Bootstrapping to 7 figures while competing with best-in-class tools

After falling into the startup world, Geoff Roberts teamed up with a former employer to build a solution to tool sprawl in small, recurring-revenue businesses.

Since it was an amibitious project, he and his cofounders committed from the get-go to work on Outseta for fifteen years. Now, they're nine years and seven figures in.

Here's Geoff on how he's doing it. 👇

Accidentally getting into startups

I accidentally found my way into the world of tech startups. I went to college to major in writing, but when I graduated in 2008, the economy tanked, and prospects for professional writing or blogging didn't look good. So, I got an MBA and was eventually hired by an early-stage startup in Boston called Buildium.

This didn't sound exciting to me, but I needed a job — and, little did I know, I was walking into a great situation. I was employee #7 at Buildium. Most of the team were engineers, and the company had found product-market fit. They hired me as the first full-time marketer and gave me a ton of freedom to figure out how to grow the business. During my five years leading marketing at Buildium, we grew the company from a startup to $20M in annual revenue; they sold Buildium a few years later for $580M.

Dimitris Georgakopoulos, one of Buildium's cofounders, then became my cofounder at Outseta. Reflecting on all the software tools we cobbled together to support an early-stage SaaS business at Buildium, we recognized that nearly all SaaS companies cobbled together a tech stack of payment tools, authentication, CRM, email, and help-desk software. Everyone needed these tools, yet everyone reinvented the wheel — integrating tools instead of building software incurred a real-time cost. So we set out to address that. Our goal was to deliver all the core software infrastructure needed to launch and grow an early-stage SaaS company. Think "Shopify for SaaS."

We've worked on that for the last nine years, and our business has expanded to support use cases ranging from SaaS products to membership sites to online courses. Outseta can build any recurring-revenue business where customers pay for access to software, content, or tools.

We don't share revenue publicly, but we are a low 7-figure business.

Long-term bootstrapping

Outseta is a hugely ambitious software product — it's really more like five software tools than one — and we decided to bootstrap it. We knew delivering something "good enough" would take a long time, and we set out to build this business with a 15-year timeline.

After three years of effort, we were only at around $1500 in MRR. Around this time, a global pandemic hit, my wife and I lost our primary sources of income, and we also found out we were unexpectedly having twins. At this point, almost any reasonable person would have quit.

But our team believed an integrated solution was better, and we believed the need for our tools was "durable," so we kept at it. As the product improved, we eventually hit an inflection point. And nine years into this now, I'm happy I continued, despite our lean early years.

Learning from best-in-class software

Outseta offers nothing particularly unique — payments, authentication, CRM, email, and help desk tools are all well-known software categories. Outseta's differentiator is that it uniquely brings these tools together in a single platform, so our customers spend less time wrestling with their business's software infrastructure.

We started building the initial product by meeting one day in Boston and examining all the best-in-class software tools across these categories. We drew inspiration from Chargebee, HubSpot, Intercom, Zendesk, Mailchimp, Auth0, ChartMogul — too many tools to mention here. We extracted the parts we liked and left the "fluff" at the door, while also specifically looking for ways these tools could be more powerful if they communicated without custom-built integrations. Our product today offers countless examples of this.

Then, we started building — email, payments, authentication, CRM, and help desk — roughly in that order. We built it with .NET for the backend and Angular/React for the frontend. We host the product on AWS. And we run the business on Outseta — we were our own first customer.

It took about two years to deliver an MVP that was "good enough" to win business across these feature sets.

Aligning interests

Our business model is simple — we charge a combination of subscription and payment processing fees.

We want our software to be accessible to early-stage companies, so we give all of our tools away at an artificially low rate. For $37/mo, you access payments, auth, CRM, email, and help desk tools that would cost many multiples of that if you cobbled together a tech stack on comparable point solutions.

This gets us "in the door" — then we only grow when our customers grow by taking a 1% fee on successfully processed payments. This aligns our interests with our customers nicely.

Search and integration partnerships

We've grown primarily through search, content marketing, and integration partnerships.

