1 year at Cisco Systems hardware engineering internship, 1 year at a mobile startup before mobile was really a thing, 8 years at Goldman Sachs in their electronic trading business- business side, 1 year own startup, 3 years electronic trading startup, now- building this out.. <a href="https:&#x2F;&#x2F;news.ycombinator.com&#x2F;item?id=11441020" rel="nofollow">https:&#x2F;&#x2F;news.ycombinator.com&#x2F;item?id=11441020</a><p>1. Don’t be afraid to start over. The problem with largely starting my career at Goldman Sachs was that you feel like you’re running so hard&#x2F;fast with blinders on. Also, and maybe this is a New York thing, I started to identify myself with my job. I had to learn that I am not my job. All of this made switching friction very high. In my time at GS, Facebook was being created, and Google became what it was today.  In reality I was letting the outside world evolve, while I sat somewhere that refused to. I felt like everything I had “built”, career-wise, would fall apart the day after I left Goldman. The reality was that my career didn’t fall apart. But the products&#x2F;businesses that I built meant less to me, and I was more excited about the future of what I wanted to build. I felt finally unchained. I should have left 4 years before I did.<p>2. Keep closer to technology. When graduating in 2002 with a Computer Engineering degree, I heard people around me snicker -“Didn’t all those jobs just get outsourced?” It was a bad time for technology, it was a bad time to graduate with a computer engineering degree. Because of my career choices, I ended up focusing more on the business end of things (which still worked out well), but technology is my first love. I love to build things. Now I just do it for fun and hope I can build stuff that people find useful.<p>3. Be less afraid to fail, take more risks when you can. I played it safe when younger. Focused on making as much money as possible. I love the Elon Musk quote - “Failure is an option here. If things are not failing, you are not innovating enough.”