Doing it again: A founder’s 2nd startup journey, after being acquired.

Why would someone choose to be a founder? More to the point… after doing it once, why would one subject oneself to doing it all over again?

Why choose to put such immense pressure on oneself repetitively? Is it for wealth? Power? Validation? Or, is it to make a real difference??

Many articles have been written about what drives a founder to success, or to fail. It occurs to me, after having built a successful profitable startup and exited it, that the unchanging fact is that courage is an unwavering requirement.

Are you ready to pay your employees before yourself and be willing to go without a paycheck for a few weeks, a few months, or even a year or two while you are building something you believe in? If so, read on.

When I began building my first company, JHill’s Staffing Services, in 2010, it was at the peak of the great recession. I remember my parents and friends tried to dissuade me from leaving a cushy 6-figure a year job to build something new.

Never could I have imagined that a short eight years later, I would sell my first company to a subsidiary of Marcum LLP, one of the United States’ largest accounting firms.

Selling my business just wasn’t a factor for me while I was building. My laser focus was to deliver substantial value to employers, job-seekers, and my own employees (I bootstrapped all the way). To do that I had to keep the company afloat and drive customer satisfaction and scale bottom-line profitability.

Then suddenly, out of the blue, a CEO at a subsidiary of Marcum LLP messaged me on LinkedIn: “We want to buy your business.”

It sounds like a fairy-tale, right?

It certainly started off that way. After staying on for two years to ensure the company’s continued growth and profitability, I was given the greatest gift: I was offered the opportunity to consult remotely for two years for my old company while my Executive Vice President took over and ran the company.

This happened in November 2019, right before the pandemic.

I will always look at that time as one of the greatest miracles I ever received. Kudos to our EVP who not only kept the company profitable during the pandemic but caused them to become even more profitable in the years after I left.

I remember wanting to negotiate more money for the first few months after I left expecting to be bogged down with work. Gratefully, our team was so self-sufficient that they barely needed me. It felt like both a blessing and a curse to have built a company that was so self-sustaining it no longer needed me.

Around October 2020, while ambling through the streets of Paris enjoying my sabbatical and hosting the occasional TV show with Deepak Chopra or other thought leaders, I came to know a YouTube influencer named, Moon Cho. She invited me to collaborate on a new project in the health and wellness space called Om Heals. Moon wanted to match holistic practitioners with users around the world.

I was instantly hooked.

Thus began my foray into something I had never done before: building a tech startup. We brought in my business coach, Julien Adler, who helped me sell my prior company. We set upon creating a “matching algorithm” based on the core intuition I had developed from over years of matching employers with employees that rarely left.?

Never in a million years did I ever think I would create an algorithm. I barely knew what one was. Nevertheless, since I have always loved numbers, research and data, the endeavor was perfectly suited to me.

In early 2022, we began beta-testing the algorithm, and the results we tremendous.

The Optimal Match engine (our algo) achieved an 89% success rate of matching users with practitioners via our https://www.om-heals.com/holistic practitioner marketplace platform.?

We were stunned! It worked. Our thesis that the average person can only stand so much variability from themselves turned out to be correct.

After about 6 months in beta, my world was rocked. My co-founder, Moon, shared she had to step away from the business for personal reasons. In some ways, I was not surprised as when we met, she already had a thriving YouTube business with over 250,000 organic subscribers. It was too much for her to do both. We parted in the most loving and kind way in July of 2022, and remain friends.

Shortly thereafter, I had my first opportunity to do my first VC pitch. Our original intention was to turn the Om Heals platform into an app. I was on a mission to raise $1M in seed funding. The first guy I pitched, Charlie O'Donnell in New York, changed the trajectory of the company and my personal path. (Thank you, Charlie!)?

When I told him about the holistic medicine marketplace we created and the success we had experienced with the algorithm he replied “I could care less about investing in an energy medicine marketplace, though can your algorithm find me more compassionate dentists? I always find I am traumatized by terrible dentists.”

“Why, yes! We can do that and much more.”

Through amazing serendipity, as I said this, another founder I was mentoring, was silently listening in on the call. I had been mentoring him on his start-up for just under a year. He private messaged me on Zoom right after my pitch, “Jen - I can help you! This is what my company does and I would love to help you develop the algorithm into a SaaS product.”

Shortly after, we were off to the races, and we are excited to share that on January 12th, 2023 our Optimal Match algorithm, which is a SaaS solution, will be available to businesses to use.

It has been an arduous journey getting here, and yet, I fully realize that we’re still at the very beginning of the journey as we just started fundraising for Optimal Match’s seed financing round of capital.

There are some days when I want to curl up in bed and give up.?

I would often find my mind screaming at me: “Running a tech company? Me? I cannot do that. It is too hard! No one has ever done anything like what we are doing. How will I find the right investors? How can we grow this to a $1BN unicorn? YOU’RE GOING TO FAIL AND LET EVERYONE DOWN.

These questions, self-admonishments, and many others plague me late at night and early in the morning. Sometimes I ask myself “Did I make the right choice to build another company?”?

When I find myself in a bottomless pit of doubt, I remind myself of the tens of thousands of job seekers our last company helped, and will continue to help for a long time to come. It is then I know, without a shadow of a doubt, that I have my work cut out for me… but that it’s also possible and necessary.?

It is my absolute belief that matching teachers, therapists, coaches, dentists, and others with the right students, patients, mentees, and so on, is going to help hundreds of millions of people around the world.

I feel it in my bones and I am assured of the good this company will do.

So, why would someone choose to be a founder the first time, let alone again? Why would someone choose the heartache, the pain, the roller coaster ride??

Because you know the good you can do, and that you are the only one to do it. The buck stops with YOU.

To all of the innovators, disrupters, and those out there who get up every day to make their mark in this world, no matter how they “feel” that morning: kudos to you.

Kudos to you for your courage, your perseverance, and your tenacity. Your willingness to go left when everyone else goes right. To stand upright, where others lay down. May we all have the courage to stay the course and realize our purpose.

#startups #advice #entrepreneurship #courage #leadership