Why Taxes Could Be Your Last Great Differentiator, And What to Do About It

The Advisor’s Guide to Long / Short Tax Strategies

In this episode of Advisor Wars, hosts Bob Huebscher (founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) continue their series on the role of tax planning in the advisory profession. This time they go deep on one of the more sophisticated and misunderstood tools available to RIAs: long/short overlay strategies for concentrated stock positions. Joining them is Brent Sullivan, founder of Tax Alpha Insider [https://www.taxalphainsider.com/] and a leading consultant to family offices and ultra-high-net-worth individuals on advanced tax management. Brent brings a rare engineering mindset to tax strategy and his precision shows. Concentrated stock positions are one of the most common, and most expensive, planning challenges for wealthy clients. The stakes are enormous, and the solutions go far beyond simply selling and paying the tax. Advisors who understand the full toolkit, including long/short overlays, exchange funds, Section 351 ETF contributions, and direct indexing, will be positioned to deliver far greater after-tax outcomes for their clients. Key takeaways for advisors: * Long/short is an alpha strategy first: The tax benefits are real, but they're the gravy, not the potato. Advisors who lead with tax and ignore alpha generation are missing the mark entirely. * The fishing net analogy: Direct indexing gives you $1 of harvesting surface for every $1 invested. Long/short can expand that to $3, $5, or more, dramatically widening the opportunity set for tax loss harvesting. * Short positions are a different beast: Unlimited risk, squeeze dynamics, lender recalls, and asymmetric custodian power make short exposure unlike anything in a traditional long-only portfolio. Advisors must understand this before recommending it. * Manager selection is everything: The RIA's job is rigorous due diligence, on alpha generation, risk management, operational competency, and short-position expertise. Picking the wrong manager is the most common mistake. * Jurisdiction matters: State tax regimes, like Washington State's unique capital gains structure, can significantly affect whether long/short is the right solution — or whether an exchange fund or options overlay makes more sense. * Flexibility is the long/short advantage: Unlike exchange funds or Section 351 contributions, long/short is fully customizable at the household level, allowing for liquidity access, tailored sector hedges, and even the ability to maintain some exposure to the concentrated position. * Costs are real and substantial: Manager fees, financing costs, and trading friction mean that alpha must be present and meaningful — not assumed. * Know your client's complexity tolerance: Some clients want to understand every layer of the strategy; others want to trust and delegate. The advisor's job is to map the solution to both the financial and psychological profile of the client. Long/short strategies are growing and as more managers enter the space and custodial lending infrastructure matures, they will become an increasingly important tool for advisors serving high-net-worth clients. Subscribe to Advisor Wars on YouTube, Apple Podcasts, and Spotify to catch every episode in this series on tax planning, including upcoming episodes on operational playbooks, client conversations, and building repeatable tax-aware processes. To learn more about Obsidian CIO or connect with Joe Halpern, visit www.obsidiancio.com [http://www.obsidiancio.com]. IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

Why Taxes Could Be Your Last Great Differentiator, And What to Do About It

In this episode of Advisor Wars, sponsored by Obsidian CIO, hosts Bob Huebscher (founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) kick off a new series on the role of tax planning in the advisory profession. Advisors will discover why mastering tax portfolio management may be the single most powerful way for RIAs to separate themselves from commodity advisors. Tax is one of the two largest lifetime expenses for most clients right alongside housing. Yet many advisors still treat it as an afterthought. In this episode, Bob and Joe explore why that can no longer be the case, what's changed in the advisory landscape over the last three to five years, and how the convergence of new products and better technology is raising the bar for what clients should expect. Key takeaways for advisors: * Tax is not optional: It's one of your client's top two lifetime expenses, treat it that way * Tax harvesting is table stakes: If you're not offering it, clients should be asking why * Premium strategies exist: Long/short tax extensions, exchange funds, and direct indexing go well beyond checkbox harvesting * Start with the basics: Maximizing 401(k) matches, 529s, and HSAs can make a bigger difference than any sophisticated product * Think in after-tax, after-fee returns: Gross performance is a distraction — net is what matters to clients * Technology is the great enabler: Advisors who build or partner with the right tech stack will be able to customize at scale in ways that were impossible just a few years ago * An OCIO can do what internal teams often can't: Deep focus on portfolio-level tax integration, freeing advisors to do what they do best, build client relationships The advisors who thrive in the next decade won't just manage portfolios. They'll manage tax outcomes. This episode tells you where to start. Subscribe to Advisor Wars on YouTube, Apple Podcasts, and Spotify to catch every episode in this series on tax planning, including upcoming episodes on operational playbooks, client conversations, and building repeatable tax-aware processes.  To learn more about Obsidian CIO or connect with Joe Halpern, go to www.obsidiancio.com or download their White Paper, How to Scale Your RIA to $1 Billion and Beyond [https://www.obsidiancio.com/resources/how-to-scale-your-ria/]. -- IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing. The podcast does not provide investment advice. Investment advice is offered only to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

