A great story does not skip the hard parts, and Erin Flynn refuses to. On BeTempered, hosts Dan Schmidt and Ben Spahr sit down with Erin to trace the real path from Indiana gym floors to Silicon Valley boardrooms. She chased a dream, ran into walls, and still chose to build a company and a life that actually fit. Her early chapters read like a crash course in grit. She graduated into the 2009 recession, rode a bus six hours a day to an unpaid internship, and turned a blog into a bridge between brands and creators. Then came her first startup, the shock of blunt sexism in investor rooms, and a humbling move back into her childhood bedroom when both money and luck ran out.

What changed everything was not louder hustle. It was alignment. Erin joined Cladwell, helped it grow, and then faced the VC treadmill that demanded free growth and breakneck scale. When the numbers no longer served customers or the mission, she did something few founders even consider. She bought back the business, raised values aligned capital, and rebuilt the app around a simple promise. Cladwell now helps people get dressed with what they already own, pairing weather smart suggestions with a capsule wardrobe philosophy that encourages doing more with less. Motherhood added urgency and perspective, faith shifted from a slogan into a steady rhythm, and her love for design grew into real estate renovations, boutique lofts, and kitchen design studios that put craft and service at the center.

The conversation also dives into her bestselling book, The Road Less Worn, where she clears out the closet of her life and keeps only what still fits. Identity, failure, resilience, and the courage to swim sideways out of the rip current. For anyone who has felt pressured into a version of success that did not feel like their own, Erin’s approach is a lifeline. Choose profits over posturing, customers over vanity metrics, and values over speed. She shares practical insight on fundraising, bias, creative focus, and building businesses that breathe, along with a hopeful reminder that company failure is not personal failure.

Connect with the hosts at www.betempered.com and www.patreon.com/betempered. Explore Erin’s work at https://cladwell.com/ and her design and development projects at https://eastmain.com/. If this conversation encouraged you, follow the show, share it with someone who is building their own path, and leave a quick review so more people can find these stories.

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