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

#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 InstagramJoin Raven’s newsletter at https://pilatesbodyraven.com/Subscribe to my Substack, Balance with LesCheck out my new brand Spacious Rituals and get your virtual planner for 2025!Keep in touch with She’s So Lucky:Watch on YouTube @shessoluckypodFollow on IG: @lesalfred @shessoluckypodFollow on TikTok @balancedlesSponsors:Quince | Get quiet luxury without luxury prices at Quince. Go to quince.com/balancedles for free shipping and 365-day return on your next order.LMNT | LMNT is a zero sugar electrolyte drink mix with a research-backed ratio of electrolytes. To try it out go to drinkLMNT.com/balancedles to receive a free LMNT sample pack with any purchase.Nutrafol | | Get stronger, healthier hair with Nutrafol. For a limited time, Nutrafol is offering $10 OFF your first month’s subscription and free shipping when you go to nutrafol.com and enter promo code BALANCEDLES.Pique | Nandaka coffee isn’t just clean—it’s next-level wellness in every sip. Get 20% off plus a FREE starter kit when you shop at Piquelife.com/BALANCEDLESSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What this episode covers

#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 InstagramJoin Raven’s newsletter at https://pilatesbodyraven.com/Subscribe to my Substack, Balance with LesCheck out my new brand Spacious Rituals and get your virtual planner for 2025!Keep in touch with She’s So Lucky:Watch on YouTube @shessoluckypodFollow on IG: @lesalfred @shessoluckypodFollow on TikTok @balancedlesSponsors:Quince | Get quiet luxury without luxury prices at Quince. Go to quince.com/balancedles for free shipping and 365-day return on your next order.LMNT | LMNT is a zero sugar electrolyte drink mix with a research-backed ratio of electrolytes. To try it out go to drinkLMNT.com/balancedles to receive a free LMNT sample pack with any purchase.Nutrafol | | Get stronger, healthier hair with Nutrafol. For a limited time, Nutrafol is offering $10 OFF your first month’s subscription and free shipping when you go to nutrafol.com and enter promo code BALANCEDLES.Pique | Nandaka coffee isn’t just clean—it’s next-level wellness in every sip. Get 20% off plus a FREE starter kit when you shop at Piquelife.com/BALANCEDLES See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

NOW PLAYING

0:00 52:36

1×

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

Share this episode

Similar Episodes

I'm ok

Mar 26, 2026 ·1m

REMIX: Why we over-shop and compulsively acquire, and how to stop, with Dr Jan Eppingstall

Jan 9, 2026 ·61m

REMIX: OCD and hoarding disorder with Jenna Overbaugh

Jan 2, 2026 ·47m

REMIX: Therapy and hoarding disorder - what are the options? With Dr Jan Eppingstall

Dec 26, 2025 ·78m

REMIX: ADHD and hoarding disorder with Professor Sharon Morein

Dec 21, 2025 ·46m

#207 13 actionable pieces of mental health advice from six former podcast guests

Dec 12, 2025 ·53m

Similar Podcasts

That Hoarder: Overcome Compulsive Hoarding That Hoarder Hoarding disorder is stigmatised and people who hoard feel vast amounts of shame. This podcast began life as an audio diary, an anonymous outlet for somebody with this weird condition. That Hoarder speaks about her experiences living with compulsive hoarding, she interviews therapists, academics, researchers, children of hoarders, professional organisers and influencers, and she shares insight and tips for others with the problem. Listened to by people who hoard as well as those who love them and those who work with them, Overcome Compulsive Hoarding with That Hoarder aims to shatter the stigma, share the truth and speak openly and honestly to improve lives. LIGHTS, CAMERA, SMILE! Creatives Club Media Lights, Camera, Smile, is a podcast for anyone with a dream to share something with the world, out of the overflow of themselves - be it their mind, their heart, their personalities, and much more. Each of us are alive in this moment in time, with an innate ability to have ideas and create various things to benefit both ourselves and the people around us for a reason, and here, you will find the encouragement, the inspiration, and the motivation to do just that. Hosted by Cicily, founder of Creatives Club, she dives into various topics surrounding creativity and business. Exploring entrepreneurship for creatives in a corporate reality, sharing tips and tricks in a media centered company, answering questions regarding what a creative actually is are just a few of the things discussed on this podcast. Be encouraged to create for yourself as Cicily gets vulnerable by pivoting the camera to herself for the first time.To submit questions for Cicily to answer, or have her address certain t She’s a Hazard to Herself She’s a Hazard Hi there, I’m Mallory, and I’d like to invite you into our world with “She’s a Hazard to Herself!” Join us as we navigate life with Multiple Sclerosis from the seat of my power wheelchair. Discover stories of resilience, family, and the community we’ve built around chronic illness. Whether you’re impacted by MS or want to learn from our journey, there’s something here for you. So why wait? Subscribe to “She’s a Hazard to Herself” on your favorite podcast app and be part of our journey today. Let’s lift each other up, one episode at a time! Invictus by Greyana, A Tomione Podfic M+G Readings Sporadic uploads thanks to gallstones.Voldemort intended the object to be used by his most loyal follower in the event that his horcruxes were destroyed, but it ended up in Hermione’s possession instead.It sent her back to a time when he was much less the monster that she’d always known him to be. Nothing could have prepared her for the intelligence and charm of Tom Riddle.He isn’t who she thought he was.Hermione discovers that it’s a dark descent into the madness of the man she should hate, but can’t… a descent she will never emerge fr

Frequently Asked Questions

How long is this episode of She's So Lucky?

This episode is 52 minutes long.

When was this She's So Lucky episode published?

This episode was published on April 8, 2025.

What is this episode about?

Can I download this She's So Lucky episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.

URL copied to clipboard!