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/