Analyzing markets for months before finding the right idea and building a 5-figure MRR product

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Most founders pick a market by falling into it. Derrick Reimer picked his on purpose, and the choosing took months.

Derrick is a software developer turned founder with a track record that includes real wins and one honest failure. He started Drip, an email marketing platform, and sold it to Leadpages in 2016. After that he took a big swing at Level, a thoughtful alternative to Slack, which did not pan out. He followed that with StaticKit, a forms-as-a-service tool that found modest traction before he sold it.

In 2020 he started SavvyCal, a scheduling tool built around a simple social observation: sending someone your booking link has always felt a little one sided. It has been his main focus for six years, bootstrapped with backing from TinySeed, and now serves thousands of customers.

SavvyCal is now two products. SavvyCal Meetings is the original scheduling link product, alive, well, and still generating the vast majority of revenue. SavvyCal Appointments, built over the past year, is an API first, HIPAA compliant scheduling infrastructure product aimed at healthcare and SaaS companies that need embedded scheduling but do not want to build or maintain it themselves. Together the two products bring in a five figure MRR, and the team is deliberately small: Derrick full time, a full stack developer, and a support specialist.

Here is how he chose the market, why he built a second product instead of chasing feature parity, and what he has learned about picking a niche like it is a cofounder.

SavvyCal came from a deliberate search for the right sized problem. After Level did not work out, Derrick spent a few months auditing SaaS markets, looking for proven demand, recurring revenue, and room for a differentiated angle, rather than trying to will a brand new category into existence.

Scheduling checked those boxes on paper, but a social observation is what truly hooked him. Sending someone your booking link carried a quiet stigma. It felt one sided, essentially asking the other person to do the work of finding time on your calendar. He saw an opening for a scheduling tool that treated the recipient as a participant instead of a supplicant. That became SavvyCal's founding wedge: features like overlaying your own calendar on top of someone else's availability so booking feels genuinely collaborative rather than transactional.

His deeper motivation was the kind of company he wanted to run. Level had been a big swing, with a potentially huge market but a lot of uncertainty and, in his assessment, too many headwinds for a bootstrapper to clear. With SavvyCal he wanted something calm and durable instead: bootstrapped with TinySeed backing, profitable, small team, long time horizon. Six years in, that is still the shape of it, even as the market has shifted underneath him with AI agents beginning to change how scheduling actually happens.

Derrick wrote the first line of code in early 2020 and spent roughly six months reaching a private early access version. The stack was Elixir and Phoenix, a language he fell in love with during the Level days and never looked back from. Six years later it is still the foundation, and he considers it one of the best technical decisions he has made: the platform has scaled with him without ever demanding a rewrite. Today the stack is Elixir and Phoenix on the backend, React on the frontend, and Inertia.js wiring the two together.

The trickiest part of building a scheduling tool, unsurprisingly, is calendar sync logic and time zones. Two way syncing with Google Calendar and later Outlook, handling time zones, recurring events, buffers, and every edge case around when a person is actually free is genuinely gnarly infrastructure work. Derrick spent a large share of those first six months getting that plumbing solid, on the reasoning that a scheduling tool that double books someone even once has lost that customer forever.

On the product side, he resisted the temptation to reach feature parity with Calendly before launching. Instead he built around the wedge: the polished booking experience, the calendar overlay that lets recipients compare against their own schedule, and personalized links. The bet was that a smaller product that nailed the feeling of scheduling would beat a bigger product that treated it as a commodity checkout flow.

Derrick charged from the start. Early access users paid, which kept the feedback signal honest, because people say very different things about a product once their credit card is attached to the opinion.

The two products now run on genuinely different models:

Meetings taught him that a good product in a crowded market can win a durable niche, but later stage growth gets difficult once competition turns aggressive and price points stay low. Appointments answers that directly by moving down the stack into infrastructure, where the buyer has a harder problem, compliance creates real switching costs, and contract sizes reflect it. He genuinely enjoys playing in both spaces at once.

The biggest structural challenge in the scheduling market is that the category leader offers a generous free tier, and every major productivity suite now bundles some version of scheduling for nothing. You can absolutely build a great business inside that environment, but you are always swimming against the question of why anyone would not just use the free thing.

That reality shaped everything: pricing, positioning, and eventually the decision to build a second product entirely, where the buyer has a harder problem and free is not a real option on the table.

If he had to start over, Derrick says he would find his niche faster and sharpen his positioning from the beginning. In the early days especially, it is tempting to say yes to anyone willing to pay for the product. Learning to say no to the wrong customers turned out to matter as much as saying yes to the right ones.

For Meetings, the early playbook was audience first. Derrick had been building in public for years before launch, podcasting, writing, and showing up consistently in the bootstrapper community, so a group of people were already primed to want to see it work. From there, growth ran through a set of compounding channels:

For Appointments, the playbook is nearly the opposite: outbound leaning and relationship driven. Growth runs through inbound demo requests from the site, qualification calls, and formal quotes. The most interesting lever has been what Derrick thinks of as an anchor tenant strategy: landing one credible customer inside a vertical, telehealth for instance, creates the case studies and compliance posture that make the next five conversations noticeably easier.

He is candid that he has never found a growth hack that actually mattered. What compounded instead was trust: an audience that already knew him, a product that impressed the people who used it, and now a compliance story that enterprise buyers can independently verify.

Derrick is direct about the human infrastructure behind six years of building. His family comes first. Bootstrapping solo means the highs and lows follow you home, and his family has supported the endeavor through a failed product, the lean early years, and every season the business needed more of him than usual. He does not think he would still be doing this without that.

Other founders have been just as essential. Founding is isolating by default, and nobody else on his team carries the particular weight of owning the whole thing, so he leans on a web of relationships with people running similar businesses. Some of his best strategic decisions started with another founder asking him one uncomfortable question on a call.

The institutional versions of that support have mattered too. TinySeed gave him a batch of founders navigating the same problems and a network that keeps paying off years later. MicroConf has been his professional home for over a decade, the source of mentors, friends, and early customers, along with a shared philosophy about building calm, profitable, founder owned businesses. His plain conclusion: if you are bootstrapping completely alone, you are playing on hard mode for no real reason.

From here, Derrick plans to keep executing the craft. He genuinely loves the work itself: designing products, writing code, talking to customers, making a business run well. The goal has never been to escape the work; it is to keep getting better at it and to keep building things worth building.

In the near term, that means growing both SavvyCal products and continuing to innovate in scheduling as AI agents take on more booking tasks. He has already shipped an MCP server so AI assistants can book, reschedule, and look up availability directly. His hunch is that a meaningful share of scheduling activity will shift from humans clicking calendars to agents negotiating times on their behalf, and he wants SavvyCal to be natively good at that shift rather than catching up to it later.

Longer term, he would like to eventually realize the fruits of the labor. He is in no hurry, and he is not building to flip, but playing the bootstrapper game well means knowing that patience paired with a strong, profitable business gives you options when the right moment eventually shows up. As his friend Rob Walling likes to remind his audience, everybody sells, eventually.

You can learn more about SavvyCal directly. Derrick's personal home on the internet is derrickreimer.com, and he is active on X.

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