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Taking Advice with Moira Somers | E035

Moira Somers

Psychologist Dr. Moira Somers joins Jason Pereira to explore why financial advice is so hard to give and to follow. Listeners will hear how judgment from advice-givers pushes people toward easy defaults, why paying with credit dulls the pain of spending, and why early feedback matters before problems grow.

Group Retirement with Brian McClennon | E034

Brian McClennon

Brian McClennon, CEO of Link Investment Management, discusses group retirement plans with Jason. The episode covers the digital investment options employers can offer employees, how Group RSP portfolios are assigned based on suitability, and why some DC pension plans lock funds in until retirement.

Being Ready To Sell Your Business with Dave Sinclair | E033

Dave Sinclair

Transition coach Dave Sinclair joins Jason to explore the emotional side of selling a business. Learn why owners often feel lost after an exit, how defining an ideal life and breaking it into a day-to-day journey helps, and why a growth mindset makes major life shifts easier to navigate.

Cashflow Management with Tracey Bissett | E032

Tracey Bissett

Cash-flow coach Tracey Bissett of Bissett Financial Fitness joins Jason to tackle cashflow management. The conversation covers the most common cash-flow mistakes entrepreneurs make, what to consider before borrowing from family and friends, and how mindset shapes money decisions in a business.

Amplifying Philanthropy with Mark Halpern | E031

Mark Halpern

Mark Halpern, CEO of WEALTHinsurance.com, talks with Jason about amplifying philanthropy through insurance and other planning tactics. Listeners will learn how charitable giving fits into a financial plan, why understanding a future tax bill matters, and how insurance can help fund larger gifts.

Living Benefits with Brian Laundry | E030

Brian Laundry

Insurance expert Brian Laundry joins Jason to discuss living benefits and what business owners can do to protect themselves in case of disability. The episode covers how common disability is among Canadians, how critical illness insurance pays a tax-free lump sum, and the conditions behind most claims.

Disability Planning with Guy Anderson | E029

Guy Anderson

Guy Anderson of Aligned Capital rejoins Jason to cover disability planning for business owners. Learn when a business must register with WSIB, how provincial disability programs work, and what owners can consider when planning for themselves, family members, or employees living with disabilities.

Bringing Purpose & Meaning To Your Investments with David O'Leary | E028

David O'Leary

Jason talks with David O'Leary, Founder and Principal of Kind Wealth, about bringing purpose and meaning to investing. The episode explains what ESG actually measures, how socially responsible investing works in practice, and the role shareholder activism can play in driving change.

Enabling Remote Work with Chad Davis | E027

Chad Davis

Chad Davis of LiveCA, an all-remote accounting firm, shares with Jason how his team built a fully distributed operation. Listeners will learn the phases of workflow development LiveCA worked through, why remote work is more about culture than technology, and practical tips for improving a remote team.

Planning and Investing for Business Owners with Guy Anderson | E026

Guy Anderson

The tables turn as Guy Anderson of Aligned Capital interviews Jason on planning and investing within a corporate structure. The episode covers fundamentals like how investment returns are taxed inside a corporation and why the $50,000 passive income threshold matters to incorporated owners.

Royalty Financing For Online Business with Andrew D'Souza | E025

Andrew D'Souza

Jason interviews Andrew D'Souza, Co-Founder and CEO of Clearbanc, about royalty-based financing for online businesses. Learn how revenue-share funding differs from both debt and venture capital, and why alternative capital models are emerging for companies focused on online growth.

Finding Purpose with Money at Later Stages with Peter Merrick | E024

Peter Merrick

Peter Merrick, author of The King of Main Street, returns to talk with Jason about finding purpose with money at later stages of life. The conversation covers different ways to give back, why family wealth often fades by the third generation, and how philanthropy tends to take on meaning around exit time.

Family Law & Business Owners with Heather Hansen | E023

Heather Hansen

Heather Hansen, Partner at Martha McCarthy & Company, joins Jason to explain how family law affects business owners. Listeners will learn the legal ramifications of marriage and separation, how a business's value factors into property division and support, and common myths worth questioning.

Business Owner Health & Human Performance with Dr. Randy Knipping | E022

Dr. Randy Knipping

Jason speaks with Dr. Randy Knipping, Medical Director of the Deerfields Clinic, about the health challenges facing business owners. The episode explores how integrated medicine uses regular measurement and biomarkers to track physical and mental capacity, and what resilience really means under pressure.

Outsourcing Financial Operations of Your Business with Josh Zweig | E021

Josh Zweig

Josh Zweig, CEO of LiveCA, talks with Jason about outsourcing the financial operations of a business. Learn which functions, from bookkeeping to payables to payroll, an outside accounting firm can take on, and how outsourced processes can adapt as a company grows and hires.

Valuing Your Business with Melanie Russell | E020

Melanie Russell

Melanie Russell, President of Kalex Valuations, explains how businesses get valued. The episode covers why cash flow is what generally drives investors, how private company valuations differ from public ones, and what current trends in buyer behaviour suggest for owners thinking about a sale.

Tracking Shares with Jonah Mayles | E019

Jonah Mayles

Jason sits down with Jonah Mayles of Sterling Park Financial to explore insurance tracking shares, an often overlooked corner of estate planning. Listeners will learn how a policy's cash surrender value affects the fair market value of shares, and why this structure matters ahead of a historic wealth transfer.

HR Tips and Best Practices with Kevin Kliman | E018

Kevin Kliman

Kevin Kliman, Co-CEO of the HR platform Humi, shares hiring and people-management lessons with Jason. The conversation covers filtering candidates for culture fit, building an emotional bond between new employees and the team, and why the Employment Standards Act is a floor rather than a target.

