Posts by Stephanie Sims
Winner’s Circle: Your accountant is not the problem. But the tool they gave you may be.
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…
Read MoreWinner’s Circle: Nobody warns you about what happens after you hit a million
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…
Read MoreThe Winner’s Circle: Successful entrepreneurs know something most people won’t say out loud
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…
Read MoreBootstrap: The one thing you never stop doing
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…
Read MoreBorrow: What debt is actually for
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…
Read MoreBootstrap, Borrow or Bet: Why venture funding is actually a bet
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…
Read MoreRevenue isn’t the solution (anymore)
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…
Read More80 years. Billions of dollars. One wrong assumption.
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…
Read MoreTell me the truth: About access to capital
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…
Read MoreTell me the truth: Funding does not equal success
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…
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