# The Business of Betting on Yourself: Jennie Blackwood on Confidence Through Action

Page: https://stenobird.com/podcast/the-reluctant-entrepreneur-podcast-7049244/the-business-of-betting-on-yourself-jennie-blackwood-on-confidence-through-action
Text version: https://stenobird.com/podcast/the-reluctant-entrepreneur-podcast-7049244/the-business-of-betting-on-yourself-jennie-blackwood-on-confidence-through-action.md
Podcast: [The Reluctant Entrepreneur Podcast](https://stenobird.com/podcast/the-reluctant-entrepreneur-podcast-7049244)
Published: 2026-07-31T07:00:02+00:00
Episode link: https://www.spreaker.com/episode/the-business-of-betting-on-yourself-jennie-blackwood-on-confidence-through-action--72800008
Audio file: https://api.spreaker.com/download/episode/72800008/re_jb2_final_01.mp3
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Duration seconds: 3122

## Resource

Have you ever looked at someone else’s success and thought, “I could do that,” only to immediately follow it with, “But not yet. I’m not ready. I don’t know enough. I need a better plan.” That space between knowing you’re capable of more and actually taking the leap is where so many reluctant entrepreneurs live. It’s not always a lack of talent. It’s often perfectionism, fear, overthinking, or waiting for confidence to show up before taking action. My guest today, Jennie Blackwood, understands that space well. Jennie walked away from a demanding career in marketing and PR and began building businesses on her own terms. Since then, she’s built multiple six-figure businesses across several different ventures, including a boutique photobooth company, a custom laser engraving brand, real estate, and a charcuterie business that eventually became the foundation for her Cart-to-Cashflow coaching program. Today, Jennie helps women turn ideas into income, not by waiting until everything is perfect, but by building confidence through action. She also hosts the podcast Girl, Why Not You?, where she speaks to women who know they’re meant for more and are ready to create a business and life that actually fits them. In this episode, we’ll talk about Jennie’s own entrepreneurial journey, the moments of reinvention that shaped her, and why so many capable people stay stuck at the starting line. We’ll also talk about perfectionism, confidence, taking imperfect action, and what it really means to build a business and life on your own terms. Jennie's Website:https://www.jennieblackwood.com Jennie's Podcast: https://www.youtube.com/@girlwhynotyou

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