Barenaked Money

Cross Border for Business Owners

Cross Border for Business Owners: Tax Residency, Departure Taxes, and Cross-Border Planning (with Todd King) In this special bonus episode, Matt Kempton and Devin Cattelan, specialists in cross-border services with Verecan Capital Management, are joined by Todd King, Tax Practice Leader at Baker Tilly Nova Scotia, to discuss what business owners should know before moving between Canada and the United States. King explains how the two countries' tax systems differ and why changing tax residency can create unexpected complications. The conversation covers Canada's departure tax, which can leave business owners facing a substantial tax bill even without selling their company, along with strategies that may help reduce or defer that tax. They also discuss the risk of double taxation, how U.S. business structures such as LLCs can create complications in Canada, and the tax considerations surrounding trusts, insurance policies, and investments. Drawing on his experience working with clients on both sides of the border, King shares examples of situations where early preparation helped avoid costly problems, as well as cases where people sought advice after relocating. The discussion also covers the potential tax consequences of renouncing U.S. citizenship or relinquishing a long-held green card, emphasizing the importance of planning before a move, while more options may still be available. Click here to view the episode transcript. Mentioned in this episode (and worth checking out): · Planning for U.S. Expatriation: The Ins and Outs of IRC 877A (00:00) - Welcome and Setup (01:01) - Meet Todd King (01:42) - Canada vs U.S. Tax Basics (03:50) - Residency Changes and Complexity (05:14) - Canada Departure Tax Explained (08:37) - Planning to Reduce Exit Tax (12:50) - Late Calls and Double Tax Traps (17:29) - U.S. Owner Moving to Canada (19:15) - LLC Trap and Entity Mismatch (22:54) - Pre Move Planning Ideas (28:16) - Trusts and Estate Planning Issues (32:35) - Case Study Structuring the Move (35:34) - Investments and PFIC Pitfalls (37:56) - U.S. Expatriation Exit Tax Rules (42:44) - Wrap Up and Disclosures

Moving North: The Truth About Canadian Immigration

Moving to Canada: Citizenship by Descent, Express Entry, and Common Immigration Pitfalls (with Grace Allen) In this special bonus episode, Matt Kempton and Devin Cattelan of Verecan Capital Management, specialists in cross-border services with Verecan, interview Halifax immigration lawyer Grace Allen about what Americans should know before relocating to Canada, stressing that immigration, tax, investment, banking, estate planning, and lifestyle planning must align. Allen explains two main permanent-move avenues: family (citizenship by descent - potentially far back after Citizenship Act changes in December 2025 - and spousal sponsorship leading to permanent residence) and economic immigration, chiefly Express Entry, a points-based system now emphasizing category-based draws such as French proficiency (outside Quebec), healthcare, and trades, with options like provincial nomination. Timelines are typically 6–12 months after invitation, but candidates can wait years in the pool and may use temporary pathways like CUSMA work permits. She debunks buying property or investing as a shortcut, warns DUIs and non-disclosure can cause bans for serious criminality/misrepresentation, and notes citizenship can follow 1,095 days of presence as a PR plus testing and ceremony. Click here to view the episode transcript. (00:00) - Moving to Canada Basics (00:28) - Meet Immigration Lawyer Grace (01:38) - Who Can Move to Canada (02:04) - Citizenship by Descent (06:17) - Proving Your Lineage (07:35) - Economic Immigration Reality (09:16) - Express Entry Explained (11:48) - Invites Medical and Background (13:49) - Timelines and Temporary Options (15:15) - CUSMA Work Permits (16:49) - You Cant Buy PR (19:11) - DUI and Criminal Inadmissibility (21:39) - Common Application Mistakes (23:11) - DIY vs Hiring a Lawyer (27:13) - Culture and Labor Needs (29:11) - Path to Citizenship (31:05) - Final Advice and Wrap Up (33:44) - Outro and Disclaimers

