Lessons from the driver’s seat

Read: golf course

Hi there! I hope you’ve missed me as much as I’ve missed you. Thanks for letting me take a little summer breather, from both school and Substack.

Where have I been, you ask? Back at my family’s business, soaking up all I can before heading back to Boston for my final two years of the JD/MBA program.

Going forward, you’ll hear from me once a week instead of twice, which I feel like is just going to be much more sustainable for both your inbox and my sanity. I still have full conviction that Substack is the place to be right now. Every day, new voices are showing up here, from writers to creators to brands to magazines (looking at you

Coord Health

&

Inside The Room

). Plus, the platform just raised $100 million this July, so the energy is real.

There’s a lot to catch you up on (IYKYK), but we’ll start with six business lessons I’m taking away from this summer.

1. People do business with people, not companies

At the end of the day, companies don’t shake hands, people do. My parents started their business more than 30 years ago by winning over one customer at a time. They didn’t have a fancy brand or a marketing machine; they had trust. And that trust grew through consistency, relationships, and actually delivering on what they promised.

It’s easy to think growth comes from scaling fast or chasing the next big thing, but in reality, it’s often just showing up for people, over and over again, until they know you’re someone worth betting on.

2. You can’t get a raise on a customer you don’t have

This is one of my dad’s favorite lines. It means you have to get in the door first, even if the terms aren’t perfect. If you overprice or overpromise, you risk losing the deal entirely. But if you land the customer, even at a thinner margin, you earn the chance to prove your value. Over time, that relationship grows, and so does the compensation. It’s patience disguised as strategy.

I’ve also been listening to Unreasonable Hospitality, and the whole book is about obsessing over customers in ways that make them feel valued. Pair that with my dad’s advice, and the lesson is clear: start by showing up, then earn the raise later.

3. What’s right is right & what’s wrong is wrong

Business tests your integrity every single day. There will always be shortcuts that look tempting, or compromises that seem harmless “just this once.” But those decisions add up. My dad’s approach is brutally simple: if it’s right, you do it. If it’s wrong, you don’t. No gray area. And it makes decision making easier, because you’re not wasting energy rationalizing your way out of your own values.

4. You can get lucky, but luck doesn’t last

On How I Built This, Guy Raz always asks founders how much of their success they attribute to luck versus hard work. My dad would say: you usually need luck to get started. A chance encounter, a big break, someone willing to take a risk on you. But luck alone won’t sustain you.

What matters is what you do with that luck once it shows up. Do you run with it or waste it? The real story of success is about preparation, persistence, and what you build after the lucky break fades.

5. Keep the main thing the main thing

Distraction is everywhere, from new markets to shiny side projects to ideas that sound exciting but pull you away from your core. For my parents, the main thing has always been security. That focus is why they’ve been able to grow consistently over decades.

When you’re clear on what you do best, you protect your energy, your team, and your reputation. It doesn’t mean you never evolve, but it means you never lose sight of the foundation. Knowing what your “main thing” is, whether in business, school, or even relationships, is half the battle.

6. Decide, delegate, & disappear (the 3 Ds)

This is my dad’s leadership philosophy in three words. Decide: be clear and decisive about what you want. Delegate: communicate it, give the right person the responsibility, and trust them to do their job. Disappear: get out of the way. No micromanaging, no second guessing. When leaders waffle, teams get stuck. When leaders cling, people shut down. The best managers create clarity, hand over ownership, and then let their people run with it.

Until Friday,
Taylor