Gimme Some Truth | Investing, Financial Advice for High-Net-Worth Families and Individuals

Walkner Condon Financial Advisors
  • 4.8 (20)
  • Investing
  • Updated Weekly

In a world full of financial information – and misinformation – what do you believe and incorporate into your life, and what do you throw away? As an independent, fee-only financial advisor, one of our founding pillars is education. Through accessible, transparent communication, we help filter out the noise for our clients to allow them to focus on their financial future. The goal of our podcast, Gimme Some Truth, is no different. From the corner of Monroe St. in Madison, WI, we cover the intersection of financial planning, investing, and everyday life. Disclosure: walknercondon.com/podcast

  1. 6d ago

    High-Net-Worth Insurance Mistakes: Disability, Life & Umbrella Coverage Gaps

    Choosing a health insurance plan during open enrollment is just the start. In this episode, financial advisors Nate, Clint and Andrew break down the insurance and protection gaps that most affect high-income and high-net-worth families — and how to fix them before they become expensive problems. Topics covered in this episode: ✅ Disability insurance caps and how "own occupation" vs. "any occupation" coverage affects high earners ✅ Real-world scenario: how disability insurance payouts fall short for a $240K/year executive ✅ Life insurance strategies for high-net-worth families, including multi-generational wealth transfer ✅ Term life insurance vs. permanent life insurance — and why permanent insurance gets an unfair reputation ✅ How inflation has driven up property and casualty insurance premiums ✅ Umbrella insurance policies: why $1 million in liability coverage isn't enough anymore ✅ How often to review coverage with your property & casualty insurance agent ✅ Open enrollment tips: how to choose the right health insurance plan for your family and budget If you're evaluating your insurance coverage this open enrollment season — or building a financial plan that accounts for real risk — this episode gives you the questions to ask your financial advisor and insurance agent. Keywords: disability insurance for high income earners, life insurance for high net worth, umbrella insurance policy, open enrollment health insurance tips, term vs permanent life insurance, financial planning for executives, property and casualty insurance inflation #DisabilityInsurance #LifeInsurance #UmbrellaInsurance #OpenEnrollment #FinancialPlanning #HighNetWorth #InsurancePlanning #WealthManagement Timestamps 0:00 – Intro: protection & insurance planning beyond health enrollment 1:09 – Disability insurance blind spots for high-income earners 3:01 – Scenario: disability insurance caps vs. a $240K executive salary 4:28 – Life insurance for high-net-worth families & wealth transfer 5:34 – Term vs. permanent life insurance: common mistakes 7:02 – Why permanent life insurance gets a bad reputation 9:18 – How inflation increased property & casualty insurance premiums 9:43 – Umbrella insurance explained: why $1M isn't enough anymore 11:42 – How often to review coverage with your P&C agent 12:17 – Open enrollment tips: choosing the right health insurance plan 14:01 – Why insurance belongs in a holistic financial plan 14:42 – Outro Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    High-Net-Worth Insurance Mistakes: Disability, Life & Umbrella Coverage Gaps

