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Say The Thing
And why you should optimize for engagement over outcomes
Hey y’all — here’s today at a glance:
Opportunity → New Chartable
Framework → Say the Thing
Tool → Sharbo
Trend → Time Til Fundraise
Quote → Engagement vs Outcomes
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🔗 Houck’s Picks
My favorite finds of the week.
Duckbill is an AI executive assistant for your personal life. Hand off the things you dread so you can focus on what matters. Enter HOUCK50 for 50% off your first 2 months and priority off of the waitlist.*
My friend launched the most comprehensive fundraising course I’ve seen this year — super actionable insights on what VCs look for in benchmarks, diligence, and more (Link)
Anatomy of high-converting landing pages (Link)
A guide on making high-converting UGC ads (Link)
10 things this failed founder wishes they would’ve done differently (Link)
The best way to give raises to employees when the company is doing well (Link)
3 myths about going public that should die (Link)
Hot takes on how to be an effective CEO from a SaaS founder (Link)
🔥 Deep Dive: How to Leverage Your Network & Community
Each week I interview successful founders for the Founding Journey podcast, and I noticed a lot of them have talked about how community and relationships impacted their startup.
I also shared notes from my own journey building a community that was backed by a16z and other great investors in this deep dive:
Or check it out on YouTube, Spotify, or Apple Podcasts.
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💡 Opportunity: New Chartable
It’s a tale as old as Silicon Valley…
Big company acquires good startup or builds useful product
Big company shuts it down
????
New startups come along to capture the same opportunity
You’ve probably seen Google do this a hundred times (I still haven’t gotten over Google Domains being shut down…)
Right now we’re at step #3 with Chartable, a popular platform for podcast analytics and attribution.
The playbook is right there, this market will be snapped up again quickly.
Greg Isenberg outlined a simple way to attack it:
🧠 Framework: Say the Thing
Being nice is good, making sure people are comfortable is not necessarily good at a startup.
Shopify’s COO sent this note to his team early on, after realizing that people were more concerned with not offending each other than getting to the truth of problems they were trying to solve.
It’s an incredible and concise statement that more companies would benefit from.
At a startup, there’s no reason to sugarcoat things. The less honest you are with your team, your co-founders, and yourself the more likely you are to fail.
I’ve worked closely with people who didn’t understand this but, trust me, with regard to whatever discomfort you’re worried you or someone else will feel… well, failure is worse.
🛠 Tool: Sharbo
Only the paranoid survive.
Founders shouldn’t be obsessed with their competitors, but they should be aware of them. Build for your users, but understand how they’re seeing your position in the market.
Sharbo lets you set up agents to monitor and alert you about what your competitors are doing.
📈 Trend: Time Til Fundraise
A new report from Pitchbook highlights an interesting trend: startups are waiting longer to raise their next round, on average, across the whole spectrum of stages.
In both early and late stage VC, it’s the longest in well over a decade.
There are a couple reasons for this:
AI tools are making it easier for founders to do more with less capital
More founders are preferring organic content marketing over paid growth
There are zombies out there from the ZIRP era raising late down rounds
My own speculation is that, after two years of rising, this will decrease in 2025 due to more bullish sentiment among both LPs and GPs, and the beginnings of a reduction in regulations in the US due to DOGE. More capital, more opportunities!
💬 Quote: Engagement vs Outcomes
As I’ve started making video content for YouTube recently I’ve put roughly equal amount of thought into how to package each video (thumbnail, title, and first 30 seconds / 1 minute) as I have into the actual content of the video.
The same is true of any content platform — on Twitter, your hook matters more than the rest of the thread.
This is also true in startups. You need to sell the value of the product, and then keep them engaged, as much as if not more than actually deliver an outcome.
That may sound sacrilegious, but here’s the co-founder of Duolingo saying it too 🙂
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