Four months ago I started a company called ChallengeBox. At the time, my other startup called Decisive was struggling through a pivot.

Despite being written up in Forbes, and MediaPost and New York Times. We were having a hard time selling the software to large companies. Around thanksgiving of last year we had to lay off our team and put Decisive on hold. The timing couldn’t have been worse. It was one of the hardest things I had to do, and right around the holidays was crushing.

I still had confidence in Decisive but I couldn’t figure out how to scale an enterprise software business quickly. I had spent years on Decisive and I wanted to prove that what I learned from Decisive would work.


After spending time with family for the holidays, I began thinking about what I wanted to work on this year. I came up with ChallengeBox as a concept. In about a week I pulled together a site, and started to focus on customer acquisition. What started out as experiment grew very quickly. Fast forward 16 weeks ChallengeBox is business, added over 2,000 members and generated over $150,000 in revenues.

I really enjoy building businesses and helping other entrepreneurs grow their businesses faster. I’ve aways had this idea of helping lots of brands use social to grow very quickly. Here’s a post I wrote about it last year.

Here are a few of the lessons that I’ve learned from running Decisive that helped us grow so quickly.


Data is the lifeblood of ChallengeBox. It helps me make decisions faster, and get the most out of all of your work. So before I launch I ensure that my business is instrumented.

Here’s are the analytics that I set up before launching:

  1. Add Google Analytics tags.
  2. Set up Goals in Google Analytics. Goals tell me what channels are driving customers. Here’s a great explainer for how to set up goals.
  3. Ensure that I have heatmap trackikng. It’s extremely important for me to understand how people are interacting with the site. Heatmaps allow me to do this. I usually use Mouseflow because they have a free plan to get started.
  4. Set up Google and Facebook remarketing pixels. Every visitor from the day I launch likely has some level of interest in what I’m offering. I want to be sure I can reach those people after they’ve left. Remarketing can be an extremely cost effective way to do this. Here’s an explanation for how to set up Google Remarketing tags. Here’s an explanation for Facebook remarketing tags.
  5. Set up link tracking. As I post across social media make sure that I’m tracking links. Bitly is awesome for this.


Once the site is set up I wanted to put ChallengeBox in front of as many people as fast as possible. Before launch I always ask where will I distribute this product? I think of myself as Starbucks or McDonalds. Where are the busiest street corners with the right people to place my store.

I tested the following free channels:

I also emailed a number of blogs and I was able to get ChallengeBox written up a blog post for Style Magazine.

For paid tests I ran advertising campaigns across Facebook, Google and Twitter. More on that later in the post.

The goals of testing distribution are three-fold

  1. Understanding whether people will actually pay for your product.
  2. Getting feedback (both likes and dislikes) about your product.
  3. Listening to the actual words people use as they describe your product. You can use these in testing landing page copy and ad copy in the future.


After running all of these tests I determined that Facebook was the best place to spend my time. Our audience was there, and I knew that it could scale.

I spent a few days in Facebook groups just listening to what people were saying, what jokes they made so that I could understand what types of content to create.

We created a few posts that were shared a ton such as 100 awesome resources that will make you happier with your Fitbit.

4. 1–10–100–1000

With ChallengeBox Now that you’re all set up to collect data about your progress, its team to. You’ve got to prove it. I wrote this blog post about “Proving It“, and it has become my blueprint whenever I’m launching a new product.

1–10 Customers — The first ten customers were based on some manual work. I interacted with people on Twitter who were interested in Fitbit and fitness and posted to forums. This was great to prove that someone would actually pay for ChallengeBox. It was also key to learning about what I needed to say as I thought about how to reach even more customers.

10–100 Customers — I determined that Facebook would be the best channel to focus on here. I achieved this through testing out of variations of Facebook ads.

100–1000 Customers — After a couple of weeks of testing I was able to determine out which content and which targeting worked best to acquire our first 100 customers I began to increase our daily spend to about $300–600 per day

1000–10,000 Customers — We’re putting in place the infrastructure to scale to our next 5x. Facebook alone won’t get us there so we’ll start to expand to investing in, and optimizing other social platforms.


With content and ads I test everything. I look at ChallengeBox as one huge experiment. I tested different content formats. Images versus video. I test different images, headlines, descriptions. I tested multiple variations of landing pages.

We found that videos definitely work better than images, for driving conversions. If you can test basic videos for Facebook I highly recommend it.

Adespresso is an invaluable too to helping you quickly test and iterate through Facebook ads.


Through testing I’m always looking for two things.

  1. Does a channel work?
  2. Is it scalable?

It seems that finding scalable channels is where companies hit a wall. Influencers are an awesome way to jumpstart a community but they may not scale cost effectively.

Most people are afraid of spending on advertising. However if you get it right it is one of the best ways I know to truly accelerate your growth. I was able to generate over $150k by spending $40k. Worth it? I think so.

The key is finding what works. For ChallengeBox so far, after our initial tests we ONLY focused on Facebook on Females in the US on iPhones. These users have converted the best.


There is still TONS of scale here, and once we are ready we will expand beyond this target audience to Android, and then males and then International.

Building and scaling successful subscription business is not easy. There are so many mistakes I’ve made in building ChallengeBox which I’ll share (part 2 of this post). However I’m excited about building it.

This post was originally published on GrowthStory.co

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