Dealers Leaders Newsletter #1: How Richard Branson, Tim Ferriss, and Milton Hershey Can Help Your Dealership Thrive

Dealers Leaders Newsletter: How Richard Branson, Tim Ferriss, and Milton Hershey Can Make Your Dealership Thrive

There’s something about success stories that captivates us. We love hearing about how wildly successful people like Richard Branson built empires and how Tim Ferriss made a career out of being curious.

But what’s the use of these tales if we can’t translate them into something practical? For dealership leaders, sales managers, and car sales consultants, the magic happens when we take these big ideas and use them to sell more cars and build stronger businesses.

So, let’s unpack some lessons from Branson, Ferriss, and Hershey—three very different personalities, yet united by one thing: they all dared to do things differently.

Richard Branson: Selling More Than Just Cars—Sell an Experience

First, picture Richard Branson. Think about this guy—he starts an airline in an industry famous for crushing newcomers. His track record? Amazing. His failures? Many. What makes Branson so remarkable, though, is his ability to bounce back and turn those failures into something more valuable than success: experience.

Branson’s secret sauce? Customer experience.

He doesn’t just build companies; he builds companies people love. His entire philosophy revolves around putting the customer first. It’s not just about selling a product. It’s about creating a memorable moment. For Branson, the key was always about going beyond expectations—which, in your world, translates to not just selling a car but giving your customer an experience they’ll rave about.

Now, how does this help your dealership?

Action Item: Reframe the sale as an experience.

Start thinking of car sales the way Branson thought of airline tickets. Sure, people need a car. But what they want is to feel good about their decision and their interaction with your dealership. Ask yourself (and your team): what can we do to turn a boring sale into an experience they won’t forget? Maybe it’s a standout delivery process, or maybe it’s an after-sale “thank you” surprise. The possibilities are endless.

Tim Ferriss on Curating Curiosity and Experimentation

In the Patrick O’Shaughnessy podcast (Invest Like the Best) with Tim Ferriss (the guy who managed to turn his curiosity into a multimillion-dollar brand), Ferriss talks about how the successful constantly tinker. They experiment, tweak, adjust, and improve. His big point? Being curious and always trying new things is what separates the good from the truly great.

Curiosity in a car dealership setting might sound like a luxury—how can you “experiment” when you’ve got quotas to hit? But Ferriss would say that’s exactly why you have to experiment. When you treat your day-to-day as an opportunity to learn, grow, and explore, you start seeing opportunities that your competitors miss.

Action Item: Encourage small-scale experimentation.

Have your sales team try out different pitches. Tweak your promotions. Test new follow-up methods. The key is to stay curious and learn from what works. Even better? Share these findings in a weekly meeting. Turn curiosity into a culture where learning isn’t just allowed—it’s expected.

Milton Hershey: The King of Resilience and Long-Term Vision

Then there’s Milton Hershey, the chocolate magnate. (check out David Senra’s podcast “Founders” episode #146) Before his chocolate empire took off, Hershey failed. A lot. He launched several failed businesses before hitting on something that stuck. The reason his story matters for you is that Hershey’s failures weren’t wasted. Each one taught him something that led to his eventual breakthrough.

For dealership teams, that’s a powerful lesson. It’s not about perfection; it’s about persistence. The best teams don’t avoid failure—they learn from it and come back stronger.

Action Item: Reframe failure as learning.

Encourage your team to take risks, not just play it safe. Failure isn’t a dead end—it’s feedback. After each month, take a moment to reflect on what didn’t work. What can be adjusted? How can your dealership improve the way Hershey improved his chocolate?

Connecting the Dots: Curiosity, Experience, and Resilience in Your Dealership

Here’s where it all comes together: Branson’s obsession with the customer experience, Ferriss’s curiosity-driven experiments, and Hershey’s resilience in the face of failure. Each of these traits is critical for running a successful dealership in today’s market.

It’s no longer enough to just sell cars. Your customers want to feel something when they make a purchase. Your salespeople want to feel empowered to try new things. And your managers need the resilience to lead their teams through challenges without missing a beat.

Thought-Provoking Questions:

1. Customer Experience: What’s one thing you can implement this week that will turn a routine sale into a memorable customer experience? How can you inject a bit of Branson’s philosophy into your dealership?

2. Curiosity and Experimentation: How often do you and your team experiment with new sales techniques? What could you try this week that might improve your process—even if it’s just a little bit?

3. Resilience: How do you handle setbacks at your dealership? Is failure seen as a disaster or an opportunity for improvement? What’s one “failure” from the past month you can turn into a learning experience?

Three Quotes for Inspiration:

1. “Do not be embarrassed by your failures, learn from them and start again.” — Richard Branson

Sales is tough. Some deals won’t go your way. What matters is that you keep going.

2. “Curiosity is the fuel for discovery, inquiry, and learning.” — Tim Ferriss

Stay curious, especially in the fast-moving world of automotive sales. The next breakthrough could be just a question away.

3. “Give them quality. That’s the best kind of advertising.” — Milton Hershey

In an industry as competitive as yours, quality service and customer satisfaction are the best marketing tools.

With these lessons in mind, challenge yourself to create more value at your dealership. Ask questions. Experiment with new ideas. Fail spectacularly—and then get back up again. Richard Branson, Tim Ferriss, and Milton Hershey didn’t get to where they are by playing it safe, and neither should you.

Stay driven!

Dealers Leaders