Marketing and business strategy for companies that are good at what they do and hard to find.
The product works. The clients who find them stay. But there’s no reliable way for the right people to find them in the first place. That’s the problem I solve.
Positioning, competitive analysis, website plans, and search and AI-search visibility. Specific enough to act on this week.
See work samples → How I work →
Engagements start with a fixed-fee audit from $4,500, through full strategy work and ongoing advisory. The free two-page read is genuinely free – email claude@1000startups.com.
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The Duck Phillips School of Marketing
Five expensive lessons from Mad Men’s most useful failure – and what his second act says about executive recruiting, then and now
The Man Who Was Right About Almost Everything and Still Lost
Everybody who watches Mad Men wants to be Don Draper. Nobody wants to be Duck Phillips. Which is exactly why Duck is the more useful study – most of us will not spend our careers dazzling clients with a carousel. Most of us are the person in the room with the numbers, the forecast, and the uncomfortable opinion about where the business is heading.
Herman “Duck” Phillips joins Sterling Cooper as Head of Account Services in late 1960, hired by Don himself. He comes over from London, he is a recovering alcoholic, and he is – on nearly every big strategic question – correct. He wants younger copywriters who understand the youth market. He wants the agency to get serious about television. He wants scale, because he can see that independent shops are about to get squeezed. He is right, right, and right. He also loses the client, the merger, the job, the sobriety, and the dog. That gap between being right and being effective is where the actual lessons live. Here are five of them, with the receipts.
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Ask Your Own People First
The one-question audit that takes an afternoon, costs nothing, and predicts your market position better than the deck you paid an agency to build.
Send one email to every person on payroll. No warning. No preamble. No agenda item, no calendar invite, no courtesy heads-up to the department heads. One question:
In one sentence, what does this company do and who is it for?
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The Freddy Rumsen Rules: Six Marketing Lessons from the Most Underrated Man at Sterling Cooper
Six Marketing Lessons from the Most Underrated Man at Sterling Cooper – and What They Reveal About Freelancing Then vs. Now
Everybody quotes Don Draper. Nobody quotes Freddy Rumsen. That is a mistake, and if you sell creative work for a living, it is an expensive one.
Freddy is the guy who gets carried out of a restaurant in the second episode of the series. He is the guy who, in Season 3, drinks himself unconscious in his own office and wets his pants the day before a Samsonite meeting, which ends his twenty-year run at Sterling Cooper. He is also the only major character on that show who actually gets sober, stays sober, and comes back. And when the final season opens, it is not Don who delivers the best pitch in the room. It is Freddy – middle-aged, unemployed by the standards of the day, working as a freelancer – walking into his old shop with a line that sells a wristwatch by refusing to talk about time.
Freddy’s arc is a compressed history of the creative services business: staff job, cushioned by expense accounts and tenure, blown up, rebuilt as independent contract work. Which is to say it is the arc that roughly 72.9 million Americans are living right now (MBO Partners, 2025 State of Independence). Here is what he can teach you.
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Buy the Audience Instead of Building One
Every trade vertical is littered with dead assets that still hold real attention. Nobody bids on them, because they are not businesses, so no broker lists them and no banker calls. This is audience acquisition as ordinary M&A, with a much smaller decimal point.
1. The Whole Industry Is Buying Scratch Tickets
Received wisdom says distribution has to be grown. Publish, post, wait, compound. That is a real strategy, and right now it is a losing one for most people who attempt it.
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