https://familybusinesses.com/2026-09-29 https://familybusinesses.com/answers/2026-09-29 https://familybusinesses.com/apply2026-09-29 https://familybusinesses.com/books2026-09-29 https://familybusinesses.com/tools/2026-09-29 https://familybusinesses.com/tools/family-business-claude-skill/2026-09-29 https://familybusinesses.com/glossary2026-09-29 https://familybusinesses.com/library2026-09-29 https://familybusinesses.com/my-family-business2026-09-29 https://familybusinesses.com/trail-guide2026-09-29 https://familybusinesses.com/university-programs2026-09-29 https://familybusinesses.com/family-equity2026-09-29 https://familybusinesses.com/fireside-chats/2026-09-29 https://familybusinesses.com/playbooks/selling-the-business/2026-09-29 https://familybusinesses.com/playbooks/growth-capital-and-refinancing/2026-09-29 https://familybusinesses.com/playbooks/next-generation-grooming-mode/2026-09-29 https://familybusinesses.com/playbooks/dad-or-mom-needs-to-let-go/2026-09-29 https://familybusinesses.com/playbooks/governance-and-family-values/2026-09-29 https://familybusinesses.com/playbooks/passing-wealth-down/2026-09-29 https://familybusinesses.com/playbooks/creating-your-family-office/2026-09-29 https://familybusinesses.com/playbooks/investing-in-family-businesses/2026-09-29 https://familybusinesses.com/playbooks/what-is-my-company-worth/2026-09-29 https://familybusinesses.com/answers/best-quotes-about-family-business/2026-09-29 https://familybusinesses.com/answers/bringing-in-non-family-executives-and-board-members/2026-09-29 https://familybusinesses.com/answers/family-businesses-done-well-examples/2026-09-29 https://familybusinesses.com/answers/how-family-business-owners-get-more-deal-flow/2026-09-29 https://familybusinesses.com/answers/how-to-groom-heirs-to-lead/2026-09-29 https://familybusinesses.com/answers/how-to-handle-conflict-in-a-family-business/2026-09-29 https://familybusinesses.com/answers/how-to-pass-down-values-not-just-money/2026-09-29 https://familybusinesses.com/answers/how-to-pay-and-promote-family-members/2026-09-29 https://familybusinesses.com/answers/how-to-plan-succession-and-hand-the-business-to-the-next-generation/2026-09-29 https://familybusinesses.com/answers/how-to-prepare-kids-for-wealth/2026-09-29 https://familybusinesses.com/answers/lessons-for-first-generation-founders/2026-09-29 https://familybusinesses.com/answers/my-father-and-what-he-taught-me/2026-09-29 https://familybusinesses.com/answers/raising-growth-capital-without-losing-control/2026-09-29 https://familybusinesses.com/answers/sell-the-family-business-or-keep-it/2026-09-29 https://familybusinesses.com/answers/wealth-preservation-versus-risk-taking/2026-09-29 https://familybusinesses.com/answers/what-good-family-governance-looks-like/2026-09-29 https://familybusinesses.com/answers/what-multi-generational-families-do-differently/2026-09-29 https://familybusinesses.com/answers/when-to-start-a-family-office/2026-09-29 https://familybusinesses.com/essays/ask-questions-first/2026-09-29 https://familybusinesses.com/essays/family-office-buyer-vs-private-equity-buyer/2026-09-29 https://familybusinesses.com/essays/financial-iq/2026-09-29 https://familybusinesses.com/essays/how-do-you-know-its-a-good-deal/2026-09-29 https://familybusinesses.com/essays/rewarding-your-key-people/2026-09-29 https://familybusinesses.com/fireside-chats/e9-6pghDnVo/2026-09-29https://i.ytimg.com/vi/e9-6pghDnVo/hqdefault.jpgWe really wanted both of our boys to make decisions and make mistakes.David McWhirter started a welding business in his garage on his 22nd birthday in 1992, after turning down a job offer from Northrop, and grew it into a 75-employee structural steel company. He credits military discipline, heavy reinvestment in equipment and people instead of cars and lifestyle, and relationships that produced referrals. His son Nathan describes working backwards from revenue goals, hiring the right person at the right time, and earning authority with long-time employees through humility and results. David's biggest founder mistake was being involved in everything, and the business improved once he showed his people he trusted them to decide. For families grooming a successor, the pair's rule is to let the next generation make real decisions and real mistakes.https://www.youtube.com/embed/e9-6pghDnVo11002026-04-16 https://familybusinesses.com/fireside-chats/iecqp1zYYs8/2026-09-29https://i.ytimg.com/vi/iecqp1zYYs8/hqdefault.jpgAsian families with children studying in the U.S. join a next-generation mentorship program.The founder of a boutique cross-border family office advisory firm runs a next-generation mentorship program for clients' children, aged about 20 to 35, who are studying or working in the United States, bringing them together to discuss family wealth stewardship, the U.S. business environment and succession. After 11 years at two single family offices in oil and gas, media, sports and healthcare, the founder started the firm a year earlier and has onboarded three families from Asia, in oil and gas, renewables and retail technology. The firm connects Asian capital with U.S. investments and is helping two client families bring their businesses onshore in the United States. The founder also notes that the Chinese government recently pushed about $140 billion into venture capital.https://www.youtube.com/embed/iecqp1zYYs83422026-08-21 https://familybusinesses.com/fireside-chats/E0aZo6GRjfg/2026-09-29https://i.ytimg.com/vi/E0aZo6GRjfg/hqdefault.jpg95% of what is out there in family office structures is flawed.Thomas Handler, a trust, estate and tax attorney for close to or over 40 years, says 95% of the family office structures he sees are flawed. He has personally represented more than 130 billionaires and worked on about 600 family offices, starting with a $5.5 billion Japanese family now in the $45 billion range. He notes that almost 90% of family offices are C corporations and describes a client whose LLC partnership family office bought a $14 million jet, wrote off 100% of it, and later sold it for a $4.5 million profit. He advises families to hold 10% of net worth in a trust outside the United States, citing an Iowa family worth over $700 million that declined South Dakota trusts and Delaware LLCs and later went bankrupt. A proper team, in his view, includes international and domestic tax lawyers, an executive compensation or ERISA lawyer, a multi-entity business planner, a corporate lawyer and a trust and estate lawyer.https://www.youtube.com/embed/E0aZo6GRjfg20092026-07-02 https://familybusinesses.com/fireside-chats/9_zzaOl5Lw0/2026-09-29https://i.ytimg.com/vi/9_zzaOl5Lw0/hqdefault.jpgMost people do not speak to Gen 2 or Gen 3 with enough respect.Panelists at the Beverly Hills Investor Club Summit say the next generation gets ready by being in the room early and by being given real responsibility. One second-generation panelist, whose widowed mother took her to banks and attorneys' offices after her father died when she was 8, now has her two sons run her crypto and blockchain portfolio. Another panelist argues that most people do not speak to Gen 2 or Gen 3 with enough respect, and that their value may not be running the company. A third family brings its children to conferences and meetings, bans phones while they are with the parents, teaches eye contact, and asks the kids what they follow on TikTok and Instagram. The common thread is finding an interest the next generation has that is investable and building their involvement around it.https://www.youtube.com/embed/9_zzaOl5Lw04532026-04-25 https://familybusinesses.com/fireside-chats/cuTLcmphEIQ/2026-09-29https://i.ytimg.com/vi/cuTLcmphEIQ/hqdefault.jpgThere's always somebody more successful and somebody wealthier than you, so don't try to prove something.A panelist reminds the room that there is always somebody more successful and wealthier, so no one should sit down with an investor trying to prove something. The panel includes an outsourced multi-family office serving small and mid-sized families before a liquidity event, with a focus on estate planning, succession and wealth transfer; a representative of Sunburst Ventures, her family's office in Florida and Puerto Rico; and a co-founder of Core Family Office, which has built nine portfolio companies since 2017 to serve its clients. The Core Family Office co-founder advises founders not to pitch too hard and to show what they actually have and care about, because integrity, transparency and honesty are what make his firm want to work with someone. Another panelist runs an investment bank focused on sustainable energy, materials and transportation.https://www.youtube.com/embed/cuTLcmphEIQ4932026-04-24 https://familybusinesses.com/fireside-chats/4FxxM_WuywU/2026-09-29https://i.ytimg.com/vi/4FxxM_WuywU/hqdefault.jpgThey exited for $2.2 billion by focusing on lifetime value, not just acquisition cost.Kevin Harrington, an original Shark Tank investor and pioneer of the infomercial, says companies scale by focusing on customer lifetime value rather than only acquisition cost, citing a company that turned a $39 sale into an average of eight purchases, about $300, and later exited for $2.2 billion. He has launched more than 500 products with over $5 billion in sales in more than 100 countries, and 20 of his businesses passed $100 million. He joined the Celsius board 12 years ago when the stock traded at 22 cents and the company was worth under $10 million, and he says it is now a $12 billion company. Early in his career he bought six hours of overnight airtime on Discovery for $350,000 a year, and his company grew from zero to $500 million. Today he invests alongside his son, his brother, his brother's daughter and a partner, Brandon Adams.https://www.youtube.com/embed/4FxxM_WuywU16732026-04-18 https://familybusinesses.com/fireside-chats/f6BBX_UVH2g/2026-09-29https://i.ytimg.com/vi/f6BBX_UVH2g/hqdefault.jpgBy generation three there's a loss of the family ethos, and the family office splinters.A private family trust company protector on the panel says that by the third generation many families lose the family ethos, live off the wealth and splinter, and he cites a 92% failure rate for family offices and businesses that do not invest in deliberate interventions. His recommendations include engaging trust protectors so trusts function as the wealth creators intended, practicing seven-generation thinking, and funding family retreats and properties through trusts built around family activities rather than beneficiaries. A multifamily investor says his firm went pencils down in 2022 and 2023 and is now buying distressed properties for about 40% of their 2022 prices, after raising about $10 million in 30 days. Another panelist who made his wealth creating music for film and TV now buys 28 to 50 unit buildings and sells them off as condos. A third illustrates the cost of a bad deal: $100,000 compounded at 10% for 30 years would grow to about $1.7 million.https://www.youtube.com/embed/f6BBX_UVH2g17022026-04-15 https://familybusinesses.com/fireside-chats/AP6blBsbmrg/2026-09-29https://i.ytimg.com/vi/AP6blBsbmrg/hqdefault.jpgTell us who you are, how you've failed and what you learned before asking to partner.A panelist lays out what $1 billion+ investors want before they partner with someone: who the person is, how they have failed and what they learned, and what cadence they will keep, adding that if a partner cannot provide access and expertise and make the investor stronger, the investor is not interested. The panel includes an investment committee member of a multi-family office in Lehi, Utah, a firm that started as a single family office 10 years ago and has deployed close to $1 billion