He wanted to be a sports writer. Instead, Dave Gerhardt became the most trusted voice in B2B marketing - not by getting an MBA, not by joining a prestigious agency, but by saying plainly what everyone in the room was already thinking and refusing to dress it up in corporate language.
The path from PR intern to CMO to bootstrapped founder is not a straight line. It runs through Boston, through early-stage SaaS, through a company called Drift where he helped invent a category ("Conversational Marketing"), through a CMO seat at Privy right before its $100M acquisition, and back to Drift as Chief Brand Officer - before a Patreon experiment from October 2019 quietly became the whole thing.
That experiment was a paid newsletter and community called "The A List." Within days of launch, a couple hundred people were paying $10 a month. Within six months: 1,000 members, $10k/month. Gerhardt had stumbled onto something sharper than a personal brand - he'd found a gap. B2B marketers had no place to be honest with each other. No place to ask dumb questions. No place to say "our demand gen strategy isn't working and I don't know why."
People didn't just want to read my posts. They wanted to talk to each other.
- Dave Gerhardt, on the founding insight behind Exit Five
He renamed it Exit Five in April 2022 - a reference to leaving behind the old playbook of boring B2B marketing - migrated it off Patreon to the Circle platform, and lost $20-25k in monthly recurring revenue in the process. He rebuilt it within a year. He ran it entirely alone for over two years. In late 2023, he hired a COO named Dan Murphy. The team is now six people full-time.
What they've built is not a Slack group with a Stripe subscription. Exit Five runs 26+ virtual events a year, four in-person ones, an annual flagship called Drive in Burlington, Vermont that sold out 200 tickets in a single day. It has a job board, cohort-based courses, and an AI Playbooks series. It recently launched industry verticals - subgroups for FinTech, HealthTech, HR, Manufacturing - and 30+ geographic local chapters stretching from Boston to Sydney to Paris. The podcast has 348+ episodes. The newsletter has 50,000+ subscribers. Monthly active user rate sits at 40%, which puts it in the top 1% of all Circle communities globally.
The revenue model is equally straightforward: roughly 40% from $499/year memberships, 50%+ from sponsorships, the rest from courses and events. No outside funding. No complicated cap table. Annual revenue is tracking toward $3-5M.
The LinkedIn following - 191,000 and growing - is not accidental. It's the primary growth engine, generating 60% of all new signups. Gerhardt posts with the same frequency and directness he built his career on. He talks about what's working, what broke, what he believes and why. He will tell you that most B2B marketing is lazy, that founders should be the loudest voice in the room, and that winning on philosophy beats winning on features every time. He wrote a book about it in 2022 called Founder Brand - his second, after co-writing Conversational Marketing with Drift CEO David Cancel for Wiley in 2019.
The stranger detail: none of this came from a plan. Exit Five grew out of one person's honest opinion that B2B marketers deserved better. That opinion, posted consistently on LinkedIn, compounded over years into something with a team, a P&L, and a Drive event in Vermont. Seth Godin talks about making something for someone. Dave Gerhardt looked at B2B marketing and decided to be that someone.