Advice for Founders who want to stay the CEO

Hey CEO & Founder, congratulations on closing your Series A.  You now have a company to build and run not to mention a shit ton of capital to return to investors (who are not as patient as you think).

Don't worry about never being a CEO or manager before, it's EASY!  Anyone can do it - that's why so many founders stay in the role for their whole careers (I'm kidding, not kidding)


There's all types of great CEOs and every one has differing operating and management styles hard built over time that help them execute and drive a company towards success.  Warren Buffet.  John T Chambers.  Jack Welch. Larry Page.  Howard Schultz. David Olk.

Founders with successful companies that have raised legit capital, however, are normally thrust into the role after limited experiences ruling the roost.  As a result, they either:

  1. adapt, learn quickly, and execute; or

  2. check their egos at the door and move into a role more suitable to best add value and help the company; or

  3. under perform and get fired / transitioned involuntarily

If #2 just isn't happening (because you have daddy issues and want to label routers "CEO's WIFI") and you want to avoid #3, here's a very high level primer on wtf is expected of you as the CEO of a fast growing company at the very minimum.  There are four key components:

1. Develop a short term and long term strategy


Good CEOs develop and make decisions to set a long term and short term strategy that helps the company achieve it's long term vision.  Someone has to have the long term vision, but good CEOs are great at putting plans in place that navigate a competitive landscape, changing industry, innovative product, and distribution and customer acquisition strategy so the company can execute.  The short term strategy is tweaked when it needs to be based on the motion of the ocean while the long term strategy is the north star.

2. Hire experts, make them commit to plans, hold them accountable, and put out the fires

This is primarily what CEOs do day to day.  It's how they keep the trains running on time and how they grow the business.

Step 1:  Hire and recruit amazing people.  Functional area experts that can scale each area of the business. Good CEOs are the best recruiters you know.  If your team won't let you come to the dinner when they are trying to recruit someone, then you need to work on this area FAST.

Step 2:  Get these people to commit to goals aligned with a plan that's calibrated with the above short term strategy.  No one dances with the Head of Sales better than the CEO.  One tries to sandbag the other while they both try to move immovable objects with their minds. It's fascinating to watch.  

Step 3: Constantly meet with these people to make sure Step 2 is happening. You've heard the term 1 on 1, that's what this is.


Good CEOs put out fires along the way and set a cadence for weekly and quarterly meetings where decisions are made (which always have structure, goals, minute taker, and no rabbit holes).  Their team trusts them and they trust their team - there's a real arrangement of transparency, accountability, and honesty (versus bull shit and political smoke blowing).

I hate hanging out with CEOs of great companies - they constantly get me to commit to shit and I don't even realize it's happened until it's too late.  Then I'm always trying to impress them and execute.  It's so annoying.

3.  Never run out of money

Great CEOs never run out of money.  They quickly cut costs if there's a misstep.  They know it's always easier to hire someone than fire them. They are also extremely capable at raising equity because they are well networked and well liked in the investor community. They know how to sell the vision and support the strategy with numbers.  They are amazing at taking an inordinate amount of information and dumbing it down to tell a very exciting story that elicits a "hand to pocket reflex".  They realize that as the company raises more money the investors become more sophisticated - so their process ALSO becomes more sophisticated and numbers focused.  They know how to tell the "right" story with the numbers when a raise is "all about the numbers".  CFOs raise debt - GOOD CEOs raise equity - and if they can't, then they inspire great bankers or others to help them while managing them closely. If someone else at the company raised all of the money, then they do everything possible to make sure this person is protected, as happy as possible, and never ever leaves - because if this happens they are screwed.


4.  Manage the board 

Good CEOs manage up.  The larger the company gets, the more time they spend on just this area.  It looks something like this.


They over communicate to the board so that they know what's going on and so that the board believes they are helping and being heard.  They are also able to balance the board getting in the way while helping them make the best decisions and get to the right conclusions with accurate information that's based on factual evidence (versus back channeling). They don't let board members hook onto limited pieces of information gleaned from one off conversations, articles, or experiences to form inaccurate conclusions. Good CEOs protect their team if there's ever friction between an exec and a board member - and they work hard to remove that friction and achieve common ground.  Good CEOs socialize with each board member individually so they understand when there might not be consensus on critical matters.  Good CEOs run effective board meetings that are organized and well prepared for - they use these meetings as a catalyst for achieving a key goal.  Boards are never surprised by anything when there's a good CEO - good or bad.

To sum it up, if you are going to be the CEO, your job is to hire, inspire, retain, never run out of money, and manage the board while above all else HIT YOUR NUMBERS (yes, CEOs operate against expectations called "budgets".  Fascinating things these numbers in boxes).

It's pretty straight forward and anyone can do it.

David Olk