Podcast appearances and mentions of Barry Ritholtz

What happens when one of investing's original disruptors buys one of the industry's newest disruptors? Barry Ritholtz thinks investors may be the biggest winners and Bill and Jackie dig into why. This special breaking-news is an excerpt from an upcoming Catching Up to FI episode, recorded on 8/26/26. Barry reacts to Vanguard's newly announced agreement to acquire Altruist, the fast-growing technology and custody platform built for independent financial advisors. Barry also gives an important disclosure: he's an Altruist investor, so yes, he has a dog in this fight. From there, he explains why combining Vanguard's enormous scale with Altruist's technology could quickly reshape the custody business, put fresh pressure on Fidelity and Schwab, and potentially extend the famous "Vanguard Effect" into another corner of financial services. Bill calls it "disruptor squared." Barry sees an industry that never stands still. And if competition drives prices lower again, investors may ultimately be the ones cashing the biggest check. This episode covers Barry's immediate reaction to Vanguard's agreement to acquire Altruist His disclosure that he is an Altruist investor and financially benefits from the deal Why Altruist's clean-sheet technology made it an attractive challenger to legacy custodians How Vanguard's scale could immediately change Altruist's competitive position Why Fidelity and Schwab may suddenly have a much larger third competitor The "Vanguard Effect" and how competition can push fees lower across an industry Why Barry believes investors could be the biggest winners from the acquisition How Schwab and Robinhood previously disrupted investing through lower-cost and free trading Why Vanguard was a logical potential acquirer given its earlier relationship with Altruist Barry's larger lesson that financial technology never stands still    The Full Episode with Barry Ritholtz will be coming out soon! Be sure to follow the show or subscribe to the channel on YouTube, so you don't miss it!"   === SUPPORT  THE  SHOW ===

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you a high-income T4 earner who feels financially behind simply because you cannot access the same tax strategies as an incorporated business owner?It is easy to compare your tax bill, investment returns, or wealth-building options with someone playing a completely different financial game. But incorporation does not automatically mean more spendable income, and chasing strategies designed for someone else can distract you from the opportunities already available within your own plan.Through the story of a successful T4 earner with rental properties, registered investments, a DIY portfolio, and substantial home equity, this episode explores why knowing more strategies does not always create greater confidence. The real challenge may be choosing a tax-efficient approach that fits your risk tolerance—and staying consistent long enough for it to work.By listening, you will learn how to:Stop comparing two different financial games. Understand why the corporate small-business tax rate does not tell the full story and why incorporated owners still face personal tax when extracting money from their companies.Evaluate your next wealth-building move more clearly. Explore the trade-offs between seeking higher returns, taking on more investment risk, increasing your income, and improving tax efficiency through strategies such as the Smith Manoeuvre.Build confidence through consistency instead of chasing certainty. Discover why long-term financial confidence rarely comes from finding one perfect strategy—and how a repeatable process aligned with your goals, personality, and comfort with risk can move you closer to financial freedom.Press play now to learn how to focus on the financial game you can actually play—and build a strategy you can confidently follow for years.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.This episode of Canadian Wealth Secrets explores how a high-income T4 earner can improve financial planning, wealth management, and tax efficiency without comparing their situation to an incorporated business owner playing by different tax rules. Using a real listener case involving rental properties, RRSPs, a DIY ETF portfolio, and substantial home equity, Kyle and Jon explain why the small-business corporate tax rate does not equal personally spendable income and why salary versus dividends in Canada must be viewed through both corporate and personal taxation. They examine practical investment strategies, including the Smith Manoeuvre, real estate leverage, RRSP optimization, tax-efficient investing, and using home equity to support long-term wealth building. The conversation also highlights risk management, showing that higher potential returns often require greater concentration, private lending, or other risks that may not fit every investor. Rather than chasing the perfect strategy, listeners are encouraged to create a personalized Canadian wealth plan, define their minimum retirement cash-flow needs, and follow repeatable financial systems that match their investor personality. The core message is that lasting financial freedom in Canada comes from understanding the financial game available to you, choosing a strategy you can confidently maintain, and staying consistent on the path toward financial independence.Ready to connect? Text us your comment including your phone number for a response!PE Gate is now offering accredited investors access to Project Rope: the acquisition of an established, cash-generative Canadian industrial business with more than 45 years of operating history.PE Gate's targets an annualized IRR above 25%, net of carried interest.For the Offering Memorandum and full risk disclosure, visit pe-gate.com or email sarmen@pe-gate.com. If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Barry Ritholtz returns to the Rational Reminder podcast to discuss the biggest mistakes investors make—and why avoiding them may matter more than finding the next great investment. Drawing on decades of experience in markets, wealth management, and financial media, Barry explains why forecasting consistently fails, how investors can distinguish good advice from noise, and why humility, probabilistic thinking, and disciplined behavior are among the most valuable investing skills.   Throughout the conversation, Barry shares lessons from his new book, How Not to Invest, covering everything from media consumption and behavioral biases to index investing, portfolio concentration, market cycles, and choosing a financial advisor. He explains why experts are often better at providing context than making predictions, why social media amplifies poor financial advice, and how investors can build processes that help them stay disciplined through uncertainty. The discussion blends academic research, practical experience, and memorable stories into a comprehensive guide for becoming a better long-term investor.   Key Points From This Episode: (0:04) Cameron and Ben welcome Barry Ritholtz back to the podcast and discuss his new book, How Not to Invest. (4:12) Why successful billionaires often make poor economic forecasters and how the halo effect leads people to overestimate expertise. (6:39) Why Wall Street professionals are generally poor at forecasting future market returns despite their domain expertise. (7:42) What experts are actually good at: providing context, historical perspective, and nuanced analysis rather than predicting the future. (8:47) Barry's checklist for identifying bad financial advice, including emotional appeals, false certainty, and conflicts of interest. (10:35) How social media algorithms reward outrage and overconfidence instead of thoughtful investing. (11:21) Why 24/7 financial news encourages unnecessary action that often hurts long-term investment returns. (12:17) Why long-term investors are often better off ignoring financial news altogether. (13:52) How short-form financial content on platforms like TikTok encourages misinformation and poor investing decisions. (15:22) Gell-Mann Amnesia and why investors should remain skeptical even of trusted news sources. (18:00) How reading books, consuming long-form content, and building a trusted information network improves decision making. (20:21) Barry's definition of investing as making probabilistic decisions with imperfect information in an unknowable world. (22:55) How successful investors focus on controlling savings, asset allocation, discipline, and behavior instead of unpredictable events. (24:52) Why recognizing the limits of your own knowledge is one of investing's greatest advantages. (26:30) How experience, losses, and continuous learning help investors become more self-aware. (27:16) Three ideas that heavily influence Barry's investment philosophy: Sturgeon's Law, George Box's models, and William Goldman's "Nobody knows anything." (30:18) Whether artificial intelligence changes Sturgeon's Law that "90% of everything is crap." (31:46) Three forms of economic innumeracy that lead investors astray: denominator blindness, survivorship bias, and misunderstanding compounding. (36:04) Why understanding secular bull and bear markets is useful psychologically—but not as a timing strategy. (39:12) Why investors should understand market cycles without attempting to trade around them. (40:44) What stock valuations can—and cannot—tell investors about future returns. (42:18) How investors should respond to wars, pandemics, and other major external events. (45:53) The biggest investing lessons from the COVID-19 market crash and why personal experience often differs from market performance. (49:04) Why index investing remains one of the most reliable approaches to long-term wealth creation. (50:44) Why every market forecast should be expressed probabilistically rather than with certainty. (52:06) The lies traders tell themselves and why disciplined risk management separates successful professionals. (56:11) What active investors need if they hope to consistently outperform. (57:24) The biggest behavioral mistakes investors make, including lack of planning, excessive concentration, and ignoring taxes. (59:43) Why concentrated stock positions become dangerous—even after creating substantial wealth. (1:02:33) How sudden wealth and large financial windfalls frequently lead to costly mistakes. (1:05:14) How to identify trustworthy financial advisors by evaluating their process, temperament, and communication. (1:07:27) Why advisors who consistently communicate their thinking help investors avoid emotional mistakes. (1:09:26) Barry's practical blueprint for becoming a better long-term investor: create a plan, invest consistently, define the purpose of money, and build around a diversified index portfolio. Links From Today's Episode: Meet with PWL Capital: https://calendly.com/d/3vm-t2j-h3p Rational Reminder on iTunes — https://itunes.apple.com/ca/podcast/the-rational-reminder-podcast/id1426530582. Rational Reminder on Instagram — https://www.instagram.com/rationalreminder/ Rational Reminder on YouTube — https://www.youtube.com/channel/ Benjamin Felix — https://pwlcapital.com/our-team/ Benjamin on X — https://x.com/benjaminwfelix Benjamin on LinkedIn — https://www.linkedin.com/in/benjaminwfelix/   Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com)  

