South Florida's Real Estate Center Of Gravity Is Finally Moving West
By dollar value, it's been a big month for Florida luxury real estate.
Last week, a 15-acre Naples waterfront estate closed for a whopping $225 million, the second highest home sale price in U.S. history and a new state record, dwarfing the $173 million Oracle's Larry Ellison paid for his Manalapan estate south of Palm Beach in 2022. According to news reports, activist investor David Hoffmann is also under contract on a separate Naples estate for an undisclosed sum north of $100 million.
Across the Everglades on the other side of the state, high eight-figure deals are closing at an equivalent clip, including a La Gorce Island estate in Miami Beach which recently settled for $75 million. In total, sixteen homes priced at $40 million-plus have sold in Florida in the past six months.
The Waldorf Astoria Residences St. Petersburg just launched sales. The development is the fourth Waldorf Astoria Residences in the U.S. after Miami, Denver, and Pompano Beach
The islands between downtown Miami and Miami Beach on Biscayne Bay, including Star Island in the foreground, feature some of the most expensive waterfront estates in America
These are big numbers in short order even by Florida's recent standards, particularly with the stock market whipsawing, the full measure of President Trump's tariffs still unknown, and the risk of a wider economic downturn looking more plausible by the day.
More broadly, the sales reaffirm several current trends. First, the asymmetry between the two ends of the housing market is widening further. On the mid to lower six-figure pitch where most Americans play, the majority of buyers are still spooked by punitive interest rates, stubborn inflation, and a legitimate unease about buying high. Not surprisingly, overall inventory is up, appreciation is decelerating, and sellers no longer have the stronger hand.
The other end of the housing market is showing more verve and braggadocio: before COVID, multi-million dollar properties could sit for years. Today, in most markets, they are still trading briskly while largely resisting the headwinds depressing the rest of the industry.
Affluent real estate markets with limited inventory like Aspen have experienced a noticeable increase in sales activity since the pandemic
The growing asymmetry signals a hardening of a second trend originally triggered by the pandemic. With fiscal certainty still at a premium, wealthy buyers who can close all-cash deals are continuing to seek safe harbor in hard assets with limited supply: ergo, ultra-luxury real estate in NIMBY-enclaves where tight geography and even tighter zoning regulations keep inventory scarce and prices elevated. The S&P 500's 77% bump since COVID also has roughly doubled the world's eight and nine figure multi-millionaires. As a result, the overall demand for high-end residences in rarified communities with small airports and long runways, such as Aspen, Park City, Palo Alto, and Naples, looks to remain frothy for the foreseeable future.
The third trend borne out of the past month's lather is geographic. If anything were poised to suck the oxygen out of Florida's luxury real estate boom since the pandemic, it still hasn't happened yet. And it's financial center of gravity is finally, inevitably moving west.
The Central Park and Steinway Towers on the sunset in Manhattan
This is all welcome news for Ryan Shear, Managing Partner at Property Markets Group (PMG), a Miami-based real estate development firm that's behind some of America's most architecturally iconic — and exclusive — residential high rises, including 111 W. 57th St. on Manhattan's 'Billionaire's Row' (a.k.a. 'the world's skinniest skyscraper') which, at 1,428', ranks as the second tallest residential building in the Western Hemisphere.
This week, PMG announced the launch of its newest precipitus opus: the Waldorf Astoria Residences St. Petersburg, a soaring 50-story tower that will be the Florida city's tallest, priciest, and most palatial building once completed in 2030. For the storied hotel brand — originally founded in New York City in 1893 (now owned by Hilton) — the new development will be its fourth residential high rise in the U.S., following groundbreaking of the Waldorf Astoria Pompano Beach this month, the launch of Waldorf Astoria Denver Cherry Creek last year, and the Waldorf Astoria Miami which is currently under construction. For PMG, the project signifies an ever-deeper push into the luxury branded residence space and its biggest bet yet that the hyper-posh, super-amenitized, starchitect-designed high rise formula the company has mastered in Miami is just getting started on the other side of the state.
Floor to ceiling windows frame endless Tampa Bay and Gulf views from every floor of the Waldorf Astoria Residences St. Petersburg
Gourmet kitchens at the Waldorf Astoria Residences St. Petersburg
Priced out of Miami, many high net worth individuals are moving their money and Florida's real estate momentum to the state's Gulf Coast including cities like St. Petersburg and Naples
The Waldorf Astoria Residences St. Petersburg (pictured center) will transform the city's skyline and is anticipated to usher in a new wave of luxury development downtown
In many respects, Waldorf Astoria Residences St. Petersburg is surfing a wave that's been breaking for years. The branded residential real estate space has been on a tear since well before the pandemic, outpacing the wider housing market by almost every metric and fueling a free-for-all of new entrants and partnerships both in South Florida and around the world. The forces and factors driving the sector — 5-star service, brand loyalty, and higher re-sale value, among others — have been exhaustively covered in dozens of articles, mine included, so I don't need to undress them further here.
