A Contribution to One of these is Probably Much Better than What You Give for Christmas and Birthdays
Note sull'episodio
A 529 plan is one of the best financial tools that too few people are using. If you’ve heard of them, then you know they can help families save for children’s higher education. But did you know adults can use them too, that they can cover some K-12 expenses, study abroad, student loans, and support people with disabilities? These incredibly versatile accounts are, sadly, woefully underutilized. That’s in part because finding the best plan for your circumstances can be a pain.
In true entrepreneurial fashion, Yosh Miller set out to change this. His company Hadley wants to make 529s as ubiquitous as 401ks. But as you will hear, the bureaucracy and perverse incentives he has to navigate are astounding.
1:14 Lionel is a 529 plan geek.
3:09 529s might be one of the most powerful yet misunderstood tools in the US tax code.
3:40 Yosh compares 529 plans to Roth IRAs: tax-free growth and tax-free withdrawals with broader eligibility.
5:04 They’re not just a college savings plan.
7:00 Hadley’s origin story
8:25 Yosh explains how state-by-state rules create confusion and why many Americans should shop across states for better plans.
11:50 From solving a personal problem to recognizing a systemic, nationwide issue
14:20 Yosh highlights the shocking inequity in 529 adoption, noting that the wealthiest Americans dominate participation.
23:00 A newly minted entrepreneur navigates big administrative hurdles
27:05 For Hadley, going through employers is the most efficient go-to-market strategy.
34:20 Yosh shares his guiding principle of “finding the friend in the room” to drive systemic change.
35:19 Lionel explains how a LinkedIn post about 529s led to discovering Hadley and connecting with Yosh
37:20 A specific example of how Lionel uses 529s
40:40 Recent policy changes allowing 529 funds to roll into Roth IRAs
42:00 The gift that keeps giving: expansions of 529 benefits across multiple federal administrations
42:40 Early investor skepticism of Hadley