in originations and credit, and a real estate platform with a little over $2.2 billion in assets across 21 states. One M&A-focused panelist with 45 years of experience says his sweet spot is deals of $25 million to $300 million. Another panelist, who helps founders write legacy books that capture their origin story and leadership philosophy, says alignment with partners, and even a spouse, can make or break a new venture.https://www.youtube.com/embed/AP6blBsbmrg7252026-04-03 https://familybusinesses.com/fireside-chats/c3GphLRoPW0/2026-09-29https://i.ytimg.com/vi/c3GphLRoPW0/hqdefault.jpgOur prime mission is to keep a family together and not let wealth destroy it.Kip Kolson of Family Wealth Leadership, a multi-family office he runs with his son, says his prime mission is to keep families together and not let wealth destroy them. The firm focuses on families between about $25 million and $300 million, because families above that level tend to want a single family office, and it invests across the board, often through funds, including structured settlements that have returned 10% to 17%. He helps clients create and operate both a family office and a family foundation, and encourages boots-on-the-ground philanthropy: a family trip to drill a water well or build a school will be remembered 20 years later in a way a Disney World vacation will not. He warns that giving children everything can deprive them of self-respect, and that being in a wealthy family is difficult for many young people today.https://www.youtube.com/embed/c3GphLRoPW05212026-03-18 https://familybusinesses.com/fireside-chats/D-jC4lfhBgc/2026-09-29https://i.ytimg.com/vi/D-jC4lfhBgc/hqdefault.jpgWealth attracts predators, so elderly family members need protection from scams and undue influence.Mitzi Perdue warns that wealth attracts predators and that elderly relatives are particular targets, citing figures that 10% of 60-year-olds have mild cognitive decline and one in three 85-year-olds has dementia. Her family has agreed that no changes to a will are valid unless witnessed by approved people, and she has a witnessed document naming her sister, brother and lawyer for that role. She describes how a scammer gradually took about $1.5 million from her sister over 12 years, and how a trusted employee of another family gave herself and friends $10,000 bonuses from a checkbook she controlled. Her rules include never giving employees check-writing privileges, segregating bank accounts and having trusted eyes review checks. After media reports valued her at $17 billion, law enforcement warned her she would be targeted, and she turned to security specialists for help.https://www.youtube.com/embed/D-jC4lfhBgc8672026-03-14 https://familybusinesses.com/fireside-chats/sN75-gzmJpE/2026-09-29https://i.ytimg.com/vi/sN75-gzmJpE/hqdefault.jpgVery wealthy people are often quite cheap, especially if they earned the money themselves.Dr. Alexandra Cook, a second-generation family office executive at Sunburst Ventures, says very wealthy people are often quite cheap, especially if they earned the money themselves, so a business deal has to show clear value rather than appeal to a stereotype of lavish spending. She recalls a family she worked for early in her career whose principal repeated the mantra that the office never buys paper clips, and a family that painted a dome themselves for about $1,000 after being quoted $70,000. Cook, who graduated college at 18 as valedictorian and has more than 30 years in finance, operations and private investing across Florida and Puerto Rico, regularly talks through goals and successes with her sons, who are in business with her. Her advice on trust is to demonstrate it to family members, key employees and partners by letting them make decisions, because an owner who is too controlling gets in everyone's way.https://www.youtube.com/embed/sN75-gzmJpE13362026-03-07 https://familybusinesses.com/fireside-chats/DBsIPtWAsGg/2026-09-29https://i.ytimg.com/vi/DBsIPtWAsGg/hqdefault.jpgMy grandchildren's grandchildren will still be developing that piece of land.Joel Nagel, an international tax and corporate lawyer who started his firm in 1992, says the 3,000-acre property his family office bought in Central America in 2000 for about $3 million has only been about 10% developed, and his grandchildren's grandchildren will still be developing it. He says that in 36 years no client has lost a penny through the legal structures his firm created, and that his practice works in about 43 countries. His family office has interests in banking, insurance, real estate development, hospitality and timber, grew from a 1990s mortgage company into a bank in the early 2000s, and includes the Vienna Vikings, a European pro football team. Serving on about 25 boards globally showed him the same problems repeating across countries and businesses. He views Bitcoin as a long-term holding for his children and grandchildren.https://www.youtube.com/embed/DBsIPtWAsGg13672026-02-21 https://familybusinesses.com/fireside-chats/FrVa-TaXpZk/2026-09-29https://i.ytimg.com/vi/FrVa-TaXpZk/hqdefault.jpgOil and gas investments have historically built generational wealth, and the key is patience.Rey R.T. Trevino III, president of Pecos Valley Partners and a third-generation oil and gas investor, says the key to building generational wealth in energy is patience, since the daily price of oil will always rise and fall. His family office has been in oil and gas since the mid-1980s and says it averages a little over 60% a year in returns, with one project returning more than 50% to investors in the last 18 months, and it stays conventional, drilling vertical shallow wells of up to about 10,000 feet in areas of proven production. Because only about 50% of oil in the ground can be extracted, he halves reserve estimates when judging whether a project can return capital within 18 to 24 months. He notes that the United States produces about 14 million barrels of oil a day and that AI searches use about 10 times the energy of a Google search, which he sees driving long-term energy demand.https://www.youtube.com/embed/FrVa-TaXpZk9382026-02-19 https://familybusinesses.com/fireside-chats/4I81BDixlM4/2026-09-29https://i.ytimg.com/vi/4I81BDixlM4/hqdefault.jpgA non-dilutive equity stake can be worth far more than a larger share that gets diluted.At a Family Office Formula event, Richard C. Wilson walks through mental models and actions common among wealthy business builders, starting with the point that first impressions matter greatly with family offices and other sophisticated investors. He describes a company that scaled from $30 million to $140 million in 18 months with capital from one publicly traded company met at a club summit. On deal structures, he covers preferred returns of 8% to 16% and explains why a small equity stake that cannot be diluted can be worth more than a larger one diluted many times. He retells his own path, from a $1,500 multi-level marketing business in high school to 1,000 blog posts and buying the familyoffices.com domain for $10,000. He also describes reading 131 books by billionaires and studying the top 12 in depth, one per month.https://www.youtube.com/embed/4I81BDixlM452342026-02-12 https://familybusinesses.com/fireside-chats/ERpayOSBze4/2026-09-29https://i.ytimg.com/vi/ERpayOSBze4/hqdefault.jpgThe skills needed to create wealth are often opposed to the skills needed to preserve it.A Whittier Trust executive says the skills needed to create wealth are very different from, and often opposed to, the skills needed to preserve it over generations. Whittier Trust began in 1935 as the single family office for the Whittier family, developers of Beverly Hills and the Beverly Hills Hotel, and still serves the sixth generation of that family while acting as an outsourced family office for others, with about $26 billion under management. The surprise, in the executive's experience, is how simple multi-generational wealth can be: many families preserved and grew wealth mostly through stocks, bonds and real estate. The executive encourages wealth creators, even those who built very valuable companies, to come to the table with humility and learn from advisors who have seen hundreds of families. The firm also makes direct real estate investments, historically including value-add multifamily.https://www.youtube.com/embed/ERpayOSBze43592026-01-17 https://familybusinesses.com/fireside-chats/sH-H5AnnEsw/2026-09-29https://i.ytimg.com/vi/sH-H5AnnEsw/hqdefault.jpgRaise $100,000 first, then a quarter million, then a million, not $50 million on day one.In a long live hot seat webinar, Richard C. Wilson tells capital raisers without much experience to start by raising $100,000, then a quarter million, half a million, $1 million and $1.5 million, rather than trying to raise $50 million or $400 million. He says experienced raisers report needing 250 to 300 prospects to find the 12 to 14 investors who helped them raise $100 million. He describes how a family office might back a founder's fund with $5 million if the founder puts in $500,000 that absorbs losses first. He warns about fake investors who claim $500 million and then ask for a $50,000 upfront due diligence fee. He also notes that one club member raises more than $5 million a month with small minimums, and that a multi-family group grew to $1 billion in assets with $25,000 minimums.https://www.youtube.com/embed/sH-H5AnnEsw102652026-01-17 https://familybusinesses.com/fireside-chats/CSqQ4U7M_Rw/2026-09-29https://i.ytimg.com/vi/CSqQ4U7M_Rw/hqdefault.jpgThe most important strategic asset we acquired was mindset.Pavan Agarwal says the most important strategic asset his family's mortgage company acquired was mindset, moving from thinking like a small local company to believing it could become something much bigger. His father started Sun West Mortgage with less than $100,000, and it grew into a multi-billion dollar national lender. The family's rules were to do it right, never break a trade and never lie, and those relationships carried the company through the financial crisis when it was down to its last $50,000. He describes his father as old school, spending a dollar only when 100% sure it would make 100, which built a stable business but did not scale it. Agarwal ran his first AI program in 1985 and has built Angel AI, described as a fintech AI companion for home ownership.https://www.youtube.com/embed/CSqQ4U7M_Rw14122025-12-30 https://familybusinesses.com/fireside-chats/dItEOB-1jCs/2026-09-29https://i.ytimg.com/vi/dItEOB-1jCs/hqdefault.jpgWhen you partner or exit your family business, make sure you pick the right partner.A private equity investor who grew up in a family business and invests only in family-owned or Hispanic-focused consumer businesses tells owners who want to partner or exit to choose the right partner, because corporate culture, legacy and treatment during the hold period matter as much as capital. In one deal with no debt, because the selling family was averse to debt, his firm tripled revenue and doubled EBITDA in three and a half years and sold for about 2.3 times its money. Jonathan Bergman, president of TAG Associates, an $8 billion multi-family office founded about 36 years ago, says roughly one third of its investment base is in alternatives. Other panelists include a family whose group spans consumer products, hotels, retail and insurance in Korea and Japan, and an adviser to ultra-high net worth Latin American families. The panel also warns that some family business owners fear being overwhelmed by teams of lawyers and business school graduates from large institutions.https://www.youtube.com/embed/dItEOB-1jCs28062025-12-01 