No Trick: ShareFile Founder Lipson Back With Real Magic

Jesse Lipson has long been fairly top-of-mind for the Triangle tech community. The ShareFile founder sold his company to Citrix in 2011 for $50M+ but stayed another five-plus years with the firm as it expanded its Raleigh office to more than 900 people. Along the way he co-founded the entrepreneurial community and co-working space HQ Raleigh with a group including his wife, fellow business-owner Brooks Bell.

But not everyone is fortunate enough to stay in the forefront of people’s thoughts. That’s where Lipson hopes that Levitate might float in.

Levitate is the first and (so far) only product of Lipson’s new startup, Real Magic. It’s a “keep-in-touch” application for small service businesses that rely largely on word-of-mouth and relationships to generate business rather than advertising or a hard sell—insurance agents, law firms, investment advisors, commercial real estate agents, and the like.

“Most people are just doing this manually now,” Lipson says. “Maybe they see someone at an event or someone’s name comes up in conversation, so they reach out. Well, people can do long division on a piece of paper, but they use calculators and computers because they do it better.”

Both web-based and mobile, the Levitate app is built with Outlook and Gmail plugins because, as Lipson says, his clients “live in their email and calendars.” Users can be sent reminders to check in with contacts at set periods, easily enter notes about a meeting once it’s over so they can recall where that would-be client grew up or her son’s name, or even tell them which of their contacts likes golf so they can share the latest Tiger Woods news.

Levitate launched as ready-to-sell in mid-April, about five months after Lipson began working on the company fulltime. Real Magic now has roughly 30 customers generating $5K in monthly recurring revenue and is growing fast. By the end of next year, Lipson is aiming to have several hundred customers, which would mean annual recurring revenue would likely be crossing a half-million. That would also mean expanding from the current eight employees to about 50.

The Duke grad has been down this road before, of course, but some things have changed since he started ShareFile—which enabled companies to share large and/or private files—in late 2005. Back then a relatively cheap Google AdWords account could quickly start generating leads, Lipson says, and since SaaS was newer, there weren’t as many web-based apps to compete with.

Fast forward to 2018: “No. 1, acquiring customers isn’t as easy or cheap as setting up AdWords. No. 2, because there are so many SaaS apps, businesses suffer from overload. They say, ‘I already have 10 software apps, why do I need an 11^th?’ They don’t want to enter data. That’s why we thought it was key to integrate into a service they’re already using [like Outlook or Gmail] rather than try to get them to use something entirely new.”

The fact that Lipson isn’t entirely new to the startup space has benefits of its own. Several of Real Magic’s employees worked with him for years at Citrix, and Lipson’s past success has enabled him to self-fund the company’s start to move a little faster than he did initially at ShareFile, which was entirely bootstrapped and grew almost exclusively on its own revenue.

Now that Levitate has paying customers, though, Lipson is focused on both growth and unit economics—the cost to acquire a new customer compared to the recurring revenue generated by that customer. Right now he’s looking to hire for a few sales roles to add fuel to the growth fire.

And while he’s focused on keeping costs down as well, Lipson hasn’t been able to work a sweetheart rent deal for the company’s HQ Capitol Club offices. If only he was more top-of-mind with HQ’s owners.