#13: What does running 100 miles, biking across the country, and a four-foot wall calendar have in common? They're all part of how Taylor Prokes, Co-Founder and CEO of Big Ass Calendar, lives — and plans — a full life.
In this episode of VDEOMKR, recorded live at SXSW in Austin, Texas, Carly sits down with Taylor for one of the most energizing, honest, and genuinely fun conversations we've had on this show. Taylor is the co-founder of the Big Ass Calendar — the bold, oversized planning tool and mindset system built around the philosophy that the best moments in your life aren't stumbled upon, they're scheduled. She's also recently stepped into the CEO role at 100 Mile Group, overseeing multiple brands, partnerships, and product growth.
But Taylor isn't just talking planning theory — she's done the 100-mile race. She's run rim-to-rim-to-rim in the Grand Canyon. She quit corporate finance, lived out of her Jeep, taught herself content creation, and cold-emailed her way into Jesse Itzler's orbit before eventually co-founding one of the most talked-about analog products in a digital-obsessed world.
This one goes deep on the mindset behind intentional living, building community as an adult, the intersection of physical challenges and creative confidence, and what it actually looks like to build a product-based business from the ground up.
In This Episode, We Cover:
- The origin story of Big Ass Calendar — from a folded piece of paper in a coaching box to a four-foot dry-erase wall system
- The 1-6-4 Method: one year-defining event, six mini adventures, four winning habits
- Why planning more actually makes you more spontaneous — not less
- How to handle life derailing your goals (and why shifting priorities isn't failure)
- Taylor's journey from corporate finance → California Closets → Jeep life → CEO
- Running a 100-mile race and what extreme physical challenges teach you about creative confidence
- Building community intentionally as an adult in a new city (and her 24-hour follow-up rule)
- Navigating scammers and counterfeit products as a growing e-commerce brand
- Why authenticity in content — even the gnarly, unglamorous stuff — is the most powerful marketing tool
- What it means to build your life resume, not just your work one
- Her advice to any creator who's too scared to put their work out there: start when you're bad
This episode is for MKRS that are ready to stop waiting for the right time and start putting the right things on the calendar.
To watch the show click HERE
To connect with Taylor Prokes click HERE
To check out The Big Ass Calendar click HERE
To connect with Carly Gilleland click HERE
To follow The Good Vibe Media click HERE
To visit The Good Vibe Studios click HERE
Produced by The Good Vibe Media