https://familybusinesses.com/fireside-chats/JFlg4gy-oCQ/2026-09-29https://i.ytimg.com/vi/JFlg4gy-oCQ/hqdefault.jpgFamilies go to 10 different advisers, get 10 different answers and end up doing nothing.A wealth management panelist says business owners who make their own decisions often consult about 10 different advisers, get 10 different answers and end up doing nothing because the problem feels too complex. Another panelist, a former venture capitalist now focused on senior living, notes that while some presenters talk about 20% to 25% returns, the largest firms such as BlackRock and Apollo are telling their limited partners that 13% to 15% may be very good over the next decade. Richard C. Wilson observes that after hosting 250 events in 12 years, he has heard investors predicting a market drop within 12 to 18 months for three years running, and that patient families now expect to hold new investments for 12 to 15 years rather than four to seven. He also argues that fee structures earn trust when managers charge less or nothing when investors make no money. A panelist describes helping a family business add 60% in revenue in 18 months.https://www.youtube.com/embed/JFlg4gy-oCQ21682025-12-01 https://familybusinesses.com/fireside-chats/CLIccErwCF4/2026-09-29https://i.ytimg.com/vi/CLIccErwCF4/hqdefault.jpgHard, verifiable numbers in a one-liner make investors lean forward more than claims of being big.In a live rating session, investors score audience one-liners and brand names on first impressions, and Richard C. Wilson says the strongest lines use tangible numbers that can be verified, such as a 72-person team, 33 years in one strategy or $400 million in assets, instead of claims like 'best in class.' Panelist Rob Beers, a fourth-generation general partner of two Washington, D.C. and Baltimore real estate companies that are each more than 100 years old, holds office, retail, multifamily and golf course assets. Another panelist's firm is on its fourth fund, a $520 million platform writing $50 million to $150 million checks, and a third panelist teaches family office strategies to about 10 families that piggyback on most of its deals. Wilson notes that raising $10,000 can happen through crowdfunding after a 30-minute review, but raising $100,000 to $1 million takes more due diligence and relationship building. He adds that any one-liner will be weak until it has been rewritten 20 or 30 times.https://www.youtube.com/embed/CLIccErwCF421522025-12-01 https://familybusinesses.com/fireside-chats/lZH4_7w7oz8/2026-09-29https://i.ytimg.com/vi/lZH4_7w7oz8/hqdefault.jpgDon't just measure return on investment, measure your return on engagement.Panelists at the Hawaii Family Office Retreat describe buying and growing companies from retiring founders, often keeping the founder in place, letting them take some equity off the table and installing systems to scale. One investor targets companies with $20 million to $100 million in enterprise value and describes a founder doing about $10 million in revenue who is the bottleneck of the company. Another compares returns on invested capital, noting that their own $40 million manufacturing business earns 200%, so an exit would have to beat that. A real estate operator went from 11 rental properties in 2015 to more than $2 billion of acquisitions. On the next generation, one panelist cites survival rates of about 35% to 40% into the second generation and about 12% into the third, and urges families to measure return on engagement, not just return on investment.https://www.youtube.com/embed/lZH4_7w7oz818002025-11-19 https://familybusinesses.com/fireside-chats/5eBNkyCGClc/2026-09-29https://i.ytimg.com/vi/5eBNkyCGClc/hqdefault.jpgSet up a generation-skipping trust and put assets in it while their value is low.A panelist says the best way to provide for the next generation and the one after it is a generation-skipping trust funded with assets at a low current value so they can appreciate inside it, calling the 40% gift tax on money already made 'real theft.' A mineral investor says exclusive deals are seldom brought to his firm; instead it pulls lease records at courthouses to identify large mineral owners, and one large deal took three years of building a relationship with a ranch owner. An estate planner says the two questions clients raise most are how to keep the family functional and the kids not spoiled, and how to transfer wealth without spoiling them. Another panelist points to high interest rates on small-balance commercial real estate loans from $600,000 to $6 million. A litigation finance investor describes third-party litigation funding as a novel industry that has been around since 1910.https://www.youtube.com/embed/5eBNkyCGClc4352025-11-12 https://familybusinesses.com/fireside-chats/JJry4vQK8es/2026-09-29https://i.ytimg.com/vi/JJry4vQK8es/hqdefault.jpgOne family office portfolio is 100% alternatives, with zero public market exposure by design.A panelist who was previously chief investment officer for a multi-generation legacy family in Pittsburgh describes a portfolio that is 100% alternatives with zero public market exposure by design, an extreme version of the broader shift of family offices toward alternatives. The moderator has led his own Dubai-based single family office for more than two decades, investing directly and through co-investments in commercial real estate, renewable energy and waste management. Another panelist builds a platform that gives high net worth families investment vehicles, a more vertically integrated way of doing business and a structure for proper succession and transfer from one generation to the next, with a heavy focus on real estate because that is how his families built their passive portfolios. Jonathan Tuttle has spent 15 years in mobile home parks through his fund, Midwest Park Capital. The panel also notes that in the West, a single family office can bring tax advantages compared with other structures.https://www.youtube.com/embed/JJry4vQK8es6202025-09-25 https://familybusinesses.com/fireside-chats/Mb2o38AuGKU/2026-09-29https://i.ytimg.com/vi/Mb2o38AuGKU/hqdefault.jpgMost real estate transactions get into trouble because they run out of time or money.A brokerage executive whose company has about 200,000 active agents says most real estate transactions get into trouble for two reasons: they run out of time or they run out of money. A private lender explains that sponsors doing $100 million deals can often get only about 60% loan to value from institutions, so a lender stretching senior debt to 70% or 75%, with a preferred equity slice, can cut the sponsor's equity need from about $40 million to about $10 million, at rates of 9% to 11%. A former Mayo Clinic and Cleveland Clinic surgeon describes building regenerative, healthcare-integrated communities near major universities and hospitals, raising $1 million to $10 million checks from high net worth individuals, family offices and physician groups. Another investor says preferred equity made sense for about 10 years, but that with interest rates near their peak and values down from 2021, it is now a good time to move into equity. A panelist also points out that about 10,000 people turn 65 every day, supporting senior housing.https://www.youtube.com/embed/Mb2o38AuGKU14332025-09-20 https://familybusinesses.com/fireside-chats/dguHtbz_fOk/2026-09-29https://i.ytimg.com/vi/dguHtbz_fOk/hqdefault.jpgPhilanthropy lets parents watch which children will rise to the occasion.A multi-family office principal on the panel says family philanthropy brings the whole family around the table, lets parents hear which children want to be involved, and shows which children will rise to the occasion before they inherit the for-profit side of the family office. Other panelists discuss using AI and CRM tools, with one noting that real estate runs 5 to 10 years behind other industries on technology. A real estate operator says investors who backed his company in 2002 and 2003 have since handed their family office to their children, and on his most recent deal with them he returned 10 times their money in 18 months. Another panelist's family foundation has run mentoring programs since about 2005, including helping a young man from South Africa become the first Black player on the South African polo team. The closing advice is not financial: don't forget your health, your kids and your family.https://www.youtube.com/embed/dguHtbz_fOk10952025-08-19 https://familybusinesses.com/fireside-chats/b-E9SJepcz4/2026-09-29https://i.ytimg.com/vi/b-E9SJepcz4/hqdefault.jpgI made it a priority 20 years ago to start having my kids travel with me.Two family office principals explain how they keep several generations aligned when each generation communicates differently. Uli's family started biannual family governance retreats about 25 years ago, lasting several days, often at places like national park lodges, with agendas built from family members' input and facilitation by staff or outside consultants. The second panelist has 5 married children and 18 grandchildren, holds family meetings each spring and fall, and now lets his oldest son set the agenda as he hands off to his children. After an exit, his family interviewed several multi-family offices, decided the fees were too high, and has run its own family office with his two sons for 7 years. Both say the non-financial side, from shared experiences to financial literacy and health and wellness, holds the family together alongside the money.https://www.youtube.com/embed/b-E9SJepcz42652025-08-18 https://familybusinesses.com/fireside-chats/0dSvZ_vRptY/2026-09-29https://i.ytimg.com/vi/0dSvZ_vRptY/hqdefault.jpgMom and dad doing estate planning by themselves is going to be a disaster.A multi-family office principal who serves families under $250 million says traditional estate planning, where parents in their 80s go to an attorney alone and divide everything by four, sets the family up for disaster, so his firm brings the children into succession planning and spends a lot of time on governance and family dynamics. Other panelists include a descendant of Wilhelm Maybach whose family foundation focuses on archives, legacy and mentoring and whose family office is about 50% real estate, and a second-generation principal who started a family office after a 2014 exit with his father. One founder sold his network of 150 stores in 2017 and started a family office in Utah with his two older sons. Another says his family sold a fintech company at a 49.5 times multiple and has kept a 50/50 split between tech and real estate for 20 years. The panel stresses that a family enterprise should exist even when all the money is gone.https://www.youtube.com/embed/0dSvZ_vRptY6362025-08-14 https://familybusinesses.com/fireside-chats/Ac6I93giXF8/2026-09-29https://i.ytimg.com/vi/Ac6I93giXF8/hqdefault.jpgThe second generation was ready to retire, but the third still had gas in the tank.An M&A adviser describes a nine-figure sale of a family company founded by a grandfather, where the second generation was ready to retire but the third generation wanted to keep the business going and the two could not agree. The adviser notes that the number of M&A deals in January 2025 fell 30% from January 2024, yet says the market is poised for strong transactions. About 60% of small businesses are owned by baby boomers, which the adviser says primes the market for retirement sales. The adviser adds that private equity firms are holding companies for a record 8.5 years on average while sitting on large amounts of uncommitted capital.https://www.youtube.com/embed/Ac6I93giXF82012025-08-12 https://familybusinesses.com/fireside-chats/PsX6Kh4E9Ss/2026-09-29https://i.ytimg.com/vi/PsX6Kh4E9Ss/hqdefault.jpgStarting