Play Money - Angel Investing, Made Easy

Ep#26: The Riskiest Check Is the One You Never Write

Andy Walsh — Fri, 23 Oct 2026 03:00:00 +0000

Cheryl has spent the last few weeks on panels where every mention of startup investing came with a risk warning attached.

Nobody issues that warning when someone writes a $10,000 check at the sports boosters gala or buys a $5,000 handbag, and both of those come with zero financial return.

Her view, backed by math, is that the bigger risk sits on the other side of the decision. When you don’t write the check, the problems you need solved stay unsolved, and the companies built on your taste, expertise and spending make money for someone else.

The episode also takes apart the guy on stage who wrote three big checks, lost them all, and told the room nobody should angel invest. His problem was concentration and check size. Cheryl lays out the sizing math that fixes it, deals with the lock-up myth, and closes with what happens if 10% of people who could angel invest put in $1,000 a month.

Episode outline

The double standard: why nobody lectures you on risk at the charity gala or the handbag counter, but everyone does when you look at a startup
The four bottom lines: your voice, your return, backing a founder without access to capital, and building an industry nobody funds
First check calls the game: a $2,000 bet on a swab test for gynecological cancers, and what the real risk was
The three-check guy: why losing big on three bets says more about sizing than about angel investing
The sizing math: 7% of assets, 30 bets over five to six years, roughly a $2,000 check for every $1M in assets
The lock-up myth: most of your money is already tied up for decades in your retirement accounts
The 10% scenario: how $12,000 a year from a fraction of eligible angels would outsize the $30B US early-stage VC market

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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
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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.

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

Andy Walsh — Fri, 16 Oct 2026 15:01:31 +0000

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

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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.

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

Andy Walsh — Fri, 11 Sep 2026 12:29:41 +0000

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.

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

Andy Walsh — Fri, 28 Aug 2026 07:00:00 +0000

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

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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.

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

andy walsh — Fri, 31 Jul 2026 07:00:00 +0000

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

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

Andy Walsh — Fri, 17 Jul 2026 06:22:00 +0000

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

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Web: angelsdecoded.com
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Disclaimer.

Ep#20: The Three Deadly Sins of Angel Investing

Andy Walsh — Fri, 10 Jul 2026 09:41:00 +0000

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

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

Andy Walsh — Fri, 26 Jun 2026 07:34:00 +0000

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

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Web: angelsdecoded.com
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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#18: Dilution Isn't the Problem. Not Understanding It Is.

andy walsh — Fri, 19 Jun 2026 07:07:00 +0000

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.

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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.

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

andy walsh — Fri, 05 Jun 2026 07:49:00 +0000

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.

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Subscribe: angelsdecoded.substack.com
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Ep#16: Why Angel Money is the Best Capital a Founder Ever Takes

andy walsh — Fri, 29 May 2026 07:17:00 +0000

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.

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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.

Access All Areas.

Subscribe: angelsdecoded.substack.com
Web: angelsdecoded.com
Startups Decoded Podcast startupsdecoded.com

Ep#15: Why Your Angel Thesis Shouldn’t Exist Yet

andy walsh — Fri, 22 May 2026 07:08:00 +0000

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.

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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
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.

Access All Areas.

Subscribe: angelsdecoded.substack.com

Web: angelsdecoded.com

Startups Decoded Podcast startupsdecoded.com

Ep#14: How Hidden Capital Unlocks Angel Investing

andy walsh — Fri, 15 May 2026 09:26:00 +0000

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.

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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.

Access All Areas.

Subscribe: Substack

Web: angelsdecoded.com

Startups Decoded Podcast: startupsdecoded.com

Ep#13: Why Angels Aren’t Small VCs (And Why That Matters)

andy walsh — Fri, 08 May 2026 10:57:18 +0000

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.

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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 | Spotify | YouTube

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: Substack
Web: angelsdecoded.com
Startups Decoded Podcast startupsdecoded.com

Ep#12: The Angel Advantage in Venture Capital’s “Black Hole"

Andy Walsh — Fri, 01 May 2026 10:30:00 +0000

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 capital concentrates into a small number of mega deals, entire sectors are being overlooked. That creates what investors call arbitrage: the chance to invest in strong companies at lower valuations while clear exit paths still exist.

