Selling My First Startup:

the story of working on something for 14 months and selling it in 4 days

- Nov 2023 - the beginning

Early Products of the Company

I met my co-founder Daniel at a Toronto local AI event. We briefly chatted and exchanged contact info, but didn't talk too much, since back then I was working with a different team on a different idea.I had no idea this would turn into something wild. Funny how life is sometimes.

About a month after that event, he reached out. Their CTO at the time could not commit to quitting to work on their startup full time, and that was a deal breaker. Coincidentally, I also just left my last team due to timezone and personality issues, and I was just about to look for something new. It was a 2 person team at the time - Daniel was leading operations, and Max was leading sales. They were looking for a tech guy. After we met up, Max showed me his fully booked sales calendar. “This could be a big opportunity," he said, " a lot of people are interested."

"why not, ill give this a try" I thought, not knowing the 1 year rollercoaster ride that follows.

- Jan to June 2024 - getting traction and growing fast

The team was small but complete - Max was working sales, I was doing software, and Daniel managing operations/everything else.

We started selling aggressively to sales teams that needed custom research and personalization, and they don't really care about using a complete product - they just want to book meetings. So we started off building simple tools to automate the obvious parts of the workflow, and hired VAs to manually do the rest. We were running the business as a sales agency - a “tech enabled” sales agency.

This fits well with us being bootstrapped and our team comp - we couldn't afford to wait for months before getting the product ready to start selling. Also, since the majority of the team is non-technical, a tech-enabled service agency makes sense for us to start with so everyone has stuff to do. Our thesis is that we would take any customer and their workflow, do it manually first, and eventually automate everything with tech.

This method worked really well - we were profitable from the get go, and didn't really need any outside capital to sustain ourselves. Our MRR grew really fast in the initial couple of months, partly thanks to our aggressive sales tactics, partly thanks to the AI hype. We hired interns, added more cold callers, things are looking great. We were living the dream, everyday is constant winning, nothing could go wrong.

Until -

- July to Sep 2024 - Churn, the Dip, and the blow up

Sweet Sweet Churn

They say there's always many dips in the entrepreneur journey, and ours came around month 6.

We started to get customer churns, due to us over-promising and under delivering. We had it coming though - we wouldn't say no to customers wanting to give us money, even though we knew we would do a subpar job for them. On top of that, there are a lot of factors we can't control, such as the macro environment, the customers' products, and their offers. If a failing sales organization comes to us for help due to having a bad product - there is inherently nothing we can do. We can only do so much.

Perhaps worse from the actual financial churn is our emotional distress. As we started to see our MRR decline, the emotions started to kick in. At this point we have been grinding for half a year, and we were winning every step of the way. And now, it is the time for us to be tested.

We started arguing, we needed more product features for retention, we needed better customer service, we needed more and more and more… The stress is getting us. Morale is low and we didn't really develop good mechanisms or skills to deal with this type of stress. Soon we would get into hours long calls every other day just to argue and have bad fights.

The funny thing is - by all popular metrics, we are still doing VERY WELL. We are default alive, profitable, and operating with good margins. But of course, that's rarely what kills start ups. In the end, we felt like something had to change. Max ended up leaving the team to join another start up, leaving me and Daniel left to run the show.

Things got slightly better after this. There was less fighting going on, but churn is still a real and pressing problem. We made some big changes to our product, and are still fighting hard to grow.

Then, the second dip hit.

- Oct to Dec 2024 - the burnout

For people that never experience burnout, the description probably seems impossible to resonate or even understand. The idea of intense physical pain from pushing yourself too hard, and sometimes even entire body shut downs, all completely from the mental stress. I definitely thought this was an exaggeration, until I had my first burnout.

Around October, a month after Max left, we were going about as usual, taking customer calls, making product improvements. Then suddenly, the burnout came. I had a massive panic attack, I felt like I was dying, my chest was tight, and I could have a heart attack at any moment. I could barely work for weeks. Every time I opened my laptop, I would have this haunting chest pain, I would be out of breath.

It was my first burnout, and it was scary in a lovecraftian way. I never experienced anything like it - the intense pain caused by something completely psychological. There were a lot of logical reasons for this burnout - we were probably stretching ourselves way too thin after our third cofounder left, taking on 1.5x the workload on top of an already busy schedule that we've had. It's my body's way of fighting back. Logic aside, I felt defeated. I genuinely did not know how to deal with this type of response from my body.

Luckily, I had a Japan trip planned right after I had my burnout. I took some time to completely disconnect for a few days. It helped a lot - but still didn't completely address the burnout though.

Coming back from Japan, my burnout got a lot better, but the business problems still didn't go away - customer churn, product breaking, the emotional stress of things, not to mention at this time we are starting to dig into our personal savings for holiday expenses. We still need to live our lives, relationships and families to work on. Emotions kept racking up.

We took the entire December to think about what we wanted to do, and eventually decided to look for an exit

- Jan 2025 - the exit

The deal, from start to finish, probably took 4 days.

We started to reach out to a couple of companies in January that are working on similar things to us, just to get some conversations started. Certainly we didn't expect any sort of outcome any time soon. Among those companies was a company that just came out of stealth, building something similar to what we were building .

It was a Friday morning. My CEO Daniel took what was supposedly a 30 min quick call with the other co's CEO to do some product demos and to "exchange ideas". Somehow that call turned into a few more texts and calls, and we were having dinner with their chief of staff who just happened to also be in Toronto that same night. We shared plans about our ideas for the product if we had more resources, and a lot of dots were connecting for us.

We ended up talking with the entire exec on the following Monday, and started to work out a deal on Tuesday. Without counting the 2 day weekend, it took us about 4 days to finalize everything from intro to finish.

I'm sitting here writing this post, having just signed my papers. To be honest, I'm still a little winded by how fast things moved. This is one of the moments where the beauty of running a startup really hits for me, and why I love startups. Things can happen really, REALLY fast. One week you are still a bootstrapped b2b SaaS founder, and another week you are getting acquired and ready to go back to working for a boss.

So that's it. my first startup experience. the entire ups and downs. The ecstasy of rapid growth, the anguish when churn kicks in, and the burnout so bad it can only be described as mental illness.