How A Close Call with Bankruptcy Became My Inspiration for an App

Hello! What's your background, and what are you working on?

Hey, Hackers! My name is Brandon Crossley, and I'm the founder of Poindexter, a simple financial planning application that helps entrepreneurs make smarter business decisions.

My journey started out working on the business side of things for a startup building a Facebook game back when those were big. Unfortunately, the product was never “good enough,” so the launch was in constant delay, and I soon found myself without a job. A good lesson to learn early. ;)

After that, I worked in management consulting for a bit, but I constantly found myself looking for something more entrepreneurial. Soon enough, I stumbled across the perfect opportunity. My Dad's business was failing and he needed help. Working with him, we narrowly escaped bankruptcy, and it was this experience that gave me the inspiration for Poindexter. I realized that existing financial tools were too reactive, and I wanted to help small businesses get a better grasp of their finances without hiring expensive consultants, so we built Poindexter.

We’ve been on the market for two and a half years and currently serve 1,000 monthly actives while generating $1,106 in monthly recurring revenue. This month also marks our first licensing agreement with a major U.S. university, which has been a long time in the making.


What motivated you to get started with Poindexter?

Timing is a weird thing. Toward the end of the experience with my Dad, I had been learning about UX design and practicing my skills on an absurd app I thought I wanted to build. Friends then started asking me to help work on their ideas, and soon enough I had pretty consistent contract work designing and prototyping apps. It was fun for a while, but I knew I wanted something of my own. It wasn’t until later that I connected the dots leading to Poindexter. Once I did, I knew it was the thing I wanted to build.

To avoid some previous mistakes I’d witnessed, I began by publishing a simple landing page with nothing more than a text description of what I wanted to build. I then ran a Google ad to see if anyone would sign up, and much to my surprise, they did at a rate of nearly 15%. That was all the motivation I needed.

At the time I had about $30K saved up, and some design work going on the side, so I thought I could launch Poindexter with enough runway to figure out whether it could work. Definitely not the most detailed plan.

What went into building the initial product?

Due to budget limitations, I knew the initial functionality had to be minimal. However, don’t think for one second that stopped me from including way too many features. My idea of an MVP was certainly distorted by excitement.

I immediately started building a financial modeling framework that could apply to every business model I’d ever encountered. Only once it was finished did I strip away any “non-essential” features, which was hard to do because they were all so important! This process took about three weeks in total, as I had a couple paid projects to contend with.

Once the modeling was complete, I began designing the wireframes in a similar fashion. Three weeks later, I emerged from the depths of a dark underground bunker with the perfect prototype, gifted to humankind by the gods of blind creation.

As the prototyping phase came to a close, I met a freelance developer through a college friend, and he agreed to build the app for my $15K budget if we used Ruby. Done deal.

After four months of dev and one month of testing, we officially launched the app following our debut on BetaList in early May of 2016.


How have you attracted users and grown Poindexter?

Initially, my launch strategy was lacking. My basic idea was to start by submitting Poindexter to BetaList—an early adopter platform for finding new startups—and figure it out from there.

At the time, BetaList only accepted pre-launch startups looking to grow their waiting list. To make the most of any traction, I waited until we had a finished product, and put up a temporary landing page to meet their guidelines. During our debut, we captured more than 300 sign-ups, and the following Monday I sent an email to our list announcing the “launch” of our live product. Interest was still high, so 215 people visited the site, 73 of which signed up immediately, and one person even upgraded to a paid plan! Not the best conversion rate, but it was a start.

For the next few months, paid customers trickled in from word of mouth, but the rest of our go-to-market was still taking shape. Overall, our efforts fell into three main categories: leverage existing audiences, contacting one-to-many organizations, and showing up in the right place at the right time.

Leverage Existing Audiences:

Being a complete novice, I started by focusing on activities I thought would have a quick return on investment. Things like reaching out to tech reporters, bloggers, and influencers, engaging in spammy social media practices, and other tactics often falsely referred to as growth hacking. I must admit, this was a low point for me. It reeked of desperation and didn’t represent my brand in a positive light. If you’re launching a startup for the first time, please don’t do any of this. It’s much better to develop relationships with people by caring about their goals and providing value without expecting anything in return. This approach takes much longer, but things have come back around in ways I could never foresee.

Develop relationships with people by caring about their goals and providing value without expecting anything in return.


One-to-many Organizations:

Our product is designed for a specific audience with a particular pain, and they tend to seek the support of other organizations for financial help (i.e. accelerators, incubators, accountants, etc.). I started reaching out to these organizations via cold emails with the goal to learn more about how they work with startups and small businesses to see whether there was an opportunity to provide some value. This strategy didn’t work very well, since adding an intermediary often meant solving for the needs of the middleman instead of our customers.

