My Journey As A Venture-backed Startup Founder: the juggle is real

There are equal parts of my day that bring me a healthy amount of excitement and productivity. Whether it’s time set aside for mindfulness, breakfast time with my girls, date hour with my wife, being elbow deep in executing product designs or my personal ideation retreats. While nothing trumps the clarity my spiritual mindfulness time produces, my ideation retreats always have a way of startin’ something. That’s how I got here in the first place.

In my soul there are etched two complimentary questions that, everyday, resound so loudly in my innermost ear, bringing a halt to my current activity.

“Can this be done differently? If so, will it be better?”

It’s a practice I began while learning to become a more engaged interface designer. Every day at lunch or during a smoke break — I don’t smoke, but figured I could utilize the time my coworkers were accessing as well — I would find an unattended park bench, take a seat, take in a deep breath, lean back and while focusing on a single task, I would let my mind run wild.

It wasn’t always a clean and clear process, but the more I submitted to the it the faster I got at solving my own problems. However, what I didn’t expect is for it took reshape how I view the world around me. Creativity is powerful like that. Ideating to become a more proficient problem-solver had transformed me.

I was no longer just a designer with thoughtful concepts. I had become a solutions architect. I was now an entrepreneur.

It was like having the burden of a super power. I would see a homeless person, and immediately my mind would break into little shards of ideas on how to solve the gross homeless epidemic through social give strategies, crowdsourced housing deployment, etc. Or I’d meet someone who was in between jobs and my mind would begin to build technical solutions for removing the opaque process of interviewing, rate negotiation and the likes. The list goes on and on. It drove my then girlfriend (now my wife) nuts.

But I couldn’t hide from what I had created. So in the summer of 2012, I took the leap to become a full-time founder in my first startup. Being a subject matter expert in omni-channel design and marketing, I decided to launch a boutique marketing agency.

So I built a team

After crossing as many of my t’s & f’s, as well as dotting my i’s & j’s (incorporate.com was my best friend), I set out to build a team.

Thankfully, I’ve played well with others in the past and had garnered a pretty deep network of creative executioners. So I leaned on my buddies, Jose, Bryan, Shane, Asa and Lee to round out my A-team.

  • Jose Cordova, because he produces some of the most beautiful concept photography I’ve ever laid eyes on, so that was a no brainer.
  • Bryan Martinez, because he was renowned in the hip hop community for his high def music video production, so…yeah.
  • Shane Cleghorn, because he literally is the man with the masterplan for all things SEO/SEM, who doesn’t need that.
  • Asa Potter, because aside from being a killer Art Director, any man willing to play dress up and audition for a reality show with a coworker he hardly knows will always have a first class seat on any rocket-ship I build.
  • And, Lee Maxwell, because every creative founder needs a technical scientist to help them measure their ideas and stay grounded in what’s actionable. Plus, he was my roommate, so trying to succeed without him on my team just seemed all kinds of wrong.

The team and I got off to a great start. I dove headlong into my existing network to search for clients we could serve. I have learned that the amount of people you are willing to serve is commensurate to the capacity of what you can earn. And boy did it pay handsomely!

We started out with astronomical growth — increasing our gross monthly revenue month over month for the better part of that first year. It was a dream. It was like purchasing a plot of farm land that already had seeds planted, and all we had to do was harvest what popped out of the ground.

I was pretty stoked. I mean, yes, I’ve always had a strong propensity to believe in myself, but did I expect such a positive client response right out of the gate. Foolishly, maybe. Honestly, I had hoped. Realistically, not a chance.

And just quickly as our relatively meteoric rise began it, just as quickly, began to slow to a snail’s pace. Our sales pipeline was now empty. There were only a few businesses inching down the funnel. And I was officially in over my head. I had failed to scale our sales force to ensure we could maintain our growth path. I was stuck amongst the trees, and completely missed the forrest.

Then I got married

After four months of very intentional dating, and eight months of engagement sorting through how we’d plan to build a successful future together once married, the big day had arrived and gone. It was a world-wind. From moving two apartments into our new home, the week of our wedding; to absentee Wedding Planners; to wrongly assigned tuxedos, our day was one for the ages. And my new bride — though a bit perturbed with the one person hired to keep things organized, and rightfully so — handled it all with beautiful resolve.

Good thing too, cause marrying the founder of a startup put her directly on the front lines of more cluster-bomb filled days like this. [read more in part 2…]

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Jeremy Gaston

Jeremy Gaston

CEO @heytrainr. Fractional CTO. Author.