Overview
Based on "The Hard Thing About Hard Things" by Ben Horowitz. The core principle: the CEO's job is to manage the truth - not spin it, not hide it, and not dump it unfiltered. Investor updates are trust infrastructure. Horowitz argues that great CEOs communicate bad news faster than good news, ask for help specifically, and never let investors be surprised. An update that only reports wins trains investors to distrust you the moment things go wrong.
Workflow
Step 1: Pull the numbers before writing a word
Collect the following before drafting:
Metrics section (include all that apply to [your startup]):
- MRR or ARR and month-over-month change (absolute and percentage)
- New customers added and churned this period
- Burn rate and runway (months remaining at current burn)
- Cash in bank
- Key product metrics (DAU, activation rate, NPS, or whatever your north star is)
- Pipeline (if B2B): qualified deals, average deal size, sales cycle length
Do not estimate. If a number is not ready, note it explicitly and send the update anyway. "We are still closing the books on MRR - will send an addendum Friday" is better than delaying the whole update.
Step 2: State the headline in the first sentence
Investors read dozens of updates. Your first sentence should tell them whether this is a good month, a hard month, or a turning-point month.
Format options:
- Good month: "[Month] was [your startup]'s strongest month to date. MRR hit $[X], up [Y]% MoM."
- Hard month: "[Month] was difficult. We missed our MRR target by [X]% and I want to explain what happened."
- Turning point: "We made a significant strategic change in [month] that will affect how you read these numbers going forward."
Do not bury the lead. Do not open with pleasantries.
Step 3: Write the wins section (3-5 bullets)
Concrete, specific, measurable:
- "Closed [Company type] as a customer at $[ARR]. This is our first [industry] logo."
- "Shipped [feature]. Early data: [metric] improved [X]%."
- "Hired [role]. [One sentence on why this person matters]."
Avoid: "We made great progress on product" / "The team is energized."
Step 4: Write the struggles section (2-4 bullets)
This is the section most founders skip. Horowitz is explicit: skipping it destroys trust.
Be specific about what is not working:
- "Churn this month was [X]%, above our [Y]% target. Root cause: [specific reason]. Fix in progress: [what you are doing]."
- "Enterprise sales cycle is running [X] weeks vs. [Y] weeks expected. We are [specific adjustment]."
- "We missed the [feature] ship date by [X] weeks. [Why]. New target: [date]."
The struggles section is also where you build credibility. Investors who see you name problems accurately trust your wins more.
Step 5: Write the asks section
This is the highest-value section and the most neglected. Horowitz's advice: investors want to help but they do not know how unless you tell them exactly what you need.
Format each ask as a specific, actionable request:
- "Intro to VP of Engineering at [company type] - we are trying to close a key hire."
- "Anyone who has sold into [industry vertical] and can share their procurement process experience."
- "Feedback on our pricing page - link here: [URL]. Specifically: does the enterprise tier feel defensible?"
Maximum 3 asks per update. Vague asks ("Let me know if you can help with anything!") get zero responses.
Step 6: State the focus for next period
One paragraph. Three priorities maximum.
Format: "In [next month/quarter], we are focused on: (1) [specific goal with metric], (2) [specific goal with metric], (3) [specific goal with metric]."
This closes the update and creates accountability for the next one. Investors will remember what you said you would do.
Anti-Patterns
1. Only sending updates when things are good
Bad: Sending 3 updates when MRR is up, then going silent for 2 months during a hard stretch.
Good: Sending updates on a fixed cadence regardless of whether the news is good or bad. Hard-month updates build more trust than good-month ones.
2. Vanity metrics without context
Bad: "We had 50,000 sign-ups this month!"
Good: "50,000 sign-ups, 1,200 activated (2.4% activation rate). Activation is the problem we are solving in Q[X]."
3. Burying bad news in the middle
Bad: Three paragraphs of wins, then a brief mention that "churn was a bit high", then more wins.
Good: If churn is the real story, put it in paragraph two. Name it clearly.
4. Generic asks
Bad: "Let us know if you can make any intros!"
Good: "We need an intro to a Head of Revenue at a Series B or C SaaS company who has scaled from $1M to $5M ARR. Specifically someone who has built an outbound motion."
Quality Checklist