Jan 18, 2026
While most parents dream of stability for their children, for some it’s an all-in quest for generational riches, pushing boundaries and taking extreme measures to build a legacy.
A recent Business Insider video pulls back the curtain on a group of parents who achieved financial independence by employing a range of strategies, from financially sensible to intense.
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Here’s how these parents hope to provide generational wealth to their kids, and with some savvy takeaways for families looking to build a dynasty of their own.
Growing up with less can change how you view money
Jeremy Jacobson grew up in a trailer in Minnesota. His earliest memories, he says, are of “deprivation.” Burdened by student loans, he felt constant pressure to get good grades. His wife, Winnie Tseng, grew up in Taiwan. Her parents couldn’t afford to feed her, so they sent her to an orphanage.
“I am afraid of spending money,” she told Business Insider. The couple bonded over their shared values about finances (1).
Ja’Net Adams grew up middle-class. But, as she puts it, “our middle class, as an African American family, is different than the American middle class.” She became a first-generation college graduate, but ended up with $50,000 in student debt and no safety net.
Sam Dogen learned money discipline early. His parents were frugal, so he got a job at McDonald’s at about 14 to have some spending money. He still remembers the embarrassment of running into classmates while he was working at the fast food restaurant.
Their childhood experiences shaped how each of them views money. They all put wealth-building strategies into motion, but turned up the intensity to reach their goals faster.
Dogen didn’t just “save more.” He ran the numbers in Excel and set a target of $3 million. He believed that if saving doesn’t hurt, you’re probably not saving enough. He spread his money across stocks, real estate, bonds and cash.
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Jacobson and Tseng took a simpler approach, putting everything in low-cost index funds to avoid the stress of hands-on management.
To crush debt, Adams made a brutal but temporary decision: no eating out, no vacations and no gifts for two years. Her goal was to wipe out $50,000 in debt before her second child was born, and she managed to do it, though her methods were severe.
Jacobson didn’t just budget. He restructured his entire life. He sold his house and car, rented a room, biked everywhere and tracked every dollar. Saving 50% of income wasn’t enough. It eventually climbed to 80%. Jacobson is now retired, but it came with years of extreme sacrifice.
Financial planners say scarcity thinking isn’t just about being careful with money. It’s a belief that there will never be enough. That belief can fuel fear-based decisions, pushing people to fixate on short-term worries. The result can be anxiety over everyday spending, even when bills are covered, and hesitation to make smart moves like investing. Over time, experts warn, fear-driven thinking can distort decision-making and chip away at financial confidence (2)
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What these parents demonstrated was discipline. Discipline can build wealth, and for them it paid off. For those who can’t or don’t want to be as intense, discipline can still support wealth-building in a more balanced way.
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How to teach your kids about money
Dogen reached financial freedom at 34 and became a stay-at-home dad and author. His kids, 5 and 8, don’t just hear about money; they see it in action. They help with landscaping their rental properties, where he hopes that they’re learning the value of work. Dogen worries that giving kids too much too early can kill motivation and dampen their drive later in life.
Jacobson and Tseng run a “mommy and daddy bank” for their kids, 10 and 5. Allowances and gift money go into savings, earn a bit of interest and can only spend half of it. Roth IRAs and 529 plans are already in place. The couple believe the biggest lessons come from watching how parents live and make money decisions.
Adams’ kids are older, 17 and 13, and both have Roth IRAs and savings accounts. If they want something, they pay for it. Her son JR said he’s learned how important it is to know what to do with money and not just use it when he feels like it.
You don’t have to save 80% of your income, sell your car or skip vacations to build generational wealth. For most families, a realistic playbook can include the following:
- Save consistently: You don’t need to start big. Automating savings turns it into a habit, and gradually increasing contributions as your income rises can make a difference over time (3).
- Invest early in low-cost index funds: Diversified index funds are popular with long-term investors because they keep fees low and let compounding work quietly in the background. The goal isn’t to beat the market, but to stay invested long enough for time to do the heavy lifting (4).
- Kill high-interest debt: Credit cards and other high-interest debt can drain your funds quickly. Paying it down matters, but it doesn’t mean total financial misery. Whether you tackle the highest rates or start with smaller balances for motivation, steady progress is what counts (4).
- Use tax-advantaged accounts like 529 plans or Roth IRAs: Those 529 plans allow education savings to grow tax-free, and newer rules allow unused funds to roll into a Roth IRA in some cases. Roth IRAs, including custodial versions for kids with earned income, can be powerful because decades of tax-free growth can turn small early contributions into long-term security (5).
- Build an emergency fund: A cash buffer of about three to six months of expenses helps families avoid dipping into investments or piling on debt when surprises hit. It’s one of the simplest ways to protect your progress.
- Teach kids about money: Open conversation about saving, spending, and investing helps children build confidence around money instead of fear or secrecy. Financial literacy is one of the most transferable forms of wealth (6).
- Plan for the handoff: Wills, beneficiary updates and basic estate planning can help ensure that whatever you build actually reaches the next generation, with fewer taxes, fewer delays and fewer family disputes.
Generational wealth doesn’t have to come from scarcity or extreme sacrifice. The parents featured in the video reached financial stability by using intense strategies that worked for them and helped accelerate their wealth. But many of those choices were shaped by financial struggles they experienced growing up. For most families, generational wealth is more likely to be built through steady habits, practical tools and a long-term mindset.
Article sources
We rely only on vetted sources and credible third-party reporting. For details, see our editorial ethics and guidelines.
Business Insider (1); Wondermind (2); Federal Deposit Insurance Corporation (3, (5); U.S. Securities and Exchange Commission (4); Consumer Financial Protection Bureau (6).
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Jessica is a freelance writer with a professional background in economic development and small business consulting. She has a Bachelor of Arts in Communications and Sociology and is completing her Publishing Certificate.
