From Alice + Olivia to AI: Reinventing Entrepreneurship and Building Community with Rebecca Matchett

This episode features a conversation with Rebecca Matchett, co-founder and COO of Synchrony, about the grit, courage, and resilience required to build a business—even in the face of deep personal and professional reinvention.

Rebecca shares her entrepreneurial journey, starting with a volume-focused lemonade stand and later co-founding the iconic fashion brand Alice + Olivia, where she learned the importance of differentiation by using unique materials for pants.

The discussion covers Rebecca's powerful story as a lawyer, mom, and cancer survivor, including her decision to have a prophylactic mastectomy after learning she was BRCA positive, her cancer recurrence, and going through a full hysterectomy (flash menopause). She explains that her resilience stems from her ability to compartmentalize and focus only on actionable challenges.

Rebecca details how a dinner conversation led to her latest venture, Synchrony, a self-funded social ecosystem designed to connect verified neurodivergent young adults, combating loneliness and building community. She explains the user journey, where members are matched based on shared interests and communication preferences. A key feature is Jesse, an AI assistant who acts as a "wingman slash Mom Dad" to help users decode messages, start conversations, and foster social independence.

​Finally, Rebecca provides a raw look at the realities of building deep technology, discussing the high costs of development, the variability of AI tokenization, and the challenges of App Store and Google Play fees and approval processes. She reveals that Synchrony is looking toward building a Progressive Web App (PWA) to mitigate these platform risks.

Rebecca Matchett is a seasoned entrepreneur with over two decades of experience building and scaling businesses across fashion and technology. She is the co-founder of Alice + Olivia and has launched multiple brands, including Rebecca & Drew and TrioFit, where she developed a patented approach to women’s sizing. She is now co-founder and COO of Synchrony, an AI-driven platform designed to foster connection and community for neurodivergent individuals.

Connect with Rebecca:

Website: https://joinsynchrony.com/

LinkedIn: @synchrony-app

Susan Sly is the maven behind Raw and Real Entrepreneurship®. An award-winning AI entrepreneur and MIT Sloan alumna, Susan has carved out a niche at the forefront of the AI revolution, earning accolades as a top AI innovator in 2023 and a key figure in real-time AI advancements for 2024. With a storied career that blends rigorous academic insight with astute market strategies, Susan has emerged as a formidable founder, a discerning angel investor, a sought-after speaker, and a venerated voice in the business world. Her insights have graced platforms from CNN to CNBC and been quoted in leading publications like Forbes and MarketWatch. At the helm of the Raw and Real Entrepreneurship® podcast, Susan delivers unvarnished wisdom and strategies, empowering aspiring entrepreneurs and seasoned business veterans alike to navigate the challenges of the entrepreneurial landscape with confidence.

Connect With Susan:

Website: ⁠⁠⁠⁠⁠https://thepause.ai/⁠⁠⁠⁠⁠

Website: ⁠⁠⁠⁠⁠https://susansly.com⁠⁠⁠⁠⁠

LinkedIn⁠⁠:⁠⁠⁠@susansly⁠⁠⁠