Peter Brandt entered the commodity trading business in 1976 with ContiCommodity Services, survived years of market shifts, and turned a passion for price action into a legendary career spanning over 50 years as one of the world's premier classical chartists.After starting with Conti handling large institutional accounts like Campbell Soup Company and Homestake Mining, Peter went on to found Factor Trading Co., Inc. (now Factor LLC) in 1980 to trade proprietary capital. Author of the classic Diary of a Professional Commodity Trader and featured in Jack Schwager's Unknown Market Wizards, Peter has spent over five decades navigating inflationary booms, market crashes, and the transition from open-outcry pits to electronic markets. Today, his edge is built on process, discipline, and classical charting principles that have stood the test of time.In this conversation, Peter pulls back the curtain on his five-decade journey, sharing the specific principles that have allowed him to navigate the markets for half a century. He breaks down why high win rates are a myth, how he caps risk at 60–70 basis points per trade, and how he transitioned from searching for quick wins to building a career as a master craftsman in speculation. In this episode, we explore:• Peter Brandt's 50+ year journey from advertising to commodity pits and Factor Trading• Why high win rates are a myth and how the 80/20 Pareto Principle applies to trading profits• How Peter limits risk to 60–70 basis points per trade and why he never pyramids positions• Why he shuns indicators and diagonal trend lines in favor of horizontal classical patterns• Why the real edge comes from risk management and emotional control, not chart patterns• Peter's advice for the next generation on craft, capital preservation, and longevity About Peter Brandt:Peter L. Brandt entered the commodity trading business in 1976 with ContiCommodity Services, a division of Continental Grain Company. In 1980, he founded Factor Trading Co., Inc. (now Factor LLC), trading proprietary capital across forex, futures, fixed income, and equity markets. Over his career, he has managed trading activities for major institutional clients, including Commodities Corporation of Princeton, NJ.Peter is the author of Trading Commodity Futures with Classical Chart Patterns (1990) and Diary of a Professional Commodity Trader (2011), which held Amazon's #1 trading rank for 27 weeks. Featured in Jack Schwager's Unknown Market Wizards and named among the 30 most influential people in finance by Barry Ritholtz in 2011, Peter is widely recognized as one of the world's foremost authorities on classical chart analysis. Links + Resources:X (Twitter): https://x.com/PeterLBrandtWebsite: https://www.peterlbrandt.com/ Sponsor of Chat With Traders Podcast:Trade The Pool: http://www.tradethepool.com Time Stamps:Please note: Exact times will vary depending on current ads. 00:00 How a 50-Year Veteran Thinks About Risk Management05:42 Wanting a Career from Trading09:42 Taking 5 Years to Be Profitable15:20 Don't Quit Your Day Job to Trade Until You Have a Proven Track Record22:30 Cut Losses Short and Let My Winning Trades Run27:00 Understand the Risk and the Probability31:00 20% of My Trades Account for at Least 80% of My Total Profits36:08 Sizing Is Really Important and It Is the Reason Why a Lot of Novices Blow Out43:00 Removing Yourself from the Equation48:30 I Don't Believe in Optimization Where You Have a Set of Rules52:50 I Like Horizontal and Continuation Patterns54:38 I Don't Believe in Indicators Because They're Just Derivatives of Price1:00:00 Technical Analysis: Charts Resonated with Who I Am1:03:20 The Time Frame I Trade1:07:00 How Important It Is to Identify How You Trade1:09:15 Having a Mentor1:14:50 What Are You Most Proud of in Your Career01:20:09 I Enter Every Trade Assuming It's Going to Be a Loser01:26:05 Become a Craftsman of Trading01:33:48 You Can't Go Broke Taking Small Profits, But You Will Go Broke Taking Large Losses01:35:40 Peter's Takeaway He Leaves to the Next Generation of Traders01:36:14 Where Can Traders Find You Trading Disclaimer:Trading in the financial markets involves a risk of loss. Podcast episodes and other content produced by Chat With Traders are for informational or educational purposes only and do not constitute trading or investment recommendations or advice. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat if you could own part of an established Canadian business—without buying the entire company or committing millions to a traditional private equity fund?Private equity has historically been difficult for individual investors to access, even when they qualify as accredited investors. In this episode, the PE Gate team explains its deal-by-deal approach, which is designed for entrepreneurial investors who want to understand the specific business they are backing rather than committing capital to a blind pool. You'll also hear why private equity is generally better suited as one part of an experienced investor's broader portfolio—not as a first or only investment.You'll learn:How PE Gate identifies established, cash-flowing Canadian businesses with long operating histories, trusted owners, niche market positions, and clear opportunities for growthHow due diligence, legal agreements, governance, financial reporting, employee ownership, and active operational support can help manage—but not eliminate—investment riskHow direct business ownership may offer Canadian investors potential advantages through leverage, share liquidity, the lifetime capital gains exemption, and tax-efficient corporate dividends when properly structuredPress play to learn how direct private equity investing works and whether it fits your experience, interests, and long-term portfolio strategy.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.Private equity can play a meaningful role in a broader Canadian wealth plan for accredited investors, business owners, and entrepreneurs seeking tax-efficient investing, financial diversification in Canada, and long-term wealth building beyond public markets. In this episode, PE Gate explains how direct private equity deals can provide access to established, cash-flowing Canadian businesses, allowing investors to participate in business ownership while benefiting from professional due diligence, governance, leverage, and active operational support. The conversation also explores potential tax benefits, including the lifetime capital gains exemption for qualifying individual investors and tax-efficient intercorporate dividends when corporate investments are properly structured. For Canadian entrepreneur finance, these investment strategies may complement corporate wealth planning, corporation investment strategies, capital gains strategy, passive income planning, personal versus corporate tax planning, and business owner tax savings. While a complete financial independence Canada strategy may also involve RRSP optimization, salary versus dividends planning, real estate investing in Canada, retirement planning tools, estate and legacy planning, financial buckets, and other wealth-building strategies in Canada, this episode focuses specifically on how carefully selected private business investments may support corporate structure optimization, financial vision setting, and building long-term wealth in Canada.Ready to connect? Text us your comment including your phone number for a response!PE Gate is now offering accredited investors access to Project Rope: the acquisition of an established, cash-generative Canadian industrial business with more than 45 years of operating history.PE Gate's targets an annualized IRR above 25%, net of carried interest.For the Offering Memorandum and full risk disclosure, visit pe-gate.com or email sarmen@pe-gate.com. If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you so focused on eliminating taxes that you're overlooking better opportunities to grow your wealth?A rising tax bill can feel painful, especially when your business is generating more profit than ever. But paying more tax is often a sign that your income and net worth are growing—and the real challenge is learning how to keep more capital working strategically instead of chasing the unrealistic goal of paying nothing.In this episode, Jon Orr and Kyle Pearce unpack a real business-owner scenario involving a significant corporate tax bill, excess cash, and missed planning opportunities. They explain how a shift in mindset, combined with practical changes to compensation and corporate wealth structure, can create greater flexibility today and stronger long-term outcomes.You'll discover:Why focusing on after-tax wealth growth is more valuable than trying to reduce your tax bill to zero.How adjusting the balance between salary and dividends can create RRSP room, reduce corporate income, and improve tax deferral opportunities.How business owners can put excess corporate cash to work while maintaining liquidity, supporting future investments, and preparing for estate taxes.Press play now to learn how smarter tax planning can turn a frustrating tax bill into a more intentional wealth-building strategy.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs, building a resilient Canadian wealth plan means looking beyond the goal of simply paying less tax and creating financial systems that support long-term growth. This episode explores practical Canadian tax strategies, including salary vs. dividends in Canada, optimizing RRSP room, personal vs. corporate tax planning, and corporation investment strategies for excess business cash. It also examines how leveraged investing through a corporate line of credit may create a tax deduction when borrowed funds are used for eligible business or investment purposes, while emphasizing the importance of investment risk, liquidity, and professional guidance. By organizing capital into financial buckets, coordinating an investment bucket strategy, and combining tax-efficient investing with corporate structure optimization, passive income planning, financial diversification, and legacy planning in Canada, business owners can pursue financial independence, strengthen their estate plan, and build long-term wealth in Canada with greater clarity and flexibility.Ready to connect? Text us your comment including your phone number for a response!PE Gate is now offering accredited investors access to Project Rope: the acquisition of an established, cash-generative Canadian industrial business with more than 45 years of operating history.PE Gate's targets an annualized IRR above 25%, net of carried interest.For the Offering Memorandum and full risk disclosure, visit pe-gate.com or email sarmen@pe-gate.com. If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre your investments, corporate cash, and registered accounts working together—or are hidden gaps costing you money and time to reach financial freedom?Successful incorporated professionals can build significant wealth and still feel unsure whether their financial structure is truly optimized. When accountants, insurance advisors, and investment professionals each focus on only one piece, opportunities involving salary, retained earnings, taxes, and family savings can easily be overlooked.This episode examines a Canadian professional couple's financial setup and reveals the practical adjustments that could help them use their money more intentionally.You'll discover:How to balance salary, retained earnings, and RRSP contributions without withdrawing unnecessary personal income.Why TFSAs, RESPs, and available government grants should be considered before more complex wealth strategies.How idle corporate cash and high-fee investment products can limit long-term growth—and what to evaluate before choosing a better approach.Press play now to uncover the financial blind spots that may be hiding inside an otherwise successful wealth plan.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.Effective wealth management for high-net-worth Canadians requires more than isolated advice—it calls for coordinated tax planning, financial planning, and asset optimization across personal and corporate accounts. For incorporated professionals and business owners, a strong Canadian wealth plan may include RRSP optimization, maximizing RESP grants, evaluating salary vs. dividends in Canada, and building tax-efficient corporate investments with the right balance of growth, safety, and liquidity. The episode explores how corporate wealth planning, personal vs. corporate tax planning, optimizing RRSP room, passive income planning, and corporate structure optimization can support financial freedom in Canada while reducing missed opportunities. It also highlights the value of financial buckets, an investment bucket strategy, capital gains planning, real estate investing in Canada, financial diversification, and business owner tax savings. Whether the goal is financial independence, an early retirement strategy, legacy planning in Canada, or building long-term wealth, Canadian entrepreneurs need financial systems that align retained earnings, registered accounts, insurance, real estate, and corporation investment strategies. With clear financial vision setting and the right retirement planning tools, entrepreneurs can create a more resilient plan for tax-efficient investing, estate planning, and sustainable wealth building in Canada.Ready to connect? Text us your comment including your phone number for a response!PE Gate is now offering accredited investors access to Project Rope: the acquisition of an established, cash-generative Canadian industrial business with more than 45 years of operating history.PE Gate's targets an annualized IRR above 25%, net of carried interest.For the Offering Memorandum and full risk disclosure, visit pe-gate.com or email sarmen@pe-gate.com. If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat do you do when your business is profitable on paper, but payroll, taxes, and contractor payments are due before the cash actually hits your account?A cash flow crunch can make even a successful business feel unstable. You may have strong revenue, promising deals, and money on the way—but if the timing is off, your emergency fund is not prepared, the pressure can quickly turn into sleepless nights and reactive decisions. In this episode, Kyle Pearce and Jon Orr unpack why profitability and solvency are not the same thing, and how Canadian business owners can build systems and tools, and better emergency funds that help them handle cash gaps without panic.You'll walk away with:A clearer understanding of why cash flow crunches happen, even in profitable businesses.A smarter way to think about your emergency fund or “wealth reservoir” so cash is not just sitting idle.Practical insight into how business owners can use structured reserves, policy loans, and strategic planning to keep operations moving while still building long-term wealth.Press play now to learn how to stop fearing the cash flow crunch and start building a system that keeps your business steady when timing gets tight.