My grandfather warned us: leave ego at home

Nathan Bennett says his 91-year-old grandfather Michael—who has worked with his brother Maurice for more than 70 years—told him and his brother to leave ego out of their business partnership before they started Crux Analytics.

When his brother started drilling into the details of a new financial technology company he wanted to build. Nathan Bennett could feel the momentum turning into something more than curiosity. Jacob wasn’t just sharing an idea anymore—he needed Nathan’s engineering expertise to make it real. and the questions kept coming.

About three years ago, Jacob asked him to review the pitch deck for accuracy. Nathan remembers one moment clearly: on the last slide, the team list placed Jacob next to Nathan’s name under his bio. The wording suggested Nathan “knows he wants to jump ship from his job to work with his brother.”

Nathan understood why that landed—he and Jacob had long carried the dream of building something together. But he also knew he was the more cautious one. Leaving a well-established career in medical devices felt risky. and that anxiety pushed him to reach out to family for a decision that didn’t fit neatly into spreadsheets.

The person he called was his grandfather, Michael. Michael is in his 90s and still works with his brother. Together, Michael and Maurice have been in business for more than 70 years, and today they are 91 and 93. Most of their working lives were in women’s fashion, and more recently in men’s shoes.

Nathan asked Michael for the good, the bad, and the ugly of working with a brother. He wanted a clear-eyed view of what could happen if it didn’t work out—because if the startup failed. he still had other career options he could fall back on. What he couldn’t shake was a different concern: that going into business together might change the sibling dynamic that mattered to him.

Michael’s message wasn’t about avoiding conflict by force. It was about how they approached each other—and how his own business had stayed intact over decades. Michael told Nathan that he and Maurice had different areas of expertise and different strengths. so they weren’t trying to prove anything to each other. No dominance games. No need to assert control. Each person just covered different ground.

Nathan recognized the parallel in his own partnership. Jacob has the big ideas, while Nathan says he’s the planner. If they were hiking. Jacob would start walking and figure things out as they went; Nathan would analyze every possible route. Jacob even jokes that they’re like Transformer toys from the 1990s—each with superpowers, and together stronger.

Michael offered another rule that sounded simple until you heard how it was practiced: the friendship between the couples has to come first. Michael and his wife are close with Maurice and his wife, and the two couples even live within walking distance of each other.

When Michael and Maurice started their business together. Nathan says Michael told his own grandmother that the friendship between the couples was always going to come first. Sometimes, that meant Michael didn’t tell his grandmother everything that happened during his day. He never wanted a workplace tiff or disagreement to cloud his wife’s thinking about Maurice.

Nathan and Jacob tried to follow the same discipline. They’re careful about how they talk about each other and the business with other family members. In their household. it’s not just about strategy between co-founders—it’s about protecting relationships so the work doesn’t leak into the parts of life that keep the family close.

For Nathan, the most important consequence isn’t theoretical. He says he knows, “with absolute certainty,” that Jacob has his best interest at heart. He describes it almost like a connection he can’t quite explain—“a telepathic connection. ” he says. with a lot that doesn’t need to be said. Partnerships with friends or co-founders might come close. he adds. but they don’t carry the same foundation they’ve been building since Jacob was born.

And because Michael is in business with his brother, Nathan says their families have been “extremely close.” When Nathan called Michael that day, his grandfather emphasized that working with his brother had been fun and rewarding above everything else.

It’s a legacy Nathan says he’s still aiming to carry forward: build the company, protect the relationship, and leave ego out of it.

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