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Brokers in Cars Getting Coffee: Billy Bridwell

Jun 19, 2020

This episode brings you wit & wisdom from Billy Bridwell. Here's a bit of what you'll get...

  • The single best question to ask during a discovery meeting.
  • Two difference-makers his team has enacted that made a huge impact.
  • One intriguing question that rendered him completely speechless.

Who's the Guest?

Billy Bridwell is the Senior Vice President of Employee Benefits for Keystone Insurers Group. Eleven years ago, his previous firm merged with Keystone. Since then, Billy has built his expertise in being a thought leader and a great sales coach across this growing organization that has hundreds of partners in 13 states throughout the eastern US. Billy has served the industry with many education programs, and is the Past President, of the Indiana State Association of Health Underwriters. Billy is the epitome of a great father to his two boys, investing time with them in a variety of land & water sports. There’s a little hint in the video to Billy’s wife, Ellen, who I'm pretty sure is his secret weapon. 

The Setting

I took advantage of our paths crossing at a conference in Tampa, FL. We kept the scene simple by setting up a camera in a cool coffee shop at the Le Meridien Hotel. It certainly worked to get some jewels of wisdom, but we both agreed next time we’d have more fun if we can get our hands on a 70’s hot rod. 

The Episode

Brokers are smart and they have a lot to say. My favorite comedian inspired me to capture broker insights in a fun way to share with you. With that, we created Brokers In Cars Getting Coffee. Sometimes we’re in cars. Most of the time there’ll be coffee. But we always have great insights about the employee benefits industry!

The Cutting Room Floor

What wisdom was (sadly) left on the cutting room floor? I couldn't leave them there...

On P&C and Benefits playing well together...
Keystone sells on both sides of insurance - and they do it successfully. But it doesn’t just happen. Billy explained that it starts with years of work earning trust across the aisle. And that’s been done with continual conversations and consultations about what each of the businesses need.   

On coaches needing a coach...
Billy is an SVP of sales with teams selling across 13 states. His style is much like a coach – with the camaraderie of a team atmosphere, the push aspect of being accountable to each other, the thrill of the hunt and enthusiasm for the win. He doesn’t think he knows it all, and therefore also works with a business coach of his own through Q4intelligence.

On teaching your kids to dream...
When asked about his dream car, Billy immediately answered that he’d love the newest Corvette. Then he told a story about spotting one recently when out with one of his sons. He said, “When you turn 16, I’ll let you drive my Corvette.” His son replied, “But Dad, you don’t own a Corvette.” And the lesson, with conviction, “Not yet! But I will!”

What are your favorite ideas from the interview? Who else you think I should interview? Email me at


Reid has a passion for helping brokers & employers strategize fresh approaches to benefit plans that contain costs and increase access to care - helping employers & employees control their healthcare dime, time, and peace of mind. He writes & speaks around the country and is the Co-Founder & CEO of freshbenies.

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