CEO Shoptalk — Great Startup CEO

Are you a great startup CEO?

OK, so the Big Red Car gets asked often, “Tell me, wise and red Big Red Car, what makes a great startup CEO?”

Like most things in the startup world, there is not a single, correct answer, plus the Big Red Car is lazy and doesn’t want to do the work.

But, now somebody asked the question in a way I cannot dodge. So, here goes.

What makes a great startup CEO, Big Red Car? Tell me.

What makes a great startup CEO, Big Red Car?

Vision, values, culture

The CEO must originate the vision and own it.

The CEO has to inculcate the organization with her values and make those values the foundation of an emerging culture.


When the game is on the line and everybody is in the huddle wondering who is going to take the last shot, the CEO says, “Hold my beer. I’m the leader here. Give me the ball.”

Be a leader even when you have no idea how.

Be a lion.

Be “the” product advocate

Own the product even when you delegate important aspects of it.

Understand where the product is at all times.

Take the pain, share the credit

When the organization is hurting, looking into abyss — absorb the pain. Take the blame.

When the organization is on top of the mountain, spread the credit.

You get all of the pain and none of the credit (ahhh, but you get the biggest slice of the equity and equity is the best pain reliever known to mankind).

Hire great people

Do not be afraid to hire the best of the best even when they validate how little you really know. But, you knew enough to hire them.

Don’t sweat domain knowledge

Go into that dark night knowing you can always rent domain knowledge. When lost, you don’t have to know exactly how GPS works.

Hire, rent domain knowledge.

Be the sole conduit between the company and investors/board of directors

Raise the money. Form the board. Be responsible for managing the company’s relationship with them.

Never get mad at the money. It will change its mind.

Do the dirty work of raising money

Learn, learn fast

You don’t have to know everything, but you have to know what you know, know what you don’t know, and realize there is stuff you don’t know that you don’t know.

Fill the gaps with learning. Learn from the domain expertise. Hire great people. Hire/rent domain expertise, but learn, learn, learn.

Be unafraid to say NO

The two best answers in life are a quick YES and a quick NO.

Learn to say NO. Quickly. Perhaps, often. Don’t equivocate.

Energy is lost waiting for an answer.

Be able to do strategy, tactics, objectives

Strategy is the view from 30,000 feet. It guides the entire enterprise.

Tactics is the view from 10,000 feet. It guides the departments and disciplines.

Objectives is the boots on the ground view.

Be able to take strategy, spit out tactics, develop bite-sized, easy-to-understand objectives.

This is a skill. People are overwhelmed by strategy and tactics, but if you give them clear objectives, they will work their butts off for you.

Be ready to deviate from the plan

Do not be rigid or stubborn. Be ready to call a game day play. Do not apologize.


Everyone hears about 53.2% of what you tell them. Make them brief back what they heard. They never get it right on the first attempt.


Every month during startup, answer questions about anything. Force people to ask the tough questions.

People will bail water faster if you tell them you are sinking.

People will follow the honest broker who tells them the truth.

Motivate, inspire, drive through the hard times

When things go wrong is when the team needs motivation and inspiration.

Do it during bad times and it will be easy during good times.

People want to see the look on your face when you look into the abyss. They will act like you act.

Yell “calf rope”

As a CEO, you need help also.

Join professional organizations wherein you can obtain comfort and succor from peers.

Get a professional CEO coach when you are ready.

Be unafraid to be mentored.

Find ways to blow off steam and actually do them.

Be genuine, authentic

Do not mislead yourself. Do not mislead others.

Speak from the heart about what the people care about. Their first concern is your meeting the payroll. Never forget this.

Be real. Be genuine. This will make you authentic.

And, there you have it, dear reader. The Big Red Car harnesses 40 years of CEOing, leading, and answers the question you ask — what makes a great startup CEO?

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car, y’all. Now go bite the ass off a grizzly bear.