Yash Chandra: Post

Summary

I remember vividly. It was Labor Day weekend in 2014. I was working as a Consultant at Deutsche Bank making real good money. This was my 10th year of Corporate Life and I was not at all happy with where things were going. Not because I had a bad job or low income. Not really. It was because I had the entrepreneurial itch and I was worried that I was getting too comfortable with my life and would remain a “Wantrapreneur” instead of doing something of my own. So on that day, like I had been doing for a couple of years, I went on flippa.com (place to buy existing websites/Software businesses) and decided to scroll through listings (a favorite pastime of mine even today), I realized that if I couldn’t build something of my own, may be I could buy something and grow it ? Yes, I am one of the earliest adopters in the whole “Micro SAAS acquisition” space which is very popular these days. I found an ed-tech side project (barely 4 months old) that had like 10 paying customers at the time and I decided to buy it. I thought “Heck, whats the worst that can happen ? Think of this investment as my MBA”. One of the biggest reasons I chose this business was the seller. He was really dedicated in building the project so far and was very open in sharing everything. It became my full time job very quicky beginning early January 2015 and still is. For all practical purposes, I am the founder of the business because everything about it has been changed since I took over along with type of customers, new business model, entire codebase, infrastructure and the vision/direction.

I cannot believe it is 10 years already. Over the years, I grew this side project from small 10 customers to few hundred customers and increased average customer ARR from $2500 to $12,000+. It is now doing low 7 figures in ARR which by most standards in business can be called a “Reasonable Success”. I am extremely grateful that I was able to get to this point. This post is going to be a long one where I will share all my successes, failures (many) and emotional rollercoaster that I have been through along with my team, customers and family as well.

What I succeeded at

Overall, I am happy with where I ended up at. Yes I didn’t quite build the big company or empire that I wanted but I am grateful for everything I was able to achieve. If I go back a decade, I will take what I have today. No major regrets. Some of my highlighted achievements:

I replaced my own corporate income by the 5th year of business and it paid for everything I have for last few years.
Built relationships with some great customers, many of whom are with us for 5+ years (our average CLTV is 3.5+ years)
I get to do what I love: Building and running a business
Staying bootstrapped and owning 100% of the business. No investors to answer to. Note that this can also be a negative at times (more on this in later sections)
Every day has been a learning. I learned how to sell, market, customer service, devops, servers, infrastructure, conflict resolution, hiring, firing and many more. Overall, I love being part of all of it.

What I failed at

Note that most of these failures below are based on my own goals. I am sure someone will read these and go “What the heck Yash. This is good enough”. Not for me though. I have set high standards for myself and I failed at the following:

I failed to build a big enough business. Yes it does low 7 figures in ARR but my goal was to hit at least $10M in ARR and after 10 years, it is a failure for me that I couldn’t achieve 8 figures in ARR. Yes, I am well aware that I am already in an extreme minority of founder who even hit 7 figures ARR. I was surprised to read somewhere that around 4% of companies ever reach Yearly 7 figures in revenue. There are various reasons for this failure. Some of them, I will talk about later in this post.
Even though I was able to build a decent enough team, I failed at hiring/retaining best talent for various roles. One of the issues could be the stunted growth of the company but I failed overall as a leader to attract the best people to work for us. Yes, I know this is a hard thing to do for anyone but I still wanted to do better in this area than I did overall for a decade.

The Hard Truth of running your own business

The grind gets to you sometimes especially loneliness. You may have a team (I have a small team of some great people) but being solo founder is incredibly lonely and hard. You just cannot share the feelings with anyone else because very few people can understand the emotions of being a founder.
Difficult to switch things off. You are always thinking about the business. Even when you don’t need to. Working in a regular job is different where no matter how hard you work during the shift, you can come home and not worry. It is not your baby after all. Business is different. You are always ON and that can be problematic especially with family members around you.
It mostly a boring job with constant challenges and fires to put out. Especially as a bootstrapped startup/small team with limited resources. I cannot forget the day when I was on a vacation with family in Miami and one of our customers database was corrupted and even though we were able to recover the data, I was up all night working from the Hotel to get this fixed. Not fun. Then in the morning, I had to go on a customer call and explain everything. No one was happy. Remember that things will go wrong if you have been in business long enough. Nature of the beast. Not for the faint of heart.

Figuring out Ideal Customer Profile (ICP)

Majority of businesses fail due to the inability to achieve Product Market Fit (PMF) and/or figuring out who the Ideal Customer is. The ones that don’t quote fail struggle to grow if the ICP is not clear. This is what happened to us for a while especially during a period of 2021-2023). You cannot scale a company if you have not figured out who the best customers are. The best customer for your company/product are those who really solve a burning problem using your product and is a problem that they want to continue solving over a long period of time and not just one time. These are the customers who keep coming back to you for more and are using your product the most frequently. These customers also pay well and don’t balk at the price of product.

At my company, this took a while to figure out. Actually, we sort of knew after around 3 years in business but I personally did not want to admit that because I wanted to build something bigger for a much bigger audience. One of the reasons why revenue growth stalled a bit (between 2021-2023) was the fact that I experimented trying to sell to various types of audiences even though the signs were clear who our best customers were already.

Hiring success and failures

Hiring is one of the hardest things to build and scale a company. I would even argue that it can harder than getting customers. It is hard because the first 10-15 hires at a startup need to be more of Pirates and Romantics (as the great SAAS OG Jason Lemkin explains)

First let’s talk about failures. I have plenty when it comes to hiring. For a long time, I just didn’t pay attention to hiring the right types of people for the company. I just hired whoever I thought would either wants to join us and may do the job. HUGE Mistake. This hurt us a lot in the long run and I would argue that it is one of the critical reasons why we couldn’t quite grow the company beyond what it is today. My hiring mistakes cost us a lot not just in terms of growth opportunity but also the morale and excitement of building a bigger company. I have many regrets in this area and wish I could list everything down in this single post. I wouldn’t be able to.

My failures in hiring came down mostly to:

Hiring the wrong type of people. By “Type”, I mean people who are not meant to work at small teams/startups and need a lot more structure and guidance to succeed. They could do ok at a large company but not at startups. They are not necessarily bad but they are bad fit for a startup.
Hiring whoever said Yes especially during early days. Yes, I did that. Don’t do that.

Now, I did have some success as well which has kept us going all these years. Here is what did work in hiring:

Bringing a great CTO on board as soon as I could. I am a technical founder but I knew that I needed a great CTO so I could focus on building the business and working with customers. I was lucky to be able to convince my own brother to join us. He is the best programmer I knew and he helped us build our entire stack from scratch over many years now.
Hiring people I had already worked with before and knew that they would be a good fit. I approached a few people I worked with before and even though this was at a corporate level, I knew these people are good fit for small teams/startups because they were driven and wanted to do something more meaningful. They had already been building stuff on the side. One of my ex-coworkers joined our team and is still with us at this time of this post. He is doing great and is a reliable team member.
People who have already been entrepreneurial to some extent. They may have built a side project already or tried to do something of their own. I found one of our best employees through flippa who was selling his side project and even though we didnt do the deal, we ended up chatting about his future plans. He decided to join us and was one of my best hires.

What’s Next

I cannot do anything else other than being an entrepreneur. I will continue to work on my current business and a couple of smaller projects. However, I am considering an exit in next 2-3 years from the main business and work on something new. Something bigger. But we will see where I end up. Happy New Year 2025.