Inside the minds of successful business owners. 'I wake up hungry, and I will not stop.'
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- Entrepreneurship comes with risk and uncertainty. As one founder put it, "You have to be insane."
- Two successful founders share the mindsets that helped them push through when failure felt possible.
- They explain how anyone can develop the resilience and confidence to take entrepreneurial risks.
A traditional job typically comes with a regular paycheck and benefits — a measure of stability and predictability.
Entrepreneurship offers neither. It comes with risk and uncertainty. There is potential for a big payoff, but no guarantees.
Popsmith CEO Tal Moore put it bluntly: "You have to be insane to be an entrepreneur," he told Business Insider. "Because there's so much risk. There's so much turbulence."
He and his cofounder nearly ran out of money while building their high-end stovetop popcorn popper.
"I ended up selling $600,000 worth of my personal stock to keep us afloat," Moore said.
It was stressful, of course, but Moore felt he had to find a way through — not only because he had invested heavily in Popsmith, but because friends and family had, too.
"They bet on me. They bet on my brand," he said. "If you lose your own money, that's one thing. But there was just no f---ing way that I was going to lose my friends' and family's money."
Kyle Ray had a different source of motivation. In high school, one of his teachers told him he'd end up working at McDonald's.
Rather than feeling discouraged, Ray used the comment as fuel.
He never finished college, but he did turn a window-cleaning side hustle he started with $100 into a six-figure business, Geek Window Cleaning, which now serves hundreds of clients across multiple Texas cities.
Ray said he had doubts "all the time" that the business would work, but wanting to disprove that teacher meant adopting a failure-is-not-an-option mindset.
"I'm going to make this work," he decided. "I'm just going to figure it out."
Throwing "Hail Marys"
When Moore and his business partner had just two weeks of cash runway left, saving the business meant getting attention and moving product without spending much money.
"At this point, I had to throw some Hail Marys," Moore said.
His first idea, which he called "harebrained," was to send poppers directly to the CEOs of Williams-Sonoma and Crate & Barrel. He'd designed the product with those retailers in mind, but couldn't get their attention.
"I know my popper will sell on their shelves," he thought. "I just have to get it in their hands."
Jason LeCras for BI
Moore bought the most upscale, high-quality paper he could find at Kinko's, handwrote notes to both CEOs, and "blind-shipped" poppers to them. Within two months, buying teams from both companies had reached out, he said.
Then came Oprah.
Moore had no idea how to get on Oprah's annual "Favorite Things" list — "it's just like a total black box," he said — until he spotted an opening on LinkedIn. A junior editor at Oprah Daily had posted about popcorn, so Moore sent her a cold message. She replied, requested a popper, and eventually helped get the product in front of Oprah.
An Oprah Daily editor told Moore that the team considers about 15,000 products each year before Oprah makes her final selections. In 2024, Popsmith made the cut.
After the list was announced, the company sold out of every popper within weeks. Popsmith went on to sell out three more times over the next five months.
As an entrepreneur, "there's a pressure and a will to win," Moore said. "There's an endless drive that just never goes away. I wake up hungry, and I will not stop."
Developing the entrepreneur mindset
Like Moore, Ray has a refusal-to-quit mentality. He views entrepreneurship as a highway without an off-ramp — no Plan B waiting at the next exit.
"If there is no exit, then there's just one path," he said. "And you just have to get through it."
That doesn't mean every business will succeed. In fact, many won't. But Ray believes entrepreneurs need to be willing to take risks, potentially look foolish, fail, and move on to the next idea if necessary.
Often, he said, fear of failure — and other people's judgment — is the real obstacle.
At the core of his mindset is a willingness to care less about both.
Courtesy of Kyle Ray
"If Geek fails now, I'm going to look stupid, but it's like, 'Okay, cool. What's next?' Like, I don't care," he said. "And the earlier you can develop that carelessness — the 'I don't care if I look stupid' or 'I can fall flat on my face. I am still going to go for it' — I think if you get to that point, anybody can go out and be an entrepreneur."
That mindset can be learned, he said. Like any other skill, from swinging a tennis racket to ballroom dancing, it takes time, consistent work, and patience. Ray recommends three steps:
1. Start with books. They're cheap — or free at the library. Ray's top picks include "Inner Excellence" and "Can't Hurt Me." Moore prefers biographies of entrepreneurs and business leaders, from Warren Buffett and Richard Branson to John D. Rockefeller.
2. Find someone who is already doing what you want to do at a high level. Then ask questions, Ray said: "What are you doing that I'm not? What am I doing that's preventing me from breaking through?"
3. Join a mastermind or hire a coach. Ray has multiple.
"When there's something I don't know, or I need to learn, I start to look for coaches," he said. "It's like a wormhole, right? If you can find somebody that knows something about where you want to be, they can help you collapse time and just jump forward to that spot."
