• Michelle Cordeiro Grant, the founder of Lively, a women's lingerie brand, is stepping down as CEO.
  • Cordeiro Grant is moving on to new ventures in categories like health, wellness, and Web 3.0.
  • She listed three questions founders should answer to know when it's time to leave their startup.

Last week, Michelle Cordeiro Grant, the founder and CEO of Lively, a women's lingerie brand, announced her plans to resign in October.

In an exclusive interview with Insider, Cordeiro Grant likened the bittersweet moment to her senior year of high school. "You have to graduate and go create and it's heartbreaking," she said. "It's a very emotional change that you don't expect." 

Cordeiro Grant, a former Victoria's Secret employee, founded her direct-to-consumer brand in 2015 as the antithesis of the sexy lingerie supermodels wear. She built Lively by appealing to everyday women, many of whom made up the company's 100,000-customer ambassador program. Wacoal, a Japanese lingerie manufacturer, acquired the brand for $85 million in 2019.

It can be difficult for founders to know when it's time to leave the company they spent so much energy building. Cordeiro Grant gave her tips for entrepreneurs on knowing when it's time to leave, starting with three questions she asked herself.

How to know it's time to leave your startup

1. Is my company still challenging me?

A few years after Lively's acquisition, it wasn't a startup anymore: It had grown into a mature company with double the original number of employees. Leading Lively began to feel like Cordeiro Grant's old corporate job at Victoria's Secret, which she said wasn't a bad thing, but that it was too comfortable. That was her first indication it was time to leave. 

Cordeiro Grant is happiest when she's creating and watching her ideas grow. "I live for the unexpected," she said. "To see things that don't currently exist become a new way of life."

2. Do my own goals align with my company's goals?

Cordeiro Grant recommends founders list out their personal and company goals to see if the two align when deciding if it's time to step away. If the columns no longer mesh, it's a good indication that perhaps you're moving in a different direction from where your company's headed.

"If I wrote down that list three years ago, it would be open stores, build new channels, launch in Target, lean into new categories — they were the same," she said. Now the lists are different and "for the first time, what Lively needs and what I need are different and that's okay. Someone else can do my job better." 

3. Am I the best person for the job?

Cordeiro Grant didn't always see herself as a serial entrepreneur, but she's discovered that she loves the thrill of new ideas. When a brand name comes to mind, she buys the domain on GoDaddy. She's invested in at least 100 domain names so far, she said. 

Many serial entrepreneurs prefer chasing their latest whims rather than being with a company long-term, meaning they're not always the right person to lead a company, she added. "We see things that don't exist, but in our minds they already do and now we just have to go build it," she said.  

Michelle Cordeiro Grant sits in a white dress on a white couch with a plant behind her
Michelle Cordeiro Grant.
Sergio Villatoro

What to do once you leave

While she orchestrates her exit, Cordeiro Grant is taking time to formulate her next moves. Many of her ideas come from pitch decks she makes on her phone while running — she conceptualized Lively on a jog through Central Park. Today, she's running on the beaches of East Hampton brainstorming her next three ventures. 

First, she wants to build a wellness brand to make healthy living more accessible. "I see New York, Florida, LA, these pockets really living in health and wellness," she said. "Then I go back to where I'm from, which is Pennsylvania and middle America, and I see the consumption of products that aren't very good for people."

Next, she wants to see more representation of women in Web 3.0 — the new generation of decentralized internet based on blockchains. "Five percent of the successful entrepreneurs of Web 2.0 were women," she said. "That needs to be 50%, at least, in Web 3.0." She's learning more about the space and launching a podcast this fall called, "Web 3 with MCG." 

She's keeping her third venture under wraps for now, but she wants to merge categories similar to the way Lively combined athleisure and lingerie. "I don't know what it is yet, but I've been prototyping and designing," she said. "It's also where I find solace, tinkering and blending categories."