HH #28: Lessons from a $10,000 Gamble

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Welcome to our latest newsletter! Six years ago, I was eager to try new services and expand our business. One particular opportunity presented itself when the town of Stamford, where we are based, was considering no longer picking up loose leaves unless they were bagged. Historically, residents could pile their loose leaves at the curb, and the town would clean them up. However, many surrounding towns required bagging, which was both time-consuming and frustrating for property owners.

With this in mind, I saw a potential gap in the market. With our existing fleet of trucks, all we needed was a leaf-sucking machine and a small trailer to offer leaf removal services. I believed this new service could easily tap into our existing customer base, along with some light advertising. So, we moved forward, purchasing a $7,500 Billygoat leaf-sucking machine and a $2,000 trailer. We even hired a handyman to secure the equipment on the trailer and experimented with various ways to dump the leaves into the back of a dumpster. We were ready to dominate this market.

As fall approached, we were prepared for the leaves to start dropping and the money to start rolling in. However, shortly after the town passed the bill, residents of Stamford reacted with outrage, leading to the town reversing the decision and continuing to pick up loose leaves. Now, I was stuck with a $10,000 investment and no market.

The Lesson in Entrepreneurship

This experience reinforced a key lesson in small business and entrepreneurship: nothing ever goes exactly as planned. Even with a well-researched business plan, there's always an element of unpredictability in the market. I had predicted that the town’s decision would create a profitable opportunity for us, but I didn’t foresee the backlash from residents or how quickly the mayor would overturn the ruling.

"In the business world, the rearview mirror is always clearer than the windshield." – Warren Buffett

As an entrepreneur, you must always be ready to pivot. After investing in this equipment, I didn’t have the luxury of waiting until next season. The opportunity to use the leaf-sucking machine was limited to the short window when the leaves fell but hadn’t yet biodegraded or frozen in the winter. I immediately pivoted and found a condominium association in Rye, New York, with large oak trees that needed leaf removal services. After an in-person estimate and a good impression, I landed the job, which covered more than half of my initial investment.

By the end of the season, we managed to break even with a few additional jobs. While I didn’t make a profit, I sold the machine two years later for $5,000, recouping most of my initial investment. It wasn’t the home run I hoped for, but I walked away with valuable lessons and the confidence to make better decisions moving forward.

"Success is not final, failure is not fatal: It is the courage to continue that counts." – Winston Churchill

What similar experiences have you faced in your business?

How can you learn from those setbacks to make smarter choices next time?

Key Points:

1. Always be prepared to pivot: In business, things rarely go as planned. Flexibility is key to navigating unforeseen circumstances.

2. Research doesn't guarantee success: No matter how much research you do, market forces can shift unexpectedly. Be ready for the unknown.

3. Maximize short windows of opportunity: Sometimes you only get one shot. When opportunities present themselves, act fast and decisively.

4. Turn losses into lessons: Even if things don’t turn out as expected, there’s always something to learn. These lessons will guide you in the future.

5. Recoup and recover: Even when a venture doesn’t result in profit, it’s important to focus on minimizing losses and finding ways to recover your investment.

This story is just one example of how entrepreneurship requires resilience, flexibility, and quick thinking. Share your own experience, and let’s continue learning and growing together. L8r g8rs

See you next Sunday!

Justin Hubbard

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