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs, a strong Canadian wealth plan starts with understanding the difference between profit and cash flow. Even when business growth looks healthy on paper, a cash flow crunch can expose weak cash management, gaps in business finance, and the need for better financial systems. This episode explores how a wealth reservoir can function like a more strategic emergency fund, helping business owners manage payroll, taxes, contractors, and other obligations without derailing long-term financial planning. By building financial systems for entrepreneurs, using corporate wealth planning, considering tax-efficient investing, and aligning personal vs corporate tax planning, business owners can create a stronger business strategy that supports financial freedom Canada, financial independence Canada, passive income planning, legacy planning Canada, and building long-term wealth Canada. Whether you are thinking about salary vs dividends Canada, RRSP optimization, corporation investment strategies, real estate investing Canada, financial buckets, capital gains strategy, estate planning Canada, or an early retirement strategy, the key is to create a flexible investment bucket strategy that supports both modest lifestyle wealth today and long-term wealth building strategies Canada for the future.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs the 4% rule giving you a false sense of security about your retirement plan?The 4% rule is one of the most popular shortcuts in retirement planning, but it was never meant to be followed blindly. If you're a Canadian business owner, incorporated professional, or high-income earner nearing financial freedom, your timeline, tax structure, and market risk may look very different from the “average” retiree the rule was built around. And when markets are expensive, even a strategy that worked historically can become much less reliable.In this episode, you'll discover:Why the 4% rule is a helpful starting point, but not a complete retirement strategy.How high market valuations, bubbles, and sequence of returns risk can dramatically change your odds of success.Why the way your portfolio produces income may matter just as much as the size of the portfolio itself.Press play now to rethink whether your retirement plan is built to survive more than just average market conditions.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian business owners and entrepreneurs approaching financial freedom in Canada, relying solely on the traditional 4% rule or a fixed safe withdrawal rate may not be enough. A strong Canadian wealth plan should account for sequence of returns risk, CAPE ratio retirement risk, market valuation risk, and the need for a flexible retirement income strategy that supports long-term financial independence Canada goals. Instead of focusing only on portfolio size, effective financial freedom planning should consider retirement cash flow planning, income investing Canada, RRSP optimization, salary vs dividends Canada, corporate wealth planning, tax-efficient investing, personal vs corporate tax planning, and corporation investment strategies. Whether your early retirement strategy includes real estate investing Canada, passive income planning, capital gains strategy, financial buckets, or an investment bucket strategy, the goal is to build a retirement portfolio strategy that balances growth, income, tax efficiency, and legacy planning Canada. With the right retirement planning tools, Canadian tax strategies, business owner tax savings, estate planning Canada, financial systems for entrepreneurs, and corporate structure optimization, you can create wealth building strategies Canada that support a modest lifestyle wealth goal today while building long-term wealth Canada for the future.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereMany incorporated business owners believe they have only two choices: pull money out of my corporation now and pay the tax, or leave it inside the corporation and deal with the tax later. But both extremes can create problems. One owner may earn great income yet watch most of it disappear into lifestyle, taxes, and cash flow demands, while another may defer successfully for decades only to face mandatory withdrawals, clawbacks, and a much bigger tax bill in retirement.In this episode, you'll learn:Why high income and high net worth can still lead to the same underlying issue: lack of long-term planning.How aggressive tax deferral can become a future tax trap if there is no strategy for flexibility later.Why the best answer often sits between spending everything today and deferring everything forever—using planning tools that help protect lifestyle, grow net worth, and improve tax efficiency over time.Press play now to learn how to avoid building tomorrow's tax problem with today's financial decisions.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.A strong Canadian wealth plan for business owners requires more than basic tax planning or wealth management—it needs a complete financial planning system that balances tax deferral, leverage, insurance, retirement planning tools, and long-term tax strategies. For Canadian entrepreneur finance, this means understanding personal vs corporate tax planning, salary vs dividends Canada, RRSP optimization, optimizing RRSP room, corporate wealth planning, corporation investment strategies, and corporate structure optimization so you can create business owner tax savings today without building a future tax problem. By using financial buckets, an investment bucket strategy, tax-efficient investing, passive income planning, capital gains strategy, and financial diversification Canada, incorporated professionals can support financial freedom Canada, financial independence Canada, and even an early retirement strategy while maintaining a modest lifestyle wealth approach. Whether your plan includes real estate investing Canada, real estate vs renting decisions, legacy planning Canada, estate planning Canada, or building long-term wealth Canada, the key is financial vision setting and creating financial systems for entrepreneurs that protect flexibility, improve tax efficiency, and support sustainable wealth building strategies Canada.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs saving 10% of your income really enough to create financial freedom and set you up for a comfortable retirement—or could that “responsible” rule leave you short?Most people have heard the classic advice: pay yourself first, stay disciplined, and invest 10% of what you earn. But when you factor in inflation, lifestyle costs, taxes, time horizon, and the difference between gross and net income, that simple rule starts to look a lot less certain. In this episode, Kyle Pearce and Jon Orr unpack what actually happens when you follow the 10% rule over 10, 20, or 30 years—and why your personal retirement number may require a much more intentional plan.You'll walk away with:A clearer understanding of why saving 10% may not replace enough of your future income.A practical way to think about savings rates, inflation, investment returns, and retirement timelines.A better sense of how your current spending and investing habits affect how soon you can become financially free.Press play now to find out whether your savings rate is truly aligned with the financial freedom you want.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadians pursuing financial independence, the real question is whether your savings rate and retirement planning strategy can actually support the lifestyle you want after work. While the traditional 10% rule is often presented as a simple personal finance starting point, factors like inflation, compound interest, investment returns, taxes, and time horizon can dramatically affect your retirement savings and path to financial freedom Canada. A stronger Canadian wealth plan may include tax-efficient investing, RRSP optimization, optimizing RRSP room, investment bucket strategy, financial buckets, passive income planning, and smart investment strategies tailored to your income, lifestyle, and goals. For incorporated professionals and entrepreneurs, this can also involve corporate wealth planning, personal vs corporate tax planning, salary vs dividends Canada, corporation investment strategies, corporate structure optimization, and business owner tax savings. Building long-term wealth Canada may also require evaluating real estate investing Canada, real estate vs renting, financial diversification Canada, capital gains strategy, estate planning Canada, legacy planning Canada, and financial systems for entrepreneurs. Whether your goal is an early retirement strategy, modest lifestyle wealth, or a broader vision for financial independence Canada, the key is using practical retirement planning tools, clear financial vision setting, and intentional wealth building strategies Canada to create a plan that supports lasting financial freedom.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Thanks to Surfshark for sponsoring the show. Go to https://surfshark.com/stackingb or use code STACKINGB at checkout to get 4 extra months of Surfshark VPN!Isaac Newton was one of the smartest humans who ever lived. He also bought into the South Sea Bubble, sold for a profit, watched it keep climbing, bought back in out of pure FOMO, and rode it all the way down to an 80% loss that haunted him until he died. Ben Carlson, co-host of the Animal Spirits podcast and one of the sharpest minds at Ritholtz Wealth Management, joins Joe and Anna to walk through centuries of market history -- bubbles, crashes, and the psychology that makes smart people do dumb things with money. Anna also helps a Stacker named Louie untangle his 401(k) sources and figure out whether it's finally time to bring in a professional.What You'll Walk Away WithWhy Isaac Newton's South Sea Bubble loss still ranks among history's most instructive investing failures -- and why it had nothing to do with intelligenceBen's framework for why risk means something completely different depending on where you are in your life cycle -- and why a market crash genuinely doesn't matter the same way to a 25-year-old and a 55-year-oldThe wrong lesson an entire generation learned from 2008 -- and why everyone preparing for the last crisis missed the next seventeen years of bull marketWhy Japan's three-decade stock market bubble is the best real-world case for diversification -- and why it doesn't translate as cleanly to the US as people assumeThe behavioral reason complex investment strategies are easy to sell and nearly impossible to hold through a downturn -- while simple strategies survive the painWhy Ben's firm discovered that the hardest financial transition isn't saving for retirement -- it's actually learning to spend the money once you get thereThe Beanie Babies divorce court story that perfectly captures what every bubble looks like from the outsideAnna and OG's take on Louie's four-source 401(k): why it's simpler to manage than it looks, and why "move everything to Roth" is the wrong instinct for most DIY investorsThe Roth conversion icing-on-the-cake strategy: how to use pre-tax and Roth buckets together to manage your tax bracket year by year in retirementWhy one financial pro has a surprisingly negative take on HSAs at death -- and the timing problem that makes spending one down in retirement genuinely trickyWhy This Matters NowEvery market cycle feels unprecedented while you're living through it. Understanding the actual constant -- human psychology, not headlines -- is the difference between riding out volatility and becoming a cautionary tale, smart as you might be.From the BasementBen Carlson joins Joe and Anna to walk through centuries of bubbles, crashes, and the psychological wiring that makes both geniuses and ordinary investors do the same dumb things. Doug arrives with Statue of Liberty trivia tied to America's upcoming 250th anniversary. A Stacker calling himself Louie -- and getting Anna instead of OG, much to his surprise -- asks for help simplifying his 401(k) and figuring out his Roth conversion strategy, and gets a reminder that he's already doing better than he thinks.Resources MentionedRisk and Reward: How to Handle Market Volatility and Build Long-Term Wealth by Ben Carlson -- available wherever books are soldAnimal Spirits podcast -- Ben Carlson and Michael Batnick; available wherever you listen to podcastsRitholtz Wealth Management -- referenced for prior guests Barry Ritholtz, Josh Brown, and Nick MaggiulliWhere Are the Customers' Yachts? by Fred Schwed -- referenced for the famous quote on the emotional experience of losing moneyPaul Merriman's research on asset allocation -- paulmerriman.