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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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We went live with Rebecca Newenham — founder of Get Ahead, franchise consultant, mentor, and passionate advocate for flexible working — to talk honestly about what it really takes to make the leap from employee to entrepreneur.
Rebecca shared her journey from being a corporate retail buyer to running a thriving outsourcing agency, giving practical advice to anyone thinking about starting their own business.
We discussed:
- Why there’s still a stigma around entrepreneurship — and how to reframe selling.
- How to test an idea and take small steps before leaving corporate life.
- The importance of systems, accountability, and structure when you’re your own boss.
- Thinking about money, pricing, and financial risk in those early stages.
- Options for scaling — from freelancers and associates to franchising.
- Why does success look different for everyone, and how do you define your version?
Key Takeaways:
- You don’t have to quit overnight — ease into entrepreneurship step by step.
- Selling gets simple when you know your value and own it.
- Strong systems + strong community = entrepreneurship without loneliness.
- Growth starts with you — invest in yourself as much as your business.
👉 Whether you’re dreaming of leaving corporate, already running a side hustle, or looking to scale, this Live is full of honest insights and practical tools to help you move forward.
Show Links:
Connect With Our Host, Elizabeth Willetts Here
Connect With Rebecca on LinkedIn Here
Visit the Get Ahead Website Here
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Chapters
1. Welcome & Show Purpose (00:00:00)
2. Sponsor: Investing in Women (00:01:15)
3. Today’s Topic: Employee to Entrepreneur (00:02:06)
4. Guest Intro: Rebecca’s Journey (00:03:02)
5. Outsourcing To Scale Smart (00:04:10)
6. Stigma, Security & Starting Anyway (00:05:37)
7. Traits That Help Entrepreneurs Thrive (00:06:40)
8. Making Sales Feel Human (00:08:20)
9. Mentors, Community & Avoiding Loneliness (00:10:06)
10. Building Your Own Ladder (00:11:32)
11. Fear, Failure & Safer Transitions (00:12:30)
12. Money, Pricing & Value (00:14:05)
13. Packages, Positioning & Clarity (00:16:03)
14. Early Clients & Wearing All Hats (00:17:23)
15. Scaling Via Freelancers (00:18:19)
16. Systems, Routines & Boundaries (00:19:50)
17. Productivity Without Long Hours (00:22:07)
18. Accountability, Targets & Tools (00:23:11)
19. Test, Iterate & Keep It Simple (00:24:22)
20. Portfolio Careers & Energy (00:25:30)
21. Invest In Yourself (00:26:49)
22. Networking That Actually Works (00:28:00)
23. AI, Co‑working & Modern Leverage (00:29:18)
171 episodes
