Inside Long Angle’s 2025 Sonoma Retreat and 2026 Preview
Written By: Ryan Morrison
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The Long Angle 2025 Annual Retreat brought 250 members to Sonoma, California for 3.5 days of substantive programming, genuine peer connection, and the kind of candid conversation that rarely happens in any other room. Keynotes from Guy Raz and Kai Ryssdal anchored the agenda. Sessions on estate planning, private markets, insurance strategy, and women's health delivered real, applicable insight. An evening at Jacuzzi Winery, dueling pianos under the stars, and sunrise hikes filled the time in between.
This post covers what happened, what members learned, and what is coming next. The 2026 Long Angle Retreat is currently open for registration, available exclusively to members.
Watch the recap
This short video captures the highlights.
Key Takeaways
250 members attended the 2025 Long Angle Retreat in Sonoma, California, September 28 to October 1
Keynote speakers included Guy Raz (How I Built This, TED Radio Hour) and Kai Ryssdal (Marketplace)
Sessions covered advanced estate planning, private markets allocation, insurance strategy for high-net-worth individuals, and women's midlife health
Social programming included a private dinner at Jacuzzi Winery, dueling pianos, and sunrise hikes
Retreat Circles opened the event with structured small-group peer pairings, so no one spent the first day figuring out who to talk to
The 2026 Retreat is coming to Hyatt Regency Lost Pines, Cedar Creek, Texas, in September 2026
What Is the Long Angle Annual Retreat?
The Long Angle Annual Retreat is a members-only event held every year bringing together high-net-worth entrepreneurs, investors, and professionals for 3.5 days of programming, peer connection, and social activities. Lodging, meals, and all events are included in the ticket price.
The Retreat is not a conference. It is not a networking event. It is one of the biggest moments each year when the Long Angle community moves offline and into the same building. Members who have spent months exchanging notes on the platform meet in person. Those conversations go deeper faster because the trust was already there.
The format has scaled deliberately. The inaugural Retreat in Scottsdale drew 150 members from 10 countries. Sonoma brought 250. Austin 2026 is targeting 350. Each year, the attendance grows. The intimacy has held because of one structural mechanism: Retreat Circles Live.
Retreat Circles open the event on the first afternoon. Every attendee is paired into a small group and spends an hour sharing what they are hoping to get out of the Retreat and what they are navigating in their lives. By the time the welcome dinner begins, no one is a stranger. Members who attended have described the experience as something close to the first week of college: the unusual, disarming feeling of being in a room full of people you have not met yet but with whom you already have something real in common.
Sonoma 2025: The Setting and the People
The 2025 Retreat was held September 28 to October 1 at the Fairmont Mission Inn and Spa in Sonoma, California. Two hundred and fifty members attended from across the United States and internationally.
Guy Raz, creator and host of NPR's How I Built This and TED Radio Hour, delivered one of the two headline sessions. In a fireside chat moderated by Long Angle Managing Director Tad Fallows, Raz traced his career from war correspondent to podcasting pioneer and made a case that curiosity, not intellect, is the true engine of entrepreneurial success. He argued that professional setbacks are often the pivots that matter most, a point he made from personal experience, having built his most impactful work after being passed over for a major role he coveted. In a room full of founders and operators, the observation landed.
Kai Ryssdal, host and senior editor of Marketplace, brought a different register to the stage. His session drew on years of covering the American economy to surface the patterns that tend to be invisible until they are obvious in hindsight, which is exactly the kind of perspective this audience comes to the Retreat to hear.
Recommendations made from the stage or across the dinner table carried the weight they carry in Long Angle's community: the person recommending had nothing to gain except credibility.
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What We Learned: Session Highlights
The four sessions below were among the most substantive of the Retreat. Each one went deep enough to be useful well beyond the room.
