How to be an Effective Leader: Q&A with Rob May, CEO & Co-founder of Backupify

Rob May, CEO & Co-founder of Backupify

Rob May, CEO and cofounder of Backupify, knows a thing or two about leading the pack. Recently named one of our city’s top leaders in Boston’s Business Journal’s 40 Under 40, he takes a grounded, heartfelt approach to entrepreneurship. His passion for writing, growth, and learning inspire him to speak frequently at technology conventions across the country, as well as regularly contributing to publications such as VentureBeat and Wired. Since co-founding Backupify in 2008, Mr. May has led the company to establish itself as the leader in backup and recovery solutions for SaaS applications.

From digital design engineering and working in business development, to serving as an adjunct faculty member at the University of Louisville School of Business, Mr. May’s collections of experiences make him the prime example of a well-rounded leader. Between a busy day at the office and a board dinner on a Thursday evening back in July, Rob sat with us to chat leadership, work-life balance, and what it means to give back.


The Q&A

TUGG: Let’s jump right in. The titles of CEO and Co-founder come with a lot of responsibility. How do you balance it all?

MAY: For me, one of the major challenges of being an entrepreneur, CEO, or any high level executive at a tech company, is avoiding becoming one-dimensional. Being a leader takes a lot of time and a lot of focus, and actively finding balance can be difficult. Making money is a nice thing; it enables us to do a lot in life. But money can’t be the only focus.

Take for example, vacations. Everybody likes to go on vacations to refresh and reset, but there’s never a convenient time to take time off when you’re an entrepreneur. But you know that if you don’t take that time off, you’ll be less effective overall--without a break you’re likely to burn out. So the question is, when do you do it? When do you force it? When everyone at Backupify gets involved with volunteer opportunities and events that support nonprofits, we get the chance to step back and gain some valuable perspective.

The work environment of a startup is more stressful, more demanding, than a traditional job. Most early stage companies in particular--until they build up $10M - $15M in revenue-- are filled with people who just work a ton. And they like working around the clock. And even though all that hard work can be good for their careers in some ways, it’s bad if they don’t do anything else. It’s not good for the company, it’s really not good for anybody. So, I think of TUGG as a tech balancing force. The organization’s events helps entrepreneurs stay grounded, stay real, and help people remember what’s really important.


TUGG: We’ve heard a lot of tech entrepreneurs in Boston recently comment that they’ve grown tired of the spending their precious downtown doing the same old thing, like drinking at the pubs after work. Do you think the young & upcoming CEOs are growing out of those social habits they picked up in college?

MAY: The tech scene has undergone a shift over the last couple years. If you look back at the 90’s and early 2000’s, there were a lot of entrepreneurs in the city who were older; they were people who came out of companies with an idea, and established their own companies using their existing networks. I think people are little bit misled [regarding age in the tech sector]. The average age of a founding CEO is 38 years old, according to the Kauffman Foundation.

A little more about the report:

Infographic by Mitchell Hartman at

Infographic by Mitchell Hartman at

Dane Stangler is the vice president of research and policy for the Kauffman Foundation. ‘“The Millennials would certainly appear to be more predisposed to entrepreneurship than prior generations,” says Stangler. And yet: “The 20-to-34-year-old age cohort still has a far lower percentage rate of entrepreneurship than older cohorts, and that rate has actually fallen in the last couple of years.”’

‘Stangler offers at least one possible explanation: “No matter how badly you want to be an entrepreneur, no matter how low the cost of starting certain kinds of companies, if you come out of school with $60,000 in debt, entrepreneurship may not be as attractive an option.”’ (


MAY: There’s been this dramatic trend in entrepreneurship shifting to those who are dramatically younger and that comes with the risk of becoming a frat house atmosphere.

It might seem fun at first, but that kind of environment really isn’t healthy for anyone. (For example: the SnapChat CEO email scandal.) As a leader, you are always on, and have to be much more careful about what you say and do. You have to be careful not to set bad standards and low expectations for the people who work for you.


TUGG: Shifting gears a little, can you tell us why you chose Boston as the location to grow your business and develop as a leader?

MAY: San Francisco and New York were both possible places to move the company, but we decided on Boston because of its fantastic culture. I like Boston more, in comparison to the other cities, because it feels more balanced here. Silicon Valley is all about tech. New York is all about the money on Wall Street. Boston has a more balanced economy, we have a strong educational component, we have a strong biotech component, in addition to a thriving technology industry. Plus, we have bigger companies, like Gillette, that employ a lot of people here. So I think as a result, Boston provides us with a more balanced and intellectual perspective on the world.