What's noticeably different this time around, though, is the place on the Monopoly board Shear and PMG are putting new foundations in the ground. Historically most high-profile brands that have waded into the fray — among them early pioneers like Ritz-Carlton and Four Seasons and, more recently, Nobu, Aston Martin, and Armani — have tended to cluster around glitzy, global metropolises where real estate values are already sky high and the world's 1% like to throw their money around, such as Manhattan, Miami, and Dubai. They're also clustered in exclusive resort destinations in Los Cabos, the Yucatan, and the Caribbean.
A dining room rendering at the Waldorf Astoria Residences St. Petersburg
Every residence at the Waldorf Astoria St. Petersburg has its own private foyer
That makes the prospect of a Waldorf Astoria tower in downtown St. Petersburg an outlier on the trend line which, in turn, portends a potentially significant shift in how the luxury branded residence game is played. If Florida's central Gulf Coast — traditionally a magnet for Midwestern retirees and spring break beach benders — is worthy of world-class architecture and a high-society brand like Waldorf Astoria, who's to say Raleigh-Durham and Colorado Springs aren't next?
The reality is more complicated. Notwithstanding its fixed, physical form, real estate is innately fluid, albeit on a relatively more molten scale. Tastes change. Buildings decay. Neighborhoods evolve. Consequently, up-and-coming locations that simmered with possibility two decades ago might very well be tapped out today (think Fort Lauderdale). Similarly, cities and commercial corridors currently deemed 'second tier' or not befitting a Fendi, Cipriani, or comparably premium brand could be the next Nashville or Park Slope hiding in plain sight.
St. Petersburg, Florida is often ranked one of America's best places to live and retire due to its affordability, safety, and healthy quality of life
St. Petersburg Beach and Clearwater Beach are two of the state's most stunning stretches of Gulf Coast
By this measure, St. Petersburg is definitely having its 'moment' — along with the rest of the greater Tampa Bay region for that matter. The drivers behind the boom are the usual Florida suspects: warm weather, low taxes, a healthy lifestyle, strong job growth, and a blossoming entrepreneurial scene thanks to a widespread in-migration of talent during the pandemic.
Yet, what's currently happening in St. Petersburg is also part of a wider, longer-term trend. Miami-Dade, Broward, and Palm Beach counties on the state's Atlantic Coast are finally spilling over, especially among the NetJets' crowd. As a result, savvy investors and wealthy buyers now priced out of traditionally tony waterfront enclaves like Bal Harbor, Surfside, Jupiter, and SoFi ('South of Fifth') in Miami Beach are shifting their dollars — and Florida's center of affluence — westward.
'Florida's Gulf coast is among the most under-valued real estate markets in the country,' Shear tells me, 'Especially compared with cities like Miami and West Palm Beach. St. Pete is a hidden gem that's been under the radar for a very long time and it's just beginning to come into its own. The city is also becoming a magnet for high net-worth individuals thanks to its vibrant cultural scene, stunning waterfront, and exceptional quality of life.'
Th architecturally iconic Salvador Dali Museum houses the largest collection of work by the famed artist outside of Europe
An aerial perspective of St. Petersburg. Tropicana Field in the foreground is the home of MLB's Tampa Bay Rays
For the locals and snowbirds who discovered St. Petersburg long before Wall Street and Big Tech did, none of this current praise-heaping comes as a surprise. The city often rates as one of America's best places to live and retire on account of its affordability, walkability, beach access, up-and-coming culinary scene, and world-renowned art museums, galleries, and performance venues, including the Salvador Dalí Museum as well as the Chiluly Collection at the Morean Arts Center.
Socially and economically, St. Pete is also safe and inclusive and boasts a diversified economy with industries like healthcare and technology playing a significant role in the city's sustainable growth in addition to tourism. In a recent study by WalletHub ranking the 'Best-& Worst-Run Cities in America', St. Pete ranked #1 in Florida overall. Nationally, the city's economy ranked second, ahead of Atlanta, Charlotte, and Austin (by comparison, Miami came in #62, Fort Lauderdale #121).
St. Petersburg Pier is one of the city's most popular tourist attractions
Old Southeast is one of St. Petersburg's most historic downtown neighborhoods
Sunshine Skyway Bridge connects St. Petersburg to Tampa Bay
'St. Pete has arrived,' says Larry Feldman, CEO of Feldman Equities which is co-developing the Waldorf Astoria St. Petersburg with PMG. 'Over the past few years, we've witnessed the city's incredible rise. And the introduction of the Waldorf Astoria brand is testament to this extensive growth and the natural progression St. Pete has undergone. We're eager to deliver a branded residential development that meets the elevated caliber of living the city's new residents desire, and I can't wait to see all of the opportunities and incredible experiences this project will contribute to the downtown area.'
