Play Money - Angel Investing, Made Easy

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 startups
• The flipped chart: the seven biggest charities in the country are now donor-advised funds, not the Red Cross or United Way
• Why the money sits still: donor complacency, and DAF sponsors earning on assets with no reason to remind you
• Personal impact funds: how DAF money now backs founders in $2,500 checks on Play Money
• The first step: one five-question form at letsplaymoney.com/daf, then a single dropdown in your DAF

Listen: Apple | Spotify | YouTube

Links
Start here: letsplaymoney.com/daf
Inspire 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.com
• Web: letsplaymoney.com
• Startups Decoded Podcast startupsdecoded.com

Disclaimer
The 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.

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 pod
• Why CPG feels like lighter diligence for a first-timer, and why that instinct is actually right, not lazy
• The acquisition playbook: how big CPG brands watch a category take off, then buy in at a predictable revenue mark
• The Poppy and Blue Bottle comps: $1.9B from Pepsi, $600M from Nescafe, and what they prove about exit timing
• The two kinds of risk: why angels only have to underwrite whether a brand can create a category, not whether it can scale to billions
• The $200M reality check: why chasing unicorns works against angels, and why a 3-5x in five years beats a 1000x in fifteen
• The Liquid Death effect: why first-timers who came in on a flashy deal built diversified portfolios three times faster than average
• What CPG conviction actually teaches a new angel about trusting their own gut

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: letsplaymoney.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.

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 planned
• The posse model — why stacking operators, advocates and investors in one room beats any single lens, including your own
• The pro-con call — the huddle Impact Investor runs after every diligence process, and why Pam calls it the best recording the group has
• The armrest test — Pam's real filter for founders: would you sit next to them coast-to-coast in economy
• Abundance over hoarding — why Pam's group broadcasts vetted deals to rival VCs instead of sitting on them
• The Baritone case — how ecosystem tailwinds and one domain expert on the team turned "sounds complicated" into conviction
• What "Impact Investor" on a deal actually signals to a Play Money angel scrolling past

Listen: 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.com
• Web: letsplaymoney.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.

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 entirely
• Hygiene versus real diligence: why cap tables and incorporation checks are borrowed trust, not original work
• Sizing the ask: why a $5,000 check earns thirty minutes, not three meetings
• Reading founders, not resumes: what good angels actually dig for in that conversation
• The adverse selection trap: how bad diligence habits quietly kill an angel's deal flow
• Trust the network, not just yourself: the proxy model for scaling diligence without burning founders' time

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 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.

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.

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.

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.

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.

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 | 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

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 | 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