When it comes to being a successful entrepreneur, Jetblack CEO and founder Jenny Fleiss is two for two.
She's half the duo that created Rent the Runway, the revolutionary clothing rental company she and her friend -- and then-business school classmate -- Jenn Hyman started back in 2009.
In less than 10 years, Rent the Runway, valued at an estimated $770 million according to PitchBook, has transformed the retail industry, creating a new way to shop and democratizing designer clothing and accessories.
Fleiss stepped down from her role at Rent the Runway last year, remaining on as a board member and adviser, to create Jetblack, the first portfolio company inside Walmart's startup incubator, Store No. 8.
Jetblack is a subscription-based shopping concierge service targeted to busy parents. Users can text nearly any shopping request to Jetblack and receive items the same day or the next day for no additional delivery or shipping charge. The company utilizes a combination of artificial intelligence and expertise from professional buyers.
"I'm a serial entrepreneur at heart," Fleiss recently told ABC News' chief business, technology and economics correspondent Rebecca Jarvis. "Like, every day I am seeing a new problem, thinking of a new solution.”
Fleiss has a passion for developing a company in its early stages, and that drive ultimately led to her decision to leave her day-to-day role at Rent the Runway.
Careers are like a jungle gym these days -- you can go from one place to the next, you can try one industry out and then flip to another.
"I have to hold myself back on starting and working on new concepts all the time," she said. "So that energy and that drive to work at a really early stage startup really started to get a little bit lost as Rent the Runway grew. I was still kind of itching for that 30-person team in a room, all crammed there working on an early-stage concept."
She said that as an entrepreneur her work is embedded into her life, and she constantly using her own life experiences to think of creative solutions that sometimes lead to multi-million dollar businesses.
"My everyday problems that I see, as a busy mom who works, have evolved," she added. "When I was a woman wearing outfits and going to parties in my 20s and 30s -- evolving Rent the Runway came out of that.”
I'm a serial entrepreneur at heart. Like every day I am seeing a new problem, thinking of a new solution.
When it comes to the worst advice that she never took, Fleiss didn't hesitate, recalling something that many post-grads are often told: Build a resume.
"The worst advice that I've received is to build my resume, because I think if you just do your career based on building your resume then you don't actually get into roles that you're passionate about," she said.
Fleiss said she was advised to go into consulting and banking solely to build her resume, rather than to pursue entrepreneurship.
"I understand that -- especially if you're not sure -- it's a fairly safe bet," she said. But it's really dangerous if you keep saying, 'Well, I’m going to do this because that's going to build my resume and eventually I'll work towards that place.' I don’t think careers have to work in that way. Careers are like a jungle gym these days -- you can go from one place to the next, you can try one industry out and then flip to another."
Experience across industries and roles is something that has become essential to Fleiss and what she looks for in prospective employees.
"That's what makes people dynamic and able to innovate in different industries," she explained. "That's how I think I've been able to add value entering new industries is my perspective coming from different industries in the first place.”
Hear more from Jenny Fleiss on episode 95 on the “No Limits with Rebecca Jarvis” podcast.