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Why I started my own bootstrapped software business

Tom Zach
Software Engineer | Feel free to follow my journey on Twitter @magnificoder
Originally published at Medium ・5 min read

It all started off at the age of 7:

In hindsight, it all started very early. At the age of 7, I decided I need to find ways to make money. I went with my sister at summer time to sell lemonades at the beach. The business model was great: right at my own home I found 2 investors who happen to be our parents, and have funded the whole adventure. That meant that every dollar that we earned stay as our very own profit.

Some time later, I decided to extend my services, that included cleaning services, haircuts, deliveries, writing songs: all for a few dollars. Here’s an image of a “marketing brochure” I created at the time describing my services, hoping to count the dollars apparently. Not the best marketing image selection was it? ;)

My first marketing brochure

My first “Marketing brochure”, in Hebrew

Helping my dad with his business

It was at 2009 when my dad decided to quit his job at a hospital as the manager of the technical department, to pursue his own business of selling medical equipment.

At the time I was only beginning my career as a software engineer, and had a full time job.

Him being excited doing his own thing, and me being able to see it first hand was the first time I realized that one day I want to do the same.

He also needed my help. At weekends & evenings when I got back from work I used to work with him: building stock management software for his physical products, went to AdWords courses in google, learned about paid advertising, SEO and everything in between. We even flew abroad to conferences together and negotiated deals with equipment manufacturers.

It was a great experience, and even though not long after my dad decided having a business was not for him, the hunger for my own one stayed with me.

First international trip: enter the digital nomad dream


An image I took at the outskirts of Playa Del Carmen

It was late 2015 when I left my first job and went on my first trip that did not include a ticket back home. Amongst other places, I went to Playa Del Carmen, Mexico, where I stayed for over a month.

There, at a beach hostel I saw something I never thought I’d ever see: a person working while being on vacation.

I was shocked, and remember being “angry” at him, saying — why are you working now? You’re here to have fun!

He said: Yeah, at my job they don’t care where I’m at as long as work is being done. I’d just rather be traveling than staying at home all the time.

Little did I know this had a name: a Digital Nomad, and little did he know that from that day I swore to do the same.

Since I fell in love with the culture & beauty of Latin America, I made a rule that until I get my dream come true I have to be there at least for a month every year. Spoiler alert: That did happen.

Working at small startups

It was 2016 when I landed at my first tiny startup job. I remember asking recruiters to not send me any company bigger than 15 employees, since I knew that one day I’d start my own and thought it would be wise to learn how it is first hand first.

And boy did I learn the hard way: 10 months later the first startup ran out of money, so I had to find another one.

So I did, and again it was one of about the same size, ~15 employees.


Photo by Proxyclick Visitor Management System on Unsplash

2019: Forming my own business, and making the nomad dream come true

After almost 2 years working at the second startup, I started feeling the itch of traveling.

I had asked my boss to try and work remotely, but he said he does not believe in this type of working. I just knew it was time to resign, even though I loved everything about that job.

So I did resign, and have then created my own business. I packed my laptop and booked a one way ticket to Latin America. No plan, I just knew that once you begin you find your way with things.

One week before my flight, I met someone very interesting. He runs a site for greetings that is ranked very high in google. He monetizes this site using advertising. And said he knows he could probably make more money but doesn’t want to invest any time in this site.

I said, “hey: I’m a developer and am free. Let’s do something and split the money.”

Long story short: a day later I’m building a site that lets users take a picture & a greeting text, edit & send to their loved ones for birthdays, holidays, etc. I had done so in the airplane and after and couldn’t stop until it’s ready due to the excitement of having something that generates a passive income.

About a month later, it was ready, and is generating a few passive dollars every day to this day.

Seeing my business partner doing this, I just knew bootstrapping was possible. Since then I was determined to get to a point where I have a steady income from my own websites, as fast as possible.

That meant I had to start my own projects, and combined with inspiration from the indie hackers community it has given me the ideas that led me to 2 indie projects I’m currently working on: one marketplace, one Saas, which when the time comes(very soon) I will share more about.

As for the DN life — I had stayed a total of 6 months being a digital nomad, building my own things and trying to see if I can find remote work opportunities at websites.

Then came COVID, which made it easy to find remote work, but less to travel. But it’s ok since I’m back home focusing on growing my business.

Since the beginning of COVID and to this day, I am working part time as a freelance software engineer, while I pursue my indie dreams. Feel free to follow me on Twitter where I document the continuation of my journey.

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