153: Risk & Your Investments

Risk vs. Volatility: Why “More Risk = More Return” Can Mislead Investors Josh Sheluk and Colin White discuss how “risk and return” is widely marketed yet poorly understood, arguing that the industry often equates risk with volatility using measures like standard deviation, even though risk is subjective and tied to an investor’s goals. They outline different risks—volatility, permanent loss, inflation, liquidity, and behavioral risk—and stress that avoiding risk has costs, as seen in insurance and in giving up liquidity via products like long-term GICs or private investments. They challenge the simplistic pitch that more risk guarantees more return, noting examples where higher risk can have low expected returns (lotteries, casinos, zero-day options, concentrated positions, leveraged ETFs, and prediction markets). Their key point: define risk relative to objectives and time horizon, and be wary of sales-driven risk framing. Click here to view the episode transcript. (00:00) - Aug2026: The True Cost of Risk (00:12) - Podcast Intro (00:57) - Risk Return Myths (02:59) - Marketing Risk Reduction (05:27) - Volatility Versus Risk (06:56) - Goals Based Risk (12:30) - Liquidity And GICs (14:45) - Why Risk Pays (15:47) - When Risk Fails (19:11) - Stocks Versus Bonds (21:25) - Expected Versus Realized (25:12) - Managing Risk Tools (27:39) - Insurance And Cost (30:03) - Smart Versus Dumb Risks (32:31) - Leverage And Betting (36:54) - Final Takeaways (39:04) - Outro And Disclosures 00:00 The True Cost of Risk 00:12 Podcast Intro 00:12 Podcast Intro 00:57 Risk Return Myths 02:59 Marketing Risk Reduction 05:27 Volatility Versus Risk 06:56 Goals Based Risk 12:30 Liquidity And GICs 14:45 Why Risk Pays 15:47 When Risk Fails 19:11 Stocks Versus Bonds 21:25 Expected Versus Realized 25:12 Managing Risk Tools 27:39 Insurance And Cost 30:03 Smart Versus Dumb Risks 32:31 Leverage And Betting 36:54 Final Takeaways 39:04 Outro And Disclosures

152: ETFs VS Mutual Funds | Which Are Better?

ETFs vs Mutual Funds: Wrappers, Not Winners Josh Sheluk and Colin White of Verecan Capital Management debunk the belief that ETFs are inherently good and mutual funds inherently bad, arguing both are simply investment “wrappers” and that what matters is what’s inside, the strategy, costs, and role in a portfolio. They explain how mutual funds have historically been associated with higher-cost active management while ETFs began as lower-cost passive index vehicles, but the lines have blurred with actively managed ETFs and low-cost passive mutual funds. Key structural differences include ETFs trading intraday on an exchange with bid-ask spreads and liquidity considerations, while mutual funds transact at end-of-day NAV. They discuss risks of complex/leveraged ETF products, note similar strategies can exist in mutual funds, and contrast hedge funds as more loosely regulated, often higher-cost and less liquid. They also explain why Verecan launched pooled mutual funds to simplify reporting, improve execution efficiency, and potentially reduce client costs without adding fees. 00:00 ETFs vs Mutual Funds Myth 02:52 Defining the Wrappers 04:33 Active vs Passive Origins 07:02 Marketing and Narrative Shift 08:52 Cost vs Value Debate 10:23 ETF Hype and Copycats 11:26 Hidden Costs and Bid Ask 13:10 Trading Mechanics and Liquidity 15:28 Leveraged ETFs and Strategy Risk 18:17 Hedge Funds Explained 24:39 Why We Launched Our Funds 28:47 Wrap Up and Disclosures

