How Working Full-Time Helped Me Build a Successful Start-Up on the Side

People said I was crazy to start a business while working full-time. But less than 3 years later, I’m leaving my job to grow Wisepops full time. I can’t wait.

This post is part of a series about my journey as an entrepreneur.

After five years as the co-founder of the ecommerce company GreenRepublic, it was time for a change.
I’d had a few projects running around my head, but with two kids and a newborn, both time and money were tight. As it turns out, that pressure was exactly what I needed.
I wanted to build another business, but a simpler one this time.

I wanted to create an international company that would be quickly profitable. One that would solve a problem without needing me to do constant sales outreach, where customers would find me instead of the other way around. I wanted a business that would scale. And—most importantly—a business that wouldn’t require investors or funding.

I started looking into start-up accelerators, particular Y Combinator, to see the companies they were backing. (Pro tip: Y Combinator is an amazing source of inspiration). That’s when I stumbled across smore, an SaaS business helping customers build beautiful flyers in business. It was simpler and cooler than any SaaS I’d seen before. I immediately fell in love.

Thinking back on my days at GreenRepublic, I remembered how successful pop-ups had been for increasing sales.
“Smore for pop-ups would be awesome,” I told myself.

And thus, Wisepops was born. (Thanks @Smore!)

Six months later—even further convinced by the opportunity and unexploited potential—I found a dev team, defined the beta version specs and incorporated the company.
But there was still the financial pressure of not only building a business, but supporting a family, so I started sending out resumes and talking to headhunters.

Entrepreneur vs. Employee

After a series of interviews, I received a job offer from one of the world’s largest ecommerce companies. Despite my big dreams for Wisepops, I accepted.

Friends thought I was crazy. Apparently, this path was “unrealistic” if I wanted to build Wisepops successful.
“Honestly, you should put this project on hold,” they said.
“You’ll probably love working at this company and should consider a long-term career there.”

Their “advice” just increased my focus.
I took the offer for three reasons:

  1. It would take time to grow Wisepops to a point of profitability,
  2. I didn’t want to go through X months with no income, and
  3. This company had been a huge source inspiration to me. What better way to learn than getting inside such a fascinating company?

This was the beginning of a long road for Wisepops.

Entrepreneur AND Employee

Turns out, there were a lot of pros to starting a business while working at a big company.
I was rarely distracted by what the company needed immediately to stay afloat. This financial security made it easier to make smart decisions while keeping my focus on the long-term.

Plus, working in a demanding environment forced me to obsess about how I structured my day.  I had zero spare time, so I had to be incredibly focused and efficient to get everything done.
But, of course, there were cons.

My job required every employee to give 150%. I’m not going to lie, it was hard to do my job at that level while secretly knowing it would never be my priority.
Having a day job also prevented me from being as responsive to Wisepops customers or setting up meetings with prospects. Growth could have been faster had I been able to work on Wisepops all day.

Then there were the social frustrations of being an employee with a side business. All I wanted to talk about was Wisepops, but because I was working at Big Company—and everyone around me identified as an employee—I couldn’t connect with people about being an entrepreneur.

Moving to Full-Time CEO

Finally, after three years of balancing full-time work with building Wisepops, I’m making Wisepops my full-time priority.
This is the most exciting project of my life. I’m finally able to focus on doing what I love. And Wisepops is now big enough to let me. Now I can:

  1. Give it my full attention without the financial pressure.
  2. Innovative—great things are coming!
  3. Organize my time the way I want it.

I couldn’t ask for more!

So, would I do this again?

Definitely. I learned so much working for such a large company. It helped me finance and grow my own start-up while preparing for the future. Plus, I met some amazing people along the way, many of whom have become great friends.

But most importantly, when you compare my experience with other startup founders who raised money, my situation today would be totally different. I wouldn’t have 100% control over Wisepops and I still wouldn’t be free. I would have raised funds solely due to financial constraint, as opposed to an actual need to scale.

My day job was my investor—trading money for time instead of shares. I couldn’t be more grateful.
Let’s see how it goes. My first day as Wisepops CEO starts today 🙂

Benjamin Cahen Experienced entrepreneur, Ex-Amazon, Ex-VC, Ben is founder & CEO at Wisepops.

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