Podcast appearances and mentions of Barry Ritholtz

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.

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 carrying debt into retirement could actually reduce your taxes and increase your long-term flexibility?Many Canadians are taught that being mortgage-free is the ultimate financial goal—but what happens when that mindset clashes with taxes, retirement withdrawals, and lost growth opportunities? If the Smith Maneuver or leverage-based investing has ever made you uneasy, especially when you picture retirement looming, you're not alone. This episode breaks down why “good debt” doesn't suddenly stop working when your house is paid off—and how intentional use of leverage can turn future tax problems into strategic advantages.In this episode, you'll discover:How investment debt can offset RRSP/RRIF withdrawals and potentially eliminate taxes in retirementWhy starting the Smith Maneuver earlier creates more optionality and smoother income later onHow combining RRSPs, non-registered investments, and leverage can increase net worth while reducing long-term tax dragPress play now to learn how strategic debt, done right, can give you more control, lower taxes, and greater financial freedom over your lifetime.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 KylReady to connect? Text us your comment including your phone number for a response!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 you sitting on rental or business cash flow that could be quietly accelerating your mortgage payoff and cutting your tax bill at the same time?If you're a Canadian business owner, sole proprietor, or personally hold rental properties, chances are cash flows into your account each month—and then slowly leaks out to cover expenses. In this episode, Kyle and Jon unpack how that “idle” money can be put to work instead of collecting dust, using a strategy that builds on the Smith Manoeuvre without requiring you to go all-in or take on more risk than you can handle. They walk through real-world scenarios, common misconceptions, and the practical constraints that determine whether this strategy fits your situation.By listening, you'll learn how to:Turn non-deductible mortgage interest into deductible business or investment interest using cash damming—without increasing your overall debt.Improve cash-flow efficiency by recycling the same dollars to pay down your mortgage faster while still funding business or rental expenses.Apply the strategy conservatively or aggressively based on interest rates, mortgage rules, and your personal comfort level—so you stay in control.Press play now to see how cash damming could quietly boost your net worth and tax efficiency using money you already have.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 KylReady 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 hereHave you ever felt pressured into a “sophisticated” financial strategy you didn't actually understand?As a Canadian incorporated business owner or high-net-worth professional, you're used to handling complexity — but financial decisions feel different when the stakes are personal and the explanations fall short. Too often, strategies like estate freezes, corporate insurance, or private investments are presented with urgency instead of clarity, leaving you overwhelmed, hesitant, or quietly unsure if you're making the right move. This episode challenges the idea that pressure equals progress and reframes what real sophistication in wealth planning actually looks like.In this episode, you'll discover:Why poor financial outcomes usually come from lack of understanding, not bad strategiesHow to spot pressure from financial advisors disguised as “best practices” or “what wealthy people do”What confident, flexible wealth planning looks like when every tool has clear purpose and contextPress play to learn how clarity — not urgency — becomes the foundation of a wealth plan you can trust and stand behind.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 Kyleif you've been……taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…leReady 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.

Barry Ritholtz, chairman and chief investment officer at Ritholtz Wealth Management, says that while the stock market has blown past multiple red flags and warning signs, investors should not be acting as if indicators like an inverted yield curve, events like war or tariffs, or a simple market winning streak are leading to some sort of fast market shift. Rather than getting caught up in the next news story, Ritholtz says to focus on diversification and common-sense long-term investing strategies, and he notes that for all of the reasons investors are nervous, he would focus on earnings, noting that if he had only one variable to look at to forecast the market's potential, it would be earnings. So long as that trend continues — and he expects it to — the market should keep gaining ground. Todd Rosenbluth, head of research at VettaFi, looks to emerging markets with his ETF of the Week, picking a classic, low-cost, long-term fund that he says can be a core holding for investors looking to increase foreign exposure. Plus, Chuck discusses comments by Elon Musk suggesting that Americans really don't need to save for retirement any more. As ridiculous as that might sound, the principal Musk is relying on is called "universal high income," and it suggests that retirement savings won't be necessary because the abundance created by productivity gains created by artificial intelligence will make it so that all future material needs are easily met. While that outcome is possible, Chuck explains why you might still want to fund your Roth IRA for a while.

