From Anticipated Failure to Unanticipated Success – 5 Turning Points in My Entrepreneurial Journey


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

While 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 lobby of the Marriott down the street, and constantly putting out fires. Even when many of those problems solved themselves, it felt—for years—like we were always just a few decisions away from possible 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 space, and producing tens of thousands of videos we're really 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 succeed.

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Turning point #1: Getting our first real office

One of the earliest moments was our insurance First real office space.

Stepping into a 2,000 square foot office was both exciting and scary. It was a big financial commitment, but it felt like we finally had a home and were becoming more settled.

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

Plus, we can finally invite clients into our office without them feeling self-conscious about our makeshift setup!

Turning point #2: Getting everyone involved in video content creation

After several years in business, we reached our next defining moment: we decided to focus exclusively on video production.

Up until that point, we had offered a range of services from video to website content to social media management, but this decision to upgrade core competencies it showed that we had a clear mission and purpose.

It was a tough call, especially when it meant giving up 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 to our clients. The move also simplified our marketing message, making it easier to communicate what we did best and stand out in a crowded market.

Milestone #3: Signing our first known enterprise customer

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

This partnership validated our capabilities and opened doors to other major clients. Working with a well-known brand like TripAdvisor for years was a confidence booster and a testament to our quality and reliability. It proved that we could realize big projects and cope with the demands of high profile clients.

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

In 2018, four years into Lemonlight's life, we won our first Inc. Award. 500. That was the moment I finally believed we had a legitimate company. In my mind, only “serious” businesses won Inc. awards, and if we had, 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 customers and partners who wanted to be associated with a successful and award-winning company. This assessment reaffirmed our commitment to excellence and motivated us to aim even higher.

Turning Point #5: Raising our seed round of funding

Our growth initial round of funding it felt like the last milestone in the entrepreneurial 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 bigger opportunities.

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

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

If you're on your entrepreneurial journey, don't forget to celebrate every milestone, learn from every challenge and stay open to game-changing moments. Success often comes when you least expect it, and your next turning point may be just around the corner. Keep pushing forward and embrace the journey!



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