Advanced Estate Planning
Chris Nason of McDermott Will and Emery returned to the Retreat for a second year, building on his foundational session from 2024 to walk members through the techniques used to transfer significant wealth across generations in a tax-efficient manner. His core premise: the goal of advanced estate planning is not to minimize taxes in a given year but to remove assets from your taxable estate entirely, so the 40% federal estate and gift tax never touches them again.
The foundation is the irrevocable grantor trust. Nason explained that by structuring a trust so the grantor remains responsible for paying income taxes on the trust's earnings, those tax payments function as an unlimited, tax-free gift to the trust each year. The IRS treats them as the grantor paying their own liability. Economically, they are an ongoing transfer of wealth. The trust grows unencumbered while the grantor's taxable estate shrinks.
From that foundation, Nason detailed two workhorses. The first is the Sale to an Intentionally Defective Grantor Trust (IDGT). After seeding the trust with an initial gift, the grantor sells assets to it in exchange for a promissory note bearing the low IRS-mandated interest rate. All appreciation above that rate accrues to the trust free of gift and estate tax. Because it is a grantor trust, the transaction triggers no capital gains. The second is the Grantor Retained Annuity Trust (GRAT), which he called the "least controversial" advanced technique, noting that Sheldon Adelson used it to transfer an estimated $7 billion tax-free. The GRAT transfers assets to a short-term trust while the grantor retains an annuity. Any investment growth above the current IRS interest rate (4.6% at the time of the session) passes to beneficiaries completely free of gift tax. Nason described it as a "heads, you win; tails, you don't lose" structure, particularly well suited to volatile assets.
He also addressed the family office question that comes up repeatedly among members with concentrated wealth. For families with $25 million or more in investable assets, establishing a formal family office structure can make investment advisory fees, legal fees, and fund management fees deductible as business expenses, a benefit no longer available to individual investors. The 2026 estate and gift tax exemption of $15 million per individual makes the planning window meaningful, but Nason's point was consistent with what Long Angle members hear repeatedly: the value of advanced planning comes from starting before the assets have already appreciated, not after.
Beyond the 60/40 Portfolio
Long Angle VP of Investments Patrick Nolan and Managing Director Matt Shechtman presented a systematic case for why the traditional 60/40 allocation has become structurally inadequate, and what a more resilient portfolio looks like in practice.
They identified three headwinds facing the classic model. First, muted expected returns: current valuations imply only a 5.4% 10-year annualized return for a 60/40 blend. Second, a breakdown in diversification: the historically negative correlation between stocks and bonds has turned positive, meaning bonds no longer reliably cushion equity drawdowns. Third, negative real income: the 60/40 portfolio's real yield sits at -0.4% after inflation.
Their argument for private markets was structural, not promotional. The number of publicly listed U.S. companies has declined by more than 30% from its peak. The median age of a company at IPO has nearly doubled to 14 years. The most dynamic phase of corporate growth now happens while companies like OpenAI, Stripe, and SpaceX are still private. Meanwhile, the S&P 500 has become dominated by a handful of mega-cap stocks that account for 34% of the index's total market cap, masking underlying weakness in the other 493 companies.
One member presented his own portfolio as a real-world case study. His primary goal, he told the room, is not outperformance. It is resilience: building a portfolio that lets him sleep at night. His allocation spans multiple asset classes across public and private markets, and over the long term has modestly outperformed the S&P 500. But his point was not the return figure. His best-performing asset over the prior two years was one he held as a hedge against monetary policy uncertainty, not as a high-conviction bet. That outcome, he said, illustrated the real purpose of diversification: preparing for an unknowable future, not predicting it. Members interested in how peers at this wealth stage are allocating can find current benchmark data in Long Angle's annual asset allocation report.
Insurance Strategy for High-Net-Worth Individuals
Mike Lloyd of Pine View Insurance Group opened his session by walking through the seven forces driving personal insurance premiums higher: climate change, continued development in high-risk areas, economic inflation, social inflation (a 57% increase in liability claim costs over the past decade from nuclear verdicts), regulatory failures (particularly in California, where Proposition 103 prevents carriers from charging actuarially sound rates), a "combined ratio" above 100% for most carriers (meaning they are paying out more than they collect), and Treasury yields so attractive that new capital has little incentive to enter the insurance market.
