I Thought It Was the Worst Day of My Life
In our latest podcast, a new contributor joins the team: Ted Wolf is co-founder of Guidewise, which helps businesses adopt AI. He says the hard part isn't the technology.
Here are today’s highlights:
It was small businesses that stood up to President Trump’s tariffs. They get their day in court Wednesday.
Lamar Tyler recommends using the Pareto Principle to analyze pretty much everything.
Amazon’s shopping assistant, Rufus, is designed to keep consumers within its ecosystem rather than searching on Google or in an AI chatbot.
What have you decided about throwing a holiday party this year? Yes or no? And what are you doing to protect yourself?
THE 21 HATS PODCAST
This week, we welcome Ted Wolf, co-founder of Guidewise, as the newest regular member of the 21 Hats Podcast crew—and Ted arrives with a pretty good story. Back when he was building his IT-staffing business with his brother, a senior employee walked out. But he didn’t walk out alone—he took key employees, key accounts, and 40 percent of the company’s revenue. At the time, Ted thought it was the worst day of his business life. Turns out, he says, it was his best. Because that disaster forced him to rethink everything—how decisions get made, how profits get shared, how responsibility gets distributed. And that shift led not only to healthy growth but eventually to the kind of exit business owners dream about.
That experience continues to inform the work Ted does today, helping companies integrate AI into their operations. The hard part, he tells Jennifer Kerhin, isn’t the technology—it’s the people. It’s managing the change, the fear, the implications.
Of course, technology matters, too. Ted and Jennifer also discuss whether small businesses should try to retrofit AI into their current tech stacks—or whether the smarter move, painful as it may be, is to start fresh.
THE 21 HATS RESOURCE GUIDE
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