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins voicemail line -- stackingbenjamins.com/yelldownstairsStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre IPPs and PPPs actually the right next step for your corporate wealth strategy—or just more complexity than you need?As your incorporated business grows, your planning priorities start to shift from simply reinvesting and reducing tax today to building a more structured long-term retirement and legacy strategy. Individual Pension Plans and Personal Pension Plans can offer powerful tax-deferred planning opportunities, but they only work well when your income, age, corporate structure, and future goals line up. This episode helps you understand when these plans make sense—and when simpler strategies may still be the better fit.You'll walk away with:A clear understanding of how IPPs and PPPs differ from RRSPs, including how contributions are calculated and why these plans are more than just “bigger RRSPs.”A practical sense of timing, including why these strategies often become more attractive in your late 40s, 50s, and beyond rather than during the earlier growth years of your business.Insight into the trade-offs between predictability and flexibility, including how IPPs and PPPs compare on cost, complexity, contribution options, tax deferral, and family business succession planning.Press play now to learn whether an IPP or PPP could fit your next stage of corporate wealth planning.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.A strong Canadian wealth plan for incorporated business owners should connect corporate wealth planning, personal vs corporate tax planning, RRSP optimization, salary vs dividends Canada, and corporation investment strategies into one clear system for building long-term wealth Canada. For Canadian entrepreneurs, the path to financial freedom Canada and financial independence Canada often involves choosing the right retirement planning tools, such as an Individual Pension Plan, Personal Pension Plan, or other RRSP alternatives Canada, while also considering tax-efficient investing, corporate tax deferral, business owner tax savings, passive income planning, and corporate structure optimization. Whether your strategy includes real estate investing Canada, real estate vs renting, a capital gains strategy, financial buckets, an investment bucket strategy, or financial diversification Canada, the key is aligning your financial vision setting with practical Canadian tax strategies, estate planning Canada, legacy planning Canada, and business owner succession planning. By optimizing RRSP room, managing retained earnings, and creating financial systems for entrepreneurs, incorporated professionals can build a flexible early retirement strategy, support a modest lifestyle wealth goal, and create a stronger foundation for retirement planning for entrepreneurs, long-term tax deferral, and lasting family wealth.Ready to connect? Text us your comment including your phone number for a response! If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Get our Investment Guide: https://clickhubspot.com/klsr Episode 832: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to legendary fund manager Barry Ritholtz( https://x.com/Ritholtz ) about the behaviors that destroy returns for investors and how to avoid them.  — Show Notes:  (0:00) Intro (2:19) christmas tree portfolio (4:43) the cowboy account (9:51) day trading (11:09) Barry yells at Lloyd Blankfein (13:46) panic selling (16:45) sam picks a fight (18:46) direct indexing (21:43) Great investors  (27:25) 90% of everything is crap (36:14) Elon's foray into PE (44:02) Predicting the housing crisis (46:01) spending a year as the dumbest guy on wall street (49:01) Why bubbles are good for the economy — Links: • How Not To Invest - https://www.hownottoinvestbook.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs leverage really the risky part of wealth building — or is the bigger risk misunderstanding how, when, and why to use it?Many Canadian business owners and investors already use leverage every day through mortgages, vehicle financing, business debt, or lines of credit — yet borrowing to invest often feels like a completely different level of risk. In this episode, Kyle and Jon unpack why some forms of debt feel “normal” while others feel dangerous, and how education, experience, asset choice, and the right support can dramatically change how risk is perceived. If you've ever wondered whether leveraged investing is smart strategy or unnecessary danger, this conversation will help you think more clearly about the difference.You'll walk away with:A clearer way to compare “acceptable” debt, like mortgages, with investment leverage that may create income or tax advantages.A practical lens for understanding objective risk versus perceived risk — and why your experience with an asset class matters.A better sense of when leverage may be an opportunity, when it may be a red flag, and why guidance or deeper education can help reduce costly mistakes.Press play now to rethink leverage, risk, and opportunity through a more strategic wealth-building lens.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs and investors, building long-term wealth Canada starts with a clear Canadian wealth plan that connects leverage, risk management, investment strategies, financial education, and tax optimization into one intentional system. Whether you are comparing real estate investing Canada with real estate vs renting, exploring passive income planning, optimizing RRSP room, or weighing salary vs dividends Canada, the goal is to use smart financial planning, personal vs corporate tax planning, and corporation investment strategies to reduce investment risk while creating more financial freedom Canada. A strong plan may include RRSP optimization, tax-efficient investing, Canadian tax strategies, capital gains strategy, corporate wealth planning, business owner tax savings, corporate structure optimization, and financial systems for entrepreneurs, all supported by retirement planning tools, financial buckets, an investment bucket strategy, and financial vision setting. By focusing on financial diversification Canada, modest lifestyle wealth, early retirement strategy, passive income, estate planning Canada, legacy planning Canada, and financial independence Canada, Canadians can create wealth building strategies Canada that balance real estate, corporate assets, tax planning, and long-term investment risk management.Ready to connect? Text us your comment including your phone number for a response! If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs Ontario's small business tax cut actually saving you money—or just shifting the tax bill somewhere else?A lower corporate income tax rate sounds like a win for business owners, especially when headlines make the cut look dramatic. But if you eventually need to pull retained earnings out of your corporation, the personal tax side matters just as much as the corporate savings. This episode breaks down what the change really means, why the “savings” may not be as generous as they appear, and how business owners should think more strategically about salary, dividends, and retained earnings.You'll walk away with:A clearer understanding of how Ontario's small business tax cut affects active corporate income.The round-trip math behind saving tax inside the corporation versus paying more when dividends come out personally.Key planning questions to consider around retained earnings, passive income, salary, dividends, and long-term tax efficiency.Press play now to understand whether this tax change helps your business—or quietly creates a bigger planning problem down the road.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.For Canadian entrepreneurs, building a strong Canadian wealth plan starts with understanding how small business taxin Ontario, a corporate tax cut, dividend tax, and personal vs corporate tax planning can impact long-term decisions around tax planning, business strategy, and wealth management. Whether your goal is financial freedom Canada, financial independence Canada, or an early retirement strategy, the right approach may include corporate wealth planning, salary vs dividends Canada, RRSP optimization, optimizing RRSP room, tax-efficient investing, passive income planning, and smart corporation investment strategies. For business owners pursuing modest lifestyle wealth, legacy planning Canada, and building long-term wealth Canada, it's important to align financial buckets, an investment bucket strategy, financial vision setting, retirement planning tools, and financial systems for entrepreneurs with practical Canadian tax strategies, business owner tax savings, capital gains strategy, and corporate structure optimization. From real estate investing Canada and real estate vs renting to financial diversification Canada, passive income, and estate planning Canada, the best wealth building strategies Canadahelp connect today's cash flow decisions with tomorrow's freedom, security, and family legacy.Ready to connect? Text us your comment including your phone number for a response! If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre your corporate retained earnings really worth what you think they are once they finally reach your family's hands?If you've built up cash inside your corporation or holding company, it can feel like that money is fully part of your net worth. But once passive income taxes, dividend taxes, and the small business deduction grind come into play, the number on paper can look very different from what actually lands in your personal pocket. This episode helps incorporated business owners rethink retained earnings not just as “money in the corporation,” but as dollars that need a smart path to eventually reach human hands.You'll walk away with:A clearer understanding of why passive income inside a corporation can trigger heavy tax drag and reduce access to the small business tax rate.A practical way to compare income-producing investments versus capital-appreciating assets inside a corporate structure.Insight into how strategies like the capital dividend account and corporate-owned life insurance may support tax-efficient cash flow, legacy planning, and long-term wealth transfer.Press play now to learn how to think more strategically about retained earnings, corporate investing, and getting more of your business wealth into your family's hands.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.A strong Canadian wealth plan for incorporated business owners starts with understanding corporate retained earnings Canada, retained earnings tax, and the difference between personal vs corporate tax planning so you can make smarter decisions around salary vs dividends Canada, RRSP optimization, optimizing RRSP room, and long-term corporate wealth planning. For Canadian entrepreneur finance, the goal is often financial freedom Canada, financial independence Canada, or an early retirement strategy built around modest lifestyle wealth, financial buckets, an investment bucket strategy, and practical retirement planning tools. Whether you are comparing real estate investing Canada, real estate vs renting, holding company investments, or other corporation investment strategies, the right approach should consider passive income corporation Canada, passive income planning, the small business deduction grind, capital gains strategy, the capital dividend account, corporate-owned life insurance, and broader Canadian tax strategies. With thoughtful corporate structure optimization, tax-efficient investing, business owner tax savings, financial systems for entrepreneurs, and financial diversification Canada, Canadian business owners can create stronger wealth building strategies Canada, support building long-term wealth Canada, clarify their financial vision setting, and strengthen legacy planning Canada and estate planning Canada through a more intentional corporate wealth strategy.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

