Jesse Lipson: Why he’s going back to work – and targeting smaller businesses

In the second part of an exclusive interview, Sharefile founder Jesse Lipson talks about his decision to launch a new company just a few months after leaving a senior position with Citrix, which had acquired ShareFile in 2011. He also talks about lessons learned from building ShareFile and why his new business is targeting small- and mid-sized businesses.

[Founding Real Magic: Read the first part of the interview online.]

Why did you decide to begin a new venture so soon after leaving Citrix ShareFile?

To me it has felt like a long time. [Smile] After leaving Citrix, I took six months off to travel the world, including a 40-day road trip through the United States.

It was a great experience, but now I’m ready to settle back into Raleigh and begin the next phase of my life.

What was the best time about your time off?

The best thing was getting to spend a lot of quality time with my wife Brooks, but the second best thing was not having to check my email.

As an entrepreneur and corporate executive, even on vacation I tend to be thinking about the hot issues happening with the business. During my break, there was no business so I could truly relax and focus on the present moment.

I’m trying to take some of that mindset back with me now that I’m back to work.

What were the key lessons you learned from building and selling ShareFile that are helping you build and launch a new company?

I learned so many lessons but I’ll share just a few.

The most important lesson is to run the company based on a clear set of core values. Core values help keep the company aligned and provide a great compass for any employee to help make decisions in their day-to-day work.

Another lesson is to always try to make data-driven decisions. Using data helps keep politics out of the process and ultimately results in better decisions.

The final lesson I’ll share is the importance of focusing on great customer service. Amazing customer service can compensate for a lot of other shortcomings when you’re building a business.

Why do you see the mission of your new venture, Real Magic, as such a big opportunity?

I’ve spent the past 12 years learning about small and medium-sized businesses as I ran ShareFile and other products like RightSignature, Podio, and GoToMyPC for Citrix.

I believe that small businesses are an under-served market in the software industry right now. Almost every venture funded tech startup focuses on the Enterprise market, but SMBs still represent about half of software spending in most markets.

I also see small businesses as the engine for job growth in the economy, and I’m passionate about building software to help them.