The Educated Guess

Jordan Guess CPA
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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.

Episodes

  1. AI Agents, Deepfakes & Identity: The Problem CPAs Can't Ignore

    25 FEB

    AI Agents, Deepfakes & Identity: The Problem CPAs Can't Ignore

    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 solution for verifying AI agents and building an audit trail, plus the honest pain points we're seeing with AI adoption inside small CPA firms right now… token costs, context windows, security risks, PII exposure, and model routing. If you're trying to figure out how AI fits into your firm without blowing up your compliance, this one's worth your time. 🔗 FOLLOW JORDAN X: https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ 🛠 PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit 🎙 PODCAST — Bitcoin for Financial Services YouTube: /@bffs_media Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… 📩 NEWSLETTER Weekly insights & updates → https://substack.com/@bffsmedia

    19 min
  2. CPA Firm Survival Kit: How to Thrive in the Age of AI

    20 FEB

    CPA Firm Survival Kit: How to Thrive in the Age of AI

    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 sensitive client data, building a team with a vision people actually want to show up for, and the hire most firms won't make… but should. This isn't optional enrichment. This is survival literacy. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN X: https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast ▶ YouTube: / @bffs_media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… NEWSLETTER BFFS Newsletter — Weekly insights & updates Subscribe: https://substack.com/@bffsmedia

    16 min
  3. I Turned My CPA Firm Into an AI-Powered Machine. Here's How.

    18 FEB

    I Turned My CPA Firm Into an AI-Powered Machine. Here's How.

    $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 repositioning right now before it's too late. 00:00 - Why most people can't think long-term 02:15 - What happened to your purchasing power 07:10 - The $300B software market wipeout 09:30 - How AI is collapsing the workforce 14:20 - The future of business software If you run a CPA firm or any service business and you want to see how we're building an AI-powered operating system on top of a real firm in real time, check out Bitment at bitment.co. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast YouTube: / @bffs_media Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… NEWSLETTER BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia

    32 min
  4. The Death of the Front Porch (And Why We're All Paying For It)

    11 FEB

    The Death of the Front Porch (And Why We're All Paying For It)

    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 air conditioning, TV, and cars moved us inside and to the back. We lost the daily friction that made community possible. Studies show people who eat socially are happier, more trusting, and more engaged. 75% say the best way to connect is sharing a meal. So why don't we do it? My challenge: invite a neighbor over for a meal. Not for a holiday… just a random Tuesday. Even if you disagree on things. Even if it's awkward. Try anyway. Let me know how it goes in the comments. 📚 REFERENCED RESEARCH https://www.hhs.gov/sites/default/files/surgeon-general-social-connection-advisory.pdf ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast ▶ YouTube: / @bffs_media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… NEWSLETTER BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia CHAPTERS: 0:00 - Intro: Front Porch vs Back Porch 0:45 - The Golden Age of Front Porches 1:15 - Three Things That Killed Community 1:45 - The Loneliness Epidemic in America 2:30 - 70% Have Never Eaten With a Neighbor 3:15 - Our Neighborhood Dinner Experience 4:30 - The Driveway Shoveling Story 6:15 - Working Through Misunderstandings 7:30 - Political Differences at the Dinner Table 8:45 - Why Real Conversations Matter 9:30 - The Challenge: Invite Your Neighbor 10:15 - Touch Grass & Build Real Connection

    12 min
  5. A CPA Built This in One Day- No Code, No Agency

    9 FEB

    A CPA Built This in One Day- No Code, No Agency

    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 stuff carefully. If you've ever thought "I'm not technical enough to build things…" this one's for you. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services YouTube: / @bffs_media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… NEWSLETTER BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia

    23 min
  6. Your Team Is Your Strategy (The skill no one teaches you.)

    6 FEB

    Your Team Is Your Strategy (The skill no one teaches you.)

    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. In this video I share what I've learned about spotting the wrong fit, protecting your energy, and making sure incentives are actually aligned before you sign anything. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment: Bitcoin accounting software: https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit BFFS Bitcoin for Financial Services Podcast ▶ YouTube: https://www.youtube.com/@BFFS_Media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGKZS4DUu1kCs?si=6a8fd4c26e7942f2 BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia

    16 min
  7. The New Trump Account Explained: $1,000 Free Money for Your Kids (IRS Notice 2025-10)

    4 FEB

    The New Trump Account Explained: $1,000 Free Money for Your Kids (IRS Notice 2025-10)

