Surviving Prison, Losing Friends & Starting Over – Khalif Kairo | Midnight Coffee Run (E009)

Konichiwa Fam, Welcome back to another episode of Midnight Coffee Run. I'm joined by Khalif Kairo, the founder of Jetman Global and Kai and Karo car dealership. In this episode, Kairo opens up about his time in prison and the harsh realities that came with it. He shares the origins of his struggles, his views on the storm that be-fell him, and the journey of scaling his business despite the odds. We also dive into his flying career, the vision behind JetMan Global, and his eye-opening experiences in Japan, Jamaica, and Singapore. This episode is packed with raw insights, inspiration, and unexpected moments. As always, thank you for the continued support. Hope you enjoy this one. Team Coffee Pump. Find Kairo: X: https://x.com/KhalifKairo Instagram:   / khalifkairo   CoffeePump Socials: Instagram:   / coffeepumppodcast   utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw== Coffee Pump Audio: Apple Podcast: https://podcasts.apple.com/ke/podcast... Spotify: https://open.spotify.com/show/0X1unCg... Find our host Sajid Vayani: Instagram: https://instagram.com/sajidvayani?igs... TikTok: https://www.tiktok.com/@sajvayani?_t=... YouTube:    / @sajidvayani   Twitter / X: https://x.com/sajvayani?s=21 Disclaimer: The content of The Coffee Pump Podcast is intended for entertainment and informational purposes only. The views, thoughts, and opinions expressed by the hosts and guests are solely their own and do not necessarily reflect the views of The Coffee Pump Podcast, its affiliates, or any associated entities. Nothing discussed in this podcast should be construed as professional advice in any field, including but not limited to legal, financial, medical, or business matters. Any statements made about businesses, products, or individuals are based on personal experiences and opinions and are not meant to be taken as fact or a definitive review. The Coffee Pump Podcast does not assume any liability for the accuracy, completeness, or consequences of using the information discussed. Listeners are encouraged to form their own opinions, conduct their own research, and seek professional guidance where appropriate. By listening to this podcast, you acknowledge that The Coffee Pump Podcast is not responsible for any actions or decisions made based on the content provided. 0:00 - Intro 1:00 - Kairo's experience in prison 16:13 - Fair- weather friends 19:02 - Business challenges while in prison 24:24 - Genesis of Kairo's problems 30:01 - Glorifying politicians 36:25 - Scaling up the business 38:30 - Plane's discussion 43:16 - Kairo's flying career 46:40 - Kairo's dream for jetMan global 48:23 - Kairo's Japan experience 58:22 - Kairo's love for Jamaica 1:00:00 - Singapore experience 1:03:20 - 5 car garage 1:06:00 - Fatherhood 1:11:20 - US gun culture 1:12:09 - Business class experience 1:12:53 - Air TZ vs KQ 1:14:50 - Sajid's ex 1:16:06 - Outro