Podcast
Angels Decoded
Hosted by Andy Walsh · EN
Writing a check is easy. Knowing why is the flex. Angel investing is underused, misunderstood, and explained badly. We are in cahoots with Play Money to deliver a raw take on the craft. Subscribe. Then decide.
22episodes
Episodes
Newest firstAll episodes
Ep#12: The Angel Advantage in Venture Capital’s “Black Hole"
May 100:20:28Tap to summarizeWhen venture capital chases the same handful of companies, opportunity doesn’t disappear. It moves.In Ep#12 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack the recent claim circulating on VC Twitter that every startup sector outside AI is a “black hole” for capital. Rather than seeing that as a warning, Cheryl argues it may be one of the most exciting moments for angel investors.As capital concentrates into a small number of mega deals, entire sectors are being overlooked. That creates what investors call arbitrage: the chance to invest in strong companies at lower valuations while clear exit paths still exist.This episode explores why angels operate under different incentives than venture capital funds, how capital concentration creates mispricing in the market, and why sectors like climate tech, consumer products, and women’s health may offer compelling opportunities right now.Topics covered: • Why venture capital is concentrating on a handful of AI deals • The structural difference between angels and VC funds • How market concentration creates arbitrage opportunities • Why entry valuation matters for investor returns • Sectors being overlooked despite strong exit potentialWhen capital crowds into the same deals, the smartest investors often look somewhere else.Sometimes the real opportunity is inside the so-called “black hole.”Listen: Apple | Spotify | YouTubeSubscribe nowAndy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comStartups Decoded Podcast: startupsdecoded.com
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Ep#11: The New Founder Playbook in the Age of AI
Apr 2400:14:36Tap to summarizeAI is changing how startups are built. It’s also changing what great founders look like.In Ep#11 of Angels Decoded, Cheryl Kellond and Andy Walsh explore why the traditional traits investors look for in founders may no longer be enough in the AI era.While grit, adaptability, and resourcefulness still matter, founders today face a new layer of responsibility: understanding how AI can remove friction, unlock new capabilities, and reshape how teams build and scale.This episode unpacks how AI is raising the ceiling for startups, why tinkering and experimentation are becoming core founder skills, and the questions investors should be asking to identify founders who can thrive in this new environment.Topics covered: • Founder traits in the age of AI • How AI changes startup building and scaling • Why “tinkering” is a new founder skill • The difference between hype and real AI advantage • Questions investors should ask founders about AIAI won’t magically create great founders.But it will amplify the ones who know how to use it.Listen: Apple | Spotify | YouTubeAndy Walsh 2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.com Startups Decoded Podcast - startupsdecoded.com
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Ep#10: The Echo Chamber Problem in Venture Capital
Apr 1700:17:13Tap to summarizeAngel investing, venture capital, startup funding — the rules of the market are changing.In Ep#10 of Angels Decoded, Cheryl Kellond and Andy Walsh break down why many traditional investors believe there are no new startup investors entering the market — and why that assumption may be completely wrong.With trillions of dollars expected to transfer to younger generations over the next decade, a new class of investors is emerging. Yet fewer than 5% of accredited investors currently participate in startup investing, leaving enormous room for growth.This episode explores how venture capital echo chambers form, why new investor markets are often ignored, and how platforms, universities, and generational wealth transfer are expanding access to angel investing.Topics covered: • Angel investing market opportunities • Generational wealth transfer and startup funding • Venture capital echo chambers • Democratization of startup investing • New investor models and platformsAngel investing is changing.The next wave of startup capital may come from investors the venture industry isn’t even looking at yet.Advice: Write the check.Listen: Apple | Spotify | YouTubeAndy Walsh - 2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl Kellond - Founder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.com ResourcesStartups Decoded Podcasthttps://startupsdecoded.com
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Ep#9: Building Your Own AI Investment Framework