In terms of leadership, I’d like to recommend a book written by Jeffrey Pfeffer called Power: Why Some People Have It and Others Don't. Pfeffer talks about the neurochemical changes that start to happen when you achieve a position of power. You start to be more aggressive, you start to take more risks, you start thinking you’re untouchable, you start develop a lot of hubris, and all that becomes dangerous -- ultimately leading to your downfall.


TUGG: So how do you stay so grounded? What advice would you give to help other leaders manage all that power?

MAY: When I did my MBA program at the University of Kentucky, I did a research project on a guy named Robert Greenleaf, who wrote a series of books called Servant Leadership. Greenleaf emphasizes that a leader’s job is to serve other people and empower them to do better work. And, I think, particularly in tech companies where things change rapidly, a leader can’t know everything. You have to function like a coach. You have to view your employees as people who are playing the game in real time, and you need to let them make decisions while you give constant feedback.

You have to make the extra effort to make sure your employees remain balanced and grounded. Nothing kills a company faster than the hubris of thinking that you’ve got it all figured out, you’re better than everybody, and you’re untouchable. A lot of companies fly pretty high, but they crash hard. So be careful.

Here’s my theory: tech companies change rapidly because the tech ecosystem changes rapidly. New competitors come and go, new technologies come and go, but the best strategy for dealing with rapid change is to have a diversity of ideas you can pull from. If you’re single minded and ideological, you are not going to be successful. You need to be flexible, pragmatic, and creative. The best way to do that is to be balanced, and to maintain balance, you need to do different types of things. One of the way to do that is to encourage people to get engaged and involved in the tech community. You can also encourage employees to continue their education, which a lot of startups don’t do. I think startups should do these programs very early- comp people on their continuing education. You can encourage people to get involved with nonprofits, and philanthropy and social organizations.

One of the things that leaders have to remember is that you walk around with a megaphone. Every little thing you say, people will judge. They’ll try to interpret it, read between the lines like “He’s a CEO! What did he mean by that?” You have to be careful of what you say. It’s important that you put your stamp of approval on things like taking lots of vacation, getting lots of rest, taking days to volunteer with TUGG, joining philanthropic organizations outside of work. We encourage folks at Backupify, for example, to give back to the community. Lots of people have helped me get to where I am today, so I like to give back any way I can, and my employees should take the same approach. And giving back takes on a different definition for everyone. Whether you contribute knowledge, mentoring, money, time, or you just lend your stamp of approval to something because you’re a tastemaker, it’s all relevant and important.


TUGG: Can you describe what you think it means to be a good leader? How do you know when you’ve officially become successful?

MAY: As a leader, you need to judge yourself based on the long term success of those you lead. I judge myself this way: I ask myself, “when you look around in ten years, have the people who’ve come through Backupify (whether they were there for two years or eight, no matter how long) gone on to make an impact on the world? Or did they lead meaningless, mediocre lives?” I like quirky people. I like people who’ve studied weird things and have unusual hobbies, because it shows a curious mind. It shows clearly when people are motivated and interesting. It’s very easy, in life, to just get sucked in. Some Americans spend an average of 22 hours a week watching TV, and then they look around and say, “Wow. I’ve spent the last decade doing nothing.” That’s the worst place anyone can end up.

Making an impact on the world can take on many forms. One person might’ve gone on to start his or her own company, another person may have started a nonprofit, or joined another project. It’s my job to push people out of their comfort zones. I actually tell people who work for me, “Hey, my job is to make mildly unreasonable demands, otherwise, you’re not going to be challenged.” If we set easy targets, then life is boring. Leaders need to set high standards across the board. I expect a lot of the people who work for me; I expect them to be professional, to communicate well, to write blog posts, to stay up on industry trends, to participate in conversation. I don’t want them to be mindless drones.

People seem to always be looking for easy answers to things--you know, “Three key steps to be the best leader,” and so on. I don’t think that’s the way to approach things. It sounds cheesy, but at your core, you need to be true to yourself and the things you believe in. There are a lot of ways to define success, and you shouldn’t get honed in and assume you need to be exactly like someone else to be successful. You can achieve success in your own way. You need to find your own ways of doing things. Take the best practices and the lessons you’ve learned from working other places, assimilate them into your leadership style, and go from there.


Krysta Voskowsky (@KVoskowsky) is TUGG’s Community Manager & Events Coordinator. Krysta holds a BS from Champlain College and an MFA in Creative Writing from Emerson College.


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