His practical framework cut through the complexity. The central principle was that self-insurance is smart insurance for high-net-worth individuals. The mistake Lloyd sees repeatedly is spending premium dollars insuring against losses that are easily absorbable and underinsuring against the ones that are not.
On the savings side: raise home and auto deductibles to at least $10,000. Pay small damages out of pocket. Lloyd was emphatic about avoiding small claims. Filing a claim under $20,000, he said, can make a person "completely uninsurable," even if the claim is straightforward. A history of small claims signals risk to carriers in ways that are disproportionate to the actual dollar amounts involved.
On the spending side: invest in a high-limit umbrella liability policy from a top-tier carrier. He compared standard carriers to Spirit Airlines and high-net-worth carriers like Chubb and PURE to Delta first class. The difference is not just coverage language. It is claims handling and access to the carrier's legal resources when a serious lawsuit arrives. He closed with two cautionary examples, neither fictional: a founder who exited a company and insured a Ferrari at state-minimum limits, and a Harvard Business School graduate whose home was underinsured by nearly $2 million. The insurance that looks like savings on the front end has a way of becoming the most expensive decision in the portfolio.
Women at the Peak: Health, Energy, and Edge in Midlife
Stephanie Tilenius, founder and CEO of Peak Health and a former senior executive at Google and PayPal, delivered the session that generated the most conversation in the hallways after. Her argument was direct: menopause is not a life stage to be managed. It is a systemic health event that demands the same proactive, data-driven approach that serious investors bring to their portfolios.
She opened with the number that anchors the problem: only 4.7% of women who need hormone therapy are receiving it. She traced that gap directly to the misinterpretation of the 2002 Women's Health Initiative study, which used synthetic hormones in an older population and was widely read as evidence that hormone therapy was dangerous for all women. Tilenius called it "one of the biggest mistakes in health history."Subsequent research has made clear that the findings were misapplied, but a generation of women and their physicians absorbed the fear and the prescribing patterns followed.
The consequences are not cosmetic. As estrogen levels decline by roughly 80% through menopause, LDL cholesterol rises an average of 19%, bone loss accelerates, insulin resistance increases, and brain metabolism slows in approximately 80% of women. Women have double the rate of Alzheimer's disease compared to men. Heart disease is the leading cause of death in women, and the risk shifts sharply after menopause. Tilenius's case was that waiting for symptoms to appear before intervening is the wrong frame. The biology is moving well before the symptoms arrive.
Her practical framework started with testing: a DEXA scan for bone density starting at 40 (not the standard 65), a coronary artery calcium (CAC) score by 45, and comprehensive blood panels that include ApoB and Lipoprotein(a), markers that standard panels typically omit. On lifestyle: resistance training three to four times per week and one gram of protein per pound of body weight daily to counter the muscle loss that accelerates through this transition. On advocacy: she shared that when she surveyed a Stanford-affiliated OB-GYN practice, only one physician out of twelve was being trained in modern menopause care. Women who want current, evidence-based treatment often need to arrive at appointments prepared to ask for specific tests and to push back on dismissive responses.
The session was designed for women but was not attended only by women. Several members noted afterward that the conversation changed how they thought about their own family's healthcare decisions and what questions to bring to upcoming appointments.
Social Programming and Evening Events
The sessions were where members came to learn. The evenings were where the retreat became something else.
On the second night, the group gathered for a private dinner at Jacuzzi Winery in Sonoma. Long tables, wine country in October, and 250 people who had just spent an afternoon in Retreat Circles getting unexpectedly candid with strangers. The conversation that followed was different from a typical event dinner because the warming-up had already happened.