This episode explores why angels operate under different incentives than venture capital funds, how capital concentration creates mispricing in the market, and why sectors like climate tech, consumer products, and women’s health may offer compelling opportunities right now.

Topics covered:

• Why venture capital is concentrating on a handful of AI deals
• The structural difference between angels and VC funds
• How market concentration creates arbitrage opportunities
• Why entry valuation matters for investor returns
• Sectors being overlooked despite strong exit potential

When capital crowds into the same deals, the smartest investors often look somewhere else.

Sometimes the real opportunity is inside the so-called “black hole.”

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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.

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com
Startups Decoded Podcast: startupsdecoded.com

Ep#11: The New Founder Playbook in the Age of AI

andy walsh — Fri, 24 Apr 2026 08:29:00 +0000

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 friction, unlock new capabilities, and reshape how teams build and scale.

This episode unpacks how AI is raising the ceiling for startups, why tinkering and experimentation are becoming core founder skills, and the questions investors should be asking to identify founders who can thrive in this new environment.

Topics covered:
• Founder traits in the age of AI
• How AI changes startup building and scaling
• Why “tinkering” is a new founder skill
• The difference between hype and real AI advantage
• Questions investors should ask founders about AI

AI won’t magically create great founders.

But it will amplify the ones who know how to use it.

Listen: Apple | Spotify | YouTube

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.

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com
Startups Decoded Podcast - startupsdecoded.com

Ep#10: The Echo Chamber Problem in Venture Capital

Andy Walsh — Fri, 17 Apr 2026 07:37:00 +0000

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 new class of investors is emerging. Yet fewer than 5% of accredited investors currently participate in startup investing, leaving enormous room for growth.

This episode explores how venture capital echo chambers form, why new investor markets are often ignored, and how platforms, universities, and generational wealth transfer are expanding access to angel investing.

Topics covered:
• Angel investing market opportunities
• Generational wealth transfer and startup funding
• Venture capital echo chambers
• Democratization of startup investing
• New investor models and platforms

Angel investing is changing.

The next wave of startup capital may come from investors the venture industry isn’t even looking at yet.

Advice: Write the check.

Listen: Apple | Spotify | YouTube

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: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast
https://startupsdecoded.com

Ep#9: Building Your Own AI Investment Framework

Andy Walsh — Thu, 09 Apr 2026 17:54:00 +0000

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 are navigating the same uncertainty.

That shift means angels can no longer rely on borrowed conviction. Instead, they need their own framework for evaluating startups in a world where AI is becoming the default technology layer.

This episode explores how investors can cut through the noise, what signals still matter, and why proprietary data may become the most valuable asset a startup can build.

Topics covered:
• Why traditional investment signals are becoming less reliable
• How AI is shifting the way startups create competitive advantage
• The difference between companies AI can replace and those AI strengthens
• Why proprietary and evolving data may determine future startup value
• How angel investors can build their own decision-making framework

Angel investing has always involved uncertainty.

In the age of AI, conviction matters even more.

Advice: Build your own framework before writing the check.

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

Access All Areas.

Subscribe: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast

Ep#8: The Emotional Cost of Optimism in Angel Investing

Andy Walsh — Fri, 03 Apr 2026 08:22:00 +0000

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 yet. But when the world feels unstable, even experienced investors can find themselves pulling back.

This episode explores why that hesitation happens, how uncertainty impacts capital deployment, and why staying engaged with founders may be more important than ever.

Topics covered:

• Why angel investing is fundamentally an act of optimism
• The emotional impact of uncertainty on investment decisions
• How stepping back from investing can slow innovation
• The unexpected personal and professional benefits of writing early-stage checks
• Why connecting with founders can reignite belief in the future

Sometimes the best response to uncertainty is simple:

Advice: Just write the damn check.

Listen: Apple | Spotify | YouTube

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.

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com

Resources

Startups Decoded Podcast: https://startupsdecoded.com

Ep#7: Convertible Notes — Complex, Costly, and Mostly Unnecessary

Andy Walsh — Fri, 27 Mar 2026 06:28:00 -0100

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, convertible notes look attractive. They include debt, interest, and a timeline for conversion into equity. That structure can make investors feel like they have something more “real” than a SAFE.

