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Startups Decoded

Andy Walsh
Startups Decoded
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  • S2E8: Founders: The Easy Way to Land Angels, Fast - Jaclyn Johnson, CEO - Cherub
    Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.Subscribe nowIn this conversation, we break down:Jaclyn’s origin story: why she built CherubHow she approaches angel investing and the lessons she’s learnedWhat makes a great angel pitch (and what doesn’t)The realities of being an accredited investorWhy representation in funding isn’t just moral, it’s market-changingChapters00:00 The Importance of Angel Investments02:49 Jaclyn’s Journey as a Founder and Investor05:41 Understanding Angel Investors vs. Venture Capitalists08:28 The Role of Angel Advisors11:23 Building Relationships with Angels14:15 The Power of Brand Fame17:25 Cherub’s Mission and Deal Flow20:07 Educating Angels and Standardizing Investments23:13 Creating Effective Fundraising Pages26:12 The Role of Analytics in Fundraising29:04 Onboarding Founders to Cherub32:01 Connecting with Angels: Best Practices35:03 Diversifying the Investment Landscape37:58 The Future of Angel Investing40:35 Special Offers for Founders on CherubGuest BioJaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.Who Should ListenFounders raising their first angel roundEntrepreneurs seeking representation and resourcesPeople curious about Angel Investing and how to get startedOperators looking to understand the angel landscapeMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
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  • S2E7: Boards That Raise, How to Turn Advisors into Capital (with Breen Sullivan)
    What if founders could get the right advisor, investor, or board talent exactly when they need it, before they even ask?In this episode, Breen Sullivan (Founder & CEO, The Fourth Effect; longtime startup GC and board leader) lays out how AI is changing founder access: surfacing who you need and when, structuring “fit-for-purpose” advisory and board relationships, and turning connections into outcomes.We unpack why traditional networks leave too many founders behind, how to make boards growth drivers (not just governance), and how smarter, dynamic advisory models can lift retention, capital access, and founder resilience.Chapters00:00 Introduction to Boards and Advisories02:49 The Role of Community in Startups05:33 Understanding Advisory Boards08:12 The Impact of AI on Advisory Boards11:05 Fit for Purpose: Dynamic Advisory Relationships14:03 Navigating Advisor Roles and Responsibilities16:27 The Importance of Early Advisory Engagement19:32 Leveraging Advisors for Fundraising22:15 The Fourth Effect Platform Overview24:58 Connecting Founders with Advisors27:42 The Future of Advisory Boards and Capital RaisingBreen SullivanBreen Sullivan is Founder & CEO of The Fourth Effect and a seasoned startup executive, board member, and former General Counsel across high-growth companies. She focuses on building inclusive, ROI-driven boards and advisory networks that strengthen execution, fundraising, and leadership. She’s a leading voice on board diversity, founder access, and equitable innovation.The Fourth EffectWho Should ListenFounders building advisory benches and early boardsOperators/execs considering advisor or independent director rolesAngels and VCs exploring advisor-investor modelsBuilders designing AI-assisted founder support workflowsMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All AreasListen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
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  • S2E6: AI Meets Medicine — Personalized Care You’ll Actually Use with Dr. Erik Reis
    How integrative care, AI, and behavior design are reshaping health: prevention-first, data you own, and systems busy founders can stick to.Founders are optimizing everything, except their health. Quick fixes don’t scale, and siloed care leaves people guessing.In this episode, Dr. Erik Reis, Co-Founder & Director of Health & Wellness at Nobody Studios and founder of The Neural Connection, maps a practical path to holistic, evidence-based wellness. We cover prevention vs. reaction, integrating Eastern + Western approaches, what data you should actually track, and how startups can build credible wellness products without the hype. If you’re building or buying health tech, or just trying to perform at a high level, this is your playbook.If you’re a founder, operator, or investor in health, performance, or longevity, this one’s for you.Subscribe nowchapter titles00:00 Introduction to Holistic Health and Medicine01:20 Dr. Erik’s Journey into Healthcare03:43 The Role of Technology in Healthcare09:29 The Importance of Preventative Care12:39 Integrating Eastern and Western Medicine16:51 Empowering Patients through Technology20:59 Behavioral Change in Health Management23:51 The Influence of Genetics and Lifestyle on Health25:36 Harnessing Technology for Health Management27:54 The Role of Data in Healthcare29:37 Collaboration and Innovation in Healthcare31:29 The Basics of Longevity and Health33:42 The Future of Startups in Health and WellnessDr. Erik ReisCo-Founder & Director of Health & Wellness, Nobody Studios; Founder, The Neural Connection (integrative neuro clinic). Erik specializes in complex neuro cases and scalable wellness systems that blend traditional therapies, modern neuroscience, and practical behavior design. His through-line: teach people to own their data, build prevention into daily life, and use tech to amplify, not replace, human care.Connect with Dr. Erik Reis:Nobody StudiosThe Neural Connection ClinicDr. Erik Reis - LinkedInWho should listenSeed–Series B founders optimizing health/performanceHealthtech builders aiming for evidence-based productsOperators/investors evaluating prevention and longevity playsMusic Credit: “Neptuno” - Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
