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 Books: https://www.lulu.com/spotlight/PimpinKen7?srsltid=AfmBOoocrftoIFbUynb_2YpRlVnI7TyfLbkZk6L55Hq6d821w17fi1K5 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 Spotify: https://open.spotify.com/show/6mc4qAxpztC6D20wzeS91C Join this channel to get access to perks: https://www.youtube.com/channel/UCU69IWUT8m_qPT01AbelXiA/join