On episode 223 of Ask The Compound, Ben Carlson and Duncan Hill discuss: energy stocks vs. the S&P 500, building the perfect portfolio, overcoming the fear of investing aggressively when you're young, whether it's worth sacrificing passion for higher pay, when retirees should finally add bonds, target-date funds vs. index funds in marriage, and whether today's AI-driven market feels more like smart investing or dot-com bubble euphoria. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!  Order your copy of Ben's book, 'Risk and Reward' here: https://lnk.to/riskandrewardbook This episode is sponsored by Public. Find out more at https://public.com/ATC Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you chasing a tax-saving strategy that sounds smart—but may not be the biggest financial opportunity in front of you?In this episode, Jon Orr and Kyle Pearce unpack a real-world Canadian wealth planning scenario involving rental properties, cash damming, the Smith Manoeuvre, a primary residence mortgage, and retained earnings inside a corporation. While strategies like cash damming can create tax-deductible interest, the episode challenges listeners to step back and ask whether the time, complexity, and bookkeeping are actually worth the payoff right now. For business owners and real estate investors, the bigger win may come from identifying the highest-impact planning opportunity before getting lost in the weeds of smaller optimizations.You'll walk away with:A clearer understanding of how cash damming fits within the Smith Manoeuvre and why the purpose of borrowed funds matters.A practical way to think through whether a tax deduction is meaningful enough to justify the effort.A reminder to compare small tax-saving moves against larger planning opportunities, especially when corporate retained earnings and future tax exposure are involved.Press play now to learn how to spot the difference between a clever financial tactic and the strategy that may matter most.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets sit in low interest earning savings accounts;…investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting corporate passive income taxes at greater than 50%; or,…wondering whether your current corporate wealth management strategy is optimal for your specific situation.Cash Damming and the Smith Manoeuvre are popular Canadian tax strategies, but the real question for Canadian investors, entrepreneurs, and business owners is whether these moves fit into a bigger Canadian wealth plan. In this episode of Canadian Wealth Secrets, we explore how Tax Planning Canada, Rental Properties, HELOC Strategy, and Canadian Real Estate Investing can work together with Corporate Wealth Planning, Retained Earnings, and Business Owner Tax Strategy to support long-term goals like financial freedom Canada, early retirement strategy, passive income planning, and financial independence Canada. For incorporated professionals, the conversation goes beyond real estate investing Canada and looks at salary vs dividends Canada, personal vs corporate tax planning, corporation investment strategies, corporate structure optimization, business owner tax savings, and tax-efficient investing. You'll also hear why modest lifestyle wealth, RRSP optimization, optimizing RRSP room, financial buckets, investment bucket strategy, capital gains strategy, estate planning Canada, legacy planning Canada, and financial vision setting all matter when building long-term wealth Canada. Whether you're comparing real estate vs renting, planning for retirement, exploring retirement planning tools, improving financial systems for entrepreneurs, or seeking better financial diversification Canada, this episode helps you focus on wealth building strategies Canada that align with your lifestyle, tax situation, and future goals.Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereCould your RRSP become one of your biggest future tax problems—and is there a smarter way to unwind it?Many Canadians spend decades building RRSP wealth, only to discover later that RRIF withdrawals can trigger a much larger tax bill than expected. This episode breaks down why the real issue is not the RRSP itself, but the lack of a coordinated system for withdrawals, deductions, leverage, and retirement cash flow. You'll hear how tax-efficient planning can begin well before retirement, especially for high-income Canadians, incorporated business owners, and anyone trying to preserve more of what they've built. In this episode, you'll learn:How RRSPs and RRIFs really differ—and why converting strategically can create more control over income, liquidity, and tax timing.What a true RRIF meltdown strategy involves, including how investment loan interest deductions can help offset taxable RRIF income.How self-made dividends and capital gains planning can support retirement cash flow while reducing reliance on fully taxable income sources.Press play now to learn how a more intentional RRSP and RRIF strategy could help you reduce future tax drag and create more flexibility in retirement.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to Kyle if you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large sum of liquid assets Ready to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

My Conversation with Barry starts at about 30 minutes Subscribe and Watch Interviews LIVE : On YOUTUBE.com/StandUpWithPete ON SubstackStandUpWithPete Stand Up is a daily podcast. I book,host,edit, post and promote new episodes with brilliant guests every day. This show is Ad free and fully supported by listeners like you! Please subscribe now for as little as 5$ and gain access to a community of over 750 awesome, curious, kind, funny, brilliant, generous soul Subscribe and Watch Interviews LIVE : On YOUTUBE.com/StandUpWithPete ON SubstackStandUpWithPete Stand Up is a daily podcast. I book,host,edit, post and promote new episodes with brilliant guests every day. This show is Ad free and fully supported by listeners like you! Please subscribe now for as little as 5$ and gain access to a community of over 750 awesome, curious, kind, funny, brilliant, generous soul How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them The GREAT Barry Ritholtz who has spent his career helping people spot their own investment errors and to learn how to better manage their own financial behaviors. He is the creator of The Big Picture, often ranked as the number one financial blog to follow by The Wall Street Journal, New York Times, and others. Barry Ritholtz is the creator and host of Bloomberg's "Masters in Business" radio podcast, and a featured columnist at the Washington Post. He is the author of the Bailout Nation: How Greed and Easy Money Corrupted Wall Street and Shook the World Economy (Wiley, 2009). In addition to serving as Chairman and Chief Investment Officer of Ritholtz Wealth Management, he is also on the advisory boards of Riskalyze, and Peer Street, two leading financial technology startups bringing transparency and analytics to the investment business. Barry has named one of the "15 Most Important Economic Journalists" in the United States, and has been called one of The 25 Most Dangerous People in Financial Media. When not working, he can be found with his wife and their two dogs on the north shore of Long Island. Listen rate and review on Apple Podcasts Listen rate and review on Spotify Pete On Instagram Pete on Blue Sky Pete on Threads Pete on Tik Tok Pete on Twitter Pete Personal FB page Stand Up with Pete FB page Gift a Subscription https://www.patreon.com/PeteDominick/gift Send Pete $ Directly on Venmo All things Jon Carroll Buy Ava's Art Subscribe to Piano Tuner Paul Paul Wesley on Substack Listen to Barry and Abigail Hummel Podcast Listen to Matty C Podcast and Substack Follow and Support Pete Coe Hire DJ Monzyk to build your website or help you with Marketing

On episode 221 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Ritholtz CIO Barry Ritholtz to discuss: debt, finding money happiness, how to invest $100k cash, when to sell intel, single stocks and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!  Today's show is sponsored by Public. Find out more at https://public.com/ATC Barry's book out in paperback: https://ritholtz.com/2026/05/how-not-to-invest-paperback-arrives/ Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you spending your best time chasing small financial gains while your biggest opportunity is sitting right in front of you?In this episode, Jon Orr unpacks a simple but powerful question every business owner and investor needs to ask: are the inputs required to reach a goal actually worth the output? Through stories about kite surfing, marathon running, poker, and portfolio management, he explores how easy it is to confuse “I could do this” with “I should do this.”For entrepreneurs especially, the real tension is often between actively growing the business and spending countless hours trying to optimize passive investments. Sometimes the smartest move is not doing more—it is choosing where your time creates the greatest return.You'll walk away with:A clearer way to evaluate whether a goal is worth the time, energy, and commitment it requires.A practical lens for deciding whether your “alpha” comes from your investment portfolio or your active business.Permission to let passive assets stay passive so you can focus on the areas where your effort creates the biggest payoff.Press play now to rethink where your time is going—and whether the trade-off is truly worth it.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat if your investment results have less to do with what you own—and more to do with who you become when markets get uncomfortable?Most investors are taught to focus on picking the right stocks, funds, timing, or asset mix. But the real difference-maker is often behavior: how you react to uncertainty, losses, control, and fear. In this episode, you'll explore why two people can hold the same portfolio and still end up with very different outcomes—because their investor personality shapes the decisions they make along the way.You'll walk away with:A clearer understanding of the five investor personality types: the set-it-and-forget-it optimizer, skeptical controller, emotional reactor, confident operator, and security seeker.Insight into how loss aversion, overconfidence, and the urge for certainty can quietly influence your financial decisions.A better way to think about building an investment strategy that fits your real behavior—not just your risk questionnaire score.Press play now to discover which investor personality patterns show up in your financial life—and how to build a strategy you can actually stick with.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat if your retirement plan depends on selling the very assets you spent decades building?For many business owners and high-net-worth Canadians, “financial freedom” often means reaching a number on paper—but what happens when that number has to be slowly drawn down to fund your lifestyle? This episode challenges the traditional retirement mindset of accumulating a pile of assets, then hoping it lasts long enough. Instead, Jon Orr and Kyle Pearce explore how to think about income, diversification, and portfolio structure in a way that can support more confidence, flexibility, and peace of mind in your financial freedom years.You'll walk away with:A clearer understanding of why relying only on asset sales can feel emotionally risky when funding retirement.A fresh way to think about diversifying not just by asset class, but by strategy and structure for retirement.Insight into how income-focused investing can help create cash flow without constantly shrinking your principal when designing retirement.Press play now to rethink how your portfolio could support your lifestyle without forcing you to sell off the assets you worked so hard to build.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat happens if your main income engine slows down before your backup plan is even moving?If you're building a business, growing retained earnings, or counting on a future exit to fund your freedom, this episode is a timely reality check. Jon Orr and Kyle Pearce unpack why so many Canadian entrepreneurs pour everything into one flywheel—the business or job that funds life today—while neglecting the second flywheel that's supposed to protect them later. This conversation speaks directly to anyone who wants more stability, more options, and less financial stress when business gets unpredictable.In this episode, you'll hear how to:think about wealth in terms of two flywheels: your active income engine and your passive income enginestop relying on a future business sale as the only path to long-term freedomstart building a second flywheel early by allocating profits strategically between safe, liquid assets and longer-term growth assetsPress play now to learn how to build financial momentum that keeps working, even when your first flywheel hits turbulence.