How AI Will Transform Work, Longevity, and Wealth Management

In this special episode of Advisor Wars sponsored by Obsidian CIO, hosts Bob Huebscher (founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) sit down with one of the foremost experts in artificial intelligence, Dr. Alex Wissner-Gross, to explore what AI means for the future of wealth management and the financial advisory profession. Alex is a director or advisor to multiple AI companies, author of the daily AI newsletter The Innermost Loop, and co-host of the Moonshots podcast with Peter Diamandis. He is also co-author of the forthcoming book Solve Everything. Over 45 minutes, he delivers a sweeping and often surprising perspective on where AI is taking our economy and specifically what it means for advisors, RIA owners, and their clients. Whether you are deeply immersed in AI tools today or just beginning to explore what the technology means for your practice, this episode delivers critical context and practical implications that every financial professional needs to understand. Key takeaways for advisors: • Lean into AI now: Advisors who wait will fall behind  • Automate your own workflows: Full automation could be one to two years away  • Rethink your value proposition: Relationship management and holistic planning are the most durable advisory functions • Clients live longer: Prepare clients for a dramatically longer planning horizon as longevity science accelerates • Outsourcing: Outsourcing investment management (via an OCIO like Obsidian CIO) frees advisors to focus with confidence on their core value proposition.  The future of the profession will not look like the present, the advisors who thrive will be those who adopt and use AI. Follow Alex’s work by subscribing to The Innermost Loop [https://theinnermostloop.substack.com/], or the Moonshots [https://open.spotify.com/show/5Y1NyT6srGx38f5LINbH6c?_gl=1*1ahh4n*_gcl_au*MTk5NzQyODA5My4xNzc0Mjk1Mjk1] podcast with Peter Diamandis. Listeners can download the white paper by Obsidian CIO, How to Scale Your RIA to $1 Billion and Beyond [https://www.obsidiancio.com/resources/how-to-scale-your-ria/]. Subscribe to Advisor Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode.  -- IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is only offered to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

Alternative Investments Are Not Optional: Scott Welch on Going All-In on Alts

In this episode sponsored by Obsidian CIO, hosts Bob Huebscher (founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) go inside a leading multifamily office to show what a fully committed alternatives practice actually looks like in action. Joined by special guest Scott Welch, CIO and Partner at Certuity, a $4 billion multifamily office serving ultra-high-net-worth families across the country, this episode delivers an unfiltered look at how a seasoned investment professional sources, vets, sizes, and integrates alternative investments into real client portfolios. Scott’s bottom line for advisors considering alternatives: go all-in, or don’t go at all.  • Understand the Modified Endowment Model — Learn how Certuity adapts institutional investing principles for individual families, balancing global diversification, tax efficiency, and liquidity needs. • Define Your Alternatives Framework — Why Scott draws a sharp distinction between alternatives (hedge funds and diversifying strategies) and private markets (private equity and private credit) and why that distinction shapes every allocation decision. • Source and Vet Managers Like an Institutional Investor — Certuity applies a rigorous four-P framework (People, Philosophy, Process, Performance), why it favors deep relationships with fewer managers, and how Alt+ makes institutional minimums accessible to individual clients. • Size Alternatives to Move the Needle — Understand why a 20–25% allocation is the threshold that actually impacts portfolio performance and how to balance that against each client’s liquidity threshold and cash flow needs. • Build the Operational Infrastructure — Learn how Certuity handles capital calls, performance reporting, and consolidated K-1s at scale and where AI is beginning to streamline the process. Listeners can download the white paper by Obsidian CIO, How to Scale Your RIA to $1 Billion and Beyond [https://www.obsidiancio.com/resources/how-to-scale-your-ria/]. Subscribe to Advisor Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode.  --   IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is only offered to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.

What is Behind the Alt Craze and Why Are Advisors Behind?

In this episode sponsored by Obsidian CIO, hosts Bob Huebscher (founder of Advisor Perspectives) and Joe Halpern (Managing Partner and CIO of Obsidian CIO) investigate the forces driving the "alt craze" and why advisors are lagging behind the industry momentum. Joined by special guest Kendrick Wakeman, a 30-year industry veteran and CEO of WealthTech Strategy Partners, this episode unpacks the massive shift of alternative investments downstream into wealth management—and reveals the substantial gaps that still need to be filled before alternatives truly become mainstream for advisors and their clients. The conversation explores the technological, educational, and operational barriers preventing advisors from fully capitalizing on alternatives, from subscription processes that desperately need automation to the critical lack of due diligence frameworks and advisor education. Whether you're exploring alternatives for the first time or struggling with implementation, this episode delivers the strategic insights needed to understand where the industry is headed and what still needs to happen including: Understand the "Alts2Wealth" Movement - Learn what's really driving the democratization of alternatives and why institutional capital is pushing downstream. Identify the Critical Infrastructure Gaps - Discover the three key processes: onboarding, subscription, and post-trade management, that must be scaled for alternatives to reach mass adoption. Recognize the Role of TAMPs and OCIOs - Understand why outsourced platforms are positioned to become the biggest beneficiaries of the alts craze. Address the Education Deficit - Learn why advisor education remains the single largest human constraint holding back adoption. Evaluate Due Diligence Challenges - Understand why alternatives lack the standardized data and ratings that exist for public investments—and what needs to change. Anticipate the Next 5 Years - Get Kendrick's prediction for when the market will be fully deployed and what success looks like when "Alts2Wealth" simply becomes "wealth." Kendrick Wakeman and WealthTech Strategy Partners’ new White Paper is available here, What Really Needs to Happen for Alts2Wealth to Become Mainstream [https://www.wealthtechstrategy.com/post/what-really-needs-to-happen-for-alts2wealth-to-become-mainstream]. Listeners can download the new White Paper by Obsidian CIO, How to Scale Your RIA to $1 Billion and Beyond [https://www.obsidiancio.com/resources/how-to-scale-your-ria/]. Subscribe to Advisor Wars on YouTube, Apple Podcasts, and Spotify to ensure you never miss an episode. --- IMPORTANT DISCLOSURE: Obsidian CIO LLC sponsors the podcast to further education and critical thinking about the factors that affect markets and investing, and the podcast does not provide investment advice. Investment advice is only offered to clients of Obsidian CIO who have entered into an advisory agreement and with whom Obsidian CIO has identified individual objectives, risk tolerance, and other investment needs.