Apr 900:15:20Tap to summarizeAI is changing how startups are built. It’s also changing how angel investors make decisions.In Ep#9 of Angels Decoded, Cheryl Kellond and Andy Walsh explore why traditional investment signals are breaking down in the age of AI. For years, angels could rely on signals from experienced funds, market momentum, or category expertise. But when AI is evolving this fast, even professional investors are navigating the same uncertainty.That shift means angels can no longer rely on borrowed conviction. Instead, they need their own framework for evaluating startups in a world where AI is becoming the default technology layer.This episode explores how investors can cut through the noise, what signals still matter, and why proprietary data may become the most valuable asset a startup can build.Topics covered: • Why traditional investment signals are becoming less reliable • How AI is shifting the way startups create competitive advantage • The difference between companies AI can replace and those AI strengthens • Why proprietary and evolving data may determine future startup value • How angel investors can build their own decision-making frameworkAngel investing has always involved uncertainty.In the age of AI, conviction matters even more.Advice: Build your own framework before writing the check.Listen: Apple | Spotify | YouTubeSubscribe nowAndy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comResourcesStartups Decoded Podcast
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Ep#8: The Emotional Cost of Optimism in Angel Investing
Apr 300:18:42Tap to summarizeAngel investing is often described as a financial decision. In reality, it’s an emotional one.In Ep#8 of Angels Decoded, Cheryl Kellond and Andy Walsh explore why many angel investors are hesitating right now. Not because the deals are worse, but because the emotional cost of optimism has suddenly become higher.Angel investing requires belief in founders, ideas, and a future that doesn’t exist yet. But when the world feels unstable, even experienced investors can find themselves pulling back.This episode explores why that hesitation happens, how uncertainty impacts capital deployment, and why staying engaged with founders may be more important than ever.Topics covered:• Why angel investing is fundamentally an act of optimism • The emotional impact of uncertainty on investment decisions • How stepping back from investing can slow innovation • The unexpected personal and professional benefits of writing early-stage checks • Why connecting with founders can reignite belief in the futureSometimes the best response to uncertainty is simple:Advice: Just write the damn check.Listen: Apple | Spotify | YouTubeAndy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.com ResourcesStartups Decoded Podcast: https://startupsdecoded.com
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Ep#7: Convertible Notes — Complex, Costly, and Mostly Unnecessary
Mar 2700:16:41Tap to summarizeConvertible notes were once the default way for startups to raise early-stage capital.But today, many founders and angels still use them without fully understanding how they actually work.In Ep#7 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack why convertible notes still exist, how they function, and why both founders and investors often misunderstand the real trade-offs.On paper, convertible notes look attractive. They include debt, interest, and a timeline for conversion into equity. That structure can make investors feel like they have something more “real” than a SAFE.But in practice, those features rarely deliver the benefits people expect.Debt in a pre-revenue startup rarely has real protection. Interest can create phantom income and tax headaches. And the maturity timelines almost always get extended rather than enforced.Meanwhile, convertible notes can introduce unnecessary pressure into founder relationships and create major administrative complexity when a priced round finally happens.This episode explores why convertible notes often solve problems that don’t really exist, while introducing new ones that founders and angels rarely anticipate.Subscribe nowWhat We Break DownConvertible notes are technically debtThey accrue interest and convert to equity later, but that debt rarely offers real protection in early-stage startups.Interest creates phantom incomeInvestors can end up paying taxes on interest that hasn’t actually produced cash.The timeline pressure is mostly artificialMost notes get extended rather than converted when the maturity date arrives.QSBS tax advantages can disappearBecause convertible notes are structured as debt, investors may lose early eligibility for Qualified Small Business Stock tax benefits.Administrative complexity explodesDifferent investors entering at different times create complicated calculations when notes convert into equity.The Big IdeaConvertible notes promise structure and security.But in reality, they often create complexity, cost, and pressure — without providing meaningful advantages over simpler early-stage instruments like SAFEs.Andy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comResourcesStartups Decoded Podcast: https://startupsdecoded.com
