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Dennis O'Leary
- Retired NYPD Detective, Mafia Tour Guide
- $800,000 estimated bookings
Dennis O’Leary runs mob tours of New York City.
Three hours past the old Little Italy hangouts, finishing with spaghetti at an old-school Italian restaurant.
Dennis spent eight years in the NYPD’s Organized Crime unit, and says he grew up in a building full of wiseguys…
I grew up with it and then fought against it and now I’m talking about it.
His listing says 10K+ guests on Airbnb over the years, and at $79 to $89 a head that’s around $800K of bookings 🤑
My First Million reckons Dennis has cleared $1M+, and Airbnb is just one of his six channels.
Two more tour businesses highlighted by MFM 👇
- Asia Grant’s Nolita perfume walk charges $95 to $155, up to 8 people on each tour ($760+).
- Nick Gray’s Museum Hack charged almost $200 for unofficial museum tours and did as much as $2.8M in revenue.
But don’t expect to get rich quick: it took Dennis over three years to reach 8,500 guests.
Two tours a week at eight people is $65K of bookings in year one, maybe $50K after fees and food.
What if you don’t have stories like Dennis or you’re not an extrovert like Nick?
Find the showman in your town – the retired cop, perfumer, music nut, whoever – then run the listings, bookings and venue deals for a cut 😎
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