The Insight That Changed How These Founders Think About Everything Six entrepreneurs share breakthrough moments that changed how they do business.

1. Broken promises burn bridges.

"Six months after I cofounded a small activewear brand, [e-commerce site] Carbon38 placed an order with us. This was a dream come true, so even though I was unsure we could execute on their timeline, I went for it. As a result, we didn't let our fabric sit long enough before manufacturing and sent Carbon38 product that was too stiff and rough to sell. They returned all of it, and I made a terrible first impression. I learned to never compromise quality." — Kassia Davis, founder and CEO, KADA

2. Stinginess is shortsighted.

"In the early days of Hims, I negotiated with vendors until there was no more room for savings. I was proud of this. But years later, an early Hims employee emailed me about the super-­uncomfortable conversations I used to have with vendors. He suggested it was silly to have saved a few thousand dollars here and there when we ended up building an incredibly successful company. In that moment, I realized how much more important it is to create value at a startup than nickel-and-dime vendors." — Joe Spector, founder and CEO, Dutch; cofounder, Hims

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3. Small gestures make big impressions.

"When I left my job at DreamWorks Animation, I was pleasantly surprised to receive a handwritten note from then-CEO Jeffrey Katzenberg. There I was, a midlevel colleague of nearly 3,000, getting a handwritten thank-you on my way out the door. It taught me a lesson that I've carried through everything I do since then. The small things matter a lot." — Colleen Heidinger, president, 43North

4. Creativity blooms in crisis.

"Until 2020, our hero product was a chai concentrate, sold primarily to coffee shops and cafés across the country. So when the pandemic hit and coffee shops closed, I lost the vast majority of my customers. But the pandemic was the catalyst I needed to get creative and expand the company's portfolio to a new product line. If chai lovers couldn't come to coffee shops, we would meet them where they were: at home. Our new loose-leaf chai blends became our best-sellers." — Farah Jesani, founder, One Stripe Chai

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5. Listening closely can focus your impact.

"In 2019, my cofounder and I traveled to a healthcare clinic in Sonoma — where opioid abuse was on the rise. But talking to doctors there, we found that many had no idea how many people in their city were struggling with addiction. It just wasn't something they knew to ask about or look for the signs of. After our visit, we had a moment of clarity: To make an impact, we needed to work directly with patients. We pivoted from a B2B to a B2C model." — Ankit Gupta, founder and CEO, Bicycle Health

6. Bigger isn't always best.

"One of our earliest big breaks was Nordstrom carrying our collection. Nordstrom has prestige and powerful scale, but AYR was created to be a slow-fashion, direct-to-consumer business. We had to pick a path. Our first year without Nordstrom, we barely grew at all. But once we did, we had better margins, less excess inventory, and more data for future decision-making." — Maggie Winter, cofounder and CEO, AYR