Tax Tech Simplified: how to run the firm you want using tech to actually help you along the way

You watch one video about how somebody automated their entire firm, and you spend the rest of the day quietly convinced you are going out of business.

Brad Wooten has been running Wooten CPA in Orlando since 2019. Going into year eight he does roughly 350 individual returns and 50 business returns with one other preparer, he averages 42 hours a week in tax season, and he will tell you on the record that you could run a profitable tax firm today with almost none of the software you think you are missing. Then he walks through what he actually uses, what he built himself, and what he still has not gotten around to.

In this episode, you'll discover:

- The five things Brad would set up if he opened a firm tomorrow, and the ones he says to ignore until you have felt the pain yourself

- Why he built his own Claude projects for review, reasonable comp, and tax strategy instead of paying for the products that do it, plus the one question that tells you which way to go

- The Google Doc habit he keeps open all year that turns September into the month next tax season gets fixed

Press play before the October 15 deadline eats the rest of your year. The stretch between now and January is the only one where you can actually fix what drove you crazy last season, and it closes quietly.

Want help simplifying your own firm's tech? Go to y10taxtech.com.

Tax Tech Simplified: How to run the firm you want, using tech that actually helps.

Connect with Brad!

LinkedIn: https://www.linkedin.com/in/brad-wooten-cpa-5a37029/

Firm: https://www.wootencpa.com/

Mentoring and community: https://www.wootencpa.com/mentoring

A client hands you an irrevocable trust and asks what it means for their return. Do you call their attorney, or do you guess?

Jenny Rozelle is the attorney on the other end of that call. She runs a 20 person estate and elder law firm in Indiana, the same firm where she started out answering the phones at the front desk before going to law school at night and eventually buying the place from the founder. She has seen our two professions get this wrong from both sides, and she is direct about what she wishes accountants knew.

In this episode, you'll discover:

- Why "irrevocable" does not mean what most accountants assume it means, and the one assumption that has her re-explaining the same thing to professionals over and over

- How to disagree with a client's attorney without putting the client in the middle, because the client never picks a side, they just stop, and then no plan gets done at all

- What it changes when the attorney on the other end bills flat fees, and why the call you have been avoiding probably costs your client nothing

Press play before the next client walks in with a document you have not seen before. The time to figure out who to call is before you need to call them.

Want help simplifying your own firm's tech? Go to y10taxtech.com.

Tax Tech Simplified: How to run the firm you want, using tech that actually helps.

Connect with Jenny!

Firm: https://www.indianaestateelderlaw.com/

X: https://x.com/jennyrozelle

LinkedIn: https://www.linkedin.com/in/jenniferrozelle/

Her podcast, Legal Tea: https://www.legalteapodcast.com/

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Connect with Yehuda:

X: https://x.com/Y10Tax

LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

https://taxtechsimplified.com/

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Need help with your taxes? https://www.y10tax.com/

You already pay for ChatGPT or Claude. So why would you pay again for an AI tool that just does accounting?

Accounting agents are the third new category of AI tooling to land on us in about a year, after tax research and workflow automation, and they are the messiest of the three, because everybody's version of a set of financials looks different. I spent the past few weeks running them on real client work: rebuilding a year of bookkeeping that was never right to begin with, posting four months of Shopify journal entries from a raw CSV, and reconciling my own card. Some of it saved me hours. Some of it was quietly wrong. This is what I learned in between.

In this episode, you'll discover:

- Why a purpose built accounting agent still beats pointing Claude at your books, and the five reasons that gap exists: security, context, token spend, the environment it lives inside, and the fact that it works on day one instead of after you train it

- The prompt habit that turns a pile of AI output into work you can actually sign off on, including the two columns to ask for every single time so you can trace and check what it did

- Where these tools break right now, and the reconciliation that would have gone out the door 92 cents wrong if I had taken the agent at its word

Press play before you copy last month's journal entry into this month's spreadsheet one more time. Ramp Stack is free through August 31st, so if you want to test any of this on your own books, this is the week to do it.

Want help simplifying your own firm's tech? Go to y10taxtech.com.

I'm also hosting a free roundtable on AI tax prep, Tuesday, October 20th, 12 PM - 1 PM EDT. If you have used any of the AI tax prep tools that came out in the last year or two, or you are just thinking about it, come talk it through with a room of tax pros. Sign up at y10taxtech.com/roundtable.

Tax Tech Simplified: How to run the firm you want, using tech that actually helps.

Mentioned in this episode:

Ramp Stack: https://ramp.com/stack

Become a Ramp accounting partner: https://ramp.com/accounting-partnerships

Intuit Intelligence, inside QuickBooks Online

Whisperflow, for voice to text https://wisprflow.ai/

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Connect with Yehuda:

X: https://x.com/Y10Tax

LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

https://taxtechsimplified.com/

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Need help with your taxes? https://www.y10tax.com/

You set out to fix five problems with a new piece of software, and somehow ended up with six. Sound familiar?

