Play Money - Angel Investing, Made Easy

Andy Walsh
  • 5.0 (2)
  • Investing
  • Updated Weekly

Writing a check is easy. Knowing why is the flex. Angel investing is underused, misunderstood, and explained badly. Play Money is a platform and community that connects angel investors with great founders who are fundraising.Subscribe. Then decide.

  1. 1d ago

    Ep#25: The Ultimate Play Money: Why Your DAF Should Be Angel Investing

    Angels Decoded is now the Play Money Podcast, and we’re kicking off the new format with our first guest.  More than $300 billion sits in donor-advised funds across the US, already given away and already tax-deducted, and most of it is parked in index funds earning fees for folks like Fidelity and Vanguard. Patrice Brickman runs Inspire Access, a 501(c)(3) that moves that idle capital into women and underrepresented founders. You grant the money as you would to any charity, Inspire Access makes the investment, and returns flow back into your DAF to be used again. Patrice calls it renewable philanthropy. The anchor story is what she and Cheryl built together. DAF money usually moves in $25,000 or $50,000 blocks, so they cracked a way to land it on Play Money as a personal impact fund, letting donors write small checks across a portfolio. The breakthrough came mid-Zoom, Patrice with foils in her hair and Cheryl hauling a bag of rice. Getting started takes one form, and if the money has already left your pocket, the risk to you is zero. Episode outline How a DAF really works: donate, take the deduction, then invest that same money in startupsThe flipped chart: the seven biggest charities in the country are now donor-advised funds, not the Red Cross or United WayWhy the money sits still: donor complacency, and DAF sponsors earning on assets with no reason to remind youPersonal impact funds: how DAF money now backs founders in $2,500 checks on Play MoneyThe first step: one five-question form at letsplaymoney.com/daf, then a single dropdown in your DAFListen: Apple | Spotify | YouTube LinksStart here: letsplaymoney.com/dafInspire Access: https://www.inspireaccess.org/  Patrice Brickman - https://www.linkedin.com/in/patrice-brickman/ Patrice Brickman is the Founder and CEO of Inspire Access, a nonprofit investing philanthropic dollars into underrepresented founders. She also founded Inspire Capital, a venture fund backing women and minority-led businesses, and sits on the board of Maryland’s TEDCO. 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 letsplaymoney.substack.comWeb: letsplaymoney.comStartups Decoded Podcast startupsdecoded.comDisclaimerThe views and opinions shared on the Play Money Podcast are for informational purposes only and do not constitute investment, tax or legal advice. Always consult a qualified professional before making any financial, tax or legal decisions.

    Ep#25: The Ultimate Play Money: Why Your DAF Should Be Angel Investing

  2. Sep 11

    Ep#24: The Affogato Effect — Why CPG Is Angel Investing's On-Ramp

    Cheryl's calling it Affogato August. This summer, the deals that caught fire on Play Money weren't the moonshots, they were Thai-flavored ice cream and decaf coffee, both gone in days at six-figure SPVs. Andy and Cheryl unpack why CPG keeps working as everyone's first angel check: it's the one category where your gut is basically already doing the diligence for you. The anchor story is Liquid Death, the late-stage deal that pulled in a wave of angels who'd never written a check before, who then went on to build portfolios three times faster than the platform average, and diversified well outside CPG. Sixty percent of investors into last summer's CPG deals were first-timers. This episode is about why that on-ramp works, and what it teaches angels who think they need something more sophisticated to start. Episode outline The Affogato August story: how Thai ice cream and decaf coffee outran a snow-making bioprotein and a Mars farming podWhy CPG feels like lighter diligence for a first-timer, and why that instinct is actually right, not lazyThe acquisition playbook: how big CPG brands watch a category take off, then buy in at a predictable revenue markThe Poppy and Blue Bottle comps: $1.9B from Pepsi, $600M from Nescafe, and what they prove about exit timingThe two kinds of risk: why angels only have to underwrite whether a brand can create a category, not whether it can scale to billionsThe $200M reality check: why chasing unicorns works against angels, and why a 3-5x in five years beats a 1000x in fifteenThe Liquid Death effect: why first-timers who came in on a flashy deal built diversified portfolios three times faster than averageWhat CPG conviction actually teaches a new angel about trusting their own gutListen: 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.comWeb: letsplaymoney.comStartups Decoded Podcast startupsdecoded.comDisclaimer 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.

