I love the concept of documenting your progress and setbacks. It allows everyone to gain insight from what you're doing and for you to look back in 10 years and see how far you've come and how hard you worked to get here, every step of the way.
For a long time, I've wanted to capture and share my own thoughts, experiences, and setbacks as I embark on the long and thrilling journey of entrepreneurship; bootstrapping a digital business.
My goal with these letters is to keep them succinct and action-oriented so that you may learn and acquire insights into how to build and scale a digital business.
The letter's name is The Unconventional Kind. I like this name because I've never been the kind to go with the crowd. I've always advised people to follow their passions rather than listen to what their surroundings say, because they often don't or can't understand your ambitions and goals.
My parents are my greatest supporters, but they don't fully comprehend the nature of my business. They want the best for me, but they, too, were unsure whether I would be able to “make it work” with no degree.
Digression, but I began writing a book called "From Sheep to Shepherd" when I was 18 years old, and the message resonates with the name of the letter. It was about following the unconventional path.


I don’t think I’ll be writing much about myself and my story in this newsletter—maybe I’ll do a podcast episode someday revealing all of that—but I figured I’d share a little about myself to get you on the same page as me and understand who’s behind this.
My name is Benjamin Akar, and I decided to leave university to pursue a career in technology. At the age of 19, I was hired as a frontend infrastructure developer for the world’s second largest classified company, where I was responsible for building developer tools for the rest of the company (500+ employees).
I spent a few years there, but quickly realized how slow-paced larger corporations are, and how little influence you have. You can probably guess what I did.
I switched jobs.
I started working as a Full Stack Developer for one of the most intriguing startups right now, Sanity. I worked on projects for enterprise customers as well as the open source community.
Despite being surrounded by so many highly skilled people at the job, I was feeling a little off every day. It took me a while to express it in any way. But then..
Seeing the hard work and challenging tasks at Sanity brought back memories of wanting to build something myself. The impressive product made me wonder why I hadn't started something like it myself.
Despite the fact that it was a great place to work, I left after five months to pursue my passion of building a business. I didn’t want to look back in 10-15 years with regret for not taking the leap of faith and building a business sooner.
I'm currently bootstrapping Braum, AI personalization software for digital marketplaces, with my childhood friend. We want to make personalizing content experiences simple, which will result in happier customers and more sales.
Leaving a consistent income, although a difficult first step, was in the bigger picture the easiest thing I could’ve done.
The difficult part starts now.