  2. Sep 21

    AI in Financial Advising: What It Can (and Can't) Do | Gimme Some Truth 2026

    Can AI replace your financial advisor? Clint Walkner and Nate Condon break down where artificial intelligence genuinely helps in investing, portfolio management, and financial planning — and where it still falls short. In this episode, we cover early AI adoption at our firm, how AI compares to the early internet boom, why AI valuations are moving at record speed, and why human oversight and real client relationships still can't be replaced by algorithms. ⏱️ TIMESTAMPS 0:00 – Introduction: AI's role in our world 1:57 – Early AI adoption at Walkner Condon 3:14 – Comparing the AI boom to the early internet era 3:32 – A cautionary investing story: Netscape to pets.com 4:55 – The industries and companies riding the AI wave 5:07 – Why AI valuations are moving at record speed (Anthropic case study) 6:43 – From macro to micro: how AI shapes investment decisions 6:58 – Why AI won't replace human oversight in portfolio management 8:07 – What AI does to human interaction and connection 9:20 – Why AI can't replicate decades of client relationships 10:32 – Preparing for the next 2008-style market event 13:45 – Why custom portfolios matter more than ever 14:26 – Unpacking what a "custom portfolio" really means 17:57 – Final thoughts: where human connection still wins Whether you're curious about AI's impact on investing, financial planning, or wealth management, this conversation offers a grounded, real-world perspective on where technology helps — and where human expertise remains essential. 📩 Want to learn more about how Walkner Condon uses AI, or have a topic you'd like us to cover? Reach out — we'd love to hear from you. 🌐 Learn more: https://www.walknercondon.com #AIinFinance #FinancialAdvisor #InvestmentManagement #WealthManagement #ArtificialIntelligence #FinancialPlanning #PortfolioManagement #GimmeSomeTruth #WalknerCondon #FinTech Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    AI in Financial Advising: What It Can (and Can't) Do | Gimme Some Truth 2026

  3. Sep 7

    Direct Indexing 101: The Tax-Saving Strategy High-Net-Worth Investors Use

    Direct indexing has become one of the hottest strategies in investing — but what is it, and does it actually work? In this episode of Gimme Some Truth, Nate, Mitch and Clint break down how direct indexing works, why it can outperform traditional index funds and ETFs on an after-tax basis, and who should actually be using it. Topics covered in this episode: ✅ What direct indexing is and how it differs from traditional index fund investing ✅ Tax alpha explained: how direct indexing creates tax savings that mutual funds and ETFs can't ✅ Real example: swapping individual stocks to harvest tax losses without losing diversification ✅ Why direct indexing offers flexibility ahead of a major capital gain event (like selling a business) ✅ How direct indexing helps retirees manage capital gains when withdrawing income ✅ Managing large unrealized gains from concentrated stock positions (early Apple investors, employees with company stock) ✅ Why rising capital gains tax rates make direct indexing more valuable over time ✅ Portfolio customization: excluding specific stocks for values-based, religious, or ESG investing ✅ Factor tilts: adjusting for growth vs. value, dividend income, and tax efficiency ✅ How direct indexing is customized based on your specific financial situation Timestamps 0:00 – Intro: what is direct indexing? 0:26 – Index investing vs. direct indexing: the basics 1:41 – Tax alpha: the core benefit of direct indexing 2:29 – Example: harvesting losses without losing diversification 3:06 – Why it matters: flexibility before a major capital gain event 4:16 – Avoiding forced capital gains in retirement 6:17 – Managing concentrated stock gains (Apple stock, business owners) 7:01 – Why rising capital gains tax rates make this strategy more valuable 7:22 – More control: excluding specific stocks from your portfolio 7:51 – Values-based & religious investing customization 8:36 – Factor tilts: growth vs. value and tax-efficient asset allocation 9:48 – How portfolios are actively managed and rebalanced 10:52 – Customizing strategy based on your financial situation 11:42 – Wrap-up: direct indexing 101 (and what's next) 12:00 – Bonus: NFL season predictions 14:14 – Outro If you're a high-net-worth investor, business owner, or retiree looking to reduce your tax bill while staying invested, this episode explains how direct indexing works and where it fits into a financial plan. 🔔 Subscribe to Gimme Some Truth for more straight-talk investing and financial planning advice. Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    Direct Indexing 101: The Tax-Saving Strategy High-Net-Worth Investors Use