Right Place Right Time:

Potential customers were already searching online for a solution to the problem we solve. I knew showing up in those searches required a good strategy and a lot of time and energy—an idea I wasn't ready to accept at first. Ultimately, this method is the main reason Poindexter is still around. Once we focused on creating quality content for targeted keywords, we started seeing results. One of the biggest lessons I’ve learned is to run toward the work. It pays off because others tend to avoid it. This single focus took us from around 20 visitors per day to over 100 today.

What's your business model, and how have you grown your revenue?

We originally launched with a freemium model to figure out if people would pay. I didn’t have the funds to keep it going very long without revenue. We priced the product along the lines of similar solutions and got the validation we needed, but after a little research and customer feedback, we changed to a three-tier subscription with a free trial. Prices increased 250% as we maintained the same conversion rate, which helped grow monthly revenue from $623 in February 2018, to $1,056 in MRR by June.

Month Revenue
Feb ‘18 623
Mar ‘18 688
Apr ‘18 938
May ‘18 953

Choosing the right business model has been somewhat of a struggle. The need our product serves is only temporary for many customers, so churn is higher than I’d like. Subscriptions aren't the best option for short-term needs, but we have a plan to address this in the long run, so we're staying the course. Brian Balfour wrote a great series that helped me better understand this balance. We’re still working toward the market/product component of his diagram.

What are your goals for the future?

Our immediate focus is on fixing the business model. We’ve collected a lot of user feedback over the past couple of years, and have some great insight on how to make the product more relevant to users on a regular basis. However, there is some risk in doing this since we'll have to prioritize more strategic features over ones that enhance value for users signing up with short-term objectives.

Achieving our goals will be challenging, as our team is currently limited. I’m working on Poindexter on the side, and I recently had to part ways with my co-founder and CTO, but we are making enough money to move the business forward with some freelance help, so I’m confident we’ll overcome these hurdles.

What are the biggest challenges you've faced and obstacles you've overcome? If you had to start over, what would you do differently?

Honestly, that’s a pretty hard question to answer. Because of my ignorant strategy in starting the company, much of the experience has felt like an uphill battle. Aside from the lack of product validation, ill-conceived acquisition plans, investor and accelerator rejections, and broken business models, I would have to say the biggest challenge I’ve faced was choosing the wrong CTO.

If there’s an area of the business where you feel helpless, learn as much as you can about it and develop skills in that area.


As a “non-technical” founder, it was easy for me to explain away my concerns simply because someone had a skill-set I was desperately lacking. Co-founder relationships are hard, and they're one of the primary reasons for startup failures. It's not a smart move to choose someone just because it's convenient. If there’s an area of the business where you feel helpless, learn as much as you can about it and develop skills in that area. You will build confidence and be in a much better position to assess whether someone may be a suitable partner.

Have you found anything particularly helpful or advantageous?

My answer here isn’t sexy, but it’s driven most of our growth, which has been the result of an aggressive focus on learning. I can’t even begin to count the ways this comes into play. It extends beyond just picking up new skills and ideas, and reflects a sense of how I approach business from a fundamental level.

One example of how this manifests itself in our business is in the form of our customer service philosophy. We actively try to understand where we're failing users, and then take steps to fix common complaints. The responsiveness to customer feedback has resulted in greater loyalty and referrals, which was initially our main channel, and continues to play a significant role today.

For me personally, focusing on learning has helped me overcome a lot of challenges. It’s given me the confidence to continue moving forward when things were darkest and enabled me to pick up new skills that have made me more effective in my job, and in working with my team. I try to prioritize learning by focusing on the current challenges at hand, but some great books I’ve read recently include:

What's your advice for indie hackers who are just starting out?

My advice isn’t anything you’ve never heard before, but it’s the only reason we have a business at all. It’s pretty simple, start by solving a problem for a specific customer. Putting your faith in the problem instead of the solution helps you weather the months of stagnation, rejections, co-founder exits and anything else entrepreneurship throws at you. You can even do something stupid, like building a product from start to finish without any outside feedback, and still get people willing to pay for it.

One of the biggest lessons I’ve learned is to run toward the work.


Other than that, just get started. If you begin with this kind of focus, you can figure it out as you go, and pivot to a better solution as you learn by participating in the market. We’ve learned a lot this way, and our experience is why I believe Poindexter’s best days are in front of us.

Where can we go to learn more?

If you’re in the process of raising money for your new venture or just want to know whether your business strategy is financially viable, check Poindexter out at I also post on our blog and YouTube channel about business and financial topics from time to time.

If you have any questions or want to continue the conversation, leave a comment below and I'm happy to respond!

Brandon Crossley , Founder of Poindexter

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