    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 Account actually is (and how it works) Who qualifies for the $1,000 government contribution The 5 types of contributions allowed (and the $5,000 annual cap) Investment restrictions (broad US index funds only—no crypto, no individual stocks) The lockup period and when you can access the money What happens when your child turns 18 How employers can contribute up to $2,500/year tax-free Key dates: May 2026 activation, July 4, 2026 first contributions Important deadlines: Form 4547 available in 2026 Account activation info: May 2026 Online portal (trumpaccounts.gov): Mid-2026 First contributions allowed: July 4, 2026 Public comments accepted through: February 20, 2026 This breakdown covers IRS Notice 2025-10 in plain English. Whether you're a parent, grandparent, CPA, or financial professional, this is what you need to know about the Trump Account. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast ▶ YouTube: https://www.youtube.com/@BFFS_Media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGKZS4DUu1kCs?si=6a8fd4c26e7942f2 BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia CHAPTERS 0:00 - Introduction: IRS Notice 2025-10 0:45 - What Is a Trump Account? 2:15 - The $1,000 Pilot Program (Who Qualifies) 4:30 - How to Open an Account 6:20 - The 5 Types of Contributions ($5K Annual Cap) 9:10 - Investment Restrictions (Index Funds Only) 11:45 - Distribution Rules & The Lockup Period 14:20 - What Happens After Age 18 16:30 - Employer Contribution Program ($2,500/Year) 18:45 - Key Dates & Action Items 20:15 - Wrap Up & Resources REFERENCED DOCUMENT: IRS Notice 2025-10: Trump Account Rules #TrumpAccount #IRS #RetirementPlanning #TaxStrategy #FinancialPlanning #ParentingMoney

    11 min
  8. One Client (Your Employer) vs. Multiple Clients: The Real Risk Nobody Talks About

    2 FEB

    One Client (Your Employer) vs. Multiple Clients: The Real Risk Nobody Talks About

    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 isn't needed anymore, your income goes to zero overnight. But when you run your own service business, you have multiple clients. Lose one? You still have revenue coming in from the others. In this episode: The real math behind corporate "security" vs. entrepreneurial "risk" Why one revenue stream is more dangerous than ten What to do in your 20s: job-hopping vs. going all-in on one company How I went from corporate accounting to running multiple businesses The plumber example: breaking away vs. staying comfortable "Pessimists get to be right, but optimists get to be rich" Service business dynamics: employees vs. contractors vs. owners Why you can't see what grows if you never plant the seed This isn't about everyone needing to be an entrepreneur. It's about understanding the actual risks and rewards of each path so you can make an informed decision based on your life stage, responsibilities, and goals. If you've been thinking about making the jump, or you're trying to decide between climbing the corporate ladder or building your own thing, this conversation is for you. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. FOLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast ▶ YouTube: https://www.youtube.com/@BFFS_Media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGKZS4DUu1kCs?si=6a8fd4c26e7942f2 NEWSLETTER BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia CHAPTERS 0:00 - Introduction: The Plumber Conversation 2:15 - Pessimists vs. Optimists 4:30 - One Client vs. Multiple Clients: The Real Risk 7:45 - What to Do in Your 20s 10:20 - My Journey: Corporate to CPA Firm Owner 14:15 - Service Business Math 18:30 - Planting Seeds: How Opportunities Compound 22:45 - When Corporate Makes Sense (And When It Doesn't) 26:10 - Working With the Right People 28:30 - Final Thoughts & Wrap Up #Entrepreneur #CorporateJob #BusinessOwner #CareerAdvice #RiskManagement #ServiceBusiness

    17 min
  9. What College Students Should Consider in 2026: Opportunity Cost vs. Sunk Cost

    1 FEB

    What College Students Should Consider in 2026: Opportunity Cost vs. Sunk Cost

    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: Why opportunity cost matters more than sunk cost for college students What modern employers actually care about (hint: it's not your degree) The college degrees that still make sense vs. the ones that don't How to build real skills that AI can't replace Why getting into the workforce early might be smarter than finishing school The ROI calculation every student and parent should be running This isn't an attack on education. It's a reality check on return on investment. As an employer myself, I can tell you what actually matters when we're hiring—and it's rarely where someone went to school. If you're a student questioning whether to stay in college, a parent trying to give good advice, or a recent grad trying to figure out the smartest path forward in this AI-driven economy, this one's for you. ABOUT THIS CHANNEL I help high earners, business owners, and financial professionals understand how money actually works. Tax strategy, system design, modern finance tools, and the big shifts happening in today's climate. Bitcoin shows up when it's the best example, not as the headline every time. F OLLOW JORDAN GUESS X (Twitter): https://x.com/jordanguess?s=20 LinkedIn: https://www.linkedin.com/in/jordan-guess-cpa/ PRODUCTS & PROJECTS Bitment (Bitcoin accounting software): https://bitment.co Bitcoin for Financial Services Summit: https://denver.space/bitcoin_financial_summit PODCAST Bitcoin for Financial Services Podcast ▶ YouTube: / @bffs_media ▶ Spotify: https://open.spotify.com/show/5ZquhUW0zEGK… NEWSLETTER BFFS Newsletter - Weekly insights & updates Subscribe: https://substack.com/@bffsmedia CHAPTERS 0:00 - Introduction 0:45 - The College Student Conversation 2:30 - Opportunity Cost vs. Sunk Cost 5:15 - What Employers Actually Look For 8:20 - Degrees That Still Matter vs. Ones That Don't 11:40 - How to Build Real Skills 14:25 - Making the Decision: Stay or Leave? 17:10 - Wrap Up #College #CareerAdvice #AI #OpportunityCost #Education #Students

    9 min
  10. AI in Accounting: Why Most Firms Get It Wrong (And What to Do Instead)

    30 JAN

    AI in Accounting: Why Most Firms Get It Wrong (And What to Do Instead)

    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.

    31 min
  • 10 Episodes

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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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