  4. Aug 31

    Big Announcements: New HQ, a Promotion & a Retirement | Gimme Some Truth

    Walkner Condon's Managing Partners, Clint Walkner and Nate Condon sit down in their brand-new podcast studio to break down the biggest changes at Walkner Condon Financial Advisors this year— from a stunning new headquarters that brings four offices together under one roof, to major staff promotions, a retirement announcement, and the philosophy behind sustainable, client-first growth as the firm surpasses $1.25 billion in assets under management. In this episode of Gimme Some Truth, you'll hear about the team's new state-of-the-art studio and building, Alicia's promotion to partner, Evan's promotion, Andy King's upcoming retirement, how Walkner Condon structures its advisory teams for redundancy and collaboration, and why the firm has no "finish line" when it comes to growth. Timestamps: 0:00 – Welcome back & new studio reveal 0:34 – Behind the scenes of the new studio design 1:48 – New building: bringing four offices into one 3:54 – Staff update: Alicia promoted to partner 5:27 – Big news: Andy King announces retirement 10:00 – Why team structure & collaboration matter 15:35 – Philosophy on growth: no finish line 19:46 – Hitting $1.25 billion in assets under management 20:47 – Thank you to clients & closing thoughts Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    Big Announcements: New HQ, a Promotion & a Retirement | Gimme Some Truth

  5. Jul 20

    How to Tap Into Your Portfolio Without Triggering Capital Gains Tax — Box Spread Portfolio Loans Explained

    What if you could access the money in your investment account without selling a single share or triggering capital gains tax? In this episode of Gimme Some Truth, Ian and Alicia break down pledged asset lines (PALs) — what they are and how they work — and then introduce a newer, lesser-known alternative: the box spread portfolio loan. With lower interest rates, lower minimums, better tax treatment, and fewer restrictions on how you use the funds, box spread loans are quickly becoming a go-to strategy for investors sitting on large unrealized gains. If you've ever thought "I need cash but I don't want to sell," this episode walks you through exactly how to think about it. 🔑 Key topics covered: * What a pledged asset line is and how secured lending works * How box spread loans differ from PALs, HELOCs, and margin loans * Why box spread loans offer rates around 4% with minimums as low as $10K * The tax deductibility advantage most people don't know about * How interest payments become capital losses (and why that matters) * Real-world scenario: $100K invested, now worth $500K — what are your options? * Using box spread loans to diversify a concentrated position without triggering taxes * No restrictions on use of funds, setup in 1–2 weeks 📖 Check out our full blog post for more in-depth details on box spread loans. 📅 Book an appointment: walknercondon.com 📌 Chapters: 0:00 – Introduction & What Are Pledged Asset Lines (PALs)? 0:47 – The "PAL" Joke & Why Box Spread Loans Might Be Your Best Friend 1:04 – What Makes Box Spread Loans Different? 1:29 – What Is Secured Lending? How Does Borrowing Against Investments Work? 2:21 – Interest Rates & Other Lending Options Beyond PALs 2:41 – Introducing Box Spread Loans — A New Option for Individual Investors 4:26 – Benefits: Lower Rates (~4%), Lower Minimums ($10K vs. $100K), Better Tax Treatment 6:28 – The Tax Deductibility Advantage Over PALs and HELOCs 6:58 – Real-World Use Cases: Why Clients Are Choosing This 9:28 – Scenario Walkthrough: $100K Invested, Now Worth $500K — What Are Your Options? 10:33 – How Interest Becomes a Capital Loss — And Why That Matters 12:25 – Using Box Spread Loans to Diversify AND Eliminate Capital Gains Tax 16:00 – No Restrictions on Use of Funds (Unlike PALs or HELOCs) 17:22 – Speed & Flexibility: Set Up in 1–2 Weeks 20:25 – Why Working With a Financial Advisor Matters 23:45 – Disclaimer #BoxSpreadLoan #PledgedAssetLine #PAL #CapitalGainsTax #TaxPlanning #InvestmentStrategy #HELOC #SecuredLending #WealthManagement #FinancialPlanning #TaxEfficient #Liquidity #UnrealizedGains Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    How to Tap Into Your Portfolio Without Triggering Capital Gains Tax — Box Spread Portfolio Loans Explained

  6. Jul 6

    Non-Qualified Deferred Compensation (NQDC)— Risks, Rewards & What to Know Before You Elect