The Waldorf Astoria Residences St. Petersburg will add a striking new silhouette to the city's waterfront skyline
Beach Drive in downtown St Petersburg is one of the city's primary thoroughfares
On this last point, Feldman made me realize something else about the current state of the branded residential real estate space: that it's actually quite symbiotic. For Feldman, Shear, PMG, and Waldorf Astoria, St. Pete offers a rare opportunity: a lead position in an A-series round if Facebook were luxury real estate. In return, St. Pete gains global credibility virtually overnight thanks to Waldorf's 'legitimatizing' effect on the city's reputation, much the same way a James Beard award-winning chef opening up a new restaurant in a neighborhood that's revitalizing is usually a sure sign it's 'arrived'
As a result, the value of Waldorf Astoria coming to St. Petersburg is far from simply architectural or temporarily economic in terms of job creation and investment. The original Waldorf hotel on Fifth Avenue in Manhattan hosted diplomats and distinguished foreign visitors and catered to the needs of New York's socially prominent, 'upper crust". The Waldorf was also renowned for setting the original standards for luxury and indulgence in hospitality, including becoming the first hotel in the world to offer electricity and private bathrooms in every room.
'A project of this scale and caliber with a globally revered 5-star brand like the Waldorf Astoria attached has a profound, legitimizing effect on a city like St. Petersburg,' explains Shear. 'It serves as a powerful signal that the city is not just on the rise, but poised for its next chapter of growth and transformation. St. Pete is a major luxury market that deserves the Waldorf brand, and this project will help the city gain global recognition, bring long-term development benefits, and I'm confident that other 5-star brands will follow suit.'
Clearwater Beach Pier
Kiteboarding on Tampa Bay in St. Petersburg captures the essence of the region's healthy, active, outdoor lifestyle
The Museum of Fine Arts in downtown St. Petersburg is one of many nationally and world-renowned arts and cultural institutions in the city
Another powerful side effect of a high-profile branded residential real estate project coming to a city like St. Petersburg is its 'globalizing' effect, particularly in South Florida, which has long been a magnet for foreign capital, and especially when an internationally recognized brand like Waldorf Astoria is involved. Shear anticipates that at least 30% of his buyers will come from Europe and Latin America, most of whom will reside in St. Pete part of the year and all of whom regard their purchases as a long-term financial investment (the other 70% will come from the Midwest and Northeast).
'We're all selling sunshine and low taxes in Florida,' Shear says, 'But along the West Coast in areas like Tampa and St. Petersburg specifically, premium real estate remains resilient, driven by sustained demand from both domestic and international high net-worth individuals who view the current market conditions as an opportunity to invest in tangible U.S. assets like real estate, which has long been a cornerstone of long-term wealth building. But unlike other investments, real estate offers the added benefit of personal enjoyment and use, delivering value beyond just financial returns especially when you consider that you're living in a 5-star hotel.'
The Waldorf Astoria St. Petersburg will be the tallest building in the city once it's completed offering endless horizon views from every residence
No luxury or amenity is spared at the Waldorf Astoria Residences St. Petersburg, in keeping with the original legacy of the brand
Custom made Italian vanities are one of many lavish fixtures and furnishings that are featured in the residences
To merge Waldorf Astoria's rich legacy with St. Pete's unique history, character, and charm, PMG has tapped CUBE 3 for the tower architecture with interiors curated by the award-winning design firm BAMO. The high rise's fully finished two- and three-bedroom residences will range from 2,031 square feet to 3,408 square feet and feature private foyers, custom closets, Italian vanities, chef's kitchens, and expansive terraces with Tampa Bay views along with finishes, furnishings, and appliances befitting the Waldorf reputation for unparalleled décor and design. The tower's top two-stories will be combined into the penthouse residence that will encompass 10,000 square feet overall with a private pool.
On the amenities side, a 20,000-square-foot, resort-style pool deck will feature a 160-foot east pool with Bay views, a sunset pool with dual spas, elegant lounge areas, and a bar, while the Amenity Suite on Level 18 offers a thoughtfully curated wellness center prioritizing holistic healing and connection with nature. Spaces in the center will include private massage rooms, his and her saunas and steam rooms, as well as a state-of-the-art fitness center and movement studio. On Level 46, residents will have exclusive access to the legendary Peacock Alley-inspired Sky Lounge, a signature space that captures the legacy, elegance, and sophistication of the Waldorf Astoria brand.
The end of another perfect day at St. Pete Beach
As for the next evolution in the luxury branded residence space?
Shear remains bullish on the niche market as well as the long-term drivers underpinning it.
'We never really know until we launch a new project, but we feel strongly that there is real depth for branded real estate developments not just in cities like Miami, but in cities like St. Petersburg too,' he says. 'All indications are that there continues to be strong demand not only for seasoned, well-capitalized developers who deliver on time, but also for 5-star brands like Waldorf Astoria that offer buyers peace of mind, an exceptional quality of life, and design, quality, and craftsmanship that are second to none.'
If Shear's instincts are right — which, based on PMG's track record, they usually are — St. Petersburg and the wider Tampa Bay region, including Sarasota and Bradenton, are just getting started.
Residences at the Waldorf Astoria Residences St. Petersburg start in the mid-$2m.
