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Feb 9, 2023 · 21m · founders-journal

How to Crush Investor Updates

Alex Lieberman · 19m spoken Jesse Pujji · 2s spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The Crazy Ones, Alex Lieberman delivers a tactical masterclass on how founders can craft high-impact investor updates that enforce strategic discipline, maintain stakeholder trust, and mobilize investor networks for help. Drawing on operator insights and practical experience, Alex breaks down a clear two-part template designed to communicate financial health, track core goals, and execute targeted asks.

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 99.9% of the talking time here. How this is scored →

Alex as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Alex pushing back 0.0
05100:0010:0020:001:18–8:39 · Alex as informed peer 0/10 The Strategic Value of Investor Updates for Founders Solo host monologue episode. Alex reviews responses from prominent founders and investors regarding how to write an effective investor update.8:39–12:09 · Alex as informed peer 0/10 Core Objectives and Best Practices for Founder Updates Solo monologue where Alex breaks down the three primary goals of writing investor updates and establishes core best practices.12:10–17:54 · Alex as informed peer 0/10 Framework for Section One: The Essential Five-Minute Must-Read Alex details the exact anatomy of Section One of an investor update, covering financials, short-term goal tracking, specific asks, and shout-outs.17:54–20:44 · Alex as informed peer 0/10 Framework for Section Two: The In-Depth Nice-to-Read Alex outlines options for Section Two of an investor update, including deep dives on OKRs, functional breakdowns, and company wins/losses.1:18–8:39 · Guest teaching 0/10 The Strategic Value of Investor Updates for Founders Solo host monologue episode. Alex reviews responses from prominent founders and investors regarding how to write an effective investor update.8:39–12:09 · Guest teaching 0/10 Core Objectives and Best Practices for Founder Updates Solo monologue where Alex breaks down the three primary goals of writing investor updates and establishes core best practices.12:10–17:54 · Guest teaching 0/10 Framework for Section One: The Essential Five-Minute Must-Read Alex details the exact anatomy of Section One of an investor update, covering financials, short-term goal tracking, specific asks, and shout-outs.17:54–20:44 · Guest teaching 0/10 Framework for Section Two: The In-Depth Nice-to-Read Alex outlines options for Section Two of an investor update, including deep dives on OKRs, functional breakdowns, and company wins/losses.1:18–8:39 · Guest disagreement 0/10 The Strategic Value of Investor Updates for Founders Solo host monologue episode. Alex reviews responses from prominent founders and investors regarding how to write an effective investor update.8:39–12:09 · Guest disagreement 0/10 Core Objectives and Best Practices for Founder Updates Solo monologue where Alex breaks down the three primary goals of writing investor updates and establishes core best practices.12:10–17:54 · Guest disagreement 0/10 Framework for Section One: The Essential Five-Minute Must-Read Alex details the exact anatomy of Section One of an investor update, covering financials, short-term goal tracking, specific asks, and shout-outs.17:54–20:44 · Guest disagreement 0/10 Framework for Section Two: The In-Depth Nice-to-Read Alex outlines options for Section Two of an investor update, including deep dives on OKRs, functional breakdowns, and company wins/losses.1:18–8:39 · Alex pushing back 0/10 The Strategic Value of Investor Updates for Founders Solo host monologue episode. Alex reviews responses from prominent founders and investors regarding how to write an effective investor update.8:39–12:09 · Alex pushing back 0/10 Core Objectives and Best Practices for Founder Updates Solo monologue where Alex breaks down the three primary goals of writing investor updates and establishes core best practices.12:10–17:54 · Alex pushing back 0/10 Framework for Section One: The Essential Five-Minute Must-Read Alex details the exact anatomy of Section One of an investor update, covering financials, short-term goal tracking, specific asks, and shout-outs.17:54–20:44 · Alex pushing back 0/10 Framework for Section Two: The In-Depth Nice-to-Read Alex outlines options for Section Two of an investor update, including deep dives on OKRs, functional breakdowns, and company wins/losses.

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

0:00 · Alex 99% · guest 1%0:00 · Alex 99% · guest 1%3:00 · Alex 100% · guest 0%3:00 · Alex 100% · guest 0%6:00 · Alex 100% · guest 0%6:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%9:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%12:00 · Alex 100% · guest 0%15:00 · Alex 100% · guest 0%15:00 · Alex 100% · guest 0%18:00 · Alex 100% · guest 0%18:00 · Alex 100% · guest 0%21:00 · Alex 100% · guest 0%21:00 · Alex 100% · guest 0%
Sharpest disagreement ▶ 1:18 No combativeness present

This is a solo host monologue episode with no guest present to engage in debate.

 Hardest push from Alex ▶ 1:18 No pushback present

This is a solo educational monologue episode without any counter-arguments or debates.

 Biggest teaching moment ▶ 1:18 No schooling present

There is no guest present in this solo monologue episode to educate or correct the host.

 Alex holds their own ▶ 12:10 Alex breaks down the one-liner communication tactic

Alex demonstrates operational expertise by explaining why founders must provide a crisp one-liner for investors to parrot to their networks.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
The Strategic Value of Investor Updates for Founders 0000 Solo host monologue episode. Alex reviews responses from prominent founders and investors regarding how to write an effective investor update.
Core Objectives and Best Practices for Founder Updates 0000 Solo monologue where Alex breaks down the three primary goals of writing investor updates and establishes core best practices.
Framework for Section One: The Essential Five-Minute Must-Read 0000 Alex details the exact anatomy of Section One of an investor update, covering financials, short-term goal tracking, specific asks, and shout-outs.
Framework for Section Two: The In-Depth Nice-to-Read 0000 Alex outlines options for Section Two of an investor update, including deep dives on OKRs, functional breakdowns, and company wins/losses.

Statements from this episode (6)

Insight
Alex Lieberman: Writing regular investor updates makes founders better operators
“I believe that founders are better operators when they write investor updates. It is so incredibly easy to get stuck in the weeds just doing, doing, doing when you're running a business, especially in the early days, and the act of writing recurring investor u…”
Alex Lieberman Feb 9, 2023 ▶ 1:46
Assertion Contradicted
Lieberman: Ramp reached $100M ARR faster than any company
“Ramp is I believe the fastest growing company to go from zero to a hundred million in ARR.”
Alex Lieberman Feb 9, 2023 ▶ 6:43
Disclosure
Lieberman: Early on at Morning Brew, I failed to ask investors for help
“Is I was terrible in the early days of Morning Brew of leveraging advisors or investors to ask them for help.”
Alex Lieberman Feb 9, 2023 ▶ 9:35
Insight
Lieberman: Founders must keep investor updates under a five-minute read
“And the third rule of thumb, try to keep your investor update under a five minute read. Beyond that, you lose people's attention, and feel free to have an internal version of your update that's more thorough, that just kind of forced you to go through the full…”
Alex Lieberman Feb 9, 2023 ▶ 11:47
Insight
Lieberman: Investor updates should never include more than three asks
“Don't include more than three asks. Beyond that, people don't have a sense of what's important.”
Alex Lieberman Feb 9, 2023 ▶ 15:43
Insight
Lieberman: Gamifying investor updates exploits their natural competitiveness
“Because just like entrepreneurs, Investors are competitive. They like being atop the leaderboard. And so if you can gamify and create a leaderboard on your monthly or quarterly investor update, they are going to be motivated to add value because they want t…”
Alex Lieberman Feb 9, 2023 ▶ 16:55
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