G: You’ve built brands across industries and eras—from clean beauty with Jones Road to your new Gen Alpha-focused company YAWN. When it comes to business-building today in 2025, what’s something that’s surprised you or felt totally different from previous chapters?

T: Having started brands over the past five to ten years, the world has changed—and it’s totally different now. Especially in beauty. I always say the barrier to entry is that there is no barrier to entry. Anyone can start something.

But with that said, it’s opened up so many different opportunities, particularly for indie brands, to go deeper into specific needs and create products that are super problem-solution oriented. That’s what people are always looking for. So, if you can hone in on your expertise and build brand equity around that, you don’t have to feel the pressure to come out of the gate with a massive line. The expectation now is different—and that’s a good thing. You can start with a hero product and grow from there.

G: Is that something you saw firsthand when launching Jones Road or more recently with YAWN?

T: It’s hard to compare the two because Jones Road was like playing basketball with Michael Jordan—Bobbi Brown. She’s a master of product. We were lucky that she created Miracle Balm, which is now so culty. I can’t live without it. It’s a desert island product—like, your house is on fire? Grab your Miracle Balm. That was really spectacular. We didn’t hit many walls there.

But with YAWN? Totally different. No Michael Jordan here—we’re coming off the bench. We’re catering to a very underserved, very young audience. That comes with its own challenges: age-appropriateness, privacy laws like COPPA, what’s appropriate to expose kids to. So with YAWN, we’re not just building a brand—we’re kind of building a rubric for how to ethically and thoughtfully interact with young people. That’s a whole new layer I hadn’t dealt with before.

G: That naturally leads into content, right? Especially with an audience that’s both young and digitally native. How are you thinking about content platforms and technology? What’s shifted?

T: With YAWN, we’re actually building toward a very real, offline world. We want to bring experience to tweens in real life, but there will definitely be an online element too. So, the tools of the trade—AI, automation, analytics—they’re not fully in play for YAWN yet, but they are for something I’m launching less than a year from now, which is geared toward adults.

There’s just so much available now in terms of data science, audience development, and content optimization. We’re trying to be extremely strategic: What kind of content are we creating? Where does it live? How do we get engagement with the right people?

If it takes someone seven, ten, twelve interactions to convert to a sale, how can we cut that in half? Hyper-tailored content. Deeper segmentation. You want to speak to each audience segment in a way that actually matters to them. The spray-and-pray content strategy is outdated. It’s expensive—and people are over it. They want to feel seen.

G: It sounds like you’re embracing data, but still grounded in creativity and product. That’s not always an easy balance.

T: Totally. I think we’re finally seeing that you can have both. You can merge brand with data. You can protect your vision, stay true to your values, and still lean into analytics to more effectively deliver your message. That doesn’t mean you’re selling out—it means you’re being smart.

I’m all in on trusting the experts. People who are better, smarter, more open to new approaches than I am—I want to learn from them. Let them do their thing, and let me do mine.

G: You’re also a cherub investor (love that term) with La Cosa Ventures. When you’re evaluating brands as an investor, what separates the ones you back from the ones you pass on?

T: I call myself a cherub investor because I’m working my way up to those bigger checks! But really, most people are interested in me because they want to learn from my mistakes. That’s my pitch: I’ve done it, I’ve messed it up, I’ve fixed it—or not—and here’s what I learned.

When I’m evaluating brands, I start with product. Always. That comes from my years working with Bobbi and her husband. If the product is amazing, you can build anything around it. But if the product doesn’t meet you where you want to be met, you’ve got a problem.

After that, it’s about the people. Are they open? Flexible? Coachable? Jess Sims from Peloton always says, “No ego, amigo.” That’s my favorite. You have to be confident to be a founder—but the best ones can remove their ego and actually listen. That’s who I want to work with.

G: Last question—what keeps you grounded?

T: My family. My daughter. My friends. Nature. I think at the end of the day, you can’t let the highs get too high or the lows get too low. You have to stay somewhere in the middle. And sometimes that means literally taking your shoes off and walking around in the grass.