Chris Boots was building a custom pantry cabinet at his wife's uncle's shop in 1999 when he looked at the top sitting on the cart and thought it kind of looked like a casket. He'd always wanted his own business. He didn't know what business. That cabinet was the seed.

He spent nights on the bed flipping through funeral trade magazines while his wife asked what on earth he was doing. He joined the Casket and Funeral Supply Association — he'd later become its president. He bought a CNC router he didn't know how to operate and was halfway through training in Atlanta before he asked the instructor what the machine actually looked like. Chris walked into the casket industry right as cremation rates climbed from 20% to 70% and the number of casket companies collapsed from hundreds to fifteen. He built CJ Boots Casket Company anyway, going after the high-end Marcellus niche that conglomerate buyouts had cut off from independent funeral homes.

Twenty-one years later he sold it, ran it through COVID for the new owners, tried Florida real estate, and landed in commercial insurance after a chance conversation on Lido Beach with a guy who happened to insure the same trade association Chris used to run. His advice for day one of any new business: understand cash flow before anything else. His motto for the rest of it: don't be afraid to go out on a limb, because that's where the fruit is.

Learn more about Chris Boots and his commercial insurance practice at https://www.linkedin.com/in/chris-boots-2990735/. Listen to more Indianapolis Business Leaders at https://defaultprofitable.com or subscribe to Default Profitable on your favorite podcast platform.

David Reynolds and his sister Christina Reynolds-Grisby spent more than 25 years at the same electrical contracting company. The plan was always to buy it. They'd consulted with the bank, drawn up the legal work, and lined up the transfer of ownership. The morning the deal was supposed to close in 2023, they walked in and got introduced to the new owners. A private equity firm had bought it out from under them.

They decided to start Reynolds Electric standing in the parking lot that same morning. Three years later, they're a residential and light commercial electrical contractor in Indianapolis, an authorized Generac and Kohler dealer, with techs in the field and an office staff behind them.

In this conversation, David and Christina get into what 25 years as employees doesn't prepare you for. Picking a business structure. Finding a CPA. Building a brand from scratch. Christina spent six months on the van wrap. Her hair wasn't right, the shoes weren't sitting where she wanted them, the caricature head kept changing size. Her advice for any new founder is progress over perfection. She'll be the first to admit she didn't take it.

The takeaway Matt pulls out of the episode comes in two parts. Start it sooner than you think you want to. And if you're negotiating a business takeover with somebody you've trusted for two and a half decades, get it in writing anyway.

Learn more about David Reynolds, Christina Reynolds-Grisby, and Reynolds Electric at https://powerbyreynolds.com. Listen to more Indianapolis Business Leaders at https://defaultprofitable.com or subscribe to Default Profitable on your favorite podcast platform.

Will Steck and his sister both started at Winthrop Supply on the same day in 2009, sweeping warehouse floors and loading trucks. Eleven years later, they bought the business from their dad. Winthrop is a fourth-generation Indianapolis plumbing supply company started in 1939, and also happens to be the longest-running Rheem distributor in the country.

In this conversation, Will talks about the three years he and his sister spent modernizing the ERP before they owned a single share, the moment their father asked if they were in or if he should find a buyer, and the biggest lesson he'd go back and tell himself: stop trying to clone yourself. Find what your people are good at and let them do that.

Learn more about Will Steck and Winthrop Supply at https://www.winthropsupply.com.

Listen to more Indianapolis Business Leaders at https://defaultprofitable.com or subscribe to Default Profitable on your favorite podcast platform.