Analyzing markets for months before finding the right idea and building a 5-figure MRR product
After Derrick Reimer sold Drip, he took a big swing and failed. Then, he built and sold a small company. And now, he's building SavvyCal, a two-product portfolio bringing in a five-figure MRR.
Here's Derrick on how he does it. 👇
Two exits, one failure, and another success
I'm a software developer turned founder. I started Drip, an email marketing platform, which we grew and sold to Leadpages in 2016. After that, I took a swing at a team chat product called Level (a thoughtful alternative to Slack) that didn't pan out. Then, built StaticKit, a forms-as-a-service tool that found modest traction before I sold it.
In 2020, I started SavvyCal, a scheduling tool that makes sending a booking link feel less one-sided. The product now serves thousands of customers and has been my main focus for the past six years, bootstrapped with backing from TinySeed.
SavvyCal is now two products. The original scheduling link product (now SavvyCal Meetings) is alive and well. Over the past year, I've been building SavvyCal Appointments: an API-first, HIPAA-compliant scheduling infrastructure product aimed at healthcare and SaaS companies that need embedded scheduling but don't want to build (or maintain) it themselves. Think of it as scheduling as a building block rather than scheduling as a destination.
I'm also focusing on what I'd call the "agentic" layer — we shipped an MCP server, so AI assistants can book, reschedule, and look up user availability. My hunch is that a meaningful chunk of scheduling activity will shift from humans clicking calendars to agents negotiating times, and I want SavvyCal to be natively good at that.
We're at 5-figure MRR. The vast majority of that comes from SavvyCal Meetings. SavvyCal Appointments is earlier in its revenue journey. It's a higher-touch, higher-ACV sale — infrastructure contracts with BAAs attached move slower than $12/month self-serve signups — so the revenue mix looks different: fewer customers, bigger contracts, longer sales cycles, and a lot of potential.
My team includes me, full-time in the US, a full-stack developer, and a support specialist. Small team, deliberately.
Finding the right market
SavvyCal came from a search for the right-sized problem. After Level didn't work out, I spent a few months deliberately auditing SaaS markets. I sought something with proven demand, recurring revenue, and room for a differentiated angle, rather than trying to will a new category into existence.
Scheduling checked those boxes, but a social observation truly hooked me: Sending someone your booking link carried a stigma. It felt one-sided — "Here, do the work of finding time on my calendar". I saw an opening for a scheduling tool that made the experience feel more considerate, treating 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 collaborative.
My deeper motivation, though, was the kind of company I wanted to run. Level was a big swing, with a potentially huge market but much uncertainty and probably too many headwinds for a bootstrapper. With SavvyCal, I wanted to build something calm and durable: bootstrapped (with TinySeed backing), profitable, small team, long time horizon. Six years in, that's still the shape of it. The market has shifted under us, with AI agents starting to change how scheduling happens, and what keeps me motivated now is that the "right-sized problem" turned out to have a much bigger second act than I expected.
Falling in love with Elixir
I wrote the first line of code in early 2020 and spent roughly six months getting to a private early-access version. The stack was Elixir and Phoenix. I fell in love with Elixir during the Level days and never looked back. Six years later, it's still the foundation and one of the best technical decisions I've made: The platform has scaled with me without ever demanding a rewrite.
Today, the stack is Elixir/Phoenix on the backend, React on the frontend, and Inertia.js wiring the two together.
The trickiest part of building a scheduling tool is the calendar sync logic and time zones (of course!). Two-way syncing with Google Calendar (and later Outlook), handling time zones, recurring events, buffers, and all the edge cases of "when is this person actually free" is gnarly infrastructure work. I spent a big chunk of those first six months getting that plumbing solid, because a scheduling tool that double-books someone even once has lost that customer forever.
On the product side, I resisted the temptation to reach feature parity with Calendly before launching. Instead, I built around the wedge: the polished booking experience, a calendar overlay allowing recipients to 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.
Charging from the start
I charged from the start. Early access users paid, which kept the feedback signal honest. People tell you very different things about a product when their credit card is attached to the opinion.
SavvyCal Meetings is a classic self-serve SaaS: monthly or annual subscriptions, priced per user.
SavvyCal Appointments flips the model: it's sales-assisted, usage-and-contract-based, and aims at companies embedding scheduling into their own product. Fewer customers, larger contracts, longer cycles.
