Leo Bernstein arrived at Amherst with a fear of failure that shaped his academic choices and early career. A layoff at the age of 40, however, forced him to reset. He made a big bet on himself, starting a commercial real estate business that invested in properties the market had overlooked or undervalued. He then founded LineSlip, a software-as-a-service (SaaS) platform born from his frustration with the opaque world of commercial insurance. In the process, he learned to see risk not as something to avoid, but as a necessary ingredient for growth and resilience.
We also talk about Networking as a Skill, the workshop he created with our classmate Rob Bernstein to help younger people build stronger professional connections, and the rooftop apiary he built with his son, a project that’s become a surprisingly rich source of metaphor and reflection.
Contact Leo at leo@lineslipsolutions.com.
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