Ep#17: Revenue Lies, AI Tricks, and What Angels Should Actually Ask

Ep#17: Revenue Lies, AI Tricks, and What Angels Should Actually Ask

Founders aren’t always lying. But they’re not always telling the full story either. Cheryl Kellond and Andy Walsh unpack the revenue terms that trip up new angel investors, and the specific ways AI companies are stretching numbers in ways that would make an accountant sweat. The episode starts with a real example: a company doing $40M in gross marketplace value that was actually generating $10M in revenue. Both numbers were true. Neither was wrong. But only one of them tells you what the business is actually worth. From there, Cheryl breaks down the three revenue patterns that catch angels off guard, marketplace GMV vs. take rate, the two completely different things that “ARR” can mean, and whether a company’s unit economics get better as they grow or just get worse faster. Then it gets interesting. AI companies are playing a different game entirely. Multi-year contracts where year one is free. Run rates built on a single good day. Revenue that looks like $10M but cost $20M to generate. These aren’t always bad-faith moves, but they are traps for investors who don’t know what to ask. The bigger point: great founders building real businesses are getting overshadowed by AI headline numbers that don’t hold up to a single follow-up question. Knowing what to ask levels the playing field. Topics covered: * GMV vs. take rate in marketplace businesses * The two ARRs — and why confusing them costs you * Unit economics: when costs scale with revenue vs. when they don’t * AWS credits are not investment (say it louder) * Multi-year contracts dressed up as ARR * Why honest founders are getting hurt by AI revenue theatrics * Three questions that cover 90% of what angels need to know * Cash vs. accruals and what contracted revenue actually means * Why peer learning makes you a better investor faster You don’t need to be a CFO to invest well. You just need to know what questions to ask first. 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: angelsdecoded.substack.com [https://angelsdecoded.substack.com/] * Web: angelsdecoded.com [http://angelsdecoded.com] * Startups Decoded Podcast startupsdecoded.com [https://startupsdecoded.com]

Ep#16: Why Angel Money is the Best Capital a Founder Ever Takes

Most founders are taught to believe angel funding is just a stepping stone to venture capital. In Ep#16 of Angels Decoded, Cheryl Kellond and Andy Walsh challenge that idea completely, arguing that angel capital may actually be the most important money a company ever raises. The conversation explores the growing divide between mission-aligned businesses and venture-backed growth at all costs. Cheryl explains why more founders are realizing that traditional VC funding can sometimes pull companies away from the very reason they were started in the first place. Using examples like Patagonia, Costco, Whole Foods, and Anthropic, the episode unpacks how ownership structures, investor expectations, and company charters can shape the long-term ethics, culture, and direction of a business. The discussion also reframes the role of angel investors entirely. Instead of being “minor league” capital, angels may be the investors best positioned to help founders stay aligned to mission while still building highly profitable companies. The bigger takeaway: the earliest capital a founder takes often determines the future of the company itself. Inspired by Eric Ries’s (The Lean Startup), brand new book Incorruptible. Topics covered: * Why angel capital may be more valuable than VC funding * The hidden tradeoffs founders make when raising venture capital * How investor pressure can reshape company missions * Why mission-driven companies often outperform financially * Public benefit corporations and founder protections * The rise of mission-aligned startup investing * How SPVs allow angels to support founders collectively * Why angels are entering a new “golden age” * The relationship between ethics, ownership, and profitability * Why founders should think carefully about who gets control early Sometimes the smartest investment isn’t just backing a company. It’s protecting the reason the company exists in the first place. 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: angelsdecoded.substack.com [https://angelsdecoded.substack.com/] * Web: angelsdecoded.com [http://angelsdecoded.com] * Startups Decoded Podcast startupsdecoded.com [https://startupsdecoded.com]

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]