CFIB And Why You Should Join with Ryan Mallough | E017

Ryan Mallough

Jason and Ryan Mallough of the Canadian Federation of Independent Business discuss what CFIB does and why small business owners might consider joining. Learn how the advocacy group is guided by its members, and where it is pushing governments on issues like family business transfers and construction disruption.

Tax Implications for Americans Living In Canada with Terry Ritchie | E016

Terry Ritchie

Terry Ritchie of Cardinal Point Wealth Management walks Jason through the tax tricks and traps facing Americans living in Canada who own businesses. The episode explains who counts as a U.S. tax resident, why income left in a Canadian corporation can trigger U.S. tax, and what cross-border owners need to watch.

Creditor Protection & Insolvency with Scott Terrio | E015

Scott Terrio

Scott Terrio, Manager of Consumer Insolvency at Hoyes Michalos, joins Jason to demystify insolvency. Learn what insolvency actually means, how consumer proposals work and who they apply to, and how business owners can think about protecting assets when finances go wrong.

Business Mortgage Lending with Sheldon Brow | E014

Sheldon Brow

Jason talks with independent mortgage broker Sheldon Brow about how mortgage lending works differently for business owners than for the average consumer. The episode covers what lenders examine beyond credit scores, including debt-service coverage, and how owners can make applying for debt easier.

Trusts with Lee Fernandes | E013

Lee Fernandes

Lee Fernandes, Senior Wealth Consultant at Cidel, gives Jason a general education on trusts. Listeners will learn the three certainties a trust must meet, common use cases for wealth protection and control, and how trusts are taxed in Canada.

Venture Capital with Stephanie Choo | E012

Stephanie Choo

Stephanie Choo of Portag3 Ventures gives Jason a plain-language look at venture capital. The conversation covers what venture capitalists actually look for in a team and a market, how to approach them, and how to tell whether a business is even suited to taking on VC money.

Credit Ratings and Alternative Lending with Cato Pastoll | E011

Cato Pastoll

Cato Pastoll, CEO of Lending Loop, talks with Jason about credit ratings and alternative lending for small businesses. Learn the five factors that drive a personal credit score, why keeping credit utilization low matters, and how alternative lenders evaluate a business.

Canada’s COVID-19 Economic Response Plan with Guy Anderson | E010

Guy Anderson

Guy Anderson of Aligned Capital joins Jason to unpack Canada's COVID-19 economic response plan for business owners. The episode explains how the wage subsidy worked, which tax filing and payment deadlines were extended, and how interest rate cuts fit into the government's support measures.

Post Mortem Planning with Trevor Parry | E009

Trevor Parry

Jason and Trevor Parry of TRP Strategy Group dig into post-mortem planning for holding companies. Listeners will learn what happens to corporate investments after an owner passes away, how deemed dividends are taxed, and the roles of loss carrybacks, share redemptions, pipeline transactions, and life insurance.

Cyber Insurance with Greg Markell | E008

Greg Markell

Greg Markell of Ridge Canada walks Jason through the world of cyber insurance. The episode covers why any business that has collected payment information faces breach risk, how ransomware compares to standard data breaches, and what owners can do to protect their companies.

Insurance Planning for Business with Zachary Goldman | E007

Zachary Goldman

Zachary Goldman, Managing Partner of Sterling Park Financial Group, joins Jason to explain why business owners look at insurance as part of their planning. Learn how periodic premiums can lead to a much larger tax-free payment later, and where insurance fits in protecting a business and the people who depend on it.

Mentorship And Grooming The Next Generation with Peter Merrick | E006

Peter Merrick

Jason talks with Peter Merrick, author of The King of Main Street, about mentorship and grooming the next generation of business leaders. The discussion covers what makes a true mentor, why an aging population makes succession pressing, and how owners can find life beyond working on and at their business.

An Introduction to Employee Benefits with Keith Foot | E005

Keith Foot

Keith Foot, CEO of Ralph Moss Insurance, gives Jason a primer on group employee benefit plans. Listeners will learn what a typical plan costs as a share of payroll, how components like life, disability, health, and dental fit together, and ways employers can work to contain costs.

IPPs & RCAs with Fraser Lang | E004

Fraser Lang

Fraser Lang joins Jason to explore retirement planning beyond the RRSP for incorporated business owners. The episode explains how Individual Pension Plans build contribution room with age, when past-service top-ups apply, and how Retirement Compensation Arrangements can supplement a retirement plan.

Fundamentals of Corporate Taxation with Kim Moody | E003

Kim Moody

Jason and Kim Moody of Moodys Gartner Tax Law walk through the fundamentals of Canadian corporate taxation. Learn how the small business rate applies to the first $500,000 of active income, how dividends and salaries differ, and what the Kiddie Tax rules mean when paying family members.

Family Succession Planning with Tom Deans | E002

Tom Deans

Dr. Tom Deans, author of Every Family's Business, joins Jason to talk about exit planning when family succession is on the table. The conversation covers why a willing buyer matters as much as a willing seller, why a smooth transition rests on the owner rather than the children, and how treating kids like valued employees shapes long-term outcomes.

Incorporation & Corporate Structure Planning with Ted Maduri | E001

Ted Maduri

Jason sits down with Ted Maduri, Partner at DLA Piper, to break down how Canadian business owners can build a strong corporate structure from day one. Listeners will learn the trade-offs between sole proprietorships and corporations, when a shareholder agreement becomes essential, and why structuring with an eventual sale in mind matters.

Introducing Financial Planning For Canadian Business Owners

Financial Planning for Canadian Business Owners is Jason Pereira's weekly show for entrepreneurs at every stage, from startup to sale. Each episode features experts on the tax, legal, succession, and personal questions that come with running a business, helping listeners learn what good advice looks like.