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWant to turn corporate retained earnings into future tax-efficient cash flow without locking your money away?If you are a business owner sitting on retained earnings, you have probably felt the tension between paying personal tax now or leaving money in the corporation and dealing with the tax consequences later. This episode walks through a strategy designed to create more flexibility: using a corporate-owned permanent life insurance policy as a pass-through structure that can support borrowing, asset growth, and long-term estate planning. It is especially relevant if you want more optionality with your money while keeping an eye on taxes, liquidity, and legacy.In this episode, you'll learn how to:Understand how a corporate-owned permanent life insurance policy can help reduce future personal tax friction on retained earnings.See what funding levels like $1 million per year versus $100,000 per year can actually look like in practice, including cash value growth, leverage potential, and policy offset options.Grasp how this structure can support both living benefits now and estate planning advantages later through growing cash value, borrowing flexibility, and tax-efficient death benefit planning.Press play now to see how this strategy can create more control, more flexibility, and a more tax-efficient path for your corporate wealth.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat would it actually take to make work optional by age 50?As a Canadian business owner or investor, If you have a good income, some investments, and a rough number in mind for “financial freedom,” it is easy to assume you are on the right track to financial freedom without ever testing the math. But there is a big difference between a financial goal that sounds safe and a goal that truly fits the life you want. This episode helps you cut through the guesswork so you can stop chasing arbitrary numbers and start building a financial plan that matches your timeline, spending, and priorities.In this episode, you'll learn how to:figure out whether your financial freedom number actually covers the lifestyle you want in the futurereverse-engineer your financial target based on spending, inflation, rate of return, and time horizonseparate your minimum financial goal from your stretch goal so you can grow wealth without losing sight of what matters mostPress play now to build a clearer, more realistic path toward financial freedom without sacrificing the life you want along the way.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWant a smarter way to use corporate retained earnings without triggering a massive personal tax hit?If you're a successful incorporated business owner in Canada, you've probably felt the tension between leaving profits trapped in the corporation or pulling them out and losing a huge chunk to tax. This episode explores a different path: using a permanent insurance policy as a strategic pass-through structure so your money can keep working, give you more flexibility, and support both current cash-flow goals and long-term planning.In this episode, you'll learn how to:Turn retained earnings into a tax-efficient asset that can grow inside your corporate structure instead of sitting in taxable passive investments.Create a strategy where the same dollars can support future investing opportunities through leverage, helping your money work in more than one place at once.Build in long-term upside through tax-free death benefit planning and greater flexibility for personal cash flow, estate planning, and eventual extraction strategies.Press play to hear how this corporate strategy can help you keep more of what you've built while expanding your options for the future.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you spending too much time trying to optimize your money instead of making the moves that actually build wealth?This episode is for the Canadian business owner who wants to be smarter with taxes, investing, and long-term planning—but also knows how easy it is to get stuck in analysis. Hosts, Jon Orr and Kyle Pearce unpack a powerful mindset shift for the year ahead: stop chasing every tiny optimization and focus on the habits and decisions that create real momentum. If you have ever wondered whether your financial strategy is actually helping—or just distracting you—this conversation will hit home.You'll hear how to create one simple, repeatable money habit that can quietly build wealth over time.You'll learn why increasing income and protecting your focus can matter more than endlessly tweaking tax and investment decisions.You'll also get a practical lens for deciding when to keep managing things yourself and when it may be smarter to systematize or delegate.Press play now to reset your financial focus for the next year and make the moves that matter most.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you building a business you can actually step away from—or just creating a job that depends on you forever?If you're a Canadian incorporated business owner thinking about retirement, succession, or a possible exit, this episode digs into the messy middle most people face. What happens when your business creates strong income, but only because you are still carrying so much of the load? You'll hear a real-world discussion about how to start shifting from being the engine of the business to building something more sustainable, valuable, and flexible for your next chapter.In this episode, you'll learn how to:think more clearly about whether your best move is to sell, stay, or gradually step backincrease the value of a business by making it less owner-dependent and more self-sustainingexplore practical transition options like hiring the right operator, profit sharing, and phased ownership over timePress play to hear a smarter way to prepare your business for freedom, flexibility, and a more confident exit.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs paying 1% for investment management a waste of money—or the exact support that could protect your wealth?If you've ever wondered whether you should keep investing on your own or hand the reins to an advisor, this episode gets right to the heart of that tension. It speaks to the very real struggle between wanting to minimize fees and wanting more confidence, better decision-making, and less stress when markets get shaky. Whether you're early in your investing journey or getting closer to financial freedom, this conversation helps you think beyond simple math and make a choice that actually fits how you operate.You'll walk away with:A clearer way to decide whether DIY investing or professional management fits your personality, habits, and goalsA better understanding of what you're really paying for with a 1% fee, including coaching, accountability, peace of mind, and complexity managementA practical lens for comparing options using time, behavior, and risk-adjusted returns—not just headline performance numbersPress play now to figure out whether paying for investment management is costing you too much—or saving you from bigger mistakes.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereWhat do you do when you've built more wealth than you need—but your success is quietly setting up a massive future tax bill?This episode walks through a real planning scenario that will hit home for many Canadian business owners, entrepreneurs, and investors. You'll hear how one retired entrepreneur did almost everything right—paid off the house, built strong investment buckets, and created lasting financial security—yet still ended up with hidden tax inefficiencies inside a RRIF, personal accounts, and a holding company. If you've ever wondered whether your current structure could create unnecessary drag later, this conversation shows where those problems come from and what can still be done to improve them.You'll learn:How large RRIF balances can create a growing tax problem in retirement, even when you do not need the income.Why asset location matters—especially when comparing TFSAs, non-registered GICs, and corporate investments.How strategies like leveraged investing and corporate-owned whole life insurance may help reduce tax drag, improve estate efficiency, and create more flexibility for future withdrawals.Press play to hear how a “good problem to have” can become a smarter, more tax-efficient wealth plan. Built from your uploaded transcript.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre market drawdowns making you question your retirement plan—or tempting you to panic when your portfolio drops?When markets pull back, it is easy to feel like everything is suddenly at risk—especially if retirement is getting closer or you are finally starting to build real momentum with your money. This episode digs into the emotional side of investing during uncertain times and shows why drawdowns feel very different depending on your timeline, income needs, and overall strategy. Whether you are a business owner, a salaried employee, or someone trying to make smarter wealth decisions, this conversation helps you think more clearly when volatility hits.In this episode, you'll hear how to:understand the real “cost of admission” that comes with investing in growth assets like index fundstell the difference between risk tolerance and risk capacity so your plan actually matches your stage of lifecreate simple rules and strategies for handling market pullbacks without making emotional decisions you regretPress play now to learn how to stay calm, stay strategic, and make better financial decisions when the market gets shaky.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you really diversified—or just following one investing strategy and hoping it works out?In this episode, we unpack what The Psychology of Money gets wrong about portfolio diversification and why many investors misunderstand what diversification actually means. While many popular investing books recommend keeping things simple with a single strategy, real-world investing often requires more flexibility.If you've ever felt torn between keeping your portfolio simple and optimizing for better results, this conversation will resonate. We explore why building wealth is not just about choosing the “best” asset class, but about choosing a strategy you can actually stick with through market swings, uncertainty, and changing goals.You'll hear a candid discussion about the emotional side of investing, the tension between growth and income, and why true diversification may involve more than just owning different assets—it may require diversifying strategies as well.In this episode, you'll learn:Why diversification is not only about asset classes, but also about investment strategies—and how that shift can change the way you build wealth.How to choose an investing approach that matches your personality, risk tolerance, and long-term goals so you can stay consistent.Why balancing net worth growth, cash flow, and flexibility can help you create more optionality as your financial life evolves.Press play to rethink diversification and start building a wealth strategy you can actually feel confident following.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre dividends really the smartest way to pay yourself from your corporation—or could they be quietly costing you more over time?If you're an incorporated Canadian business owner, chances are you've heard that dividends are the more tax-efficient option. But that idea can be misleading when you look at the full picture. This episode breaks down why the real decision isn't just about this year's tax bill—it's about RRSP room, CPP, corporate tax thresholds, investment discipline, and building a better long-term wealth strategy.You'll learn:Why the “dividends save tax” belief is mostly an illusion once you understand tax integration.When salary becomes the stronger move, especially as corporate income rises above key thresholds like $500,000.The practical income benchmarks that can help you decide when to use salary, dividends, or a blend of both.Press play to find out how to pay yourself more strategically—and stop leaving money on the table.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you really financially free if your net worth is locked in real estate but your cash flow still feels tight?This episode is for the investor who looks strong on paper but still feels uncertain about retirement. If you've built wealth through property, kept buying, refinancing, and growing equity, but haven't created reliable income, this conversation will hit home. Kyle and Jon unpack the uncomfortable gap between being asset rich and actually having the freedom to live confidently from your money.You'll hear how real estate can be an incredible wealth-building tool while still falling short as a standalone retirement income strategy.You'll learn why chasing equity growth alone can leave you stressed, overleveraged, and unclear on your next move as retirement gets closer.You'll walk away with a clearer way to think about diversification, liquidity, and building dependable income alongside your net worth.Press play now to rethink whether your portfolio is truly built for retirement—or just built to look good on paper.

