Bootstrapping Ad Reform: 1 year from launch

Having finished the first year in the creation of a SaaS business, I can confidently say that this is the most difficult stage of building a business that I’ve experienced. Once you’ve found product market fit, it becomes a bit more of a science. Product market fit, and doing it bootstrapped, is certainly an art. There’s been good and bad, both company-wise and personally, and many lessons learned along the way. Let’s start with the good 🎉

The good

It was Halloween & my bday so 🎃
  • Crossed the 10+ customer Mendoza Line(users in 7 countries) with 122% retention rate (knock on wood), including some pretty great brands.
  • Became Ramen profitable 🍜
  • Launched 3 paid products within the platform (Screenshots, Ads.txt Pro, Ad landing page QA)
  • Launched a free tool that’s used by thousands of ad tech folks on a monthly basis (
  • Welcomed a new addition to the Ad Reform fam (Kyle’s daughter Emma) and learned my wife and I would be joining the baby party in 2018
  • Hired and worked with 3 great interns/contractors
  • Raised $0. Not opposed to raising money if it makes sense, but very proud to be bootstrapped. Also, hard to do any of this without the super strong/supportive women in our lives (Tonni & Claire 🌹)
  • Moved into a new office in Midtown Atlanta. Thanks for paying it forward Tope & team Calendly

However, it’s been tougher than I expected. Starting a business is hard, and starting one for the first time is even more challenging. So I figured we’d share some of our biggest challenges, in hopes to help others that are starting businesses.


Product Prioritization

The biggest challenge for me personally has been product management. We have a good combo, Kyle builds and I sell/market. We lean on our experience and strengths, but neither of us has much experience in ad tech specifically. Like our last company, Rigor, we’ve leaned heavily on the feedback and needs of users, which worked relatively well for us in the past (grew to $3mm ARR).

However, this can sometimes feel like you have no clear direction. You just sort of build based on the next couple potential customers that show up. This can create technical debt and features that get neglected over time because that one high paying customer asked for it that one time.

We’ve certainly fallen into this trap a bit, but we’ve tried to optimize based on how we gather feedback, how we manage it, and our process to building features (I’ll talk about our work cycles shortly). One thing we’ve learned is that it’s important to understand why someone wants a feature and what goal they’re trying to accomplish with it. This gives you a much clearer picture of what would make sense for you to build. The user is the expert on their problems, the software company is the expert on building software to solve that challenge. We’ve learned to not reverse those.

We’re actually in the process of building a product for managing customer feedback that we’re tailoring to our needs. We may make the product publicly available, so be on the lookout for more from Userfeed down the road.

Life happens. Embrace it. Keep grinding.

In our first year from launch, life’s thrown us good and bad curveballs. On the good side, Kyle had a newborn and I’ve got one on the way! On the bad side, we’ve had things like grand jury duty pop up. About 3 months in, half of our team of two (me), had jury duty 3 full days a week, for 2 months! Starting a company bootstrapped is hard enough, you throw something like that into the mix, and it feels nearly impossible. Honestly, it was a super difficult time emotionally, because I didn’t have much time to spend working during a critical time in our business. We weren’t growing much, I was having to push customer support work on Kyle and an intern when I couldn’t whip my laptop out between 1 of the 100 cases we listen to per day, and I felt like I was letting people down. I felt helpless for the first time in my career. But, like any challenging time, it didn’t last forever. We made it through and we kept grinding. If you start a business, you will experience these moments. Embrace them. Keep grinding.

Work Cycles

We spent two months building the MVP for our first product (Screenshots), and about one month iterating on user feedback before we brought on our first paid customer. Since we based most of our product direction on customer feedback, we found that we needed to get MVPs out quickly so we could get to the iterations quickly, too.

We decided to implement a process that we call work cycles (inspired by Basecamp’s process). We work on 1 or 2 big batch items (big new product/feature) and 5 to 8 small batch items (New on-boarding messaging, marketing site updates, bug fixes, etc.) for 4 weeks. At the end of the cycle, we ship. Then we spend 2 weeks iterating, working on internal tools or side projects, and figuring out what we will do in the next work cycle. This has given us more focus and sped up our process a bit. (Also, we name our work cycles based on cocktails).