a business just to make money and exit is a terrible business plan.Patrick O'Meara says a business built only to make money and exit is a terrible business plan, and he looks for operators with 10 to 20 years of experience in their industry. He completed about $11 billion in transactions during his corporate career, and his family office has made about 40 commercial real estate investments and about 20 private equity and venture investments. His current focus is senior housing built with the Catholic Church on 90-year flat-rent ground leases, with 10% of net operating income donated to the parish and 2,000 people on a waiting list in Phoenix. He admits that when he first created wealth he chased deals with no rhyme or reason, and now filters by people, process and product. He named his real estate company Taylor Street after his 18-year-old daughter, who attended the event.https://www.youtube.com/embed/PsX6Kh4E9Ss10482025-08-11 https://familybusinesses.com/fireside-chats/1je_oa22YhY/2026-09-29https://i.ytimg.com/vi/1je_oa22YhY/hqdefault.jpgAnyone in business for the next 30 years had better learn accounting.Kevin McGovern, chairman and CEO of the single family office McGovern Capital, says anyone planning to be in business for 30 years should learn accounting, just as anyone living in Spain for 30 years should learn Spanish. He has co-founded more than 25 companies, six of which became world category leaders, and has been a principal in more than 15 global joint ventures across more than 80 countries. He calls his son, his team and his entrepreneurial family his hidden tool, and says family is the first priority of his life. McGovern advises founders that raising $1 million at a $20 million valuation does not make them worth $20 million, and to double down on what works: if something is working, do 10 times more of it. To reach sovereign wealth funds and large family offices, he says to learn the names of the assistant, the spouse, the children and even the dog.https://www.youtube.com/embed/1je_oa22YhY17632025-07-30 https://familybusinesses.com/fireside-chats/rr4c3W98J30/2026-09-29https://i.ytimg.com/vi/rr4c3W98J30/hqdefault.jpgMoving a family from ad hoc decisions to formal governance is extremely hard.A Los Angeles multi-family office founder says the part of family office work he most wishes he had heard about years ago is the nitty-gritty of family governance, because moving a family from ad hoc decisions to formal structure is extremely hard. He points to the 2017 Lender Management case against the IRS as the landmark case for modern family office structuring. He urges sponsors to research a family before pitching, noting that AI research can replace 100 Google searches, and that his first 10 minutes with one investor were entirely about conservation. On raising children, he argues that the youngest generation should learn to create value before learning to spend money. He attracts investors with technical content, such as an article on section 704(c) built-in gains.https://www.youtube.com/embed/rr4c3W98J3014872025-07-29 https://familybusinesses.com/fireside-chats/ZN_SMZwcXEs/2026-09-29https://i.ytimg.com/vi/ZN_SMZwcXEs/hqdefault.jpgCompounding started when we decided we were in the wealth business with one client: our family.Yahya Mahmud, a real estate investor with more than 25 years of experience, says his returns started compounding once he and his wife decided they were in the wealth business with a single client: their family. They began investing in real estate straight out of college as a middle class couple with regular jobs, started lending in 2015 when someone asked to borrow money, scaled the lending business in 2017 and sold it in 2024. He says the business itself snowballed when they started hiring for ownership, giving leaders frameworks, support and the trust to make decisions on their own. In underwriting, he evaluates the person before the deal, because before anyone trusts you with their money they must trust you with the relationship. He also contrasts eighth-generation family offices, which spread risk across many advisers, with first-generation wealth builders, for whom the money is personal.https://www.youtube.com/embed/ZN_SMZwcXEs13512025-06-24 https://familybusinesses.com/fireside-chats/4gUI3DH0B3E/2026-09-29https://i.ytimg.com/vi/4gUI3DH0B3E/hqdefault.jpgMany of my families are moving from G1 to G2 and looking to exit their businesses.A multi-family office principal says many of the families the firm serves are in the transition from the first to the second generation and are looking to exit their businesses, so their portfolios need more high-grade fixed income, and the firm is working to strengthen private credit for them. The easiest ways to guarantee failure are weak security in transactions, poorly vetted partners and skipped research such as UCC searches, and even the best deal with a bad partner will not end well. The principal's biggest piece of advice is not to be afraid to say no to people who are less serious or less knowledgeable about their business. The principal sees the wealth transfer from one generation to the next as where many of the current opportunities lie in the family office space.https://www.youtube.com/embed/4gUI3DH0B3E3292025-06-07 https://familybusinesses.com/fireside-chats/CW0o4P3G3-g/2026-09-29https://i.ytimg.com/vi/CW0o4P3G3-g/hqdefault.jpgOwning a strategic choke point, such as a leading industry expo, can create lasting deal flow.In this keynote, Richard C. Wilson explains how billionaires build wealth by owning strategic choke points, positions with barriers to entry that others cannot easily copy. He cites the club's early blog, which reached 3,000 to 7,000 hits a day around 2008, and about a million LinkedIn members by 2012 to 2014, and suggests partnering with a leading expo in exchange for equity. For acquisitions, he recommends building a focused database of about 100 companies in a niche with outsourced help at $6 to $12 an hour, noting that bolt-ons usually need at least $1 million to $3 million of EBITDA. He says the club has used gross revenue royalties of 1% to 3% on 16 or 17 deals and prefers exit equity warrants that cannot be diluted. He also stresses securing a respected anchor investor first and notes that many of the best deals close without most investors ever hearing about them.https://www.youtube.com/embed/CW0o4P3G3-g27292025-05-19 https://familybusinesses.com/fireside-chats/ChmN2MlYvxw/2026-09-29https://i.ytimg.com/vi/ChmN2MlYvxw/hqdefault.jpgA lot of fourth-generation family companies struggle because the families remember old grudges.An allocator whose family group runs 13 companies in Salinas, California, the source of about 80% of the salad Americans eat, says the family-owned agriculture businesses it looks at are typically fourth-generation companies where relatives remember old grudges and carry a lot of ego. Other panelists include the healthcare lead at a single family office with about $2.9 billion in invested assets and a structured finance executive whose team financed about $3 billion of commercial real estate. A real estate fund manager says he did deals only in the Bronx for his first 10 to 15 years before expanding, and never imagined running a multi-billion dollar fund. Allocators tell managers that a typical ticket is $10 million and they do not want to be more than 10% of a fund, so a fund must be at least $100 million, and pitch decks should run about 10 to 15 slides. The agriculture allocator also describes buying about $5 million of real estate on seller financing at about 23% loan to value.https://www.youtube.com/embed/ChmN2MlYvxw18692024-11-05 https://familybusinesses.com/fireside-chats/uMUs4h_6BMQ/2026-09-29https://i.ytimg.com/vi/uMUs4h_6BMQ/hqdefault.jpgIt took 20 years before we were able to turn it around and sell.Michael Houlihan and Bonnie Harvey co-founded Barefoot Wine without being wine drinkers, after a 1985 effort to collect $300,000 owed to a grape grower client left them taking over the debt, bottling services and bulk wine. They started in the laundry room of a rented farmhouse and expected a turnaround in about 3 years, but it took 20 years to turn the business around and sell it. For owners thinking about an exit, they sit the owner down with a broker who sold a business like theirs that year, and they caution that handing a company to children works only if the children want to do what the parent wants. They now produce business audio theater that dramatizes a founder's real decisions, which they present as a way for family offices to capture the founder's story and values. They also see it as a way for new employees to learn a company's history and principles.https://www.youtube.com/embed/uMUs4h_6BMQ15662024-10-24 https://familybusinesses.com/fireside-chats/jnj9gAKXY8k/2026-09-29https://i.ytimg.com/vi/jnj9gAKXY8k/hqdefault.jpgHe was a third-generation pro athlete and was still rejected by over 850 colleges.A former professional football player named David, a third-generation pro athlete and sixth-generation college graduate, says that despite his family legacy he was rejected by more than 850 Division I colleges and over 10,000 scouts. His grandfather on his mother's side played for the Boston Bruins, and his father played against the 1985 Bears. He says his biggest mistakes came when he lacked a vision of his bigger future and was sitting in his comfort zone, so his main lesson is to always have that vision. After his playing career, a mentor brought him back to reading and learning, and he now tells people to keep a learn list, study constantly and spend time with people who challenge them. That advice led him to learn a second language and take up the piano.https://www.youtube.com/embed/jnj9gAKXY8k21542024-09-26 https://familybusinesses.com/fireside-chats/i9ALORjfp3Q/2026-09-29https://i.ytimg.com/vi/i9ALORjfp3Q/hqdefault.jpgPouring $5 or $10 million into children kills their motivation to do something.Richard C. Wilson says families kill their children's motivation when they pour $5 million or $10 million into them, whether early in life or through an inheritance at 35 or 40. Instead, when children bring a business idea to the family, senior members can approve it and provide a loan, help buy the business or sign a letter of credit, helping them create value through struggle. He suggests spending $200 to $5,000 to buy a young person a small business where they set their own prices, noting that he started five businesses before graduating high school while watching his father run a business. He observes that the families the club serves are first or second generation, while by the third, fourth or fifth generation families usually play a purely defensive game. He adds that people who receive sudden windfalls, from young heirs to athletes to business sellers, often lose the money just as quickly.https://www.youtube.com/embed/i9ALORjfp3Q16682024-08-17 https://familybusinesses.com/fireside-chats/x5tkqmIhvIY/2026-09-29https://i.ytimg.com/vi/x5tkqmIhvIY/hqdefault.jpgMany families lose critical people when they don't appreciate those who take care of their investments.A former Chase workout banker who went on to buy companies out of bankruptcy with capital from billionaire families says he has seen many families lose critical people because they stopped respecting and appreciating the people who do business for them and take care of their investments. After seven years at Chase, where his nickname was the Pitbull, he ran a financial advisory firm focused on bankruptcy and distress, then cold called billionaire families to back his idea of buying bankrupt companies. He has