82 fireside chats with family business owners, next gens, and the family offices buying companies like theirs. Every one has a full transcript.
Updated September 26, 2026
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We really wanted both of our boys to make decisions and make mistakes.
Structural steel | founded 1992 in a garage as D&D Welding | renamed 2010 | 75 employees | father and son
Asian families with children studying in the U.S. join a next-generation mentorship program.
Boutique family office advisory | 11 years at two single family offices | three Asian family clients in its first year | next-generation mentorship for ages 20 to 35
95% of what is out there in family office structures is flawed.
Trust, estate and tax attorney | about 40 years | 130+ billionaires represented | about 600 family offices
Most people do not speak to Gen 2 or Gen 3 with enough respect.
Live panel | Beverly Hills Investor Club Summit | second-generation inheritor | family office principals
There's always somebody more successful and somebody wealthier than you, so don't try to prove something.
Live panel | Beverly Hills Investor Club Summit | outsourced multi-family office for pre-liquidity families | Sunburst Ventures | Core Family Office
They exited for $2.2 billion by focusing on lifetime value, not just acquisition cost.
Original Shark Tank investor | 500+ products launched | 20 businesses past $100 million | Celsius board member for 12 years | invests with his son, brother and niece
By generation three there's a loss of the family ethos, and the family office splinters.
Live panel | ultra-wealthy investor mandates | distressed multifamily bought at 40% of 2022 prices | trust protectors and seven-generation thinking
Tell us who you are, how you've failed and what you learned before asking to partner.
Live panel | $1 billion+ investors | multi-family office in Lehi, Utah | a single family office turned credit firm with about $1 billion in originations | $2.2 billion real estate platform
Our prime mission is to keep a family together and not let wealth destroy it.
Family Wealth Leadership | multi-family office run with his son | families from $25 million to $300 million | family foundations and boots-on-the-ground philanthropy
Wealth attracts predators, so elderly family members need protection from scams and undue influence.
Keynote | protecting heirs and elders from fraud | a scam that took $1.5 million from her sister | no will changes without approved witnesses | no check-writing privileges for employees
Very wealthy people are often quite cheap, especially if they earned the money themselves.
Second-generation family office executive | Sunburst Ventures | 30+ years in finance and private investing | Florida and Puerto Rico | works with her sons
My grandchildren's grandchildren will still be developing that piece of land.
International tax and corporate lawyer since 1992 | work in about 43 countries | 25 boards | 3,000 acres in Central America | owner of a European pro football team
Oil and gas investments have historically built generational wealth, and the key is patience.
President, Pecos Valley Partners | third-generation energy investor | family office in oil and gas since the mid-1980s | conventional vertical wells up to 10,000 feet
A non-dilutive equity stake can be worth far more than a larger share that gets diluted.
Keynote by Richard C. Wilson | Family Office Formula event | 30 mental models of wealthy business builders | negotiation and deal structures
The skills needed to create wealth are often opposed to the skills needed to preserve it.
Whittier Trust | founded 1935 as the Whittier family's single family office | 6th generation served | about $26 billion under management
Raise $100,000 first, then a quarter million, then a million, not $50 million on day one.
Live hot seat webinar hosted by Richard C. Wilson | founders and capital raisers | investor relations and strategy | about 2 hours 50 minutes
The most important strategic asset we acquired was mindset.
2nd generation | Sun West Mortgage, started with less than $100,000 | multi-billion dollar national lender | first AI program in 1985
When you partner or exit your family business, make sure you pick the right partner.
Live panel | TAG Associates, an $8 billion multi-family office | private equity in Hispanic family businesses | deal with no debt that tripled revenue
Families go to 10 different advisers, get 10 different answers and end up doing nothing.
Live panel | Private Investor Summit, Dallas | multi-family office and wealth management executives | senior living | patient capital
Hard, verifiable numbers in a one-liner make investors lean forward more than claims of being big.
Live panel | investors rate audience one-liners and brand names | fourth-generation partner in two 100-year-old real estate companies | $520 million fund platform
Don't just measure return on investment, measure your return on engagement.