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Ep#6: SAFE Notes — Simple, Fast… and Fuzzy
Mar 2000:19:20Tap to summarizeSAFE notes are meant to make early-stage fundraising easy.And they do. But most founders and angels don’t fully understand what they’re signing up for.In this episode of Angels Decoded, Cheryl Kellond and Andy Walsh unpack how SAFEs actually work, why they’re the default at early stage, and where they can catch people out.They’re fast, flexible, and let founders raise money over time without stopping to run a full round.But under the surface…Valuations are mostly signal. Ownership gets unclear. And stacked SAFEs can quietly eat into founder equity. At the same time, what many angels miss is that SAFEs can work in their favor, with non-dilutive upside as the company grows.Subscribe nowWhat We Break DownSAFE ≠ simple: Easy to use, hard to fully understand.Valuation is still a signal: You’re not pricing the company… but you kind of are.Rolling capital wins: Raise as you build, not all at once.Stacked SAFEs = hidden dilution: Founders take the hit, not early investors.Angels benefit more than they think: Early checks can compound without dilution.The Big IdeaSAFE notes make fundraising faster. But if you don’t understand them…you won’t know what you own until it’s too late.Andy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comResourcesStartups Decoded Podcast: https://startupsdecoded.com
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Ep#5: Small Checks, Big Impact — The Real Math of Angel Investing
Mar 1300:18:08Tap to summarizeMany new angels think their first check has to be big to matter.In reality, the opposite is often true. Oversized early bets can limit diversification and reduce the odds of success. The real advantage in angel investing comes from building a portfolio over time.In Ep#5 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack the psychology and strategy behind check size, portfolio construction, and why writing smaller checks can actually create more impact for both founders and investors.The data is simple: returns improve once investors reach around 30 investments. That means angel investing isn’t about one big bet. It’s about thoughtful diversification, learning over time, and backing founders in a way that fits your financial reality.This conversation also explores how SPVs make small checks practical, why angels should check their ego at the door, and how even a $1,500 investment can create meaningful influence when paired with experience and support.Listen & Watch: Apple || Spotify || YouTubeThe Realities We Break Down1) The Check Size Myth Many new angels assume bigger checks equal more value. In reality, writing smaller checks allows investors to build diversified portfolios and learn the ecosystem without overextending early.2) The 30-Investment Rule Data from AngelList shows the strongest returns typically appear after 30 investments. Diversification, not conviction, is the statistical edge in early-stage investing.3) Why SPVs Make Small Checks Work Small checks don’t need to burden founders. When angels invest through SPVs, founders receive one clean entry on the cap table while investors participate collectively.4) Impact Beyond Capital Sometimes the most valuable angels aren’t the ones writing the biggest checks. Experience, introductions, and operational insight can matter far more than the dollar amount invested.The Big IdeaAngel investing isn’t about writing the biggest check.It’s about building a portfolio, supporting founders, and deploying capital thoughtfully over time. Small checks, when combined with experience and network, can drive meaningful impact for both startups and the broader innovation ecosystem.Chapters00:00 Introduction00:44 Why investors obsess over check size04:35 The impact of small checks on founders07:45 Angel investing and impact12:04 Diversification and the 30-investment rule14:57 Starting small and learning the ecosystem17:30 Why small checks still matterAndy Walsh2x exited founder and host of Startups Decoded (Top 2% globally). Andy helps founders sharpen judgment and build companies through practical experience and operator insight.Cheryl KellondFounder of Play Money and active angel investor. Cheryl focuses on democratizing angel investing and helping new investors build diversified portfolios while supporting founders with practical guidance and community.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comResourcesStartups Decoded Podcast: https://startupsdecoded.comAngelList: https://angel.co
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Ep#4: The Truth About Cap Tables and Angel Investing