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Los Angeles Times
42 minutes ago
- Los Angeles Times
Gal Ben-Naim, Joshua Driskell, Jordi Pujol, and Mike Watson Share Insights on Wealth Management and Estate Planning
The Wealth Management & Estate Planning roundtable is produced by the LA Times Studios team in conjunction with Axos Securities, LLC; IDB Bank; Lagerlof, LLP; and Objective, Investment Banking & Valuation. Ongoing market developments across multiple sectors have helped to open up new private wealth management products and services to a broader array of people and families. This, along with a surge among high-net-worth families exploring ways to better manage their finances and making plans for their estates in today's economic environment, is an indicator of just how important the wealth management process has become. To take a closer look at the latest trends, best practices and concerns across the wealth management landscape, we turned to four of the region's leading experts on the topic, who graciously weighed in for a discussion and shared insights on the state of wealth management in 2025. Q: How would you describe the current investment environment in 2025 and what do you consider to be the best investment approach in general terms? Gal Ben-Naim, Head of Private Banking Group, California, IDB Bank: The first half of this year has really been about uncertainty and volatility, and it's causing a lot of investors, even the seasoned ones, to feel nervous. We expected some economic and market transitions with an incoming administration, but I think most investors have been surprised by the extent of what we've seen – including the worst day in the stock market since COVID. While tariffs are front and center, our broader economy is really a reflection of compounding factors – geopolitical uncertainty and conflict, inconsistent messaging on inflationary trends and a softening labor market. Our team at IDB believes that healthy portfolio diversification with a focus in alternative assets that don't solely rely on market activity. While this has been an unusually complicated environment, it's given us a chance to really understand the value of our approach in minimizing downside to our clients and continue to support mid- and long-term planning. Mike Watson, Head of Securities, Axos Securities, LLC: The 2025 investment environment is defined by persistent volatility, tighter monetary policy and rapid technological disruption. In this landscape, the best approach is a disciplined, diversified strategy with a strong focus on quality assets, risk management and long-term value creation. Flexibility and a global perspective are more important than ever. Jordi Pujol, Managing Director, Objective, Investment Banking & Valuation: It's more clear we've transitioned to a post-speculation cycle. With capital no longer as cheap, investors can no longer rely on rising multiples to justify weak underwriting. In 2025, the most resilient portfolios are focused, yield-conscious and grounded in fundamental cash flow. They are not driven purely by momentum or narrative, but rather by defensible moats and process-oriented scalability. Cash yield, margin of safety and strategic defensibility have replaced passive diversification as the cornerstones of disciplined investing. Private markets have notably shifted from 'growth at any price' to 'performance at the right price.' Investors are paying less for vision and more for repeatability of outcomes. Growth stories need to be backed up by real traction, recurring processes and sustainable/scalable growth. This environment demands real-time valuation discipline and quarterly stress testing of private holdings. Think forward when modeling but underwrite like the exit is tomorrow. Backward-looking assumptions and forward-looking hype no longer suffice. Q: What are the most critical strategies high-net-worth individuals should prioritize in today's economic environment? Joshua Driskell, Managing Partner, Lagerlof, LLP: High-net-worth individuals should prioritize flexibility, tax efficiency and multigenerational planning. With inflation, interest rate fluctuations and potential changes in tax law, building a nimble structure is essential. That includes diversifying asset classes, stress-testing estate plans under higher estate or capital gains tax regimes, and taking advantage of current exemptions before they sunset. Establishing irrevocable grantor trusts, family limited partnerships and charitable vehicles can preserve wealth while achieving strategic goals. Proactive wealth transfers, such as installment sales to defective trusts or GRATs, can lock in valuation discounts and freeze estate value. Most importantly, integrate estate and investment planning with family governance to promote cohesion and legacy continuity. Pujol: In today's environment, high-net-worth individuals should prioritize three things: ownership in assets they understand, tax-efficient structures informed by valuation foresight, and optionality through enhanced liquidity. Long-term capital growth is not about chasing trends or the cliched shiny objects but about staying positioned for the right opportunities. We're seeing a move away from over-diversified portfolios toward intentional ownership, where control, structure and timing drive outcomes. This means more alternatives, a mix of private and public holdings, and tax-minimizing structures. Ownership in assets you'd fight to keep, that's the new diversification. I also like the 'cockroach' approach, which is building portfolios that survive the panoply of circumstances the world is throwing at us by selecting traditional and non-traditional asset classes, making sure that correlation is low. I also think cash yields make liquidity an asset and not a drag on returns; it's strategic capital with a clear purpose of optionality. When opportunities arise, those with dry powder and a defined investment playbook are positioned to act quickly and decisively. The most successful families today follow a clear investment policy that outlines the investment discipline before emotions take over. In this environment, structure and readiness matter more than broad diversification. Ben-Naim: It's not as simple as building your wealth across stocks, bonds and cash anymore. In the past seven to 10 years, we've helped many of our clients increase their alternative asset exposure – ranging from equity and debt investment in commercial real estate, direct lending and hedge funds – from 5% to about 20%, with very positive results due to the less volatile and emotions-driven public market. Our current cycle has also highlighted the importance of hedging strategies. Investors should work closely with their advisors to identify safeguards on the equity market as well as private market entry points that will create protections on