The third evening brought dueling pianos under the stars. It is the kind of activity that sounds like a concession to fun on a conference agenda and turns out to be the thing people remember most. Someone from a PE-backed startup and someone from a family office who had been debating private credit allocation at 4pm were at the same piano sing-along at 9pm. Those connections tend to last.
Sunrise hikes ran each morning for members who wanted them. Optional, early, and apparently popular. The members who showed up at 6am for a hike in Sonoma in late September were, by most accounts, in good spirits throughout the day.
The common thread in what members described afterward was not the agenda. It was the room. The same people who spent a session drilling into GRAT mechanics or debating the 60/40 critique were at dinner telling stories and at the piano laughing. Long Angle members are high achievers with full lives, and the Retreat is one of the few places where those two parts of life are in the same room at the same time.
Coming in 2026: Austin, Texas
The 2026 Long Angle Annual Retreat will be held in September 2026 at Hyatt Regency Lost Pines, Cedar Creek, Texas, just outside Austin. The target attendance is 350 members.
What is included: lodging at Hyatt Regency Lost Pines Resort and Spa, all meals and refreshments, full programming including keynote sessions, fireside chats, panels, and workshops, Retreat Circles Live on the opening afternoon, and evening social activities.
Attendance is capped at 250 rooms on a first-come, first-served basis. Spouses and partners are welcome and encouraged. The event is adults-only. Questions can be directed to Hanna Heffern at hanna.heffern@longangle.com.
The Retreat is open to Long Angle members. For those who are not yet members, you can take the first step and apply for membership.
Looking for a peer community that goes beyond the portfolio?
Long Angle is a private, vetted community of high-net-worth entrepreneurs and professionals comparing notes on everything from estate planning to post-exit identity, without solicitation.
Frequently Asked Questions
What is the Long Angle annual retreat?
The Long Angle Annual Retreat is a members-only, all-inclusive event held each fall. It brings 250+ high-net-worth entrepreneurs, investors, and professionals together for 3.5 days of keynote sessions, peer-led breakouts, Retreat Circles, and social activities. Lodging, meals, and programming are included in the ticket price.
Who can attend the Long Angle retreat?
The Retreat is open to Long Angle members only. Long Angle is a vetted community for high-net-worth individuals, typically with a net worth of $2.2 million or more. Spouses and partners of members are welcome and encouraged to attend. The event is adults-only. To attend a future retreat, the first step is applying for Long Angle membership.
What topics are covered at the Long Angle retreat?
Programming covers both financial and lifestyle topics. The 2025 Retreat included sessions on advanced estate planning (dynasty trusts, GRATs, IDGTs), private markets allocation and the case against the 60/40 portfolio, insurance strategy for high-net-worth individuals, and women's midlife health. Keynote sessions featured Guy Raz and Kai Ryssdal. Social programming included a private winery dinner, dueling pianos, and sunrise hikes.
What is included in the Long Angle retreat ticket price?
All tickets include lodging, all meals and refreshments, full programming, Retreat Circles, and evening social activities. Travel costs are not included.
When and where is the 2026 Long Angle retreat?
The 2026 Long Angle Annual Retreat will be held in September 2026 at Hyatt Regency Lost Pines Resort and Spa in Cedar Creek, Texas, just outside Austin. Attendance is capped at 250 rooms on a first-come, first-served basis.
Final Thoughts
The 2025 Retreat demonstrated something the community already knew and needed to see in person again: the quality of a room is not an abstraction. It is the person next to you at the winery dinner who ran a company you admire, the person on the sunrise hike who has navigated the exact trust structure you are trying to figure out, and the person at the piano who has been in your situation and wants to compare notes. That is what 250 members built together in Sonoma. Austin is next.
Want to be in the room next year?
“The annual retreat was like the first week of freshman year in college, where I can sit at any table and feel welcomed into a conversation.” Become a Long Angle member today to learn more about our annual member-only retreat.
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