But in practice, those features rarely deliver the benefits people expect.

Debt in a pre-revenue startup rarely has real protection. Interest can create phantom income and tax headaches. And the maturity timelines almost always get extended rather than enforced.

Meanwhile, convertible notes can introduce unnecessary pressure into founder relationships and create major administrative complexity when a priced round finally happens.

This episode explores why convertible notes often solve problems that don’t really exist, while introducing new ones that founders and angels rarely anticipate.

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What We Break Down

Convertible notes are technically debt
They accrue interest and convert to equity later, but that debt rarely offers real protection in early-stage startups.

Interest creates phantom income
Investors can end up paying taxes on interest that hasn’t actually produced cash.

The timeline pressure is mostly artificial
Most notes get extended rather than converted when the maturity date arrives.

QSBS tax advantages can disappear
Because convertible notes are structured as debt, investors may lose early eligibility for Qualified Small Business Stock tax benefits.

Administrative complexity explodes
Different investors entering at different times create complicated calculations when notes convert into equity.

The Big Idea

Convertible notes promise structure and security.

But in reality, they often create complexity, cost, and pressure — without providing meaningful advantages over simpler early-stage instruments like SAFEs.

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

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com

Resources

Startups Decoded Podcast: https://startupsdecoded.com

Ep#6: SAFE Notes — Simple, Fast… and Fuzzy

Andy Walsh — Fri, 20 Mar 2026 06:34:00 -0100

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 stopping to run a full round.

But under the surface…Valuations are mostly signal. Ownership gets unclear. And stacked SAFEs can quietly eat into founder equity. At the same time, what many angels miss is that SAFEs can work in their favor, with non-dilutive upside as the company grows.

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What We Break Down

SAFE ≠ simple: Easy to use, hard to fully understand.
Valuation is still a signal: You’re not pricing the company… but you kind of are.
Rolling capital wins: Raise as you build, not all at once.
Stacked SAFEs = hidden dilution: Founders take the hit, not early investors.
Angels benefit more than they think: Early checks can compound without dilution.

The Big Idea

SAFE notes make fundraising faster. But if you don’t understand them…you won’t know what you own until it’s too late.

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

Access All Areas.

Subscribe: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast: https://startupsdecoded.com

Ep#5: Small Checks, Big Impact — The Real Math of Angel Investing

andy walsh — Fri, 13 Mar 2026 06:15:00 -0100

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, and why writing smaller checks can actually create more impact for both founders and investors.

The data is simple: returns improve once investors reach around 30 investments. That means angel investing isn’t about one big bet. It’s about thoughtful diversification, learning over time, and backing founders in a way that fits your financial reality.

This conversation also explores how SPVs make small checks practical, why angels should check their ego at the door, and how even a $1,500 investment can create meaningful influence when paired with experience and support.

Listen & Watch:

Apple || Spotify || YouTube

The Realities We Break Down

1) The Check Size Myth
Many new angels assume bigger checks equal more value. In reality, writing smaller checks allows investors to build diversified portfolios and learn the ecosystem without overextending early.

2) The 30-Investment Rule
Data from AngelList shows the strongest returns typically appear after 30 investments. Diversification, not conviction, is the statistical edge in early-stage investing.

3) Why SPVs Make Small Checks Work
Small checks don’t need to burden founders. When angels invest through SPVs, founders receive one clean entry on the cap table while investors participate collectively.

4) Impact Beyond Capital
Sometimes the most valuable angels aren’t the ones writing the biggest checks. Experience, introductions, and operational insight can matter far more than the dollar amount invested.

The Big Idea

Angel investing isn’t about writing the biggest check.

It’s about building a portfolio, supporting founders, and deploying capital thoughtfully over time. Small checks, when combined with experience and network, can drive meaningful impact for both startups and the broader innovation ecosystem.

Chapters

00:00 Introduction
00:44 Why investors obsess over check size
04:35 The impact of small checks on founders
07:45 Angel investing and impact
12:04 Diversification and the 30-investment rule
14:57 Starting small and learning the ecosystem
17:30 Why small checks still matter

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

Access All Areas.

