Scaling a CPA firm sounds exciting until you hit the messy middle.

Yuri sits down with Anomaly CPA owners John Malone and Greg O’Brien to talk about what it actually takes to grow from a solo firm into a 40-person, multi-million-dollar operation.

They get into the early decisions that shaped Anomaly, why Greg moved away from the traditional hourly model, how John’s non-accounting background became an advantage, and why the $1M to $2M range can be one of the hardest stages for firm owners.

They also break down hiring ahead of growth, building a marketing engine, qualifying leads, pricing with recurring packages, using AI inside the firm, and why owners eventually have to stop being the hero if they want the team to scale.

If you’re building a firm and trying to decide whether to stay lean or push for something bigger, this conversation gives a real look at the tradeoffs.

Episode Highlights:

0:00 - Why owners become the bottleneck
0:46 - Meet John Malone and Greg O’Brien of Anomaly CPA
3:46 - Starting the firm and moving away from the traditional model
6:01 - Taking on early work without building the wrong firm
8:42 - How John and Greg partnered up
12:10 - Why a non-accountant perspective helped the firm scale
14:18 - Growing to 40 people and $4M+ in revenue
17:17 - The “awkward teenage stage” between $1M and $2M
22:18 - Hiring ahead of growth and protecting payroll
27:17 - Building a digital marketing engine
32:56 - Qualifying leads and filtering out bad-fit prospects
36:26 - Why Anomaly uses monthly packages
39:23 - How the team is implementing AI
40:56 - Tech stack, ClickUp, Drake, and change management
51:08 - What’s next for Anomaly CPA

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH GREG O’BRIEN

LinkedIn: https://www.linkedin.com/in/greg-o-brien-cpa-88a3472b/

Website: https://www.anomalycpa.com/team

CONNECT WITH JOHN MALONE

LinkedIn: https://www.linkedin.com/in/john-malone-019ba827/

Website: https://www.anomalycpa.com/team

Yuri sits down with Mike Mazzanna to talk about the real path from big firm tax work to launching a solo CPA firm.

Mike shares the 109-hour billable week that pushed him toward firm ownership, why flexibility mattered more than simply working fewer hours, and how he built his practice with contracting revenue, LinkedIn relationships, and a clear focus on systems.

They also get into tax software decisions, ProConnect vs. Access, TaxDome workflows, client onboarding pain points, pricing goals, and why connecting with other accountants can be one of the best ways to grow a firm.

Episode Highlights:

0:00 - Introduction
0:56 - Mike Mazzanna joins the show
2:00 - Mike’s background and path into accounting
4:32 - Moving from internal audit into tax
6:25 - The 3 a.m. California return meeting
8:16 - Why Mike wanted to start his own firm
11:45 - Launching with a plan and avoiding bad clients
14:38 - The LinkedIn post that brought early momentum
18:17 - Moving from Drake to ProConnect
20:47 - Why Mike started looking at Access
25:50 - How to think about tax software decisions
29:10 - Mike’s first full tax season as a solo firm owner
31:33 - Practice management, TaxDome, and billing
35:45 - Building workflows before automations
37:07 - AI tools, Juno, and tax season pain points
44:00 - Revenue goals and client retention
45:51 - The value of accounting communities
50:50 - Where to find Mike

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH Mike Mazzanna

LinkedIn: https://www.linkedin.com/in/mike-mazzanna-cpa/

Website: https://www.mazzcpa.com/

AI isn’t coming for tax. It’s already changing how tax professionals research, review, and deliver advice.

Yuri sits down with Benjamin Alarie, tax law professor at the University of Toronto and founder of Blue J, to talk about the future of tax research, why AI became an existential question for him, and what it took to build a tax technology company long before AI became the thing everyone was talking about.

They get into the differences between U.S. and Canadian tax systems, the reality of building a startup from academia, how Blue J raised a $122 million Series D, why culture matters so much in a growing tech company, and how small firms can use AI as a second set of eyes on tax work, advisory opportunities, and client questions.