Live panel | Hawaii Family Office Retreat | lower middle market acquisitions | $20 million to $100 million enterprise value
Set up a generation-skipping trust and put assets in it while their value is low.
Live panel | off-market deal sourcing in minerals and real estate | generation-skipping trusts | small-balance commercial real estate | litigation finance
One family office portfolio is 100% alternatives, with zero public market exposure by design.
Live panel | Hawaii Family Office Retreat | Dubai-based single family office CEO | former CIO of a multi-generation Pittsburgh family | mobile home park fund
Most real estate transactions get into trouble because they run out of time or money.
Live panel | real estate for the next decade | brokerage with 200,000 agents | private lending at 9% to 11% | physician-backed regenerative communities
Philanthropy lets parents watch which children will rise to the occasion.
Live panel | AI and technology in family offices | family foundations as a training ground | Maybach family mentoring legacy since 2005
I made it a priority 20 years ago to start having my kids travel with me.
Live panel | biannual family governance retreats for 25 years | 5 children, 18 grandchildren | own family office for 7 years
Mom and dad doing estate planning by themselves is going to be a disaster.
Live panel | Maybach family legacy foundation | second-generation family office after a 2014 exit | multi-family office for families under $250 million
The second generation was ready to retire, but the third still had gas in the tank.
M&A investment banker | former Accenture, Countrywide, Bank of America, Deloitte and Grant Thornton | nine-figure sale of a three-generation family company
Starting a business just to make money and exit is a terrible business plan.
Family office founder | about $11 billion in transactions | about 25 years in commercial real estate and finance | senior housing with the Catholic Church
Anyone in business for the next 30 years had better learn accounting.
Chairman and CEO, McGovern Capital | co-founded 25+ companies, six world category leaders | 15+ global joint ventures in 80+ countries | his son is on his team
Moving a family from ad hoc decisions to formal governance is extremely hard.
Multi-family office founder | Los Angeles | global real estate, credit and growth investments | works with his father
Compounding started when we decided we were in the wealth business with one client: our family.
25+ years in real estate | 25 years in corporate before entrepreneurship | private lending business started in 2017 and sold in 2024 | built a family office from scratch
Many of my families are moving from G1 to G2 and looking to exit their businesses.
Multi-family office principal | background in politics and real estate | shoring up private credit for families exiting businesses | the coming generational wealth transfer
Owning a strategic choke point, such as a leading industry expo, can create lasting deal flow.
Keynote by Richard C. Wilson | strategic choke points | deal flow and M&A outreach | gross revenue royalties and anchor investors
A lot of fourth-generation family companies struggle because the families remember old grudges.
Live panel | allocators managing $1 billion+ | healthcare at a $2.9 billion family office | Salinas agriculture group with 13 companies | Bronx real estate fund
It took 20 years before we were able to turn it around and sell.
Co-founders, Barefoot Wine | started 1985 | office in a laundry room | sold after 20 years | authors of The Barefoot Spirit
He was a third-generation pro athlete and was still rejected by over 850 colleges.
Third-generation pro athlete | sixth-generation college graduate | rejected by 850+ Division I colleges and 10,000 scouts | speaker on vision and learning
Pouring $5 or $10 million into children kills their motivation to do something.
Keynote by Richard C. Wilson | free tools for ultra-wealthy families | family values | funding children's businesses instead of handing them money
Many families lose critical people when they don't appreciate those who take care of their investments.
Former Chase workout banker | bought 11 companies in 11 industries with billionaire family capital | bank board member for 13 years | works with a billionaire family's children
Let experts manage 90% of your money and keep 10% to play with.
Co-founder, E! Entertainment Television | launched with $2 million, 11 employees and 31 interns | son of immigrants, raised in Brooklyn
The chances of a family business lasting a hundred years are one in a thousand.
Henderson Estate Company since 1840 | Perdue family business since 1920 | about 70 Henderson family members | annual reunions since 1890
I didn't wait till I was done to start spending time with my children.
