When we enroll for health insurance through an employer, through the individual plan marketplace, or Medicare, the options are vast and complicated - anything but consumer friendly. When we need to use our insurance the financial impact can be massive. We are joined by Christine Simone, co-founder of Caribou, a firm that matches health care advisors to people in need of guidance.

Matt Pierce makes his podcast debut to talk about different ways markets might play out over the next decade and how investors can prepare accordingly. We discuss the following scenarios: - More of the same - market outcomes look like the last 10 years - Mean reversion - prices return to something more normal - Lost decade - below average stock and bond returns - Breakthrough - innovation drives unexpected productivity surge - Gloom and doom - our worst fears materialize, we enter a sort of depression

Kevin was inspired to take action upgrading his online security and shares the most practical and effective measures he has taken: Long and random passwords Password managers 2-factor authorization: basic and advanced Wireless network security

Cash is how we participate in the economy every day. But it pays almost no interest while it sits in the bank, and inflation is constantly eating away its purchasing power. My partner, Derek Ripp, joins us to talk about how much cash to hold, where to keep it, and strategies to get the most out of it.

The thought of investing in commercial real estate can be daunting, even for someone very comfortable with traditional residential investing. The transactions are bigger, the leases are different, financing is different, and on and on. We are joined by Austin-based commercial real estate professional, Spencer Holbert, to demystify commercial real estate investing.

Kevin explores the (surprising!) origins of what it means to be a 'maverick' and how that relates to investing differently from the masses. He talks about the reasons to consider being a maverick investor and the challenges of enduring the psychological torment that comes with the territory. He ends with practical examples from history and suggestions for how an investor should be prepared to take 'maverick risk'.

Inflation and aliens are on the minds of many. They are big, scary concepts that haven't played much of a role in our lives recently, but some fear they might. Inflation is personal, so Kevin breaks down a typical household budget and analyzes the impact of inflation. He considers the causes of inflation and offers consumers and investors tools that might help defend against it.

Kevin expands on his recent blog post about the sudden increase in home prices over the last 12 months and the options homeowners are considering to make the best of it, including: Sell and Move Stay and Improve Buy a Rental Rent and Move Do Nothing

Medicare is a complicated topic filled with jargon, confusing enrollment periods, and all sorts of private insurance bolt-on options. Cindi Gatton of Caribou joins us to make sense of it all. Timeline for enrollment - when do people need to start taking action? What are the common reasons people incur a penalty? How to avoid. What is not covered by Medicare? How to shop for supplemental plans: call brokers, online comparison tools, etc Evaluating supplemental coverage options - what is a proper framework for sorting through policies? What impact does a new health condition have when trying to sign up for or change supplemental plans? Maintaining current doctors? Some doctors not taking Medicare? How does working past age 65 impact Medicare coverage?