Archive: Lessons Learned

  • Pain is Where the Learning Happens

    April 5, 2019

    “Resisting pain only increases its intensity.” — Chogyam Trungpa I am 47 years old and I have made a lot of mistakes in my life — both professional and personal ones. I hope I make many more. It’s true. I have hired the wrong people on my management team. I have taken too long to fire people after I realized

  • 10 Lessons From A Recovering #Insurtech CEO, Part III

    July 31, 2017 In the late ‘90s, I was among the group of entrepreneurs forging the next generation of dot com companies. I was, fortunately, selling technology tools to most brick and mortar enterprises looking to join the e-commerce club. It was a time of incredible growth for me. I learned a lot about enterprise

  • 10 Lessons From A Recovering #Insurtech CEO, Part II

    July 16, 2017

    One time, early in the life of my company, I sat down with the CEO of one of my customers and asked her to help me connect with other senior leaders in the insurance industry. During my visit, I brought a list of folks I would like to meet. She reviewed the list for a