Episode Stack: https://stackl.ist/48R3vkY

Don't miss this episode. I loved this conversation with Stephen Messer, who co-founded LinkShare with his sister in the late 90s and sold it to Rakuten after about 10 years. He's now building Collective[i], an AI platform that makes your professional network actually usable.

Stephen walked me through the first four years of LinkShare when they lived in one apartment, rotated shifts on two computers, and he worked directly on the main server because they couldn't afford another machine. During their pitches they had to spend first hour explaining what the internet was before they could even talk about the business. Revenue didn't grow until year six or seven because they charged 2% per transaction and needed massive volume.

One of my favorite stories: Michael Dell called him on a Sunday night and Stephen thought it was a prank for 30 minutes. That partnership changed everything. The first retailers all said "call us when you have affiliates," but direct marketers like Omaha Steaks understood the model from catalog days and signed up first.

Stephen was honest about why the skills from one successful company don't always transfer to the next one, why venture capital from top-tier firms isn't always worth the price, and his one rule for founders: never live above the second floor because the emotional swings will make you want to jump out the window at some point.

His take on most startup advice: ignore it and find your own style. Really appreciated Stephen's time and honesty about what building actually looks like.

Episode Stack: https://stackl.ist/3XlwM1O

I met Tracy in Hawaii when we were midway through our Blue Startups accelerator program. Tracy coaches founders, and also serves as a Mentor in the Blue Startups program.

Tracy came in and told such authentic (both inspiring and difficult) founder stories. We connected after and was thrilled she agreed to join us on Zero to Umm to tell some of those stores.. and more.

Tracy is the Co-founder and former CEO of Chewse, a corporate catering platform she launched from her dorm room, raised $40M for, and successfully sold in 2020. She now serves as an executive coach for founders, helping them navigate the intersection of leadership, mental health, and personal growth.

No matter what stage of the journey you're in, there's something valuable for you in this episode.

Takeaways

• Authenticity is crucial in fundraising.
• Building a startup is an emotional journey.
• Resilience is key to overcoming challenges.
• Staying true to oneself leads to success.
• The importance of a supportive team.
• Navigating the ups and downs of entrepreneurship.
• The role of personal growth in business success.
• Balancing personal and professional life.
• The impact of mentorship and guidance.
• Embracing change and transformation.

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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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Wrapping up the first season of Zero to Umm, I’m taking a moment to look back on the year—what worked, what didn’t, and some of the biggest lessons along the way. Just a casual reflection to close things out.

Thanks for listening and being part of it all!

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What is this? What does the title of this podcast even mean? What is a Stacklist?

All these questions, and more, will be answered in this very short five minute introduction. I look forward to a long and wonderful journey of interviewing founders and entrepreneurs to understand how they started and grew a company from idea into reality.

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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/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.