Welcome to the debut of Tax Tech Simplified (formerly The People Behind the Books). In this solo kickoff, Yehuda Tenenbaum, EA, unpacks your firm's "tech stack," every tool that touches your process, and why most firms end up with one they built by accident instead of on purpose. Before you can optimize it, you have to see all of it.

In this episode, you'll discover:

• Why you almost certainly have more software than you think, and the one simple exercise that finally reveals all of it
• The four buckets every tech stack sorts into (marketing, practice management, the "engines" where the work happens, and the supporting tools) so nothing slips through the cracks
• How to dodge "new kitchen syndrome" and stop paying for two tools that do the same job

Press play, then map your own stack before the next tax season hits. The firms that build with intention are the ones that actually run the way their owners want.

🔗 Grab the free tech-stack worksheet (make a copy): https://docs.google.com/spreadsheets/d/19iWkuQsXiBDGnf6RsAMKno4-zLAWAqWfNZLWt9pxqEc/edit

Want help simplifying your own firm's tech? Go to y10taxtech.com.

Tax Tech Simplified: How to run the firm you want, using tech that actually helps.

Want your firm's tech and process set up so you actually have time to market it? Start at y10taxtech.com.

Most firm owners think their marketing isn't working because they aren't spending enough money on ads. Karen Reyburn has spent years proving otherwise.

In this episode, Karen breaks down why audience is the first question and every other marketing question is downstream of it. She explains why "we're friendly and we really care" isn't a differentiator, it's the price of admission. And she makes the case that accountants are already creative, they just don't recognize it when they're doing it.

We also get into the story of the $10,000 hammer tap, why your five-minute answer isn't worth five minutes of money, and the "how might we" question that unlocks better client experiences without a rebrand.

Karen is the author of Accountants, You Are Creative* and founder of The Profitable Firm. Both her books are available in paperback, ebook, and audiobook (narrated by Karen) at karenlreyburn.com.

Ready to stop losing hours to setup and admin? Go to y10taxtech.com.

Ready to reduce the overwhelm and scale your firm? Book your free discovery call at y10taxtech.com.

Every month you rebuild the same reports. You re-export the numbers, rebuild the same workpaper, and then redo the whole thing when one transaction changes after the fact. Most firm owners just accept that grind as part of the job. This episode is about why it does not have to be.

I sat down with Lasse Kalkar, the founder and CEO of LiveFlow, who built an entire company around killing the manual reporting grind for accounting and finance teams. His own path is not what you would expect: from doing soccer tricks as a teenager, to running a coffee shop where he had no idea what his real margins were, to building one of the reporting tools accountants actually love.

In this conversation, you will learn:

• How to give your own firm the same financial clarity you deliver to clients every day, instead of leaving your own numbers a black box
• Why the manual reporting grind is the first thing to systematize away, so your hours go to the advisory work that actually pays
• Why what got your firm from point A to point B will not get it from B to C, and when bringing in outside help is the smarter move than doing it all yourself

If your practice management software and reporting workflows are fighting you, this one is worth your time.

Featured guest: Lasse Kalkar, Founder & CEO of LiveFlow

• LinkedIn: https://www.linkedin.com/in/lassekalkar
• LiveFlow: https://www.liveflow.io/

Erin Pohan, founder of Upkeeping and WAVE-Seattle, shares her journey from a small-town girl in Cleveland to a successful entrepreneur. She discusses her early experiences in accounting, her time living in Japan, and the challenges of balancing work and family life. Erin also delves into the creation of her bookkeeping business and her passion for community engagement through content creation and conferences. She emphasizes the importance of mindset in entrepreneurship and offers valuable advice for aspiring accountants. The conversation concludes with insights into the future of accounting in the age of AI.

Connect with Erin!

https://www.linkedin.com/in/erinpohan/

🤝Connect with Yehuda:
🐦X: https://x.com/Y10Tax
💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

✉️Want to join the show? Send me an email @ [email protected].

http://thepeoplebehindthebooks.com/

00:00 Intro

02:35 Journey into Accounting

11:46 Life in Japan and Career Development

14:03 Transitioning to Philadelphia and Work-Life Balance

24:59 Starting Upkeeping: The Birth of a Business

33:12 Day-to-Day Operations at Upkeeping

39:06 Creating Content and Community Engagement

41:59 Launching Wave Seattle Conference

48:24 Advice for Aspiring Accountants

51:01 The Future of Accounting and AI

54:54 Rapid Fire Questions

Randy Crabtree shares his journey from computer science to becoming a CPA and starting his own firm. He discusses the entrepreneurial spirit that drove him, the challenges he faced in the accounting profession, and the importance of community and mentorship. Randy also highlights impactful client stories and his involvement with the Accounting Cornerstone Foundation, emphasizing the need for empathy and boundaries in the profession. He concludes with advice for aspiring accountants and insights into the future of the accounting industry.

Connect with Randy!