    Non-qualified deferred compensation could be one of the most valuable benefits you're not using. In this episode of Gimme Some Truth, we break down NQDC — a powerful but often overlooked benefit available to executives and high earners at many public companies. They cover how it works, who it's for, the key risks involved, and why planning ahead is critical before open enrollment season hits. If you're a senior leader, executive, or high-income earner at a public company, this episode could save you a significant amount in taxes — or help you avoid a costly mistake. 🔑 Key topics covered: * What "non-qualified" actually means and how NQDC differs from a 401(k) * How elections work and why NQDC is so inflexible once you commit * Choosing your payout timeline strategically * The biggest risk: what happens to your money if your company goes under * How investments work inside an NQDC plan * RSUs, taxes, and why your situation requires a personalized approach * What happens to your NQDC if you leave your company * Why you can't afford to wait for HR to bring this up 📌 Chapters: 0:00 – Introduction to Non-Qualified Deferred Compensation 0:42 – Who Has Access & How Common Is It? 1:52 – Why You Need to Ask About This Benefit 4:00 – What "Non-Qualified" Actually Means 4:54 – How Elections Work & The Inflexibility of NQDC 7:11 – Choosing Your Payout Timeline 8:14 – Best Use Cases: Who Should Use NQDC? 9:16 – The Key Risk: Company Creditworthiness 10:38 – 401(k) vs. NQDC — What's Protected? 11:13 – Annual Enrollment & The Exact Sciences Example 12:38 – How Investments Work Inside NQDC 13:26 – Don't Wait for Your Company to Tell You 15:25 – What Happens If You Leave Your Company? 16:13 – RSUs, Taxes & Why One Size Doesn't Fit All 16:55 – The Importance of Planning With Your Full Team 19:04 – When to Start the Conversation With Your Advisor 22:46 – Studio/Podcast Studio Announcement 24:09 – Disclaimer 📩 Have questions about your NQDC plan or open enrollment? Reach out to Walkner Condon to talk through your options. #NQDC #DeferredCompensation #ExecutiveCompensation #FinancialPlanning #TaxPlanning #401k #RSU #OpenEnrollment #WealthManagement #HighEarners #ExecBenefits #StockCompensation Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    Non-Qualified Deferred Compensation (NQDC)— Risks, Rewards & What to Know Before You Elect

  7. Jun 22

    Wisconsin Retirement System Explained — What Every WRS Participant Should Know

    The Wisconsin Retirement System is one of the best-funded public pension plans in the country — but most participants don't fully understand how it works or how to maximize it. In this episode of Gimme Some Truth, Nate, Andrew, and Clint break down everything you need to know about the WRS and ETF. Whether you're a state employee, teacher, or public sector worker in Wisconsin, this episode is packed with practical insight to help you make smarter decisions with your retirement benefits. Topics include how the pension actually works, the Core vs. Variable investment decision, what to do as retirement approaches, common misconceptions that cost people money, and how to think about it if you're considering leaving public service for a private sector role. 🔑 Key topics covered: * What the WRS is and how the pension benefit is calculated * Why the WRS is one of the healthiest pension plans in the US * WRS vs. Social Security as a guaranteed income floor * Core Fund vs. Variable Fund: the 60/40 vs. 100% stock decision * The one-time switch back to Core and what to do as retirement approaches * Why "I have WRS, I don't need to save anything else" is a dangerous assumption * Leaving for the private sector: is that 15% raise actually worth it? * How to read your WRS statement and use ETF office projections 📌 Chapters: 0:00 – Introduction & Clint's Background With WRS 1:01 – Why This Topic Matters & Common Misconceptions 4:42 – What Is a Pension? WRS Basics Explained 6:51 – WRS vs. Social Security: Building a Guaranteed Income Floor 7:00 – Core vs. Variable: Investment Options Inside the Plan 9:36 – Approaching Retirement: The One-Time Core Switch & Practical Steps 11:27 – "WRS Is Enough" — Why You Should Still Save Outside the Plan 12:34 – Is Leaving for a Private Sector Job Worth It? 16:07 – Private Pensions: What's Different & What to Watch Out For 17:44 – Final Tips: Reading Your Statement & Visiting the ETF Office 📬 Have questions about your WRS benefits or retirement plan? Reach out to the team at walknercondon.com #WRS #WisconsinRetirementSystem #ETF #WisconsinPension #PublicPension #RetirementPlanning #StateEmployees #TeacherRetirement #PensionPlan #FinancialPlanning #CoreVsVariable #PublicSectorRetirement #Wisconsin Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    Wisconsin Retirement System Explained — What Every WRS Participant Should Know

