EPISODE · Jun 9, 2026 · 58 MIN
Entrepreneur by Default: Toby Myles & Jen Baxter on Turning Setbacks into Successes
from Her Origin Story · host Host: Toby Myles, Guest: Jen Baxter, Editor: Ilorah Dela Cruz, Original Cover Art: Isabel Paterson
Check Out These Highlights: Jen Baxter’s story is one of unexpected pivots and resilience. After taking a leap of faith into book publishing, she faced sudden layoffs and the uncertainty of starting over. What began as a side project with Substack turned into a coaching business helping authors and entrepreneurs launch meaningful newsletters. Along the way, Jen embraced AI tools to support clients in amplifying their voices and building systems that work. In this episode, Jen shares the turning points that shaped her career, how she reframed setbacks into opportunities, and why she calls herself an “entrepreneur by default.” Listeners will walk away with insights on balancing stability and creativity, using technology with integrity, and building a business ecosystem that supports both freedom and security. About Jen Baxter: Jen Baxter is a copywriter, strategist, and newsletter coach who helps authors and entrepreneurs create intentional, reader‑focused newsletters. She blends her background in publishing with her expertise in Substack and AI tools to help clients build sustainable systems and authentic connections. Connect with Jen: 🌐 Website: https://www.jenbaxter.com/ 💼 LinkedIn: https://www.linkedin.com/in/jenbaxter/ 📑 Substack: https://jenbaxter.substack.com/ Stalk Me Online! About Me: https://tobymyles.com/about/ Free Gift: The Nashville Method: 5-Day Storytelling Mini-Course Subscribe to Her Origin Story on your favorite platform. New episodes every week with real, raw stories about the moments that started it all. Episode Notes Footer:Her Origin Story is produced by Toby Myles Copywriting, and podcast editor Ilorah Dela CruzAll content © 2026 Toby Myles. All rights reserved.
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What this episode covers
Jen Baxter shares her journey from corporate copywriting to building her own path through newsletters, Substack coaching, and AI tools; plus why becoming an “entrepreneur by default” can sometimes feel more stable than chasing the next job.
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Entrepreneur by Default: Toby Myles & Jen Baxter on Turning Setbacks into Successes
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