the downside, while maintaining participation on the upside. We've seen very positive outcomes as a result of these strategies. Many of our clients who have been allocating funds to private markets have been largely shielded from the recent volatility. Now, they are even taking steps to allocate more funds into these verticals. Q: How should investors rebalance their portfolios in response to shifting interest rates and market volatility? Watson: In today's dynamic environment, rebalancing decisions should be made with a clear understanding of how shifting interest rates and market volatility affect different asset classes. Rather than attempting to time the market or make reactive moves, investors should work closely with a qualified investment advisor who can assess their overall investment time horizon, risk profile and long-term goals. An advisor can provide guidance on when and how to adjust asset allocations, evaluate the impact of interest rate changes on fixed income and equity risk and returns, and implement a disciplined, tax-efficient rebalancing approach. With full visibility into an investor's financial profile, an advisor is able to provide holistic guidance. Professional oversight ensures that adjustments are strategic, not emotional, and aligned with broader financial objectives. Q: What planning opportunities exist when a trust changes from a grantor trust to a non-grantor trust? Driskell: When a trust converts from grantor to non-grantor status – often due to a death or other triggering event – it opens both risks and planning opportunities. Income tax liability shifts from the grantor to the trust itself or its beneficiaries. Advisors should evaluate whether the trust will accumulate or distribute income to manage compressed trust tax brackets. Capital gain planning becomes especially important. Trustees may consider investing in tax-efficient assets or making distributions to lower-bracket beneficiaries. Basis tracking must be updated, especially for assets with low carryover basis. In some cases, trust modification, decanting or converting to an incomplete non-grantor (ING) trust may optimize results. Coordinating with CPAs and estate counsel at the transition point is essential for tax and fiduciary compliance. Q: What are some of the biggest mistakes you see individuals make when managing their wealth, and how can they avoid them? Watson: There are a number of common mistakes. One is the lack of having a long-term plan and clear strategy. The solution for this is to develop a comprehensive financial plan, revisited regularly, aligned with your life goals, risk tolerance and time horizon. Another mistake we see is emotional decision-making. This can be avoided by staying disciplined, relying on objective advice and using a rules-based rebalancing strategy to manage volatility. Neglecting tax efficiency is a mistake that can be avoided by optimizing asset location, using tax-deferred accounts, harvesting losses strategically and engaging in proactive estate planning. Another misstep is over-concentration in a single asset or sector. Investors should diversify across asset classes, industries and geographies to reduce risk. Another mistake to avoid is failing to plan for liquidity needs. It is important to maintain a liquidity buffer for emergencies, major purchases or investment opportunities. Finally, another of the biggest mistakes we see is when people ignore succession and estate planning. It is always good to engage advisors early to create trusts, wills and governance structures that reflect your values and intentions. Avoiding these pitfalls requires proactive planning, trusted advice and the discipline to think generationally, not just transactionally. Q: How do you advise clients to balance risk and reward when pursuing long-term growth? Ben-Naim: In my experience, more than 80% of portfolio performance comes from asset allocation. The other 20% comes from the strategic selection of managers. These should be top-tier professionals and sponsors who have long-demonstrated success. Your advisor should not only provide guidance on the makeup of your portfolio but also serve as a reliable conduit, connecting you to well-vetted sponsors – hedge funds, private equity firms and other alternative investment opportunities that can provide buffers in downcycles, participation in bull markets and demonstrate confident returns in five-to-seven-year cycle. For us at IDB, this network of sponsors and managers is of critical importance. We've found that our clients respond incredibly well to our ongoing introductions to high-performance opportunities from both our broker-dealer partner IDB Capital, our joint venture IDB Lido Wealth and outside partners. Pujol: Don't chase high risk, high reward; engineer low risk, high conviction through long-term thinking. At Objective, we believe true risk isn't just about market volatility, it's often about overpaying for uncertain outcomes or fads. Long-term growth starts with disciplined entry and should correlate with what you want to own five years down the line. Valuation at entry isn't just for compliance, it's the defense and roadmap for future position adjustments. We often guide clients to model three – cases, low, base and high – because if you only plan for the base case, you've handicapped your understanding of potential outcomes. The best investors price in imperfection, protect capital on the downside and let time handle the compounding on positive trends. In private markets, we also help clients structure investments with asymmetric outcomes, where a 1× downside supports a 3× upside. That can include preference stacks, convertibility on notes and milestone upside through derivatives like warrants. We always model worst-case cash burn first; if it still makes sense at the bottom, everything else is upside. Valuation is your testing ground. Use it to see clearly and act with conviction. Q: What role does philanthropy play in wealth management today, especially among younger affluent clients? Watson: Philanthropy plays a significant role in wealth management today, especially among younger affluent clients who increasingly seek to align their wealth with their values. Tools like Donor-Advised Funds (DAFs), Trust Accounts and strategic charitable giving offer flexible and tax-efficient ways to support causes they care about. These options allow clients to create lasting impact while maintaining control over their giving strategy, making philanthropy a key part of their overall financial and legacy planning. Q: What are the latest trends in estate planning that individuals and families should be aware of? Driskell: Several emerging trends are reshaping estate planning. First, many families are accelerating wealth transfers ahead of the 2026 estate tax exemption sunset. Tools like SLATs, IDGTs and GRATs are