Markup Hero

Jeff Solomon is a six-time founder who had just exited his company Velocifi for $128 million in 2017. After years of consulting and angel investing, he noticed a gap in the market: there was no single screenshot and annotation tool that did everything he needed. He'd used products like Evernote's Skitch integration and loved it, but no other tools offered that seamless embedded experience. Rather than chase another massive exit, Jeff decided he wanted to build something he'd actually use himself—and ideally turn it into a profitable lifestyle business.

Jeff launched Markup Hero during COVID in 2020 with a lean team of three co-founders he'd met at a consulting company. The product started as a direct-to-consumer offering: a $4/month screenshot and annotation tool with a freemium model that limited users to 10 screenshots per month before requiring an upgrade. The team built without raising any money, bootstrapping entirely from early revenue.

Beyond the core product, Jeff and his team envisioned a bigger opportunity: building an API and library that other SaaS companies could integrate. The vision was to recreate what Skitch did for Evernote—letting Notion, Asana, Monday.com and similar tools natively embed annotation capabilities. They began charging API customers on a per-markup basis, starting at a few hundred dollars per month depending on usage.

Jeff's primary go-to-market strategy from day one was SEO-driven content marketing. He started by identifying which audiences actually needed screenshots and annotations, then writing content to reach them—even if that meant writing about adjacent topics like product management, Notion templates, and other tools used by product managers and designers.

He produced content consistently, publishing new articles every single week. To scale this without a large team, Jeff developed a system: he'd receive 6-7 inbound inquiries per day from writers wanting to contribute guest posts. He'd reject most, but filter for high-quality contributors—especially agencies working on behalf of SaaS companies like Monday.com. He'd accept their guest posts in exchange for backlinks, then spend about 1.5 hours editing each draft (which he'd commission for ~$150). This allowed him to publish roughly 60% third-party content and 40% of his own writing.

Once the site's domain authority reached a certain threshold, inbound partnership requests accelerated, creating a virtuous flywheel. People asked to write for him; he'd assign topics and require them to provide two backlinks in return.

Beyond organic search, Jeff also ran a campaign on AppSumo, which brought in both lifetime customers and momentum early on.

About a year before the interview, Markup Hero had 3,000-4,000 paying customers. By the time of this conversation, they'd grown to approximately 10,000 paying customers generating roughly $20,000 in monthly revenue (closer to that figure after accounting for some variation from AppSumo lifetime deals). With operating costs of just $3,000/month (mostly hosting), the business was generating approximately $15,000+ in monthly profit that the three founders split as dividends.

Jeff's main bottleneck wasn't customers—it was product features. Users were requesting collaborative annotation capabilities (which he was building as "layers" similar to Photoshop or Figma, but asynchronous rather than real-time). Once that shipped, he expected it would drive premium upgrades significantly.

At 47 years old with two teenage twins and 8 hours of sleep per night, Jeff had deliberately chosen profitability and control over another venture-backed sprint. As he reflected: "raising 20 million bucks and going for the moon and taking 14 years to get to a 130 million dollar exit... versus making a nice business throwing off three million dollars in EBITDA with three guys—there's nothing wrong with that."

Markup Hero remained entirely bootstrapped with no outside investment, validating Jeff's thesis that you don't always need VC money to build a meaningful, profitable business.