What is the worst business mistake you've ever made?

Learn From Our Pain: The Business Mistakes That Almost Destroyed Us

Even the most successful entrepreneurs have a graveyard of mistakes behind them. The difference between those who ultimately succeed and those who don't often comes down to learning from those mistakes—preferably someone else's mistakes rather than your own.

At Starting Block, we believe in transparent, no-nonsense business advice. That's why we're sharing some of our most painful business blunders—so you can avoid these costly errors as you build your own venture.

Video: The Business Mistakes That Almost Destroyed Us

Mistake #1: Partnering for Convenience Instead of Compatibility

As Jacob explains in the video, one of the costliest mistakes entrepreneurs make is choosing business partners for the wrong reasons. Unfortunately, this lesson often comes after the damage is done.

Common partnership mistakes include:

• Partnering with friends simply because you enjoy hanging out together
• Bringing on partners because you can't afford to pay them (offering equity instead)
• Failing to discuss long-term vision, work styles, and expectations
• Not creating proper legal agreements from the beginning

The Better Approach: Treat business partnerships like marriages—because in many ways, they are. Look for complementary skills, aligned values, and compatible communication styles. Ask the difficult questions up front: How will decisions be made? What happens if someone wants out? How will conflicts be resolved?

A good partnership should make both parties stronger than they would be individually. As Jacob notes, "Partner with someone because it feels great for the long haul—like you complement each other and you're going to be a better team than you are as individuals."

Mistake #2: Premature Scaling and Unnecessary Growth

Parker shares a common but rarely discussed entrepreneurial mistake: growing too quickly and for the wrong reasons. In his previous business, he and his partner began scaling up with office space and new hires because they thought that's what successful businesses were supposed to do.

The result? Less flexibility, increased stress, and a business that was less resilient to market changes.

The Better Approach: Be intentional about every aspect of growth. Before expanding, ask:

• Will this truly serve our customers better?
• Will this improve our quality of life as business owners?
• Is this sustainable based on our current and projected revenue?
• Are we doing this because it makes business sense, or because it feeds our ego?

As Parker notes, "Be more intentional about growth and scale. Make sure that's actually what you want to do and that it will actually serve the customer—and that it's not just for your own self-interest."

Mistake #3: The Hidden Costs of "More"

Jacob makes a profound observation in the video: "A lot of times more profit means more responsibility and more management and more work."

This reality contradicts the standard entrepreneurial narrative that bigger is always better. Many business owners find themselves earning more money but enjoying their work less as they scale. They started a business for freedom and passion but end up with a demanding entity that controls their life.

The Better Approach: Define success on your own terms. For some, that means building a lean business that supports a specific lifestyle. For others, it means growing a large organization with many employees. Neither approach is inherently right or wrong, but the choice should be conscious and aligned with your personal values.

Learning From Experience: The Starting Block Approach

These hard-earned lessons form the foundation of our approach at Starting Block. We believe in:

• Starting scrappy and staying lean until you've proven your concept
• Being intentional about every aspect of growth
• Making decisions that serve both your customers and your quality of life
• Learning from others' mistakes to avoid costly missteps

Your Turn: Preventative Medicine

Consider this blog post preventative medicine for your business. By learning from our mistakes, you can avoid the painful (and expensive) process of making them yourself.

As you build your business, periodically ask yourself:

• Am I partnering with the right people for the right reasons?
• Am I growing because it serves the business, or to fulfill some other need?
• Are my business decisions aligned with the life I actually want to live?
• Am I learning from others' experiences, or insisting on making my own mistakes?

The Path Forward

The most successful entrepreneurs aren't those who never make mistakes—they're those who learn quickly, adapt accordingly, and try not to repeat the same errors twice.

By sharing these experiences openly, we hope to save you from at least a few of the painful lessons we've endured on our entrepreneurial journeys.