The Hardest Lesson I Learned This Year

Every failure is an opportunity to learn. As we look back on 2025, we asked six entrepreneurs: "What went wrong this year, and what will you do better next time?" Here are their answers.

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1/ Diversified supply chains are crucial.

“When your sourcing is too concentrated, you're vulnerable. For us, the moment tariffs spiked, it became crystal clear that relying on a limited set of manufacturers and suppliers created real exposure. We had to react quickly, find alternative partners, and rethink our manufacturing footprint. The experience underscored a lasting lesson: Diversification isn't just a best practice, it's a safeguard for business continuity.”

—JILL LAYFIELD, CEO, Birdy Grey

2/ Putting comfort over conflict is costly.

“Leading up to a major system implementation, every time I asked probing questions, our CTO would react defensively. I wanted to give him space, so I held back from getting deeply involved. In hindsight, I was avoiding necessary conflict. The result? The implementation went poorly. Customers were disappointed. We're still fixing issues three months later. And the CTO resigned. Outcomes matter more than comfort.”

—CHAD STARK, CEO, Stark

3/ No one is immune to cyber fraud.