How The “CEO Manual” Came To Be With Trey Taylor

Welcome LinkedIn friends! Your weekly insight to grow your relationships and book of business.

I had the pleasure of interviewing Trey Taylor, J.D. , author of A CEO Only Does Three Things, as well as the M.D. of Threadneedle, the Taylor Family Office, C.E.O. of Taylor Insurance Services, M.D. of Trinity | Blue Consulting, and Founding Partner of Ascend Partners.

Mo asked Trey:

“So Trey, why don't you drop us right into why you wrote your book, A CEO Only Does Three Things? Why does somebody run a business, and how do they do the things that are uniquely what they should be doing? And how do these decisions make a big difference freeing up time?”

Trey responded:

“There’s a ton to unpack there, Mo. I appreciate the question. As far as the origin story, you know, I grew up in a family where we were all entrepreneurial. My grandfather had started our family business, which is an insurance, financial planning sort of brokerage business. That business has been around for about 58 years. So I'm a third generation.

So I got into that business in a bit of the backdoor roundabout way. My dad had always told me, “Don't do what we do for a living, you know, you're always dependent on the client. You shouldn't do that.” It's a very second generation thing, also, to take the third generation and send them down the professional track.

I went to law school at Tulane and really hated every moment of the study, but I really enjoyed the problem-solving and the hacking; that sort of became more of the way they structured your brain to think than the material that you were learning. I really enjoyed that.

I was doing a clerkship in the summer and was hired by a guy who then left and went to a company that no one had heard of but later became WebMD. So when he got there, I was in my third year of law school when he called me, and he said, “Hey, why don't you come work for me at WebMD? I don't have a law career. I need somebody to help me out.” I was thinking at the time, “What are you talking about? I go to law school in New Orleans, you're in Atlanta.” And he said, “Just transfer and make it happen.” So I did just that.

That sort of launched me into a career in venture capital, early-stage investing. We would do a deal on Thursday. Then, Friday morning, it would be the front page in the New York Times, or The Wall Street Journal, or something of that nature.

It was a really good sort of graduate education in corporate development, business development, venture capital, and those kinds of things. That became my passion and my trajectory.

I left that company to start a venture fund; we've made 11 investments, one of which I still get dividend checks from, and the other 10 all reached a successful exit. It was an incredible track record. I took a job after 9/11 when venture capital basically disappeared from the southeast. I took a job at Earthlink, which was an ISP, and we revamped their product development strategy by interfacing with my contacts in venture capital.

I was taking these skills and applying them in weird places. A friend of mine at Earthlink got hired at AOL. The CEO of AOL said to him, “We need to find somebody to divest from all these companies that we thought, and we need to raise a billion dollars because we're not doing anything with these companies.” And they owned the HuffPo, movie, phone Moviefone, and all kinds of weird, random things that they should have put together, but they never did the integration work.

So I took that job. I was standing out in front of my house when the movers called and said that they were coming to get my stuff to move me to Virginia. Right then my mom called and said, “Hey, we're in Vegas.” I had known that they had gone at the end of the year to see some family and enjoy some nightlife, but she said, “Your dad's in the hospital, and it doesn't look good…” So my brother and I, you know, ran to the airport, went to Vegas, and brought my dad home, not in the way that we wanted to bring him home because he passed away.

Then, you know, my dad was 52 years old, and we had no succession plan in the business; the succession plan was for him to live to be really old and somebody else to take it over. And that didn't happen. So I decided that I had to stay.

I had to call my boss at AOL and say, “I'm not taking the job, can I have my furniture back?” I owed him money because they had given me a signing bonus and all of that. So, I'm standing in a business that I'm not supposed to be in, I have no affinity for, that I have no passion for. It's a commitment of obligation, not of affirmation. It was a lot of head trash for me for many years to stand there, but the first thing I did after I announced that I was taking over was close the door and literally Google, "How do you be a CEO?"

I was very unsatisfied with the answers that I had received there. So what I began to realize was the CEO is the only person that doesn't have a job description in the business. You may have a job description for your, you know, VP of product development, or your Director of Logistics or something of that nature, but inside that job description, do you tell them how to lead the organization that they are on top of?

So after several years of taking notes, as I learned lessons, most of which were mistakes that I had made, I began to synthesize those things and figure out that one of my favorite VCs had nailed it when I had met him once before. He told the story of having a fire the CEO of one of their portfolio companies, which is a remarkably hard thing to do. In doing that, he looked at the chairman of the board and said, “I need to hire a CEO, but I don't know what they do.” And to this, the Chairman said, “Oh, that's easy. They hire the right people, they keep enough money in the bank. And you know, they build a culture or a workplace where people want to come and do excellent work.”

That's culture, people, and numbers. So I wrote my book at the request of many consulting clients. My early intentions were simply to have a document that I could pass on to the person who took over for me, you know, so we wrote the book, A CEO Only Does Three Things. CEOs often look at that and say, "Yeah, right, I wish I only did three things."

My argument is that before you touch anything else, you should make sure that you're making a contribution to the culture in a positive way and that you're making a contribution in either recruiting or retaining staff members. You have the people on the journey with you. You should check in with your numbers to make sure you're making the correct progress and get them or to make course corrections along the way.

So, I think that also holds true for anybody in a position of leadership. Those should be the first three things you do every morning. When you sit down and say, "Let me address my business and my work life", those are the things that we should go off of.”

Dive deeper into the conversation with Trey Taylor here.

Trey reflects on his journey from unconventional beginnings in the business world to the unexpected responsibility of becoming CEO.

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Thanks for reading!

-Mo