Co-founder, Express Locations | 150 T-Mobile stores | 1,400 employees | about $600 million revenue | sold 2017 | family office run with his sons
There is always somebody you can inspire, because somebody younger than you is watching.
Former NBA player | 10 NBA seasons | investing in private equity since 2019 | children's book author | sets yearly goals with his daughters
My biggest mistakes were failures to invest, including the seed rounds at Google and Facebook.
Founder, Draper Associates, DFJ and Draper Venture Network | seed investor in Tesla and SpaceX | Draper University: 3,500 students, about 900 companies
Even full-time capital raisers usually approach 200 to 250 investors to find 14 to 20 yeses.
Closing remarks by Richard C. Wilson | Private Investor Mastermind, Texas | outsourced CFO support | capital raising realities
Massive output, from teenage flyers to 500 blog posts, built Wilson's family office business.
Opening remarks by Richard C. Wilson | Super Summit day one | brute force strategy | 7 case studies from his career
Global asset protection used to be hide-and-seek, and now it's show-and-tell.
International asset protection attorney | work in 43 countries over 34 years | 30 corporate boards | ECI Development, founded 1996 | 4,000 acres in Central America
Removing stress and toxicity from a business can make everything, including growth, go faster.
Keynote by Richard C. Wilson | 7 ways to have the most fun year of your life | business, investments and health | delegation and persistence
My generation doesn't necessarily want to invest the way our parents invested.
Live panel | deal flow nobody else sees | next-generation investor, age 39 | minority stakes in 24 medical and dental practices | former Google executive and angel investor
Legal documents alone can't solve the wealth transfer problem, because there's an emotional part.
Credo | high net worth clients from Sun Valley to San Francisco | fractional CFO for families | average family has about 27 advisers
At 22, like his NFL rookie son, a former pro wasn't thinking about investing.
Live panel | former pro athletes as investors | a father guiding his son's first NFL year | a first-round pick who chose college | NFL Sisters in Service
Profitable businesses with 50 to 100 employees are winding down because there is no succession plan.
Founder, Syndicate Venture Group | 12-year military veteran | first acquisition: $8.6 million business with no money down | service businesses from retiring owners
About 70% of families don't make it to the next generation, mostly because of family quarrels.
Billionaires.com mini-series, episode 5 | Henderson family business since 1840 | Perdue family business | Henderson family reunions since 1890 | research of Dennis Jaffe
Being a business owner is your chance to leave a legacy for your employees and community.
Billionaires.com mini-series, episode 3 | keynote at the 8th Annual Family Office Super Summit | Priceline founding team | dinners with families in 100 countries
Wilson hangs his family values above the kitchen table and urges every family to do likewise.
Opening remarks by Richard C. Wilson | Single Family Office Summit 2023 | 197th live event | how the Family Office Club began
Most families, even ultra wealthy families, don't have written family values.
Guest on The Investor's Podcast (TIP530) | founder of Family Office Club | has helped set up 200+ family offices | billionaire interviews for billionaires.com
Thomas Handler recommends keeping about 10% of net worth in an asset protection trust.
Guest talk by Thomas Handler | advanced asset protection | virtual family office and family holding companies owned by trusts | the stealth prenup
Almost no $100 million families have their values on the wall, though most companies do.
Talk by Richard C. Wilson | free resources for private investors and family offices | 67-field family office dashboard | family values and portfolio buckets
Most Family Office Club clients are first-generation founders or heirs formalizing a family office.
Solo talk by Richard C. Wilson | Family Office Club achievements in 2022 | $55 million put to work | who the club serves
It is 10 times more powerful to be well structured before a liquidity event.
Solo presentation | Episode 13 of 14 | anonymized client case studies | families worth $1 million to $1 billion+
You only need to become ultra wealthy once if you have proper defensive strategies.
Solo presentation | Episode 5 of 14 | family office team and service providers
If you're worth 100 million dollars, one mistake can cost you 1 million dollars.
