How Do You Keep Stress From Crushing You As A CEO?

“I think we should sell the company,” One of our investors said to me.  I was meeting with the investor at his office on Sand Hill Road.

We were in the process of closing our Series B funding.  We had a term sheet from an outside investor that he (and our other investor) had agreed to, so his change of heart took me completely by surprise.

“What?” I responded.  His request made no sense.  We were doing well.  Really well, in fact.

“We should sell the company,” the investor said again, repeating himself.  “We might put in $1M into the next round just to raise the flag (he had previously committed to put in his pro-rata of $3M), but even that is not assured.”

The investor and I went back and forth for the next 45 minutes.  It got pretty heated between us.

Instantly, as I left his office, I felt like a massive, 1,000-pound weight was put on my shoulders.  A sense of dread entered my whole body.

What were we going to do?  An existing investor not following their hand is like a death sentence for a startup that's raising money.

And, making matters worse, the problem investor was arguably the most successful venture capital investor ever in our business segment.  His lukewarm support was really going to raise eyebrows.

I started getting questions from potential investors like, “What does (the problem investor) know that we don’t know?”

It was the beginning of the most stressful period of my life.

Every day for close to one year, I had to live with the possibility of our investors pulling the plug on our company.  All it would take was one bad meeting, one investor saying no, and we were goners.

Talk about feeling the weight of the world on your shoulders.

Talk about fear.

There were times I was so stressed I would go on two to three hours sleep for weeks on end. There were times for days on end when I wouldn’t sleep at all.  There were times when I would uncontrollably shiver even though it was 80 degrees.

There were times when an email from someone (usually our problem investor) would send my heart rate SOARING.   And when I say SOARING, I truly mean SOARING!  I literally felt like my heart was going to explode out of my chest.

I knew there was going to be stress, but this was ridiculous!

This level of fear and anxiety can’t be good for you.  Indeed, constant stress isn’t good for you.  Research conducted by Harvard and Stanford universities concludes that high levels of stress could result in a reduction of people’s lifespans by 33 years!

There’s also the issue of founder suicide.  It’s a real issue.  Venture Capitalist Brad Feld wrote an excellent article about depression and founder suicide.

Does it really have to be this way?

I used to believe that stress was the price you pay for being the leader.  It was like a badge of honor.  My thought process was, “I’m going to take on all the stress of the job, and I won’t complain at all.”

That’s total bullshit!

I was fortunate enough, years ago, to hear Hall of Fame San Francisco 49ers head coach Bill Walsh speak about leadership.  He spoke at length about the pain you need to experience when you lead people.

One line has stayed with me: “When you wake up at 3AM in a cold sweat worrying about what could go wrong, that’s leadership.”  But does it really have to be this way?

I don’t think you can completely eliminate on the job stress.   That’s just not realistic.

However, it is realistic that you develop healthy mechanisms to reduce and manage your on the job (and off the job) stress.

So what do you do to reduce stress?

Before I get into specifics, let’s get real.  We’re never supposed to show our fear, right?  We’re just supposed to silently absorb every punch and happily smile.  “Yes, thank you sir, may I have another.”

Again, I think that’s total bullshit.  Just start by admitting you’re afraid:

•    It’s okay to admit you’re scared.
•    It’s okay to admit you don’t know if your company is going to succeed.
•    It’s okay to admit you’re worried about your family, your team, and your team’s family.

Sometimes showing your vulnerability allows people to rally around you.  You’d be surprised.  I know I have been time and time again.

Let’s go back to my story.  The fight with our problem investor was so nasty that I had to take action or I was in danger of having a serious health problem.  This guy made Frank Underwood (for all of you House of Cards fans) look like a choirboy.

There was so much at stake for everyone involved (myself, my family, the team, the team’s families), and I felt completely responsible for all of it.  The pressure was unbelievable.

I was genuinely worried that I was going to have a heart attack or stroke.  I had to do something to reduce the pressure.

I started journaling about what was going on to relieve some of the pressure.  The journaling helped.

Then, I started searching for other resources to help me.   I found James Altucher’s daily practice.   I found Tara Brach’s on-line meditations.  Then I found Hal Elrod’s Miracle Morning routine.  I started eating healthier.  I had always been an exercise fanatic, so that was already part of my routine.

Each one of these, in its own way, helped me out of the abyss and helped form my own daily routine.  It’s a routine I use to this day.  I find my mindset is much more positive, and I find my stress is reduced.

Here are the five things I do every day to manage my stress:

1.     Have a morning routine. I religiously follow a routine of:

a    Exercise. I go downstairs and do P90X3 every morning. 30 minutes and you’re done.  It’s a great way to start the day and get the endorphins flowing.
b    Meditation. Learning to meditate is one of the greatest gifts you can give yourself. Meditation is called a “practice”, and the practice is keeping yourself in the moment.
c    Visualization. I actually start with this when the alarm goes off. I lie in bed and visualize my day going exactly as I want it to. Then, I visualize my long-term and short-term goals being met.
d    Reading. I’ll take five minutes and read something motivational or positive.
e    Journaling. My journaling is very specific. I’ll write about what will make today great. I find being specific as possible usually leads to good results. Then I’ll write about three things I am grateful for. They can be anything. Today it was the excellent lunch meeting I had yesterday, an email I received from a friend yesterday, and the coffee I am drinking. It sounds corny, but it helps.

2.    Reduce your alcohol intake. Yeah, I know, you need that beer or glass of wine when you get home to wind down. I found, almost by accident, because I wanted to lose weight, that cutting down on drinking at night really helped my sleep. The quality of my sleep became much deeper.

3.    Prepare for the day ahead. Get your calendar prepared, so you know what you’re doing the next day. I like leaving at least 15 minutes between each activity, so I have buffers in case I go overtime on an activity.

4.    Journal at night. Staying positive helps reduce my stress. I write down every night three things that went really well for me today. It helps remind me I’m making progress even when things are bad.

5.    Visualize the next day. When I go to bed, I spend a few minutes visualizing the next day going exactly as planned. It helps me get in the proper frame of mind for the day ahead.

There’s one other thing I recommend that will significantly reduce your stress:

Get a coach or mentor. Having someone you can trust, who’s been there before, who’s got your best interest at heart is a great stress reducer. My friend and mentor, Dave Epstein, was (and is) this person for me.

Dave helped keep me sane more times than I can count during the crisis with the problem investor.

Despite all of your best efforts, there are going to be times that you’re going to be really stressed.

That’s normal, and it's okay.  Just keep doing whatever your daily practice is every day, and you’ll find your stress level will come down.

When you accept the stress that comes with the job, the stress becomes less.

You are not alone.

You may not have a problem investor like I had to deal with.  Maybe it’s a problem customer, or a problem employee.  It doesn’t matter because we all have something that we have to deal with.

You don’t have to face these problems alone, silently suffering.  There are people and resources that can help you.  Please take advantage of these resources.

Resources mentioned in this blog post:

P90X3 –
James Altucher/Daily Practice:
Meditation/Tara Brach:
Miracle Morning/Hal Elrod:
Journaling/Five Minute Journal:
Brad Feld:
Suicide prevention lifeline: 1-800-273-TALK

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Pictures: Depositphotos