Anchor Advisors
Anchor Advisors offers small business consulting in the Chicago area. Our advisors help businesses to grow with confidence and make better decisions.
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Latest posts
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Battle scars build trust
I could write this in 25 minutes with an LLM, and I have. But the resulting piece, while technically polished, wasn’t mine. Even when I gave it an anecdote or story to build around, the robot tried hard to make me look good. So I spent 2 hours writing it by hand, letting my…
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I had no authority in the jury room
The judge had instructed us to reach a verdict before we left for the day, and after several hours of deliberation, we were no closer to a resolution. Passionate voices rose on both sides, but each built a narrative from their own stories about what might have happened. In the…
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Two questions to help you get clarity on a hard call
Carl was my client Paul’s right-hand person for years. But during this transition, his behavior was becoming a liability. Nonetheless, Paul defended him out of loyalty. Paul had sold his company to a more corporate entity about a year earlier. The new owners pushed Paul to…
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Win More Business by Being Less Needy
My wife and I bring very different energies to parenting. My wife is an interventionist. If something is wrong, she wants to fix it. If our youngsters had rosy cheeks, she checked their temperature. If they skinned their knees, they needed an antiseptic and a bandage. If they…
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There are no generalized solutions
For the first third of Anchor Advisors’ history, we offered management consulting. We helped founders create the systems and processes that enabled their firms to grow. We worked with over 300 businesses and found 10(ish) problems we solved over and over again. It didn’t take…
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I undersold the Donkey Work
Last week we talked about how AI is coming for your agency’s margin. This week, I’ll offer some ways you might be able to hold onto it, or at least reallocate some of it, to serve you and your clients better. Some of this feedback came from you, the readers, for which I’m…
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How much of what you sell is Donkey Work?
I’ve been thinking about what we’ve learned about AI through mid-2026. Particularly how AI, as it exists right now, will impact professional service firms. The initial hype about “this is the worst version of AI we’ll ever see” and “pretty soon we’ll be curing cancer and solving…
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You win some, you lose some
“You win some, you lose some.” I really hate that phrase. I hate it because losing feels lousy; I want to succeed, perform, and win. At the same time, if my standard is that I have to always win, if I can never have an off day, or misjudge a situation, or stick my foot... The…
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You Can’t Rush a Raspberry
A few years ago I planted 20 raspberry vines. The person who sold them to me told me not to expect berries the first year. They need to root the first year. Fair enough. The second year I did get some berries. My total yield that year was less than a pint from 20 plants!... The…
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How do I make my life better?
Earlier this year, I was fortunate enough to hear Steve Chandler talk live for 3 days. I just can’t stop thinking about one of the stories he told, so I’m sharing it with you. He said: I wrote a play. The only problem with the play is that it only lasts one minute. So it’s not…