El libro “How NOT to Invest” de Barry Ritholtz redefine la idea tradicional de cómo invertir mejor y se centra en algo más importante: cómo evitar los errores que destruyen riqueza. Ritholtz —empresario y fundador de Ritholtz Wealth Management, firma con más de US$5 billones en activos— demuestra que incluso los inversionistas disciplinados pueden arruinar sus resultados por pequeños fallos que se acumulan. La obra no funciona como una guía para ganar dinero, sino como un manual para minimizar los errores financieros que deterioran un portafolio. El autor explica que evitar errores pesa más que acumular ganancias y que la clave está en reducir el costo de esos fallos inevitables. Según Ritholtz, esto es lo que diferencia a un inversionista del 98% de sus pares. El libro analiza cómo el miedo, las emociones y los sesgos cognitivos llevan a tomar malas decisiones, especialmente cuando se reacciona a noticias o eventos del mercado. Ritholtz propone mantener la racionalidad y evitar caer en ilusiones de control, como creer que se puede predecir el futuro del mercado. En cambio, invita a adoptar una perspectiva humilde, entender la incertidumbre y estudiar el comportamiento humano para simplificar un proceso naturalmente complejo. En esencia, “How NOT to Invest” ofrece una visión práctica basada en experiencia real y en análisis psicológico para ayudar a los inversionistas a proteger su patrimonio, tomar mejores decisiones y reducir el estrés financiero a largo plazo.

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 still a reliable path to financial freedom in Canada—or is it holding your retirement plan back?You've heard it a hundred times: save 25x your annual expenses and withdraw 4% per year in retirement. But in 2026 and beyond, does that formula still stack up? Whether you're 10 years out from retirement or already hitting your financial freedom number, rigidly following outdated rules could put your lifestyle—and peace of mind—at risk. This episode dives into how the 4% rule was built, why it may not fit today's market realities, and how to think more flexibly about spending, investing, and enjoying your money without watching your net worth dwindle.In this episode, you'll discover:Why the original 4% rule was designed for failure avoidance, not lifestyle optimizationHow a flexible approach to withdrawals can empower smarter spending decisions year by yearThe mindset shift that can help you grow your net worth even in retirementPress play now to rethink your retirement strategy and build a wealth plan that works for your real life—not just the spreadsheets.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 Kyleif 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 laReady 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 hereWhat should you do when your corporation has more cash than clarity?Many incorporated business owners hit a silent milestone: revenue is steady, personal income is solid, but inside the corporation, retained earnings quietly pile up—doing nothing. Inflation erodes their value. Investment options seem risky, tax-heavy, or too complex. The real challenge isn't just finding a strategy—it's knowing what role that idle money should play. In this episode, Tyson, a physiotherapy clinic owner, shares his journey from uncertainty to empowerment as he reframes his financial approach and builds a stable foundation for growth.You'll discover:Why retained earnings can become a hidden liability if left unstructuredThe mindset shift from chasing returns to preserving optionalityHow corporate-owned whole life insurance can offer growth, access, and protection—without rushing into risky decisionsIf your retained earnings feel stuck or exposed, press play now to hear how stability and strategy can unlock new possibilities.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…taking a salary with a goal of stuffing RRSPs;…inveReady to connect? Text us your comment including your phone number for a response!ManyReady 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 dividends really more tax-efficient for business owners—or is that advice costing you hundreds of thousands over time?If you're an incorporated Canadian business owner, you've likely heard the age-old advice: “Just take dividends—it's simpler and saves tax.” But what if that oversimplified strategy is quietly undermining your long-term wealth? In this episode, Jon and Kyle unpack the real math behind salary vs. dividends, revealing how your compensation choices ripple through CPP contributions, RRSP room, investment opportunities, and future flexibility. Whether your business is just starting out or generating strong retained earnings, understanding these trade-offs is crucial to building sustainable wealth.By the end of this episode, you'll discover:Why dividends don't always save tax—and when they can actually hurt your long-term growthHow to use salary strategically to open up RRSP room and diversify beyond your businessA clear, math-based breakdown of which approach works best at different income and retained earnings levelsPress play now to finally take the guesswork out of how you pay yourself—and make smarter, wealth-building decisions as an incorporated business owner.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…taking a salary with a goal of stuffing RRSPs;…inveReady 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 you relying on “just growing the pile” to fund your retirement?Too many Canadian business owners hope their savings will be “enough” without ever truly running the numbers—or questioning the assumptions behind their plan. In this episode, Jon Orr and Kyle Pearce break down a real case study of a listener preparing to retire at 55. They uncover the common blind spots around equity-heavy portfolios, the behavioral traps that derail even the smartest strategies, and why knowing your number isn't the same as building a system that gets you there. Whether you're 5 or 15 years out from retirement, this deep dive is full of insights to tighten your approach.You'll discover:Why a clear monthly cash flow target is more useful than a vague retirement “pile.”The risks of a 100% equity portfolio during the decumulation phase—and how to mitigate them.How to align your investment strategy with your behavior, so your plan doesn't fall apart when the market does.Press play now to find out where this listener nailed their strategy—and where small shifts could mean a more confident, flexible 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…taking a salary with a goal of stuffing RRSPs;…investing inside your corporation without a passive income tax minimization strategy;…letting a large suReady 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 your financial freedom being hijacked by your emotions?We all like to think we're logical with money—crunching the numbers, weighing the odds, making the “smart” move. But the truth? Most of our financial behavior is driven by emotion, not math. In this episode, Jon Orr and Kyle Pearce unpack the hidden psychological tug-of-war that shapes our habits, investment choices, and long-term wealth strategies. Inspired by Freakonomics Radio and grounded in behavioral finance, they explore why knowing what to do isn't the same as doing it—and what actually makes the difference.You'll discover:A practical framework (elephant vs. rider) for understanding and overcoming self-sabotaging money habits.How to bridge the gap between financial theory and real-life action—even when fear or doubt creeps in.Smart ways to align your investments and financial systems with behavior you can actually sustain.If you've ever struggled to follow through on the “right” financial move to gain financial freedom, press play now—this episode could change how you think (and act) with money.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…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 earReady 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