Subscribe: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast: https://startupsdecoded.com

AngelList: https://angel.co

Ep#4: The Truth About Cap Tables and Angel Investing

Andy Walsh — Fri, 06 Mar 2026 07:49:00 -0100

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, and why many angels misunderstand the role they should play once they invest.

The uncomfortable truth is simple: small checks shouldn’t slow companies down. When angels insist on being directly on the cap table without understanding the legal mechanics behind it, they often introduce friction that founders have to spend time and money managing.

This conversation explores why the best angels focus less on status and more on support.

Listen & Watch: Apple || Spotify || YouTube

Subscribe now

The Realities We Break Down

1) The Hidden Cost of Cap Tables
Every individual investor listed on a cap table creates administrative work. Legal filings, shareholder approvals, and document updates all add up. Over time, each name can cost a startup $1,500–$2,000 in legal overhead.

2) The ROFR Problem
Most angels don’t know what a Right of First Refusal (ROFR) actually is. But if you’re on the cap table, you’ll be asked to sign documents tied to it. One confused signature can delay a financing or acquisition.

3) Dilution Isn’t the Enemy
Early investors often obsess over dilution. But if a company is raising new capital and growing, dilution simply means the business is becoming more valuable. Fewer shares at a much higher value is still a win.

4) Influence vs. Impact
Being on the cap table doesn’t give angels meaningful power. The most valuable angels are the ones who help founders with introductions, advice, encouragement, and real-world experience.

The Big Idea

Angel investing works best when it functions as support, not control. Small checks shouldn’t create large operational headaches. Whether through SPVs or thoughtful investment structures, the goal should always be the same: Give founders capital without slowing them down.

Chapters

00:00 Introduction and Collaboration Plans
00:20 Understanding Cap Tables and SPVs
03:35 Dilution and Its Implications for Angel Investors
08:54 Cap Tables vs SPVs — What Actually Matters
18:06 Angels Decoded End Card

The Hosts

Andy Walsh: 2x exited founder and strategist. He helps investors and founders navigate the “power dynamics” of early-stage capital without the fluff.

Cheryl Kellond (aka “Shezza”): 3x founder and CEO of Play Money. She’s on a mission to move accredited professionals from the sidelines into the game with a data-backed, pragmatic approach.

Access All Areas.

Subscribe: Substack

Web: angelsdecoded.com

Resources

Startups Decoded Podcast

AngelList

Ep#3: Why SPVs are the "Professional Grade" Way to Angel Invest.

Andy Walsh — Fri, 27 Feb 2026 07:00:00 -0100

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 "professional" investor.

The reality is sharp: Most individual angels lack the time to manage 1065 tax forms, K-1s, and the endless "Rofer" (Right of First Refusal) documents that flood an inbox during a growth round. By pooling capital into an SPV, you aren't just simplifying your life; you’re de-risking the founder’s future by keeping their cap table clean for institutional VCs.

The "Under the Hood" Realities We Unpack:

The Respect Tax: Every unique name on a cap table costs a founder roughly $1,500–$2,000 in legal overhead over a decade. An SPV collapses that "tax" into a single line item.
The "Black Box" Myth: Traditional SPVs often hide investors from founders. We discuss why transparency, giving founders your contact info while keeping the legal structure separate, is the only way to be a "value-add" angel.
The Cost of Compliance: We get into the middle of fees. Yes, there is a cost to professional management, but it’s a fraction of the "time tax" you'd pay trying to DIY your own legal reviews and tax reporting.

The numbers paint the real story. If you want to support a founder, don't just give them capital, give them optionality and a friction-free path to their next round. This conversation is the roadmap for how to do exactly that.

Chapters

00:00 The Power of Making Multiple Bets
01:56 What is an SPV? (Getting under the hood of the LLC structure)
04:50 Why Direct Cap Table Investing is a "World of Hurt" for Founders
07:50 Navigating Fees: Why "Free" Investing Doesn't Exist
12:52 The Human Element: Building Relationships through Stakeholder Updates

The Hosts

Andy Walsh: 2x exited founder and strategist. He helps investors and founders navigate the "power dynamics" of early-stage capital without the fluff.
Cheryl Kellond (aka "Shezza"): 3x founder and CEO of Play Money. She’s on a mission to move accredited professionals from the sidelines into the game with a data-backed, pragmatic approach.

