From Anticipated Failure to Unanticipated Success – 5 Milestones in My Entrepreneurial Journey | entrepreneur

When my co-founder and I started a video production company 10 years ago, I honestly didn’t believe we would succeed. I had already tried to start a few entrepreneurial ventures, and deep down I thought this one would end like the others. I thought we would give it a few months and then go back to applying.

As we began to monetize and secure contracts, it still took time for our early successes to become “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 resolved themselves, it felt—for years—that we were always just a few decisions away from potentially being out of a job.

But against all odds, Lemonlight charted a different path. We’ve hit some incredible milestones over the past decade: working with dream clients, breaking sales records, expanding 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 milestones stand out—moments that made me realize we were building something that could really succeed.

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Milestone #1: Getting our first real office

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

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

In my opinion, this move symbolized our transition from a scrappy startup operating out of an apartment to a legitimate business with dedicated space to grow. This gave us a sense of stability and stability, which was very important for our morale and long-term planning.

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

Milestone #2: Going all-in on video content production

A few years into the business, we reached our next major milestone: the decision to focus exclusively on video production.

Until then, we offered a range of services from video to website content and social media management, but this decision to strengthen our core competency showed that we had a clear mission and purpose.

It was a tough call, especially when it meant bypassing other potential revenue streams, but it strengthened our identity and helped us build a company based on our strengths.

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

Milestone #3: Signing our first 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 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. This proved that we can handle large projects and meet the demands of outstanding clients.

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Milestone #4: Winning the first Inc. award. 500

In 2018, four years into Lemonlight’s life, we received the first Inc. Award. We won our 500. This was the moment I finally believed we had a legitimate company. In my mind, only “serious” businesses won corporate awards, and if we did, we must be on the right track.

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

Milestone #5: Raising our initial funding round

Raising our seed round of funding felt like the last milestone in our 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 showed that our business has real potential and we are on a sustainable growth path.

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 us with the trust, resources, and credibility we needed to grow from a small startup to an established company.

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