On today’s episode I am speaking with Julie Wainwright, founder of The Real Real. At 52, after the public collapse of Pets.com and a personal reset, Julie Wainwright launched The RealReal—an idea that would redefine luxury resale and grow into a billion-dollar business. In this episode, Julie shares how failure made her fearless, why she never let age define her ambitions, and the behind-the-scenes story of how The RealReal got off the ground. From clearing out celebrity closets in LA and building a brand rooted in trust and authenticity, Julie opens up about entrepreneurship, resilience, and what she wishes she’d done differently. Plus, she discusses the challenges of leadership, getting fired from her own company, and what’s next. Enjoy!
To connect with Julie on Instagram, click HERE.
To check out The Real Real, click HERE.
To check out Julie’s book Time to Get Real: How I Built a Billion-Dollar Business That Rocked the Fashion Industry, click HERE.
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
Save 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.com
Sign up for your one-dollar-per-month trial period at shopify.com/dreambigger
Give your summer closet and upgrade–with Quince. Go to Quince.com/dreambigger for free shipping on your order and 365 day returns.
Just visit ProlonLife.com/DREAMBIGGER to claim your 15% discount and your bonus gift.
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
On today’s episode I am speaking with Jesse Mecham, founder of You Need a Budget (YNAB). He shares the inspiring story behind building one of the most beloved budgeting tools—starting with a simple spreadsheet in 2004. He dives deep into the principles of giving every dollar a job, the five key questions to ask when managing your money, and how to eliminate financial stress with a mindset shift. Whether you're just starting your financial journey or looking to reset your habits with a “money detox,” Jesse offers actionable insights to help you build a sustainable, stress-free relationship with money. Enjoy!
To check out YNAB on Instagram, click HERE.
To check out YNAB’s Website, click HERE.
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
Visit www.ynab.com/dreambigger to claim an exclusive three-free month trial, with no credit card required.
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
From Q&A’s and break up tips to simply navigating every stage of life, influencer-turned-entrepreneur Payton Sartain brings you the sisterly advice you didn’t know you needed and honest conversations you’ve always wanted. Whether it’s Payton alone or a conversation with a friend, Note to Self is a space to get grounded, explore new perspectives, and ultimately, empower yourself and others. Grab some wine or a mocktail and enjoy the conversation!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
On today’s solo episode I dive into what it takes to scale a brand after the initial launch phase. Aimed at intermediate founders in year two and beyond, we explore actionable strategies for continued growth—personally and professionally. From reading habits and mindset shifts to building intentional partnerships and navigating rooms with confidence, this conversation covers the often-overlooked emotional and spiritual aspects of entrepreneurship. I also touch on managing imposter syndrome, tapping into your alter ego, and why protecting your time and energy is key to long-term success. Enjoy!
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
Save 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.com
Get 10% off your first order sitewide with code DREAMBIGGER as OSEAMalibu.com. You’ll get free samples with every order, and free shipping on orders over $60. Head to OSEAMalibu.com and use code DREAMBIGGER for 10% off.
Ready to clean up your home and your health? Head to BranchBasics.com to shop their Premium Starter Kit and use code DREAMBIGGER at BranchBasics.com. That’s 15% off your New Branch Basics Premium Starter Kit at BranchBasics.com with promo code DREAMBIGGER. Make the change today – because you and your family deserve better.
Listeners of Dream Bigger can claim an exclusive three-month free trial, with no credit card required at www.YNAB.com/dreambigger
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
On today’s episode I am speaking with Jordan Harper, Board-Certified Nurse Practitioner and founder of Barefaced, to break down what actually works when it comes to preventative anti-aging. Jordan shares her expert take on the truth behind in-office skin tightening treatments, the must-have "Core 4" products for your 20s, and how to effectively manage melasma. We also dive into the rising buzz around peptides—both topical and injectable—and why gut health and lifestyle choices matter more than you think for glowing skin. Whether you're skincare-savvy or just getting started, this episode is packed with no-fluff advice to help you invest in your long-term skin and health. Enjoy!
To connect with Jordan on Instagram, click HERE.
To connect with Jordan on Tiktok, click HERE.
To check out Barefaced, click HERE.
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
And just as a reminder, their iconic Cookware Set comes with the Sauté Pan, Fry Pan, Dutch Oven and Sauce Pan. PLus lids for all of them, a canvas lid holder and magnetic pan rack for storage! It’s the ultimate kitchen set-up and will save you money versus buying the items individually. Plus, if you visit Carawayhome.com/DREAMBIGGER you can take an additional 10% off your next purchase. This deal is exclusive for our listeners, so visit Carawayhome.com/DREAMBIGGER or use code DREAMBIGGER at checkout. Caraway. Non-Toxic cookware made modern.
Save 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.com
For 15% off your first purchase visit linnebotanicals.com. Use code DREAMBIGGER at checkout. Offer cannot be combined.
Get $25 off your first purchase when you go to TheRealReal.com/dreambigger.
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
On today’s episode I am speaking with Serena Kerrigan—creator, director, producer, and unapologetic powerhouse. She dives into her journey from launching SFK TV to creating her new scripted series Older, Hotter, Wiser, premiering May 19th on Peacock. She shares candid insights on building a personal brand, turning doubt into drive, dating without drama, and the lessons learned from launching products that don’t resonate. From her pivot into book writing to navigating modern relationships with clarity and confidence, Serena keeps it real on success, self-worth, and showing up fully as yourself. Enjoy!
To connect with Serena on Instagram, click HERE.
To connect with Serena on Tiktok, click HERE.
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
Save 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.com
If you want to see less carts being abandoned, it's time for you to head over to Shopify. Sign up for your one-dollar-per-month trial and start selling today at Shopify.com/DREAMBIGGER.
To help you jumpstart a plan that delivers real results, Prolon is offering The Dream Bigger Podcast listeners an exclusive chance to be among the first to try Next Gen-with 15% off sitewide plus a $40 bonus gift when you subscribe to their 5-day program! Just visit ProlonLife.com/DREAMBIGGER
Rula patients typically pay $15 per session when using insurance. Connect with quality therapists and mental health experts who specialize in you at https://www.rula.com/dreambigger #rulapod
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
On today’s episode I am speaking with fashion icon Cynthia Rowley and her daughter, content creator and entrepreneur Kit Keenan. They share an intimate look at their unique mother-daughter dynamic. From growing up in the world of fashion to building a brand that bridges generations, Cynthia and Kit discuss how they've evolved both personally and professionally. They open up about creative reinvention, the importance of routine and confidence, handling criticism online, and what it takes to stay relevant in a rapidly changing world. Whether you're building a business, navigating family dynamics, or simply seeking inspiration, this conversation offers real lessons on growth, resilience, and redefining success—together. Enjoy!
To connect with Cynthia on Instagram, click HERE.
To connect with Kit on Instagram, click HERE.
To connect with Kit on Tiktok, click HERE.
To connect with Siff on Instagram, click HERE.
To connect with Siff on Tiktok, click HERE.
To learn more about Arrae, click HERE.
To check out Siff’s LTK, click HERE.
To check out Siff’s Amazon StoreFront, click HERE.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.
Treat your closet to a little summer glow-up with Quince. Go to Quince.com/dreambigger for free shipping on your order and 365-day returns.
Save 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.com
For 15% off your first purchase, visit linnebotanicals.com. Use code DREAMBIGGER at checkout. Offer cannot be combined.
Produced by Dear Media
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