💼 LinkedIn: https://www.linkedin.com/in/randy-crabtree-cpa-1945a67/

🤝Connect with Yehuda:
🐦X: https://x.com/Y10Tax
💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

✉️Want to join the show? Send me an email @ [email protected].

http://thepeoplebehindthebooks.com/

00:00 Introduction and Background

03:38 Career Transition and Entrepreneurial Spirit

06:48 The Journey to Becoming a CPA

09:37 Starting a Firm and Early Challenges

12:37 Lessons Learned from Managing a Firm

15:33 The Shift to a Niche Practice

18:47 Memorable Client Stories and Impact

21:29 Conclusion and Reflections on the Profession

27:36 Founding the Accounting Cornerstone Foundation

29:55 The Role of Conferences in Professional Growth

30:47 First Impressions of Accounting Conferences

33:23 Building Community Through Conferences

35:34 The Unique Role of Accountants

39:28 The Future of the Accounting Profession

41:56 Encouraging the Next Generation of Accountants

44:52 Lightning Round: Quickfire Questions

Have you ever wondered if the “right” accounting path you’re on is actually the best one for you?

Many accountants do everything by the book—climb the ladder, build the firm, serve the clients—only to quietly question whether the way they’re working is sustainable, fulfilling, or even necessary. This episode speaks directly to that moment of tension: when you’re successful on paper, but sense there may be a smarter, healthier, more intentional way to build your career without walking away from the profession you care about.

By listening to this episode, you’ll walk away with:

• A clearer understanding of how to serve clients deeply without letting responsibility consume your life
• Practical insight into why systems, boundaries, and community aren’t “nice-to-haves,” but leverage points for long-term success
• A broader view of what’s actually possible in an accounting career—especially paths most people don’t realize are options

Press play to hear how one accountant’s unconventional choices reshaped her career—and may help you rethink what’s next for yours.

Connect with Rebecca!

🐦 X: https://x.com/RDriscollCPA

💼 LinkedIn: https://www.linkedin.com/in/rebecca-driscoll-cpa/

🌐 http://rdriscollcpa.com/

Checkout The Collaboration Room

🐦 X: https://x.com/tcrtalks

💼 LinkedIn: https://www.linkedin.com/company/tcr-talks

🌐 http://thecollaborationroom.co/

🤝Connect with Yehuda:
🐦X: https://x.com/Y10Tax
💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

✉️Want to join the show? Send me an email @ [email protected].

http://thepeoplebehindthebooks.com/

00:00 Welcome to The People Behind the Books
02:45 Introducing Rebecca Driscoll
02:50 From middle-school teaching to accounting
08:22 Learning bookkeeping the hard way
10:11 Making the leap into tax preparation
13:58 Inside accounting firm culture
17:11 Why technology matters more than most firms realize
19:11 Building a book of business
21:34 How COVID reshaped accounting practices
23:29 The evolution of Rebecca’s firm
25:56 The challenges of being a boss
28:45 Setting and enforcing client boundaries
31:28 Work-life balance and personal growth
33:55 Coaching and helping other accountants
39:33 How the profession perceives its own challenges
41:20 Work-life balance and gender dynamics in accounting
42:51 Advice for new firm owners
43:37 Why community matters in accounting
46:47 The origin of The Collaboration Room
50:38 Building partnerships across differences
54:27 Creating a supportive professional community
57:19 The real value of networking
01:02:02 Personal insights & lightning round

What do Juilliard, IRS audits, and international artists have in common? In this episode of The People Behind the Books, Yehuda sits down with Phyllis Jo Kubey, EA, CFP, to explore her unexpected path from classical music to a 40-year career in tax. Phyllis shares real-world lessons from representing complex clients, navigating audits and collections, advocating confidently with the IRS, and building a long, sustainable career rooted in trust, preparation, and empathy. This conversation offers tax and accounting professionals a rare look at the human side of practice, and what truly makes a difference over the long run.

Connect with Phyllis!

🐦 X: https://x.com/PKubeyEA

💼 LinkedIn: https://www.linkedin.com/in/phyllis-jo-kubey-b04757a/ 

🌐 Instagram: https://www.instagram.com/phyllisjokubey/

🌐 Facebook: https://www.facebook.com/phyllis.kubey.7

🤝Connect with Yehuda:
🐦X: https://x.com/Y10Tax
💼LinkedIn: https://www.linkedin.com/in/yehuda-tenenbaum/

✉️Want to join the show? Send me an email @ [email protected].

http://thepeoplebehindthebooks.com/

00:00 Introduction to Phyllis Jo Kubey
01:07 Phyllis's Journey from Music to Taxes
10:12 Building a Tax Practice in New York
17:12 Navigating Tax Law Changes
20:48 Bridging the Gap Between Creatives and Taxes
23:59 Helping Clients Overcome Tax Challenges
30:45 Success Stories in Tax Resolution
36:56 Navigating Complex Tax Situations
39:03 Client Management and Fee Structures
45:42 Professional Involvement and Networking
51:30 Insights from the IRS Advisory Council
01:01:08 The Future of Tax Professionals
01:05:34 Rapid Fire Questions and Personal Insights