Tips Bootstrapping to $1m ARR and Beyond

Heads up — this isn’t a growth hacking article. Or one where you’ll learn 3 things to grow your SaaS business overnight. If you’re looking for these tips, stop reading right here to save time.

Printavo is just over 8yrs old now and passed $1M ARR a few years ago. It was a big milestone for us as the company is bootstrapped, profitable, and felt like a true validation that we’re helping our customers. I wanted to share insight into getting there to hopefully help others and put this journey into perspective.

I went to the University of Illinois at Urbana-Champaign studying business but spent more of my time skateboarding, designing clothing, and doing freelance UI work. I loved freelancing and UI design plus it was great side cash. It eventually made me curious about how websites worked on the back-end so I picked up Ruby through Michael Hartl’s book and began making little apps to solve my daily needs.

At the same time, a clothing boutique owner, Dustin, in Champaign, IL asked if I wanted to purchase his screen-printing equipment. My friends and I sold t-shirts we designed through Dustin’s store and hung out there skateboarding at night.

We gathered our money together and bought his equipment for $6,000, setting up shop in the back of his building. It was exciting, being able to custom print limited designs like Johnny Cupcakes and The Hundreds (this was the 2009 era).

Very quickly, we began custom screen-printing for organizations on campus. We were printing for greek houses, clubs, bar crawls, you name it. I remember our sales hitting $10k/week which was insane as a college kid.

Eventually, things became unorganized. We were using Google Calendar, email, QuickBooks, Bamboo Invoice, PayPal, and paper was everywhere just to keep up. It was chaotic and I knew we had to simplify and streamline to continue. After looking for solutions, nothing was simple and easy to use.

I was a big reader of the book, “Rework”, by Jason Fried and David Heinemeier Hansson. Their thoughts around simplicity, underdoing competition, and focus on core elements weren’t present in the printing space. Everything wasn’t even cloud-based, let alone being god awful to look at (I love UI design, remember).

Well shit, why not build it then (as a young coder would naively say)! I knew we could use this and remember thinking that there has to be others out there that would too. I didn’t know about TAM, CAC, LTV, funding, seeds, unicorns, or donkeys. I just wanted to solve our needs.

I worked on Printavo tirelessly for almost a year while learning to code at the same time. Trying, testing, reloading, repeat. Eventually, Printavo was live in early 2012, deployed on Heroku, ready to accept customers! I quickly emailed a list of 70 addresses I had from early interest on forums and…

No one signed up. Nothing. Hmm, no worries, I’ll bring the price down from $49/mo to $19/mo, supply and demand right?

Nothing still. I even made the product free to attract anyone to start using it! Customers really didn’t like that, saying they were concerned with the longevity of Printavo if it was free and running their business.

I remember thinking, “WHAT DO YOU WANT?!”. I kept pushing changes, listened to feedback and repeated. Then one day, 3 months later, I got an email from Stripe “Payment of $14.99 from …”. I actually couldn’t believe someone paid me to use Printavo but there it was.

This begins the journey of going from $348 ARR to $1M ARR, profitably. Let me preface too, I was working on Printavo nights and weekends before going full-time in 2016 when we were at $330k ARR.

1. “WOW” Support

I can not emphasize enough how much value is added to your product by responding quickly and providing incredible support.

It can take days to months to build the right feature that a customer appreciates but responding back to a customer in a few minutes creates a “wow” experience immediately. Customers will even thank you for responding so quickly. The expectations bar is so low today for customer service which is to your advantage. If your customer calls Xfinity or ComEd, what kind of service do you think they’re expecting to receive? Now imagine you respond back to a question of a customer in 2 minutes.

Customers will stick with you longer, even with a smaller feature set if you provide over-the-top support for them. I used to hear this a lot: “Yeah, they don’t have the most features, but they’re there to help me quickly”.

This is so important that today, we strive for an average 20min response time and end up at 45min. We’re still working on getting there.

2. Quick Product Iterations

There’s a lot of debate around how many hours you need to work to be “successful”. I was working on Printavo most nights of the week til 1am after work. Granted, I have no kids and no wife at the time.

But, I busted my ass to iterate on Printavo quickly. It wasn’t a job for me, I was passionate about it. Working with customers that were in the same situation I was in at our screen-printing shop, helping them organize their business, designing new features, and building them. It was exciting and I spent every minute I possibly could working on Printavo.

I’m still obsessed with our customers, questioning how they do things, focusing on how we can help them further. This focus on our customers is what helped gain initial traction and propel us forward.

3. Community

Because I was involved in online forums for screen-printing, I was constantly listening and contributing. Just like how some know everything about sports teams, trades, and predictions, I was following the garment industry.

This helped do two things. One, it gathered an early group of beta testers to start giving early feedback on Printavo. And two, it legitimized Printavo early on in our space. I wasn’t “foreign” to the industry here to make a buck.

We still heavily invest in the community as I believe it’s crucial to a strong brand. We started an annual conference when we had 3 team members, created educational content, and provided business advice to help our customers grow outside of using Printavo.

4. Patience

Lastly, I never had and still don’t have a number goal, no focus on exits, and no focus on competition. Don’t get me wrong, we’re aware of the competition and outside forces, but it’s less than 1% of my daily thoughts.

The passion for helping our customers is our long-term drive. I play the “infinite game” (see Simon Sinek) and am constantly learning. Every meeting or interaction is approached as if someone is teaching me something new and the more we’re an underdog.

It took 2,069 days to get to $1M ARR and I had no expectation it would even happen. I loved the journey around helping our customers and this is where our focus lies.

Bonus

Okay! Want some quick tactical tips to help you scale?

• Retargeting Ads — Sign up for a platform to help you run this. Adroll or PerfectAudience will work great. Customers have to see your brand multiple times before they make a decision.
• Phone — Get customers on the phone and offer phone support. It legitimizes you a lot quicker and helps build trust, fast.
• Drip Email Campaigns — Create an email campaign using a tool like Intercom and automatically email new customers tips to help them get started.

Shameless Plug

We’re hiring! Printavo is looking for passionate team members in engineering, customer care, success, training, and marketing to grow our team. Say hi! bruce@printavo.com