Brian Long

Starting Out at Penn and CNET

I have loved entrepreneurship and startups from a very early age, he told Bain Capital Ventures, explaining what draws him to founding: I like the idea of building something new with a group of people you like, and being in control of your own destiny. On the Marketing Playbook podcast he talked about side businesses at Penn, early roles at CNET and CBS Interactive, a job at the advertising company Pontiflex and why he left business school, according to the episode notes.

TapCommerce and Attentive

Fundraising was slow the first time. With my first company, I think I took 52 different fundraising meetings before we raised our first money, he told SC Media. That company was TapCommerce, which Bain Capital Ventures backed and Twitter bought in 2014. He and Jones then started Attentive, which he grew from his living room into a global business, according to Attentive.

Attentive pivoted early, after customers praised a first product that they then would not buy. The lesson he took was that people are too polite to give honest feedback, so he asks for a rating from one to 10 and treats anything under eight as neutral or negative. He collected the advice he kept giving younger founders into a book, Problem Hunting, which he wrote himself without a ghostwriter. I wanted to make something very practical, too, he said of it. Attentive grew to more than $500 million in annual revenue and 1,000 employees, according to Adaptive.

Turning to Security

Adaptive came from an incident close to home. One of our executives was the victim of a very large cybersecurity scam, and it was perpetrated through social engineering, he told SC Media. Research convinced him the problem was growing: The world needed something to help protect people from this next generation of AI-powered social-engineering threats.

He and Jones put in their own money at the start, and in April 2025 Adaptive raised a $43 million Series A co-led by Andreessen Horowitz and the OpenAI Startup Fund, OpenAI's first investment in a security company, TechCrunch reported. By December 2025 total funding was almost $150 million, and in September 2026 the company passed 2,000 customers, according to Adaptive.

He argues the threat is moving faster than most companies admit. We just need to make sure that our workforce across every type of vertical is ready for this threat, because they are not, he told IT Brew. His simplest advice for employees worried about voice cloning was Delete your voicemail.

Off the Clock

His favorite book for founders is Dale Carnegie's How to Win Friends and Influence People. The title is a little cynical, but the content is fantastic. When Attentive cut its list of company values from eight to four, the one he would have kept was lots of laughs. Life is short and you gotta have fun doing what you're doing. His advice to other founders is persistence: You've just got to stay at it.