Always look to invest in things that give you time

Your time is so valuable. You can’t afford to spin your wheels on anything for too long. Over the last year, we’ve run into multiple situations that became time-sucks, and we either built or bought solutions to give us time back:

Alerts when users do certain things in the app: We added a service add-on to one of our pricing plans to give customers a higher level of support. We need to scan over screenshots in our app to look for anything that might have been out of the ordinary (pop-ups, brand safety issues, etc.). We used to just watch Fullstory after the fact, which worked okay, but we really need to know when a user was doing things in real-time. Kyle ended up building a Slack integration to alert us when the customer did certain things in the app.

Trial outreach: I ran sales at our last company, where we had a super high-touch process with potential clients. ~90% of our leads were generated with outbound sales/BDRs. We didn’t have a self-service sign up process, which hurt us a bit. We had to schedule a demo before the customer could trial the product. We held multiple calls with the client throughout the trial. Plus, all of our contracts required sending emails and documents back and forth.

When we started Ad Reform, we wanted to build a lower touch, self-service product with an on-boarding process similar to that of Calendly or Mailchimp. It didn’t start out this way, but we’ve automated each step over time. We started by implementing a self-service subscription process with Stripe:

Our next project was to introduce a scalable on-boarding process. When we started, I was reaching out to leads manually upon signup and during trials. To improve this, we implemented Intercom, which has a pretty awesome startup plan for just $49/m. We built out an automated on-boarding process, which includes:

  • An email upon sign up
  • An in-app message for a first-time user (linking them to KB)
  • An email reminding the user they have 3 days left on the trial
  • An email notifying the user that the trial has ended, offering a link to the upgrade page, and or asking for any feedback
  • A knowledge base (complete with Loom videos)

No pop-ups on every marketing page asking if you need help. We aren’t big fans of that experience so we didn’t want to force it on our users

Here’s a link to awesome examples of SaaS on-boarding that we used for inspiration.

Lead research: As simple as it sounds, doing research on new inbound leads takes time. We found a simple way to automatically pull in company and contact data by connecting Mailchimp, AmpleMarket, andSlack. Mailchimp builds a list of leads, AmpleMarket fetches research on the person and their company, and we get notified via Slack:

Talk to other entrepreneurs

Starting a business is incredibly isolating, especially if you spend a lot of your time working from home. When you go through the inevitable struggles of bootstrapping a business, you need other entrepreneurs to talk to, even if it’s just to vent. While it’s good to have folks you can talk to who have had big successes, it’s just as valuable to meet with entrepreneurs who are going through the same struggles at a similar stage to you. It helps you understand that you’re not the only one experiencing certain challenges. Don’t go through it alone!

Do things that don’t scale, but learn when to stop

It’s important to do things that don’t scale. It’s how you learn from your customers and build great experiences from the beginning. One of those things is customer support. We try our best to respond to a customer immediately, regardless of the time. We have customers in just about every time zone, so this means sleeping with our phones on ring, keeping our laptops by our bedside or taking them out with us just in-case. There were many nights we’ve woken up at 3:30am to help a customer or trial user. This has helped us gain customers and has played a part in the 122% retention number, but it’s not sustainable. At a certain point, we realized this, and made sure to set a certain expectation with our customers. Do things that don’t scale, but not at the detriment of your well-being 🙂


I feel good about where we are as a business, and I’m excited about year two. By no means have things been perfect, as it has certainly been tough at times (both business-wise and personally). However, I wouldn’t want to be doing anything else, with anyone else. One thing I’ve learned is that is what’s really important. The outcome is important, of course, but it’s not the ultimate goal. What’s important is to go after your goals with all you’ve got. So many people don’t. If you’re on the fence, half the battle is just taking that leap.

We look forward to continuing to build on year one, and we look forward to sharing more learnings as we go.