Lessons learned from my first $200K as a solopreneur

December 2, 2014


Exactly one year ago, I was struggling with the decision about whether to take my “side business” full-time. I had reached a point where, after three years of after-hours freelancing, I was beginning to out-earn my full-time job. But I was still scared to take the leap; worried that my success was just dumb luck. Long story short, I took the jump, and sometime within the last year, my business hit the $200K revenue mark. This is what I learned along the way:

Lesson #1 – I was capable of more than I thought

In the grand scheme of business, $200k over a span of 3 years isn’t much money. During this time period, I incurred significant expenses, so my take-home profit was decidedly less than my revenue. Many of my friends were running multi-million dollar businesses, and in past roles, I’d managed $200K budgets for single advertising campaigns.

But the milestone wasn’t about the money.

What struck me was that I created a sustainable revenue stream from nothing more than ambition and hustle. In hindsight, I didn’t even have a clear strategy in place. I was throwing metaphorical spaghetti at the wall, and it was sticking. It was a silly approach to generating cash flow. The experience, however, motivated me to set my goals much higher; to build a company that could scale beyond just me. For several months, I struggled to understand what exactly that venture would be, as I had—and still have—so many ideas that inspired me. Someone once gave me great advice: to simply “do what I feel like doing,” as my business idea will likely keep me up at night and consume my life for the next few years, or even longer. I decided that I love teaching people, and in 2015, I would create a business education product to help people feel more inspired and empowered in their careers.

Lesson #2 – I am crazy for trying to do everything myself

As my business started taking off, my sanity started falling through the cracks—mostly because I was trying to do everything on my own. I’m one of those people who take immense pride in figuring things out. But the responsibilities kept piling on, and there weren’t enough hours in the day for me to keep doing everything. When I hit the $200K mark, I realized that I was the roadblock that would prevent my business from scaling. So, I started delegating more. I started building processes with my CPA, relied on my lawyer more for research and information, hired an executive assistant and on-boarded an intern. I’ve been fortunate enough to find an amazing technical co-founder who augments my strengths and complements my weaknesses. While my team is still in its infancy—and the process of delegating is taking much longer than I would like—I feel confident that I am on the right path to making thoughtful decisions about who I bring on to my team.

Lesson #3 – My community is my lifeblood

My co-founder and I are about to embark on a big, intimidating journey. We’ve barely scratched the surface of what we want to create, and I’m already overwhelmed. In a sense, what I’m experiencing now is what I felt when I decided to go freelance a year ago. I looked for jobs almost every day for the first few months, even though my business was growing. Now, I’m not looking for jobs, per se, but I’m looking for every possible excuse not to pursue my aforementioned education company. This is for no other reason than the fact that I’m absolutely terrified. Here are some questions that keep running through my head:

·       What if I spend a bunch of money and end up with a product that flops?

·       Is self-funding the right approach? Should I be seeking angel investment or venture capital to achieve the “big” vision in my head?

·       Is it normal for my co-founder and I to be feeling completely lost?

·       Am I an idealistic idiot?

I’m fighting hard against uncertainty; to not let my fears get the best of me. As one of my friends put it, “I have to be all in.” I’m pushing myself to do exactly that: to close my eyes and jump in again. The more I push myself, and the more scared I become of falling, the more I realize that I’m surrounded by an amazing community of friends and entrepreneurs. I’ve come to understand that they currently are—or have been—just as confused as I am. The biggest lesson that I’ve learned from my peers is that it’s completely alright to not have all the answers.

I’ll land on my feet.

Your thoughts

Are you an experienced entrepreneur? What were some of your first, unexpected milestones, and what did you learn from them? Share your thoughts, reactions, and feedback in the comments section below.

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about the author

FreshBooks is the #1 accounting software in the cloud designed to make billing painless for small businesses and their teams. Today, over 10 million small businesses use FreshBooks to effortlessly send professional looking invoices, organize expenses and track their billable time.