151: IPO Games and SpaceX

Why Retail Investors Should Avoid IPOs (SpaceX, OpenAI, and Index Inclusion Games) Josh Sheluk and Colin White of Verecan Capital’s Barenaked Money explain what an IPO is, why companies go public, and the trade-offs versus staying private, including disclosure requirements and transparency. They argue retail investors should generally avoid IPOs because offerings are structured to favor insiders and investment banks, often rely on hype and limited float to influence valuation, lack a meaningful public track record, and tend to lose money or underperform the market on average—especially for buyers who can’t access the IPO price. Using SpaceX as a timely example, they discuss its extreme valuation, heavy losses, and the unusual, accelerated index-inclusion process and float adjustments that invite complex “gamesmanship” by large traders, making it a risky arena for individuals. They conclude markets can still build wealth, but it’s better to avoid IPO speculation. Click here to view the episode transcript. (00:00) - Should You Invest (00:08) - Podcast Intro (00:50) - What Is an IPO (02:11) - Public vs Private (06:10) - Why IPOs Are Risky (09:21) - IPO Data and Odds (12:06) - SpaceX and Mega IPOs (14:51) - Index Inclusion Games (20:44) - Float and Weighting (27:32) - Final Takeaways (29:45) - Outro and Disclosures 00:00 Should You Invest 00:08 Podcast Intro 00:50 What Is an IPO 02:11 Public vs Private 06:10 Why IPOs Are Risky 09:21 IPO Data and Odds 12:06 SpaceX and Mega IPOs 14:51 Index Inclusion Games 20:44 Float and Weighting 27:32 Final Takeaways 29:45 Outro and Disclosures

150: How Much Do You Need to Retire

How Much Do You Need to Retire? Why the Question Is Wrong—and What to Ask Instead Hosts Josh Sheluk and Colin White of Barenaked Money discuss why common retirement questions—like how much money you need, when you can retire, average retirement spending or savings by age, and the “safe” 4% withdrawal rule—are often useless without personal context. They emphasize retirement planning is goals-based and depends on expected spending, timing, pensions, taxes, inflation, market variability, and especially changing priorities over time. They critique reliance on averages and fear-based industry numbers, and note plans rarely unfold in straight lines, citing unpredictable events and life changes. Their recommended approach is to focus on financial independence, understand trade-offs (e.g., retiring early vs. paying for kids’ education or buying a cottage), build flexibility and “slack,” and “retire to something” by replacing work’s purpose and social structure. They liken a financial plan to Google Maps that reroutes as conditions change. Click here to view the episode transcript. (00:00) - Tradeoffs That Matter (01:03) - Retirement Number Myth (03:12) - Why It Depends (04:54) - When Do You Need It (07:06) - Chasing A Target (11:35) - Financial Independence Mindset (13:35) - Average Is Useless (16:41) - Savings Benchmarks Trap (20:29) - Safe Withdrawal Rate (24:47) - When Can I Retire (25:12) - Biggest Variable You (29:44) - Better Questions To Ask (32:09) - Retire To Something (33:14) - Google Maps Planning (35:16) - Wrap Up And Disclosures 00:00 Tradeoffs That Matter 01:03 Retirement Number Myth 03:12 Why It Depends 04:54 When Do You Need It 07:06 Chasing A Target 11:35 Financial Independence Mindset 13:35 Average Is Useless 16:41 Savings Benchmarks Trap 20:29 Safe Withdrawal Rate 24:47 When Can I Retire 25:12 Biggest Variable You 29:44 Better Questions To Ask 32:09 Retire To Something 33:14 Google Maps Planning 35:16 Wrap Up And Disclosures

149: Canada Strong Fund | Sovereign Wealth Fund

Canada Strong Fund vs. Sovereign Wealth Funds: Why Borrowing to Invest at Home Could Backfire Hosts Josh Sheluk and Colin White discuss the proposed Canada Wealth/Canada Strong Fund and argue it differs materially from traditional sovereign wealth funds. They explain sovereign wealth funds originated as a response to “Dutch disease,” using commodity windfalls to build large funds (e.g., Norway’s) that invest outside the country to diversify and stabilize the domestic economy and currency. By contrast, they say Canada would start with about $25B in borrowed money, likely invest domestically, and overlap with existing vehicles like the Canada Infrastructure Bank and Canada Growth Fund without clear details on governance, cost of capital, returns, or liquidity. They warn government investing can become politically driven, may crowd out private capital, and fear a retail component with capital guarantees would shift risk to taxpayers and repeat past failures like labour-sponsored venture capital funds. Their current verdict is “no.” 00:00 Sovereign Wealth Hype 00:21 Show Intro and Setup 01:26 What Sovereign Wealth Means 02:44 Dutch Disease Origins 05:03 Norway Model Explained 06:59 Canada Strong Fund Basics 08:46 Where Will It Invest 10:35 Domestic Focus and Diversification 11:38 Government Investing Risks 14:04 Retail Investor Idea Alarm 16:38 EV Subsidies as Warning 19:26 What Government Should Do 21:09 Labor Fund Cautionary Tale 23:04 Guarantees and Liquidity Problems 31:06 Best Case vs Worst Case 33:43 Verdict and Wrap Up 35:17 Disclaimers and Credits

