/Startups Decoded

Startups Decoded

Startup investing used to be gated, exclusive networks, complex diligence, and full-time fund managers. But what if anyone could build a startup portfolio the same way they’d shop online?In this episode, Cheryl Kellond, serial founder and CEO of Play Money, shares how her platform is democratizing early-stage investing by pairing curated deals from new fund managers with an experience that feels more like shopping than finance. We dive into her journey from launching Bia Sport and Apostrophe (acquired by Centivo) to building Play Money, the new “fantasy league” for startup investing.Expect a candid lesson on why making startup capital more inclusive can reshape who gets funded and who gets to build wealth.Subscribe nowChapters00:00 Introduction to Play Money and Its Mission04:37 The Challenges of Accessing Capital11:21 The Evolution of Early Stage Investing16:59 Understanding the Angel Investment Landscape22:30 The Role of Education in Angel Investing28:20 The Founder Experience on Play Money33:49 Building Trust and Validation in Startups39:27 The Future Vision for Play MoneyCheryl KellondFounder & CEO of Play Money, is a concept-to-launch expert who has driven $750M+ in revenue from healthtech, SaaS, hardware, and media products. She previously founded Apostrophe (Techstars ’17, acquired by Centivo) and Bia Sport (Lemnos ’12), and has launched major products at Adobe, Yahoo, and E*TRADE. Voted Denver’s Most Admired CEO and a 40 Over 40 honoree, she’s passionate about disrupting legacy industries and building founder-friendly ecosystems.Who Should ListenAspiring angel investors who want a smarter, accessible entry pointFounders curious about new funding pathwaysEmerging fund managers building their first LP baseAnyone interested in wealth-building through startups without “full-time VC” complexityMusic 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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S2E15: We Need To Scale Angel Investing — with Cheryl Kellond, Play Money.

Dec 22, 2025·—

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S2E14: When AI Chases Invoices Better Than You Do – Mihir Deo, Founder - Invoice Butler.

Dec 15, 2025·—

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As AI moves from clever tool to “virtual teammate,” nowhere is the shift more real than in finance. In this episode of Startups Decoded, Invoice Butler founder & CEO Mihir Deo joins Andy Walsh to explore what happens...

S2E13: From Fundraise to Exit: What Every Founder Needs to Know — Jennifer Lewis, Exited Founder - Lex

Dec 8, 2025·—

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In this episode, Andy Walsh sits down with Jennifer Lewis, former Founder CEO of queer social app Lex, to unpack the full arc from first fundraise to exit. Jennifer shares what really happens behind the scenes when...

S2E12: There Is No Perfect Pitch Deck - What You Actually Need, with Robert Harary, CEO and VC - Decko

Dec 1, 2025·—

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Robert Harary found his first venture deal while in high school detention, and hasn’t looked back since. Today, he sits at the center of the venture ecosystem as both an investor and founder, with a decade-plus...

S2E11: Use Banks, Not VCs: Non-Dilutive Capital for Founders with Ashley D. Bell & Redemption Bank.

Nov 24, 2025·—

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Attorney, entrepreneur, and policy leader Ashley D. Bell is building Redemption Bank, a modern Minority Depository Institution designed to give founders something Silicon Valley rarely does: non-dilutive capital that...

S2E10: The FemTech Edge: Build and Train by Your Menstrual Cycle - Lizzy Palmer (Founder, SyncN).

Nov 17, 2025·—

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94 percent of sports-science research excludes female physiology. The result? A $10 billion fitness industry that burns women out, leads to injury, and disrupts hormonal health. Lizzy Palmer, Founder and CEO of SyncN...

S2E9: From Peter Thiel’s Fellowship to 1517 Fund — The VC Who Funds Rebels (Michael Gibson)

Nov 10, 2025·—

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Forget Ivy League. Build Your Own Startup Empire. From Peter Thiel’s Fellowship revolution to building the 1517 Fund, Michael Gibson has made a career out of betting on outsiders. In this episode, he reveals how Thiel’s...

S2E8: Founders: The Easy Way to Land Angels, Fast - Jaclyn Johnson, CEO - Cherub

Nov 3, 2025·—

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J aclyn 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...

S2E7: Boards That Raise, How to Turn Advisors into Capital (with Breen Sullivan)

Oct 27, 2025·—

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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...

S2E6: AI Meets Medicine — Personalized Care You’ll Actually Use with Dr. Erik Reis

Oct 20, 2025·—

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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...

S2E5: How AI Agents Ran Our Business, While I Went To Burning Man (with Adam Robinson)

Oct 13, 2025·—

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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...

