The CEO Chronicles

Lessons Learned From A Serial CEO

Why me?

I have spent the last 20 years as a serial CEO of multiple healthcare startups, as well as spending the last 3 years as a corporate/strategic venture capitalist. I have made many mistakes and gotten lucky on more than a few occasions. What I hope to accomplish in this blog is simple: educate and, on a good day, entertain. There are many that are much, much more successful than me (nearly everyone in Silicon Valley!). There are some that are worse (also in Silicon Valley...e.g. Elizabeth Holmes re: Theranos). I am not from Silicon Valley. If you have questions, comments, or suggestions (future topics), please feel free to reach out to me.

Why now?

Entrepreneurship is thriving in the USA. It has never been a better time to take the leap and start a company. I am seeing an incredibly diverse and youthful group of founders (as well as many seasoned, old geezers like me) embark on what is arguably the most difficult job around. I have spent a myriad of hours counseling startup founders and CEOs on pitfalls to avoid as well as creative (and some not so creative) ways to solve common challenges that they are facing.

Did he really stay at a Holiday Inn Express last night?

So what "sage" advice (you have probably seen this same info a million times in other blogs...) should I impart with the kick-off of this blog series? Let's start off with some of the basics:

1. Do your homework: I am always surprised at how many people come up with a great idea, but fail to do the basic due diligence. Remember that your great idea is only great if someone is willing to buy your stuff for a price that can generate a strong profit. In other words, it solves a real problem that people/businesses are willing to pay a price that is profitable to your company. Interview 10, 50, or 100 potential customers about your idea, your pricing, and the problem that it solves. Take copious notes. Will doing that take a long time? You betcha. Will it be a pain in neck to complete? Yup. This will be the first (of sooooo many more to come!) test to see if you have the stamina to start and run a business.
2. Prepare for the long haul: Starting a business never goes according to your initial plan. It always takes 2x longer and 3x more money than you originally expected. Understand that this is "normal" and that you have to be prepared to slog it out in order to realize your long term vision for your company.
3. Expect the unexpected: Many, if not all, of your original assumptions will be wrong. Be prepared to pivot, quickly. More importantly, be receptive to the signs that indicate you need to pivot. Many entrepreneurs ignore these signals. If your results are not what was expected/planned, be brutally honest with yourself/your team and recognize your current reality.
4. Understand the role of luck: Yes, Luck = hard work + preparation (most of the time). Sometimes, good luck just happens. Same with bad luck. One example of bad luck was when I was CEO of a medical device startup back in the early 2000s. I had been CEO with nearly a decade of 80 hour work weeks behind me for this company. We had just closed on a $20MM round of funding from one of the bluest blue chip VCs in Silicon Valley. Several months after that investment, a publicly traded biotech company offered us $200MM to buy our company (the IRR for our new investors would have been insane!). We had "passed" all of our deep due diligence examination from this biotech firm. But, at the 11th hour (literally), the CEO of that firm called me to let me know that the deal was falling through. He was being forced to terminate our acquisition due to some bad news that was going to hit the front page of the Wall Street Journal the next day. That firm was being hit with a $425MM fine from the government. Ouch...just like that, $16MM of capital gains income evaporated for me, personally, in an instant! There is nothing that I could have done to have prevented that particular outcome. Sh*t happens. That outcome was not a reflection on me, my team, or the opportunity.
5. Don't be a pain in the neck: If you are lucky enough to get a first presentation/meeting with an investor/VC, understand that the goal of that meeting is to get the next meeting. Don't try to close an investment on your first presentation. VCs take time to make investment decisions. Follow up in a timely and professional manner. But, do not hound those investors incessantly for follow up or feedback. That will just annoy them. It will give them pause as to whether or not they will want to have a long term relationship with you and your company. Also, do NOT send very long emails (either via email or Linked In). Pithy messages are appreciated. Tomes are loathed.
6. Stay confident: Investors are going to push you (sometimes aggressively) to justify nearly everything you think/believe/tout about your company. Know your stuff and remain poised during their inquisitions. Don't take their criticisms personally.
7. Stay humble: Investors can oftentimes be arrogant. You should be humble (see https://www.jimcollins.com/concepts/level-five-leadership.html). Insert mic drop...no, wait...one more thing...
8. Dream big, but act practical: Big dreams can change the world, but practical execution and disciplined management ensure those big dreams become a reality.

As always, I welcome your comments, questions, and suggestions (e.g. other topics for me to opine).