Mar 600:18:21Tap to summarizeEvery new angel investor wants to see their name on the cap table.It feels official. It feels powerful. It feels like you’re really “in the game.” But in reality, that small line on a cap table can create a surprisingly large operational burden for the founder you’re trying to support.In Ep#4 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack the practical realities of cap tables, dilution, and why many angels misunderstand the role they should play once they invest.The uncomfortable truth is simple: small checks shouldn’t slow companies down. When angels insist on being directly on the cap table without understanding the legal mechanics behind it, they often introduce friction that founders have to spend time and money managing.This conversation explores why the best angels focus less on status and more on support.Listen & Watch: Apple || Spotify || YouTubeSubscribe nowThe Realities We Break Down1) The Hidden Cost of Cap TablesEvery individual investor listed on a cap table creates administrative work. Legal filings, shareholder approvals, and document updates all add up. Over time, each name can cost a startup $1,500–$2,000 in legal overhead.2) The ROFR ProblemMost angels don’t know what a Right of First Refusal (ROFR) actually is. But if you’re on the cap table, you’ll be asked to sign documents tied to it. One confused signature can delay a financing or acquisition.3) Dilution Isn’t the EnemyEarly investors often obsess over dilution. But if a company is raising new capital and growing, dilution simply means the business is becoming more valuable. Fewer shares at a much higher value is still a win.4) Influence vs. ImpactBeing on the cap table doesn’t give angels meaningful power. The most valuable angels are the ones who help founders with introductions, advice, encouragement, and real-world experience.The Big IdeaAngel investing works best when it functions as support, not control. Small checks shouldn’t create large operational headaches. Whether through SPVs or thoughtful investment structures, the goal should always be the same: Give founders capital without slowing them down.Chapters00:00 Introduction and Collaboration Plans00:20 Understanding Cap Tables and SPVs03:35 Dilution and Its Implications for Angel Investors08:54 Cap Tables vs SPVs — What Actually Matters18:06 Angels Decoded End CardThe HostsAndy Walsh: 2x exited founder and strategist. He helps investors and founders navigate the “power dynamics” of early-stage capital without the fluff.Cheryl Kellond (aka “Shezza”): 3x founder and CEO of Play Money. She’s on a mission to move accredited professionals from the sidelines into the game with a data-backed, pragmatic approach.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.comResourcesStartups Decoded Podcast AngelList
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Ep#3: Why SPVs are the "Professional Grade" Way to Angel Invest.
Feb 2700:17:25Tap to summarizeThere is no such thing as a "simple" direct investment.If you think being directly on a startup’s cap table is a badge of honor, you’re likely creating a massive administrative burden for the founder you claim to support. In Ep#3 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack why the Special Purpose Vehicle (SPV) is the pragmatic choice for anyone looking to move from "hobbyist" to "professional" investor.The reality is sharp: Most individual angels lack the time to manage 1065 tax forms, K-1s, and the endless "Rofer" (Right of First Refusal) documents that flood an inbox during a growth round. By pooling capital into an SPV, you aren't just simplifying your life; you’re de-risking the founder’s future by keeping their cap table clean for institutional VCs.The "Under the Hood" Realities We Unpack:The Respect Tax: Every unique name on a cap table costs a founder roughly $1,500–$2,000 in legal overhead over a decade. An SPV collapses that "tax" into a single line item.The "Black Box" Myth: Traditional SPVs often hide investors from founders. We discuss why transparency, giving founders your contact info while keeping the legal structure separate, is the only way to be a "value-add" angel.The Cost of Compliance: We get into the middle of fees. Yes, there is a cost to professional management, but it’s a fraction of the "time tax" you'd pay trying to DIY your own legal reviews and tax reporting.The numbers paint the real story. If you want to support a founder, don't just give them capital, give them optionality and a friction-free path to their next round. This conversation is the roadmap for how to do exactly that.Chapters00:00 The Power of Making Multiple Bets01:56 What is an SPV? (Getting under the hood of the LLC structure)04:50 Why Direct Cap Table Investing is a "World of Hurt" for Founders07:50 Navigating Fees: Why "Free" Investing Doesn't Exist12:52 The Human Element: Building Relationships through Stakeholder UpdatesThe HostsAndy Walsh: 2x exited founder and strategist. He helps investors and founders navigate the "power dynamics" of early-stage capital without the fluff.Cheryl Kellond (aka "Shezza"): 3x founder and CEO of Play Money. She’s on a mission to move accredited professionals from the sidelines into the game with a data-backed, pragmatic approach.Access All Areas.Subscribe: SubstackWeb: angelsdecoded.com
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