Entrepreneurship
Let me say this carefully and clearly, because I have a lot of friends in accounting, and I mean none of this as a criticism of them. Accounting was not designed to help you run your business. It was designed to track what happened. To make sure the money went into the right buckets. To…
There is a moment that a lot of entrepreneurs talk about. You have crossed some threshold, a million, five million, whatever the number was that used to feel like the finish line, and instead of feeling like you have arrived, you feel more exposed than you did before. The complexity went up. The stakes went…
Hint: There is no “right” answer, there are only better questions. Everyone’s struggling with something. I know that sounds like something a therapist would say. But I mean it as a business observation. The entrepreneurs I see winning right now are not the ones who have banished struggle from their companies. They’re the ones who…
If betting is about asking others to take risks with you, borrowing is about proving you can handle responsibility. There is a reason most borrowing options require at least two years of operating history and positive cash flow. Debt is not about belief. It is about evidence. Core distinction One of the biggest differences between…
The funding fantasy is alive and well. It is February and LinkedIn is already full of celebratory funding announcements. Raised $8 million. Big valuation. Big momentum. 🚀🚀🚀🚀🚀🚀🚀🚀🚀 That story is compelling for a reason. It feels like validation. It feels like winning. It feels like forward motion. But what almost nobody talks about is what…
80 years. Billions of dollars. One wrong assumption. Everyone agrees that small business is the backbone of the country. We’ve been saying it for 80 years. The SBA launched in the 1950s. Programs. Lending initiatives. Tax incentives. Billions in investment. And our business survival rates haven’t budged. 20% of businesses still die in the first…
There’s a pervasive myth in entrepreneurship: raising venture capital is the mark of success. The numbers tell a different story. In 2024, approximately 5.2 million new businesses launched in the U.S. According to PitchBook’s NVCA Venture Monitor, only 5,387 companies closed pre-seed or seed deals (typically the first round of institutional capital). That’s 0.1% of…
There’s a common myth in entrepreneurship: if you get funding, you’re set. It sounds simple. Raise a first round of venture capital, and success will follow. Here’s the reality: investors typically fund less than 1% of the companies that pitch them. Getting funded means you cleared a high bar—but that bar isn’t “this business will…
We’re lying about entrepreneurship. Not intentionally, but the effect is the same. We talk about it as just another career move—changing jobs with slightly higher uncertainty. That’s not what it is. Entrepreneurship is a different risk category entirely. When you take a job, you know what you’re getting paid and when. When you start a…
If you’re asking this, you’re not paranoid. You’re paying attention. You’ve got customers. Money is coming in. But there’s this nagging feeling that you can’t quite shake – are these customers helping you build a solid business, or are you selling yourself short? Here’s what makes this question so hard to answer: early sales only…