Julie Wainwright, Founder of The RealReal: Reinventing at 52, Building a Billion-Dollar Business, Turning Failure Into Fuel, & More
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.comSign 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 MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
17 Juni 20251h 10min
Jesse Mecham, Founder of YNAB: Mastering Money Mindset, Eliminating Financial Stress, and Giving Every Dollar a Job & More
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 MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
10 Juni 202543min
Scaling a Brand Beyond Year One: Tips for Intermediate Founders, Strategic Partnerships, Navigating Rooms with Confidence & More
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.comGet 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/dreambiggerProduced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
3 Juni 202544min
Jordan Harper, Board Certified NP & Founder of Barefaced: Preventative Anti-Aging, Peptides, Melasma Management & More
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.comFor 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 MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
27 Maj 202545min
Serena Kerrigan, Creator, Director & Producer: Personal Branding 101, Dating Without Drama, Launching a TV show, & More
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.comIf 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 #rulapodProduced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
20 Maj 20251h
Cynthia Rowley and Kit Keenan: Lessons on Growth from a Mother-Daughter Duo, Surviving Setbacks, Creatively Evolving, & More
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.comFor 15% off your first purchase, visit linnebotanicals.com. Use code DREAMBIGGER at checkout. Offer cannot be combined.Produced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
13 Maj 202547min
Kayla Barnes, Biohacking Expert: Longevity Habits, Cycle-Synced Fitness Routine, How to Detox, & More
On today’s episode I am speaking with biohacking expert, Kayla Barnes. She breaks down her non-negotiables for longevity and optimal health—most of which are completely free. From mastering high-quality sleep and harnessing morning sunlight to syncing your workouts with your menstrual cycle, Kayla shares practical, research-backed strategies that support hormone balance, heart health, and cellular longevity. You'll learn her daily detox rituals, red light therapy routine, and how to optimize fertility and fitness through every phase of your cycle. Plus, hear her tips on boosting testosterone naturally, supporting hair growth, and reducing stubborn belly fat in your 30s. This episode is packed with actionable tools for women looking to thrive at every stage of life. Enjoy!To connect with Kayla on Instagram, click HERE.To check out Kayla’s website, click HERE.To listen to Kayla’s podcast, Longevity Optimization, 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.comGet $25 off your first purchase when you go to TheRealReal.com/DREAMBIGGERReady 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.For 15% off your first purchase visit linnebotanicals.com use code DREAMBIGGER at checkout. Offer cannot be combined.Produced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
6 Maj 20251h 5min
Bryony Deery, Founder of Pilates by Bryony: Sustainable Fitness Habits, Balancing Wellness with a Social Life, and Glow Up Tips for Summer
In today’s episode, I’m teaming up with my dear friend Bryony Deery to chat all things sustainable fitness, finding balance between wellness and a social life, and getting ready for your ultimate summer glow-up. We dive into the TONE challenge and how much fun we had filming it together—it was such a special experience blending Arrae and Pilates by Bryony in a way that felt both energizing and empowering. Bryony’s workouts are truly my favorite; it always feels like she’s right there in the studio with me. This episode is full of helpful tips to help you feel your best, push yourself a little further, and of course, share a few laughs along the way. Enjoy!To connect with Bryony on Instagram, click HERE.To connect with Bryony on Tiktok, click HERE.To check out Pilates by Bryony, click HERE.To listen to Beyond the Mat, 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.Spring into action with the healthy swap to Caraway. Our favorite cookware set will save you $150 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 to our listeners, so visit Carawayhome.com/DREAMBIGGER or use code DREAMBIGGER at checkout. Non-Toxic cookware made modern.Get 10% off your first order sitewide with code DREAMBIGGER at OSEAMalibu.comGet 15% off Branch Basics with the code DREAMBIGGER at https://branchbasics.com/DREAMBIGGER #branchbasicspodSave 15% off my favorite Red Light Face Mask from BON CHARGE by using code DREAMBIGGER at www.boncharge.comProduced by Dear MediaSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
29 Apr 20251h 5min
