Bootstrapping·Dean Mathews, OnTheClock

OnTheClock: Bootstrapping a $5M+ SaaS Without Talking to Customers

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Dean Mathews is the founder and CEO of OnTheClock, a time-tracking software that helps small businesses manage their employees' hours.

In 2004, Dean was sitting at his kitchen table with his laptop one day, browsing through small business and accounting forums.

As he scrolled, he noticed a trend: people were constantly complaining about not being able to find reliable, easy-to-use time-tracking systems for their companies.

Dean, who was working as a software consultant at the time, had a lightbulb moment. He thought to himself, "You know, I can build that for them."

Dean spent the next few months building the first version of OnTheClock. He launched it in June 2004, while still maintaining his consulting work.

For the next decade, OnTheClock remained Dean's passion project. He'd dedicate about 20 hours a week to it, squeezing in time between client projects to improve the product and learn about marketing.

Despite the limited attention, the business grew steadily through SEO and word-of-mouth referrals. By 2015, OnTheClock had hit a major milestone – $1 million in annual recurring revenue (ARR).

The following year, Dean took the plunge. He handed off his consulting clients and brought his brother on board to develop a mobile app for OnTheClock.

Focusing full-time on the business accelerated growth, but it also brought new challenges. Dean had to shift from being a hands-on developer to leading a team – something he was initially reluctant to do.

Along the way, Dean faced other hurdles. Paid advertising didn't work well for them, and he had to learn how to be an effective leader. But he persevered.

Today, OnTheClock serves about 18,000 customers. The company generates well beyond $5M in annual recurring revenue and has a team of 22 people. And Dean's business is fully bootstrapped he's never raised any external funding.

This episode is part of our Bootstrapping series.

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