S4E57 - Chris "DJ O" Obando of SCE on Timing, Burnout & Saying Yes When It Actually Matters

Have you ever been in that phase where you’re doing the responsible thing, but also building something on the side, and both are starting to fight each other. One is paying your bills, the other one is quietly telling you this is the thing, and you don’t know when to pull the trigger.That’s this episode.We had Chris "DJ O" Obando on, and before we got into anything useful, we spent a solid chunk of time talking about me destroying my own car with a sponge, Rolando curbing brand new wheels mid-OCD spiral, and whether Ben should bring back a 20-year-old baggy suit. So very on brand.But underneath all that, there’s a real conversation about timing. When do you actually make the jump. What if you’re not ready. What if you wait too long. And the part nobody talks about, that middle phase where you’re grinding both sides and hoping it makes sense eventually.Also, we made a spring Old Fashioned with bourbon, honey, lemon, and bitters. Thought it was his drink. It wasn’t. He drank it anyway. That’s how you know he’s a pro.