Seminar Five Things You Can Do in Investing But Shouldn't

148: Behind the Bets: The Truth About Prediction Markets

Prediction Markets: Why They’re Gambling, Not Investing Hosts Josh Sheluk and Colin White of Verecan Capital Management discuss the rise of prediction markets (e.g., Polymarket, Kalshi, and a planned Wealthsimple product in Canada) following regulatory approvals, and argue people should avoid them. They frame the episode as a “draft of bad ideas,” led by the claim that participants will likely lose money, citing research on 1.4 million users and $20B in transactions showing profits are concentrated (1% earning ~80% of profits) and losses can be extreme (0.1% accounting for 43% of losses). They warn prediction markets are prone to manipulation and insider-information advantages, give examples of odds moving ahead of events, and criticize regulators’ rationale that people will do it anyway. They emphasize these products blur investing and gambling, siphon money from long-term investing, and are gamified to drive activity. Click here to view the episode transcript. 00:00 Wild Prediction Market Hook 00:12 Show Intro and Today’s Topic 00:55 Why Prediction Markets Are Exploding 03:17 Regulators Open the Door 05:02 Draft Pick One You’ll Lose Money 08:52 Draft Pick Two Manipulation and Insider Info 14:13 Draft Pick Three Gambling Not Investing 17:07 Money Drain and Social Harm 19:02 You Don’t Need This to Hedge 22:03 Gamification and Worst Case Losses 23:32 What Prediction Markets Actually Are 27:34 Where This Is Headed and Final Thoughts 30:40 Sponsor Message and Contact Info 31:22 Legal Disclaimer and Wrap Up

147: Scams Don’t Look Like Scams Anymore

AI-Powered Misinformation and Financial Scams: Fake Opportunity, Authority, and Urgency Hosts Josh Sheluk and Colin White of Barenaked Money welcome back misinformation researcher and author Matthew Facciani (Misguided) to discuss current misinformation trends, especially how AI scales personalized scams across social media, email, and increasingly convincing audio deepfake phone calls. Facciani outlines three common scam patterns—fake opportunity, fake authority, and fake urgency—and shares examples of AI-tailored job-offer and book-club scams that quickly pivot to small fees. He recommends habits and tools to reduce risk: pause and reflect before reacting emotionally, avoid clicking links, verify credentials via official sources, use lateral reading to check independent coverage and digital footprints, and leverage tools like reverse image search, the Wayback Machine, and URL checks. The conversation also covers identity and network overlap as drivers of bias, plus Facciani’s interactive tools for mapping identity complexity and social network diversity. Click here to view the episode transcript. Mentioned in this episode (and worth checking out): · Misguided: The Newsletter · Identity Map Tool · Verecan Blog: Don't Get Fooled Out of Your Money: Fact-Checker Guide for Every Kind of Investor 00:00 AI Scam Wake Up 00:11 Meet The Misinformation Expert 01:25 State Of Misinformation Now 03:23 Financial Scams Three Buckets 05:35 Deepfakes Voice And Text 06:48 Personalized Job Offer Scam 11:18 Spotting Scams Daily Habits 13:48 Book Club Flattery Trap 17:54 Predatory Conferences Gray Lines 20:49 Verify Claims With Lateral Reading 25:20 Identity Bias Map 26:41 Overlapping Identities Risk 28:46 Complexity Score Tool 30:29 Network Diversity Shield 34:29 Echo Chambers Everywhere 35:34 Privacy And Metrics 36:34 Critical Ignoring Chatbot 40:21 Making It A Business 41:41 Contrarian Matching Ideas 44:48 Where To Find Everything 47:16 Contact Info And Disclosures 47:16 Financial Advisor Disclaimer