This time it's personal: Bobbi Brown on building her next great makeup company with family at the center

On LinkedIn’s video series, This is Working, I sit down with top figures from the world of business and beyond to surface what they’ve learned about navigating setbacks and achieving more in work and life.

This week I sat down with the Jones Road Beauty mother-son powerhouse duo of founder and makeup mogul Bobbi Brown and son and CMO Cody Plofker.

I’ve spoken with Bobbi Brown a few times for #ThisisWorking, getting her thoughts about entrepreneurship and second-acts. Bobbi is a legend in the beauty business, a self-taught cosmetics creator who bucked the industry — in terms of how makeup looks and how you market it — when she founded Bobbi Brown Cosmetics in 1991. Four years later, The Estée Lauder Companies Inc. bought her eponymous brand. After decades working for a larger corporation, Bobbi left in 2016 in search of something new.

That new thing eventually became direct-to-consumer makeup brand Jones Road Beauty, launched in 2020, the same day her non-compete with Estée Lauder was up. 

So Bobbi knows beauty. And she knows how to launch and how to scale. What I hadn’t thought of her as was an expert in was how to manage work and family. But then someone pointed out to me that her chief marketing officer happened to be one of her three sons. Her husband serves as chairman of the board. Her head of brand was her daughter in law. And suddenly Jones Road started looking less like a reborn Bobbi Brown Cosmetics and more like a modernized Estée Lauder: A company founded by a female visionary, whose large working family made the vision even greater. (Way back in 2005 I wrote about the family dynamics inside Estée, which was fascinating to see how a second and third generation make their mark).

So for the latest This is Working, I sat down with both Bobbi and CMO son Cody to talk about how they ended up working together and what others can learn from how they manage their relationship. 

Here are three takeaways:

1. Be clear on the skills you need from your family member — and if you’re the employee, know what you can bring to the table 

When Bobbi launched her new DTC brand, she realized her marketing strategy was severely lacking. Cody, who advised other companies, had good experience and and at first Bobbi and her startup team just wanted him as a consultant. Then she realized that the best move would be to hand the strategy over. Cody, however, had no interest.

“It’s super exciting, but probably not a great idea for me to work with my mom,” Cody recalled “At that stage in my life and, and our relationship, I thought it was probably safer not to.”

But Bobbi deliberated on the needs and realized that his skill set was exactly what Jones Road needed. She committed to winning him over and to making it work while preserving family dynamics. “We travel together as a family,” Bobbi said. “My family is my posse and they’re the most important thing I have. So if it was going to get in the way of our relationship, we wouldn’t have done it… He knew not only what he was doing, but he knew what we didn't know.”

“It just so happened that the one thing in the world that I am any good at was the one thing that Bobbi and Jones Road needed help with,” Cody added. 

Not that Cody hasn't rethought the role: “There's a couple times he quit on a Saturday walk, but you know, soon, he changed his mind," Bobbi said.

2. Being intentional about communication is essential. Words matter and the person you see 9-5 is also the person you travel with and see on weekends.

Bobbi and Cody disclosed that one of the biggest challenges in forging a successful work-family dynamic lies with communication.  

“We speak different languages,” Bobbi said. “You know, someone who is 30 and someone who is in their 60s — so I'm learning a lot and hopefully he's learning some of the traditional marketing things that I have been doing for over 40 years.”

Cody pushed Bobbi to find value in listening and to embrace critical feedback. Bobbi knows what she wants to get done and how to get it done. But ordering around your kid can leave scars that might not form when ordering around in-it-for-a-paycheck workers. And not accepting feedback from your children can be damaging in a way that extends beyond the office.

“I'm a very visual, creative entrepreneur with a million ideas a moment — sometimes I don't push myself to listen to what other people are saying,” Bobbi said. “You have to be really transparent about that so you can only do it with someone you have a good relationship with. You just have to know what your limitations are.”

3. Remember that in the office, you're colleagues first

You probably won’t hear Cody call Bobbi “Mom” at the office. He uses “Bobbi” instead. (Though it’s easier that he’s been doing that for most of his life, to Bobbi’s chagrin.) For Bobbi, it’s about holding back on the things she really wants to ask about: “The hardest thing about working with my son is I have to be careful to not mother him so much,” Bobbi quipped. “‘Cody, have you taken a break? Have you gone for a walk? Do you have enough water? Are you breathing?’”

That last one might be a pretty good question for any of your colleagues, to be fair.

Beyond the Jones Road examples, I asked Bobby Stover Jr., who heads up EY America’s family enterprise business, what he’s seen from working with family businesses in how to be successful. There are some 5.5 million family-owned businesses in the United States, and these businesses are responsible for nearly 60% of the country’s GDP, according to the Cornell SC Johnson College of Business .

Yet 70% of those businesses fail or are sold before the second generation can take over. Bobby added two more hard-learned tips to Bobbi and Cody’s insights: 1) Plan for succession early on; and 2) plan for growth. He’s seen companies fail that haven’t clearly thought about who is the right family member to run the company for the long run and haven’t pushed the next generations to get aggressive about new opportunities. “Family businesses must continue evolving and making the adjustments needed to stay competitive as the world changes,” he said.

Bobbi and Cody — and Payal Patel Plofke and Steven Plofker — seem set on making sure they’ve nailed the growth part, coming up with new product lines and packaging ideas that have beauty buyers raving. The next step is to see just how big this family business can get: Can Jones Road becomes a Brown dynasty?

Have you worked in a family-run business? What’s your secret to working with family?

Let me know in the comments, or send me an email at thisisworking@linkedin.com. Tell a colleague to subscribe to This is Working by clicking here!

More Toto Wolff • Al Roker • Vas Narasimhan • Barack Obama • Oscar Munoz • Coltrane Curtis • Sally Susman • Gina Rometty • Christine Lagarde • Richard Branson • Ray Dalio • Corie Barry • Ryan Gellert • Everette Taylor • Jesper Brodin • Chrissy Taylor • Niels Christiansen • Terry Crews • Tarika Barrett • Bill Gates • Toto Wolff  • Kimberly Bryant • Mark Cuban