95% of the Entrepreneurs I Work With Make These 2 Mistakes

After nearly 30 years of working with small business owners, you start noticing patterns.

It doesn’t matter whether someone owns a dental practice, a restaurant, a home services company or an ecommerce business. It doesn’t even matter how smart or talented the entrepreneur is. Certain mistakes show up again and again.

I understand why. Running a business means making dozens of decisions every day. The urgent stuff screams for your attention. New ideas are exciting. Cutting expenses feels responsible. And the latest marketing or technology trend can make you wonder whether you’re falling behind.

Meanwhile, the boring fundamentals that actually drive growth are easy to neglect.

I’ve learned that firsthand. I built PostcardMania from scratch starting in 1998, without investors or outside funding, and I’ve made plenty of mistakes along the way — including one that nearly cost me my company.

After working with 131,201 entrepreneurs, though, two mistakes stand out. I see some version of them in roughly 95% of the small business owners I interact with.

Mistake 1: Underestimating how much marketing you need to grow

Too many entrepreneurs view marketing primarily as an expense to control. I look at it differently: Marketing is the engine that brings customers into your business.

That doesn’t mean spending recklessly. It means knowing your numbers. How much does it cost you to acquire a customer? What is that customer worth over time? Which campaigns consistently generate profitable business?

Once you know those answers, cutting marketing simply because it looks expensive can actually be one of the riskiest things you do.

I learned that during the 2008-09 housing crash and subsequent financial crisis. At the time, 46% of PostcardMania’s clientele was tied to real estate and mortgages. When those industries collapsed, we lost thousands of customers. Revenue dropped, and eventually I began wondering whether we could make payroll.

I refused to lay people off, so advisers suggested cutting our postcard marketing. I reluctantly agreed. It backfired.

Fewer postcards meant fewer leads. Fewer leads meant even less revenue. In 2009, revenue fell 15%. Eventually, I realized that if I wanted revenue to recover, I needed to restore the flow of leads. I brought our marketing budget back to its previous level, and the business recovered.

That experience changed how I think about marketing forever.

So when Covid hit in 2020, and our weekly revenue plunged more than 40%, I did the opposite of 2008: I kept marketing steady. Within five weeks, our weekly revenue had fully recovered and was back above $1 million. Leads rose 9.24% over the next six months without increasing budget. And since then, our revenue has nearly doubled from $60 million annually to nearly $120 million.

Big companies understand that growth requires marketing investment. In August, Kraft Heinz announced they were investing an additional $100 million in its turnaround plan, with most of those funds going toward marketing. The company said it was already seeing stronger performance where those investments were being made.

The lesson for entrepreneurs is simple: If you need more revenue, you need more marketing. Growth requires feeding what works.

Identify your top marketing tactics by measuring revenue and return on investment. From there, ask yourself, “How much more can I responsibly put behind this?”

Mistake 2: Getting too caught up in hacks and trends

Entrepreneurs love a shortcut. I do, too. The problem is when the shortcut becomes the strategy.

A new platform appears. An algorithm changes. AI explodes. A marketing hack goes viral. Suddenly everyone feels like they’re falling behind if they aren’t jumping on the bandwagon. But businesses aren’t usually built through a collection of hacks. They’re built by finding things that work and getting exceptionally good at repeating them.

Chili’s is a useful example. The restaurant chain experimented with flashy technology, including robot servers that quickly expanded to 61 locations. The results were disappointing — just a few months later, Chili’s announced it was pulling the plug on its robot initiative.

Instead, they pivoted to a much less “exciting” strategy: fundamentals.

Over the past two years, Chili’s parent company invested in stronger Wi-Fi, updated payment systems and ordering technology for restaurant staff. Its CIO has said every technology initiative now has to contribute to better food service and guest experience.

Meanwhile, Chili’s stock had risen more than 500% between June 2022 and July 2026, with 20 consecutive quarters of same-store sales growth. Of course, those results reflect a turnaround that isn’t just “ditch the robots,” but the philosophy is worth paying attention to: Fix the fundamentals before betting big on flashy tech.

We’ve taken a similar approach at PostcardMania. I’ve watched countless new marketing channels and technologies arrive over the last 28 years, but I’ve never abandoned a strategy simply because something newer came along. Direct mail has essentially built us up into a $120 million company, and it remains a core part of our marketing today. What we’ve done instead is layer newer tools — digital advertising, tracking, automation and programmatic technology — around what was already proven to work.

And the numbers keep validating that decision. We analyzed 117,857 leads in 2025 — every single direct mail and digital lead generated that year — and discovered that we made $416.04 per direct mail lead and only $38.59 per digital lead, a 978% difference.

That doesn’t mean digital is bad. We invest heavily in digital, too. It means you shouldn’t confuse “new” with “better.” It also means you should figure out how new technology can make proven tactics even stronger.

After nearly three decades in business, I’ve become much less impressed by what’s new and much more interested in what works.

Track your marketing. Invest in what produces profitable customers. Keep improving it. Test new ideas without abandoning proven ones. Those principles aren’t flashy, but they’re the bedrock of success.

After nearly 30 years of working with small business owners, you start noticing patterns.

It doesn’t matter whether someone owns a dental practice, a restaurant, a home services company or an ecommerce business. It doesn’t even matter how smart or talented the entrepreneur is. Certain mistakes show up again and again.

I understand why. Running a business means making dozens of decisions every day. The urgent stuff screams for your attention. New ideas are exciting. Cutting expenses feels responsible. And the latest marketing or technology trend can make you wonder whether you’re falling behind.