Editor’s note: Startup Spotlight is a regular feature as part of WRAL TechWire’s Startup Monday package which includes updates to our exclusive Startup Guide, calendars of events, an exclusive list of Triangle Meetups, and a recap of the previous week’s headlines from the state’s entrepreneurial companies.


DURHAM – To bootstrap or not to bootstrap? Sometimes, the decision is already made for you.

“Things were super crazy in the spring of 2000. It’s not like people were hanging around, offering up venture capital,” Joe Colopy, serial entrepreneur and co-partner of Jurassic Capital, recalled while appearing as a panelist as part of Techstar’s inaugural Raleigh-Durham Startup Week last week. “It was very, very different back then.”

He’s speaking, of course, about the early days of his marketing software firm, Bronto. In 2015, he and co-founder, Chaz Felix, became one of the Triangle’s most successful exit stories, bootstrapping the company for 14 years before selling to Netsuite for $200 million.

But at the beginning, in the wake of the 2000 stock market crash and the dot-com bubble, Colopy said it wasn’t so much a choice.

“That’s just kind of the circumstances I found myself in,” he said.  “I was more like, I could kind of muster through this.”

Jurassic Capital, led by team with ties to Bronto Software, closes $20M to invest in growth-stage companies

Bootstrapping, and more

The session that tackled the topic of bootstrapping a company was one of roughly two dozen free seminars held as part of the four-day event.

During the discussion, Colopy shared the stage with Jesse Lipson, the founder and CEO of Levitate, who also bootstrapped his second startup, Sharefile, that sold to Citrix in 2011.

Levitate's CEO and co-founder Jesse Lipson and Jurassic Capital's Joe Colopy appeared as panelists at Raleigh-Durham Startup Week on Thursday.

Jesse Lipson, left, and Joe Colopy, right, speak about the highs and lows of bootstrapping a startup company during a Raleigh-Durham Startup Week session on Thursday, April 21, 2022.

Together, they shared the highs and lows with the audience of a few dozen people, and both said the decision often boils down to circumstances.

“We’ve realized you have to play different games at different times,” said Colopy.

Statistics are sketchy, but experts generally agree that about six million new businesses start up in the U.S. in an average year.  Of those, only about 70,000 startups get angel investment, and fewer than 5,000 land any amount of venture capital.

In Bronto’s case, they had youth and scrappiness, said Colopy, and the stealth resolve to just figure it out. Eventually, venture capitalists did start calling, but by that point it didn’t make sense. “We were already growing great without it,” he said.

Fast-forward to today: Colopy heads the Durham-based equity firm Jurassic Capital, which recently closed on $20 million to invest in growth-stage companies.  It focuses on companies that are generating between $1 and $5 million in annual revenue, he said.

In these cases, he said it’s about leveraging his network and resources to help these companies take it to the next level.  “More often than not, they run into their limitations because of leadership or ambition. It’s just messy in some way. We get involved, and kind of keep that party going.”

Bottom line: “Venture capital is not free,” he said. “It can certainly make sense, but there’s certainly a very real trade off. Money is helpful, but it’s only helpful if you spend it very effectively. And it’s hard to do that at first.”

Why startups should care about branding: Entrepreneurs Joe Colopy, Keith Pigues explain

Bootstrapping versus VC

Lipson, meanwhile, has experienced both sides.

After graduating from Duke University in 2000, the self-taught engineer became a full-time entrepreneur at 23. He launched Sharefile, a file transfer service that he grew to four million users in six years before exiting to Citrix.

Along the way, he also declined to take outside capital. Another dot-com-bust child, he said he’d witnessed a lot of venture capital used “in a really bad ways.” “It left a really bad taste in my mouth about venture capital.”

He also wanted the option to code, experiment and change his mind. But it also took its toll. “I got to 1000 customers before I hired a single employee. I couldn’t because I just didn’t have the cash. That’s a pretty difficult way to live. It made me go slower; and it is really, really hard to do.”

Then in 2018, he launched Real Magic. This time around, it’s a completely different calculus. He’s older with a proven track record.

Its first product is Levitate, a “keep-in-touch” marketing platform, and has helped the company raise $20 million to date including $8 million in 2021. Backers included Tippet Venture Partners, Peter Gassner, and Bull City Venture Partners.

Lipson said his decision to raise funds came down largely to energy levels. “I was 39 [at the time]. I really just did not think I had it in me to do it again.” He also didn’t have to waste time pitching. “I didn’t even build a pitch deck. The capital was there if I wanted, and also it was friendly capital. People that I have relationships with, who would basically let me run the company with a lot of autonomy.”

Ultimately, he concludes: “Bootstrapping is awesome, but you have to be prepared to be unbelievably scrappy and work incredibly hard to overcome the lack of capital.”

Q&A: Raleigh’s Jesse Lipson dishes on the meteoric rise of his Levitate app