Roadmap to Nowhere

PODCAST · business

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

  1. 8

    Turning Content Into Signups: AI Tools That Deliver

    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 that get discovered• Track signups and conversions with lightweight attribution• Capture and organize ideas using AI note-taking• Build small products that generate long-tail revenueWe also dive into tools like Opus Clips, Riverside, TikTok Ads, Metabase MCP, Manus, Perplexity Comet, and Suno — and how they fit into a modern creator and startup stack.

  2. 7

    10 Startup Ideas in 1 Episode — You Help Us Choose What to Build

    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 systemsKids’ art turned into animated videosBacklog grooming, product chaos, and accidental insightsTangible products in a digital worldWhy audience-first ideas always winIt’s messy. It’s funny. It might accidentally lead to our next company.#StartupIdeas #BuildInPublic #ProductManagement #StartupPodcast #RoadmapToNowhere

  3. 6

    Clickbait, AI, and the Harsh Truth About Startup Marketing

    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 lieHow to use AI tools to scale content and automate outreachThe good, bad, and useful sides of clickbaitFinding niche audiences and leveraging influencersTurning audience pain points into real tractionIf you’re stuck between a finished product and zero users, this one’s for you.

  4. 5

    Affiliate Dreams and UX Nightmares: Building Health Apps with AI

    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• Avoiding the most common UX drop-off traps• How to make affiliate links not feel scammy• Influencer outreach without the cringe• Teaching AI like it’s a confused intern (because it kind of is)A must-listen if you’re building in wellness, UX, or trying to make money without ruining the experience.

  5. 4

    We Accidentally Built a Wellness Startup Using AI (Live on the Pod)

    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 flyThe naming, branding, and monetization chaos behind Fount.fitWhether this is a real company or a very convincing bitSurprisingly useful. Definitely unplanned. Very us.

  6. 3

    Building a Startup (Again), AI Marketing, and Pre-Dad Panic with Mahmoud Nessim

    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 new business idea is born—again.Expect real talk on:Startup growth without adsBuilding tools for overwhelmed new parentsProgrammatic SEO and smart traffic strategiesAI as your research intern (minus the attitude)Oh, and yes, they try to build another company mid-episode. Because of course they do.

  7. 2

    From Idea to Startup in One Episode: Building ‘Clothes Loop’ with AI

    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, they prototype a Minimum Viable Product (MVP) live during the episode.They explore the booming world of secondhand fashion, question their own business model in real-time, and prove that yes—you can build a startup in a single podcast episode (but should you? remains TBD).Highlights include:AI doing the heavy lifting while Chris and Gustavo take creditNaming a startup in under 3 minutes (without regrets… mostly)The joys and tears of live prototypingReal-time UX feedback that hits harder than expectedSolid startup advice accidentally mixed with sarcasmWhether you’re a founder, fashion lover, AI enthusiast, or just here for the chaos, this episode kicks off a startup journey that’s as insightful as it is unhinged.

  8. 1

    Welcome to Roadmap to Nowhere!

    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 Roadmap to Nowhere.In this very first episode, we unpack: • What this podcast is really about (spoiler: it’s not just another “how to build a unicorn” show) • Why roadmaps are a lie we lovingly tell ourselves • Our worst product launch stories (yes, there were tears) • And how to survive—and maybe even thrive—in the madness of building products people actually want.If you’re a founder, product manager, designer, or just someone who’s had a meeting that could’ve been a meme, this is your new favorite show. Expect honest takes, zero buzzword BS, and lots of laughs.

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ABOUT THIS SHOW

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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