Girl Bossing Too Close to the Sun: Entrepreneurship Real Talk with Raven Ross

Apr 8, 2025

Raven Ross, a Pilates instructor and entrepreneur, rose to fame on Love is Blind before building her successful Pilates brand. In this lively discussion, she shares her entrepreneurial journey, revealing the real struggles behind the glamorous facade of business. Raven discusses the importance of purpose over clout, managing finances, and structuring a day for efficiency. She emphasizes the value of community and authenticity while navigating entrepreneurship, reminding listeners that true success is more than just social media virality.

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Intro

00:00 • 3min

Navigating the Entrepreneurial Journey

02:38 • 6min

Navigating Entrepreneurship and Embracing Authenticity

09:01 • 3min

Navigating the Entrepreneurial Landscape

11:32 • 7min

Navigating Entrepreneurship: Financial Fluctuations and Staying Energized

18:25 • 3min

Navigating Entrepreneurship: Challenges and Growth

21:21 • 7min

Embracing Change and Finding Balance in Entrepreneurship

28:40 • 6min

Empowering Female Entrepreneurs

34:24 • 16min

Building Community and Exciting New Ventures

50:06 • 3min

#286: What is entrepreneurship really like behind the glossy Instagram photos?

We’re welcoming back Raven to talk about the wild ride of entrepreneurship — figuring it out, failing, and building something real.

In this episode, Raven and Les sit down for a catch-up sharing the highs and lows of entrepreneurship and you’re invited to join the conversation. Raven shares what it took to go from juggling multiple jobs to building a thriving Pilates brand.

Les and Raven also get real about investing in your business, rebranding, asking for help, choosing purpose over clout, and why success is more than just going viral.

We Also Talk About…

Raven’s journey from working multiple jobs to building a pilates business.
Navigating the awkward in between, and handling perceived success.
The real cost of starting a business and what expenses to prepare for.
What a successful brand’s team looks like and the key roles that keep things running.
How to structure your day as an entrepreneur so you can work smarter, not harder.
How to build your empire on your own terms.

Resources:

Follow Raven on Instagram
Join Raven’s newsletter at https://pilatesbodyraven.com/
Subscribe to my Substack, Balance with Les
Check out my new brand Spacious Rituals and get your virtual planner for 2025!

Keep in touch with She’s So Lucky:

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