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Early in my career, I represented a small artist management company owned by two guys. Their flagship client was a Florida rock band that had already done everything a band dreams of doing — platinum albums, world tours, songs in movies. The kind of success most musicians never see. My clients were smart. The band was established, successful by all accounts. The question wasn’t how to maintain or recapture a peak. The question was how to extend the ride down the back of the

What That Means for Your Business. When Ashurst and Perkins Coie announced their merger earlier this year, it made news in the legal trade press. Another large firm combination — two global brands, thousands of lawyers, offices on multiple continents. For most entrepreneurs and business owners, it registered as background noise. A big-firm story. Not yours. That assumption deserves a second look. The legal market has been reorganizing for several years. The Ashurst-Perkins Co

She Wanted Someone Who Was Already Thinking. I have a client I've worked with for the better part of two decades. She built a consumer business from nothing — the kind of business that lives or dies on relationships, on repeat customers, on a brand that people feel something about. She is exceptionally good at what she does. Sharp, decisive, deeply attuned to her market. In all the years I've known her, she has changed accountants four times. The complaint is always a variati

Every entrepreneur makes the same leap. Almost nobody talks about what it actually costs. Life, at least life in America, has become almost incomprehensibly complex. The decisions available to us at any given moment — about careers, about money, about where to live and how to work and who to trust with our businesses — are too numerous and too consequential to evaluate from first principles every time. So we don't. We rely on systems that were built, mostly by others, mostly

I saw a software advertisement recently that promised to help law firms capture all the time they’re losing to quick emails and phone calls — the .1s and .2s that slip through the cracks and never make it onto an invoice. The pitch was efficient, confident, and completely self-unaware. Because that advertisement isn’t solving a problem. It’s revealing one. You’ve seen those line items on an invoice. A .1 here. A .2 there. A two-minute email exchange billed as a discrete event

I was in a meeting once — not figuratively, but literally in the room — watching a group of smart, ambitious people argue about numbers that had stopped meaning what they thought they meant. The company had real vision. The founder had genuine charisma and a concept with genuine blue-ocean potential — the kind of convergence of timing and opportunity that makes people want to be part of something before they fully understand what it is. The people around the table had believe

You know this meeting. Maybe you’ve been in it. Maybe you’ve run it. Someone has a vision — a real one, the kind that makes smart people lean forward. They need help building it. A developer, a designer, a marketing mind, someone who can make the thing real. The conversation goes well. The energy in the room is genuine. And at some point, naturally, almost inevitably, the founder makes the offer: I can’t pay you much right now, but I can give you a piece of this. Equity. Ow

They came in prepared. That’s what made it interesting. Most founders who sit across from me at the beginning of a business relationship have done some thinking. They’ve talked through the vision, divided up the roles, and made peace — or something that feels like peace — with how ownership will be split. The more thoughtful ones have gone a step further. They’ve decided who has final say. Fifty-one percent to one partner, forty-nine to the other. Or some version of it. The

Nobody chooses to be in the adjacent lane next to a U-Haul. They just look up and there they are. I was on I-285 this week behind a U-Haul box truck. Not stuck behind it — this one was moving fast. Accelerating aggressively, pushing its way into gaps, cutting people off. Big truck, rented plates, driven by someone who clearly had somewhere to be and no particular concern for the people in his way. It took me about thirty seconds to work out why he could do that, and about ten

I had breakfast with a friend last week — he's also a client, which is how a lot of my best conversations start. We weren't talking business, just catching up, when he mentioned that his wife was planning to list their house next year. Someone had advised them: if you know you're selling in a year, hire a building inspector now. Find the problems. Fix them on your own timeline, not under the gun of a purchase contract when the buyer is already nervous and the deal is already

The best time to find a lawyer is when you don’t need one. Here’s why that’s harder than it sounds — and what it looks like when you get it right. The SEO Argument Early in my career, I worked at a small firm where the founding partners were strong believers in search engine optimization. They wanted the firm to be findable — to show up when someone in Atlanta typed “business attorney” into Google and hit search. I understood the logic. I didn’t share the enthusiasm. My insti

Why entrepreneurs don’t plan for the hardest moments — and what happens when those moments arrive anyway. The Wiring The same qualities that make someone a good entrepreneur make them a bad planner for certain things. Entrepreneurs are wired to project forward optimistically. They are, by nature, positive and risk-tolerant. They have to be. Starting a business requires you to hold a vision of the future that doesn’t exist yet and act on it anyway. Sustaining a business throug

At some point, most business owners arrive at what feels like a simple question: when should I sell my business, and what will I get for it? It feels simple because it sounds like one question. It isn't. It is actually a sequence of questions — each one dependent on the answers before it — and most founders don't know the sequence exists until they're already in the middle of it, talking to someone who only knows how to answer one of them. I have sat across from a lot of foun

Imagine you've heard about a great new club. The kind of place you've been wanting to check out. You ask around — nobody knows exactly where it is or how to get there. Then a rideshare pulls up. The driver says he knows the place. He can take you there. But there are conditions: he can't tell you how long the trip will take, he can't guarantee he'll actually get you there, and he can't tell you what it will cost. What he can tell you is that his meter runs the whole time, reg

I have a client I've known since 2003. I'll call him Gary. When I met him, he was selling payroll services and had an idea — a concept in the HR technology space that he believed in enough to spend years trying to build. We worked on business plans together, laid groundwork, had the kinds of conversations that go nowhere for a while before they go somewhere. At one point, Gary connected with an insurance agency in Florida that operated in the employment space. He told them ab

I have a client in the staffing business — I'll call him Frank — who I first represented back in 2001. We worked together for several years, then lost touch when he sold his company and I changed firms. In 2018, he found me on LinkedIn and reached out. He was back in the staffing business — same industry, same geography, same model — and he had brought in a young guy to help run operations. The young man was smart, motivated, and eager to prove himself. He had no background i