"Maybe 3 Shows a Year": How a Grammy-Nominated Singer Built a Booking Machine

When he asked an orchestra-world insider how many symphony dates he could realistically book, the answer was "maybe three a year." He ignored it. With his wife running the office and an in-house booking team, he went on to book 20 to 30 orchestra shows a year. He now performs 75 to 120 shows annually across symphonies, casinos, theaters and festivals. On this episode of Bring My Customer: Founder Playbooks, a Grammy-nominated vocalist breaks down the business behind the stage, from the first paid gig to building a company that books him year after year. Inside this episode: → The best business advice he ever got: "This is show business. Show is just the adjective." → How one recommendation turned a small orchestra spot into his own headline show → Splitting from a powerful management team and rebuilding his bookings from scratch → Why he built an in-house booking team instead of relying only on agencies → Exclusives, non-competes and one-sided contracts: how he negotiates → Growing in a market that looks like it's shrinking on paper → Why it's better when someone else sells you than when you sell yourself → Did the Grammy nomination actually bring in bookings? His honest answer → "Wear the hat of the person you're speaking with": the sales lesson behind it all Whether you're a performer, a consultant or any service business owner who hates selling yourself, this is a masterclass in building demand that doesn't depend on luck. Chapters 00:00 Intro 01:51 The 30-second pitch 02:47 "That's what the shower is for" 05:19 The dare that started it all 06:16 The cassette that changed his dad's mind 07:10 The first paid gig and the roadie years 12:07 Choosing a "dying" genre on purpose 12:33 "Show is just the adjective" 15:32 The first orchestra show 19:41 What he got wrong on the business side 20:45 Starting over after splitting with his team 22:04 Told 3 shows a year, booked 20–30 23:43 What outsiders don't understand about performers 26:19 The customer autopsy 27:25 75–120 shows a year: "we're in the travel business" 28:48 Building an in-house booking team 30:06 Exclusives, non-competes and contracts 32:15 Growing in a "shrinking" market 38:05 The booking that went wrong 39:47 Why someone else should sell for you 42:53 Did the Grammy nomination bring bookings? 45:46 Advice for any service business Want a predictable flow of customers for your business? Check out www.bringmycustomer.com #musicbusiness #sales #smallbusiness #founderstories #podcast