Join us in Vegas for Podjam 3! Barry Ritholtz 31 minutes Jonathan Miller 1:28 Colby Hall 2:42  Subscribe and Watch Interviews LIVE : On YOUTUBE.com/StandUpWithPete ON SubstackStandUpWithPete Stand Up is a daily podcast. I book,host,edit, post and promote new episodes with brilliant guests every day. This show is Ad free and fully supported by listeners like you! Please subscribe now for as little as 5$ and gain access to a community of over 750 awesome, curious, kind, funny, brilliant, generous souls How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them  The GREAT Barry Ritholtz who has spent his career helping people spot their own investment errors and to learn how to better manage their own financial behaviors. He is the creator of The Big Picture, often ranked as the number one financial blog to follow by The Wall Street Journal, New York Times, and others. Barry Ritholtz is the creator and host of Bloomberg's "Masters in Business" radio podcast, and a featured columnist at the Washington Post. He is the author of the Bailout Nation: How Greed and Easy Money Corrupted Wall Street and Shook the World Economy (Wiley, 2009). In addition to serving as Chairman and Chief Investment Officer of Ritholtz Wealth Management, he is also on the advisory boards of Riskalyze, and Peer Street, two leading financial technology startups bringing transparency and analytics to the investment business.  Barry has named one of the "15 Most Important Economic Journalists" in the United States, and has been called one of The 25 Most Dangerous People in Financial Media. When not working, he can be found with his wife and their two dogs on the north shore of Long Island. Jonathan Miller is the Director of Markets for StreetMatrix, a real-time home price index series used by the financial services sector to track local, regional, and national housing markets in the United States. I'm also the President and CEO of Miller Samuel Inc., a real estate appraisal and consulting firm I co-founded in 1986. For 32 years, I authored a series of market reports for Douglas Elliman Real Estate, considered the "report of record," which accounted for 50% of their media coverage. My market reports analyzed the New York City metropolitan area, Boston, parts of Florida, California, Texas, Connecticut, and Colorado that were relied on by the media, financial institutions, and government agencies, including the Federal Reserve, Internal Revenue Service, U.S. Department of Housing and Urban Development, the NYC Office of Management and Budget, and others. I am an Adjunct Associate Professor of Architecture, Planning, and Preservation in the Master of Science in Real Estate Development (MSRED) Program at Columbia University, where I teach market analysis. I've guest lectured at institutions including New York University, Harvard University, The Wharton School of the University of Pennsylvania, Columbia University, and Drexel University, and am also a New York State Real Estate Instructor for qualifying and continuing education courses and a New York State Real Estate Appraiser Instructor for qualifying certified general and continuing education courses. I co-authored a research paper for NYU School of Law and the NYU Wagner Graduate School of Public Service's Furman Center for Real Estate and Urban Policy titled The Condominium v. Cooperative Puzzle: An Empirical Analysis of Housing in New York City, published in 2007 by the Journal of Legal Studies at the University of Chicago. Back in 2010, I developed pending home sale indices for the Washington, D.C., and Baltimore metro areas, and Central Pennsylvania, on behalf of Bright MLS, one of the largest multiple listing services in the U.S. One of my favorite activities is serving on the New York City Mayor's Economic Advisory Panel, representing the residential real estate sector, and the New York State Budget Division Economic Advisory Board. I've also participated in valuation studies with academic institutions, including New York University, Princeton University, Columbia University, and Baruch College. I participated in and co-authored an epic research paper as part of the Urban Land Institute Advisory Services for the city of Norfolk, VA (its flooding problems are getting worse). I also authored a white paper for One Fine Stay, a hospitality brand owned by AccorHotels, titled "The Future of Luxury New Development in New York: Leaving $1 Billion on the Table." In the valuation world, I am a state-certified real estate appraiser in New York and Connecticut, and I provide expert witness testimony in various local, state, and federal courts. I hold the Counselors of Real Estate (CRE) designation. I am also an Appraiser "A" Member of the Real Estate Board of New York and a former two-term President of RAC, a premier appraisal organization whose members focus on complex residential properties for relocation, litigation support, testimony, and reviews. As a result of my extensive writing and investigative research on this Housing Notes platform, I brought public attention to the misconduct of two key institutions in the appraisal profession: The Appraisal Foundation and The Appraisal Institute. As a result, I became an expert witness for the Appraisal Subcommittee at FHFA in Washington, DC, which aired for three hours on C-SPAN in 2023. One memorable thing that came out of my appearance was the birth of my fourth grandchild during the session. On the personal side, I'm clearly a homebody and love hanging out with my wife, whom I met in college in 1980, greasing donut trays at 5:30 am at the student bakery, a part of the second-largest non-military cafeteria in the world, located at Michigan State University. There is nothing better than when any of our four sons and their significant others, including the grandchildren, are in town. For our fortieth wedding anniversary, my wife and I went to Antarctica (perhaps I'm not a homebody?) While I'm at it, a couple of formative childhood adventures: At 12 years old, I climbed to the snow line of Mt. Kilimanjaro (leadership said I was too young to summit - boo!) In middle school, I traveled to the Soviet Union on a study abroad program before the wall fell. When I was a teenager and before I got my driver's license, I rode my bicycle from Oregon to Virginia in the summer of 1976, carrying all my gear (my parents claim they gave me a one-way airplane ticket to fly across the US, and I came back!) At age 25, I co-founded Miller Samuel because I didn't know any better. In my offline hours, I love to read, explore new music, try to make snow, attempt to catch lobsters, and endeavor to connect to my backyard birdhouse camera from whatever airplane I happen to be flying on. Contact Jonathan Colby Hall is the Founding Editor of Mediaite.com. He is also a Peabody Award-winning television producer of non-fiction narrative programming, became a media contributor to NewsNation in March of 2023. He is also  a former Creative Director who launched iHeartRadio's original video offering. Check out his pieces at Mediaite    On YOUTUBE.com/StandUpWithPete ON SubstackStandUpWithPete   Listen rate and review on Apple Podcasts Listen rate and review on Spotify Pete On Instagram Pete on Blue Sky Pete on Threads Pete on Tik Tok Pete on Twitter Pete Personal FB page Stand Up with Pete FB page Gift a Subscription https://www.patreon.com/PeteDominick/gift Send Pete $ Directly on Venmo

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you building wealth in the right order—or accidentally delaying the very foundation that makes bigger opportunities possible?If you're a business owner sitting on retained earnings, it's easy to treat every new opportunity like the priority—especially when real estate, acquisitions, or other growth plays look exciting. But this episode challenges a costly assumption: that a corporate wealth reservoir has to wait until after the next deal. Instead, it reframes that reservoir as the infrastructure that helps you pursue future opportunities with more control, liquidity, and long-term efficiency.In this episode, you'll hear how to:Rethink corporate-owned whole life insurance as foundational wealth infrastructure—not as a competing investment.Avoid the sequencing mistake that can quietly cost you years of compounding.Build a smarter capital strategy that supports liquidity, leverage, tax efficiency, and future investing flexibility.Press play to learn how to build your financial foundation first—so your next investment opportunity doesn't come at the cost of long-term wealth.

On episode 213 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Barry Ritholtz and Blair duQuesnay to discuss: the current market environment, the importance of the market to the Trump admin, odds of a recession, and more! Submit your Ask The Compound questions to ⁠⁠⁠askthecompoundshow@gmail.com⁠⁠⁠  This episode is sponsored by Betterment for Advisors. Learn more at https://betterment.com/advisors

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereDo you really need $5 million in cash to be financially free—or is that number missing the bigger point?Many people hear bold retirement numbers from wealthy entrepreneurs and assume financial freedom is a fixed target. But the real question isn't just how much money you have—it's how much liquid, flexible capital you control. Without that buffer, investing can feel risky, market swings become stressful, and opportunities pass you by. Understanding your personal “wealth reservoir” could be the difference between constantly worrying about money and confidently making financial decisions.In this episode, you'll discover:Why the famous $5 million rule is less about the number and more about creating true financial flexibility.How a wealth reservoir (your “sleep-at-night” money) allows you to invest, take risks, and weather downturns with confidence.The different places your liquidity can live—from home equity and cash accounts to insurance strategies and other safe assets.Press play now to learn how building your own wealth reservoir can give you the freedom to invest smarter—and live on your terms.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you avoiding your RRSP because you're afraid it could become a massive tax problem later?If you're a high-income earner or incorporated business owner, you've probably wondered whether stuffing money into your RRSP today just means paying 50% tax on it tomorrow. Maybe you've even held back contributions, thinking you'll “optimize it later” when you have the perfect plan. But in trying to avoid a future tax issue, you could be missing the bigger risk: not building enough in the first place. Wealth doesn't grow because you perfectly optimized every detail — it grows because you consistently created bigger “problems” worth solving.In this episode, you'll discover:Why an “RRSP that's too big” is usually a sign you're doing something right — and how to handle it strategically.How leverage strategies and smart withdrawals can turn a future tax concern into an opportunity to grow even more.How to think about asset location across RRSPs, corporate accounts, and non-registered investments to maximize flexibility and long-term tax efficiency.Press play now to learn how to use your RRSP as a powerful wealth-building tool — not something to fear.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you holding too much cash “just in case” — and missing bigger wealth-building opportunities because of it?Most Canadians start with a simple emergency fund. But as your net worth grows, your “wealth reservoir” gets more complex — and more powerful. The problem? Many people never redefine their number. They double-count safety, sit on excess liquidity, or stay overly conservative without realizing it. Meanwhile, others jump into advanced strategies before they've earned the right to. If you've ever wondered whether your cash buffer is too small, too big, or just inefficient, this conversation will challenge how you think about financial security and opportunity.In this episode, you'll learn:How to clearly define your personal “tier one” emergency number — and why it should evolve over time.When excess liquidity becomes “gravy” that can strategically supercharge wealth through smarter moves.How your asset mix (real estate, ETFs, leveraged investing, business ownership) changes the size and role of your reservoir.Press play now to rethink your wealth reservoir and discover whether you're protecting your future — or unintentionally holding it back.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereShould you actually retire with debt on purpose?For years, you've probably pictured retirement as completely debt-free — no mortgage, no payments, no financial pressure. But what if aggressively paying off your home is actually slowing down your path to financial freedom? If you're a high-income earner, business owner, or someone intentionally building wealth, the real question isn't “How fast can I kill this debt?” — it's “Is this debt strategically working for me?” Understanding the role of cash flow, inflation, taxes, and risk can completely change how you see retirement planning.In this episode, you'll discover:How inflation quietly makes long-term debt less expensive over time — and why that matters for your strategyWhen carrying debt into retirement can actually improve tax efficiency and preserve wealthThe key difference between emotionally uncomfortable debt and strategically powerful debt (and how to know which side you're on)If you want to rethink retirement planning and learn when debt can be a tool — not a threat — press play now.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you accidentally letting hundreds of thousands of dollars sit idle in your holding company… unsure how to deploy it without triggering unnecessary tax?If you're a Canadian business owner with retained earnings building up in your holdco, you've probably felt the tension. You want to grow your wealth—but you don't want to make a costly mistake. Your accountant tracks what's happened, but who's helping you think proactively about what to do next? With salaries, RRSP room, rental properties, corporate investments, and tax efficiency all in play, it's easy to feel stuck between “do nothing” and “overcomplicate everything.” What you really want is clarity—and optionality.In this episode, you'll discover:A simple 50/50 framework for splitting retained earnings between risk-off liquidity and long-term growth.How to structure corporate investments to create tax-efficient capital gains and future tax-free income through the Capital Dividend Account.Why thinking holistically—across your corporation and personal assets—unlocks powerful flexibility, leverage, and long-term tax control.Press play now to learn how to turn your holding company into a strategic wealth engine—not just a parking lot for cash.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereIs index fund investing really the best path to financial freedom — or is it only effective if you can survive the emotional rollercoaster that comes with it?Most investors are told the same advice: buy the market, hold for decades, and trust long-term averages. And yes… mathematically, it works. But the real question is: can you stick with it when the market drops 20%? Or when you're retired and withdrawing income during a downturn?In this episode of Canadian Wealth Secrets, Kyle Pearce and Jon Orr break down a powerful question many Canadians overlook:Index Fund Investing: Growth Strategy or Income Strategy?They explore why index funds feel simple on paper, why real estate often feels “safer,” and how the best portfolio isn't just the one with the highest average return — it's the one you can actually stay committed to.This conversation dives into:The real reason many investors abandon index funds during market volatilityIndex fund vs real estate: why real estate feels more stable (even when it isn't)How an income investing strategy can reduce emotional decision-makingWhy leveraged investing in Canada looks great in spreadsheets but feels scary in real lifeWhat the 4 percent rule in Canada misses when markets decline during retirementHow to think about diversification, “dry powder,” and building a portfolio that supports long-term income needsIf you've ever wondered whether your RRSP, TFSA, or corporate investments are built for true financial freedom — or just built for average returns — this episode will shift the way you think about investing.

