Angels Decoded

Cheryl Kellond is back, and this time she’s calling out angel group sins. Three of them. Hoarding diligence, forcing minimum check sizes, and treating a cap table seat like a status symbol. If you’ve spent more than five minutes around an angel group, you’ve watched at least one of these play out. The pattern underneath all three is the same, scarcity thinking dressed up as process. Groups that si...

The startup map is being redrawn. Not by VCs flying in to write checks, but by founders who never left home. Cheryl Kellond has watched it happen from the inside, and this conversation is a real-time dispatch from the ground. The big insight here is simple: regional founders aren't disadvantaged anymore. AI has erased the knowledge gap. What they have instead is something money can't replicate: de...

Most angels hear the word dilution and flinch. Cheryl Kellond hears it and gets excited. By the end of this episode, you will too. Cheryl and Andy break down why dilution is almost always a signal that something good is happening, the pie got bigger, and why the angels who panic about ownership percentages are missing the point entirely. The math is simple once you stop letting the word scare you....

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...

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. Cher...

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 explain...

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 s...

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...

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 capi...

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 fric...

Angel 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 n...

AI 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 ar...

Angel 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...

Convertible 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, conv...

SAFE 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 st...

Many 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,...

Every 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,...

There 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 "pro...

There is no such thing as an "expert" angel investor. If you believe a single large return makes you an expert, you’re treating angel investing like a lottery ticket.  In Ep#2 of Angels Decoded, Cheryl Kellond and Andy Walsh unpack why that "one-off" mindset is a recipe for failure. The reality is pragmatic: the only reliable predictor of returns in early-stage startups is the number of check...

Writing an angel check is easy. Knowing why is the flex. In the debut episode of Angels Decoded , Andy Walsh and Cheryl Kellond trade the “country club” luncheon for the raw truth about early-stage capital. Angel investing is no longer just for semi-retired hobbyists on the driving range; it’s becoming the most strategic leverage a founder can have. Subscribe now The Death of the “Dumb Money” Myth...