3 Lessons from our CEO, Leo Bernstein

I was 40 years old when my institutional finance career ended — or, rather, I was offered such crappy opportunities that my pride forced me to admit my time was more valuable than what others were willing to pay for it. My second child had just been born, and I suddenly found myself with increasing expenses, eroding savings, and no real direction beyond forward. 

I wish I could say my next step was strategic, but candidly, it was luck that led me there: I co-founded a real estate investment business. The transition from being an employee to an owner isn’t for everyone, but with no other prospects, I was compelled to make it.  

What started humbly from a single investment evolved into a successful venture with upwards of 1.5M square feet of commercial space that we acquired over a seven-year period. One of the unexpected joys of my unceremonious departure from my previous career was the opportunity to learn new things in a new industry. However, after all that time, I found myself getting restless for a more dynamic challenge. 

I was the partner responsible for overseeing the insurance on our properties. What began as a simple question—why doesn’t anyone have access to their insurance data? —prompted a period of inquiry, which ultimately led to the founding of LineSlip Solutions. Now I get to work with an amazing team to build something of value. 
 
If you're looking for a more exciting challenge and considering starting your own venture, here are three learnings that you should keep in mind: 

1. Take nothing personally, even if it is.   

As a startup founder, you will experience a lot of failure and rejection. You will get feedback on your idea, including but not limited to feedback such as “your idea is stupid.”  Perhaps it is. Maybe it isn’t. Employ those failures and rejections to power your drive. Remember, there are plenty of people who passed on Uber and every other successful startup. You will encounter an incredible number of obstacles, but that means you’re doing it right. 

2. Be willing to take judicious risks. You must go "all in" or you will find it difficult to ask anyone else on your team to do the same.  

If you really believe there’s an opportunity worth pursuing, then go for it. But be smart about how you evaluate the opportunity. We went through many iterations of what LineSlip could do before landing on our current product offering. Once we found product-market fit, we were off to the races. When my commitment to the project increased, I found it easier to build a team that was almost as invested as I am. 

3. Have fun. Life is short and precious. Be sure to enjoy it.

Not everybody gets to experience the privilege of having fun at work, but as a leader, I do my best to incorporate fun into my daily interactions. We each have only one life, and we should strive to enjoy that life, not just slog through it. The key is to have a purpose; it doesn’t have to be grand, but it has to be something you believe in.      

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