Jordan Guess CPA
The Educated Guess
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.
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Episodes
AI Agents, Deepfakes & Identity: The Problem CPAs Can't Ignore 25.02.2026 19:21
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 handling sensitive work, identity verification is becoming a real problem for financial professionals. We dig into the Nostr protocol as a potential so...
CPA Firm Survival Kit: How to Thrive in the Age of AI 20.02.2026 16:01
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 CPA firm owner needs to not just survive the next 1-2 years, but actually thrive through it. We're talking real AI immersion, secure local LLM setup for...
I Turned My CPA Firm Into an AI-Powered Machine. Here's How. 18.02.2026 32:07
$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 happening to the software market, why the system has been quietly working against you, and how the smartest business owners and CPA firms are reposition...
The Death of the Front Porch (And Why We're All Paying For It) 11.02.2026 12:12
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 with me: "front porch culture vs back porch culture." From the late 1800s to early 1900s, the front porch was America's original social network. Then ai...
A CPA Built This in One Day- No Code, No Agency 09.02.2026 23:28
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 commercial (including training an AI version of my voice). I also talk about the security side- why I wiped my AI agents and how I'm thinking about this stuf...
Your Team Is Your Strategy (The skill no one teaches you.) 06.02.2026 15:39
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 people in your circle. You have more choice than you think. And the quality of those people is irreplaceable. You cannot hack your way around a weak team. I...
The New Trump Account Explained: $1,000 Free Money for Your Kids (IRS Notice 2025-10) 04.02.2026 11:16
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 program. But there are specific rules, contribution limits, investment restrictions, and deadlines you need to know. What you'll learn: What a Trump Acc...
One Client (Your Employer) vs. Multiple Clients: The Real Risk Nobody Talks About 02.02.2026 17:14
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 conversation made me realize something most people get backwards about risk. When you work corporate, you have one client: your employer. If they decide your job...
What College Students Should Consider in 2026: Opportunity Cost vs. Sunk Cost 01.02.2026 9:12
Is college still worth it in 2026? That's the question I had to ask a college student yesterday who's been working with us part-time. The world is changing faster than most people realize. AI is reshaping entire industries. The skills that mattered five years ago are being automated. And yet students are still spending $50K+ per year studying from textbooks written a decade ago. In this episode: W...
AI in Accounting: Why Most Firms Get It Wrong (And What to Do Instead) 30.01.2026 31:10
AI adoption in accounting jumped from 9% to 41% in a single year—but most accountants are still buried in manual work. Why? In this first episode, I break down the real state of AI in accounting firms: what's working, what's failing, and why most AI implementation projects don't deliver results. Plus, the privacy vs. efficiency battle that every firm is facing right now.
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