26. Rick Ross on Hustlin', Going Broke to Get Rich & Set in Stone | PYF$ with Cipha Sounds

26. Rick Ross on Hustlin', Going Broke to Get Rich & Set in Stone | PYF$ with Cipha Sounds

Cipha Sounds sits down with Rick Ross to celebrate 20 years of Port of Miami and the new album Set in Stone. They get into how "Hustlin'" broke on Hot 97, why you've got to go broke a few times to become a real boss, old Miami, and Ciph's ongoing campaign to get Ross to franchise him a Wingstop. Set in Stone is out now.

25. Funny Makes You Better Looking | Rob Haze | PYF$ with Cipha Sounds

Comedian Rob Haze (Atlanta-raised, LA-based) pulls up to the studio and Ciph breaks out the Trump umbrella he jacked 15 years before anybody thought Trump could be president. They get into riders and the mythology of one-time Air Force Ones, why funny makes you better looking, Jamaican patois and dancehall's problematic hits, the masked white nationalists on the DC bus, doxing, Mamdani's first months, the Knicks' championship afterglow, Alvarado's Brooklyn energy, and the time Ciph sang a song he didn't understand to a waitress in Charlotte. Serious things, the silly way. How have you helped a friend today?

24. Why This Is the Best Summer of Your Life | Ian Lara | PYF$ with Cipha Sounds

Comedian Ian Lara joins Cipha Sounds and Rocky Powell for the first LIVE episode of PAY YOUR FRIEND$. They get into the Knicks championship run, why old-school NYC energy is back, jazz clubs, dead nightlife, and why Summer 2026 might be the best one yet — plus Ian's confession that he hates all animals.

23. How Caribbean Culture Built London & NYC Hip-Hop | DJ Snips | PYF$ with Cipha Sounds

Cipha Sounds sits down with London-born, NYC-based DJ and producer Snips (aka Todd Worsnip — founder of Barbershop Records and Livin' Proof) for a deep dive into UK music and how it really connects to New York. Ciph has been championing UK and Caribbean sounds since 1999, and the two of them get into why it never quite breaks through in the States — plus the Jamaica-to-London-to-Brooklyn pipeline that built so much of what we call hip-hop. With Rocky in the room taking guesses, it goes everywhere.

22. SQUASHING BEEF WITH NATHAN & REGGIE | PYF$

On this episode of the "Pay Your Friends" show, host Cipha Sounds brings old and new friends together for an energetic discussion on the many faces of anger. Comedians Nathan Macintosh and Reggie join Cipha to recount their past "on-sight" beef from 2014 and debate everything from the current state of hip-hop and R&B to the frustrations of airline food. Whether they are analyzing viral plane confrontations or discussing why some people just can't get a birthday invite, the trio dives deep into what makes them "crash out."