On Episode 42 of Rich Lessons, Sevetri Wilson Taylor (Instagram.com/sevetriwilson) and Sheena Allen(Instagram.com/whoisSheena) sit down with real estate investor, developer, and agent Chris Ross, whose path into commercial real estate began behind a bar on Bourbon Street and led to multi–million–dollar hospitality and mixed-use deals.

Chris shares how he went from making $800 on his first $45K deal to brokering $30M+ transactions, and why he believes now is still a powerful moment to move into commercial real estate, especially as others run away from office buildings and underperforming assets. He breaks down how to leverage equity, recognize the subtle signs of opportunity (like worn pool furniture and empty elevators), and think beyond single-family rentals into hotels, large residential properties, and creative adaptive reuse.

The conversation also dives into real estate as a reflection of culture—from office-to-residential conversions and content studios to the rise of Airbnb-style hospitality. Chris explains how he utilizes AI and ChatGPT daily in his brokerage work, without compromising the human element that actually closes deals. And in his Rich Lesson, he brings it all back to one core principle: relationships are the real asset in business and in building long-term wealth.

Show Notes:

(00:00) Intro — Meet Chris Ross: Bourbon Street bartender turned commercial real estate dealmaker

(01:07) From phone book to first license — breaking into real estate without a “traditional” background

(02:47) Leaving residential behind — the persistence that opened CRE doors

(03:43) What most people don’t know about commercial real estate: leveraging equity and financing million-dollar deals

(05:02) “Blood in the water” — short sales, distressed assets, and why Chris thinks now is still a good time for CRE

(06:15) How he turned bad pool furniture and empty elevators into a $35M transaction

(08:19) The $45K building and an $800 commission — why you can’t start at $30M deals

(09:49) Balancing culture, preservation, and profit in New Orleans while bringing more Black entrepreneurs into big deals

(12:02) Where to start in hospitality and commercial: valuation, learning from the bottom up, and knowing your investing style

(21:08) How Chris uses AI and ChatGPT daily in real estate (and why relationships still matter more than ever)

(29:26) Real estate follows culture — office conversions, content studios, data centers, and shifting demand

(33:00) Airbnb vs hotels — pros, cons, profitability, and why consistency still sells

(39:29) Rich Lesson — relationships, credit unions, and why your network is your true leverage

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Rich Lessons Podcast // hosted by Sevetri Wilson Taylor and Sheena Allen

• Subscribe to Rich Lessons on Apple Podcasts (https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124) and Spotify (https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl)

• Watch and subscribe to Rich Lessons on YouTube (https://www.youtube.com/@richlessonspodcast)

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On Episode 41 of Rich Lessons, Sevetri Wilson Taylor (Instagram.com/sevetriwilson) and Sheena Allen(Instagram.com/whoisSheena) talk with Karen Freeman-Wilson, former Indiana Attorney General, the first Black woman mayor of Gary, Indiana, and now President & CEO of the Chicago Urban League.

Karen opens up about growing up in Gary’s industrial heyday, witnessing its economic collapse, and leading through a $26 million budget loss on her first day as mayor. She breaks down the realities of running a predominantly Black city, confronting systemic bias, and rebuilding trust between citizens and government.

From redirecting Indiana’s tobacco settlement funds entirely to health initiatives to reshaping Chicago’s community narrative, Karen shares how leadership grounded in empathy and accountability can change outcomes. The conversation dives into today’s political climate, the quiet rollback of DEI, and her warning against what she calls “legislative genocide.”

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Show Notes:

(00:00) Intro & welcome

(01:18) Mini bio & firsts (AG; first Black woman mayor; now CUL CEO)

(02:47) Gary’s boom → decline snapshot

(04:44) Bias toward Black-majority cities explained

(07:12) Day-one $26M budget hit; “expect more” leadership

(11:06) AG wins: nursing homes reform; 100% tobacco funds → health

(14:17) Harvard story: grit & “finish what you start”

(18:30) Loss → Chicago Urban League; narrative + cross-sector work

(22:49) “Show up twice”: block + boardroom approach

(25:32) Today’s climate: values, DEI retreat, bill impacts (SNAP, schools, health, environment)

(33:19) Nonprofit response; job fair surge (3K in-person / 5K online)

(41:01) Rich Lesson: treat people how you want to be treated

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Rich Lessons Podcast // hosted by Sevetri Wilson Taylor and Sheena Allen

• Subscribe to Rich Lessons on Apple Podcasts (https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124) and Spotify (https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl)

• Watch and subscribe to Rich Lessons on YouTube (https://www.youtube.com/@richlessonspodcast)

• Follow Rich Lessons on Instagram (https://www.instagram.com/richlessonspodcast/) and TikTok (https://www.tiktok.com/@richlessonspodcast)

On Episode 40 of Rich Lessons, Sevetri Wilson Taylor (Instagram.com/sevetriwilson) and Sheena Allen(Instagram.com/whoisSheena) sit down with Takema Robinson, executive producer of Netflix’s top-streaming documentary The Perfect Neighbor, to talk about justice, storytelling, and the movement behind one of the most powerful films of the year.

Takema, an activist, producer, and founder of Standing in the Gap Fund, shares how a Freedom of Information Act (FOIA) request turned into a #1 Netflix film and a catalyst for change in the wake of AJ Owens’ killing. She opens up about transforming hours of police body-cam footage into a gripping, artful story that sparked national conversations on race, justice, and “Stand Your Ground” laws.

From advocacy to art, Takema breaks down the emotional journey of turning grief into purpose, the importance of storytelling as a tool for healing, and the power of keeping a promise—ensuring the world will always know AJ Owens’ name.

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Show Notes:

(00:00) Intro — Meet Takema Robinson, executive producer of The Perfect Neighbor

(02:30) Movement in Her DNA — Growing up in New Haven’s Black Power era

(04:15) From Howard to Healing — Studying art, politics, and culture as tools for justice

(06:10) The First Film — How advocacy led her to documentary storytelling

(07:18) FOIA to Film — Using public records to uncover AJ Owens’ story

(11:18) The Perfect Neighbor — Inside the footage, the verdict, and the emotional response

(14:30) Mobilizing for Justice — The call at dawn and activating national support

(22:16) The Power of Truth — Staying inside body-cam footage and trusting the audience

(25:06) Beyond “Trauma Porn” — Why this film is activism, not exploitation

(33:33) The Children — Healing, therapy, and the legacy AJ left behind

(41:01) The Aftermath — #1 on Netflix, a national impact tour, and Standing in the Gap Fund

(45:13) Rich Lesson — Purpose is the bridge between pain and power

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Rich Lessons Podcast // hosted by Sevetri Wilson Taylor and Sheena Allen

• Subscribe to Rich Lessons on Apple Podcasts (https://podcasts.apple.com/us/podcast/rich-lessons/id1787798124) and Spotify (https://open.spotify.com/show/40jGSUvVrMbxKcJ1ghE8kl)

• Watch and subscribe to Rich Lessons on YouTube (https://www.youtube.com/@richlessonspodcast)

• Follow Rich Lessons on Instagram (https://www.instagram.com/richlessonspodcast/) and TikTok (https://www.tiktok.com/@richlessonspodcast)