For physicians and medical professionals, the financial journey from residency to retirement can be as complex as any clinical case.

Frankie and Sarah welcome Deanna Cregg, Partner at Arcadian Group, to unpack the key tax and structuring decisions doctors face at each career stage.

From the first days of self-employment to planning for retirement, Deanna explains when it makes sense to incorporate, how to structure share ownership for maximum flexibility, and why thinking ahead about investment income, spouse involvement, and ancillary services can save headaches and money down the road.

Whether you’re a new resident, an established practitioner, or an advisor working with medical professionals, this conversation offers clear, practical insight into a highly specialized area of tax planning.

What to Expect:

• When physicians should consider incorporating their practice
• How medical professional corporations differ from other professional corps
• Income splitting and retirement planning benefits for spouses
• Common misconceptions about investment income, ancillary services, and corporate structures
• And more!

Connect with Frankie Loreto and Sarah Netley:

• Courtice.BakerTilly.ca
• LinkedIn: Baker Tilly Canada
• LinkedIn: Frankie Loreto
• LinkedIn: Sarah Netley
• Call: (905) 579-5659

Connect with Deanna Cregg:

• LinkedIn: Deanna Cregg, CPA, CA

About Our Guest:

As a partner at Baker Tilly KDN (BT KDN), Deanna Cregg serves a variety of small to mid-size businesses. Specializing in assisting professionals – doctors, lawyers, dentists, and veterinarians- Deanna provides comprehensive accounting and tax advisory services tailored to the unique needs of owner-managed businesses to achieve the greatest tax efficiencies available.

Deanna graduated from Brock University with a Bachelor of Accounting (Honours) in 2012 and obtained her Chartered Accountant designation in 2013. She joined the Baker Tilly Canada network in 2009 as a co-op student and was hired full-time in 2012. Deanna became a partner with BT KDN in 2024.

Expanding into the United States sounds exciting… until the tax rules hit you.

In this episode, Frankie and Sarah sit down with cross-border tax specialist David Downie to unravel the real considerations Canadian business owners face when they decide to move south, scale into new markets, or invest across the border.

What starts as a simple question, “Should I set up a U.S. company?” quickly turns into a maze of entity choices, integration breakdowns, foreign affiliate rules, and unexpected tax traps. David brings clarity to everything from LLC pitfalls to how “mind and management” can trip up Canadian entrepreneurs without them realizing it.

You’ll hear about:

• When a U.S. subsidiary actually makes sense
• Why LLCs, while popular in the U.S., are often disastrous for Canadians
• The surprising “services business” trap that catches companies off guard
• How cross-border loans between family members can trigger withholding taxes
• The real meaning of “it depends” in cross-border tax planning
• And more!

Connect with Frankie Loreto and Sarah Netley:

• Courtice.BakerTilly.ca
• LinkedIn: Baker Tilly Canada
• LinkedIn: Frankie Loreto
• LinkedIn: Sarah Netley
• Call: (905) 579-5659

Connect with David Downie:

• ddownie@bakertilly.ca
• LinkedIn: David Downie

About our Guest:

David leads Baker Tilly Nova Scotia’s International Tax practice. He is a seasoned cross-border and financial services tax specialist with over 28 years of Canadian and international tax experience, with recognized expertise in cross-border structuring, loan and with repatriation planning. David was a Senior Tax partner at KPMG Canada for 10 years and has also worked at OMERS, one of Canada’s largest pension funds, leading their Enterprise Tax function.

In addition to serving a broad range of clients with domestic and international issues, David is a frequent lecturer and author with organizations such as the Tax Executive Institute (Canada and the US) and the Canadian Tax Foundation. He was also a Program Designer, Lecturer, and Tutor for the In-Depth Tax Program taught to new Canadian tax professionals for many years.

David has a Bachelor of Commerce degree from the University of Guelph.

Something of an amateur chef, David also enjoys cycling, skiing, and spending time with his family in Collingwood, Ontario.

When your budget update sounds like “not much to see here,” you know it’s been a quiet year in tax, but that doesn’t mean there isn’t a lot to unpack.

Frankie and Sarah sit down with Baker Tilly tax partner Rosa Maria Iuliano, who’s been locked in on federal budgets for over two decades (yes, 22 years!). Together, they break down the 2025 federal budget, not just what’s in it, but what’s been quietly removed or delayed, including the capital gains inclusion rate increase, bare trust filing, and the underused housing tax.

From tax credits for personal support workers to new rules around investment income and passive corporate tax planning, they cover what’s relevant (and what’s not) for business owners, professionals, and anyone just trying to file their return without drama.

What to expect:

• Why the 2025 budget was blissfully boring and why that’s a relief
• The elimination of UHT (finally!) and what still applies
• How the CRA is quietly cracking down on personal services businesses
• What professionals need to know about tiered corporations and refunds
• And more!

Connect with Frankie Loreto and Sarah Netley:

• Courtice.BakerTilly.ca
• LinkedIn: Baker Tilly Canada
• LinkedIn: Frankie Loreto
• LinkedIn: Sarah Netley
• Call: (905) 579-5659

Connect with Rosa Maria Iuliano:

• riuliano@bakertilly.ca
• LinkedIn: Rosa Maria Iuliano, FCPA, FCA

About Our Guest:

Rosa Maria graduated from the University of Waterloo with her Master’s in Accountancy in 1998, and obtained her CA designation in 2000 and became a Fellow in 2020. Rosa became a partner in the Taxation Services Department of Baker Tilly Ottawa in 2008. A well-rounded senior accounting and business leader, FCPA, FCA, with over 20 years of experience providing taxation and financial advisory solutions to proprietorships, partnerships, owner-managed corporations, not-for-profit organizations, and high net worth individuals.

Rosa completed the CICA In-Depth Tax Course in 2001, the CICA GST In-Residence Course in 2003, and the CICA Corporate Reorganization and International Taxation Course in 2004. Rosa leverages wide-ranging taxation experience that spans industries including retail, manufacturing, franchising, construction, professional services, real estate, hi-tech, R&D, medical, dental, not-for-profits and charities.

Rosa specializes in providing income tax, commodity tax, and financial planning advice to proprietorships, partnerships, and owner-managed corporations as well as not-for-profit organizations. She leads a tax practice that empowers clients in areas such as succession planning, wealth, retirement, financial management planning, compliance, and identifying/quantifying claims for eligible scientific research and experimental development activities. She has direct experience helping clients deal with complex estate planning and succession issues.

An excellent speaker, Rosa is an active lecturer, seminar leader, media contributor, and guest speaker on tax-related topics, including small business start-up, general tax and financial planning for small-to-medium-sized businesses, employment versus self-employment, GST, and financial planning/wealth management.

Winner of the Institute of Chartered Accountants of Ontario’s Award of Distinction and Ottawa Business Journal’s Top Forty Under 40 Award, as well as the 2014 Women’s Business Network Professional Businesswoman of the Year.