From prestigious finance careers to launching a startup revolutionizing the humble umbrella, Reed Jacoby's entrepreneurial journey demonstrates that sometimes the boldest business opportunities aren't flashy tech innovations but overlooked everyday problems.

Reed's story begins in Michigan, where despite not being the academic superstar, he leveraged his natural talent for building relationships to secure admission to top business programs and eventually land coveted positions in banking and private equity. Working with ultra-wealthy clients gave him a crucial insight: true wealth creation doesn't come from collecting paychecks but from ownership. One pivotal moment—a client casually calling to wire in $22 million—sparked Reed's realization that he needed to create something of his own.

The entrepreneurial path has tested Reed's resilience at every turn, especially during fundraising where "it's probably one yes for every 50 to 200 no's." Through it all, he's maintained that this journey, while "by far the hardest thing I've ever done," is also "one of the most rewarding things you can do."

Ready to reconsider what entrepreneurship might look like in your own life? Reed's advice is refreshingly honest: find something that genuinely excites you, recognize it will take longer and cost more than expected, and prepare for constant challenges. Most importantly, know yourself—some people need to "burn the boats" while others can start more cautiously. Whatever your approach, Reed's journey proves that with enough determination, you can handle far more than you think.