From Anticipated Failure to Unforeseen Success — 5 Turning Points in My Entrepreneurial Journey

When my two co-founders and I started a video production company 10 years ago, I honestly didn’t believe we were going to succeed. I had tried to start a few entrepreneurial ventures already, and deep down, I thought this one would end the way the others had. I assumed we’d give it a few months and then be back to applying for jobs.

As we started making money and securing contracts, it still took time for our early successes to feel “real.” Despite our cash flow, we were working out of an apartment, interviewing people in the Marriott lobby down the street and putting out fires constantly. Even when many of those problems worked themselves out, it felt — for years — like we were always just a few decisions away from potentially going out of business.

But against all odds, Lemonlight charted a different path. We’ve hit incredible milestones over the past decade: working with dream clients, breaking sales records, expanding our office space, buying studio spaces and producing tens of thousands of videos we’re truly proud of.

As I reflect on this journey, five key turning points stand out — moments that made me realize we were building something that could actually succeed.

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Turning point #1: Getting our first real office

One of the earliest milestones was securing our first real office space.

Moving into a 2,000-square-foot office was both exhilarating and terrifying. It was a big financial commitment, but it felt like we finally had a home and were becoming more established.

In my eyes, this move symbolized our transition from a scrappy startup working out of an apartment to a legitimate business with a dedicated space to grow. It gave us a sense of permanence and stability, which was crucial for our morale and long-term planning.

Plus, we could finally invite clients to our office without feeling self-conscious about our makeshift setup!

Turning point #2: Going all in on video content creation

A few years into the business, we hit our next crucial milestone: deciding to focus exclusively on video production.

Up until that point, we had been offering a range of services from video to website content to social media management, but this decision to hone in on our core competency showed that we had a clear mission and purpose.

It was a tough call, especially when it meant turning away other potential revenue streams, but it reinforced our identity and helped us build a company around our strengths.

By narrowing our focus, we were able to deepen our expertise, improve our processes and deliver higher-quality results for our clients. This move also simplified our marketing message, making it easier to communicate what we did best and stand out in a crowded market.

Turning point #3: Signing our first well-known enterprise client

The day TripAdvisor found us online and hired us to make their videos was another surreal moment. They were one of our first enterprise clients, and I remember being surprised that they would trust such a small company.

This partnership validated our capabilities and opened doors to other large clients. Working with a renowned brand like TripAdvisor for years was a confidence booster and a testament to our quality and reliability. It proved that we could deliver on big projects and handle the demands of high-profile clients.

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Turning point #4: Winning our first Inc. 500 award

In 2018, four years into Lemonlight’s life, we won our first Inc. 500 award. This was the moment I finally believed we had a legitimate company. In my mind, only “serious” businesses earned Inc. awards, and if we’d earned it, we must have been on the right track.

This recognition was a huge morale booster for our team and a powerful validation of our hard work and growth. It not only increased our visibility in the industry but also attracted new clients and partners who wanted to be associated with a successful, award-winning company. This accolade reaffirmed our commitment to excellence and motivated us to aim even higher.

Turning point #5: Raising our seed round of funding

Raising our seed round of funding felt like the final milestone in the entrepreneurship journey. Finally, someone other than our parents believed in us and wanted to support what we were building.

Securing this investment gave us the financial resources to scale our operations, hire more talent and invest in better equipment and technology. It also gave us the confidence to take bigger risks and pursue larger opportunities.

The external validation signaled that our business had real potential and that we were on a path to sustainable growth.

Related: That ‘Aha’ Moment: How You Know When Your Startup Has Succeeded

Looking back, these pivotal moments were crucial in shaping Lemonlight’s success. In five different ways over 10 years, they provided the confidence, resources and validation we needed to grow from a small startup into a respected company.

If you’re on your own entrepreneurial path, remember to celebrate each milestone, learn from every challenge and stay open to the game-changing moments. Success often comes when you least expect it, and your next big turning point might be just around the corner. Keep pushing forward and embrace the journey!