since bought 11 companies in 11 industries, including two sole-source military parts businesses, and has chaired a bank's credit committee for 13 years. On one acquisition, cash flow in the first seven months equaled 150% of the equity check. He now works for a billionaire family, including with the founder's children, and says the families he has seen succeed share one trait: they never give up.https://www.youtube.com/embed/x5tkqmIhvIY26722024-07-31 https://familybusinesses.com/fireside-chats/pr0rHXqDiv4/2026-09-29https://i.ytimg.com/vi/pr0rHXqDiv4/hqdefault.jpgLet experts manage 90% of your money and keep 10% to play with.Larry Namer co-founded E! Entertainment Television with $2 million at a time when starting a TV network typically took about $100 million and a large corporation. The network launched with 11 employees and 31 interns, and he says the company is now valued around $5.2 billion. After his exit, he had people who know money better than he does manage 90% of his wealth at a consistent 7% to 8% a year, and he keeps 10% to invest himself, including one bet that lost 60%. He grew up in Brooklyn in an immigrant family, raises his children with rules about staying humble, and warns founders against building businesses around what AI is today. He also produced the number one TV show in Russia for 10 years, five days a week.https://www.youtube.com/embed/pr0rHXqDiv413082024-06-19 https://familybusinesses.com/fireside-chats/-zpL9zvNzSA/2026-09-29https://i.ytimg.com/vi/-zpL9zvNzSA/hqdefault.jpgThe chances of a family business lasting a hundred years are one in a thousand.Mitzi Perdue says a family business left to chance will probably not last, because the chances of reaching 100 years are one in a thousand. She comes from two long-lived family enterprises: the Henderson Estate Company, begun in 1840 and the forerunner of the Sheraton hotels her father and uncle co-founded, and the Perdue family business, operating since 1920. Her practices include a family newsletter that about 70 relatives receive, separate newsletters for children aged about 4 to 13 that tell family stories, annual Henderson reunions held since 1890, and 'Hendinars,' 20-minute talks every two months by family members with expertise. She says establishing family values costs nothing and matters more than the size of any inheritance. Her closing message is that a strong family culture has to be built on purpose.https://www.youtube.com/embed/-zpL9zvNzSA14412024-06-05 https://familybusinesses.com/fireside-chats/RszcHPYhwpo/2026-09-29https://i.ytimg.com/vi/RszcHPYhwpo/hqdefault.jpgI didn't wait till I was done to start spending time with my children.Todd Heiner co-founded Express Locations, which grew to 150 T-Mobile stores in 10 states with 1,400 employees and about $600 million in revenue before it was sold in 2017. He credits his first decision, recruiting the two best partners he could find and letting them acquire equity, and a refusal to take on debt. Growth accelerated after T-Mobile hired a new CEO in 2012, and two minority investors who came in during 2009 earned 28 times their money at the sale. He now runs the Ridgeline Capital Group single family office with his family, including his two older sons in their late 30s, and the family has a mission, vision and values and holds formal family meetings once or twice a year. He took his five children on business trips and did not wait until he was done working to spend time with them and his 17 grandchildren.https://www.youtube.com/embed/RszcHPYhwpo14252024-06-02 https://familybusinesses.com/fireside-chats/hWtT4GnGcbU/2026-09-29https://i.ytimg.com/vi/hWtT4GnGcbU/hqdefault.jpgThere is always somebody you can inspire, because somebody younger than you is watching.Former NBA player C.J. Watson, who began investing in private equity companies and writing children's books in 2019 after 10 NBA seasons and one year overseas, says building generational wealth and inspiring others are his priorities, because there is always somebody younger watching. The best financial advice he received was to save his money, since athletes earn most of their income in a short period and need it to last into their 70s and 80s to create generational wealth. Watson wrote down 10 goals every year during his career, and he and his wife now have their daughters write goals for the school year and for sports. He keeps in touch with contacts once or twice a quarter and says mentors are the most important resource in any venture.https://www.youtube.com/embed/hWtT4GnGcbU8552024-05-21 https://familybusinesses.com/fireside-chats/YOIinI-Tt2c/2026-09-29https://i.ytimg.com/vi/YOIinI-Tt2c/hqdefault.jpgMy biggest mistakes were failures to invest, including the seed rounds at Google and Facebook.Tim Draper says his biggest mistakes as a venture capitalist were failures to invest, including the seed rounds of Google, Yahoo, Facebook and LinkedIn. He helped fund Tesla, SpaceX, Box, Carta and more than 15 other unicorns at the seed stage and has invested in more than 50 crypto companies. His Draper University has trained 3,500 students from 102 countries, who have started about 900 companies, five of them unicorns. He learned from Hotmail, which spread to 11 million users in 18 months, that delighting customers can turn them into a sales force. For parents, he recommends a small allowance, having children earn money, and having them invest it in the stock market early so they learn to read measures like price to earnings ratios and cash flow.https://www.youtube.com/embed/YOIinI-Tt2c14412024-03-19 https://familybusinesses.com/fireside-chats/LlWp1J_3Hbo/2026-09-29https://i.ytimg.com/vi/LlWp1J_3Hbo/hqdefault.jpgEven full-time capital raisers usually approach 200 to 250 investors to find 14 to 20 yeses.Closing a Private Investor Mastermind in Texas, Richard C. Wilson points families to outsourced CFO, accounting and dashboard support through a partner, noting that some clients have 150 LLCs. He says even professional capital raisers with 20-person teams and the best data usually approach 200 to 250 investors to find the 14 to 20 who invest. He warns that he has seen people blow through $40 million after putting $25 million into one investment, and that trusting a relative is not a substitute for understanding a deal. He shares the example of a member who raised an $8 million check and a $40 million check using the club's databases, and notes that the club landed 27 billionaire interviews from 9,000 pitches. He adds that plans assuming everything goes 100% right are a sign of amateur hour.https://www.youtube.com/embed/LlWp1J_3Hbo19622024-02-21 https://familybusinesses.com/fireside-chats/dsV1YYkhWfw/2026-09-29https://i.ytimg.com/vi/dsV1YYkhWfw/hqdefault.jpgMassive output, from teenage flyers to 500 blog posts, built Wilson's family office business.Opening day one of the Super Summit, Richard C. Wilson describes a brute force strategy of massive output that he has used since high school, from stuffing flyers in mailboxes at 17 to building websites for $16 an hour in 1996 and 1997. When capital raising firms turned him away for lacking a $100 million track record, he started blogging in 2007 and wrote two posts for each of 500 family office keywords, reaching 5,000 to 7,000 hits a day. He says luck is a four-letter word for a reason and cautions against telling children that the family's success is luck. He also shares deal structures that remove friction for co-investors, such as letting a partner take all of their capital back before he receives anything. Other examples include a domain purchase that took 150 emails over 12 years and a mentor who secures a blue chip anchor investor before raising the rest.https://www.youtube.com/embed/dsV1YYkhWfw10082024-02-02 https://familybusinesses.com/fireside-chats/j7-W3szoGrE/2026-09-29https://i.ytimg.com/vi/j7-W3szoGrE/hqdefault.jpgGlobal asset protection used to be hide-and-seek, and now it's show-and-tell.Joel Nagel, an international asset protection attorney who has worked in 43 countries over 34 years, says global asset protection used to be treated as hide-and-seek and is now show-and-tell: when someone looks, you show the structure openly. He explains that a trust holding assets passively, or holding active businesses through a corporate structure, is how wealth is perpetuated, because it avoids generational gift and estate tax. He urges families to slow down on planning to protect and pass on wealth, noting that clients often call on December 29th hoping to finish by the 31st. Nagel founded ECI real estate development in 1996, which owns 4,000 acres and $130 million of real estate assets in Central America, and helped set up an international bank in Belize in 2003. On his own children, he says he does not want them to become trust fund babies and moderates the wealth they can access.https://www.youtube.com/embed/j7-W3szoGrE19812024-01-11 https://familybusinesses.com/fireside-chats/AnibOi7uZ5k/2026-09-29https://i.ytimg.com/vi/AnibOi7uZ5k/hqdefault.jpgRemoving stress and toxicity from a business can make everything, including growth, go faster.Richard C. Wilson shares seven ways to have the most fun year of your life in business and health, arguing that removing stress and toxicity from a business can make everything go faster. He describes running lemonade stands with his children, who aim to earn $1,000 in a weekend, and outdoor adventures such as a climbing route with 130 ladders and bridges. He says having fun in business is the non-obvious part of the message and urges business owners to cut as much as 80% of the work outside their strengths. He points to persistence, including 161,000 emails sent since starting the business and 9,000 emails to land 27 billionaire interviews. He recalls starting in a basement apartment in Harvard Square without $1,000 for rent and says it can take courage to build your own business instead of someone else's.https://www.youtube.com/embed/AnibOi7uZ5k10682024-01-09 https://familybusinesses.com/fireside-chats/DjFpdY31aZ0/2026-09-29https://i.ytimg.com/vi/DjFpdY31aZ0/hqdefault.jpgMy generation doesn't necessarily want to invest the way our parents invested.A 39-year-old panelist says the biggest wealth transfer in history is happening now and that his generation does not necessarily want to invest the way their parents did, so his platform aims to bring proven winners to the table for them. Another panelist says the wealthiest families he knows focus on one or two niches, and his firm puts about 95% of its energy into multi-location medical and dental practices, holding minority stakes in 24 practices with about $50 million a year in revenue. A real estate investor says his firm is in its 18th year and has never lost a dime or made a capital call. A former Google executive turned angel investor looks for founders who have had failures or shown growth, and notes that women founders often need about 50 introductions to get one meeting. Richard C. Wilson adds that paying a broker extra can buy a 90-minute first look at a deal, and that joining three to five niche communities improves deal flow.https://www.youtube.com/embed/DjFpdY31aZ08582023-12-22 https://familybusinesses.com/fireside-chats/Wo8e1ScqJ6c/2026-09-29https://i.ytimg.com/vi/Wo8e1ScqJ6c/hqdefault.jpgLegal documents alone can't solve the wealth transfer problem, because there's an emotional part.David Sebastian says gift and estate documents alone cannot solve the wealth transfer problem, which he sizes at more than $70 trillion moving to the next generation within 25 years, because there is an emotional part to it. He has worked with clients in Sun Valley, Idaho worth about $50 million and clients in San Francisco making about $50 