The first client I ever coached on how to start a side hustle was a hospital pharmacist named Teresa. She came to our first call with a notebook full of ideas, eleven of them, and a look on her face I have since seen a hundred times. In fact, it’s the look of someone who’s tired of waiting for permission. However, she didn’t need more ideas. Instead, she needed a plan that fit inside a life that already had a 45 hour work week, two kids, and a mortgage. Within six months she was earning a steady four figures a month writing medication guides for small clinics. Still, she didn’t…

I have sat across the desk from a few thousand business owners, and nearly every one of them wanted to know how to get a small business loan without wasting months on the process. Some of them walked out with a loan commitment within a few weeks. Others came back three or four times before we got there. A smaller group never got there at all. What surprised me early in my career is that the difference rarely came down to how good the business was. It usually came down to how well the owner understood what I needed to see. If you want to know how to get a…

Learning how to register a business name is one of the first real tests every new owner faces, and I have spent a good part of my career walking people through it. Typically, they arrive excited, they already ordered a logo, and sometimes they have even printed the shirts. Then we run the searches together, and about one time in four, the room goes quiet. For example, the name is taken by an LLC two counties over, or worse, it belongs to a company that owns a federal trademark and has lawyers who send letters for a living. Fortunately, that moment is avoidable. Knowing how to register a business name…

Every fall, around the time my clients start building next year’s budget, I get the same question in some form: “What should I be paying attention to?” These days that question is really about the small business trends 2027 will bring, and it usually comes right after a long sigh. I understand the sigh. The last few years have asked a lot of small business owners. Costs climbed, customers changed how they buy, and every software vendor on earth started promising that artificial intelligence would fix everything. Most owners I advise don’t want another prediction list. They want to know which shifts will actually show up in their numbers and…

Almost every week, someone sits down in my office with a business idea, a little savings, and the same opening question about llc vs sole proprietorship: “Do I need an LLC, or can I just start?” Usually they have already read four blog posts that contradicted each other. One said an LLC is essential. Another said it is a waste of money. A third said something about taxes that turned out to be wrong. After years of forming companies, unwinding badly structured ones, and occasionally defending owners whose “protection” turned out to be thinner than they believed, I can tell you the honest answer is less dramatic than either camp…

When founders ask me how to write a business plan, I start with something I tell almost everyone who sits across the table from me: nobody is going to grade your plan on how pretty it looks. Instead, they are going to grade it on whether you actually understand your business. That sounds obvious, but in practice it isn’t. Over the years I have read hundreds of plans, and the ones that fall apart usually look impressive on the surface. For example, I have seen forty pages of glossy charts and a mission statement that could belong to any company on earth. Then, when I ask one simple question like…

I have sat across the table from a lot of first-time owners trying to figure out how to start a small business. Some of them walked in with a thick binder and a spreadsheet for every scenario. Others walked in with a napkin sketch and a gut feeling. Here is the funny part: the binder did not always win. The people who made it were usually the ones who asked good questions early, listened to the answers, and kept their costs low while they figured things out. So if you are wondering how to start a small business and you have never done this before, pull up a chair. I…