Meetings taught me that a good product in a crowded market can win a durable niche, but later-stage growth can be difficult when competition is aggressive, and price points are low. Appointments answers that, moving down the stack into infrastructure where the buyer has a harder problem, compliance creates real switching costs, and contract sizes reflect it. I enjoy playing in both spaces.
Competing with a free incumbent
The biggest challenge in the scheduling market is that the incumbent has a generous free tier, and every productivity suite bundles some version of scheduling for nothing. You can absolutely build a great business in that environment, but you're always swimming against "Why wouldn't I just use the free thing?" That reality shaped everything: pricing, positioning, and ultimately the decision to build a second product where the buyer has a harder problem and free isn't a real option.
If I had to start over, I'd find my niche faster and sharpen my positioning from the get-go. In the early days, especially, it's tempting to say "yes" to anyone willing to pay for your product. But sound strategy requires saying "no" to customers who don't fit the vision and preventing your roadmap from wandering too much.
Two products, two growth playbooks
For Meetings, the early playbook was audience-first. I'd been building in public for years — podcasting, writing, showing up in the bootstrapper community — so, at launch, a group of people wanted to see it work. From there, we used these channels:
Word of mouth via the product itself — every booking link shared is a small ad
SEO and comparison content
Podcast sponsorships
Extensive experimentation over the years
For Appointments, the playbook is almost the opposite: it's outbound-ish and relationship-driven. We grow through inbound demo requests from the site, qualification calls, and formal quotes. The interesting lever has been what I think of as an anchor-tenant strategy: landing one credible customer in a vertical (like telehealth) creates the case studies and compliance posture that make the next five conversations easier.
I've never found a growth "hack" that mattered. Trust has compounded: An audience that knows me, a product that impresses its users, and now a compliance story that enterprise buyers can verify.
The importance of community
People have been my greatest advantage.
My family comes first. Bootstrapping solo means the highs and lows follow you home, and my family has supported this endeavor through a failed product, the lean early years, and every season where the business needed more of me. I don't think I'd still be doing this without that.
Other founders have been just as essential. Founding is isolating by default. Nobody else on my team carries the particular weight of owning the whole thing, so I lean on a web of relationships with people running similar businesses. Some of my best strategic decisions started with another founder asking me one uncomfortable question on a call.
The institutional versions of that matter too. TinySeed gave me a batch of founders in the same boat and a network that keeps paying off years later. MicroConf has been my professional home for over a decade. I've found mentors, friends, and early customers there, along with a shared philosophy about building calm, profitable, founder-owned businesses. If you're bootstrapping completely alone, you're playing on hard mode for no reason.
Know what game you're playing
Here's my advice:
Pick your market like it's a cofounder, because you'll be living with it for years. I spent months considering different markets before starting SavvyCal, looking for proven demand, recurring revenue, and room for a differentiated angle. That boring diligence has paid off every single year since. Most indie hacker failures I've watched were market failures, not product failures. The builder did everything right inside a market that couldn't support the business.
Charge money embarrassingly early. Free users will tell you what's pleasant. Paying customers will tell you what's true. Every pricing decision I've agonized over proved less scary in reality than in my head.
Expect year one to be lonely and act accordingly. Find your people before you need them, whether that's a community like MicroConf, a founder group chat, or two peers you call monthly. The compounding value of those relationships is invisible at the start and enormous by year five.
And know what game you're playing. Venture-style swings and calm bootstrapped businesses are both legitimate, but they require different decisions from day one. A lot of founder misery comes from running one playbook while wanting the other outcome. Deciding on purpose is the whole trick (and probably worth putting on a Post-it note by your monitor).
What's next?
From here, I'll keep executing my craft. I genuinely love this work: designing products, writing code, talking to customers, making a business run well. The goal has never been to escape the work; it's to keep getting better at it and to keep building things worth building.
Near-term, that means growing both SavvyCal products and continuing to innovate in scheduling as AI agents handle more booking tasks. A real shift is happening, and I want SavvyCal to define it.
Longer term, I'd like to realize the fruits of the labor. I'm not in a hurry, and I'm not building to flip, but playing the bootstrapper game well means knowing that patience and a strong, profitable business give you options when the right moment shows up. As my friend Rob Walling likes to remind his audience regularly, "everybody sells."
You can learn more about SavvyCal at savvycal.com. My personal home on the internet is derrickreimer.com, and I hang out on X/Twitter.
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