  8. Jun 8

    Why Retirement Is Harder Than You Think, Part 2: Hidden Costs, Tax Traps & Tough Conversations

    Clint and Nate are back for another honest conversation about what retirement actually looks like — and what most people don't see coming. Retirement planning isn't just about the numbers. In this episode of Gimme Some Truth, Clint and Nate dig into the real social and financial challenges that catch people off guard once they stop working. They start with something almost nobody plans for: what happens when spouses have completely different visions of retirement. One partner wants to travel, the other wants to keep working part-time — and neither has said it out loud. From there, they tackle the "I'll just consult" plan that so many pre-retirees lean on. It sounds easy in theory, but the reality is more complicated than most people expect — especially once you factor in the tax implications, Medicare timing, and Social Security coordination. The conversation also covers one of the most emotionally loaded topics in retirement planning: gifting money to your kids. Clint and Nate explain how well-meaning gifts can create unintended expectations, and why transferring your house to your children before you pass away can trigger serious tax consequences (including losing the stepped-up cost basis). They also break down a growing line item in retirement budgets: wellness spending. Personal trainers, red light therapy, supplements, gym memberships — these costs add up faster than most people anticipate, and they're rarely part of the original plan. Whether you're five years out from retirement or already there, this episode will help you think more clearly about the financial and personal decisions ahead — and why open communication with your spouse, your kids, and your advisor is the most valuable tool you have. Topics covered: - Why couples often enter retirement with completely different mindsets - The "I'll just consult" plan and why it's harder than it sounds - Financial impact of part-time consulting on taxes, Medicare, and Social Security - How gifting money to your kids can create unintended expectations - Why transferring your house to your children is usually a tax mistake - The emotional hurdle of taking your first portfolio withdrawal - Die With Zero philosophy and how to build a gifting plan the right way - Budgeting for wellness in retirement — personal trainers, therapy, and more - Why open communication is the #1 tool in your retirement toolkit Chapters: 0:00 – Introduction & Best Movie Sequels 2:10 – What Retirement Really Feels Like 3:25 – Couples & Mismatched Retirement Mindsets 5:55 – The "Maybe I'll Consult" Boomerang 8:19 – Gifting Money to Kids: The Slippery Slope 8:45 – Financial Impact of Consulting (Taxes, Medicare, Social Security) 9:33 – The First Withdrawal Is the Hardest 11:56 – Die With Zero & Gifting Plans Done Right 14:05 – Healthcare & Wellness Costs in Retirement 14:06 – Transferring Your House to Your Kids (Don't Do It) 15:28 – Red Light Therapy, Trainers & the Real Wellness Budget 15:55 – Final Thoughts & Communication as the Core Theme 16:34 – Disclaimer Subscribe @walknercondon Visit our website for more financial planning resources and educational information: https://www.walknercondon.com ———————————————— ADD US ON: LinkedIn: https://linkedin.com/company/walkner-condon-financial-advisors-llc Facebook: https://facebook.com/walknercondon

    Why Retirement Is Harder Than You Think, Part 2: Hidden Costs, Tax Traps & Tough Conversations
See All (289)

Ratings & Reviews

4.8
out of 5
20 Ratings

About

In a world full of financial information – and misinformation – what do you believe and incorporate into your life, and what do you throw away? As an independent, fee-only financial advisor, one of our founding pillars is education. Through accessible, transparent communication, we help filter out the noise for our clients to allow them to focus on their financial future. The goal of our podcast, Gimme Some Truth, is no different. From the corner of Monroe St. in Madison, WI, we cover the intersection of financial planning, investing, and everyday life. Disclosure: walknercondon.com/podcast

Information

You Might Also Like