When serial entrepreneur Luke Cooper was heading up Fixt, an on-demand tech support startup, it had some common startup problems. The company had trouble raising money because it was growing really fast and its debt cycles and AR turns we're slow, so it lacked the features that VCs typically love in the later series rounds to raise the institutional money it needed.

Cooper says the company was just about at profitability and needed to get a partnership or capital provider in place that would allow Fixt to secure its future. So Cooper took a gamble.

“I flew out to Vegas to CES to just see what I can make happen,” Cooper says. “I knew that Assurant was going to be there. We had conversation with them in the past. They had made overtures to us in the past. Their biggest competitors were making overtures to us as well.”

Cooper figured if he was on the ground there, he could make something happen. He says he stayed at one of the cheapest hotels off the strip and snuck into the VIP reception that Assurant held.

“I made a beeline to the CEO, had a lot of conversation with him about our culture, the enterprise segment that we were growing over 400 percent year-over-year in,” he says.

Because of that move, he says within 60 days of that conversation, Fixt was under LOI, and was eventually acquired by Assurant in August.  

“But the best part is on the way back, a buddy of mine who was in the similar industry as mine asked me, ‘Hey, you want to ride back to the east coast?’ And I had no money so I said, ‘Sure,’ and he flew me back on his own on his private jet,” he says. “That's how you go out with style after getting your deal done.”

Cooper spoke at the recent Baltimore Smart Business Dealmakers Conference about Fixt’s sale to Assurant, strategies for fundraising as well as an initiative that’s underway to help connect African-American entrepreneurs with Fortune 500 companies. Hit play on the video above to catch the full conversation.