Today is January 10, 2021—exactly four years since I published the first post on this blog, announcing to the world our intent to start building Outseta. It feels a bit crazy to be writing that and it also feels like we’re at a point of transition.

In many ways it feels like we’ve graduated—from being a pimply faced, early stage start-up teenager to a young company that’s blossoming into its potential. We’re undoubtedly more excited heading into 2021 than we’ve been at any point in our start-up journey so far.

This post serves as our four year update. Each of our previous updates, starting with our launch announcement, can be found below.

• Meet Our New Software Start-up, Outseta
• Outseta Two Year Update
• Outseta Three Year Update
  

Let’s get right into the good stuff.

Equity Allocation

We’ve continued to use a very simple formula to distribute equity amongst our team—we all value our time at $100 per hour and anyone on our team can contribute cash to the company as well. At the end of each year we look at the total number of hours we’ve all worked plus the cash contributions we’ve each made and we use that to calculate how much equity we each hold in the business.

At the end of 2020 our equity allocation breaks down as:

• Dimitris 36%
• Dave 34%
• Geoff 27%
• James 3%

For the most part, we’ve continued to work primarily for sweat equity in the business so we can reinvest our revenue into the company. James, who works in a much more part-time capacity than the rest of us, has earned a mix of equity salary since he started working on Outseta. On September 1st of this year, I (Geoff) started drawing some salary from Outseta for the first time. We’d reached the point where we definitely needed more help and beginning to take some salary afforded me the opportunity to spend more time on Outseta and less time consulting.

It’s also worth noting the $1,572,200 number your see at the top of the 2020 column. Over four years this is really the cost of bringing a software product of Outseta’s scale to market. But as you’ll see as we get into our expenses, the vast majority of that figure would go towards salary that we haven’t taken.

Expenses

We’ve been really disciplined about keeping our expenses as low as possible since we started building Outseta. This goes back to our operating agreement, our desire to stay intentionally small, and our focus on profitability.

We’ve now spent a total of $123,335.23 on Outseta over the last four years. Our expenses have scaled up from about $8,000 in 2017 to about $57,000 in 2020. The primary driver of that increase was starting to draw some salary from Outseta this past year.

On the marketing front, we’ve focused almost exclusively on “free” marketing tactics to date—partnerships, content marketing, and email marketing. Our biggest lines items this past year were:

• $2,500 to be a Gold Partner with Makerpad
• $1,200 for a Pro subscription to Wistia

The partnership with Makerpad was a critical step for us as we increased our focus on serving the no-code community. And while Wistia is a significant line item, we use video liberally for both marketing and customer support—and they’re a team I’m nothing but happy to support.

All things considered, I think our expenses are a strong data point that you can bootstrap an extremely ambitious software product into existence for a lot less money than you might think. While $123,000 isn’t a small amount of money by any means, that’s spending incurred over four years.

Marketing Results

One of my favorite aspects of being a marketing founder is that I’ve gotten to build every aspect of our customer acquisition process from the ground up. I’ve used this, quite purposely, to prove a point I’ve always advocated for—the metrics marketers are most often held accountable to are bullshit.

Website traffic? Vanity metric. Twitter followers? Nonsense. MQLs? There’s just no value in arbitrary lead quotas. None. They hurt more than they help.

All that matters in marketing is how many buyers actually show up with buying intent. That’s it. Jay Acunzo captures this approach beautifully:

Our numbers reflect this approach. We have quite modest website traffic and our number of account sign-ups each month isn’t eye popping, but the quality of our leads is exceptional.  We get remarkably few low quality leads—I’d say at least 80% of our account sign-ups are founders of SaaS products or membership sites that are a great fit for Outseta. And if you think about it, that makes sense—almost all of our website traffic comes directly from Stripe, Webflow, IndieHackers, Makerpad, or content that I’ve written about bootstrapping subscription businesses.

With no pressure to hit some arbitrarily set marketing metrics, I haven’t had to turn to more “top of the funnel content” or other channels that would drive less qualified traffic to our site. And perhaps most importantly, this approach fits our strategy—because we want to stay intentionally small, from a resourcing perspective we’re better off with a lower volume of highly qualified leads than a higher volume of less qualified leads.

Here are our top performing lead generation channels.

The channels aside, our website traffic and account sign-ups continue to grow by more than 100% year over year. We had about 40,000 visitors to our site and just over 1,300 account sign-ups in 2020.

While these numbers likely seem quite modest to many people who are reading this post, I am immensely proud of them. The lead quality that I referenced is one reason, but more than anything I’m proud that our team has resisted the urge to invest in growth prematurely.

Custom Success. Unit Economics. Then Growth.

This framework from Mark Roberge is by far the most important piece of start-up advice that I pass on to everyone who will listen, and we’ve truly held ourselves accountable to it. Our product and conversation rates simply didn’t warrant heavy investments in growth until recently.

Could we have grown a bit faster? Absolutely! But it would not have been efficient or healthy growth for a bootstrapped company. Our conversation rate from account sign-up to paid customer doubled in 2020, and more recently with changes like these we’ve 3Xed our average monthly conversion rate.

