
58 - Revisiting Capital Gain Investments with Jason Pisesky
12/30/24 • 34 min
PhE is headed to Cancun this February 23 to March 2 for our Health and Wealth Summit! We'd love to have you join: https://www.physempowerment.ca/cancun
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Dr. Kevin Mailo and Dr. Wing Lim welcome Masterclass faculty member Jason Pisesky back to the show to talk about the recent capital gains changes in Canadian tax policy. Jason is a tax expert with KPMG and he breaks down for Wing why the changes sparked widespread concern among professionals, small business owners, and investors. He and Wing examine the actual impacts, where they were felt most, and what the practical implications of the changes are.
The conversation focuses on the government’s decision to increase the capital gains inclusion rate from 50% to two-thirds for amounts exceeding $250,000 annually, meant only to affect the top 0.13% of Canadians. Jason explains that the policy affects those with significant investments, corporations, and trusts, while individuals have some exemptions. The nine-week notice period left people rushing for solutions, leading to a variety of overreactions, like liquidating assets too early, and responses such as corporate stripping. Jason advises caution against unnecessary asset liquidations that could trigger large, immediate tax bills. Despite the initial panic, Jason reassures listeners that the tax increases are manageable for most with proper planning, emphasizing the importance of consulting experts to avoid unnecessary financial losses.
About Jason Pisesky:
Jason is a tax lawyer with an international accounting firm, KPMG. His practice background is extensive and includes personal and corporate tax planning as well as litigation and dispute resolution. Whether you are scaling up your practice or winding it down, proper coordination between a tax lawyer and your accountant can ensure you're doing it right.
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Jason Pisesky:
Physician Empowerment:
- Attend an upcoming Empowerment Retreat
- Join the Physician Empowerment Masterclass now
- Website: PhysEmpowerment.ca
PhE is headed to Cancun this February 23 to March 2 for our Health and Wealth Summit! We'd love to have you join: https://www.physempowerment.ca/cancun
—
Dr. Kevin Mailo and Dr. Wing Lim welcome Masterclass faculty member Jason Pisesky back to the show to talk about the recent capital gains changes in Canadian tax policy. Jason is a tax expert with KPMG and he breaks down for Wing why the changes sparked widespread concern among professionals, small business owners, and investors. He and Wing examine the actual impacts, where they were felt most, and what the practical implications of the changes are.
The conversation focuses on the government’s decision to increase the capital gains inclusion rate from 50% to two-thirds for amounts exceeding $250,000 annually, meant only to affect the top 0.13% of Canadians. Jason explains that the policy affects those with significant investments, corporations, and trusts, while individuals have some exemptions. The nine-week notice period left people rushing for solutions, leading to a variety of overreactions, like liquidating assets too early, and responses such as corporate stripping. Jason advises caution against unnecessary asset liquidations that could trigger large, immediate tax bills. Despite the initial panic, Jason reassures listeners that the tax increases are manageable for most with proper planning, emphasizing the importance of consulting experts to avoid unnecessary financial losses.
About Jason Pisesky:
Jason is a tax lawyer with an international accounting firm, KPMG. His practice background is extensive and includes personal and corporate tax planning as well as litigation and dispute resolution. Whether you are scaling up your practice or winding it down, proper coordination between a tax lawyer and your accountant can ensure you're doing it right.
__
Jason Pisesky:
Physician Empowerment:
- Attend an upcoming Empowerment Retreat
- Join the Physician Empowerment Masterclass now
- Website: PhysEmpowerment.ca
Previous Episode

57 - Medical Entrepreneurship Series with Dr. Adenike (Nike) Olowu and her husband, Daniel Ashaolu
PhE is headed to Cancun this February 23 to March 2 for our Health and Wealth Summit! We'd love to have you join: https://www.physempowerment.ca/cancun
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Dr. Kevin Mailo introduces another episode in the Medical Entrepreneurship Series. Dr. Wing Lim interviews guests Dr. Adenike (Nike) Olowu and her husband, Daniel Ashaolu, masterclass members and entrepreneurs. Dr. Olowu is a full-time family physician and her husband Daniel manages their growing real estate portfolio. They tell Wing about their journey of coming to Canada, setting up practice, and how they are not just thriving but soaring.
Dr. Adenike Olowu went to medical school in Nigeria, where she did her residency at University College Hospital before coming to Canada in 2017. She practiced for six years prior to immigrating and she describes the process of getting certified to practice in Canada. By January of 2020 she was practicing here. Daniels explains why they chose Canada and then Alberta, how the move worked for their children, and how they decided to start their real estate investing journey. Wing explores the fascinating process of how the pair dove into entrepreneurship and investing and what steps they took to ensure success.
About Dr. Adenike (Nike) Olowu:
Dr. Ashaolu Adenike Oluwatoyin Mulikat, also known as Dr. Ashaolu [Ash-a-loo], is a family medicine physician working out of the Elk Point Healthcare Centre and the Ayobami Oyebode Medical Clinic. She became the third family physician to practice in town. Dr. Ashaolu comes to Elk Point from Winnipeg. She arrived in Canada in September 2017 after completing her medical training and residency in Nigeria.
With plans to specialize in geriatric medicine, Dr. Ashaolu enjoys cooking and hiking as well as spending time with her husband Daniel Ashaolu and their three children: Joshua, Jemimah and Joy.
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Physician Empowerment:
- Join the Physician Empowerment Masterclass now
- Website: PhysEmpowerment.ca
Next Episode

59 - Long-Term Investments and Tariffs with Diana Choi
PhE is headed to Cancun this February 23 to March 2 for our Health and Wealth Summit! We'd love to have you join: https://www.physempowerment.ca/cancun
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In this episode, Dr. Wing Lim introduces a discussion with Diana Choi, team lead to a group of portfolio managers, about professional investment strategies. Diana Choi explains her investment philosophy; looking at the unpredictability of the future and the importance of focusing on quality businesses. She tells Wing that successful companies are ones that can perform well in various market conditions, thriving in good times and surviving in downturns. Through this approach, refined over 25 years, risk-adjusted returns can be delivered by identifying strong businesses that are resilient to market fluctuations.
Dr. Lim and Diana Choi also explore the idea that investment decisions should not hinge on short-term events or political cycles, such as presidential elections. Quality companies transcend political changes and Diana points to the example of CCL Industries, a label-making firm with strong cash flow and growth potential. This strategy makes robust fundamentals a priority and not trends, fads, or short-term gains. The conversation highlights the disciplined effort that is needed to assess and maintain investments, with a focus on the value of patience, diligence, and durable business models.
Physician Empowerment:
- Attend an upcoming Empowerment Retreat
- Join the Physician Empowerment Masterclass now
- Website: PhysEmpowerment.ca
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