RALEIGH – Even in the midst of a pandemic, serial entrepreneur Jesse Lipson is making big deals.

The 42-year-old, four-time founder is fresh off another $6 million raise for his latest venture, Real Magic, bringing total raised to $12 million to date. Meanwhile, the startup’s first product called Levitate, a “keep-in-touch” marketing platform that helps businesses grow, is taking off after notching 1,000 paying customers.

“We’re growing really fast and adding hundreds of customers a month, so there’s a lot to do,” the former ShareFile founder said this week.

Lipson is one of the Triangle’s big success stories and homegrown talents.

After graduating from Duke University in 2000, the self-taught engineer became a full-time entrepreneur at 23. Later, he launched Sharefile, a file transfer service that he grew to four million users in six years and sold to Citrix in 2011. Two years ago, it ranked #80 on Forbes’ Just Companies list, with a market cap of $13 billion.

In 2018, he launched Levitate.

WRAL TechWire’s Chantal Allam had the chance to chat with him over Zoom this week. Here’s what he had to say: This interview has been edited and condensed for style purposes.

  • Congratulations of the recent raise. Tell us more about it.

We’ve raised some additional VC funding abd just closed on another $6 million VC round. We also hit a pretty big milestone — 1,000 paying customers. So we’re really excited about, and  we’ve hit some scale overall as a business. We’re now up to 80 employees as well. A year ago at this time we were about 325 customers. So we’ve roughly tripled our customer base and

So, yes, we’re going to be celebrating both of those things on Friday. We’re calling it 1K Day to celebrate 1,000 customers. It’ll be the first time we’ve all been back together, although we’re doing in groups of 10, and we’re doing it outside HQ Raleigh in the Gateway space, outside one of the breweries it’s part of the shopping center there.

  • Why now?

We’re growing really quickly, so we can put it to use — to keep building the awareness about the product and keep investing in hiring and things like that. I think that with a lot of the uncertainty out there with coronavirus, it’s good to make sure that you’ve got runway and security.

  • How has your business been affected?

Actually, we’ve been pretty lucky. Being a software business and just kind of the nature of our product, we’ve done really well. We’re really still excited about what we’re doing, and our investors were more than willing to fund us. Even though we had planned on raising money a little bit later in the year, we figured it would be a good idea to go ahead and and do this route.

  • So what are you going to use the funds for?

We’re hiring primarily across the board — sales, customer support, success and engineering; really just kind of scaling the entire operation. We’re growing really fast, so we’re adding at this point hundreds of customers a month. There’s a lot to do and it just means a lot more people. We brought on like, five to seven new people, just in July alone. We’re hoping that this time next year that we’re going to be multiple times the size that we are right now.

  • What do you think is fueling this growth?

It’s a couple things. We’re starting to build some awareness. We’ve hired more people to spread the word about Levitate; that’s a part of it. We’ve also continued to evolve our product and make it better; and we’ve done some key integrations and partnerships over the last year. With the coronavirus situation, our product is really about helping people keep in touch and stay top of mind and authentic way, usually through email. These days, people have realized how important it is to stay in touch.

When we got into March and April, we saw the highest active use that we’ve ever seen in our product because a lot of people are just trying to communicate with their customers about what’s going on. When we saw the spike  in our own customer base, I realized that I needed to do something.

  • You’re based in HQ Raleigh. Are you back in the office?

Most are not. I would say out of our 80 employees on any given day, we may have like, say 10, people in the office. So we’re mostly still working from home. and we’ve been able to be pretty effective, working remotely. We’ve just basically made the office available to people who want to come in under certain restrictions. I would expect that we’re even as COVID kind of fades away eventually, that we’ll probably stick with this kind of hybrid situation because people seem to like it. It’s been working well.

The one thing we’re trying to figure out is how to bring that kind of social element back to work when people are separated. We’re still working on that. This Friday will be interesting because it’s our first attempt to do something where people cycle through and and actually get to see each other. We’ve basically got tables outside; we set up a Google Sheet, and had up to 10 people sign up per hour. People are cycling in to get their special t-shirts and cupcakes, and they can have a drink. We got Levitate masks printed.

  • If it’s this complicated organizing a meetup with your employees during this climate, what about creating a company culture when you’re scaling and not meeting in person?

It’s a big challenge.  I mean, it’s probably like 20-plus percent of our employees have started since COVID. So I’ve never met them in person. And, you know, I think that’s gonna be one of the biggest challenges for companies. When we go back to a hybrid environment, I can actually imagine not needing to be in the office as much for the work part, but maybe more for the social part. Where you’re working from home, but then you go do a happy hour with people in your company. That’s really where you get to kind of know people and develop the social bonds that help make it easier to collaborate on the work.

  • You’re an HQ Raleigh founder. With this new injection of funds, do you have you have plans to increase the size of your office space at HQ Raleigh?

We’re pretty happy where we are, and I think because now not everybody is going to the office, it gives us more time in our existing footprint . Prior to COVID, we probably thought that we were going to need to find a new space by the end of the year. But this environment actually expands our runway. I feel like the office environment is changing right before our eyes, and if we had to build out a new space now, I feel like we’d probably get it wrong.

Post-COVID, offices may be more meeting tables and and maybe less about just desks. Maybe it will look like an airport lounge or something like that. Luckily, we probably have a little bit more time to watch it play out. Eventually, when we do our own office, hopefully we can kind of design it for the work of the future.

  • So one last quick question: How does Levitate compare to ShareFile?

I always kind of track where ShareFile was at this time, and we’re definitely kind of growing faster than ShareFile was at this time. Part of that is due to the funding. With ShareFile, we didn’t raise any funding; we were totally bootstrapped. But I absolutely think that this company will be bigger than ShareFile and that’s my goal. I think it has the potential.

  • Do you have an exit strategy already in mind?

Not really. Having already sold a company with ShareFile to Citrix, I’m not really itching to to sell the company. I’m enjoying running it. It’s pretty unlikely that we’ll sell the company at the same size that ShareFile was, about 100 employees and $10 to $15 million revenue range. I want to grow the company bigger than that. Eventually, in the in the very long term, every company usually either sells or goes public. For us, that’s a way in the future, probably the five to 10 years from now we’ll start to look at that.

Raleigh’s Jesse Lipson secures $6M for Levitate app, lands 1,000 paying customers