What Is It Really Like To Be A Startup CEO?

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My heart is beating too fast, and it won't slow down.

It’s 3AM, and I can’t sleep. Again.

I get out of bed, and I walk to my office. I am shivering even though the temperature in the house is 72 degrees – nerves. I turn on the computer, and I check my email.

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No email from the new investor like he promised. Why can’t these guys do what they say they are going to do? Why?!?

3:30AM: I head back to bed. At least I didn’t wake up my wife. Maybe, now I can get a little sleep before the alarm wakes me.

5AM: The alarm goes off. I had just fallen asleep, and now it goes off!

OK, I get up and go workout downstairs. The exercise will do me good. I am shivering as I walk downstairs.

6AM: I finish the workout. I shower, shave, have my protein shake, read the paper, and answer some emails.

7AM: I kiss my wife and daughter goodbye, get in the car, and head to work. Even the bad days are good, but I don’t know how good this one is going to be…yet.

Steve calls. It’s always good talking to Steve. We talk about what’s going on his life for a change. It’s a good distraction.

7:30AM: Starbucks. You’ve gotta love it – a Starbucks as part of a gas station. You can fill up your gas tank and your internal caffeine tank at the same time. Genius!

7:45AM: I'm in the office. I respond to emails and make some phone calls.

9AM: Meeting with a potential investor, a legend in the VC industry. He says to us, “I hate high-margin businesses!” That might be the stupidest thing we’ve ever heard raising money.

I just smile and continue with our presentation. There’s no hope in hell we’re getting his money.

10:30AM: Phone call with another investor. “Brett, we should have a term sheet for you by the end of the day.” How many times have I heard that?

“Great,” I respond.

11AM: Operations meeting. Dave and Shoba are just killing it. Demand keeps increasing, and we are meeting it.

The feeling of starting something, nurturing it to grow, and seeing customers buy your products is indescribable. Watching your team and fellow employees feel empowered to make things happen is a great feeling.

I need to secure that funding, so they can be fully rewarded for their great work!

12PM: I really want to talk to someone inside the company about my fears and concerns. It's oh so tempting when you are down, but you can't go there.

I’ve got to take a walk, leave the building, or do something. I can’t share my worries with the employees.

I decide to go for a walk around our “campus”. It’s 75 degrees outside and I am still shivering. I wish the shivering would go away. It won't.

1PM: Traffic meeting. Review with Mary, our PR person, the status of our various advertising and marketing campaigns, and our collateral development. The beautiful thing about today’s world, unlike the bingo-card world I started my career in, is that you can measure everything – and we do!

Oh, how I love it! Website traffic is rising. Sample requests continue growing at a high rate. Design wins are increasing, and so is revenue. Mary and I eliminate the ads that aren’t converting, schedule new ads, collateral, videos, and blog posts.

3PM: Company meeting. Remember, Brett, you need to say what don’t mean as well as what you do mean. The team will fill in the blanks if you don’t.

The meeting goes well. I update everyone on the status of the fund-raising, sales, and new product introductions. The team, as usual, had great questions.

5PM: I’m in my office. Someone on the executive staff let me know that a member of his team was worried because I frowned when he asked a question about how sales were going.

“I frowned? I don’t remember that.” I was laughing, but it was a sober reminder: Every word, every gesture, every frown, every time you raise your voice, every time you leave the office early, every time you leave the office late, every time you arrive at the office early, every time you arrive at the office late, everything you do is analyzed by the employees.

“I’ll say something about that next time I speak to the team.”

Next time.

5:45PM: I check my email. There it is!

Subject: Term Sheet


My Partners and I are pleased to present to you this term sheet….”

Euphoric, I print out the attached term sheet.

I walk out of my office and scream, “YES!” at the top of my lungs. I then jump two feet into the air, vastly outperforming my vertical leap at the draft combine. (Yes, that's a joke.)

Not bad for a 40-something year old, I think to myself.

I start reading through the term sheet.

Oh, please. Why did you add that term? Why!

Another problem.

Why can’t anything be straightforward? Why?!? How are we going to solve this?

I call our lead investor, and we agree on a strategy to solve the problem. It should work if the new investor is reasonable. That’s a big if in VCland.

I have to find a way to get this round closed.

You are responsible, as CEO, for the lives and wellbeing of your employees and their families. It's not about you. It's about them. I have to find a way.

7PM: I pack up my briefcase and head home. Traffic usually thins out when I leave the office after 7PM, but I check Waze just in case. Good. I can take 880 to 280 to get home tonight.

7:30PM: Home.

My wife, daughter, and I have dinner. My wife and I help our daughter with her homework after dinner.

9:15PM: My daughter just went to bed, so I catch up on email and work that needs to get done.

11PM: Bed. I know I will fall asleep quickly. The question is will I stay asleep?

3AM: I wake up from my nightmare: we couldn’t close funding. My wife is sound asleep next to me.

I am shivering even though it is 72 degrees. I hate the shivering. God, do I hate it.

I get up and go to my office, and turn on the computer to check my email.


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