Angels Decoded

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.

Angels Decoded is a business podcast hosted by Andy Walsh, with 22 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Andy Walsh hosts Angels Decoded, a business show with 22 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Angels Decoded

  Ep#21: Angels, The Power Law Is Lying to You

  Jul 17, 202616 min

  The power law is the most quoted idea in angel investing, and it’s also the most misunderstood. Cheryl Kellond is back to dismantle it. VCs took a principle from nature, one big winner can dwarf everything else, and twisted it into a rule that only ten billion dollar outcomes count. The result is angels sitting on the sidelines, convinced they need to find the next Uber before writing a single check. The math tells a different story. Around ninety percent of startup exits happen under $100 million, with the median sitting near $44 million. Get in early at a $5 million post-money valuation and a $50 million exit is a monster multiple. Thirty bets turns angel investing into a predictable, high-performing asset class that beats public markets without ever touching a unicorn. The sharpest turn comes late, when Cheryl defends the VCs Andy just put on trial. VCs aren’t villains, they’re doing the job their LPs pay them to do. The mistake is angels thinking that job is theirs too. It isn’t. Angels have different math, different incentives, and a very different definition of winning. Episode outline. Where the power law actually comes from: nature, not venture capital, and how VC twisted a proportionality principle into an absolute dollar figure The fund size trap: why VCs pass on companies that could return a huge multiple, purely because the exit won’t repay the whole fund The magic number thirty: Abe Othman’s AngelList data on when a portfolio starts behaving like an asset class instead of lottery tickets The exit math nobody shares: ninety percent of exits land under $100 million, and they happen faster and at lower risk The power shift problem: how each VC round hands exit decisions to stakeholders optimizing for their own multiplier, not the founder’s Role reversal: Cheryl defends VCs as professionals doing their job, and lands the real lesson, angels are not small VCs Listen: Apple | Spotify | YouTube Subscribe now 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 earned 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 Web: angelsdecoded.com Startups Decoded Podcast startupsdecoded.com Disclaimer. The views and opinions shared on Angels Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

  ListenShow Notes
• 

  Angels Decoded

  Ep#20: The Three Deadly Sins of Angel Investing

  Jul 10, 202617 min

  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 sit on diligence instead of sharing it, groups that force $10K minimums on people who’d rather write ten $1K checks, groups that need a direct cap table seat to feel like they matter. Cheryl’s watched the same founder gain or lose a million dollars in funding, purely based on whether the group backing them chose to open up or lock down. The fix isn’t complicated. Share your diligence, drop the arbitrary minimums, use an SPV instead of clogging the cap table. Do that, and you’re not just getting a founder funded faster, you’re setting up a better return for yourself too. Episode outline The three deadly sins: hoarding diligence, forcing big minimum checks, and cap table ego, named and unpacked one by one Sin #1, hoarding diligence: why sharing your diligence can be the difference between a founder raising $200K or pulling in a $1M follow-on check Sin #2, minimum check sizes: the old $10K rule pushing out a newer, busier, more distributed generation of angels Sin #3, cap table obsession: why insisting on a direct seat can actually cost the founder money and momentum The SPV fix: how automated tools make the old excuses about cost and admin obsolete The abundance mindset: what changes for a local ecosystem when the anchor angel group chooses to amplify instead of gatekeep Listen: Apple | Spotify | YouTube Subscribe now 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 Web: angelsdecoded.com Startups Decoded Podcast: startupsdecoded.com Disclaimer The views and opinions shared on Angels Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

  ListenShow Notes
• 

  Angels Decoded

  Ep#19: The Best Deals Are Already in Your Backyard.

  Jun 26, 202619 min

  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: deep domain expertise, local networks, and proximity to the actual problem. That's a competitive moat, not a consolation prize. We also got into why most VCs are just lazy. Not malicious, not strategic, lazy. The best arbitrage in early-stage investing right now is sitting outside San Francisco and New York, and most institutional capital is too comfortable to go look for it. Episode outline The new startup map : How AI leveled the playing field for founders building outside major tech hubs What regional actually means : Louisiana, Birmingham, Tulsa: different models, same underlying logic The VC blind spot : Why most institutional capital ignores regional deals, and why that's the arbitrage The Portland problem : What happens when exits don't recycle capital locally The angel opportunity : Why angels, not VCs, are best positioned to capture regional upside Play Money's angle : 60% of investors on the platform aren't from California or New York Listen: Apple | Spotify | YouTube 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 Web: angelsdecoded.com   Startups Decoded Podcast startupsdecoded.com Disclaimer The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

  ListenShow Notes
• 

  Angels Decoded

  Ep#18: Dilution Isn't the Problem. Not Understanding It Is.

  Jun 19, 202617 min

  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. The episode opens with a Portuguese tart and an Australian meat pie, because apparently that’s how you explain equity to people. But the analogy lands: a smaller slice of a much bigger pie is almost always the better outcome. What matters isn’t your percentage, it’s what that percentage is worth when the company exits. Cheryl walks through what actually happens at each funding round, why angels shouldn’t follow VCs into follow-on bets, and the AngelList data on why doubling down is usually a mistake. The better move is more shots on goal, not more money into the same bet. Cheryl unpacks cram down rounds, what they are, why founders use them, and why angels almost always misread them as opportunity when they’re actually a distress signal. If a company is trying to get you to reinvest by threatening to convert your preferred shares to common, that’s not an attractive deal. That’s a company in trouble using your fear against you. She also shares the story that led her to build Play Money the way she did, a cram-down dressed up as a late-stage opportunity, a room full of angels leaning in, and deal terms nobody volunteered to show anyone. Topics covered: Why dilution is a reason to celebrate, not panic How the pie analogy actually works across funding rounds The angel math: why more bets beats doubling down every time Cost basis and why your entry point determines your multiple What a cram-down round is and how to spot one The sunk cost trap angels fall into when companies struggle Play Money’s dilution calculator and how to use it Why transparency on deal terms changes everything Dilution Calculator letsplaymoney.com/decoded You don’t need to be a VC to understand dilution. You just need to stop treating it like a dirty word. Listen: Apple | Spotify | YouTube Subscribe now Andy 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: angelsdecoded.substack.com Web: angelsdecoded.com Startups Decoded Podcast startupsdecoded.com Disclaimer: The views and opinions shared on Startups Decoded are for informational purposes only and do not constitute investment or legal advice. Always consult a qualified professional before making any financial or legal decisions.

  ListenShow Notes
• 

  Episode #17

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

  Jun 5, 202618 minS0

  <p>Founders aren’t always lying. But they’re not always telling the full story either.</p><p>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.</p><p>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.</p><p>From there, Cheryl breaks down...

  ListenShow Notes

Recent guests on Angels Decoded. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.