An Embarrassment of Riches

An Embarrassment of Riches

February 24, 2026

My grandparents grew up as dirt-poor farmers.

When my grandfather came back from World War II, he was determined to do more for his family, so he started his own business.

His first business was a little bar that he later added a restaurant onto.

Next he opened a dry cleaners and a car wash.

Over time, he bought rental properties and even a hauling company.

His entrepreneurship substantively changed the fortunes of my family. My dad and his siblings went to college, as did I and my cousins.

While my grandparents weren't rich they climbed from subsistence farming to solidly middle class.

There's a fun story that goes around my family that when my grandfather started making money, he bought some jewelry for my grandmother.

He even bought her (what he thought was a great present) a Cadillac.

My grandmother would never wear the jewelry out in public and she would never drive the Cadillac during the day because she didn't want her friends and neighbors to think that she'd gotten 'uppity' now that she had a little bit more money.

What I think is important about this story is that it shows that middle class folks are taught to be modest and not to show off their wealth, unlike the millionaires and the billionaires who shove their success into headlines.

I strongly believe we middle class folks should be prouder of the things that we have accomplished.

Just because you haven't built a million-dollar business doesn't mean that what you're doing isn't important.

You're helping people, building connections, and strengthening relationships.

That side gig that you have? If it helps support the family budget, that's important.

If you're daring to start a business and make life better for your kids, that should be celebrated.

I hope that you celebrate yourself and congratulate yourself for all the hard work that you're putting in.

You don't have to be billion-dollar business impacting the global economy, to be a success.

Here's to you, middle class entrepreneurs who are working hard, who are taking chances, who are daring to do something new and brave.

************
​​​​​​​

Whenever you’re ready, there are two ways I can help you:

1. The Winners Circle — join a focused, supportive group of pre-six-figure entrepreneurs navigating building a kickass lifestyle business together. Get monthly networking, problem-solving, accountability, and “what’s working now” sessions, plus direct access to The Success Circle frameworks that have helped thousands get over the six-figure hump. Learn more

2. Private Advisory — work directly with me as your strategic and tactical advisor. For established six-figure+ business owners ready to grow while keeping their freedom and sanity. I work with a select group of entrepreneurs in an advisory capacity to transform their businesses. Apply Now.

Back to Blog