Leadership

Winner’s Circle: Your accountant is not the problem. But the tool they gave you may be.

By Stephanie Sims | March 19, 2026

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…

Winner’s Circle: Nobody warns you about what happens after you hit a million

By Stephanie Sims | March 12, 2026

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…

The Winner’s Circle: Successful entrepreneurs know something most people won’t say out loud

By Stephanie Sims | March 5, 2026

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…

Bootstrap: The one thing you never stop doing

By Stephanie Sims | February 19, 2026

People talk about bootstrap, borrow, and bet as if you pick one and move on. That is not how real businesses work. You always bootstrap. What bootstrapping actually means Bootstrapping…

Revenue isn’t the solution (anymore)

By Stephanie Sims | January 8, 2026

There’s a specific kind of pause I’ve learned to listen for. It usually happens when a business owner tells me that they hit their sales targets – but doesn’t seem…

80 years. Billions of dollars. One wrong assumption.

By Stephanie Sims | December 11, 2025

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…

Tell me the truth: About access to capital

By Stephanie Sims | November 20, 2025

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…

Tell me the truth: Funding does not equal success

By Stephanie Sims | November 13, 2025

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…

Tell me the truth: Entrepreneurship isn’t a career move

By Stephanie Sims | November 6, 2025

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…

Tell me the truth: Is my price right?

By Stephanie Sims | October 30, 2025

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…