increasingly popular for capturing today's favorable tax climate. Second, planners are focused on trust design that balances asset protection with beneficiary flexibility, including directed trusts and decanting statutes. Third, digital assets – from crypto to intellectual property – require new planning considerations. Finally, estate plans increasingly incorporate non-tax goals, such as family harmony, stewardship and values-based legacy planning. Tailored education and engagement for the next generation is also a growing priority to reduce conflict and enhance readiness for wealth transfer. Q: What estate planning tools are most effective for minimizing tax burdens across generations? Pujol: Standard structuring tools still work, but their true power lies in how and when they're used. For example, gifting pre-appreciated assets during downturns or before liquidity events allows wealth to grow outside the estate at a compressed tax cost. Planning with discount studies for minority positioning can allow you to apply discounts for lack of marketability and control, reducing the taxable value of gifted interests while preserving real economic value. Certain traditional trust structures, including those based on annuity techniques, remain effective planning tools. Their impact can be significantly enhanced by aligning transfers with existing tax benefits, such as Qualified Small Business Stock treatment. When minority interests are gifted at trough valuations and supported by appropriate discounts for lack of marketability and/or control, substantial equity can be shifted into tax-efficient vehicles at reduced reported values. Capture step-ups early may save IRS bills later. This clearly shows compliance valuation is not just part of the plan, it's a real economic multiplier. With early planning, millions in future value can be transferred before massive tax consequences. Driskell: Irrevocable trusts are a cornerstone of multigenerational tax planning. Grantor trusts, such as Intentionally Defective Grantor Trusts (IDGTs), allow parents to sell appreciating assets without triggering income tax, removing future growth from the estate. Spousal Lifetime Access Trusts (SLATs) offer access to income while locking in the current exemption amount. Generation-skipping trusts minimize estate tax exposure across multiple generations. Qualified Personal Residence Trusts (QPRTs) and Grantor Retained Annuity Trusts (GRATs) are useful for freezing asset values. Family Limited Partnerships (FLPs) and valuation discounts further enhance tax efficiency. Coordinating these strategies with lifetime gifts and charitable giving can significantly reduce long-term tax burdens. Q: In what ways should wealth managers prepare clients for potential ripple effects from trade restrictions between major economies? Watson: Wealth managers should prepare clients for potential ripple effects from trade restrictions by helping them assess and adjust their portfolios to mitigate risk. First, they should review global diversification to ensure clients are not overly exposed to any single economy, industry or region, especially those directly impacted by trade restrictions and geopolitical crises. This may involve shifting exposure from vulnerable sectors or countries to more resilient ones. They should also consider incorporating alternative assets that may offer protection in times of geopolitical instability, such as commodities or real assets. Additionally, wealth managers can guide clients on cash flow management and ensure liquidity needs are met, as trade restrictions could lead to economic slowdowns or disruptions in supply chains. Lastly, they should help clients stay informed and proactive, adjusting investment strategies in response to evolving trade dynamics and market conditions. Q: What unique considerations should business owners factor into their estate and succession plans? Pujol: Succession isn't a single event, it's a system that needs to be built, maintained and regularly tested. Business owners and family heads should structure continuity plans with updated valuations, clearly defined buy-sell mechanisms, and governance that depends less on future intentions or personalities and more on thoughtful planning. Uncertainty is one of the biggest threats to enterprise value. If business plans aren't baked into legal documents, the business is exposed to potential family disputes, tax inefficiencies and legal ambiguity. Transfers are also easier when numbers have been agreed to in advance. Plan as if you'll leave tomorrow and revisit that plan at least once a year. More families are treating succession planning like an annual checkup. During year-end valuation work, they run liquidation or 'liquidity fire-drill' scenarios to spot issues and test their transition plans. Some are also using structures to manage control and distributions effectively across family members more dynamically. Like outdated software, if a succession plan isn't reviewed and updated regularly, it's more likely to break when you need it most. Driskell: Business owners face unique risks and opportunities in estate planning. Key considerations include ensuring continuity of control, managing valuation and liquidity issues, and minimizing transfer tax liability. Proper use of buy-sell agreements, voting and non-voting share structures, and family-limited partnerships helps preserve operations while transferring economic value. Owners should explore gifting or selling interests to irrevocable trusts while leveraging valuation discounts. Planning for management succession is equally vital – aligning legal structure with leadership readiness. Owners often underestimate the need to separate governance from ownership. Coordinating business succession with estate liquidity planning (via insurance or redemption strategies) ensures family and business stability. Q: What defensive investment strategies are you recommending in light of the geopolitical instability and trade disputes? Ben-Naim: We consistently review our clients' allocations and advise on defensive strategies that can help ensure a buttoned-up portfolio. These strategies can range from diversifying asset classes to withstand major public market fluctuations, tax incentive investing and hedging. When considering geopolitical instability, our diversification philosophy is much the same. Now is an opportunity to really consider your geographic exposures and to look to consistently performing and emerging markets outside of the U.S. to realize opportunities. Of course, not all markets are winners and investing in a new region requires vetting, oftentimes with boots on the ground. But with careful research, you can make intelligent entry points. For example, despite the war, Israel proved to have a very strong public market in the past 18 months. Other markets, including India and