Solo presentation | Episode 2 of 14 | virtual, single and multi-family offices | recorded at a Las Vegas conference
Transferring business and real estate interests to children can let real estate losses offset income.
Interviewed by Richard C. Wilson | CPA with 40 years in tax | former Ernst & Young national tax office | author of Tax-Free Wealth
A 529 is marketed as the kids' college account, but it's really a wealth transfer tool.
Hosted by Richard C. Wilson | Bill Atha, Morgan Stanley family wealth director | Chris Stack, Savingforcollege.com | 529 plans for wealth transfer, long-term care and asset protection
Morgan Stanley's family wealth directors plan multi-generational wealth transfer, including venture and private equity holdings.
Interviewed by Richard C. Wilson | Morgan Stanley family wealth director | one of 250 family wealth directors | pre-liquidity and multi-generational planning
Families often fail to make their wealth creation story and its meaning clear to everyone.
Webinar by Richard C. Wilson | family office success stories and cautionary tales | 250 events spoken at | 2,000+ face-to-face meetings with family offices
A family office dashboard costs nothing, yet many $100 million families still lack one.
Keynote and Q&A by Richard C. Wilson | 18 strategies for private investors | 2,000+ family offices met in person | deal terms and direct investing
When a second generation took over, its family's real estate strategy shifted to hotels.
Live panel | real estate firms that raised $20 million+ each | Procaccianti Companies, a second-generation Rhode Island real estate family firm | self storage, hotels and apartments
A client's grown daughter was told to build her own life before joining the family business.
Live panel | $1 billion+ family offices | a multi-family office overseeing $8 billion for 110 families | a firm managing $26 billion for 2,000 clients
The most effective $100 million-plus families typically split their portfolios into three compartments.
Live Q&A webinar by Richard C. Wilson | 200+ speaking engagements in 14 countries | 15,000+ family offices globally | benchmark study of 180 family offices
In a family business, multiple generations are involved and multiple family members run the business.
Solo video by Richard C. Wilson | recorded in Kuala Lumpur | defining a family business | succession and governance problems
Family offices in non-Western countries are mostly funded by first-generation wealth, which takes more risk.
Solo video by Richard C. Wilson | recorded in Zurich | how family offices differ around the world | first-generation wealth outside the West
Family offices now release wealth to children in stages, such as at ages 18, 27, 35.
Solo video by Richard C. Wilson | recorded in the Swiss Alps | multi-generational wealth management basics | staged wealth transfer
Seventy percent of Western family offices serve inherited wealth, but in Asia that is reversed.
Keynote by Richard C. Wilson in Singapore | 7 strategies to raise capital from family offices | interviews with 36 top family offices | $250 million+ raised
Children should inherit money by creating money, not by being handed money to spend.
Solo presentation | Episode 12 of 14, How to Start a Family Office mini-series | next generation planning
Not custom structuring fees and legal terms is a bigger mistake than an overpriced home.
Solo presentation | Episode 10 of 14 | $1 million+ family office mistakes | recorded after a workshop for 30 ultra-wealthy families
The next generation inheriting the wealth allocates to alternatives three times as much as mine.
Live panel | $1 billion+ family offices | second-generation founder of a nine-family office | construction tech venture | manufactured housing
The generation that inherits wealth can never really understand the struggle of how it was built.
Live panel | Single Family Office Summit | four family office principals | legacy, trust and whether to start a family office at all
Capital preservation can sometimes be at odds with establishing a legacy, and families must balance both.
Live panel | Single Family Office Summit | tech-exit founder building a family office with a second-generation partner | Midwest office spanning two generations
Private investors should focus on one or two areas and meet dozens of operators before investing.
Webinar by Richard C. Wilson | 17 strategies for private investors | clients from $50 million to $900 million | gross revenue royalties
Tony Robbins with Richard C. Wilson
Tony Robbins | Fireside chat with Richard C. Wilson
My daughter reads our family values, in Vienna
Richard C. Wilson and his daughter | Vienna, Austria | Family values
