Hamilton is the owner and “dividend chief” of Dividend Watch, a software-as-a-service (SaaS) solution designed to give individual investors better tools for dividend investing. The strategy advocates buying stock in companies that regularly pay a portion of earnings to shareholders as dividends, generating a consistent income stream that can help replace retirees’ former paychecks. The site, which has an email list of nearly 40,000 subscribers, tracks over 83,000 stocks and exchange-traded funds (ETFs), as well as almost 27,000 portfolios.

A roundabout route to entrepreneurship proved a prime training ground for his current role. With an MBA in finance and stints as a stock picker at mutual funds and endowments under his belt, Hamilton changed gears to apply his investing acumen at The Motley Fool. He ultimately quarterbacked the site’s personal finance content strategy during his nearly decade-long tenure, which helped chart the course for his next move.

“We covered dividend investing, and I created some successful marketing campaigns around it,” he recalls. “We had distribution, traffic, and interest, but there was no all-in-one product out there to satisfy that demand.”

With the seed of an idea sprouting, he struck out on his own in 2022. Initially keen to build a portfolio of websites, he bought and sold a couple before purchasing Dividend Watch last January. His vision is to transform it, without VC backing, into a one-stop resource for dividend growth investors and retirees—a group often overlooked by legacy money management firms.

“My goal was to find a gap where big brands don’t compete because it doesn’t move the needle for them,” Hamilton says. “For a small business, that audience can be very meaningful.” 

His Motley Fool experience taught him that while DIY investing content strategy tends to spotlight newsy, high-growth topics—“Elon Musk, Nvidia, all that hyped sort of stuff”—there’s still ample opportunity to cultivate another kind of customer.

“High-growth stocks are a valid investing approach, but there are plenty of other strategies for retired people, or those close to retirement and more risk-averse,” he says. “Those markets are pretty massive–they just need to be marketed to differently.”

Retirees as a market opportunity

Retirees also appreciate sound money advice. One in three worries about outliving their investments, while two in three don’t use a financial advisor.

Hamilton began revamping the site, using proprietary technology to build out its tracking resources and analytics. He also introduced new features, such as a calendar view of dividend payouts that users can map to expenses and investment plans. Other “dividend investor-first insights” include a tool that illustrates how reinvesting a stock’s dividends impacts various performance metrics over time. In addition to a host of free content, Dividend Watch offers two subscription tiers for $72 and $99 annually, which unlock a range of advanced analytics, tools, and research.  

Next on the agenda was marketing—a key focus for a startup.

“The former owners built a great product, but they didn’t grasp the marketing side, which is really most important,” Hamilton says. “I saw the opportunity, which fit perfectly with my background and passion for investing. A lot of stars aligned in a surprising way.”

To expand its audience—primarily retirees, who represent roughly half the site’s users—Hamilton and his team are investing heavily in content distribution through organic content SEO and, crucially, community forums.

“That’s where our audiences are super engaged, and where we build them,” he says.

By posting helpful informational posts and responding to queries on Quora, Reddit, and smaller niche dividend forums, Dividend Watch is growing both its brand awareness and subscriber base. The next step is to develop content for YouTube, a leading online destination for DIY investors.

“We’re skipping social, email newsletters, and paid marketing, and we’re not posting much on LinkedIn or other portals,” he explains. “Our strategy is to stay laser-focused on being great at one to two distribution strategies, which is critical to avoid spreading ourselves too thin.”

Advice for entrepreneurs

He’s also jumping in personally on the customer service front.

“It’s the most valuable feedback loop we have,” says Hamilton. “If we’re not doing something well, we can fix it for that customer and the thousands of others who use the product and will in the future. Many have said they were pleasantly surprised to receive a reply from the owner, which helps improve churn rates and engagement over time.”

While the site remains a work in progress, his efforts are paying off. With revenue growing 3% to 5% month over month, “all our metrics are now going in the right direction,” Hamilton says.

His advice for other entrepreneurs? Stick to what you love.

“I explored a number of different products when I went out on my own, but returned to investing because it’s my biggest passion,” he says. “Focus on something you truly enjoy—that’s the only way to stay the course and persevere, because there will be lots of roadblocks and challenges along the way. Most businesses fail without that passion.”