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.
15episodes
Episodes
Newest firstAll episodes
Ep#15: Why Your Angel Thesis Shouldn’t Exist Yet
2w ago00:15:52Tap to summarizeMost new angel investors think they need a polished investment thesis before writing their first check.In Ep#15 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack why that thinking often keeps people stuck on the sidelines.The conversation explores one of the biggest misconceptions in angel investing: the idea that you need to think like a venture capitalist before you start. Cheryl explains that most experienced angels didn’t begin with a thesis. Their thesis evolved through the process of investing itself.From small early bets to discovering what genuinely resonates, the episode dives into how angel investing becomes as much about self-discovery as financial return.Cheryl shares stories of investments that looked smart on paper but left her emotionally disconnected, alongside others driven by lived experience, personal values, and genuine conviction. The result is a broader conversation about purpose, identity, and the role money plays in shaping the kind of world investors want to help build.The bigger takeaway: Your angel thesis isn’t something you invent upfront. It’s something you earn through experience.Listen: Apple | Spotify | YouTubeSubscribe nowTopics covered:Why new angels get stuck overthinking investment thesesThe difference between VC investing and angel investingHow small bets help investors discover convictionWhy lived experience can become a powerful investment lensThe emotional side of startup investingBuilding “emotional armor” around investment decisionsHow values and identity shape investment choicesWhy money should create more than just financial returnSometimes the smartest way to start investing is simply to start.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: angelsdecoded.substack.comWeb: angelsdecoded.comStartups Decoded Podcast startupsdecoded.com
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Ep#14: How Hidden Capital Unlocks Angel Investing
3w ago00:20:50Tap to summarizeMost people think angel investing is locked behind wealth, complexity, or Wall Street-level expertise.In Ep#14 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack a very different reality: many accredited investors already have capital sitting in plain sight. They just don’t realize they can use it.The episode starts with a simple but powerful point. If your retirement accounts are quietly sitting in ETFs or public markets for the next 10 to 15 years, that timeline already mirrors startup investing. The issue isn’t access. It’s awareness.Cheryl shares how discovering she could invest through an old IRA completely changed her relationship with angel investing. Instead of needing new disposable income, she realized she could redeploy existing retirement capital into startups she believed in.From there, the conversation expands into one of the most overlooked areas in startup investing today: donor-advised funds (DAFs).Most DAF capital sits passively in public markets, despite being designed to create impact. Cheryl explains how new platforms and charitable intermediaries are making it easier for people to deploy those funds into mission-aligned startups while still preserving the charitable structure and tax advantages.The bigger takeaway: you may not need more money to start angel investing. You may simply need to understand where your existing capital can go.Topics covered:• Why most people misunderstand access to angel investing• How IRAs and old 401(k)s can be used for startup investing• Why traditional custodians rarely explain these options• The rise of alternative investment custodians• What donor-advised funds (DAFs) actually are• How DAF capital can support startups and impact investing• Why “money hiding in plain sight” is the real unlock• The psychological barriers stopping new angels from startingThe barrier often isn’t capital.It’s knowing the rules of the game have already changed.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#13: Why Angels Aren’t Small VCs (And Why That Matters)
4w ago00:15:14Tap to summarizeAngel investing isn’t complicated. We’ve just made it feel that way.In Ep#13 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack one of the biggest misconceptions in early-stage investing: the belief that you need to operate like a venture capitalist to get started.The episode opens with a simple story — a senior operator who avoided angel investing for years because she thought she wasn’t an accredited investor. When she finally looked it up, she realized she had qualified all along. The barrier wasn’t financial. It was psychological.From there, Cheryl makes the core point: angels are not small VCs.VCs invest full-time using other people’s money. Angels invest their own, bringing judgment and experience — not institutional process.The issue is how angel investing is taught. Much of the advice focuses on sourcing deals and running diligence, which adds complexity and keeps people on the sidelines.This episode reframes that approach.Instead of acting like VCs, angels can: plug into pre-vetted deal flow, trust their instincts, and start small, learning by doing.The opportunity isn’t becoming a VC. It’s participating — without overcomplicating it.Subscribe nowTopics covered: • Why “accredited investor” is misunderstood • The real barrier to getting started • How angels differ from VCs • Why education often overcomplicates things • How to start without full diligence • The role of intuition in investingMost people aren’t locked out. They’ve just been taught the wrong way in.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.comStartups Decoded Podcast startupsdecoded.com
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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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