Vietnam, are expected to perform with higher GDP growth compared to the U.S. and present an exciting outlook. Q: How do you see AI and automation impacting wealth management in the next 5-10 years? Pujol: AI is beginning to reshape wealth management, but it's not a replacement for advisors, it's another tool in the toolbox. Used well, it can accelerate diligence, surface outliers, stress test assumptions and generate models in seconds. But the truth is clients don't need more spreadsheets; they need clarity, context and judgment. All this comes from the human touch and experience. The advisors who will lead in the next decade are those who treat AI like an enhancement of their own skills, not like a replacement. At Objective, we use AI to flag inconsistencies, improve our communication and stress test our thinking. Then we bring in the human element to synthesize, challenge and advise. AI can compute outcomes, but it's useless without an experienced human interpreter. In the end, it's not about replacing insight, it's about removing noise so advisors can focus on the decisions that actually matter. AI enhances great advisors, but it will never make poor ones great. Watson: AI and automation are set to significantly impact wealth management in the next 5-10 years, likely accelerating the commoditization of basic advisory services. As technology advances, routine tasks such as portfolio rebalancing, tax optimization and risk assessment will become increasingly automated, making them more accessible and efficient at a lower cost. This will force traditional wealth advisors to rethink their value proposition, as many investment-related services will be handled by AI-driven platforms. To remain competitive, advisors will need to expand their offerings beyond just investments, focusing more on personalized financial planning, estate and tax strategies, and holistic wealth management. By integrating AI and automation into their practice, wealth managers can enhance their operational efficiency, but to truly differentiate themselves, they will need to provide high-touch, value-added services that help clients navigate complex financial decisions and life transitions. Q: How can advisors better engage younger generations in the wealth transfer conversation to avoid conflict and ensure legacy continuity? Pujol: If you want heirs to act like stewards instead of recipients, don't just write a will, start a conversation. The earlier families involve younger generations, the more likely wealth becomes a tool for continuity. We've seen families use business valuations, portfolio reviews and cash flow summaries to bring clarity to the 'why' behind the wealth and to tell the full story to their heirs. These tools take emotion out of the equation and turn complex financial decisions into documented, teachable moments. A detailed valuation can start the conversation a trust document cannot. One strategy that works well is forming a Family Investment Committee before the age of 18. You can even give heirs mock capital, or even small portfolios, and let them pitch investments quarterly, benchmarking their results against the real portfolio. Valuation reports and shared KPIs can turn wealth into something they understand and feel responsible for. The more context you provide while living, the fewer misunderstandings arise after you're gone. Driskell: Engaging younger generations early promotes transparency, reduces conflict and builds legacy alignment. Advisors should encourage family meetings to share the purpose behind planning decisions, including family values and long-term goals. Incorporating educational components – like basic financial literacy, investment principles and trust mechanics – empowers beneficiaries and fosters stewardship. Structuring trusts to provide phased access, beneficiary-directed investment input or co-trustee roles can build confidence and responsibility. Additionally, encouraging philanthropy and impact investing can bridge generational gaps. Above all, advisors must create space for open dialogue, ensuring younger family members feel heard and respected. This relational foundation is often more critical than the legal structures themselves. Watson: Advisors can better engage younger generations in the wealth transfer conversation by fostering early, inclusive and values-driven dialogue within families. Rather than treating wealth as a taboo or distant topic, advisors should encourage clients to involve heirs in strategic conversations about family values, financial goals and the purpose behind the wealth. This helps build trust, reduce the risk of conflict and ensures that the next generation feels informed and empowered rather than surprised or unprepared. Advisors can also offer educational resources and facilitate family meetings to bridge knowledge gaps and align expectations. By acting as neutral facilitators and emphasizing transparency, advisors play a key role in preserving both family harmony and the long-term continuity of the legacy. Q: For those concerned that their heirs might abuse their inheritance, what trust strategies are there? Driskell: Discretionary trusts with independent trustees remain a powerful tool to prevent misuse of inherited wealth. These trusts allow the trustee to make distributions based on the beneficiary's needs rather than mandatory rights. Incentive provisions can be included to reward education, employment or sobriety. Spendthrift clauses protect trust assets from creditors and poor financial decisions. Advisors may recommend staggered distributions or milestone triggers to gradually release funds. For families with ongoing concerns, directed trusts or trust protectors can provide oversight and flexibility. Ultimately, thoughtful drafting and selecting a fiduciary who understands family dynamics are key to protecting both wealth and relationships. Q: As a trusted advisor, what advice can you share for longer-term portfolio asset allocation? Ben-Naim: Now more than ever, high-net-worth investors have access to more asset classes, opportunities and strategies. While this is exciting, it's important to understand the implications of your holdings and to allocate your portfolio in a way that will withstand external fluctuations. It can be nearly impossible to understand the implications of your full portfolio holdings and how they may fluctuate throughout a market cycle or in response to a macroeconomic, geopolitical or industry event. I strongly recommend working with an advisor with a fiduciary responsible to you and your best interests, as well as intimate working knowledge of your profile, family, businesses and interests in order to create the right plan. The right financial advisor will not only know and understand you and your allocations but will also prioritize consultancy and communication to ensure holistic success.
