Breaking Free From 90s Financial Advice W/Will Davis
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Episode Description
In this episode of the On The Rise Podcast, host Jeremy Dyer sits down with Will Davis, a Denver-based real estate professional and financial educator who helps families achieve financial independence by challenging the conventional wisdom most of us were raised on. Will breaks down why the financial playbook from the 1990s — steady job, pay off debt, max out retirement — no longer works in today's inflation-driven economy. He introduces a cash flow-first framework and explores strategies like the hybrid income model and infinite banking as practical paths toward true financial freedom. This is a must-listen for any family that feels like they're doing everything right but still falling behind.
Summary
1. The 90s Financial Playbook Is Outdated The advice most families follow today — get a good job, pay off debt, max out retirement accounts — was built for a different economic era. Will Davis argues that this conventional wisdom fundamentally fails to account for the realities of modern inflation, leaving hardworking families financially stuck despite doing everything "right."
"These people that were acing 90s financial advice were barely, barely able to get a house."
2. Inflation Is the Root of the Problem The single biggest reason 90s financial advice no longer works is inflation. Between 2020 and 2022 alone, $5 trillion was printed in three years, effectively cutting the purchasing power of a $100,000 salary by roughly 20%. Families on fixed W-2 incomes have no mechanism to recapture what inflation quietly steals from them.
"If you had a $100,000 salary in 2020, you basically took a 20% pay cut over the three years, four years of COVID."
3. Older Generations Unknowingly Give Harmful Advice Because 90s financial advice worked for prior generations, many older mentors and family members communicate that younger families simply aren't saving or budgeting hard enough. Will points out that this creates a damaging and inaccurate narrative — one that ignores structural economic changes and leaves younger families feeling blamed for circumstances largely outside their control.
"90s financial advice as a whole does have a very condescending, punitive, disrespectful tone to it — like you need to lock it up, control your expenses, figure it out."
4. Cash Flow Is the Real Goal Whether you're earning, managing, or investing money, the guiding principle should be cash flow — not appreciation. 90s financial advice is built around appreciation-based strategies like the S&P 500 and home equity paydown, but those vehicles don't generate the ongoing income needed to outpace inflation over time.
"You need to have a plan to outpace and stay ahead of inflation forever with cash flow."
5. The Hybrid Income Model Is the New Standard Will recommends that families keep their W-2 job while building a secondary income source that meets three criteria: it can be controlled, it can be scaled, and it leads to multiple streams of income. This hybrid model reduces vulnerability to layoffs, inflation, and unexpected life changes.
"The future is a hybrid worker — somebody who's got a W-2 job, and then also has a source of income that they can control, scale, and that leads to multiple sources of income."
6. Locking Up Capital Has a Hidden Cost Strategies like aggressively paying down a mortgage or contributing to 529s and HSAs tie up capital in places where it can't be accessed or redeployed. Will emphasizes the concept of opportunity cost — money that's locked away isn't working for you, even if it feels financially responsible.
"You're paying your mortgage down — you don't get any benefit from that until the mortgage is paid off. The capital is gone. It can't be used for anything else."
7. Properly Structured Whole Life Insurance Is a Wealth Tool Not all whole life insurance is created equal. When structured correctly, permanent life insurance — specifically through the infinite banking concept developed by Nelson Nash — offers guaranteed growth, liquidity, and favorable tax treatment. It allows the same dollar to serve multiple financial purposes simultaneously, a key advantage for investors.
"There are terrible whole life policies and people that structure them very poorly — and there are amazing policies that are structured very well and very much help with wealth building and wealth efficiency."
8. Wealthy Families Invest Differently High-net-worth families and family offices typically limit their stock market exposure to 20–25% or less of their portfolio. The bulk of their wealth is built through cash-flowing assets. Replicating this allocation strategy — rather than concentrating 100% of liquid net worth in the market — is one of the clearest paths toward building lasting financial independence.
"When you look at eight and nine figure folks and family offices, they typically limit their allocation to 20 to 25% or less in the stock market."
“My grandfather would invite us to help with the property… even when we were kids.”
Trey’s family built wealth through real estate over multiple generations, but the key was not just investing. His grandfather intentionally involved children in real estate projects early, teaching responsibility and ownership. These small experiences built a long term mindset around investing, stewardship, and wealth creation.
Resources and Links
Website: familyfirstmethod.com/ontherise
Linkedin: https://www.linkedin.com/in/will-davis-9a167b59/
Free Resource: Will offers a free downloadable gift and hosts a free monthly four-day Zoom challenge covering the problems with 90s financial advice, the solution, implementation, and the long-term vision for families.
