Zero to Umm...
Dive into the raw, unfiltered journey of startup founders and CEOs as they navigate the tumultuous waters of entrepreneurship. "Zero to Umm..." flips the script on typical success stories, focusing instead on the pivotal moments of uncertainty, fear, and adaptation that truly define a startup's path.
Episodes
Episode stack: https://stackl.ist/4baJeZm
We taught computers to do math, then to write. Jared White thinks the real unlock is teaching them to read, and he's proving it in the one place that punishes a wrong answer hardest: the courtroom.
Kyle sits down with Jared, founder and CEO of Matey AI, whose path runs from building quantitative trading desks in Austin, through a stint in crypto, to an AI-native legal company built fo...
Episode Stack: https://stackl.ist/3SkDnKG
My podcast guest couldn't make it today. So I figured I'd just tell you where we're at.
What came out was probably the most honest version of the Stacklist vision I've said out loud: why the internet has been broken since 1995, why your website and Instagram and LinkedIn are all symptoms of the same problem, and what we're actually building to fix it.
No deck. No script. Just 9 years o...
Episode Stack: https://stackl.ist/4vWPzAl
You've heard the pitch: AI agents that run your marketing, write your content, manage your ads, source your leads. It sounds like science fiction, or at minimum, like something that works for someone else's company. Cody Schneider has actually built it. In this episode, Cody, co-founder of Graphed, former growth lead at Rupa Health, and serial builder from Coeur d'Alene, Idaho &mdash...
Episode Stack: https://stackl.ist/4tqYPeB
Steven Plappert closed Forecastr's Series A the day before his last payroll would have cleared the bank. Six weeks later, he's sleeping eight hours a night for the first time as a founder.
In this episode of Zero to Umm, Steven and I trace the full arc: failing his first company after three years, walking the Appalachian Trail from Georgia to Maine, meeting his co-founder Logan Burchett by ac...
Episode Stack: https://stackl.ist/3QEYaYe
Thomas Peham spent a decade building marketing engines for other people's companies — from a tiny PLG startup to a venture-backed company that raised $138M in funding. Then he noticed something that changed everything: ChatGPT was answering questions his clients used to win on Google, and nobody had a way to measure it.
In this episode, Thomas shares the full story behind Otterly AI &md...
Episode Stack: https://stackl.ist/4sSOZBB
Andrew Boos is the founder of Darwinian Ventures, a fractional sales advisory firm that builds go-to-market teams for early-stage B2B startups. He's also quietly investing in his own clients from profit, not a fund.
Before Darwinian, Andrew had a profitable exit at 24 from a startup that began as an ad exchange for China (yes, really), fell into post-exit depression nobody wanted to hear abou...
🔗 Episode Stack: Link on Stacklist
AI is moving so fast that it's hard to know what to pay attention to and what to tune out. In this episode, Michael Hoy (co-founder and CEO of Atlas) and I dig into what it feels like to build a company during the most disorienting moment in tech most of us have ever experienced.
Michael shares the full Atlas origin story, from winning Product Hunt's product of the day, week, and month, to the humb...
Episode Stack: https://stackl.ist/4rYFAYM
8 years in corporate sales. One birthday trip to Hawaii. Quit mid-vacation. Became Miss Hawaii 2025. Built a retreat business.
All in 24 months.
Nicole Miranda's timeline sounds impossible. It's not.
This episode is about what happens when you stop optimizing for other people's definitions of success and start trusting that you're on the right river.
We covered:
- The moment she quit her sal...
Episode Stack: https://stackl.ist/4qaixcK
Summary
In this episode I sit down with Vlad Cazacu, Founder and CEO of Flowlie, to talk about the long, winding path that led him from an immigrant kid obsessed with science magazines to building one of the most thoughtful fundraising tools I’ve used as a founder.
We go way back. Before Flowlie was helping founders raise hundreds of millions of dollars, Vlad was running a textbook start...
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 com...
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...
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 p...
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 emphasize...
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,...
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...
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...
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 rem...
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 ...
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,...
Episode Stack: https://stackl.ist/3QPuHaW
Ever wondered how creativity meets entrepreneurship? Dive into this conversation with Kyle Hudson and Will Taylor on "Zero to Umm..." where they chat about Will's journey from a physicist in a creative family to launching startups.
Get ready for some raw insights as Will reveals his experiences with a CV writing service, on-demand dry cleaning, and solving logistics with tech-dr...
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