan said absolutely.
Friends also asked a fair question. Did they really want to put both of their livelihoods into one project? It gave them pause. They went ahead partly because each has other work. Michael is a makeup artist and an artist first, and plans to keep that career going alongside the tours.
Can you grow your impact while staying intentionally small?
Dan had worked for a company that runs large charters for thousands of guests. On a ship that size, you rarely get to know anyone. What drew him to Toto Tours is that it is intentionally small. Everyone gets to know each other, which is how the family feeling grows.
That does not mean standing still. Dan is clear that they want to grow. Some longtime guests are ready to stop traveling, and a roster that keeps shrinking is not a business. Dan Ware built Toto Tours almost entirely on word of mouth. Dan Perry had never heard of it before he wrote to him. So the first lever is reach, through technology and social media, so people find the company when they are ready to travel.
The second lever is width rather than size. They want more tours and more trusted hosts. Dan Ware has had past guests come back to lead tours, and they plan to build on that. More tours, same intimate scale.
How to honor a founder's legacy while you change it
Loyalty runs deep here. Some guests have taken 10 or 22 tours. Friendships formed on trips years ago are still traveling together. Dan Ware's mailing list is a community.
Dan Perry does not want to copy and paste what came before. He likes the style Dan Ware created, focused on people who want to learn a culture and immerse themselves in it rather than sit by the pool with a bottomless drink package. He is open to a theme night here and there, but the trips stay small.
Michael frames it as homage. The LGBTQIA+ travelers of 35 years ago had to be very careful about where they went and how they presented themselves. Dan Ware learned how to take people safely to places where there are laws against them. That knowledge is part of what they are inheriting.
He had planned to shut the company down after one final trip. Dan's email gave him another option. In their words, he made a safe space for people who might be afraid to come out fully, who were shy, or who were traveling solo. That is the thing they are trying to carry forward.
Why testing new ideas light beats changing everything at once
Their new ideas came from listening. Over one summer, while talking with friends, acquaintances and strangers, one comment came up again and again. Some people did not want to go on LGBT trips because those trips were not sober.
That led to a series idea. Health and wellness trips that stay sober. Then adventure trips, such as a bike trip or a climb of Mount Kilimanjaro, researched carefully for injury risk. Then an expat series, for friends thinking of living part of the year in another country, with places like Mexico and Portugal in mind. They also want to hear where guests would like to go.
I named the pattern. They are evaluating light before going heavy. Try one thing, try another, and see what the market says. Michael agreed, and added the reason. They want to respect what Dan Ware created, keep longtime guests engaged, and bring a little freshness so those guests invite friends.
Even the itinerary leaves room for the unexpected. They plan to give guests a couple of hours on their own to explore and get lost. On a Christmas market cruise in Germany, a barge crash blocked the river, and the tour had to take another route. A few guests were upset at first. Once they got into it, they went to see something else.
How to apply this to your own business this week
A few questions to sit with, drawn from Dan and Michael's story:
What do your most loyal customers love that you must not lose? Write it down before you change anything.
Where can you grow wider instead of bigger? More offers, more trusted people delivering them, same feel.
Which new idea can you test light this month, with a small group, before committing to it?
Who could you ask, directly, what they wish you offered?
If you are thinking of turning a love into a business, what else will you have to come home to?
And one more, from their napkin. Where are you treating being lost as a problem, when it might be a view worth noticing?
Related Insights
Dan Ware built something that could outlast him. If you wonder whether your business could keep going when you step back, start here. The Subtraction Test
Wisdom Weekly. Get Wisdom Weekly, a short Sunday letter on leading what you have built. Subscribe to Wisdom Weekly
This conversation is part of the Exits, Freedom and the Second Stage Growth Hub. See every Growth Hub.
🎙️ Listen to Episode 319 of Paper Napkin Wisdom
▶ Spotify
▶ YouTube
Comments