Episode Description
In this raw, unfiltered conversation, Pimpin Ken, a former high-level pimp from Chicago and Milwaukee, breaks down the psychology, power dynamics, and realities of the pimping game during its peak in the 1970s–1990s.
Ken speaks candidly about how he entered the life as a teenager, the culture of pimping that existed at the time, and how manipulation, control, and desensitization became central to survival. He explains the difference between street-level track work and higher-end strip club and VIP hustles, detailing how money was really made — and why most people misunderstand the game entirely.
This interview also dives deep into:
-The psychology behind control, power, and influence
-How pimping was normalized in certain eras and communities
-The role of trauma, abandonment, and emotional conditioning
-Why he avoided violence and relied on manipulation instead
-The evolution from street hustling to sophisticated financial setups
-His thoughts on relationships, marriage, masculinity, and power
-How prison, reading, and reflection changed his perspective
This is not a glamorization — it’s a firsthand account of a brutal system, told by someone who lived it and survived it.
Support Ken
Audio Book: https://www.audible.com/pd/Pimpology-Audiobook/B0196WKYU8?source_code=ASSGB149080119000H&share_location=pdp
Hip Hop Fraternity: https://www.pimpinken.net/
This Episode Is #Sponsored By The Following:
The Wellness Company! Power up with RECHARGE! Click https://twc.health/connect and use code CONNECT for 10% Off + Free Shipping on every order 🇺🇸.
Rocket Money! Let Rocket Money help you reach your financial goals faster. Join at https://rocketmoney.com/connect
Cash App! Download Cash App Today: https://capl.onelink.me/vFut/ #CashAppPod. Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. See terms and conditions at https://cash.app/legal/us/en-us/card-agreement. Cash App Green, overdraft coverage, borrow, cash back offers and promotions provided by Cash App, a Block, Inc. brand. Visit http://cash.app/legal/podcast for full disclosures.
Join The Patreon For Bonus Content!
https://www.patreon.com/theconnectshow
00:00 Introducing Pimping Ken & His Legacy
02:18 Origins: Hustling in Chicago
06:01 Juvenile Crime & Early Lessons
09:08 Transition to Milwaukee & First Schemes
13:16 Entering the Pimp Game
16:46 The Milwaukee Pimping Culture
20:25 Psychological of Pimping
21:24 This Episode Is Sponsored By The Wellness Company
22:58 Breaking Tricks – The Strip Club Game
28:39 How Pimping & Payments Really Work
33:01 Scaling Up: From Pimping to Business
38:42 Managing Multiple Women
39:48 Manage YOUR Money With Rocket Money
41:27 Pimping, Power & Mind Games
49:54 This Episode Is Sponsored By Cash App
51:22 From The Streets to Legendary Status
56:15 Trauma, Environment & Why People Pimp
01:02:03 Book Deals, Rap Fame & Legal Hustle
01:10:54 Major Deals, Royalties & Real Business
01:17:41 Education, Self-Help & Writing Approach
01:26:01 Life After Pimping – Giving Back
01:32:31 Fatherhood, Relationships & Change
01:38:46 Financial Success: Pimp Game vs. Legal Life
01:44:00 Stepping Into Mainstream Business & Media
01:48:02 Building the Hip-Hop Fraternity & Future Plans
01:50:02 Final Reflections & Where to Find Ken
Learn more about your ad choices. Visit podcastchoices.com/adchoices