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The Educated Guess

Jordan Guess CPA

CPA and operator breaking down tax strategy, AI implementation, business systems, and the big shifts happening in finance. Real talk for high earners, business owners, and financial professionals.

PublishesDailyEpisodes10Foundeda month ago
Number of ListenersCategories
CareersEntrepreneurshipBusiness

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Latest Episodes

Just got back from the Philippines and landed straight into one of the most important conversations we've had on the Bitment call, how do you actually know who you're talking to anymore? Between deepfakes, AI-generated voices, and autonomous agents h... more

Is your CPA firm sleepwalking into irrelevance?

The accounting profession isn't dying… but a lot of firms are going to become casualties of the AI wave if they don't get serious right now.

In this episode, I'm breaking down the survival kit every... more

$300 billion erased from software stocks in a single day. AI agents are replacing entire job functions. And if you're still running your business the same way you were two years ago, you're already behind.

In this video I break down exactly what's ... more

70% of Americans have never eaten with a neighbor. The Surgeon General has declared loneliness an epidemic… with effects comparable to smoking 15 cigarettes a day.

This week we had neighbors over for dinner. One of them shared something that stuck... more

I built a full website and a 30-second commercial in one day using AI tools, no design background, no dev team, no agency.

In this episode, I break down exactly how I did it: Figma Make and Claude for the website, Remotion and 11 Labs for the comme... more

A potential client asked me three questions I never get: Are you married? Do you have kids? How long do you want to work? It got me thinking about the skill most people overlook — choosing who you work with.

Teams. Collaborators. Partners. The peo... more

The IRS just released Notice 2025-10 detailing the new Trump Account—a retirement account for kids that comes with $1,000 from the government. If you have a child born between January 1, 2025 and December 31, 2028, you could qualify for this pilot pr... more

Everyone thinks starting your own business is risky. But what if staying corporate is actually riskier?

I was texting with a friend last night—a plumber who's been thinking about breaking away from his employer to start his own thing. The conversa... more

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The Educated Guess launched a month ago and published 10 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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