Self-made millionaire shares No. 1 mistake new founders make

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If you want to be a business owner, the time to get started is now. Not tomorrow or next week, but today.

That’s according to Emma Grede, the self-made millionaire founding partner of Skims, CEO of denim brand Good American and the first-ever Black woman investor judge on ABC’s “Shark Tank.”

“Here’s the truth. The No. 1 mistake founders make is waiting until everything feels perfect,” Grede said in a Nov. 4 episode of her “Aspire” podcast. “I’ve [started a business] more than once, and I will tell you, I’ve succeeded. I’ve failed multiple times. And having mentored and invested in countless ideas and founders, I’ve learned that most people overcomplicate the process and they fail to start.”

In fact, 62% of Americans want to be their own boss one day, according to a 2024 Gallup poll. The poll respondents who said they “have seriously considered starting a business” cited finances, lack of business knowledge and a “lack of confidence that [the] business would succeed” as some of the top challenges they anticipated facing as entrepreneurs.

But risk is an inherent part of entrepreneurship, and it shouldn’t keep you from at least working on a business plan, Grede said.

“We all have bills to pay, people that rely on us — children, parents, significant others — and that’s real. But the truth is, taking a risk actually is part of starting a company,” said Grede. “Risk is not something that you can get rid of. It’s something that you need to plan for.”

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Entrepreneurship is littered with examples of companies founded in imperfect circumstances. Steve Jobs was a college dropout who launched Apple in his garage. Jensen Huang “had no idea” how to start Nvidia when he co-founded the AI company at a Denny’s breakfast bar, he told CBS’ “60 Minutes” in April 2024. 

Starting a company, especially when you know that your business model isn’t perfect yet, can be difficult if you’re risk-averse, Grede said. Her advice: Before your mind starts racing, thinking about whatever barriers might make it hard to realize your dream, reframe your idea of risk.

Specifically, try to see risks as calculated actions that’ll become learning opportunities, said Grede. If the risk doesn’t pan out, you can create a new plan of action based on your lived experience and “refine your approach” from there, she said.

Jeff Bezos has endorsed the concept of calculated risks, calling them “one-way doors [or] two-way doors,” on a December 2023 episode of the “Lex Fridman Podcast.” A two-way door risk is easier to take because it’s reversible, so “you can come back in and pick another door,” Bezos said. A one-way door risk isn’t recoverable without challenges, however.

“You go in that door, you’re not coming back,” said Bezos. “Those decisions have to be made very deliberately, very carefully.”

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