Why Jason Jacobs started Runkeeper

As a follow up to my post a few weeks back about why founders create their companies, I’m delighted to share Jason Jacobs story with you all today. 

Jason is the founder and CEO at Runkeeper and we are proud investors in his company. Jason is a tireless entrepreneur. His passion is authentic and infectious. 

Here’s Jason’s own words about his story.

* * * 

When Bijan asked me to write a blog post about what the motivation was to start RunKeeper, I thought it was timely since we are approaching the 5-year anniversary. In June of the day we were incorporated – great time to look back and reflect on the journey so far.

I had known for a long time that I wanted to be an entrepreneur. I was the little kid in my neighborhood growing up who rounded up the other kids after a snowstorm to go around shoveling people’s driveways and undercutting the price of the snow plows. I was also the kid who went to almost every small business in my hometown selling ad space in our hockey tournament program. While the extra spending money was nice, my real motivation was much more the sport of it and the feeling of accomplishment when I experienced success.

A year out of college, I joined a software company that had around 100 employees. When I left two years later, they were more than 700 employees and publicly traded. While the bubble burst and the company came crashing back down to Earth, this experience was a phenomenal learning opportunity for me and I knew then that I wanted to build enduring technology companies from small to very big for a long time to come.

From then on, I viewed all of my professional experience as ‘practice before the big game’. I had yet to come up with an idea for a business I was really passionate about, and I figured while I waited for the right idea to come along, I would continue to build up my skill set so I would be better equipped to bring the right idea to life when I found it.

It took me several years to lock in on the ‘right idea’. I hoped that whatever company I started would be one I built from small to very big over a number of years, which to me, meant it had to be an important problem that I was deeply passionate about solving in a big market. Other than building technology companies, I didn’t know what I was passionate about at the time, which made for a grueling process.

I would come up with idea after idea that seemingly met all of the criteria, but in hindsight, they were all missing the most important element – passion. I was so frustrated with the vetting process that I signed up for my first marathon as a way to stay sane as I figured out which company to go and build. It was during this marathon training that the idea for RunKeeper came to be.

With all of the innovations coming in mobile, health/fitness sensors, social networking, etc., it seemed there was a big opportunity to build a simple, social, fun digital fitness platform that tied together all of this disparate health/fitness data into a single, cohesive experience.

This was a huge breakthrough for me on multiple levels. The biggest breakthrough was that I discovered a deep passion of mine that had been with me my whole life – healthy living! I realized then that I wanted to build a big company at the intersection of fitness and technology. The funny thing is that I came to realize this as I went out on 20-mile training runs, wracking my brain along the way about what I was really passionate about. Plus, this hypothesis of a simple, social, fun fitness platform for the masses felt like a solid, well-timed starting point.

I got to work right away, and quit my job a few months later to focus full-time on building RunKeeper. Five years later, we have an awesome team of almost 40 employees, $11.5m in capital raised, over 16m users, and we are just getting warmed up!

While it was a grueling process for sure, I am very glad that I had the patience to wait until it felt right.

Founding CEOs

There is no question that I prefer to invest in startups where the founder is the CEO. 

A few years back, Ben Horowitz wrote about why startups led by the founders are best. I completely agree. At this time, every board I’m serving on has a CEO who is also a (co) founder. 

In addition to all of the many reasons Ben listed, I would also add a few. 

-founders as ceo are the best at recruiting. it’s their mission and no one can tell the story like a founder

-startups go through severe ups and downs. losing a big customer, losing a key employee, seeing their stock price fall or worse. lots of reasons why morale is beyond tricky in a startup. loyalty to the founder is a key thing that keeps the team together through good and rough times. 

-founders are the soul of the company. their instincts are what brought us altogether in the first place. they drive the vision. you can feel them in the products they have been dreaming about. 

There are other reasons why I prefer founder led companies.

But that actually isn’t the purpose of this post. 

This post is about why founders lose their job as CEO.

It’s often not discussed too often, if ever, so I thought I’d start about why it sometimes happens. Here are a few different scenarios:

0. Sometimes a founder doesn’t want to be CEO. I’ve been on boards in the past where the founder doesn’t want the job. The founder just wants to focus on product and wants someone else to run the company. 

1. Board members believe what works in one company must work in other companies. They try to transplant the same system into all companies. “our other young founders need an experienced coo” or “a coo is the worst idea”. See what I mean? Each startup is different and what works in one company may not be the best approach for another. 

2. Board members believe in the silver bullet. “all our problems go away if we can get a world class operator”. As bad as it sounds as I type those words, it sounds even worse to hear it in a meeting. 

3. CEO loses the confidence of the board. When the CEO makes promises and consistently doesn’t meet those promises, board confidence is at risk. The best way to deal with this is to speak openly and honestly between all members of the board with the CEO. This will help address whether the CEO is problematic or there are other issues at hand.

The worst way to deal with it is to stop making promises or to dramatically lower expectations beyond what is reasonable or useful to the company (the latter is known as putting ones own interest in front of company interest). 

4. But the absolutely hardest & most painful scenario is when the team loses confidence in the founder/ceo. The management team goes to the board and basically says, “we don’t believe anymore and can’t work for this ceo”. This becomes a very dire situation and essentially the board has to decide if they go with the team or the founder/ceo. 

It’s painful for many reasons. Often the founder/CEO doesn’t see it coming. The team hasn’t been willing or effective in getting their message across and had to trigger the nuclear option. And if the board chooses to support the team then they must protect them as well for the good of the company. 

Scenarios 1-4 are all difficult and hard. You never want to lose the founder’s leadership. That’s why early stage investors got in business with the company in the first place.