Scared SHITLESS

About Scared SHITLESS

This podcast is about having the guts to do what terrifies you... on purpose. It’s for people chasing their calling, even if it means tripping over a few obstacles (or faceplanting into them). Tune in for real stories of real people who dared to follow their own path—even when it was uphill, in the snow, both ways.

Publisher

Sarah Sémajuste

Category

education

Language

en

Explicit

No

First episode

25 May 2025

Latest episode

28 Sept 2026

Latest episodes

24 episodes in the feed.

1. 

   28 Sept 2026

   Real Estate Stole Her Childhood. Then She Invested | Roz Woodland | EP 24

   What if your biggest fear became your greatest opportunity? For years, Roz Woodland believed real estate was the reason her childhood was filled with fear, uncertainty, and financial stress. Watching her family struggle after her father left a secure career to invest in real estate taught her one powerful lesson: there's never enough. So when her husband wanted to invest in real estate, she wanted nothing to do with it. In this episode of Scared Sh*tless, Roz shares the deeply personal story of how she went from fearing wealth and risk to becoming a real estate investor, entrepreneur, and coach who now helps others rewrite their own money story. This isn't just a conversation about investing. It's about healing your relationship with money, navigating fear in marriage and business, and learning that your past doesn't have to dictate your future. Why Roz says "real estate stole my childhood." The moment that completely changed her view of wealth. How childhood experiences shape our financial decisions as adults. What happens when investment deals go wrong—and how to respond. Marriage, money, and getting on the same page with your partner. Why your environment matters more than willpower. Building generational wealth without repeating generational fear. If you've ever been afraid to invest, afraid to take a risk, or felt like your past is holding you back, this conversation is for you. Roz Woodland is a real estate investor, entrepreneur, speaker, and co-founder of Woodland Realty Investments. She helps people challenge limiting beliefs around money, wealth, and possibility so they can intentionally build a different future. Website: woodlandrealtyinvestments.com Website: riseandshineevenif.com Facebook: Roz Woodland Scared Sh*tless is the podcast where entrepreneurs, investors, and high performers tell the stories behind the risks they took, the fears they faced, and the moments that changed everything. 🎙️ If this episode resonated with you, follow Scared Sh*tless on Spotify, Apple Podcasts, or wherever you listen to podcasts, and share it with someone who's rewriting their relationship with money.

2. 

   7 Aug 2026

   Balance Is A Lie When You're Building A Business | EP 23

   What if the balance you've been trying to create is actually holding you back? Building a business or pursuing something meaningful requires time, focus, and sacrifice. And sometimes, that means less time for friends, family, hobbies, and the things you enjoy. But does that mean you have to choose between success and having a life? In this episode of Scared Sh*tless, we challenge the idea of work-life balance and explore why some seasons of entrepreneurship may require you to prioritize your goals over balance. The goal isn't to live out of balance forever—it's to make intentional sacrifices now that can create more freedom, flexibility, and balance later. We explore the reality of building something significant, the importance of dedicating time to your craft, and the sacrifices that can come with pursuing success. If you've ever struggled with balancing your business, career, relationships, and personal life, this conversation may change the way you think about what balance really means. Scared Sh*tless is a podcast about choosing courage over comfort. Each episode explores the fears, failures, risks, sacrifices, and defining moments behind entrepreneurship, business, investing, personal growth, and success. The question is: What are you willing to temporarily sacrifice to build the life you want?

3. 

   31 Jul 2026

   The Hardest Part Wasn't Starting Over... It Was Losing My Identity | Randy Powell | EP 22

   For nearly a decade, Randy Powell was “the barber.” It wasn't just his career—it was his identity, his community, and the life he had built from the ground up. Then he walked away. No guarantees. No clients. No backup plan. Today, Randy has spent more than 18 years building businesses, investing in real estate, and helping others create financial freedom. But getting there meant letting go of the identity that had defined him for years. In this episode of Scared Shitless, Randy opens up about the leap from barber to entrepreneur, real estate investor, and Realtor—and what it actually felt like to start over. We talk about his first real estate investment, the mistakes he made early on, the mentors who changed his approach, why he bought two laundromats, and what he's learned about building wealth, taking calculated risks, and creating businesses that give you freedom rather than simply creating another job. But underneath all of that is a bigger question: What happens when the person you've been is no longer the person you want to become? Randy's story is a reminder that starting over doesn't mean starting from nothing. Sometimes, you have to let go of the identity that's holding you back before you can build the life you actually want. If you're thinking about changing careers, starting a business, investing, or simply taking a bigger risk with your life, this conversation will hit home. About Randy Powell Randy Powell is a real estate investor, Realtor, and entrepreneur with more than 18 years of experience. He has built a portfolio of investment properties, renovated homes, owned two laundromats, and helps others navigate real estate and pursue financial freedom. He can be reached on Instagram @randypowell_ About Scared Shitless Scared Sh*tless is a podcast about ordinary people who choose courage over comfort. We explore the fears, failures, risks, and defining moments that happen before success becomes visible—and the decisions that change everything. Because sometimes the biggest risk isn't failing. It's staying the person you've already outgrown.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Spotify

5.0 / 5

2 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.