A few years back, a friend of mine opened a coffee shop. Great location, good coffee, genuinely lovely person running it. Eighteen months later, the doors closed. Not because the coffee was bad. Not because she didn’t work hard enough — she worked harder than almost anyone I know. It closed because of a handful … Read more
A friend of mine spent three weekends building a beautiful Shopify store for her candle business, only to realize halfway through that she’d never actually sold a candle online before and had no idea if people would even find her outside of Instagram. Another friend went the opposite direction — listed a few hand-poured mugs … Read more
I’ll never forget the first time a client asked me, “Do I really need to touch my Google Business Profile, or can I just set it up once and forget it?” I laughed, then immediately felt bad, because I used to think the exact same thing. I set one up for my own side project … Read more
A few years back, a friend of mine — let’s call her Dana, because she’d probably kill me if I used her real name — needed $15,000 to keep her catering business afloat after a slow winter. Her credit score was sitting somewhere in the low 500s thanks to a divorce, a repossessed car, and … Read more
I still remember the exact moment I realized paid ads weren’t going to save me. I’d just launched a tiny SaaS tool, put $200 into Facebook ads because that’s “what you’re supposed to do,” and watched it disappear in three days with exactly one signup. One. And they didn’t even convert to a paying customer. … Read more
A few years back, a friend of mine texted me at 11pm, panicking. She’d just landed her first freelance client big enough to require a 1099, and the client’s accounting department wanted her EIN. “What’s an EIN?” she wrote. “Do I have to pay someone for this? Is this a scam?” I get some version … Read more
If you’ve spent any time in small business Facebook groups or subreddits, you’ve seen the debate. Someone posts “just started my LLC!” and within minutes there’s a reply going “wait, why didn’t you form in Delaware/Wyoming?” followed by three more people arguing about it like it’s a religious matter. I get why the confusion happens. … Read more
A friend of mine spent three weeks building a spreadsheet before she ever registered her business. Not because she loved spreadsheets — because every article she read gave her a different number. One site said $500. Another said $30,000. A third scared her with a $175,000 figure and a lot of talk about “runway.” They … Read more
A few years back, a buddy of mine—let’s call him Dave, because that’s his name and he won’t mind—texted me at 11 p.m. panicking because his accountant had just told him he owed $14,000 more in self-employment tax than he expected. He’d been running his consulting business as a single-member LLC for three years and … Read more
A friend of mine texted me at 11 p.m. last spring: “I think I need an LLC but I have no idea where to even begin. Do I need a lawyer? Is this going to cost a fortune?” She’d just landed her first big freelance design client and suddenly needed to look like a “real … Read more