In this episode, Roscoe flips the script and puts Jared in the guest seat for the first time, joined by Dane Illif, Jared's longtime co-founder and right-hand man at The Kitchen. Together, they trace the full origin story — from a broke music startup in Oakland to building the brand that helped define modern pickleball culture.
Jared opens up about the winding road that led him to Austin: surviving 9/11 in New York, playing in a funk band called Frontline Theory, running a nonprofit in San Francisco, and finally landing at a digital agency where he realized he was unemployable and couldn't work on someone else's dream. The Kitchen didn't start as a business plan — it started as a Facebook group for Austin pickleball players during COVID, born out of a failed music company and a chance invite to play at a bar called Bolden Acres.
Jared and Dane also get into the behind-the-scenes of how The Kitchen actually became a business — from a $1,000/month deal with an Amazon paddle brand, to producing an $8,000 Electrum commercial in Vegas, to landing an early partnership with Connor Pardus and the PPA before anyone else believed in them. They break down why they never bought a single follower, what made the kitchen impossible to replicate, and why Jared believes singles pickleball is the format that takes the sport to TV.
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Timestamps:
1:09 — Jared in the Hot Seat
2:17 — Dane Joins the Story
4:29 — The Broke Oakland Music Startup
9:38 — Growing Up & Early Life in Atlanta
10:10 — Bombing the Interview, Then Getting the Job
12:34 — Seeing 9/11 from NYC Rooftop
14:19 — Playing in a Band Called Frontline Theory
16:07 — Quitting Sales & The Power of Now
17:18 — Building a Nonprofit in San Francisco
19:29 — Working at Salesforce & a Digital Agency
21:06 — Why the Early Companies Failed
22:18 — Community First vs. Product First
27:08 — How Pickleball Found Them During COVID
28:02 — The Kitchen Is Born
29:07 — Dane Create the Logo
32:23 — When It Became a Real Business
34:03 — Trying to Make a Pickleball (and Failing)
36:28 — The $8K Electrum Commercial in Vegas
38:21 — The Early PPA Partnership
39:44 — The Kitchen by the Numbers Today
43:51 — Never Buying a Single Follower
45:14 — Top Tips for Creators
48:10 — Most Viral Post of All Time
49:24 — Is the Pickleball Boom Over?
50:44 — Favorite Pickleball Events
54:24 — What Pickleball Has Given Them
57:33 — The Future of Pickleball & The Kitchen