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  • S2E5: How AI Agents Ran Our Business, While I Went To Burning Man (with Adam Robinson)
    OpenAI’s latest “Zapier-killer” headlines were sobering, but Adam Robinson already did the unthinkable: he removed every human from RB2B, a $6M ARR SaaS, for seven days and let AI agents run sales, support, and onboarding, zero intervention.The outcome?Revenue growth held (+4%/mo), 96.6% answer accuracy in sales chats, and 89% support resolution with no customer meltdowns.In this conversation, Adam unpacks:The real playbook behind the stuntWhy he designs his business to fit AI tools (not the other way around)How great documentation and Intercom Fin “guidance” drive resolution,Where agent workflows replace repetitive tickets,Why he’s doubling down on PLG, freemium, and simplicity, even in a high-churn category.We get into transparency, customer expectations, and why a profitable, small team can now beat over-tooled incumbents.Also: Yes, the week he “disappeared,” Adam was off-grid at Burning Man.Subscribe nowChapters00:00 Why agents now (and the OpenAI “Zapier-killer” moment)02:06 From Lehman Brothers to bootstrapped SaaS operator04:56 The 7-day no-humans experiment: scope & safeguards09:07 Build-to-AI: shaping product so agents can handle the work12:50 Lean, profitable, small: the appeal of a high-margin micro-org17:35 Adapting process to tools (not tools to process)23:06 Intercom Fin “guidance,” escalations, and transparency25:44 Churn reality: category dynamics and buyer persona30:10 Agent workflows: auto-diagnosing email invites (SendGrid)34:05 Feedback loops: weekly founder calls and customer insights39:19 Human connection vs. agent efficiency in 202542:33 Embracing imperfection—and why “simple wins”Guest BioAdam Robinson is Founder & CEO of Retention.com and RB2B. He bootstrapped Retention.com from $0 to $22M ARR in four years and previously built Robly to an eight-figure exit. A former CDS trader at Lehman Brothers/Barclays, he now builds lean, profitable SaaS—and publishes the receipts.Who Should ListenSaaS founders optimizing for profitability over headcountOperators implementing AI in sales, support, and onboardingInvestors tracking agentic automation and PLG at scaleBuilders designing “self-running” products and processesMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.comStartups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
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  • S2E4: The Startup Security Playbook: AI That Keeps Up with AI — with Francesco Piccoli (Almanax).
    Send us a textHow LLMs are rewriting application security: less false positives, faster triage, and real-world founder playbooks.Founders are sprinting on AI—attackers are too. Traditional security tools drown teams in alerts and miss the real threats. In this episode, Almanax founder & CEO Francesco Piccoli breaks down AI-native application security: how LLMs detect logic bugs legacy scanners miss, cut up to 90% of noise, and triage vulnerabilities at the pace you ship. We cover where “shift-left” falls short, how to operationalize low-friction code scanning in GitHub, and what legal/compliance leaders expect before they’ll sign your deal.If you’re building or buying AI-accelerated software as a founder, CTO, or security lead, this is the playbook.Chapters00:00 AI-Native Security: Why It Matters Now01:19 Francesco’s Path to AppSec05:26 Why Legacy Tools Miss Real Bugs10:48 The Cat-and-Mouse Reality of Cyber15:46 Legal & Compliance: What Founders Owe20:34 Founder Best Practices (Week-1 Checklist)28:46 Cutting 90% of Alert Noise36:32 Making Security Usable for Devs39:45 When Breaches Happen: First Calls41:53 Wrap-Up + Next StepsFrancesco PiccoliFounder and CEO of Almanax, joins us to unpack how his team is building AI-native systems to catch 5x more bugs while cutting 90% of the noise. We talk about the future of application security, why shift-left isn’t enough anymore, and how triaging vulnerabilities at scale requires a new kind of intelligence.Who Should ListenSeed–Series B founders shipping fast on AI-native stacksEng leaders drowning in SAST/DAST false positivesSecurity & compliance owners prepping for SOC 2 / ISO 27001Music Credit: "Neptuno" - Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: Need clarity on fundraising, strategy, or scaling? You can book me, Andy Walsh, directly on Hubble for focused 1:1 advice. 15, 30, or 45 minutes no fluff, just solutions.Head to hubble.social/AndyWalshDiscover Smarter Investing with the Teaminvest Wealth Builders PodcastExpert insights and proven strategies from Australia's top investors. Build your wealth.Listen on: Apple Podcasts SpotifySupport the show
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About Startups Decoded

Startups Decoded is a podcast that provides real-world insights into startup strategy and growth, featuring expert-led content, insider stories, and actionable takeaways for founders and investors. We bridge the gap between theory and practice, offering practical lessons to help entrepreneurs thrive in today’s fast-paced ecosystem. More than just a podcast, it's a resource for innovators who dive deep into the strategies behind building and scaling successful startups.
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