Keith Cowing

Keith Cowing

Entrepreneur. Career advisor.
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February 4, 2016


There was a famous food test where critics were given three meals: chicken, grilled chicken, and Tuscan-seasoned balsamic chicken. The Tuscan chicken got the best ratings. But there was a twist. The three meals were identical except for the name. The critics’ brains literally told them that the Tuscan-seasoned balsamic chicken was tastier than the identical “grilled chicken.” The name evoked positive emotions that changed their physical experience.

This is an important concept to remember when designing product experiences. Let’s use Starbucks as an example. Starbucks customers love getting to work in the morning feeling like they are powerful and ready to take on the day.  Nothing evokes that emotion like striding down the street holding a caffeinated beverage in a signature Starbucks cup. On the flip side, Starbucks customers hate when days get long and stressful. Therefore they love having a sanctuary where they can take a 15-minute break in the afternoon. Think about the music, the smells, the baristas, and the entire environment inside a Starbucks. It is designed to evoke emotions so when you sip your coffee, it feels like the best part of your day.

Think carefully about your customers. Figure out what they hate and what they love. Then take advantage of that to evoke emotions and win their loyalty. If people buy your product because it’s rational, you can win for now. If people buy your product because they love it, you can win for a lifetime.

January 14, 2016


There is something in the startup world, and elsewhere, that I see all the time.  It seems like the right thing to do, but there is no better way to kill your chances: the generalist pitch.  Here is a quote from an email I got recently: “I would be open to any position that would allow me to gain valuable experience and grow within the company.”

I see this a lot and I NEVER see it work.  Here is the problem.  This describes what you want.  It doesn’t describe what the company wants.  The company wants a marketer who has been fine-tuning their marketing skills for years and an engineer who loves coding and can talk database optimization for hours.

I like to compare it to a football team.  You might come in and say “I just want to play football.”  But in reality there are 2 job openings:

Lineman: You need to be strong, aggressive, 6’6″ and 350 pounds.  It doesn’t matter if you can run fast or catch the ball.

Wide receiver: You need to be lightning fast and have great hands.  It is not important how well you block or tackle.

It doesn’t matter which one you want to be, but it is important that you commit to one or the other.  Anybody who says “I’ll do anything you have” has already tipped their hand that they can’t compete against the linemen or the wide receivers.

My philosophy is to commit to being a wide receiver or a lineman, build the relevant skills, and then go hunting.  Let’s say you go to 10 teams.  5 won’t have an opening for that position and won’t meet you (which is fine), 5 will have a relevant opening and meet you, 3 will seriously consider you, and 1 will give you a job offer.  Alternatively, you can optimize for the initial conversation and say you’ll do anything.  Then all 10 will meet with you but 0 will hire you. So go for the kill and optimize for 1 job offer vs. 10 conversations.

It’s OK if you don’t know precisely what you want to do for the rest of your career, but the more you focus and describe how you will make the company better, the higher your chances. Don’t say you’ll do anything.  Tell them how you will help them get more customers (sales/marketing), improve the product (product/design/engineering), or run the company (recruiting/operations/etc.).

December 4, 2015


I am excited to announce that I have joined the product team at Flatiron Health.  I recently decided to make a change and pursue one of my passions in either health or education. After exploring opportunities,  I came away deeply inspired by the people and mission at Flatiron. The team is tackling one of the most epic problems in healthcare: helping oncologists and researchers provide better care for cancer patients.

As I thought about my career and my decision, I wanted to share a few thoughts about why it’s important to tackle the most epic problems.

It maximizes your impact

Choosing important problems can be viewed in the absolute sense (cancer) or in the relative sense (the most important problem that your team, division, or company faces right now).  Look for roles at companies that are doing things that matter to you. Then consider it part of your job to get yourself on high impact projects, even though it’s not directly in your control. This means being transparent about your career goals, seeking visibility from executives, and asking to join projects that will help you grow.

When times are hot, you can still recruit

Regardless of your role, you will hit a point in your career where your ability to attract top performers will be critical to your success. In crazy markets it is hard to attract talent.  Top candidates will have four or five offers and will always have an option that pays more.  If your pitch is not focused solely on compensation, but on the potential to make an impact, you can still win.

When times get tough, it’s still worth it

Let’s be real.  Things will get hard.  You will have days when everything goes wrong and you want to throw in the towel.  When you’re working on something meaningful, it’s easier to muster up a second wind and power through.  It’s important to work on something that helps you keep your chin up during stressful times.

There is nothing more satisfying

Working on big, hairy challenges is simply fun and exciting. When you turn 80 years old, will you regret the decisions that you’re making today? We can’t predict the future. But working on important problems paves the way for a satisfying career.

“Work on something so important that even if you fail the world
is better off for you having tried.”

-Tim O’Reilly

P.S. Flatiron Health is hiring!  Come join me

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