KEY TAKEAWAYS
- ✓Start a newsletter as a marketing channel, not as the business itself. The business model will reveal itself once you have an engaged audience.
- ✓Failure and even bankruptcy aren't endings — they're expensive MBAs. Katelyn's VC-backed failure taught her everything about what not to do.
- ✓Test every product idea with waitlists and pre-orders before building. Let demand prove itself before you invest time creating.
Hello! Who are you and what are you working on?
Katelyn Bourgoin's path to building a million-dollar newsletter business runs straight through bankruptcy. Before Why We Buy existed, Katelyn was a four-time founder with a resume that looked impressive on paper but hid a devastating financial reality. Her previous venture had been a VC-backed startup that Forbes once described as potentially being the next major professional networking platform for women. Investors wrote checks. Press coverage flowed. Everyone told her the company was destined for greatness. Then it all fell apart.
The startup failed. Not in the quiet, pivot-and-rebrand way that Silicon Valley likes to romanticize, but in the brutal, life-destroying way that nobody talks about. Katelyn went personally bankrupt. She owed money she couldn't pay. The professional network she'd built during the startup years evaporated. Friends who'd been excited to be associated with a hot startup didn't return calls once it imploded. She was starting over from zero in her mid-thirties, in Canada, with no savings and a deep distrust of the venture-backed model that had nearly ruined her.
The rebuilding started with consulting. Katelyn had developed genuine expertise in understanding why customers buy, a skill born from years of desperately trying to figure out product-market fit during her startup years. She started offering customer research and buyer psychology consulting to other startups and small businesses. The work paid the bills, but consulting has a natural ceiling. You're selling hours, and there are only so many hours in a day.
To attract more consulting clients, Katelyn started a newsletter called Why We Buy. The concept was simple: every week, she'd break down a buyer psychology principle and explain how businesses could use it to sell more effectively. The tone was accessible and fun, not academic. Each issue used real-world examples, relatable scenarios, and practical takeaways that readers could immediately apply. She covered concepts like the IKEA effect, loss aversion, social proof, and anchoring, but always through the lens of practical marketing application rather than theoretical psychology.
The newsletter grew slowly at first. Katelyn promoted it through her Twitter account, where she'd been sharing buyer psychology insights and building a following. The format resonated because it sat in a sweet spot that almost nobody else occupied: too practical to be academic, too research-backed to be fluff. Marketers subscribed because they could use the insights in their actual campaigns. Founders subscribed because understanding buyer psychology was the difference between products that sold and products that sat on the shelf.
Then something happened that changed the trajectory of the business. A sponsor reached out offering $1,200 per month to advertise in the newsletter. This was right around the time Katelyn found out she was pregnant. The timing felt like a sign. Here was a revenue stream that didn't require her to trade hours for dollars, that could scale with subscriber count, and that would keep generating income even when she was on maternity leave. She took the deal and started thinking about the newsletter as a business rather than just a marketing channel.
The sponsorship revenue grew as the subscriber count climbed. Katelyn was deliberate about which sponsors she accepted, only working with companies whose products she'd actually recommend to her audience. This selectivity maintained trust with readers and, counterintuitively, made the sponsorship slots more valuable. Brands wanted to advertise in Why We Buy precisely because readers trusted Katelyn's recommendations.
By 2023, the newsletter had grown to well over 100,000 subscribers, and sponsorship revenue alone was hitting $25,000 per month. But Katelyn didn't stop there. She diversified revenue by creating digital products and educational offerings built around the same buyer psychology expertise. She launched courses, workshops, and training programs, always testing demand with waitlists and pre-orders before actually building anything. If a waitlist didn't fill up, she didn't build the product. This discipline, born from the painful lessons of her startup days, kept her from wasting time on things nobody wanted.
The financial results accelerated dramatically. In 2023, Why We Buy generated approximately $750,000 in total revenue across sponsorships, courses, and products. Then in the final 90 days of 2024, Katelyn generated $425,000 in revenue, nearly matching six months of earlier performance in a single quarter. The business was clearly on track for well over $1 million annually.
The subscriber base grew past 220,000, making Why We Buy one of the larger independent newsletters in the marketing and psychology space. Each new subscriber made the sponsorship slots more valuable, and the growing audience created a larger pool of potential customers for Katelyn's own products. The flywheel effect was powerful: good content attracted subscribers, subscribers attracted sponsors, sponsors funded more content creation, and the audience trusted Katelyn enough to buy her products.
Katelyn's approach to product validation is worth highlighting because it's rooted in the scars of her startup failure. She never builds anything without proof of demand first. Every new product starts as a concept that she floats to her audience. If people sign up for a waitlist or pre-order, she builds it. If they don't, she moves on. This approach means she rarely wastes time or money on products that won't sell. It's the exact opposite of how her VC-backed startup operated, where the team built features based on assumptions and hoped the market would catch up.
Her biggest mistake was spending too long in consulting mode before fully committing to the newsletter as a business. For the first year or two, Katelyn treated Why We Buy as a side channel to drive consulting leads. She underestimated the direct revenue potential of a large, engaged email list. If she'd focused on subscriber growth and sponsorship revenue from day one, the business could have reached its current scale a year or two faster.
What makes Katelyn's story particularly powerful is the contrast with her previous chapter. She went from raising venture capital, getting Forbes features, and building a team to going bankrupt and starting over with nothing. The business she built from the ashes is smaller in ambition than the startup that failed but dramatically more successful in practice. It supports a small team of three, generates over a million dollars a year in revenue, and gives Katelyn complete control over her time and decisions.
The lesson Katelyn emphasizes most is that the conventional startup playbook, raise money, hire fast, grow at all costs, is just one way to build a business. And for most founders, it's the wrong way. The newsletter model let her start with zero capital, test every idea before committing resources, and scale at a pace that matched her life rather than an investor's timeline. From bankruptcy to a million-dollar business, Katelyn built Why We Buy by doing the opposite of everything that failed the first time around.