Business Insider
an hour ago
- Business Insider
Stock Market News Review – Stock Futures Dip with Key Events Ahead
U.S. stock futures slightly dipped on Sunday evening, with the S&P 500 (SPX) hovering just below record territory. Futures on the Nasdaq 100 (NDX), the Dow Jones Industrial Average (DJIA), and the S&P 500 were down 0.14%, 0.04%, and 0.07%, respectively, at 8:06 p.m. EST, June 8. Confident Investing Starts Here: Meanwhile, all three major indexes finished their second winning week in a row. The S&P 500 ended above 6,000 for the first time since February 21 and is now less than 3% below its all-time closing high. This week starts off busy, with U.S. and China officials holding trade talks in London and Apple (AAPL) kicking off its 2025 Worldwide Developers Conference today. Later in the week, investors will watch closely for fresh inflation data, with May's Consumer Price Index (CPI) due Wednesday and May's Producer Price Index (PPI) on June 12, Thursday.
Business Insider
2 hours ago
- Business Insider
Short Report: Short interest in Clear Secure hits record high
Welcome to this week's installment of 'The Short Interest Report' – The Fly's weekly recap of short interest trends among some of the most widely followed high-short-float stocks. Using the data from our partner which utilizes the latest information from stock lenders to estimate short interest changes for thousands of publicly traded companies, this report will screen for some of biggest changes in short interest as a percentage of free float and days-to-cover ratios while also considering the short interest data on some of the more volatile and heavier-traded names of the week. Based on the availability of data from Ortex, the report tracks the trading period that covers prior Friday through Thursday of this week, excluding holidays. As a basis of comparison for stocks discussed below, the S&P 500 index was up 0.5%, the Nasdaq Composite was up 0.6%, the Russell 2000 index was up 1.2%, the Russell 2000 Growth ETF (IWO) was up 2.0%, and the Russell 2000 Value ETF (IWN) was up 0.3% in the five-day trading session range through June 5. Confident Investing Starts Here: SHORT INTEREST GAINERS Ortex-reported short interest in Hims & Hers (HIMS) hit a record high of 37.6% in the first week of May as bears questioned the rebound in shares over the prior two weeks. With the sharp bounce persisting into mid-May – the stock ended up more than doubling from mid-April to May 14 peak – shorts then reduced their exposure to just north of 30%. This week however, bearish appetite in this volatile name has resurfaced. Shorts as a percentage of free float rose from 30.7% to 33.6% and days-to-cover was up from 1.2 to 1.6 even though trading volumes remained steady. The stock was up less than 1% in the five-day period covered through Thursday, but inclusive of Friday's 6.8% jump, shares are now up 133% year-to-date. Ortex-reported short interest in Clear Secure (YOU) had tracked sideways in a 20.5%-23.5% range from mid-February through the final week of April, though bearish appetite has picked up notably through May and into June even though the stock has traded without much conviction on either side. In the five-day period covered, shorts as a percentage of free float rose from 27.2% to 29.3% – a record high, while days-to-cover reached a three-month high with a 90 basis point advance to 6.5 amid thinner volume. Shares were up 6.8% in the five-day period covered, though year-to-date, Clear Secure shares are still down about 2%. Ortex-reported short interest in Designer Brands (DBI) troughed around 23% in the final week of April but has since shot higher in spite of the bounce in the stock price. This week, shorts as a percentage of free float jumped from 27.7% to 32.2% – the highest level in nearly five months. Likewise, despite the steady levels of trading volume, days-to-cover on the name also shifted notably, rising from 4.9 to 8.4. Ahead of Designer Brands' Q1 results on deck for next week, over the five-day period covered through Thursday, the stock rose 1.1% and relative to its April lows, shares are up 57% – inclusive of Friday's 5% gain. Year-to-date, the stock is still down 28.5%. Ortex-reported short interest in Gogo (GOGO) had started its collapse from high-altitude levels above 30% to less than 27% in mid-March when the company disclosed a Supplemental Type Certificate FAA approval for its tail mount terminal for Gulfstream aircraft, sending its stock higher by 25% within a week. Bearish positioning was then dealt a blow in early May when the company's Q1 results and affirmed guidance also featured the disclosure of a PMA – Parts Manufacturer Approval – for its Galileo FDX antenna, sending short interest down to fresh seven-month lows below 26%. This week, short-covering momentum continued, with shorts as a percentage of free float falling another two and a half points 21.8% – the lowest level since late October. Meanwhile, the stock picked up about 3% in the five-day period covered this week and also has now registered a 37% gain year-to-date. Last week, Ortex-reported short interest in AST SpaceMobile (ASTS) reached the highest level since late March of around 30%. This week however, shorts as a percentage of free float shrunk to 25.5%, while the stock staged a steep 30% jump in the five-day period covered. Driving short-sellers to the exits was an Instagram post by AST SpaceMobile board member Adriana Cisneros titled 'Amazing things are happening at AST & Science + @blueorigin', which has elevated speculation that Amazon's Jeff Bezos might become an ASTS investor. Year-to-date, AST SpaceMobile shares are now up about 48%.