Heading into 2021… watch out!

Product

On the product front, man-oh-man am I a nuisance. I’m the primary liaison between our customers and our product team, and both our customers and myself ask for a lot. With a product as feature rich as Outseta, there’s a never ending list of feature requests and improvements that our small team needs to navigate.

But in my eyes 2020 was the year where our product grew up.

We sell to markets of extremely knowledgeable and demanding buyers, and for the first three years we were in business, it was hard for me to shake that our feature set was very limited, the product was buggy, and when you’re competing against heavily VC backed companies it was just hard to feel proud of what we had out in the market.

“This year, for the first time, I looked at Outseta and said to myself...we’ve got a pretty remarkable little product here.”

I knew I’d been holding back from saying that, literally, for years. But for the first time, I knew it was true. We still have plenty of rough edges and endless improvements to make, but I believe we now have the single best product for a bootstrapped founder to use to launch a subscription business. There isn’t another product on the market that offers the feature set that we do.

The velocity of product improvements that Dimitris, Dave, and James shipped in 2020 was borderline absurd. Some product highlights from this year include:

• We completed the “no-codification” of Outseta
• We added the ability to sign up and login users with Google
• We became SCA compliant for our customers in Europe
• We added the support for discounts and coupon codes
• We added the ability to setup protected content and account specific pages (unique dashboards each user can access upon login)
• We made improvements to give our customers much more control over their own email deliverability
• We launched revenue reporting
• We completely redesigned our knowledge base tools
• We built integrations with Circle.so and Rewardful

Final Reflections

As I look back at 2020, and even the last four years, I mostly feel pride. This is kind of a funny statement, because we’re not as far along as we’d hoped to be four years into building Outseta. As I reflect on the last four years, here’s what we could have done better and what I think we got right.

What we could have done better

When I consider what we could have done better, a few topics immediately come to mind.

First and foremost, I think we were too slow to move into the no-code space. When we were first building Outseta, we set out to serve founders of other SaaS start-ups—in most cases, developers. We saw the inefficiencies in the status quo of integrating dozens of point solutions and we attacked it. But while we wanted to serve other software founders like ourselves, I think our early results spoke for themselves and we learned a lesson the hard way—while our team looks at the world through a “let’s do more with less” lens, the vast majority of technical founders simply don’t.

The predominant mindset of developers is to over-architect their tech stack in the early days, and most will happily throw money at buying any software tool that they think might help them at all. We were too slow to say, “OK, our value prop just doesn’t resonate strongly enough with most developers.” For the no-code audience, our value prop could not be stronger—we should have made this move sooner, and as a result we’re playing catch up a bit with some of our competitors who started their companies well after we did.

Second, for me personally, I’m not sure I’d try to bootstrap a project as ambitious as Outseta into existence again. We’ve had this quote in the “Our Story” page of our website since the day we launched Outseta.

“The most valuable asset a startup can buy is TIME. Everything always takes two times longer than you think.” — Chris Heivly, Co-founder of Mapquest, EIR at Techstars

We knew this going in, but even with that knowledge, this has proven to be true.

When we started Outseta, we specifically took on a really ambitious all-in-one product largely because we were looking for a project that was big and meaty enough to keep us engaged for 10-20 years. We got one! Haha.

But for me as an individual, I’d bought my first home—which was a stretch financially—just months before we started Outseta.

Bad timing.

And in the midst of building our start-up, I started a family for the first time. Over the past four years I’ve made about 50% of what I was making prior to Outseta—that’s a significant sacrifice for my family to make over 4 years. I’ve probably left over $400,000 in salary and benefits on the table over that time, precisely when I could have used that money most.

That’s been financially stressful, and with the number of more founder friendly financing options out there these days, I don’t think I’d embark on this same path again. It’s not that there’s anything wrong with bootstrapping, it’s more a matter of the compatibility of this strategy with the size of the product we chose to build and my life circumstances at the time. But that’s mostly behind us now, and the past is to my benefit at this point.

What I think we got right

What I’m most proud of by far is that we’ve hung tough—through a pandemic, through a shift in our target market, through (for me) starting a family in the midst of our start-up journey. We’ve been tested and our team has shown real endurance and grit.

I think a lot of start-up teams that have built successful start-ups before are surprised when they don’t have the same level of success as quickly the second time around—that’s certainly true of us. But the benefit of our past experiences was we planned for this at the outset and structured our business from the ground up so that we could survive almost indefinitely—that’s probably the thing we got most right.

Through it all we haven’t wavered, once, on building this company our way and on our terms. We didn’t pursue growth prematurely when so many other companies would have. And we’ve continued to work together because we’ve been philosophically aligned on how we want to build Outseta and what we want to get out of it. It’s been a grind but it’s been incredibly rewarding to be a part of this team.

I’ve always said our two unfair advantages are:

• Development firepower
• A truly long term approach

These things remain as true as ever, and that’s a terrifying combination to compete against. The fun is just getting started!

-Geoff, Dimitris, James, & Dave