It started with posting
Jack Boudreau, founder and CEO of Habits, built a viral marketplace the unglamorous way: by posting on social media. Educational and satirical content about personal finance, week after week, until it was pulling millions of views on a weekly basis and getting featured in Morningstar, Kitces.com, Newsweek, Business Insider, CNBC, and the WSJ. He bootstrapped the company for a couple of years, partnered with over 50 financial service firms, and eventually raised capital from notable angels and VC funds as the marketplace earned major press across the nation.
Somewhere in the middle of all that, the Engagement Engine was born. Not as a product. As a survival mechanism.
The internal tool nobody was supposed to see
Producing content across a blog, YouTube, TikTok, Instagram, Twitter, Threads, and LinkedIn at that volume is not a workload a person sustains on instinct. So Jack built an internal tool that used behavioral science and our marketplace data to figure out what his audiences were actually thinking - at the macro demographic level all the way down to the individual he was about to meet in person or on Zoom. Soon it was powering marketing campaigns, internal newsletters, and investor updates too.
By December of 2025, the realization landed: the marketplace was a valuable asset and a profitable product, but the real value was the GTM infrastructure built behind it.
The 30-stranger test
Before turning an internal tool into a product, we tested it the uncomfortable way. Jack opened his calendar to over 30 strangers who signed up for free 1:1 time over Zoom - people from all over the world - and ran each of them through the Engagement Engine before their session. Every time, the analysis was spot on: the blogs, editorials, articles, and websites in their orbit, and company or industry insight matched to their job title or employer. That's when it struck the Habits team that this could strike the balance of AI, data, and human authenticity.
Why authenticity is the whole point
Jack is a firm believer that in a world where one out of every two posts on LinkedIn is AI-generated, authenticity is the only differentiator left. That belief is built into the product. The Engagement Engine offers research and insight, but it forces you to lean on your own judgment and authenticity to decide what to do with it. It will tell you what your audience is thinking about. What you say next is still yours.
That's not a limitation. That's the design.
The engine was built to keep one founder sounding human at scale. Now it does the same for you.