Comedian Gary Owen sits down with Jerome D. Love on the Black Money Tree Podcast to unpack the business of comedy—from door deals vs. guarantees and the real cost of shooting a stand-up special, to social media strategy, cancel-culture, and how clips drive ticket sales. Gary also opens up about growing up poor, money habits, the Mo’Nique/Will Packer controversy, being left off the Think Like a Man poster, life after divorce, and why he’s investing in real estate while touring. If you’ve ever wondered how comedians really get paid—or how to turn laughs into long-term wealth—this episode is a masterclass.

What you’ll learn

How stand-up comics make money (guarantees, door deals, bonuses, and routing)

The true cost to film a comedy special—and when to own vs. license it

Why YouTube first releases can beat traditional networks

Gary’s money mindset: from trailer park to headliner, saving, and “broke habits” to keep

Cancel-culture, crowd phones, and why live shows are still a free-speech safe zone

Real estate plays (flips, permits, partnerships) and building post-tour income

Fatherhood, divorce lessons, and setting expectations in relationships & careers

#GaryOwen #BlackMoneyTree #StandUpComedy #ComedyBusiness #HowComediansGetPaid #DoorDeals #ComedyClubs #ContentStrategy #CancelCulture #RealEstateInvesting #WealthBuilding #Entrepreneurship #MoNique #WillPacker #ThinkLikeAMan

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Chapters
0:00 Cold open – comedy teaser
1:27 Show intro & theme
2:01 Why Gary moved to Houston (taxes + travel)
4:09 H-Town staples + DJ Screw “June 27th”
5:12 Sponsor: The Collective
6:25 Stage persona vs real life
7:38 The Black Church bit — origin & rise
10:40 Growing up broke → money mindset
12:49 Fear of going broke; saving & first jobs
19:03 Feeling at home in Black spaces
22:55 Mo’Nique vs Will Packer explained
26:05 Cancel culture & phones vs live shows
27:54 Image, frugality & first-date economics
32:12 Crustaceans story & “no Plan B” focus
36:05 From Navy/Comic View to today’s stand-up economy
39:37 Stand-up vs sketch content
41:51 How comedians get paid (guarantees vs door deals)
50:25 Left off the Think Like a Man poster
53:19 What a stand-up special really costs
55:22 Two specials in one weekend (+ non-race hour)
59:04 Own it or YouTube it? Distribution strategy
1:01:54 Divorce & money freeze; rebuilding
1:03:36 Real estate plays (flips, partners, permits)
1:08:39 Parenting on tour → twins & values
1:15:06 What still excites Gary + new TV idea
1:17:53 If starting over & if 20 today
1:21:55 Closing & tour link
The Collective
https://www.communitycollectivehouston.org/

Speaking Engagements
https://jeromedlove.com/

Personal Coaching
https://consulting.theblackmoneytree.com/sales-page1649477479505
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Closing the Wealth Gap: How to Build Wealth in Black Communities by Investing in Rea Estate

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About The Black Money Tree
NAACP Image Award-winning Podcast spearheading a movement dedicated to transforming communities through real estate investment and entrepreneurial ventures. Together, we’re bridging the wealth gap, fostering self-sustainability, and leaving a legacy of prosperity for generations to come. Tune in to cultivate financial literacy, explore wealth-building strategies, and be inspired to plant seeds of economic empowerment. Let’s grow our collective economic power and cultivate a brighter future for all.

Our Team

Jerome D. Love, Creator and Host
Misty Starks, Producer
Jonathan Omoyeni, Director of Photography

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