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Episode Stack: https://stackl.ist/3W1QAGR

I had THE BEST conversation with Caroline Clark, Co-Founder and CEO of Arcade, about the journey from zero to building a product that's changing how teams create interactive demos.

We talked about her path from consulting to product marketing at companies like Atlassian, and what led her to start Arcade. What stood out to me was her honesty about the hard parts of building a company. The burnout, the failed launches, the moments at 4:30 AM questioning everything.

Some things that stuck with me:

• Why the best market isn't always the obvious one
• The real cost of being on the hook for marketing output (and why she built Arcade)
• How a "failed" product launch became their most successful enterprise offering
• The importance of staying close to what brings you joy when building

If you're in the early stages of building something, Caroline's advice about being passionate and not getting too attached to one-off moments is worth hearing. She's built up what she calls a "lower bar for embarrassment" over time, which feels like an underrated founder skill.

Chapters

00:46 - Introduction and Background
11:52 - Early Career and Transition to Marketing
25:21 - Joining Atlassian and Learning from Failures
34:12 - The Importance of Market Fit
45:44 - Venture Capital Insights and Growth Mindset
56:30 - Building Arcade: Challenges and Successes
1:09:18 - Future of Arcade and AI Investments
1:22:14 - Advice for Aspiring Entrepreneurs

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Episode Stack: https://stackl.ist/48oXZao

Summary

In this episode, Grady Teske, founder of Rising Tides, shares his journey from helping multinational manufacturers to founding Rising Tides, a company focused on building distribution and marketing strategies. Grady discusses the importance of understanding one's core function and audience, and how aligning these elements can lead to success. He emphasizes the value of authenticity and human connection in business, and how automation and AI can enhance these relationships. Grady also reflects on the lessons learned from his entrepreneurial journey, offering insights for aspiring founders on building effective systems and processes. Join Grady and Kyle Hudson as they explore the intricacies of scaling businesses and the power of distribution in today's market.

Chapters

00:00 - Introduction and Setting the Scene
01:36 - The Importance of Authenticity in Media
04:13 - Grady's Journey to Entrepreneurship
10:19 - Building Rising Tides: The Evolution of a Business
15:29 - The Role of Distribution in Business Success
22:07 - Automation and the Future of Marketing
28:15 - Navigating Growth and Scaling Challenges
34:15 - The Power of Community and Connection
40:08 - Advice for Aspiring Entrepreneurs
45:57 - Looking Ahead: Future Plans for Rising Tides

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Episode Stack: https://stackl.ist/4n1utvL

Summary

In this conversation, Tara shares her entrepreneurial journey, detailing the influences that shaped her spirit, the challenges faced while building Rupa, and the lessons learned along the way. From early inspirations to the complexities of team dynamics and the emotional aftermath of selling her company, Tara emphasizes the importance of resilience, gut instinct, and the continuous pursuit of growth in both personal and professional realms.

Chapters

00:00 - Introduction and Context Setting
03:15 - Early Influences and Entrepreneurial Spirit
09:19 - Career Beginnings and Lessons Learned
15:53 - The Birth of Rupa and Vision for Healthcare
21:03 - The Birth of a Non-Alcoholic Bar Idea
26:28 - Transformative Patient Stories and Evidence-Based Medicine
37:49 - Building Momentum and Overcoming Challenges
42:36 - Setting High Expectations and Team Dynamics
47:33 - Reflections on Selling Rupa Health

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In this episode, I have the pleasure of interviewing Tony Clemendor, who was not only my coach but also a fantastic mentor. As a fellow neurodivergent, Tony brings a unique perspective to entrepreneurship, sharing his journey from bootstrapping a startup to scaling it to $80 million in revenue.

We discuss his insights on the new economy, the simplicity of entrepreneurship, and the importance of adaptation. Tony's creative approach to overcoming challenges and his belief that every first idea is just a draft make this conversation both inspiring and practical for aspiring entrepreneurs.

You're going to love the insights uncovered in this episode.

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Episode Stack: https://stackl.ist/3JwxNAl

Summary

In this conversation, Cristina Cordova shares her journey through the startup ecosystem, detailing her experiences at various companies including Tapulus, Google, Stripe, Notion, and Linear. She discusses the importance of company culture, the role of partnerships in growth, and the significance of finding the right fit in a startup. Cristina emphasizes the value of working with strong founders and the need for startups to have a clear vision and product-market fit. Her insights provide valuable lessons for aspiring entrepreneurs and those looking to navigate the tech industry.

Chapters

00:00 The Journey into Startups
11:24 Finding the Right Fit in Tech
18:20 Building Relationships and Partnerships
23:59 Building Payment Infrastructure: The Early Days of Stripe
29:19 Transitioning to Notion: A Personal Journey
36:04 Joining Linear: The Right Fit and Company Culture
44:02 Key Insights for Startup Success: Lessons Learned

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Episode Stack: https://stackl.ist/41vbWPM

In this conversation, Claude Silver, the Chief Heart Officer at VaynerX, discusses her journey and the importance of empathy in the workplace. She emphasizes the need for self-awareness, understanding emotions, and creating a culture that values people. Silver shares insights on hiring practices, the transition to her current role, and the significance of communication in a remote work environment. She highlights the importance of building a people-centric organization and the future goals she aims to achieve in her role.

Takeaways

• Empathy is a superpower in leadership.
• Self-awareness is crucial for effective communication.
• Creating a culture of safety allows for open expression.
• Hiring should focus on culture addition, not just fit.
• Understanding employees' personal lives enhances workplace culture.
• Communication must be intentional and consistent.
• Celebrating small wins fosters a positive environment.
• Emotional intelligence is key in navigating workplace dynamics.
• Building relationships is essential for a thriving organization.
• The role of Chief Heart Officer is about serving people.

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Episode Stack: https://stackl.ist/4c0BOHv

Today, we have a riveting conversation with Andy Budd, a seasoned design leader and former founder who takes us through the exciting trajectory of his life.

From learning HTML in a hostel in Singapore to pioneering one of the first UX agencies in the UK, Andy shares his insights on embracing self-reliance, breaking the mold, and the transformative power of design in building brilliant products.

We also delve into his experience with venture capital, where he helps other entrepreneurs navigate their journeys. Join host Kyle Hudson as he unpacks the elements of risk, curiosity, and problem-solving in entrepreneurship with Andy Budd, and discover how you can tap into the design world to inspire your own business journey.

Whether you're a current founder or someone just starting out, this episode has something for everyone who aspires to grow and innovate in today's fast-paced environment.

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Episode Stack: https://stackl.ist/41VfkDh

Kyle sits down with the inspiring young entrepreneur, Erifili Gounari. Starting as a digital-savvy Gen Z, Erifili turned her passion for building online communities into a groundbreaking venture—a social media agency called the Z Link, aimed at bridging the gap between brands and Gen Z consumers.

At just 19, she navigated the challenges of university, part-time jobs, and launching a business, ultimately making it onto the Forbes 30 under 30 list. Kyle and Erifili dive into the origin story of the Z Link, the significance of authenticity in marketing to Gen Z, and how content creation and entrepreneurial drive propelled Erifili's journey from a hobbyist to a successful founder.

Whether you're a budding entrepreneur or just fascinated by the dynamics of Gen Z marketing, this conversation is packed with insightful perspectives and actionable advice. Tune in for an engaging chat that explores the intersection of creativity, innovation, and the ever-evolving landscape of digital marketing.