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Apr 25, 2022 · 20m · founders-journal

How to Think About Angel Investing

Alex Lieberman · 10m spoken Codie Sanchez · 8m spoken
0:00 / 0:00

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Entrepreneurs Alex Lieberman and Codie Sanchez break down their strategic frameworks for angel investing, discussing how to leverage asymmetric advantages like audience distribution, treat early check sizes as educational investments, and deliver distinct, high-impact value to founders.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 55.6% of the talking time here. How this is scored →

Alex as informed peer 6.0 Guest teaching 4.0 Guest disagreement 2.8 Alex pushing back 2.6
05100:0010:0020:000:33–3:23 · Alex as informed peer 5/10 Leveraging Unfair Advantages in Deal Flow and Access Codie explains using unfair advantages in deal terms rather than solely relying on capital. Alex offers slight pushback by asking if audience distribution itself already guarantees proprietary deal flow.3:23–7:50 · Alex as informed peer 7/10 Principle One: Investing in Yourself and the Virtuous Feedback Cycle Alex articulates his detailed virtuous cycle framework linking building, content creation, audience growth, and angel investing. Codie fully endorses the model and adds her own hiring analogy.7:50–9:56 · Alex as informed peer 5/10 Check Sizes, Risk Tolerance, and the Learning Budget Codie challenges Alex's conservative 10k check size, stating it provides insufficient skin in the game for material returns. Alex defends his stance by framing the capital allocation as an educational budget.9:56–15:48 · Alex as informed peer 7/10 Principle Two: Adding No-Bullshit Value to Portfolio Companies Alex outlines his second principle of offering specific, no-bullshit value to tier-one VC portfolio companies. Codie enthusiastically validates the strategy and notes she intends to adopt the tactic herself.15:48–19:35 · Alex as informed peer 6/10 Navigating Skill Stacks, Identity, and the Strategic Wedge Alex discusses his internal struggle with being pigeonholed as merely a digital media expert. Codie educates him on using narrow positioning as an initial wedge before expanding out skill stacks.0:33–3:23 · Guest teaching 4/10 Leveraging Unfair Advantages in Deal Flow and Access Codie explains using unfair advantages in deal terms rather than solely relying on capital. Alex offers slight pushback by asking if audience distribution itself already guarantees proprietary deal flow.3:23–7:50 · Guest teaching 2/10 Principle One: Investing in Yourself and the Virtuous Feedback Cycle Alex articulates his detailed virtuous cycle framework linking building, content creation, audience growth, and angel investing. Codie fully endorses the model and adds her own hiring analogy.7:50–9:56 · Guest teaching 6/10 Check Sizes, Risk Tolerance, and the Learning Budget Codie challenges Alex's conservative 10k check size, stating it provides insufficient skin in the game for material returns. Alex defends his stance by framing the capital allocation as an educational budget.9:56–15:48 · Guest teaching 3/10 Principle Two: Adding No-Bullshit Value to Portfolio Companies Alex outlines his second principle of offering specific, no-bullshit value to tier-one VC portfolio companies. Codie enthusiastically validates the strategy and notes she intends to adopt the tactic herself.15:48–19:35 · Guest teaching 5/10 Navigating Skill Stacks, Identity, and the Strategic Wedge Alex discusses his internal struggle with being pigeonholed as merely a digital media expert. Codie educates him on using narrow positioning as an initial wedge before expanding out skill stacks.0:33–3:23 · Guest disagreement 3/10 Leveraging Unfair Advantages in Deal Flow and Access Codie explains using unfair advantages in deal terms rather than solely relying on capital. Alex offers slight pushback by asking if audience distribution itself already guarantees proprietary deal flow.3:23–7:50 · Guest disagreement 1/10 Principle One: Investing in Yourself and the Virtuous Feedback Cycle Alex articulates his detailed virtuous cycle framework linking building, content creation, audience growth, and angel investing. Codie fully endorses the model and adds her own hiring analogy.7:50–9:56 · Guest disagreement 5/10 Check Sizes, Risk Tolerance, and the Learning Budget Codie challenges Alex's conservative 10k check size, stating it provides insufficient skin in the game for material returns. Alex defends his stance by framing the capital allocation as an educational budget.9:56–15:48 · Guest disagreement 2/10 Principle Two: Adding No-Bullshit Value to Portfolio Companies Alex outlines his second principle of offering specific, no-bullshit value to tier-one VC portfolio companies. Codie enthusiastically validates the strategy and notes she intends to adopt the tactic herself.15:48–19:35 · Guest disagreement 3/10 Navigating Skill Stacks, Identity, and the Strategic Wedge Alex discusses his internal struggle with being pigeonholed as merely a digital media expert. Codie educates him on using narrow positioning as an initial wedge before expanding out skill stacks.0:33–3:23 · Alex pushing back 4/10 Leveraging Unfair Advantages in Deal Flow and Access Codie explains using unfair advantages in deal terms rather than solely relying on capital. Alex offers slight pushback by asking if audience distribution itself already guarantees proprietary deal flow.3:23–7:50 · Alex pushing back 1/10 Principle One: Investing in Yourself and the Virtuous Feedback Cycle Alex articulates his detailed virtuous cycle framework linking building, content creation, audience growth, and angel investing. Codie fully endorses the model and adds her own hiring analogy.7:50–9:56 · Alex pushing back 4/10 Check Sizes, Risk Tolerance, and the Learning Budget Codie challenges Alex's conservative 10k check size, stating it provides insufficient skin in the game for material returns. Alex defends his stance by framing the capital allocation as an educational budget.9:56–15:48 · Alex pushing back 1/10 Principle Two: Adding No-Bullshit Value to Portfolio Companies Alex outlines his second principle of offering specific, no-bullshit value to tier-one VC portfolio companies. Codie enthusiastically validates the strategy and notes she intends to adopt the tactic herself.15:48–19:35 · Alex pushing back 3/10 Navigating Skill Stacks, Identity, and the Strategic Wedge Alex discusses his internal struggle with being pigeonholed as merely a digital media expert. Codie educates him on using narrow positioning as an initial wedge before expanding out skill stacks.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 39.7% · guest 60.3%0:00 · Alex 39.7% · guest 60.3%3:00 · Alex 89.1% · guest 10.9%3:00 · Alex 89.1% · guest 10.9%6:00 · Alex 35.3% · guest 64.7%6:00 · Alex 35.3% · guest 64.7%9:00 · Alex 95.9% · guest 4.1%9:00 · Alex 95.9% · guest 4.1%12:00 · Alex 42% · guest 58%12:00 · Alex 42% · guest 58%15:00 · Alex 41.6% · guest 58.4%15:00 · Alex 41.6% · guest 58.4%18:00 · Alex 41.2% · guest 58.8%18:00 · Alex 41.2% · guest 58.8%
Sharpest disagreement ▶ 8:33 Codie rejects Alex's check size strategy

