Jovan Cicmil's Blog - Startup

The Time a Guy Spent $600 in 5 Minutes on My Freemium App

November 17, 2022

I used to run a fantasy football (soccer for Americans) game that I built myself. I learned many different things from that experience, from bootstrapping a company to negotiating an exit. This morning, I remembered an interesting tidbit that I’ve never written about — the time a guy logged in and proceeded to spend $600 on upgrades for their fantasy team. Context About 97% of my ...

Five Lessons I Learned Bootstrapping a Fantasy Sports Company

February 21, 2022

I was a bootstrapped founder before it was cool. Back in 2013, when it was all about building a startup and jumping through the funding loops, I bootstrapped a fantasy sports company. It was profitable from the first month. I ran it for a few years before finally selling to a larger competitor. Along the way, I learned a ton of important lessons. Here are the main ones. If you’re ...

Inside the War Between Domain Flippers and Startup Founders

November 26, 2021

No, not the real world. The digital world. I observed the latest battle personally so that I can report to you from the front lines. A well-known entrepreneur recently announced that he had bought a .com domain for his company. That’s not big news until you hear the rest: it took 6 years of negotiating and $100,000 to get that domain. His announcement prompted a war of words between his ...

Why MRR Is Misleading To Potential Investors

November 11, 2021

MRR (Monthly Recurring Revenue) is an excellent metric for operators of subscription products. It’s an easy way to keep track of your company’s recurring revenue, especially if you offer several subscription packages. What it is not, however, is a measure of a company’s value. A concerning trend in the world of indie ...

Why You Should Hire Freelance Workers for Your Startup

July 16, 2021

Those of you who have been reading my work know that I’m a freelancer, entrepreneur, and writer. But did you know that I’ve also hired over 20 freelancers on various platforms over the course of the last decade? Hiring remote talent can be a daunting prospect. Many still shy away from it because a simple Google search can reveal a hundred hellish experiences suffered by other would-be ...

Why So Many Startups Fail Miserably After Raising Money

June 24, 2021

Roughly 90% of startups fail. This statistic isn’t surprising, but the way many founders lunge into business, you would think that the failure rate is more like 2%. Having been following the industry for over a decade, I have noticed some patterns — ideas that sound enticing, plausible, or even brilliant. Ideas shiny enough to attract massive investments before crashing into the ground ...

How to Turn Your Employer Into Your First Customer

June 3, 2021

Imagine this. You drag yourself out of bed in the morning. It’s a rainy day and your commute to the office is hell. The soundtrack you play in your car doesn’t even come close to drowning out the sound of horns and engines. By the time you arrive at the office, you are stressed, apathetic, and counting the seconds until you can drive home again in that same rush hour traffic. In the ...

Most Entrepreneurs Fail To Understand Competition

May 10, 2021

How many ventures do you think fail because of infighting? How many fail because of market changes outside the founders’ control? How many fail because the product just isn’t good enough? If I had to venture a guess, I’d say your answer to all the above questions is “many”. Maybe you’ve been a part of one such story. But have you ever considered how many ventures fail ...

The Rise of the Indie Hackers

April 12, 2021

Remember when half of the tech world were startup founders and the other half were aspiring startup founders? When startups became all the rage, they redefined how new companies are built. Terms such as product-market fit, idea validation, and growth hacking became part of the day-to-day English language. And who could forget the mom test? The lean startup methodology took over the world, ...

How To Invest in Yourself Like a Growth Company

January 21, 2021

Some of the fastest-growing companies in the world are losing money every year, and yet investors have more and more faith in them each year. The bottom line remains negative, and the stock prices are soaring. Why is that? It all comes down to why the bottom line is negative. The fastest-growing companies often lose money for years because they’re reinvesting all their profits into better ...

How I Negotiated the Sale of My Bootstrapped Business

December 2, 2020

There are probably more articles out there about starting a business and running a business than you can read in a lifetime. But, what about selling a business? If your business is successful, you will eventually want to cash out. For major successes, this can take the form of going public by listing the business in the stock market. For minor ones, you will usually be acquired by a larger ...

Price’s Law Is Going to Kill Your Company

February 20, 2020

Have you noticed how, in every group, team or organization, a small number of people seem to be dragging everyone else forward? Whether you’re in a group chat organizing a trip or in an office building a startup, do you sometimes feel that a few people are pulling more than their fair share of the weight? Well, there’s a name for that. Physicist and historian of science Derek John de Solla ...

How I Built, Promoted, and Sold a Product with No Investments and No Marketing Budget

January 14, 2020

It doesn’t even involve a special kind of product, but it does entirely hinge on your relationship to the product. Eight years ago, I was a beginner programmer with little technical experience and no business acumen whatsoever. I had built no interactive websites, published no viral apps and written no recondite articles on software architecture. What I had was a desire to play fantasy football ...