million a year. When a family has no process for growing wealth after an exit, he says the second or third generation can feel stuck, not knowing what to do with the money, and may simply spend it. He notes that the average family has about 27 advisers, and that many families end up needing a fractional CFO who bridges the business and personal sides. He also quotes the estate tax exemption at $25 million for lifetime gifting, with 40% tax above it.https://www.youtube.com/embed/Wo8e1ScqJ6c5412023-11-15 https://familybusinesses.com/fireside-chats/k8zyq2d2giY/2026-09-29https://i.ytimg.com/vi/k8zyq2d2giY/hqdefault.jpgAt 22, like his NFL rookie son, a former pro wasn't thinking about investing.A former professional athlete whose son is in his first NFL season says the hardest part is guiding a 22-year-old who has just started making money, since at that age he was not thinking about investing either. Another panelist, a top high school pick who turned down a signing bonus to go to college, says his father, an educator, told him that after taxes and a car the bonus was worth about the same as his education, and he went on to play at the University of Miami and in the 1992 Olympics. Panelists say many athletes do not know what they do not know, and that surrounding themselves with smarter people opened doors to real estate, private equity and relationships with prominent families. Another panelist credits family and friends who always pushed for thinking about the next step and to stress academics as well as athletics. Richard C. Wilson draws a parallel between athletes' children entering sports and surgeons' children becoming surgeons, both needing to preserve wealth earned in intense careers.https://www.youtube.com/embed/k8zyq2d2giY10272023-10-26 https://familybusinesses.com/fireside-chats/dvlxOlsY-3Y/2026-09-29https://i.ytimg.com/vi/dvlxOlsY-3Y/hqdefault.jpgProfitable businesses with 50 to 100 employees are winding down because there is no succession plan.Renan Cortez says many profitable service businesses with 50 to 100 employees are struggling to sell and winding down because their retiring owners have no succession plan. Many of these owners are baby boomers who started or inherited the business, and their children were often told to do better than the trades. After 12 years in the military and 15 years in medical device sales, Cortez bought his first company at 46 or 47. That first acquisition was an $8.6 million business doing about $2 million in EBITDA, bought with no money down and improved to about $2.5 million in EBITDA year to date by adding management structure and efficiencies. His firm, Syndicate Venture Group, sources off-market deals directly from owners and plans to grow a portfolio to $100 million in aggregate EBITDA.https://www.youtube.com/embed/dvlxOlsY-3Y15222023-10-02 https://familybusinesses.com/fireside-chats/qO8HvDX2Rbo/2026-09-29https://i.ytimg.com/vi/qO8HvDX2Rbo/hqdefault.jpgAbout 70% of families don't make it to the next generation, mostly because of family quarrels.Mitzi Perdue says roughly 70% of family businesses do not make it to the next generation, and the biggest reason is family quarrels, especially once they go public in the newspapers or before adversarial lawyers. Drawing on the research of Dennis Jaffe, she describes three practices of families that last: keeping quarrels private, using philanthropy as family glue by the second or third generation, and teaching children from the youngest age that they are stewards who must hand the business to the next generation in better shape. The Henderson family business began in 1840, and in 1890 John Cleves Symmes Henderson and his children endowed a family dinner that has grown into an annual family weekend with a service-to-the-family award. The Perdue family uses children's newsletters to teach values such as frugality, and a Giving Club lets children aged about 8 to 14 decide where foundation money goes. She adds that family members personally sewed masks for Perdue's 22,000 employees.https://www.youtube.com/embed/qO8HvDX2Rbo9192023-06-27 https://familybusinesses.com/fireside-chats/uAbfrdC7UYY/2026-09-29https://i.ytimg.com/vi/uAbfrdC7UYY/hqdefault.jpgBeing a business owner is your chance to leave a legacy for your employees and community.Jeff Hoffman, part of the Priceline founding team, tells a Family Office Super Summit audience that being a business owner is a chance to leave a legacy for employees and the community. He grew up in the Arizona desert with a single mother and four children, never going to a restaurant or on vacation, and set a childhood goal of having dinner with families in 50 countries before judging anyone; he has since done it in 100. When he sold one company to a Fortune 500 firm, he learned it had 0% voluntary turnover, because no one who worked for him had ever quit. He describes helping an employee get what he wanted from his career, and that employee is now a vice president at a Fortune 500 company with three children in college. Hoffman now runs a youth charity where volunteers do the work, he pays the overhead and 100% of funds go to children.https://www.youtube.com/embed/uAbfrdC7UYY39332023-06-22 https://familybusinesses.com/fireside-chats/G71pT4GGPgY/2026-09-29https://i.ytimg.com/vi/G71pT4GGPgY/hqdefault.jpgWilson hangs his family values above the kitchen table and urges every family to do likewise.Opening the 2023 Single Family Office Summit, described as roughly the club's 197th live event, Richard C. Wilson explains how he started the Family Office Club in 2007 and now runs it with a 25-person team. He recounts childhood business attempts, driving his father to nonprofit donor meetings, being threatened with losing computer lab rights for starting a business at school, and taking 23 credits a term in college. After capital raising firms said they needed someone who had raised $100 million, he wrote two blog posts for each of 500 keywords, spoke more than 200 times in 15 countries and wrote 13 books in 16 years. He turned his Boy Scout values into family values that hang above the kitchen table, and his children are rewarded or punished based on them. He adds that he holds equity in about 25 medical practices and that the room has produced more than 100 transactions.https://www.youtube.com/embed/G71pT4GGPgY10112023-06-01 https://familybusinesses.com/fireside-chats/mCJOQso40JQ/2026-09-29https://i.ytimg.com/vi/mCJOQso40JQ/hqdefault.jpgMost families, even ultra wealthy families, don't have written family values.Richard C. Wilson, founder of the Family Office Club, tells The Investor's Podcast that most families, even ultra wealthy ones, do not have written family values, and recommends keeping them above the kitchen table so the family acts in line with them and hires and fires investment managers on that basis. Wilson has helped set up more than 200 family offices and started the business about 16 years before the recording. He explains that founders often know one industry deeply for 30 years but are relative beginners at choosing a wealth adviser or diversifying into direct investments, which leads to expensive mistakes. He also describes royalty financing as a way to raise capital while being diluted by only 1% or 2% each round instead of 10% to 30%, noting he has met only one family, from Norway, that had done a royalty deal. On taxes, he warns that paying 30% instead of 10% or 20% on a transaction can cost years of extra work.https://www.youtube.com/embed/mCJOQso40JQ34252023-03-02 https://familybusinesses.com/fireside-chats/-dFaQbcCqyE/2026-09-29https://i.ytimg.com/vi/-dFaQbcCqyE/hqdefault.jpgThomas Handler recommends keeping about 10% of net worth in an asset protection trust.Attorney Thomas Handler compares advanced planning to Maslow's hierarchy of needs, with a foundational level at the base, and says doing it at a high level may cost about 15% more for 40% more impact. He estimates that about 130 proprietary planning strategies exist globally at any time, that evaluating one can cost $30,000 to $70,000 in legal fees, and that most professional firms are closed architecture offering only their own strategies. He describes a structure he devised in which a virtual family office runs one or more family holding companies that are wholly owned by trusts, and warns that domestic asset protection trusts face a 10-year bankruptcy lookback. Out of about 340 single family offices his team has worked with, six are gone, so he recommends keeping about 10% of net worth in an asset protection trust. He also explains that prenuptial agreements depend on full financial disclosure and introduces the stealth prenup.https://www.youtube.com/embed/-dFaQbcCqyE9872023-02-21 https://familybusinesses.com/fireside-chats/c-hO31PmZI0/2026-09-29https://i.ytimg.com/vi/c-hO31PmZI0/hqdefault.jpgAlmost no $100 million families have their values on the wall, though most companies do.Richard C. Wilson outlines free resources for private investors and family offices, including a family office dashboard with 67 fields that shows what homework a family still has to do. He says about 50 questions should be answered before anyone designs a family's financial game board, and that skipping them can cost months of time or hundreds of thousands in fees. In a show of hands, about 90% of the room had company values but only about 8% had formal family values, and he says he has almost never met a $100 million family with its values on the wall. He describes having his children earn the money for things they want and explains how wealthy families split wealth into buckets such as conservative, cash flowing real estate. For new investment areas, he recommends studying a niche deeply, reviewing around 100 deals and starting small.https://www.youtube.com/embed/c-hO31PmZI08842023-02-14 https://familybusinesses.com/fireside-chats/RfKTDC7STvo/2026-09-29https://i.ytimg.com/vi/RfKTDC7STvo/hqdefault.jpgMost Family Office Club clients are first-generation founders or heirs formalizing a family office.Richard C. Wilson recounts how he started the investor club in 2007 with a blog, reached the front page of the Boston Globe at 25 and grew from small events at the Harvard Club to a 1,100-person summit in New York City. He says that in 2022 his close investors put $55 million to work in transactions within the club, with a goal of about $100 million a year and larger deals pending. Almost all clients are first-generation wealth, or a son or daughter formalizing the family office because the wealth needs to pass on, while third and fourth generation families rarely engage. The club has closed 22 deals with groups that have billion-dollar balance sheets, and also works with smaller investors, including a $15 million net worth member who has done six deals.https://www.youtube.com/embed/RfKTDC7STvo4422023-01-20 https://familybusinesses.com/fireside-chats/-7u3ZR4o87A/2026-09-29https://i.ytimg.com/vi/-7u3ZR4o87A/hqdefault.jpgIt is 10 times more powerful to be well structured before a liquidity event.Structuring a family's affairs before an exit, lawsuit or other crisis is described as 10 times more powerful than fixing things afterward. Richard C. Wilson walks through anonymized clients, including a second-generation family worth about $130 million whose son is starting to take over but which has no formal structure or direct investment buy box after 20+ years of ad hoc decisions, and a family whose wealth is tied up in one overseas business and some real estate. He also describes a father and son in the Northeast with 1,000 employees, a doctor-and-attorney family that has closed several transactions with the club, and a billionaire family with 19 closed deals. Clients range from families