A serial entrepreneur’s journey from marketing to cybersecurity: Founder Stories

In a recent episode of Founder Stories, Brian Long, CEO and Co-Founder of Adaptive Security, talked with host Matt Alderman about Long's entrepreneurial journey from digital marketing to cybersecurity.

Long and Alderman discussed why Long moved on from his successful marketing ventures, how he funded and built Adaptive Security, and the lessons he has learned along the way.

Long began in marketing and ran two successful companies that focused on solving data problems and helping organizations optimize their customer connections. But one day, as Long told Alderman, "One of our executives was the victim of a very large cybersecurity scam, and it was perpetrated through social engineering."

This opened Long's eyes to the current gaps in cybersecurity defenses and inspired him to launch Adaptive Security as an AI-focused cybersecurity awareness training and phishing-simulation platform.

"The more that we did research," he said, "the more I was convinced that the world was ready for something. The world needed something to help protect people from this next generation of AI-powered social-engineering threats.”

Funding Adaptive Security turned out to be smoother than it had been with Long's previous ventures.

"With my first company, I think I took 52 different fundraising meetings before we raised our first money," Long said. "We were fortunate [with Adaptive Security] that when we first started it, myself and my co-founder, Andrew [Jones], were able to put in some of our own money because we had had two prior successful companies.”

Adaptive Security, founded in 2023, had three investment rounds in 2025 alone, with $136 million raised from Bain Capital Ventures, Andreessen Horowitz and the OpenAI Startup Fund.

Startups should build name recognition and let investors come to them instead of aggressively chasing investors, Long added. As for early-stage sales and marketing, Long recommended prioritizing sales conversations and not relying solely on "friendly" customers.

"We hired three or four inside salespeople when we started the company," he told Alderman. "What I found is that you want to have a lot of sales conversations. ... I also really don't like the feedback and product-market-fit learnings that you get from friendlies."

He highlighted the importance of founders actively joining sales calls to directly gather feedback that might impact product development.

"It's not the same to listen to a call versus to be on the live call, ask the questions, dig in on things," Long said.

The cybersecurity field may seem crowded to many, but Long disagreed, pointing out that many firms provide consulting rather than platforms or products. He believes there's plenty of room for companies that focus on defeating social-engineering attacks.

"Anywhere from 95 to 99 percent of attacks still have some sort of social engineering, human component," he said. "The market is under-invested in this area, even with us doing it, and hopefully more companies like ours tackling this segment, because I do think it's where we're going to be most vulnerable in the next five to 10 years."

What kind of advice would Long give to aspiring founders?

"The folks I've seen who have just stayed at it, and maybe they've been through a couple different companies, maybe they've moved around a bunch of times, but they do ultimately reach success if they're just persistent and stay at it," Long said. "They really do. They do get there. ... You've just got to stay at it. Persistency."