    Ep#24: The Affogato Effect — Why CPG Is Angel Investing's On-Ramp

  3. Aug 28

    Ep#23: The Posse Model — Why One Angel's Gut Isn't Enough

    Pam Scott runs Impact Investor, a group built from three kinds of angels who rarely agree with each other: operators who grill the fundamentals, advocates who care about the impact story, and seasoned investors who pressure-test the terms.  Cheryl calls the resulting diligence more rigorous than most VCs manage. Pam calls it the only reason she's learned more in two years than in the twenty before it. The anchor story is Baritone — a band-aid-sized sleep apnea diagnostic, backed by specialist VCs and fast-tracked by the FDA — that Pam's group bet on as a unit before it ever reached Play Money. Less than 5% of accredited women currently invest. This episode is about what deal flow looks like once that number starts moving. Episode outline The accidental start — how a brand strategist doing equity work for a scrappy founder named Eric Ryan ended up with two decades of angel investing she never plannedThe posse model — why stacking operators, advocates and investors in one room beats any single lens, including your ownThe pro-con call — the huddle Impact Investor runs after every diligence process, and why Pam calls it the best recording the group hasThe armrest test — Pam's real filter for founders: would you sit next to them coast-to-coast in economyAbundance over hoarding — why Pam's group broadcasts vetted deals to rival VCs instead of sitting on themThe Baritone case — how ecosystem tailwinds and one domain expert on the team turned "sounds complicated" into convictionWhat "Impact Investor" on a deal actually signals to a Play Money angel scrolling pastListen: Apple | Spotify | YouTube Pam Scott - https://www.linkedin.com/in/curiouspam/ Pam Scott spent two decades advising founders for equity before she noticed the pattern: the women she was betting on kept getting a sliver of the capital. She built Impact Invest Her to fix the investor side of that math, not just the founder side. 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.comWeb: letsplaymoney.comStartups Decoded Podcast startupsdecoded.comDisclaimer 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.

    Ep#23: The Posse Model — Why One Angel's Gut Isn't Enough

  4. Jul 31

    Ep#22: The Angels Who Diligence Too Much Get the Worst Deals

    Most angels think heavy diligence makes them safer.  Cheryl Kellond says it just makes them slower, and less trusted. She told a founder to skip an angel group's pitch process entirely, because they grill founders for hours before writing checks that barely clear five figures. The math never worked. Diligence still matters, but it needs to scale with the check size. Cap tables and incorporation checks are hygiene, borrowed trust from whoever vetted the deal before you. What actually matters is reading the founder and reading the market, and even that should run through people you trust, not just your own hours. Episode outline The over-diligenced deal that never happened: how a founder saved weeks by skipping an angel group's pitch process entirelyHygiene versus real diligence: why cap tables and incorporation checks are borrowed trust, not original workSizing the ask: why a $5,000 check earns thirty minutes, not three meetingsReading founders, not resumes: what good angels actually dig for in that conversationThe adverse selection trap: how bad diligence habits quietly kill an angel's deal flowTrust the network, not just yourself: the proxy model for scaling diligence without burning founders' timeListen: 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.comWeb: angelsdecoded.com Startups Decoded Podcast startupsdecoded.comDisclaimer 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.

    Ep#22: The Angels Who Diligence Too Much Get the Worst Deals

  5. Jul 17

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

    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 figureThe fund size trap: why VCs pass on companies that could return a huge multiple, purely because the exit won’t repay the whole fundThe magic number thirty: Abe Othman’s AngelList data on when a portfolio starts behaving like an asset class instead of lottery ticketsThe exit math nobody shares: ninety percent of exits land under $100 million, and they happen faster and at lower riskThe power shift problem: how each VC round hands exit decisions to stakeholders optimizing for their own multiplier, not the founder’sRole reversal: Cheryl defends VCs as professionals doing their job, and lands the real lesson, angels are not small VCsListen: 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.comWeb: angelsdecoded.comStartups Decoded Podcast startupsdecoded.comDisclaimer. 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.

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

  6. Jul 10

    Ep#20: The Three Deadly Sins of Angel Investing

    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 oneSin #1, hoarding diligence: why sharing your diligence can be the difference between a founder raising $200K or pulling in a $1M follow-on checkSin #2, minimum check sizes: the old $10K rule pushing out a newer, busier, more distributed generation of angelsSin #3, cap table obsession: why insisting on a direct seat can actually cost the founder money and momentumThe SPV fix: how automated tools make the old excuses about cost and admin obsoleteThe abundance mindset: what changes for a local ecosystem when the anchor angel group chooses to amplify instead of gatekeepListen: 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.comWeb: angelsdecoded.comStartups Decoded Podcast: startupsdecoded.comDisclaimer 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.

    Ep#20: The Three Deadly Sins of Angel Investing

  7. Jun 26

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

    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 hubsWhat regional actually means: Louisiana, Birmingham, Tulsa: different models, same underlying logicThe VC blind spot: Why most institutional capital ignores regional deals, and why that's the arbitrageThe Portland problem: What happens when exits don't recycle capital locallyThe angel opportunity: Why angels, not VCs, are best positioned to capture regional upsidePlay Money's angle: 60% of investors on the platform aren't from California or New YorkListen: 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.comWeb: 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.

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

  8. Jun 19

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

    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 panicHow the pie analogy actually works across funding roundsThe angel math: why more bets beats doubling down every timeCost basis and why your entry point determines your multipleWhat a cram-down round is and how to spot oneThe sunk cost trap angels fall into when companies strugglePlay Money’s dilution calculator and how to use itWhy transparency on deal terms changes everythingDilution Calculator letsplaymoney.com/decodedYou 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 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.comDisclaimer: 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.

    Ep#18: Dilution Isn't the Problem. Not Understanding It Is.
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Writing a check is easy. Knowing why is the flex. Angel investing is underused, misunderstood, and explained badly. Play Money is a platform and community that connects angel investors with great founders who are fundraising.Subscribe. Then decide.

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