Lessons I Learned From Going Broke

We always hear about founders risking it all to go after their dreams. The Zuckerbergs of the world. The Bezos’s.

These stories dominate the discourse.

We never hear about the Janahan’s of the world - risking it all. And losing it all.

In June 2015, I quit my full-time software engineering job to start a company in forensic finance called Quotail - with two friends.

I had nine months of funds. And an obsession. To find bankers front-running mergers and acquisitions by looking at trades in the options markets.

Front-running is trading on non-public information in anticipation of the stock price going up or down.

I had dreams of quantifying front-running for my own benefit.

I wanted to be rich enough that I'd never have to work again. I wanted a money machine.

But instead all I got were these lousy, life-altering lessons.

Don’t Take So Long To Ship

It took us six months to ship a v1 of the product.

We had nine months of runway. That left the team with only three months to find customers, take feedback, and implement it. That timeline put a ton of stress on us.

Years later, one of my co-founders, Amir, admitted he went into $10K of credit card debt during the last 2 months. We all underestimated how long it would take to ship a v1. We were too naive to cut scope.

We thought the adding features would make the product.

But paying customers make the product.

Keep A Straight Face While Asking For Ridiculous Shit

“How much would you need to white-label the APIs for our customers?” - Optionshouse Brokerage
“$44,000/month” - me (with a straight face)

While trying to find customers for Quotail, we tried cold calling hedge funds and selling subscriptions to consumers.

Hedge funds rarely pick up the phone. And when they did, they told us they had built systems in-house to find front-running.

Consumers expected tools for free from their brokerages.

Brokerages give tools to their customers to encentivize them to trade more.

Brokerages (used to) get rich on commissions.

Optionshouse asked us, Quotail, if we could handle 5,000 customers.

Our product, when scaled to 5K users, cost $22,000/month to run. We wanted 100% profits. Anything less would have trapped us.

They wanted to pay $8,000/month. The gap was wide. Huge.

But it taught me that when negotiating - I have much more room than I assume.

Don’t Take Such A Big Bet

After the negotiations with Optionshouse fizzled out, we shut down Quotail.

We all got jobs. I told myself I’d never try entrepreneurship again. It was demoralizing to spend nine months and all of my savings - only for it to fail so hard I had to go back to a job.

It didn’t feel good to ask for an advance to move into a new apartment.

After that, I didn’t build a software product for 5 years.

But in 2020, I learned my mother tongue, Tamil. Not knowing Tamil was painful for me. I thought that language would die with me.

So in 2021, I set out to build a software called TamilApp, by myself, to help others learn Tamil.

This time would be different. I didn’t quit my job. But, it took me six months of nights and weekends to build.

I soft launched it to 30 potential customers who expressed interest.

After I talked to them, I realized it solved the wrong problem. It taught formal Tamil, when 95% of people wanted to learn colloquial Tamil.

I made the same mistake as in Quotail - taking too long to ship v1.

Money isn’t the only dimension to size a bet on. Time is just as important. If not more.

Keeping both small is risk management for morale.

My First Small Win

In 2022, I started writing online after Write Of Passage 8. I write about tech, learning languages, introspection, and food.

I wanted to figure out what mattered to me.

Each essay and newsletter is a small entrepreneurial bet. A tiny one.

I took my best performing writing and shared it on Twitter. Two tweet threads got me from 300 to 1200 followers. Those threads were about how to get promoted and how to ask for a raise.

Around that same time, I came across a community called Small Bets. It was a group of people who also learned the hard way that risking it all isn’t a good look. They introduced me to the idea of creating info products from highly engaged writing, rooted in my own experiences.

I assumed building software was the only way to be an entrepreneur. I was wrong.

So I took my best performing writing, augmented it, and bundled it into a video course called “How To Get Promoted Beyond Senior Engineer” on Gumroad.

Thirty hours of work. Filmed and edited it over the weekend. Released it January 15, 2023 on Twitter.

I expected it to sell 5 copies, but it has sold 85 so far. $2500+ in revenue.

I made more revenue on that video course than we did for the entirety of Quotail.

It’s easy for me to admit I can’t tell the future. It follows that I can’t tell what bet will pan out and what won’t. Since I have a limited time on Earth; for me to be eventually successful - I need to place as many bets as I can.

I don’t need any one bet wiping me out.

You don’t either.