Jesse Lipson is a self-taught software developer who became a full-time entrepreneur at age 23. In late 2005 he founded ShareFile, a file-transfer service for businesses that need secure, reliable and easy tools for sharing data. He launched ShareFile with $100 in Google AdWords spending and bootstrapped the company from zero to four million users in six years. ShareFile was acquired by Citrix for $93M in 2011, and today has over 50,000 paying customers and several hundred employees. He held a variety of roles at Citrix for the next five years, including serving on the company’s executive leadership team as Corporate VP of Cloud Services.
Jesse also co-founded Raleigh Founded in 2012, a coworking community with over 400 member companies and 100,000 square feet under management.
Most recently, Jesse started a software company called Real Magic in late 2017. In 2018, Real Magic launched Levitate, a software product that helps small relationship-based businesses keep in touch in an authentic and personal way with clients, prospects, and referral sources.
He holds a degree in philosophy from Duke University and serves on the Board of Directors of Yext (NYSE: YEXT), Green Places, and Brooks Bell Inc., the company founded by his wife, Brooks Bell (who was also a Download Q&A subject and a Pete Meets… guest).
1. What is in your pockets?
I always carry a tissue in my pocket, because I’m a habitual sneezer and I always have anxiety that if I sneeze, I won’t have a tissue. So every morning, I take a tissue and put it in my pocket.
Another thing I have in my pocket is a small case that holds four cards, because it’s so much easier. It’s actually been a game changer, because not having to sit on a wallet all day and being able to slide this tiny thing into my pocket has been really good. I keep a wallet and some cash in my backpack, but not carrying a wallet has been a nice productivity and comfort hack for me.
2. What exciting thing has happened recently for you or your organization?
Levitate is software that’s designed for what we call small relationship-based businesses, and what we mean by a relationship-based business is companies that really grow primarily through referral and word of mouth. More of a “soft sell” process of keeping in touch personally and authentically. We found that existing software out there like MailChimp is not personal. It’s not authentic. Most people ignore those types of newsletters, or if they read them, it’s not the same as if somebody reached out to you with a personal email or text or call. So what we’re trying to do is help relationship-based businesses scale that process of keeping in touch personally and authentically, using some technology and content and services.
As a company we recently crossed 3,500 paying clients, which has been very exciting. We launched a new industry vertical in nonprofits. So currently we focus on insurance, financial advisors, accounting firms, law firms, and now we’re starting to sell to nonprofits as well.
The other exciting thing is that we have a new product we’re launching, which I can’t talk too much about, but it will be launching in early September. We’ve been working on it for the past year or so and it’s built on the Levitate platform, but it’s addressing a very different use case, a very different audience. So I’ve been having a lot of fun working on the launch of this new product. [Note: Jesse talks a little more about the new product down below, including unveiling its name.]
3. What is your favorite coffee spot?
I am not a coffee drinker. I drink iced tea in the morning and so I don’t really go to coffee spots for the purpose of drinking coffee. My favorite breakfast spot that I like to go to is the Flying Biscuit. I have a standing breakfast every Wednesday morning with a couple people on my team at the Flying Biscuit. So if you come to the Flying Biscuit on Wednesday mornings, you’ll probably see me there.
4. What keeps you up at night?
There’s a lot to worry about right now. Over the last six to nine months I’ve been more closely following the macroeconomic picture, which is not something that typically a CEO of a small startup pays much attention to. But there are so many things to worry about and to stay up about.
One concern is what’s happening in the venture capital market. They are starting to freeze up due to the compression of valuations in the public markets for high-growth tech companies. I’m also concerned about inflation, the war in Ukraine, potential recession, that kind of thing.
5. What is your favorite restaurant or happy hour?
My common happy hour spot is Mordecai Brewery, because it’s right next to our office, so you will find me there. Oftentimes, we call it “Conference Room M” and sometimes we’ll do one-on-ones there. At one point, they named a beer, “Levitate Beer,” after us and I think it was probably the best-seller, so that’s my spot there.
6. What is next for you or your organization?
Levitate is really evolving from a product into a powerful software platform. We’re very excited to announce the launch of our new product, Coffee, built on top of the Levitate platform. We also just announced an additional $6M funding round to support our continued growth.
When I started this company, which was called Real Magic, the idea was that we were going to be a multi-product company. In October it’ll be five years, amazingly, since I launched the company and so that was about the time frame that I decided it would be good to launch a second product. What’s exciting for us is becoming a multi-product company.