This is a nerdy tax conversation in the best possible way.

Episode Highlights:

0:00 - Intro
1:04 - Meet Benjamin Alarie
3:12 - How Ben got into tax law
6:18 - U.S. vs. Canadian tax systems
11:49 - Why Ben started Blue J
19:39 - Leaving academia to build a tech company
29:15 - Raising capital and scaling Blue J
32:26 - Building culture in a growing company
43:02 - How Blue J is changing tax research
53:03 - How small firms can use AI in tax work
56:25 - Security, planning, and what’s next for Blue J
1:00:45 - Where to find Ben and Blue J

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH BENJAMIN ALARIE

LinkedIn: https://www.linkedin.com/in/aitaxman/?originalSubdomain=ca

Website: https://www.bluej.com/

This week on The Fun CPA Podcast, Yuri talks with Macgill Davis, co-founder and CEO of Rize, an AI-powered time tracking tool for accounting firms and professional service businesses.

They talk about why time tracking sucks, how AI can remove manual timesheets, and how firm owners can use better time data to understand client profitability, pricing, interruptions, and focus.

Macgill also shares the story of shutting down a previous VC-backed startup, what that taught him about niching down, and how Rize eventually became a “Whoop for your work.”

Episode Highlights:

0:00 - Episode open

1:01 - Meet Macgill Davis, CEO and co-founder of Rize

2:01 - How Rize uses AI to automate time tracking

3:02 - Yuri’s experience using Rize to understand his workweek

7:37 - How Macgill got into the time tracking space

10:00 - Shutting down a VC-backed startup and starting over

12:30 - The biggest lesson: stop building for everyone

14:38 - Testing demand before building the product

16:41 - Who Rize is really built for today

19:02 - Why client-level time data matters for firm profitability

20:30 - How Rize tracks client work without screenshots

23:15 - Tracking task switching, interruptions, and focus

27:11 - Moving from the U.S. to Portugal

29:47 - Life in Lisbon and Portugal’s quality of life

32:41 - Castles, history, and the European lifestyle

36:03 - Wrapping up and where to find Macgill

A SPECIAL FROM RIZE

Discounted rates for the first 3 months with this link: https://rize.io/?via=yuri

Go check out where your time on the computer is being spent

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH Macgill

Website: rize.io

Email: macgill@rize.io

What does it actually look like to build a modern CPA firm without losing yourself in the process?

Yuri sits down with Logan Graf to talk through the real decisions behind firm ownership, from taking the leap into entrepreneurship to figuring out whether buying a firm even makes sense.

They get into pricing, hiring, content creation, social media addiction, and the tension between making more money and actually enjoying your life. They also discuss Logan’s community Counter and how it helps firm owners feel less isolated.

Like always, this conversation goes past ‘tax talk’. It’s an honest discussion about growth, pressure, faith, family, and what happens when success starts to cost more than you expected.

Episode Highlights:

0:00 - Logan’s early entrepreneurial streak
5:09 - Who Logan is and how he built his firm
12:11 - Buying a firm vs. starting from scratch
21:45 - How to know if you’re ready for firm ownership
25:36 - The reality of content and social media
33:18 - Sponsored content, brand fit, and authenticity
38:44 - Hiring help and knowing when it’s time
45:44 - Why an admin hire might be the smartest next move
51:36 - Faith, family, and balancing it all
53:29 - More money, more problems
1:03:46 - What Logan would do differently starting over
1:05:33 - The shift from compliance to advisory
1:08:43 - Building a modern firm in an old-school profession

1:10:58 - Episode wrap-up

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH LOGAN GRAF

Website: https://www.graftaxco.com/

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

TRY COUNTER COMMUNITY FOR FREE

https://counter.circle.so/checkout/thefuncpa

Most accounting firms don’t have a tech problem. They have a trust problem.

