Kate Mereand founded and ran the Office of Innovation and Equitable Development within Washington, DC’s local government. Over 10 years, she estimates her team worked with 20,000 current and would-be entrepreneurs–people who pursued business ownership to provide a service for their community, because they faced limited employment opportunities, and also because they had an idea they just had to see all the way through.

But many of these brave, determined people–even when they grew sizable enterprises–kept hitting emotional and psychological walls that Kate came to realize had to do with trauma–trauma around money.

Episode Guide

2:40 Kate’s money origin story growing up on a dairy farm

10:53 Founding the Office of Innovation and Equitable Development. Some entrepreneurs were focused on the dream, not the money-management necessary to facilitate it.

15:20 Creating a training around money and trauma

25:52 What do you tell a devoted entrepreneur whose idea you think might not stand a chance?

27:26 Kate confronts her own money trauma

32:27 Kate and Lionel talk about what they like spending money on

37:40 Detangling money and worth

Sameer Sood is a medical doctor who is sick of the many financial limitations he’s had to confront. For example, if a patient is covered by Medicare or Medicaid, why can’t that pot of money also cover housing, which might be the best, most cost-effective prescription he could write for someone without shelter? And why can’t you use some of the finance tools of for-profit startups to fund not-for-profit, community-based work? That’s what Sameer is asking–and answering–with the company he cofounded, FwdSlash.

Sameer grew up with relatively little money and even after earning a doctor’s salary never seemed to become too attached to any of it. Of all the things he’s done so far, that may be what's most impressive.

Episode Guide

1:53 Sameer’s money origin story

6:20 A physician’s view of what’s wrong with healthcare in America

8:45 He’s a doctor and an entrepreneur and doesn’t see a difference between the two.

10:55 Feeling “bullet-proof” on $60,000 per year

13:12 Helping non-profit organizations use finance tools typically reserved for for-profits

23:59 What he really wants to buy is his time

28:27 Nine-year-old Sameer wages a schoolwide campaign to buy his family a TV

33:13 Lionel confesses his money envy

Private foundations are tax-exempt entities that serve a charitable purpose. In the US, they have about $1.5 trillion in assets under management. How much, you may wonder, are they required to spend on mission-driven activities each year?

Five percent.

Which is why my friend and guest Rodney Foxworth is helping these organizations think through the other 95% and whether that part of their operations will look like every other profit-maximizing pool of money around the world or something that also supports their charitable mission.

Episode Guide

1:37 Rodney's birthday celebrations used to be known across several states.

2:53 His name sounds a little too on the nose.

4:13 Rodney's money origin story

9:50 How his firm Worthmore helps foundations, family offices, and mission-driven investors

14:28 Why these wealthy organizations need social impact advisors

18:52 The scale of the social impact industry

20:09 A generational shift driving wealthy people and organizations to better align their values and their investing

22:50 Does investing more in your mission inevitably mean making less money?

33:06 A creative example of a foundation redirecting its financial returns to low-income program participants

Elizabeth Evitts Dickinson is the author of the new biography “Claire McCardell: The Designer Who Set Women Free.” Published on June 17, the book, Dickinson's first, has been praised in the New York Times, Bazaar, Elle, and other publications. Surely wealth and the high life are just around the corner, right?

Tiffany Ferguson is fearless. On a regular basis, she voluntarily does two things that can be tough. First, she has intentional, personally revealing conversations about money, and second, she does this with multiple members of her extended family. Money, family, feelings. Individually, each of these things keeps therapists in business. But Tiffany makes a compelling case for why we all should consider having these conversations and teaches us how to do it.

Eric Leslie grew up with a big pile of money. That money gave him a boost, but it also cast a shadow over generations of his family. Today he’s a nonprofit leader demonstrating how we can leverage financial resources and a different kind of currency to make families and communities stronger.

My name is Lionel. I feel a real need to talk about money. And I think you should too.