Starting a business looks glamorous from the outside—but the reality is messy, hilarious, and full of lessons you don’t learn in school.

In this episode, Rachel and Josh from Pinpointe Group sit down with Taylor Ouellette and Jordan Winston, co-founders of Not Your Dad’s Media, to compare notes on the real founder struggles: bad clients, co-founder dynamics, launching before you’re “ready,” and protecting culture at all costs.

Whether you’re in real estate, marketing, or just thinking about starting something of your own, this conversation is a raw look at what it really takes to build and survive as a founder.