Ever wondered how to date a rich man? In this episode, two successful (and brutally honest) millionaires, Jordan and Chris, spill exactly what high-value men look for in a woman. From gold-digger red flags to first-date dealbreakers, they reveal how to attract—and keep—a wealthy guy. We also dive into their worst dating experiences, love languages, and what makes a woman truly unforgettable. If you want the blueprint to bagging a rich man, this one’s for you.
What do successful entrepreneurs really look for in an employee? In this week’s Fourthwall segment, three business-savvy men—Chris, Jordan, and Wootak—share what stands out to them when hiring and what traits employers actually value. Then we jump into Dollar Store Therapy, where you ask the questions and we give you the raw, unfiltered advice—from growing a small family business to dealing with an emotionally distant sibling.
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Timestamp (ep. 15)
0:00 - Intro
1:26 - How did Chris start his first business
3:42 - How to bag a rich guy and what to expect
15:40 - Clingy girls
17:54 - Why you should only date 1 person at a time
21:44 - Wear your intentions on your sleeve
22:58 - Jordan thought he had to lie to girls
29:41 - What type of rich man should you go for?
30:24 - When is it the right time to have children?
36:48 - What made Chris and Jordan want to be with their GF
38:07 - Has a girl ever finessed Chris/Jordan for money
40:17 - What is your love language?
45:36 - What rich people buy their GF
47:26 - How to leave someone better than you found them
52:03 - 3 most obvious gold digging behaviors
54:12 - Top 5 red flags on a date that rich men care about
58:22 - w1tchh craft
1:00:47 - 5 qualities that stand out in a girl
1:06:32 - Worst date stories
1:13:13 - Esther has been a bad date
1:15:52 - Super Bonsai
1:16:31 - Fourthwall
Follow Esther
Instagram: https://www.instagram.com/littlebunszz/
TikTok: https://www.tiktok.com/@littlebunszz
YouTube: https://www.youtube.com/@Littlebunszz
Follow Wootak
TikTok: https://www.tiktok.com/@barchemistry
Personal TikTok: https://www.tiktok.com/@superbonsaihealth
Instagram: https://instagram.com/barchemistry
Personal IG: https://www.instagram.com/wootak
YouTube: https://youtube.com/channel/UCDfX41sMJRIeG8kqAGTz6mg
Follow Jordan
Instagram: https://www.instagram.com/medinger/
TikTok: https://www.tiktok.com/@jordanmedinger
Follow Chris
Instagram: @Chrixchr
#podcastersofinstagram #abovetheinfluence #undertheinfluence
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