Episodes
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Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”
For a young startup, hiring experienced executives and immediately getting out of their way can be harmful; founders may need people only slightly ahead of them who remain close to the work.
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Advice Line with Tope Awotona of Calendly
Tope says the barrier to launching application software is lower than ever because AI tools can turn a clearly articulated set of requirements into an initial product; the harder task is validating a real problem and reaching product-market fit.
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FIGS: Trina Spear and Heather Hasson. The $2.5 Billion Scrubs Brand That Investors Said Would Never Work
Heather’s Kenya experience convinced her that uniforms can change how people feel and perform, first for schoolchildren and later for healthcare professionals.
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Advice Line with Seth Berkowitz of Insomnia Cookies
Insomnia Cookies aims to grow to 1,800 stores globally without franchising, maintaining direct control to ensure quality and innovation.
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Sweet Loren’s: Loren Castle. How A Recipe Makeover Built a National Cookie Brand
Strategic, small decisions like choosing a credit card can significantly improve cash flow and support scaling for small businesses.
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Advice Line with Tara Bosch of SmartSweets
Clarity about the future vision of a business helps accelerate growth and strategic decision-making.
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Alamo Drafthouse Cinema: Tim and Karrie League (2023)
Hard work and relentless innovation can overcome industry obstacles, as demonstrated by the Leagues' challenging start and creative efforts.
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Advice Line with Nick Green of Thrive Market
Data analysis guides Thrive Market's product development, especially identifying unmet consumer needs through 'empty searches'.
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10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention
Fear is an inherent part of entrepreneurship, and recognizing it can help turn it into motivation.
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Advice Line with Scott Tannen of Boll & Branch and Jamie Siminoff of Ring (2025)
Maintaining control and authenticity in a business is crucial, and raising outside capital can significantly shift a company's focus and priorities.
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Seventh Generation: Alan Newman and Jeffrey Hollender. A Partnership that Flourished—until it Failed. (2021)
Saying yes can open doors and create opportunities, as Jeffrey did when he took on new ventures without initial interest or investment.
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Advice Line with Danny Meyer of Shake Shack
Building company culture starts with specific expected behaviors that everyone understands and embodies.
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Banza: Brian Rudolph. The Chickpea Pasta That Nearly Turned to Mush
Building a successful food brand requires persistent experimentation and willingness to ship products that are 'good enough' rather than perfect.
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Advice Line with Michelle Wahler of Beyond Yoga
Focus on your core motivation in business rather than just pursuing funding or rapid expansion.
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Thrive Causemetics: Karissa Bodnar. How a Beauty Business Made Millions for a Mission
Authentic storytelling and mission-driven purpose can significantly differentiate a brand in a crowded market.
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Advice Line with Kip Tindell of The Container Store
Steady, humble growth is often more sustainable than aggressive expansion.
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Bogg Bag: Kim Vaccarella. The $100 Million Business She Almost Abandoned
Resilience and perseverance are crucial in overcoming startup setbacks and failures.
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Advice Line with Ben Goodwin of Olipop
Entrepreneurs should prioritize their core mission and values, avoiding compromises that dilute their brand integrity.
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Late July Snacks: Nicole Bernard Dawes. Crackers and Cookies were Failing… Tortilla Chips Saved Them
Building a successful food brand requires persistence, resilience, and the ability to pivot in response to market needs or crises.
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Advice Line with Daymond John of FUBU
A compelling pitch should tell a authentic story, demonstrate market knowledge, and include resilience and confidence.
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