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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Steven Vitale doesn’t just run a surf boutique and an apparel brand—he’s building two movements. In this episode of The Unscripted Climb, hosts Christopher Beecham and Natalie Micale sit down with the founder of Cape Maid and Lifting Culture Apparel to unpack the reality of running multiple businesses, staying creative, and managing debt while still finding joy in the grind.
Whether you're scaling a retail brand or just trying to pay off startup credit cards, this episode will hit home.
Steven dives into:
- Building an online presence that actually converts
- Cross-promoting between two brands
- How DJing and music fuel his business creativity
- Market research and choosing the right brick-and-mortar location
- The not-so-glamorous side of entrepreneurship (spoiler: debt)
- Email marketing and customer loyalty strategies
- Why resilience and finding joy matter more than perfection
This isn’t just a highlight reel. It's the messy, motivating, brutally honest story of what it really takes to build something meaningful.
🧠 Keywords:
entrepreneurship, Steven Vitale, Cape Maid, Lifting Culture Apparel, small business, creativity in business, apparel brand, surf boutique, debt management, brick-and-mortar success, e-commerce strategy, market research, cross promotion, customer engagement, online presence, business growth, startup struggle, retail branding, email marketing, resilience, The Unscripted Climb podcast
⏱️ Chapters (YouTube):
00:00 – Entrepreneurial Journey and Cape Maid Overview 02:35 – The Brick and Mortar Experience 04:53 – Lifting Culture Apparel: A Decade of Learning 07:45 – Building a Culture in Business 10:29 – The Role of AI in Entrepreneurship 13:04 – Creativity and DJing as an Entrepreneurial Outlet 15:59 – Future Aspirations in Music and Business 18:35 – Comparing Business Models: Cape Maid vs. Lifting Culture 21:34 – Seasonality and Location Strategy for Cape Maid 25:03 – Understanding Sales Trends and Market Dynamics 27:33 – The Evolution of Lifting Culture and Event Marketing 30:45 – The Importance of Email Marketing and Customer Engagement 32:29 – Cross-Promotion Strategies for Business Growth 35:06 – Navigating Challenges and Making Tough Choices 38:43 – Balancing Debt and Entrepreneurship 44:05 – Embracing Change and Exploring New Opportunities
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