Planning

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…

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…

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…

SF Series: #5 Which decision will make the most of my limited time and money?

By Stephanie Sims | October 9, 2025

Just tell me the magic formula. THE PROBLEM I’ll just say it – there is no magic formula. There is no single “right answer” for how to build a successful…

SF Series: #4 Does my business model actually work?

By Stephanie Sims | October 2, 2025

THE PROBLEM Your first customer pays you – YES! You look at your bank balance – YIKES! If your customers are paying, why is there more money going out than…

SF Series: #3 When can I stop wearing all the hats & who do I hire first?

By Stephanie Sims | September 25, 2025

THE PROBLEM Founders often build their financial models backwards–and there are two stages to this faulty foundation. THE SOLUTION Instead of letting you say, “Here’s how much revenue I’m going…

SF Series: #2 How long will it take my business to turn a profit & how much will it cost?

By Stephanie Sims | September 18, 2025

HE PROBLEM There’s a lot of noise around doing “all the things” in your business. Everyone’s telling you the best practices for getting clients, for social media, for customer service.…

SF Series: #1 Am I leaving money on the table or losing money on every sale?

By Stephanie Sims | September 11, 2025

THE PROBLEM If each sale isn’t profitable, you can’t “make it up with volume”. You need to know that at some point, you can charge more for your product or…