#278 Is Traditional Financial Planning Broken for Doctors? ft. Austin Dean of Waystone Advisors

Austin Dean and Waystone Advisors

Austin Dean, founder of Waystone Advisors, shares how his firm helps clients rethink money. Instead of only planning for retirement decades from now, his team focuses on creating flexibility and freedom today.

Most advisors push retirement accounts and tax-deferred savings, but Austin calls this “money jail”; your wealth is locked away until you’re 60. He believes wealth should give you options now, not just in the future.

The wealthy don’t just save in retirement accounts. They start businesses, invest in real estate, and use debt smartly. Austin helps his clients do the same by building cash flow and flexible assets.

For doctors and high earners, this is a game-changer. Many have high net worth on paper but little control over their cash. Austin’s approach solves that problem.

Getting Comfortable with Alternatives

Peter points out that alternatives like real estate or private lending can feel intimidating. Austin agrees; he learned by making small mistakes in early deals.

Instead of giving up, he built a system to evaluate opportunities: checking audited financials, asking about exit strategies, and meeting operators directly. This hands-on approach gave him real-world knowledge.

Most advisors avoid alternatives because sticking with the stock market is easier. But Austin’s personality pushes him to question everything and look for better ways.

He treats each client’s financial picture like a puzzle. If the traditional path doesn’t work, his team designs a new one with alternatives that actually match their goals.

Doctors Want Flexibility, Not Just Retirement

The pandemic changed how many doctors think about their future. The old plan (work until 65, then retire) feels outdated.

Austin sees more doctors wanting “work optionality”: the ability to choose their hours, slow down, or work for passion instead of necessity.

Many have saved in 401(k)s and deferred comp plans, but still feel stuck. They want income streams that let them live with more freedom today.

Alternatives like real estate or private lending can be structured actively (hands-on) or passively (hands-off), depending on what fits a client’s lifestyle and goals.

The Power of Cash Flow and Resilient Portfolios

Cash flow is often the missing piece. Many high earners chase tax deductions, but what they really want is income that replaces their paycheck.

Austin warns against blindly following conventional advice. Having all your money in retirement accounts may grow your net worth but won’t give you usable cash.

Instead, he teaches “nontraditional diversification.” A strong plan mixes stocks and bonds with alternatives like real estate, lending, insurance, and lines of credit. This way, you’re prepared for any market, up or down.

Resilient portfolios are built by defining goals first. Someone who wants freedom in 5 years will invest differently than someone who’s happy working for 20 more.

Bigger Impact and Key Takeaways

Austin reached financial independence years ago but chose to keep building Waystone Advisors to help more people. Now his firm serves clients in 40 states, with hopes to expand nationwide.

He believes financial freedom doesn’t mean leaving medicine. For many doctors, it means enjoying medicine more by working on their own terms.

This mindset shift, toward flexibility and purpose, is what excites Austin about the future. His goal is to help thousands of professionals achieve that.

If there’s one point he wants listeners to remember, it’s this: you don’t have to follow the traditional path. There are other ways to build wealth that can give you freedom much sooner.

He closes with:

“There is a different way than you’ve been taught. Financial independence could be closer than you think.”