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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.

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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.

features

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 getpoindexter.com. 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!

  1. 1

    Hey Brandon, really enjoyed the interview and found Poindexter interesting as well, going to give it a try myself. Out of curiousity, would you be open to discussing scaling your acquisition on a revenue-sharing model?

    1. 1

      Thank you for the comment! We have a partner program you can read more about here: https://getpoindexter.com/partners

      Feel free to reach out if you have questions.

  2. 1

    Brandon, awesome interview. Always interesting to hear those stories that start out with a need (often in times of bankruptcy, death, and other major life events).

    I wanted to get hear a bit more about the technical challenges you encountered, do you have an email I could reach out to? Let me know, thanks!

  3. 1

    Hey man, great job with Poindexter; I had tried it before but this reminded me of it and so I punched in all the numbers for my other business; super helpful!

    Your valuation result in particular got me excited; since I graduated from university 8ish years ago I've had a goal to create a million dollar business, and little did I know that I've already passed that mark by an extra half million! (just on paper at this point, but still...it was a nice moment :-))

    I want to give you a few pieces of feedback:

    1. You know how Facebook and other products talk about their "aha!" moment, where if a user experiences something, they are probably going to stick? That valuation measure was it for me; now if someone comes calling looking to buy, I've got something backing up my valuation.

    2. I immediately thought to myself, I want everything this app has to offer. So I'm setting up the tracking section, and it says I have upgrade to see actual results. No problem, I expected that and I'm happy to pay whatever price you're asking at this point. I'm ready to pull the trigger on the Starter plan, but I just want to check to make sure it will actually use the data that I have. My question basically is, what integrations do you support? And nowhere on any of your pricing pages do you offer that information.

    So now I'm a little reluctant to upgrade because I couldn't find that information and I don't want to throw money down the drain. I have to go into your footer, into the support knowledge base, and read the article about tracking before I realize, actually, there are no integrations, you have to enter it manually.

    1. Obviously my last piece of feedback here is: please, add integrations! Personally, Stripe would be the best one for me, and Zapier would work too.

    I understand that you're having some challenges on the tech side; if there's anything I can do to help, please let me know. All the best!

    1. 1

      Hey Keith, thank you for the detailed reply! Your feedback is spot on. Integrations are going to be the next big push after we release the feature we're building right now. We're thinking about starting with accounting platforms like Xero and QuickBooks since they tend to be centralized sources of financial information. If a Stripe integration would be more useful for you I would love to talk about it further!

      1. 1

        In general I agree about the accounting systems, I currently use Bench for my bookkeeping and I don't think they have an API so that wouldn't be an option for me.

  4. 1

    Excellent interview, Brandon!

    I've been happy to be one of Poindexter's paying customers and loudest cheerleaders since very early on.

    Poindexter is hands down The Best Way to plan your business.

    You come away with so much more than a fantastic business plan (which you do), you come away with a living, breathing plan that you can keep up-to-date with new market realities.

    This is amazing because, pre-launch, your plan is full of assumptions and optimism. We all know that no plan survives first contact with real, paying customers. :) What you really need most, then, is a plan that can adjust to actual conditions on the ground as you face them. Poindexter is so great at this.

    With other methods of creating a business plan, you're left with an ominous stack of excel spreadsheets that—let's be honest—you're just never going to keep updated. They're created (IF you create them, so many entrepreneurs are skipping this step these days) just to satisfy a pitch deck or banker, then abandoned.

    Any new business idea I have—no matter if it's a new product line, a new marketing funnel, or an entirely new startup—immediately goes thru “The Poindexter Test” to see if I can foresee a way to turn it into a profitable reality. And yeah, to be honest, most of my initial assumptions are 99.9% wrong, so I have to go back and revise and adjust. Poindexter makes it super easy to keep my plan up-to-date.

    I'm currently working on a free video guide that quickly walks through exactly how I use Poindexter and how you can, too. It's not quite done yet, but if you're interested in seeing something like that, drop your email in here and I'll give you a shout when it's ready to see: https://training.mastermindjam.com/poindexter-interest-optin

    1. 1

      Hey Ken! Thank you for the comment :) You've been such a great supporter of the product from the beginning, and without customers like you, I would've moved on to something else a long time ago. I just signed up for your training, and look forward to learning more about how you use Poindexter. I'll definitely use the opportunity to understand where we can make the experience even better!

  5. 1

    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.

    This is so awesome. As an indie hacker, I've had trouble with this too. I didn't know, for a long time, that marketing could be genuine and helpful, so I kept spamming people and feeling spammy. Heh.

    Years later and I'm much more confident about reaching out to someone in a genuine way and seeing if we can help each other. This has led to better, stronger, warmer relationships that make me enjoy marketing instead of running away from it (really fast!) :)

    I'd love to hear more about how you found people you connected with and reached out in a way that wasn't purely financially motivated. What strategies did you use? Did offer some service for free?

    1. 1

      Hey David, thank you for the reply! I couldn't agree more. One thing I did that ended up saving our Product Hunt launch was joining Startup focused Slack groups. I joined purely with the aim of making some new friends and helping in any way I could. It seems like such a rare approach these days, but some of the members took notice and came running to our aid when our PH debut almost went up in smoke.

      1. 1

        That's awesome! I've been thinking about joining WIP.chat, but I'm not sure. Which ones have you had a good experience in?

        I was watching a live coding session by an indie hacker the other day and I was so impressed by how well he kept in touch with all of his communities as he was developing the product. I don't know if I could split my focus that well — it was cool to watch!

        1. 1

          IndieHackers is a great place to get started! One thing that helped me was scheduling a specific time every day to focus on building relationships and helping others. It's a great habit to get into :)

          1. 1

            I'm going to try this. :)

        2. 1

          I'm a WIP.chat member, and I can highly recommend it!

  6. 1

    Great writeup! "Run towards the work"... I like that!

    1. 1

      Haha, thanks! I can't take full credit though. Got that one from Andy Frisella on the MFCEO podcast :)