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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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.

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 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

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Hosts

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.

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.

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

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

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.

Listen: Apple | Spotify | YouTube

Subscribe now

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.

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

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.

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: Substack

Web: angelsdecoded.com

Startups Decoded Podcast: startupsdecoded.com

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

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.”

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: Substack

• Web: angelsdecoded.com

• Startups Decoded Podcast: startupsdecoded.com

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

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: Substack

• Web: angelsdecoded.com

• Startups Decoded Podcast - startupsdecoded.com

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

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: Substack

• Web: angelsdecoded.com

• Startups Decoded Podcast
  

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

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

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

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

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

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

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

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

AngelList: https://angel.co

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

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 I 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.

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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.

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Web: angelsdecoded.com

In this second episode, we move from the “why” to the “how” of building a portfolio that actually behaves like a predictable asset class.

The hard truth? One or two bets isn’t a strategy, it’s a gamble. We dive into the data-backed breakthrough that shifted Cheryl from a mentor to a high-volume investor: the realization that the only factor predictive of returns in early-stage startups is the number of checks you write.

Cheryl fan-girls over the “stealth” data science of Abe Othman (AngelList) to explain why the magic number for an angel portfolio starts at 30. We discuss why you can’t “expert” your way out of the math, how to pace your investments to hit 30–50 companies without burning out, and why doubling down on winners might actually be a mistake for the solo angel.

This is a pragmatic look at the statistics of success, designed to help founders and investors understand why angel capital—when diversified—is the most stable foundation for the “messy middle” of a startup’s journey.

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Chapters

• 00:00 The Importance of Portfolio Construction

• 01:09 The Math Behind Angel Investing: Abe Othman’s Data

• 04:02 The Power of Making Multiple Bets: Indexing the Market

• 06:21 The Role of Angels in Early-Stage Startups: Why 30 is the Threshold

• 07:12 The Pacing Plan: 6 Checks a Year vs. The All-In Approach

• 11:20 Infinite Regret: Why Angels Shouldn’t Double Down

• 15:37 The Shift: From Lottery Ticket to Predictable Asset Class

Andy Walsh

Andy is a 2x exited founder and host of Startups Decoded (Top 2% globally), with a track record of scaling companies from concept to $10M+ ARR. A strategist, angel investor, and advisor, he helps founders sharpen judgment and skip predictable mistakes by integrating brand, product, and growth into a clear path to scale. With deep roots in creative and commercial strategy, Andy provides the “holistic edge” founders need to see around corners and execute with speed.

Cheryl Kellond

Cheryl Kellond is a 3x founder, 3x Ironman, and active angel investor with over 50 companies in her portfolio. After selling her previous startups, she realized that the biggest barrier to startup growth wasn’t a lack of founder talent, but a lack of accessible, intelligent “top of funnel” capital.

Today, Cheryl is the founder of Play Money, a platform designed as the “Instagram meets AngelList” for the next generation of investors. She focuses on democratizing access to private markets, helping accredited professionals move from “lurking” to “leading” by leveraging institutional-grade vetting and community-driven validation.

Who Should Listen

• Angels looking to move past the “one-off” investment mindset

• Accredited professionals wanting a data-backed roadmap for startup returns

• Founders wanting to understand the math that drives angel decision-making

• Wealth advisors seeking to explain early-stage risk through a statistical lens

Takeaways

• The Power Law vs. The Numbers Game: At the pre-seed and seed stage, signal is low. You need volume to capture the “moonshot” winners.

• The Magic Number: Returns become predictable once a portfolio hits 30 to 50 investments.

• Abe Othman’s Insight: AngelList data proves that the only factor predictive of returns is the number of startups in the portfolio.

• Infinite Regret: For angels, reinvesting in a “winner” often dilutes returns. Your capital is better spent finding the next new rocket ship.

• Sustainable Pacing: You don’t have to do it all at once. Pacing 6–7 investments a year is the professional standard for a healthy portfolio.

• Information Asymmetry: Why later-stage investments are a “black box” for angels compared to the transparency of the early stages.

Access All Areas.

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Web: angelsdecoded.com

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:

1. Access: Not knowing where to find high-quality deals.

2. Knowledge: Not knowing how to evaluate a cap table or a term sheet.

3. 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.