Today, I met with “Sam,” an up-and-coming entrepreneur who’s been working for a few years to grow his bootstrapped start-up. He’s smart, scrappy, and an overall good person. Unfortunately, he hasn’t yet gained the traction he envisioned. I was asked to chat with him by someone who cares deeply about his success.

I started by learning more about the business model, his vision for the company, how his technology works, and how the business is doing. I was able to identify these concerns:‍

• Solo Founder - There is no cofounder or team member at his level intellectually
• Multiple Hats - He’s the GM, senior developer, HR lead, customer service lead, etc.
• Alignment - He spends most of his time executing and managing operations.
• Deadlines - He has no timeline in place.

Sam is caught on the entrepreneur’s hamster wheel. A lack of capital prevents him from hiring the talent or acquiring the resources he needs to execute on his vision. He’s down in the weeds and every day looks the same. I can see this because I bootstrapped CCAW and I was on that hamster wheel too before I turned the corner with the help of others.

I was very open and honest with Sam. I was respectful of what he’d built, but I didn’t sugarcoat the situation. Things must change or his vision will never become reality. I shared my perspective based on my own experiences and encouraged him to seek the perspective of other entrepreneurs as well. I have no doubt that Sam will go on to do great things and I’m excited about what the future has in store for him.

Takeaways:

• ‍Destination. Take the time to define, in writing, where you want your company to go (revenue, number of customers, etc.). This can be simple, high-level, and change over time, but the exercise is priceless.‍
• Timelines - Set target dates for your destination and associated intermediate goals. These dates may change, but that’s OK.‍
• Accountability - Share your destination and timeline with people you respect so they can support you by holding you accountable.‍
• Alignment - Every day, ask yourself, “Does this activity move me closer to my destination?” If the answer is no, think twice about what you’re doing.‍
• Wisdom - Novice entrepreneurs (regardless of age) have a wisdom gap. Fill your gap by seeking out credible entrepreneurs with the experience you lack. If you’re an entrepreneur with wisdom (successful or not), consider giving back. It could change the trajectory of someone’s life!

Have you been on a hamster wheel (entrepreneurial or not)? How did you manage to get off?