YesAnd
Roadmap to Nowhere
Roadmap to Nowhere is a podcast where product leaders Gustavo Smidt and Chris Wallace explore the chaos of building startups, products, and careers in tech. Each week we dive into AI, product management, entrepreneurship, and innovation—plus stories from the trenches every founder can relate to. Gustavo is the founder of Cloutfit.ai (https://cloutfit.ai/) and OutfitAlliance.com (https://outfitalliance.com/), AI platforms connecting influencers with fashion e-commerce brands. Chris is the founder of YesAnd (https://yesandlearntransformbuild.com/), helping leaders and teams grow through improvi
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Episodes
Turning Content Into Signups: AI Tools That Deliver 02.10.2025 48:43
In this episode of Roadmap to Nowhere , Gus and Chris unpack the AI tools that actually move the needle. From turning one long recording into dozens of Shorts, to driving influencer signups and replacing clunky BI dashboards with chat-based analytics, this conversation is full of practical takeaways for product managers, founders, and growth leads. You’ll learn how to: • Clip and schedule Shorts t...
10 Startup Ideas in 1 Episode — You Help Us Choose What to Build 22.05.2025 25:50
In this episode of Roadmap to Nowhere , Chris, Stu, and Gus pitch 10 completely unplanned startup ideas — from AI-generated greeting cards to emotional dashboards for teams. The twist? You get to vote on which one we should actually build next. Inside: AI-generated content tools and reporting systems Kids’ art turned into animated videos Backlog grooming, product chaos, and accidental insights Tan...
Clickbait, AI, and the Harsh Truth About Startup Marketing 19.05.2025 1:01:32
In this episode of Roadmap to Nowhere , Chris, Gus, and growth expert Nelio Leone dive into what happens after you build the product—how to actually get people to care. They talk: Why “build it and they will come” is a lie How to use AI tools to scale content and automate outreach The good, bad, and useful sides of clickbait Finding niche audiences and leveraging influencers Turning audience pain...
Affiliate Dreams and UX Nightmares: Building Health Apps with AI 08.05.2025 1:05:45
In this episode of Roadmap to Nowhere , Chris, Gus, and guest Nina Zahr (15+ years in healthcare product design) dive into the messy reality of building health products that actually work. From engaging quiz flows to smart affiliate strategies, they break down what keeps users coming back — and what sends them running. Topics include: • AI-powered personalization that doesn’t feel generic • Avoidi...
We Accidentally Built a Wellness Startup Using AI (Live on the Pod) 08.05.2025 1:03:37
In this episode of Roadmap to Nowhere , Chris, Gus, and Stu set out to fix the supplement industry using AI… and accidentally launch a wellness startup. Meet Fount.fit — a personalized supplement app built during the recording, using OpenAI, caffeine, and questionable confidence. We cover: Why supplement advice is broken (and still stuck in 2009) How AI helped us build smarter health recs on the f...
Building a Startup (Again), AI Marketing, and Pre-Dad Panic with Mahmoud Nessim 21.04.2025 1:05:46
Chris and Gustavo are back with another live startup build—this time joined by Mahmoud Nessim , an SEO expert turned growth founder, who’s also about to become a dad. No pressure. They talk about launching a profitable marketing business without a big team, using AI tools for content and research, and how SEO is evolving in real-time. Somewhere between AI-driven strategies and baby prep anxiety, a...
From Idea to Startup in One Episode: Building ‘Clothes Loop’ with AI 09.04.2025 1:29:15
In this premiere episode of Roadmap to Nowhere , Chris and Gustavo do what any reasonable people would do when faced with a podcast mic and no adult supervision: they start a company on air . The startup? Clothes Loop —a noble (and slightly chaotic) attempt to rescue abandoned outfits from closet purgatory and give them a second shot at life. Using AI tools , market data, and way too much optimism...
Welcome to Roadmap to Nowhere! 26.03.2025 14:34
Episode 1: “Welcome to the Roadmap to Nowhere – Buckle Up!” In the chaotic world of startups and product management, who better to guide you than three guys who’ve seen (and built) it all… and lived to podcast about it? 🎙️ Join Chris Wallace, Gustavo Smidt and Stuart Shapley—three seasoned product veterans with battle scars, big ideas, and a dangerously sharp sense of humor—as they kick off the Ro...
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