Ep#12: The Angel Advantage in Venture Capital’s “Black Hole"

Ep#15: Why Your Angel Thesis Shouldn’t Exist Yet

Most 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 [https://podcasts.apple.com/us/podcast/angels-decoded/id1877002704] | Spotify [https://open.spotify.com/show/1MiXOD6tohVIvnoLndsnQd] | YouTube [https://www.youtube.com/@AngelsDecoded] Subscribe now [%%checkout_url%%] Topics covered: * Why new angels get stuck overthinking investment theses * The difference between VC investing and angel investing * How small bets help investors discover conviction * Why lived experience can become a powerful investment lens * The emotional side of startup investing * Building “emotional armor” around investment decisions * How values and identity shape investment choices * Why money should create more than just financial return Sometimes the smartest way to start investing is simply to start. Andy Walsh [https://www.linkedin.com/in/anwalsh/] 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 [https://www.linkedin.com/in/c2kprofile/] 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: angelsdecoded.substack.com [https://angelsdecoded.substack.com/] Web: angelsdecoded.com [http://angelsdecoded.com] Startups Decoded Podcast startupsdecoded.com [https://startupsdecoded.com]

Ep#14: How Hidden Capital Unlocks Angel Investing

Most 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 starting The barrier often isn’t capital. It’s knowing the rules of the game have already changed. Listen: Apple [https://podcasts.apple.com/us/podcast/angels-decoded/id1877002704] | Spotify [https://open.spotify.com/show/1MiXOD6tohVIvnoLndsnQd] | YouTube [https://www.youtube.com/@AngelsDecoded] Subscribe now [%%checkout_url%%] Andy Walsh [https://www.linkedin.com/in/anwalsh/] 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 [https://www.linkedin.com/in/c2kprofile/] 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: Substack [https://angelsdecoded.substack.com/] Web: angelsdecoded.com [http://angelsdecoded.com] Startups Decoded Podcast: startupsdecoded.com [https://startupsdecoded.com]

Ep#13: Why Angels Aren’t Small VCs (And Why That Matters)

Angel 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 now [%%checkout_url%%] Topics 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 investing Most people aren’t locked out. They’ve just been taught the wrong way in. Listen: Apple [https://podcasts.apple.com/us/podcast/angels-decoded/id1877002704] | Spotify [https://open.spotify.com/show/1MiXOD6tohVIvnoLndsnQd] | YouTube [https://www.youtube.com/@AngelsDecoded] Andy Walsh [https://www.linkedin.com/in/anwalsh/] 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 [https://www.linkedin.com/in/c2kprofile/] 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: Substack [https://angelsdecoded.substack.com/] * Web: angelsdecoded.com [http://angelsdecoded.com] * Startups Decoded Podcast startupsdecoded.com [https://startupsdecoded.com]

Ep#12: The Angel Advantage in Venture Capital’s “Black Hole"

When 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 potential When 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 [https://podcasts.apple.com/us/podcast/angels-decoded/id1877002704] | Spotify [https://open.spotify.com/show/1MiXOD6tohVIvnoLndsnQd] | YouTube [https://www.youtube.com/@AngelsDecoded] Subscribe now [%%checkout_url%%] Andy Walsh [https://www.linkedin.com/in/anwalsh/] 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 [https://www.linkedin.com/in/c2kprofile/] 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: Substack [https://angelsdecoded.substack.com/] * Web: angelsdecoded.com [http://angelsdecoded.com] * Startups Decoded Podcast: startupsdecoded.com [https://startupsdecoded.com/]

Ep#11: The New Founder Playbook in the Age of AI

AI 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 AI AI won’t magically create great founders. But it will amplify the ones who know how to use it. Listen: Apple [https://podcasts.apple.com/us/podcast/angels-decoded/id1877002704] | Spotify [https://open.spotify.com/show/1MiXOD6tohVIvnoLndsnQd] | YouTube [https://www.youtube.com/@AngelsDecoded] Andy Walsh [https://www.linkedin.com/in/anwalsh/] 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 [https://www.linkedin.com/in/c2kprofile/]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: Substack [https://angelsdecoded.substack.com/] * Web: angelsdecoded.com [http://angelsdecoded.com]  * Startups Decoded Podcast - startupsdecoded.com [https://startupsdecoded.com]