Other People's Pockets – Details, episodes & analysis

Today I’m interviewing someone who helps me immensely with my work, the way I approach my career, and how to just be more effective and intentional with my time.

I’m talking to my executive coach, Taylor Winters, because she has some really interesting ideas about the concept of “enough,” which we talk about a lot on this show.

This episode is a Pocket Dial! That's where we pause to reflect on the money themes that come up on Other People's Pockets.

Taylor Winters is an executive coach and entrepreneur. She co-founded and managed a globally-recognized design agency to a successful exit and pivoted her focus from developing products to developing people, specifically leadership professionals across industries. She earned her coaching certification from UC Berkeley (Haas) created the leadership practice Every Day Future, and is pursuing a Masters in Applied IO Psychology from Harvard.

Follow Taylor Winters:

IG: @everydayfuture

Follow Maya Lau:

IG: @itsmayamoney

LinkedIn: @mayalau

TikTok @itsmayamoney

YouTube: @itsmayamoney

Today I’m bringing you my interview with Cecilia Thiam, a 35-year-old Swiss-American humanitarian aid worker who has spent most of her career living and working in sub-saharan Africa. She lost her job after the Trump administration enacted sweeping cuts to the United States Agency for International Development (USAID). Now, she has had to scrap her plans, move to a new country with her 6-year-old daughter while parenting solo, and re-think her entire career.

We spoke on July 10, 2025.

This is part of a theme we are pursuing looking at how the Trump administration is affecting people’s personal finances. If you know someone who would be a great guest, get in touch at otherpeoplespockets@gmail.com or on Instagram or TikTok at @itsmayamoney. And on LinkedIn!

Thank you for supporting this show!

Ismatu Gwendolyn is a mental health professional and life coach who is trying to rethink how we care for those in need. Ismatu has navigated sex work in order to afford life and graduate school, and they discovered that as a stripper, talking to men in a club was not so different than counseling a client as a therapist. Ismatu let us have a peek inside their personal finances to find out how this all comes together.

Follow Ismatu:

TikTok: @ismatu.gwendolyn 

Instagram: @ismatu.gwendolyn

Follow Maya Lau at:

X: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

It's time for another Pocket Dial! That's where we pause to reflect on the money themes coming up on Other People's Pockets. Jared Ball is a professor of Communications and Africana Studies at Morgan State University in Baltimore and the author of "The Myth and Propaganda of Black Buying Power." He helps unpack the lies around "passion work" and why it feels like you have to be out for yourself when it comes to finances.

Follow Jared at:

Instagram: @imixwhatilike

X: @imixwhatilike

Follow Maya Lau at:

X: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

What is this whole "financial-freedom-through-real-estate-investing" thing people are doing, and is it real? Maya interviews Deandra McDonald, a real estate investor and influencer with 320k+ followers on her TikTok, @simplerealestate. Deandra says she became financially free at 28 after five years of house-hacking (buy a property, rent part of it, live in the other part, and have your tenant pay your mortgage!). Deandra only found her path after several life choices went wrong for her in her early twenties. Now she uses her experience (and fun personality) to teach others her real estate ways. 

Follow Deandra:

TikTok: @simplerealestate

Instagram: @deandramcdonald

https://www.deandramcdonald.com/

Follow Maya Lau at:

X: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

Have you ever thought about how money feels in your body? Or how sticking with a budget might start with healing your money wounds first? Today Maya interviews Bari Tessler, a financial therapist and author of "The Art of Money: A Life-Changing Guide to Financial Happiness." Bari explores what it feels like to even hear the truth about other people's money stories, and how to navigate our own.

Follow Bari Tessler at:

baritessler.com

Instagram: @baritessler

X: @baritessler

Follow Maya Lau at:

X: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

Today Maya interviews a couple we're calling D+A, because they wanted anonymity so they could discuss their finances openly. D+A are in love, engaged and have been living together for about a decade, but financially? They're just roommates. Separate bank accounts. Separate credit cards. One of them will ask the other to Venmo them $7 after a Target run. Why? Maya digs into their money pasts and fears and gets them to fact-check each other in real time.

Follow Maya Lau at:

Twitter: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

Kyle Coon is a blind Paralympian triathlete on Team USA. Kyle was diagnosed with eye cancer at 10 months old and had his eyes removed at age 6. His blindness didn’t stop him from becoming a competitive rock climber, downhill skier, runner and triathlete. He revealed how personal finance is different as a blind person, and what it means to rest almost all your financial hopes on winning a medal in the Paralympic Games in Paris 2024.

Follow Kyle:

Instagram: @eyeronkyle

Follow Maya Lau at:

Twitter: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

A few weeks ago, I had the cockamamie idea to fly to Shreveport, Louisiana. I wanted to visit a weed doctor, get a medical marijuana prescription, and then smoke weed and interview her while high. And that is exactly what I did! Jaya McSharma is a medical doctor and the co-owner of CannaCare of Louisiana, a medical marijuana clinic. Jaya is also an actress and filmmaker and has some wild stories about getting Bernie Madoff’ed out of basically her entire life savings.

Follow Jaya:

Instagram: @jayamcsharma

https://cannacarela.com/

Follow Maya Lau at:

Twitter: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney

How does money mix with religion? Blair Pogue is a church leader who works for the bishop of the Episcopal Church in Minnesota. She's a longtime former priest at St. Matthew’s Episcopal Church in St. Paul, where she helped manage the church's finances and encouraged people to give 10% or more of their income. She shares how much she's paid and whether it's enough — and how she tracked how much money each of her parishioners put in the offering plate.

Follow Maya Lau at:

Twitter: @mayalau

Instagram: @itsmayamoney

TikTok: @itsmayamoney