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com

Ep#2: Why 30 is the Magic Number for Angel Portfolios.

Andy Walsh — Fri, 20 Feb 2026 07:00:00 -0100

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 checks you write. Using data science from AngelList, we explore the "magic number" where angel investing shifts from a gamble to a predictable asset class.

The Hard Truths We Unpack:

The Power Law: Signal is low at pre-seed. You need volume (30–50 companies) to capture the outliers.
The Reinvestment Trap: Reinvesting in "winners" often dilutes returns. Your capital is better spent finding the next new rocket ship.
Sustainable Pacing: You don't "expert" your way out of math. Pacing 6–7 investments a year is the professional standard for a healthy portfolio.

The numbers paint the real story. If you’re looking to move past the "lurking" phase and build a data-backed roadmap for private market investments, this conversation is where it is at.

Chapters

01:09 The Math Behind Angel Investing: Abe Othman’s Data
04:02 The Power of Multiple Bets: Indexing the Market
06:21 The Magic Number: Why 30 is the Threshold
11:20 Infinite Regret: Why Angels Shouldn’t Double Down
15:37 The Shift: From Lottery Ticket to Predictable Asset Class

About the Hosts

Andy Walsh: 2x exited founder, host of Startups Decoded, and strategist helping founders sharpen judgment and execute with speed.

Cheryl Kellond: 3x founder, 3x Ironman, and founder of Play Money, a platform designed to move accredited professionals from "lurking" to "leading" in private markets.

Access All Areas.

Subscribe: Substack
Web: angelsdecoded.com

Ep#1: Beyond the Check: Turning Angel Capital into Strategic Leverage.

ANDY WALSH — Fri, 13 Feb 2026 00:11:07 -0100

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.

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The Death of the “Dumb Money” Myth

For decades, angel investing was seen as a social activity, a philanthropic nod to a friend’s kid or a way to pass time at a luncheon. But the landscape has shifted. Within the last five years, a new wave of operator-led capital has emerged.

This isn’t just money; it’s a strategic lead. Because angel capital isn’t tied to the rigid “billion-or-bust” math of large VC funds, it gives founders the optionality they need to survive the “messy middle” of building a business.

The 20 Million Household Opportunity

There are currently 20 to 25 million US households that meet the criteria for “accredited investor” status. Yet, statistics show that way less than one million have actually made an investment.

According to recent surveys, 75% of accredited investors say they want to invest in startups but don’t know where to start. They are held back by three perceived barriers:

Access: Not knowing where to find high-quality deals.
Knowledge: Not knowing how to evaluate a cap table or a term sheet.
Time: The fear that being an angel requires a full-time commitment.

Play Money: The “Lurk and Learn” Model

Cheryl Kellond, 3x founder, 3x Ironman, and active angel with 50+ companies, is solving this through Play Money. It’s designed to be the “Instagram meets AngelList” for the next generation of investors.

The goal? To allow the millions of people sitting on the sidelines to “get reps” seeing deals without the pressure of an immediate check. By democratizing the “spidey sense” of veteran operators, the platform moves investors from lurking to leading.

The Three Gates of Validation

How do you ensure you aren’t just gambling? Cheryl outlines the three gates every deal on Play Money must pass:

Professional Vetting: The deal usually has a lead investor who manages money for a living.
Operator “Spidey Sense”: The Play Money team evaluates the founder’s resilience and market timing.
Founder Hustle: The founder must prove they can activate their own network before being rolled out to the broader community.

What’s in the Episode?

00:16 – Meet the Hosts: Two Exits and Three Ironmans.
03:17 – The Evolution: From Luncheon Clubs to Strategic Operators.
07:42 – Decoding Accreditation: Income vs. Assets and the rules of self-attestation.
11:20 – The Play Money Model: How to “Lurk and Learn” for free.
18:14 – In Cahoots: Why we’re building this platform now.

Subscribe. Then Decide.

Angel investing is the ultimate craft for those who want to turn capital into cultural and financial impact. This isn’t about noise; it’s about practical intelligence for people who want to own a piece of the future.