worth $1 million to $3 million preparing for a first exit to billionaire families with publicly traded entities. The work includes filling out the family office dashboard, defining direct investment strategies, and planning for issues such as prenups, divorce, drug rehab and offshore trusts.https://www.youtube.com/embed/-7u3ZR4o87A4402022-12-20 https://familybusinesses.com/fireside-chats/VODb-LDrO9U/2026-09-29https://i.ytimg.com/vi/VODb-LDrO9U/hqdefault.jpgYou only need to become ultra wealthy once if you have proper defensive strategies.A functional family office depends on a team of service providers more than a large payroll: a virtual family office may need only a part-time CIO or CFO, while a full single family office typically hires 4 to 6 full-time professionals. The core providers are trust and estate planning, an insurance agent who adds strategic value, a proactive tax planner rather than a CPA who only reports taxes owed, a strategic deal attorney, and a wealth advisor used to ultra-wealthy clients. One client avoided an uncovered claim after a carbon monoxide leak at a newly bought motel because they had requested an air pollution rider on the policy. Richard C. Wilson warns that reporting software vendors often price by net worth, and that many families overpay retail wealth management fees. He also notes that the people managing public market exposure are rarely experts in real estate or direct investments, which leaves many families lopsided.https://www.youtube.com/embed/VODb-LDrO9U5302022-12-08 https://familybusinesses.com/fireside-chats/5hbfq1j7jRk/2026-09-29https://i.ytimg.com/vi/5hbfq1j7jRk/hqdefault.jpgIf you're worth 100 million dollars, one mistake can cost you 1 million dollars.A family office is an investment solution for families or individuals worth $10 million to several billion dollars, and it comes in three types: a virtual family office for families worth roughly $10 million to $50 million, a single family office with a dedicated full-time team, and a multi-family office serving many ultra-wealthy clients. The case for having one starts with defense, because mistakes grow with wealth: a $1 million net worth might risk a $100,000 mistake, while a $100 million net worth can produce a $1 million mistake. Tracking dozens of LLCs, equity stakes, K-1s, trust documents, wire deadlines and state tax letters is described as a part-time job in itself. A family office also helps on offense by directing the family's time and money toward the best return. Richard C. Wilson frames it as managing everything that touches the balance sheet, including tax, charitable giving, next generation planning and values.https://www.youtube.com/embed/5hbfq1j7jRk2772022-12-05 https://familybusinesses.com/fireside-chats/E_QlWxWDKLA/2026-09-29https://i.ytimg.com/vi/E_QlWxWDKLA/hqdefault.jpgTransferring business and real estate interests to children can let real estate losses offset income.Tom Wheelwright, a CPA with 40 years in tax and the author of Tax-Free Wealth, explains how business owners who cannot qualify as real estate professionals can still use real estate losses by transferring interests to their children or to trusts for them. Most people have children, parents or someone else to whom they can transfer an asset while keeping control. In his example, a family transfers an interest in an S corporation, held through a qualified subchapter S trust or grantor trust, and close to 100% of a real estate company to children who do not work in the business, so about $98,000 of passive real estate losses offset $100,000 of passive business income. He calls real estate the biggest tax shelter available. He cautions that results depend on jurisdiction, whether a person is active or passive, and the effect on estate planning, and notes owners can still pay themselves a salary.https://www.youtube.com/embed/E_QlWxWDKLA5132021-04-02 https://familybusinesses.com/fireside-chats/4qwdvhq7euk/2026-09-29https://i.ytimg.com/vi/4qwdvhq7euk/hqdefault.jpgA 529 is marketed as the kids' college account, but it's really a wealth transfer tool.The guests explain that most people see a 529 plan as the kids' college savings account, but the children never have rights to the money, and the plans are most valuable to the kind of wealthy families a family office serves. He lists four features: education, wealth transfer, long-term care and disability planning, and asset protection. When the owner dies, the successor owner inherits the account outside the estate, free of estate tax. One guest describes grandparents in their 70s with six children and 36 grandchildren who opened 42 accounts and moved six to seven million dollars out of their estate using 529s. The guests also note that 529 plans now accept $500,000 or more per beneficiary, far beyond the small annual contributions many people assume.https://www.youtube.com/embed/4qwdvhq7euk15942021-02-24 https://familybusinesses.com/fireside-chats/eTNkMyZUrC8/2026-09-29https://i.ytimg.com/vi/eTNkMyZUrC8/hqdefault.jpgMorgan Stanley's family wealth directors plan multi-generational wealth transfer, including venture and private equity holdings.Bill Atha, one of about 250 family wealth directors at Morgan Stanley, says his work covers multi-generational wealth transfer and pre-liquidity events such as an IPO, merger, divorce or real estate sale. He describes software his team uses to model multi-generational wealth transfer across an entire estate, including venture capital and private equity holdings. The firm's investment bank looks at companies from about $50 million and up, and sometimes $35 million to $40 million, for IPO and merger preparation. A lifestyle service group acts like a concierge for family offices, from yacht work to loans against fine art, and typically wants $10 million on the platform, or about $100 million for bill-paying assignments. His advice is simply to call with whatever need a family has rather than worrying about minimums.https://www.youtube.com/embed/eTNkMyZUrC86502021-01-25 https://familybusinesses.com/fireside-chats/ySvE_dzNLPQ/2026-09-29https://i.ytimg.com/vi/ySvE_dzNLPQ/hqdefault.jpgFamilies often fail to make their wealth creation story and its meaning clear to everyone.Richard C. Wilson says many families fail to make clear to every family member what the family's wealth creation story is, why the wealth exists and what it represents. He describes common cautionary tales: one child is put in charge of the family business while another is never formally invited, a son hires a college roommate, or a family member who loses the business is cut off. One of the biggest mistakes he sees is a family getting liquid and immediately buying a dream house, such as a family that sold its company for close to $1 billion and bought a house for more than $20 million. As an alternative to large inheritances, he describes families paying for college, a first home or medical emergencies, and otherwise funding children's pre-approved business ideas, with elders acting as a board of advisers. He also explains the difference between a single family office and a multi-family office serving 10 to 200 ultra wealthy clients.https://www.youtube.com/embed/ySvE_dzNLPQ39832020-04-17 https://familybusinesses.com/fireside-chats/PgJJI0B6qhY/2026-09-29https://i.ytimg.com/vi/PgJJI0B6qhY/hqdefault.jpgA family office dashboard costs nothing, yet many $100 million families still lack one.Speaking to private investors, Richard C. Wilson walks through 18 strategies to become a more effective investor, drawing on more than 2,000 family offices he has met in person. He says every family should have a free, one-page planning document covering its mission, wealth creation story, values and objectives, yet many $100 million families with full-time teams still lack one. He shares the family values plaque he grew up with and notes that investors who once only bought funds or single-family rentals now pursue direct deals, sometimes investing in a sponsor's main operating company instead of a single deal. He also points out that very different deal terms, such as a 6% preferred return with 50% of profits or an 8% preferred return with 20% of profits, are both described as industry standard. Finally, he argues that a company already doing about $1 million in revenue has removed nine of the twelve risks a start-up faces.https://www.youtube.com/embed/PgJJI0B6qhY36472020-04-14 https://familybusinesses.com/fireside-chats/folCm_Ww5_8/2026-09-29https://i.ytimg.com/vi/folCm_Ww5_8/hqdefault.jpgWhen a second generation took over, its family's real estate strategy shifted to hotels.A panelist from Procaccianti Companies, an organization built around a second-generation Rhode Island real estate family, says the family has completed more than $5 billion of real estate transactions over 60 years, and that when the second generation took over about 30 years ago the strategy shifted to hotels and hospitality, with more than 170 hotels acquired, owned, operated or developed. This year the panelist's team deployed about $75 million of equity into hotel acquisitions, often partnering with other family offices and ultra high net worth individuals. A self storage investor who sold a portfolio to a public REIT is growing from 10 to 100 properties, noting that about half the market is owned by mom-and-pop operators. Richard C. Wilson notes that about 75% of the club's family offices invest in real estate, averaging about 25% of their portfolios. Panelists add that a group of three or four family offices can hold a strong deal that a private equity partner must exit because of its mandate.https://www.youtube.com/embed/folCm_Ww5_818042020-04-09 https://familybusinesses.com/fireside-chats/_f7RdvjbiII/2026-09-29https://i.ytimg.com/vi/_f7RdvjbiII/hqdefault.jpgA client's grown daughter was told to build her own life before joining the family business.A multi-family office executive recalls a large client's daughter, in her mid-20s, asking whether she should quit her job to join her mother in the family's philanthropic and private investment business; he advised her to build her own life and career first. Panelists include an executive whose firm oversees more than $8 billion for about 110 families and another whose firm manages about $26 billion for about 2,000 clients. One panelist notes that real estate families often still hold 80% of their assets in real estate, sometimes concentrated in a single neighborhood, while his US clients are 30% to 40% globally diversified. Another firm limits any passive direct investment to 1% of a client's portfolio. Panelists add that family needs change over 5, 10 and 20 years as children become adults and join the picture.https://www.youtube.com/embed/_f7RdvjbiII27932020-01-24 https://familybusinesses.com/fireside-chats/sOVvDnz6p6E/2026-09-29https://i.ytimg.com/vi/sOVvDnz6p6E/hqdefault.jpgThe most effective $100 million-plus families typically split their portfolios into three compartments.In a live Q&A webinar, Richard C. Wilson says the most effective families with $100 million or more typically break their portfolios into three compartments, starting with a diversified market exposure component. He estimates there are more than 15,000 family offices globally and a growing number of centimillionaires. In a benchmark study of 180 family offices, 75% invested in real estate outside their private homes, making up an average of 25% of their portfolios, which is why real estate comes up so often. On raising capital, he says the worst approach is to blast 500 people hoping 20 reply, four take a call and one invests, because credible, trusted deals need a crafted approach. He also warns that families with dozens of LLCs and