A Recently Exited Founder on Surviving the Contradictory Role of Startup CEO

This is a guest post from Rob May, a co-founder and CEO of Backupify, which raised $19.5M and sold to Datto in late 2014. Below, he gives an honest take about what he’d do differently and what he’d do again as a startup CEO. (Disclosure: NextView was not an investor in Backupify.)

In 2010, we were recruiting for a Senior Vice President of Sales and Marketing for Backupify, and it was clear that many of the people I was interviewing wanted the CEO role. I called the recruiter running the search and told him I was going to step down and hire a CEO. His response changed the way I thought about the CEO role for the next five years.

“Rob,” he said, “no offense, but you aren’t going to get a world class, been-there-done-that CEO into a company with less than $1 million in revenue. So, in order to hire a CEO, we have to give someone their first shot at the job.”

He continued: “In my experience of doing this many, many years, I’ve seen no correlation between what someone has done in the past, and their success as CEO. It’s such a hard job and so different at each company. You either figure it out or you don’t. And if we have to give someone their first shot, it might as well be you, because you co-founded the company and care more about it than anyone else ever will.”

He was right. The CEO job is simultaneously the best and worst job you can have. Over the past six years that I was CEO of Backupify, my mantra was a line from Walt Whitman’s “Song of Myself,” in which he says, “Do I contradict myself? / Very well then, I contradict myself. / (I am large. I contain multitudes.)”

Now that Backupify has had a nice exit and my life is in a different place, I agreed to write this post, full of my own advice based on my experience as a startup CEO. Some of it may involve contradictions, but you have to live those contradictions to do the job.

Advice to a First-Time CEO

1. Think more about business models.

I’ve seen many companies with great products die because a great product is not necessarily a great business. A great business model covers a lot of other flaws, but it isn’t “cool” to think about business models. But your job as CEO is really to guide your startup to a good business model. As you think about the channels you can use to sell, the supply chain that you build to create your product, and the customer segment you target, think about guiding your company to an equilibrium where the economics are in your favor.

Startups are incredibly hard. Weak economics just make them harder.

2. Focus your team and keep your team focused. But don’t stay narrowly focused yourself.

Teams need to focus and to have a clear goal, and so you have to communicate that, as well as keep them working on the right things. But as CEO, you should want optionality. Keep your head up. Keep looking around and engaging with new opportunities — but don’t let them distract your team.

Yes, it is time consuming. Yes, it is hard to manage. Yes, it feels like a waste of time that, for every 10 people you meet who want to work with you, nine aren’t worth the time. But the one that is might be the one that makes a difference. You have to find a way to keep engaged with opportunities around you.


3. Hang out with other founders and CEOs.

You can’t complain to your Board. You can’t complain to your team. Other CEOs are the only people you can sit down and talk with about the hardest parts of your job.

Other CEOs understand that sometimes you’re just faking it, that you have insecurities that may tear you apart, that your family and friends don’t get why you’re killing yourself for something that doesn’t seem to be working, and that you have to make decisions that are often just a choice between two bad options.

Build a good peer group to meet informally. It will help keep you sane.

4. Gets lots of advice, but ignore most of it.

Building a startup is hard, and there are 1,000 different paths to success. You will get lots of conflicting advice from lots of really smart, really successful people. Don’t think that because it’s all different that it’s worthless. Your job is to seek out diverse perspectives, assimilate the information, and make a decision. Keep at it.

5. Be pragmatic.

It’s nice to get great valuations and hire A-players. But sometimes you can’t. Sometimes the only path forward is to fill a gap with a down round of funding, a B-player, or some other non-ideal option.

There’s a Peruvian proverb that says, “Little by little, one walks far.” Sometimes all you can do is focus on that next little step forward.

Things I’d Do Differently the Next Time Around

A successful exit changes how I think about the world for sure. If I do another company someday, here are three things I will do differently that I wasn’t in a position to do the first time around:

1. The next time around, I’ll manage for capital efficiency.

Backupify was managed for momentum. I moved to Boston and knew no one and had no reputation, and so I had to constantly show product momentum, fundraising momentum, hiring momentum, revenue momentum — anything that was a signal that we were on a path to success.

My next startup will be managed for capital efficiency. I won’t have the same need to prove that I can do the job, so I can be more patient and trade time for capital. I will definitely do that.

2. The next time around, I will take more vacations.

Too many times at Backupify, I was worried that if I stepped away for more than a few days, the company would fall apart. Over the last year, we finally had a strong revenue base and a great team in place, and I was able to take three weeks of vacation.

If I do another startup, I won’t skimp on the vacations next time around. It is important to relax, and time off actually makes your work time more productive.

3. The next time around, I will spend less time at startup events.

These are important when you’re getting started. You have to get out and network, recruit, and evangelize. But it is terribly time consuming and often marginally productive.

The next time around, I think I will be in a position to skip most of it. Startup parties are great. Successful exits are better. I plan to focus less on the startup culture the next time around.

Special thanks to Rob May for sharing his advice to other startup CEOs and entrepreneurs. For similar stories, practical advice, and free resources created specifically for early-stage startups, subscribe to The View From Seed.