Barry Ritholtz, co-founder, chairman and CIO of Ritholtz Wealth Management, is out with a new book titled “How Not to Invest: The Ideas, Numbers, and Behavior that Destroy Wealth—and How to Avoid Them,” which he discusses along with his earlier book “Bailout Nation: How Greed and Easy Money Corrupted Wall Street and Shook the World Economy.” Ritholtz is also creator of The Big Picture blog, and creator and host of the Bloomberg podcast Masters in Business. (01/2026)

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

 Wall Street noise is loud—Barry Ritholtz shows you How Not to Invest. In this episode, we cut through models, headlines, and hype to focus on the few decisions that actually compound. Barry shares a practical framework for decision-making grounded in behavioral finance: why models are “wrong but useful,” how to build a checklist to filter signal from noise, and why broad indexing should anchor most portfolios. We dig into direct indexing for tax management, the attention economy's impact on investors, and the real effects of tariffs and Fed timing on markets and Main Street. He also maps the “two businesses” every investor must master: deploying capital quietly for decades and consuming information without getting captured by clickbait. If you're curious about AI's productivity boost, global mean reversion beyond the U.S., and realistic expectations after back-to-back strong years, this conversation is for you. By the end, you'll know How Not to Invest—and what to do instead.Connect with Barry Ritholtz: hownottoinvestbook.com Chapters:00:00 – Introduction02:32 – “All models are wrong, some are useful” & avoiding media-driven fear16:21 – Wealthy vs. middle-class planning: indexing, direct indexing, tax loss harvesting20:19 – AI's real impact on advisors, workflows, and productivity24:46 – Where are the opportunities? U.S. vs. developed ex-U.S., mean reversion35:14 – Rates, the Fed, soft landing probabilities & realistic return expectations49:33 – Gino wraps it up We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors)

SNAP benefits and Obamacare are hanging in the balance as the Shutdown drags on – US and China reach another "framework" for a deal as Trump ices out Canada – & an American farmer on the impact of Trump's trade war. Luke Broadwater, Susan Glasser, Larry Sabato, Barry Ritholtz, Matt Peterson, John Bartman, and Mark Mckinnon join The 11th Hour this Monday night. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.