In this episode, Yuri sits down with Jonathan Shkolnik, a developer turned founder building Portali, an AI bookkeeping tool designed to take the pain out of cleanups and month-end work. They talk through why accountants are so change resistant, how to evaluate new tools without getting burned, and what “automation” actually means when accuracy still matters and someone has to own the final review.

They also get into the practical stuff people actually worry about, how bank connections break, when uploading statements is a better workflow, what happens with credit card activity, and why “just export it to Excel” is still a real need for tax focused firms.

Episode Highlights:

0:00 - Intro

0:33 - Meet Jonathan + his background

4:16 - Building products for accountants

6:40 - Resistance and pushback

9:30 - Bringing on new tech (don’t wait for the pain)

13:10 - What does Portali do? (and how does it help)

24:11 - Addressing pain points around file sharing, docs and Excel

30:50 - Connecting banks and cards to Portali

36:35 - Being a digital nomad

40:55 - Wrap-up, where you can find Jonathan

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH JONATHAN SHKOLNIK

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

Website: https://portali.tech

In this episode of the Fun CPA podcast, Yuri sits down with Blake Oliver, CPA and host of "The Accounting Podcast," to discuss the evolving landscape of the accounting profession.

Blake shares his unique journey from professional cellist to firm owner, and eventually to a leading voice in accounting technology and media. Blake also shares his POV on automation and AI, firm management, scaling, the technology of it all and of course – where the profession itself is headed.

Whether you are a seasoned CPA, a firm owner, or an accounting student, this conversation offers valuable perspectives on navigating technology and building a successful career in the modern accounting world

Episode Highlights:

0:00 - Intro

0:45 - Episode open and intro to Blake Oliver

3:14 - How Blake got into accounting

7:00 - How Blake got clients in the beginning

9:00 - Reasoning for selling

13:58 - Advice for those looking to sell their firm

16:07 - Post-sale

20:00 - Blake’s podcast (and how it became his ‘job’)

24:20 - Balancing authenticity in your brand while taking on sponsors

27:21 - 150 Hour Credit, what’s next to help the profession grow

35:33 - How do you vet your apps?

41:20 - “Are you optimistic about the profession?”

47:00 - Advice for students

50:00 - Firm growth

52:00 - Standing out at conferences

53:31 - Episode wrap-up

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH

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

Website: https://www.thefuncpa.co/

CONNECT WITH BLAKE OLIVER

Website: https://www.blakeoliver.com/

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

This episode is a little different — no guest, just Yuri pulling back the curtain on how his firm actually runs during the middle of tax season.

Recorded on March 3rd, Yuri walks through what tax season looks like inside his firm right now: how he tracks returns, why he still uses a spreadsheet workflow, and what he’s experimenting with to improve operations. He also shares the reality of running a lean accounting firm, managing part-time help, and balancing client work while keeping his weekly schedule under 40 hours.

Along the way, Yuri breaks down his tech stack, discusses the pros and cons of hiring too quickly, and explains how he structures pricing and client selection to keep the firm profitable without burning out.

Episode Highlights:

0:00 - Trailer
00:52 - Why this is a solo episode
2:52 - Tax season reflections so far
6:23 - The spreadsheet that runs the firm
9:23 - Pricing structure and payment process
11:15 - Why spreadsheets still work (for now)
15:47 - Why hiring too quickly can backfire
19:20 - Managing the schedule under 40 hours
21:07 - How Yuri chooses which clients to work with
24:41 - Why solo firm tax seasons feel different
27:24 - Closing thoughts

ABOUT HOST YURI KAPILOVICH

Yuri, aka #thefuncpa, has been in the accounting profession for over 15 years and has seen, first hand, the challenges the profession brings. After seeing that no firm was fitting the bill, Yuri set out to do things his own way with his firm K&A and the journey began with LinkedIn posting at the front end.

Yuri is proud to bring you #thefuncpa podcast highlighting the fun and all the amazing opportunities our profession can bring us all.

CONNECT WITH YURI KAPILOVICH
LinkedIn: https://www.linkedin.com/in/ykapilovich/
Website: https://www.thefuncpa.co/