Zero to Umm...

Kyle Hudson

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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.

-5 ДН.

Steven Plappert - Forecastr

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 accident at a CFO shop in Louisville, and building Forecastr through six years of round-to-round survival. Key topics: Why curiosity, a greatness obsession, and a high tolerance for volatility pointed Steven toward entrepreneurshipThe FantasyHub shutdown that paid him $12,000 a year for two years — and the identity crisis that followed2,000 miles on the Appalachian Trail and the idea that wouldn't stop nagging him while he walkedThe second-time founder playbook: why Steven never raised without a paycheck and never dropped below three months of runwayHell Week at Christmas 2020 — four people hand-migrating 100 Google Sheets models into the new productThe Series A that died when Silicon Valley Bank didHis Iron Man suit philosophy: why Forecastr is building for a human in the loop, not against one

1 ч.
15 АПР.

Thomas Peham - Otterly.ai

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 — from the aha moment in his car to a Product Hunt launch with no pricing, a TechCrunch feature before Christmas, and scaling to 20,000 users in a single year without taking VC money. Key topics: Growing up in Austria with no business background and stumbling into SEO through HTML hobby projectsBuilding Usersnap's inbound engine from zero marketing budget to seven figures through content aloneThe moment he realized AI search was going to disrupt everything he'd spent years masteringLaunching on Product Hunt with a "super scrappy" product and no pricing pageWhy 15% of website traffic now comes from AI agents — and what that means for marketersBootstrapping a 17-person company in a category that didn't exist two years ago

50 мин.
17 МАР.

Andrew Boos - Darwinian Ventures

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 about, learned enterprise sales under a CRO with a $4.2 billion annual quota at a Sutter Hill incubation, blew his exit money trying to launch a quantitative hedge fund, and started freelancing to pay rent when law firms came knocking. We talk about why a linear path to entrepreneurship is a privilege, what happens when your North Star disappears after an exit, how he built Darwinian from a solo 1099 gig into an embedded sales team that's worked with 100+ startups, and why he's now writing small checks into companies where he can see product-market fit before the founders do.

52 мин.
2 МАР.

Michael Hoy - Atlas

🔗 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 humbling realization that 1,200 users didn't translate into a single paying customer. We talk about why the startup advice machine creates more noise than clarity, how AI is shifting from exciting to existential, and why the founders who win are the ones who learn to trust their own signal over everyone else's opinions. We also get into Michael's vision for where Atlas is headed: a trust layer for the coming agent-to-agent economy, and why that future might be closer than most people think. Topics we cover: Why this month felt like AI truly woke up.Building 12 projects in a week and what that means for everyone else. The gap between Product Hunt traction and real product-market fit. Education-based marketing that leads with curiosity, not fear. Doing things that don't scale on purpose. Michael's advice to founders: trust what you're feeling and shut out the noise.

1 ч. 1 мин.
17 ФЕВР.

Nicole Miranda - 6 Degree Soul

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 sales job - Manifesting Miss Hawaii with Dr. Joe Dispenza - Building Six Degree Soul (tours + retreats) - Upcoming events in Oahu (August) and Bali (October) - Why "follow your passion" misses the point For anyone stuck in a "good" job that's killing them.

41 мин.
7 ЯНВ.

Vlad Cazacu - Flowlie

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 startup in college, turning down an acquisition offer because it did not feel big enough at the time. That early mix of curiosity, naivety, and ambition shows up again and again in his story. Vlad spent years on the investing side, working in venture capital and family offices, seeing thousands of deals and learning how capital actually moves. Flowlie did not start as a founder product at all. It began as an internal tool for investors, then pivoted after founders started asking a simple question: “Are we even a good fit for these investors?” We talk about the shoebox office in Miami, the moment Stripe lit up with their first paid users, why fundraising is mostly unnecessary overhead, and how AI should remove friction instead of adding noise. This is a true zero-to-something story, told while still very much in motion. Key moments we cover: Growing up in Romania and falling in love with building through curiosityBuilding and shutting down a college startup after turning down an acquisitionWriting a book before ChatGPT and how it unlocked a VC careerWhy Flowlie started as an investor tool and pivoted to foundersThe first Stripe notification that made everything feel realA future where founders only show up for investor meetings Key takeaways: Naivety is often a feature, not a bug, in early foundersFundraising is a system problem, not a confidence problemThe right tool removes emotional and cognitive overhead Chapters 00:00 The Naivety of Startup Beginnings 03:03 The Journey to Entrepreneurship 06:07 The Birth of Barter Out 09:01 The Influence of Family and Curiosity 12:04 Lessons from Early Ventures 14:55 Transitioning to Venture Capital 17:58 Building Flowlie: The Next Chapter 22:57 The Pivot to Founders' Needs 30:00 Building the Team and Culture 37:05 Funding Journey and Growth 38:13 Future Vision and AI Integration

1 мин.
15.12.2025

Stephen Messer - Collective[i]

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.

1 ч. 1 мин.
27.11.2025

Tracy Lawrence - Chewse

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. TakeawaysAuthenticity 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.

56 мин.

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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.

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Kyle Hudson
Годы выхода

2024 - 2026
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37
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© 2025 Kyle Hudson
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Zero to Umm...