Back to Basics

January 2017

“What are you gonna do now?" My mom asked.

The question hung in the air as I sat in the hospital room, cradling my newborn daughter Kaya. It was a week after her birth, and I had been staying overnight with her in the intensive care unit so my wife could recover. Born with a chromosome deletion, she had been struggling with feeding difficulties, and the countless trips to and from Yale Children's Hospital were taking a toll. 

I was broke, with no plan and no safety net. And I still wasn’t driving. My once-promising Squarespace business had failed, and I had reconciled myself to the idea of becoming a writer. My plan? To publish this book and go on a speaking tour. 

One day my old Pastor stopped by with a box of diapers.

“Do you miss it?”

“Miss what?”

“Engineering.”

“Oh, I can’t miss it. Being an engineer is a mindset. I’m always solving problems.”

“No I mean the job. Corporate America.”

“Ha. Do I miss it? Do you know how many miserable people would love to escape it, and can’t?”

It was the longest conversation I had had with the man I’d called “dad” half my life.

Even though I’d gone through what felt like the pit - I’d do it again knowing it would equip me with the skills and mindset needed to live the life I imagined.

In the months following Kaya's birth, I tried my hand at various business ventures, desperate to find a way to make ends meet. I ran Facebook ads and set up a Shopify store for a dentist, hoping to tap into the e-commerce market. I even tried my luck at creating a dropshipping store for vaporizers, thinking I could leverage my previous success in the cannabis market.

While these efforts brought in some income, they were far from stable or scalable. I found myself constantly chasing the next opportunity, never quite finding the solid ground I needed to pay the bills much less build a sustainable business. 

The pressure to provide for my growing family wasn’t easing up, and I knew I needed to find a better way.

By March 2017 I had another eviction notice looming. This time I’d have to go to court and stand before a judge.

I remember having a sense of peace that I couldn’t place. I turned my website back on. The next day I got an email from a prospective client looking for a website for the nonprofit he was a part of. He’d found me on the Squarespace specialist directory and was eager to work with me. 

He also made it clear he was looking to spend $5,000 on this website. I didn’t object. The money would tide me over. And the project brought me back to the only thing that had really worked for me.

I decided this time around I’d put everything I’d learned into play - again.

I made a commitment to myself to meticulously document every solution I developed for clients.

I turned each challenge into a blog post or shareable resource, creating a small library of knowledge that I could tap into for future projects. The impact was almost immediate - organic traffic to my site began increasing as people searched for solutions to their Squarespace issues. 

My skills hadn’t changed, but my openness to tackling the challenges that came up had shifted.

I had learned the hard way that hiring the cheapest developers was not a viable long-term solution.

This time I found a guy from the Ukraine who seemed to share my values of transparency, specialization, and a commitment to delivering quality solutions.

I hired him to help clean up some bad code I’d written and he hit it out the park.

This is exactly what I’d needed 3 years ago when I was just getting started!

I got excited again about marketing this service because I could finally fulfill it.

In June 2017, just six months after my daughter was born, I got a message from a client who had a tight budget—$500. They needed some tweaks on their Squarespace site. I ran it by my developer to see if we could make it happen.

A week later, I hit up my developer again. "Hey, quick question—how can I license this code from you? Have you ever done something like that before?"

We had only been working together for a couple of months, so this was new territory for us. But I had an idea. I figured if we could solve this problem for one client, why not others? I started thinking about turning this into a plugin we could sell. The developer wasn’t sure at first—he hadn’t done anything like this before. But I was pretty clear about where I was coming from. 

I told him about my vision of selling plugins that could work within Squarespace’s limitations. Sure, the platform has its constraints, but I knew there was potential. He questioned whether it would even be profitable, but I was confident. I mean, I’ve got a solid marketing background, and I was running a group of nearly a thousand Squarespace users. I knew how to bring in customers, and I was ready to figure out how to deliver on this.

As I waited for his reply, I felt a mix of excitement and nerves. Would he see the potential like I did? Would he be up for this new challenge?