large incomes can overwhelm advisers who are used to serving much smaller businesses.https://www.youtube.com/embed/sOVvDnz6p6E44072019-05-10 https://familybusinesses.com/fireside-chats/SMShFTtKT6k/2026-09-29https://i.ytimg.com/vi/SMShFTtKT6k/hqdefault.jpgIn a family business, multiple generations are involved and multiple family members run the business.Richard C. Wilson explains that what makes a family business different is that multiple generations are involved and multiple family members are running it, such as siblings in their 50s and 60s bringing in the next generation, or an 80-year-old whose children and grandchildren help run the company. That creates trust and estate issues, and siblings can feel slighted if others earn more by working in the business, which leads to succession and governance problems. He notes that family businesses are not necessarily small: many oil and gas companies are family run with $30 million to more than $100 million in revenue, and hundreds of family businesses have billions in revenue. A business that has lasted for generations, supporting 10 to 50 or more employees over 15 to 30 years, is doing something right.https://www.youtube.com/embed/SMShFTtKT6k2352014-12-02 https://familybusinesses.com/fireside-chats/X_U6CJznFVU/2026-09-29https://i.ytimg.com/vi/X_U6CJznFVU/hqdefault.jpgFamily offices in non-Western countries are mostly funded by first-generation wealth, which takes more risk.Recording in Zurich while chairing a conference, Richard C. Wilson compares family offices across Western and non-Western countries. He says the biggest difference is how widely known the family office concept is, estimating about 5,000 family offices in the United States and close to 10,000 globally, with competitive models in the West. He notes that in Israel only two or three family offices provide a full service model for the whole country. In Australia, the Middle East and parts of southern Asia, he finds that first-generation wealth from founders who sold or took a business public is driving growth, and that such wealth generally takes more risk.https://www.youtube.com/embed/X_U6CJznFVU2882013-04-07 https://familybusinesses.com/fireside-chats/YvD8EavmA7w/2026-09-29https://i.ytimg.com/vi/YvD8EavmA7w/hqdefault.jpgFamily offices now release wealth to children in stages, such as at ages 18, 27, 35.Richard C. Wilson explains that many family offices now include a discretion clause in wealth transfer, releasing some money to children at age 18, some at 27, some at 35 and some at 50. Multi-generational wealth management means planning how wealth moves from a patriarch or matriarch who sold or took a business public down through each generation. He says this is central to what family offices do, and becomes more important the larger the family and the wealth. He also notes families setting up trusts in places such as New Zealand, Singapore, the Cayman Islands and Bermuda, and warns families to get to know and trust any adviser before letting them handle multi-generational planning.https://www.youtube.com/embed/YvD8EavmA7w2572013-04-06 https://familybusinesses.com/fireside-chats/x6TPG-Ut2DE/2026-09-29https://i.ytimg.com/vi/x6TPG-Ut2DE/hqdefault.jpgSeventy percent of Western family offices serve inherited wealth, but in Asia that is reversed.Speaking at a private equity conference in Singapore, Richard C. Wilson says about 70% of family offices in the United States and Western Europe serve second, third or fourth generation wealth, while in Asia that is reversed, with perhaps 40% to 60% or more first-generation wealth. He shares strategies drawn from interviews with 36 top family offices and his own experience raising more than $250 million from wealth management firms and family offices. He admits he once charged clients $10,000 a month retainers and went 13 months without raising any capital. His advice includes spending 60% to 80% of investor meetings asking questions, focusing on a narrow investor type instead of 20 sources, and publishing expert content such as white papers. He notes that family offices generally are not seeking 35% returns and do not want to be ignored by large funds that see their $10 million or $50 million as too small.https://www.youtube.com/embed/x6TPG-Ut2DE18082013-04-06 https://familybusinesses.com/fireside-chats/RXI1wcRBZec/2026-09-29https://i.ytimg.com/vi/RXI1wcRBZec/hqdefault.jpgChildren should inherit money by creating money, not by being handed money to spend.Next generation planning works best when children learn to earn money rather than receive it, and when the family has written values. Richard C. Wilson describes a lemonade stand his daughters ran to pay for a $400 toy Tesla, which brought in $250 in 90 minutes, as an early lesson in creating value. He notes that out of 40 ultra-wealthy workshop attendees, every one had company values and none had family values on the wall at home, while his family has 10 values posted above the kitchen table. His own plan funds education, medical emergencies and a first-house down payment of up to $150,000 or $200,000, and otherwise gives family money only as backing for business or real estate ventures approved by family elders. He urges families to decide these rules early so their trust and estate attorney can structure them.https://www.youtube.com/embed/RXI1wcRBZec582 https://familybusinesses.com/fireside-chats/B1yFOGFn9H4/2026-09-29https://i.ytimg.com/vi/B1yFOGFn9H4/hqdefault.jpgNot custom structuring fees and legal terms is a bigger mistake than an overpriced home.The costliest family office mistakes come from a lack of clarity and intentionality, and many are avoidable before any money moves. Richard C. Wilson lists keeping weak carryover advisors instead of layering a proactive tax planner or strategic legal advisor on top, and spreading money across startups that amount to lottery tickets. He warns against buying a $20 million dream home at the top of the market, citing a client who bought a $15 million island home and rotated it 40 feet for a better ocean view, since super luxury homes can drop $3 million to $10 million in value. The largest mistake he names is accepting standard deal terms instead of negotiating custom fee structures, co-GP deals, LLC share classes, co-investment rights and tag-along, drag-along or non-dilution rights. Even at $3 million to $10 million of net worth these errors can cost hundreds of thousands of dollars, and at several hundred million they can cost millions.https://www.youtube.com/embed/B1yFOGFn9H4285 https://familybusinesses.com/fireside-chats/ow1HUEjxmCs/2026-09-29https://i.ytimg.com/vi/ow1HUEjxmCs/hqdefault.jpgThe next generation inheriting the wealth allocates to alternatives three times as much as mine.A panelist says the generation inheriting family wealth allocates to alternative investments at three times the rate of his own generation, moving from 6% to 18% in one generation, as about $69 trillion changes hands. Another panelist, from the second generation of a family whose father sold cash registers and grew a barcode distribution business to 90% of its market through a relationship with Sam Walton, now runs a nine-family multi-family office with 22 stakeholders. A corporate venture investor describes backing more than 35 construction and real estate technology companies since 2019, pointing to about 650,000 unfilled skilled construction jobs. Panelists also discuss a $400 million recapitalization of manufactured housing lots in Dallas and Houston, and note that 32% of venture financings in the first quarter of 2024 were down rounds. The closing advice centers on long-term thinking: families investing on 5, 10 and 20 year horizons face very little competition.https://www.youtube.com/embed/ow1HUEjxmCs2030 https://familybusinesses.com/fireside-chats/bNqeBypu1kQ/2026-09-29https://i.ytimg.com/vi/bNqeBypu1kQ/hqdefault.jpgThe generation that inherits wealth can never really understand the struggle of how it was built.Asked what they would tell someone who just came into serious wealth, one family office principal, whose parents came to the country as immigrants with nothing, says to spend time with family, because the money has to have a purpose beyond itself and the generation that inherits it can never really understand how it was built. He says legacies are built at the dinner table. Another panelist says to check whether anyone trusted with your money has skin in the game and will lose money alongside you. A third says to decide first whether to be a family office at all, since there are ways to get the benefits without one, and notes that many people build single family offices even though they are not in the investment business. Another principal made a rule 11 years ago to build trust only with people he would leave his children with.https://www.youtube.com/embed/bNqeBypu1kQ555 https://familybusinesses.com/fireside-chats/ciLkrwr72dI/2026-09-29https://i.ytimg.com/vi/ciLkrwr72dI/hqdefault.jpgCapital preservation can sometimes be at odds with establishing a legacy, and families must balance both.A panelist says capital preservation can sometimes be at odds with establishing a legacy, and that families with wealth need to balance the two. Another principal, who made his money in Silicon Valley tech exits and then real estate, is building a family office with his partner, a second-generation family office member whose family sold surgery centers; together they chose a simple, deliberately unexciting system built on real estate for capital preservation. A third panelist runs an office representing two generations of a Midwest family, relying on 45 years of relationships to find opportunities such as next-generation chips. Another founded a multi-family office after growing up in an entrepreneurial family and says AI now produces in five minutes a family tax and allocation summary that once took 60 hours. One family's approach is to identify value independent of price, on the view that the price follows once the story of that value is told.https://www.youtube.com/embed/ciLkrwr72dI712 https://familybusinesses.com/fireside-chats/E5DlLxp5Er0/2026-09-29https://i.ytimg.com/vi/E5DlLxp5Er0/hqdefault.jpgPrivate investors should focus on one or two areas and meet dozens of operators before investing.Richard C. Wilson presents strategies for private investors, family offices and heirs, advising them to focus on one or two areas and meet 10, 20 or 50 operators, such as 30 self storage independent sponsors, before picking the best two. He says most of his clients hold $50 million to $100 million, up to about $900 million, and that almost all families above $15 million to $30 million end up buying apartment buildings or self storage. He encourages families to define their wealth creation story, which for many means adding value to employees, family and children. For direct investments, he explains gross revenue royalties, which let an investor tie returns to revenue rather than waiting on profits, targeting 1.5 to 2.25 times the money back. He describes a process that screened 375 consumer product companies, spoke with 70, found eight investable and closed two investments.https://www.youtube.com/embed/E5DlLxp5Er03137 https://familybusinesses.com/fireside-chats/LnZGytqKTtg/2026-09-29https://i.ytimg.com/vi/LnZGytqKTtg/hqdefault.jpgTony Robbins with Richard C. WilsonTony Robbins | Fireside chat with Richard C. Wilsonhttps://www.youtube.com/embed/LnZGytqKTtg0 https://familybusinesses.com/fireside-chats/r56Yee-6RAU/2026-09-29https://i.ytimg.com/vi/r56Yee-6RAU/hqdefault.jpgMy daughter reads our family values, in ViennaRichard C. Wilson and his daughter | Vienna, Austria | Family valueshttps://www.youtube.com/embed/r56Yee-6RAU0