Regarding search, a challenge is that the core software categories we compete in — payments, CRM, email, etc. — are so competitive that it's not worth targeting any of those keywords directly. We're never going to outrank Hubspot for CRM, Stripe for payments, or Mailchimp for email. It's just not happening. So we've leaned into "membership software" as the best-fit, well-understood software category, even though it doesn't perfectly describe what we do.

For content marketing, I primarily write about my entrepreneurial experience as a founder. You can find much of that writing on our blog. I view this as an investment in our brand, but since our audience also tends to be other founders, it directly contributes to new customer acquisition. That's really fun for me — this interview is a perfect example.

For integration partnerships, Outseta is a "headless" business or membership management tool that integrates with almost any website builder or development framework. As a result, we integrate with many tools. Webflow, Framer, Squarespace, Stripe, Notion, Discord, and Circle have all been important to our growth, in addition to code-based integration examples.

The problem with selling to small businesses

We've had our challenges, and almost all of them tie back to:

1. The size and scope of what we decided to build as a bootstrapped team.

2. Selling to early-stage businesses.

Regarding #1, we knew we would face longer timelines because we wanted to stay small and independent — but we truly meant our commitment to devote the next 15+ years to building this business.

As for #2, selling to small businesses means we have relatively high churn rates, and customers primarily churn because they close their businesses. This creates a perpetual headwind for growth, and we've needed to learn to account for it — i.e., we must keep customer acquisition costs extremely low, as this drags down customer lifetime value.

Ultimately, I would not recommend selling to startups! All common advice on this topic is correct — focus on customer segments that are more stable and have more budget.

A game-changing organizational model

Outseta's organizational model is our biggest advantage — it's also a major reason our cofounding team decided to work together. We wanted to show that a small, experienced team could compete with much larger companies with the right incentive structure and organizational design.

We called this our "Build your own adventure compensation model." The basics are simple:

1. We operate Outseta without hierarchy.

2. Everyone receives the same pay — a full-time Outseta salary is $210,000 per year.

3. Everyone can choose to work 1 to 5 days per week.

4. Everyone can also elect to work a portion of their time for equity in the business, and everyone earns equity at the same rate and terms as the founders.

Everyone at Outseta today owns a material portion of the business, ranging from 2% to 29%. This model is not for everyone, but it has been insanely effective at aligning our team, allowing everyone to work autonomously, and creating a pretty crazy inbound recruiting pipeline when we need to hire.

Three things you need to hear

First, more indie hackers should consider building projects in pre-existing markets. Doing so greatly de-risks things and almost guarantees some level of success if you stick with it long enough — because buyers exist!

Second, the market you're in will dictate your growth more than anything else — so choose wisely. In a good market, everything feels easy. In a tough market, you can execute fantastically well, and everything still feels hard.

Third, I advocate for a framework relevant to SaaS growth that Mark Roberge (Hubspot's first CRO) shared with me — he calls it Customer Success, Unit Economics, then Growth. The idea is simple:

1. Figure out how to make customers successful with your product by any means necessary; it doesn't have to be cost-effective or scalable.

2. Only once you've done so, figure out how to make it cost-effective (unit economics).

3. And only once you've done that, focus on growth.

This may sound obvious, but almost everyone launches an MVP and then immediately focuses on growth. Almost every problem in SaaS ties back to this.

What's next?

My goals are to have a great relationship with my family and friends, and to have as much fun as possible. I believe in fun as a KPI — you may have $100M in revenue, but if I'm having more fun, who is really winning?

An enjoyable life certainly includes working on something meaningful. For me, that means building a company I can be proud of, and my goal focuses on our team. When this is all over, I'd love to have 10 or 20 people turn to me and say, "Thank you for building Outseta this way. This company allowed me to do what I wanted with my life." In my eyes, serving the customer really, really well is a pre-requisite — unless we do that, we can't offer the opportunities that I'd like to our team.

I want to create a workplace that allows our team members to chase whatever excites them in life — where they cherish, nurture, and work hard on our business because the company also supports their life outside of work. Work-life harmony is a two-way street.

To learn more, Outseta.com is the place to go! You can also find me on Twitter, Bluesky, or LinkedIn.