Ready to take a deep dive and learn how to generate personal tax-free cash flow from your corporation? Enroll in our FREE masterclass here and book a call hereAre you accidentally letting “dead equity” sit idle when it could be working harder for you?Most Canadians think financial freedom optimization is about cutting expenses or chasing the next hot investment. But what if the real opportunity is hiding in plain sight — in your car, your mortgage, or any asset quietly losing value? In this episode, we unpack a simple car lease scenario that reveals a much bigger question: Are you thinking strategically about debt, equity, and optionality — or just following the default path?If you've ever wondered whether to pay cash, finance, lease, invest, or “just play it safe,” this conversation will challenge how you evaluate those decisions.In this episode, you'll discover:How to spot “alpha” opportunities — small arbitrage moves that compound into meaningful advantagesThe difference between depreciating vs. appreciating assets — and how to reposition equity more strategicallyWhy optionality might be one of the most overlooked principles in building long-term financial flexibilityPress play now to start seeing everyday financial decisions through a sharper, more strategic lens.Discover which phase of wealth creation you are in. Take our quick assessment and you'll receive a custom wealth-building pathway that matches your phase and learn our CRA compliant tax optimized strategies. Take that assessment here.Canadian Wealth Secrets Show Notes Page:Consider reaching out to KylIn this episode of Canadian Wealth Secrets, a simple vehicle scenario becomes a powerful lesson in alpha, arbitrage, and optionality — revealing how smart CanReady to connect? Text us your comment including your phone number for a response!If you listen to podcasts like The Rational Reminder with Ben Felix & Cameron Passmore, The Canadian Investor, The Canadian Real Estate Investor, Build Wealth Canada with Kornel Szrejber, ChooseFI with Jonathan Mendonsa & Brad Barrett, Afford Anything with Paula Pant, The Ramsey Show with Dave Ramsey, BiggerPockets Money, The Money Guy Show with Brian Preston & Bo Hanson, Invest Like the Best with Patrick O'Shaughnessy, Masters in Business with Barry Ritholtz, The Wealthy Barber Podcast with David Chilton, Financial Audit with Caleb Hammer, In the Money with Amber Kanwar, The Loonie Hour with Steve Saretsky, or More Money Podcast with Jessica Moorhouse — we're confident you'll enjoy Canadian Wealth Secrets too.Canadian Wealth Secrets is an informative podcast that digs into the intricacies of building a robust portfolio, maximizing dividend returns, the nuances of real estate investment, and the complexities of business finance, while offering expert advice on wealth management, navigating capital gains tax, and understanding the role of financial institutions in personal finance.

#681: Barry Ritholtz's mom sold real estate. Those dinner table conversations about mortgages helped him spot the 2008 crash before most of Wall Street did. Now he runs Ritholtz Wealth Management and joins us to explain why we're often our own worst investment enemy. He breaks investing mistakes into three categories: bad ideas, bad numbers, and bad behavior. Here's what stood out. Research shows just 2 percent of stocks create all the market's value. The other 98 percent? Pretty much worthless. Barry says 90 percent of everything is garbage — from science fiction to investment advice. Even experts have blind spots. Michael Jordan dominated basketball but couldn't make it in minor league baseball. The lesson? Being brilliant at one thing doesn't make you brilliant at everything. Those financial memes everyone shares? They're misleading. Take Kevin's Home Alone groceries — $20 in 1990, $75 today. Sounds terrible until you realize wages went up the same amount. We actually spend less of our income on food now. Or that scary stat about the dollar losing 96 percent of its value over 100 years. Barry asks: who buries cash for a century? His math: $1,000 buried in 1925 buys almost nothing today. Same $1,000 invested in stocks? It's worth $32 million. Markets don't die of old age. Alan Greenspan warned about "irrational exuberance" in 1996. The Nasdaq kept climbing another 431 percent over four years. Recessions need triggers. They don't show up on schedule like buses. Fear wrecks more portfolios than anything else. Barry quotes neurologist William Bernstein: "Control your amygdala or die poor." Our fight-or-flight response helped us escape predators. It doesn't help us navigate market crashes. Make your investment plan before crisis hits. As Barry says, reading emergency instructions while the engine falls off at 25,000 feet is too late. He's seen every crash since 1987. Markets drop 30 to 40 percent about once a decade. Accept it. Plan for it. Barry advocates for Roth conversions and something called the "Mega Roth." Pay taxes now, withdraw tax-free later. We know today's tax rates. Future rates are anyone's guess. His bottom line: humans are terrible at predicting the future. Build portfolios that can survive anything, because anything will happen. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Intro (02:00) How fear of mistakes can make investors too conservative (06:00) Bad ideas vs good ideas in investing (09:00) Process over outcome in decision making (15:00) Thinking probabilistically about market outcomes (20:00) Why recessions and bull markets don't follow calendars (26:00) AI's real capabilities vs hype (33:00) Different market commentator archetypes (41:00) Expertise doesn't transfer between domains (50:00) Misleading financial statistics everywhere (56:00) Managing emotions when markets crash (1:00:00) Creating an investment plan before crisis (1:05:00) Tax strategies and Roth conversions Learn more about your ad choices. Visit podcastchoices.com/adchoices

On episode 205 of Ask The Compound, Ben Carlson and Duncan Hill are joined by Barry Ritholtz to discuss how to value today's stock market, the problem with credit card interest rate caps, the best financial news sources, if employer 401(k) contributions are enough, buy now or wait to save a bigger down payment and more. Submit your Ask The Compound questions to askthecompoundshow@gmail.com!  This episode is sponsored by Exhibit A. Visit: https://exhibitaforadvice.com/ to learn more. Subscribe to The Compound Newsletter for all the latest Compound content, live event announcements, find out who the next TCAF guest is, get updates on the latest merch drops, and more! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thecompoundnews.com/subscribe⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

My conversation with Barry starts at about      34 minutes in to today's show after headlines and clips Subscribe and Watch Interviews LIVE : On YOUTUBE.com/StandUpWithPete ON SubstackStandUpWithPete Stand Up is a daily podcast. I book,host,edit, post and promote new episodes with brilliant guests every day. This show is Ad free and fully supported by listeners like you! Please subscribe now for as little as 5$ and gain access to a community of over 750 awesome, curious, kind, funny, brilliant, generous soul How Not To Invest: The ideas, numbers, and behaviors that destroy wealth - and how to avoid them  The GREAT Barry Ritholtz who has spent his career helping people spot their own investment errors and to learn how to better manage their own financial behaviors. He is the creator of The Big Picture, often ranked as the number one financial blog to follow by The Wall Street Journal, New York Times, and others. Barry Ritholtz is the creator and host of Bloomberg's "Masters in Business" radio podcast, and a featured columnist at the Washington Post. He is the author of the Bailout Nation: How Greed and Easy Money Corrupted Wall Street and Shook the World Economy (Wiley, 2009). In addition to serving as Chairman and Chief Investment Officer of Ritholtz Wealth Management, he is also on the advisory boards of Riskalyze, and Peer Street, two leading financial technology startups bringing transparency and analytics to the investment business.  Barry has named one of the "15 Most Important Economic Journalists" in the United States, and has been called one of The 25 Most Dangerous People in Financial Media. When not working, he can be found with his wife and their two dogs on the north shore of Long Island. Join the SUPD Marketplace! Watch the video to learn how to post at StandUpWithPeteDominick.com/marketplace