Codie bluntly tells Alex that writing 10k checks gives him no real skin in the game and will fail to deliver material outcomes.

 Hardest push from Alex ▶ 2:40 Alex challenges Codie's creator investing critique

Alex pushes back on Codie's claim by questioning whether having audience distribution is already an unfair advantage in securing deal access.

 Biggest teaching moment ▶ 17:03 Codie educates Alex on skill stacks and the wedge concept

Codie reframes Alex's anxiety about being boxed into media, showing how specialized positioning acts as a wedge before revealing broader capabilities.

 Alex holds their own ▶ 4:00 Alex outlines his full-stack builder framework

Alex methodically breaks down his proprietary flywheel showing how business building, content creation, audience, and deal flow reinforce one another.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Leveraging Unfair Advantages in Deal Flow and Access 5434 Codie explains using unfair advantages in deal terms rather than solely relying on capital. Alex offers slight pushback by asking if audience distribution itself already guarantees proprietary deal flow.
Principle One: Investing in Yourself and the Virtuous Feedback Cycle 7211 Alex articulates his detailed virtuous cycle framework linking building, content creation, audience growth, and angel investing. Codie fully endorses the model and adds her own hiring analogy.
Check Sizes, Risk Tolerance, and the Learning Budget 5654 Codie challenges Alex's conservative 10k check size, stating it provides insufficient skin in the game for material returns. Alex defends his stance by framing the capital allocation as an educational budget.
Principle Two: Adding No-Bullshit Value to Portfolio Companies 7321 Alex outlines his second principle of offering specific, no-bullshit value to tier-one VC portfolio companies. Codie enthusiastically validates the strategy and notes she intends to adopt the tactic herself.
Navigating Skill Stacks, Identity, and the Strategic Wedge 6533 Alex discusses his internal struggle with being pigeonholed as merely a digital media expert. Codie educates him on using narrow positioning as an initial wedge before expanding out skill stacks.

Statements from this episode (9)

Disclosure
Sanchez: Avoids investing without securing unfair deal terms
“I try to not do deals where I don't have some unfair term.”
Codie Sanchez Apr 25, 2022 ▶ 2:06
Insight
Sanchez: Capital is cheap, but introductions and audience are not
“Because capital right now is cheap, but introductions and audience are not.”
Codie Sanchez Apr 25, 2022 ▶ 2:31
Insight
Sanchez: Do not use angel investing to build early wealth
“In fact, it's why I don't think that most people should angel invest until they have some money. Like, I do not think angel investing is the way to become rich or wealthy early. Like you need to maximize your earnings. You need to get cashflow because you don'…”
Codie Sanchez Apr 25, 2022 ▶ 7:27
Opinion
Lieberman assigns a 25% to 50% chance Bitcoin goes to zero
“The amount of money I have in Bitcoin, I have to be okay with that going to zero because there is a, you know, what I would personally assign a 25 to 50% chance of that happening.”
Alex Lieberman Apr 25, 2022 ▶ 8:23
Opinion
Sanchez: $10k angel checks will not yield material financial outcomes
“I would probably say like, you need to get a little bit more in the deals because none of them will have a material outcome. I mean, you'll have to have a thousand X and even then, you know, it'll be really interesting, but that's like unlikely.”
Codie Sanchez Apr 25, 2022 ▶ 8:55
Disclosure
Lieberman treats his $150k annual angel budget as an expensive education
“I almost look at say the hundred to 150 K I allocate a year as Hopefully the shit goes up, but it is also an expensive version of education to get better at picking and to accumulate better deal flow.”
Alex Lieberman Apr 25, 2022 ▶ 9:38
Opinion
Lieberman: Tiger Global Wins Deals on Capital Speed and Higher Premiums
“Why do the tigers of the world win deals is because they were, they are faster than anyone with their capital, and they're willing to pay higher premiums than anyone with their capital, but generally, capital is commoditized”
Alex Lieberman Apr 25, 2022 ▶ 10:45
Disclosure
Lieberman trades free marketing advice for deal flow at top VCs
“I've become close through Twitter with a lot of top tier partners at Andreessen and at tribe and at these different companies. And I basically say, look, I don't know jack shit about SAS. I don't know jack shit about B to B SAS. I don't know jack shit about sp…”
Alex Lieberman Apr 25, 2022 ▶ 12:35
Insight
Sanchez: Founders Should Poach Talent From Competitors Whenever Possible
“If you can steal from your top competitor, you should.”
Codie Sanchez Apr 25, 2022 ▶ 15:18
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