Launching a cryptocurrency startup—more volatility than an actual cryptocurrency

The story of winning the Product Hunt Global Hackathon, losing everything, and how I bounced back

Alex Miles
6 min readFeb 20, 2018

The past 4 months have been the absolute hardest in my career, yet by far, the most rewarding. I’m incredibly excited to re-launch TokenTax.

TokenTax is the easiest way to get your cryptocurrency taxes done right. We ensure your data will be accurate and optimized for savings.

The Story

Over the past year, I’ve really grown to love cryptocurrency but I’ve always been on the conservative side of investing. You know, doing what’s easy, setting it and forgetting it.

In October, with the charts beginning to skyrocket, I thought to myself, “Danggg, how am I going to report my cryptocurrency earnings?” After trying a few different tools, I realized they all felt like an overflowing, kitchen sink filled with dirty dishes and two semi-brown sponges (which one should I use???).

I wondered why no one built a tax tool for cryptocurrency. One with a focus on great user experience and one that solves the core problem extraordinarily well. Doing my taxes, and getting out of my hair.

By mid-October, I had a tiny team together to build what was the first version of TokenTax. The plan was to build it and submit it to the Product Hunt hackathon. We proceeded to build the first version and out came TokenTax 1.0.

I knew we had a good product, but I had no idea we’d win the Grand Prize in the Product Hunt Global Hackathon!!! I was in shock. We were up against ~4,500 makers!

Pause: This is where the valley happens

As things started to heat up, the cohesiveness of the initial team fell apart. We decided to part ways and following weeks were a very low point for me — sometimes I felt completely lost. I wasn’t sure what I was going to do and how to overcome this. Thank you to everyone who reached out, mentored and advised me through the challenges, and encouraged me to get back to work. This was one of the most challenging things I’ve had to face head on and I now feel stronger having gone through it. Better prepared to tackle even bigger obstacles in the future. Here’s what I did…

Enter TokenTax 2.0

One of the best things I did for myself after was to remain hopeful and put myself out there. Trust me, this did not feel intuitive, and was direct advice from the people I love.

Thankfully, I had a place to go. I’m a member of CryptoNYC, a wonderful co-working space in NYC filled with smart people from a variety of backgrounds. Every week on Tuesdays, they host a brown-bag lunch and have speakers present something they’re working on or discuss a topic in the space.

One week, I presented TokenTax and in the crowd was a fellow named Zac McClure. As people were introducing themselves, he said he’d been helping friends navigate the murky waters of cryptocurrency taxes. Zac received his MBA from Wharton and has been working in finance, tax, and strategy consulting for the past 10 years.

Over the next couple weeks we rebuilt everything from the ground up. The codebase, the interface, the accounting algorithms, the backend, the frontend, and the companies foundation.

Once we knew the plan we got to work. We put our heads down, hired amazing people, and built an amazing product. Thanks to Zac we created an algorithm that actually saves you money.

How to succeed when the world seems to be against you

Through this experience I’ve learned a couple of fundamental ideas first hand, and I plan to carry these lessons with me going forward

1. Collaboration wins

By working with people from different backgrounds, amazing things emerge. It allows you to move quickly and autonomously without getting caught in the details. This hits on trust too. If you believe someone does great work, let them run with it and amazing things will happen.

In the weeks prior, I met an amazing group of new people who all had sharp and unique perspectives on building software and finance companies. Stoking this cross pollination enabled us to build something awesome.

2. Focus wins

Cryptocurrency needs focused products that solve a core problem extremely well. Numerous crypto projects out there seem to have dozens of features ranging from portfolio tracking to communities. To me it feels like they forgot to clean up those dishes 😹.

TokenTax is focused on getting users the best 2017 tax outcome possible. And we will build from there.

A good example of this in the space is Coinbase. They do one thing and they do it damn well (relatively speaking) — they’re the easiest place for new investors to buy cryptocurrency with dollars.

3. Empathy wins

This applies to both customers and the team. By employing empathy in your conversations, you drastically improve the likelihood of making great work. I did the best I could to understand the intricacies of accounting, what makes a great tax product from an accounting and a customer perspective. The easiest way to do this is step into the other person’s shoes. Ask them to teach you!

4. Empowerment, trust, and responsibility win

When I was an employee at Readmill, one of the best parts about working there is that I wasn’t allowed to make anything other than my best work. It flat out wasn’t acceptable. This felt amazing.

I was empowered to make my best work. People trusted that I’d eventually do this, and I felt personally responsible for achieving this. It was enforced by the founders, the developers, and every other function of the company.

This has been how TokenTax has been operating since re-incorporating and it feels great.

The product and company

What we stand for

We believe in a decentralized and open financial future. Cryptocurrencies are a transformational technology and we want them to stick around.

The current use case is investing and with investing comes responsibility. This means people need to report their investment returns to the IRS.

Up until now, the process of remaining a good actor by reporting taxes in the new system has been an after thought. Primarily because people think the government isn’t paying attention (they are) and they can’t catch them (they will).

We intend to keep the community safe by providing tools for people to easily play by the rules while still maximizing their returns. In affect, maintain the thriving environment of cryptocurrencies and contribute toward it’s long term success.

Real people, real tax advisors, real help

At TokenTax we pair our customers with on staff tax advisors to make sure your cryptocurrency data is right. One of the biggest challenges with cryptocurrency taxes is the spectrum of exchange data quality. When you pair that with investors of varying levels of experience, it’s going to get messy. This makes it really hard to know which numbers are correct or incorrect, but luckily we can help.

When in the product, message us if you see and error and we’ll make sure your data is right.

Maximize your savings

We determine the optimal tax lot that should be sold to minimize your tax burden, for every trade, across all of your exchanges and wallets.

All the exchanges

Use our CSV uploader to import on the unlimited plan to upload your transactions from any exchange.

A lot more to come

We’re just getting started, and there’s a lot more to come. Our focus is on making your tax experience great.

Thank you!!

Thank you for reading this far! I’m incredibly excited about what we’re shipping today, but we have a long way to go.

Thank you to everyone that help me out, took phone calls, connected me with folks, and most of all supported me through the experience.

Sign up for TokenTax today!!

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Alex Miles

Founder of @TokenTax. Previously product design at @dropbox @readmill