S2E4: The Startup Security Playbook: AI That Keeps Up with AI — with Francesco Piccoli (Almanax).

Oct 6, 2025·—

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Send us a text How 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...

S2E3: Crack the LinkedIn Code: How to Hit 100,000 Followers with Charlie Hills

Sep 29, 2025·—

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Send us a text In this episode of Startups Decoded, Andy Walsh talks with Charlie Hills, a global leader in LinkedIn growth strategy. AI is rewriting LinkedIn, and Charlie Hills has the receipts. In 466 days, he went...

S2E2: Own the Audience or Lose the Game. Nick Humphreys - Linktree.

Sep 22, 2025·—

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Send us a text Algorithms are wringing creators dry. In this inspiring S2 episode, Linktree co-founder & CCO Nick Humphreys ($167M raised; 70M+ users) lays out the new playbook: AI that amplifies your voice, owning your...

S2E1: How Billion-Dollar Companies Get Built. Mike Jones - Liquid Death, Dollar Shave Club, Science Inc.

Sep 14, 2025·—

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Send us a text In the Season 2 opener of Startups Decoded, host Andy Walsh sits down with Mike Jones, General Partner at Science Inc., the venture studio and fund behind household names like Dollar Shave Club, Liquid...

Ep#33: The Real Cost of Venture Capital in the AI Era - Joseph Lee.

Sep 8, 2025·—

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Send us a text In this episode of Startups Decoded, I sit down with Joseph Lee, founder and CEO of Supademo, to talk about the real founder’s journey behind raising capital and the tradeoffs that come with it. Joseph...

Ep#32: A Logo is Decoration. A Brand Is Survival. Startups Fail When They Ignore It. With Malcolm Buick.

Sep 1, 2025·—

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Send us a text In this episode of Startups Decoded, host Andy Walsh sits down with Malcolm Buick, Partner & Chief Creative Officer at Athletics and a seasoned creative director, to unpack how design drives startup...

Ep#31: Your Digital Strategy Is Already Obsolete! Here’s How to Fix It with Jay Erickson.

Aug 25, 2025·—

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Send us a text In this episode of Startups Decoded, Andy Walsh sits down with Jay Erickson, Chief Innovation Officer and co-founder of Modus, to explore why most digital strategies are already outdated, and how to fix...

Ep#30: Future-Proofing Products in 2025: Startup Lessons from Orgo’s Zoya Lehrer

Aug 17, 2025·—

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Send us a text Summary In this episode of Startups Decoded, host Andy Walsh speaks with Zoya Lehrer, founder of Orgo, about the challenges and opportunities in the startup landscape, particularly in the realm of product...

Ep#29: The Post-Product Market Fit Playbook: Scaling, Systems, and Survival - with Adrian Fagerlund - Linkby

Aug 11, 2025·—

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Send us a text In this episode of Startups Decoded, Andy Walsh sits down with Adrian Fagerlund, Co-Founder and CRO of Linkby, a performance PR platform connecting advertisers with premium publishers. They explore...

Ep#28: How Great Founders Build Trust: The Startup Advantage You Can’t Fake - David Homan

Aug 4, 2025·—

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Send us a text Most startup advice focuses on product, pitch, and traction. But there’s one skill that fuels them all: trusted relationships. In this episode of Startups Decoded, Andy Walsh sits down with David R...

Ep#27: The Secret to Raising Capital? Tell Your Story, Don’t Sell - Dr. Ankur Pathak.

Jul 28, 2025·—

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Send us a text Discover how effective storytelling captivates investors and builds a compelling personal brand. Join us as we unpack the strategies founders and leaders use to craft narratives that drive investment and...

Ep#26: Why Your Startup’s Culture Sucks (and How to Fix It) - Michael Landers

Jul 21, 2025·—

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Send us a text In this episode of Startups Decoded, Michael Landers shares why culture isn’t just an HR function; it’s a startup’s competitive edge. We’ll explore how founders can intentionally shape company culture...

Ep#25: Scale or Shatter? Why Founders Break - Leila Lahbabi

Jul 14, 2025·—

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Send us a text Many founders are chasing scale, but at what cost? In this episode, Leila Lahbabi shares how purpose-driven leaders can grow thriving companies without burning out or losing themselves in the process. We...

Ep#24: Why Venture Studios Are the Future of Startups - Matthew Burris

Jul 7, 2025·—

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Send us a text Matthew Burris joins Startups Decoded to unpack how venture studios are evolving from a misunderstood startup model into a formal, fundable asset class. We explore what’s missing from today’s narrative...