How Taking a Chance Built Not Your Dad's Media
Starting a business rarely unfolds like the smooth stories we often hear. For Jordan Winston, launching Not Your Dad's Media was part circumstance and part deliberate risk. But beyond the business itself, it’s the embodiment of a long-held drive to create and shake up digital storytelling.
Not Your Dad's Media is still just finding its footing, only a few months old, and it already feels different from the usual startup playbook. Jordan and his team leverage personal branding and social media in a fresh way, aiming to help founders turn their authentic stories into real revenue. "We make content for founders that doesn't suck," he jokes, highlighting how often business narratives miss the human touch.
This venture came together quickly, sparked by a LinkedIn message and a shared vision between Jordan and Taylor, his co-founder. They clicked over the belief that founder-led content can elevate brands and businesses in ways traditional marketing misses.
Jordan’s path here wasn’t a straight line. He’s worn many hats, from real estate to bartending to surf lessons. Each experience added a piece to his entrepreneurial toolkit. Before this, he ran Pink's, a cleaning company that he still oversees strategically. But a turning point came when Samsara, a tech company where he held a sales role, let him go. Suddenly, the safety net was gone, pushing him to bet fully on his own ventures.
He reflects on what fuels him: "Building companies is addictive. The rush of seeing an idea come alive and then actually bring in money feels like a different kind of success."
Jordan is no stranger to the challenges entrepreneurship brings. Early on, his bank balance shuffled dramatically, a financial rollercoaster he accepts as part of learning. Free from real-world pressures like family or mortgages, he acknowledges his privilege in being able to take risks now and focus without compromise.
His message to other entrepreneurs is simple: keep your risks manageable. Start something on the side, hold onto a job you can lean on, and don’t let being broke stall your creativity. "Stress over rent doesn’t help anyone build something meaningful," he says candidly from personal experience.
With ambitions to grow Not Your Dad's Media into a media company that stands apart, Jordan uses LinkedIn as a key growth tool. His eye’s set on hitting $100,000 in monthly recurring revenue (and you can bet we're rooting for him to make it happen).
Jordan’s story is about embracing uncertainty and doing it all for the right reasons. "You really have no risk," he says, a reminder that sometimes the biggest leaps come with the most potential. One thing's for sure, no matter how hard it gets, or what's coming his way on the road to 100k MRR, Jordan's ready.
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