We Are So Back

And why founders struggle to explain their product

Hey y’all — here’s today at a glance:

Opportunity → AI Email Churn Predictor

Framework → Why Founders Struggle to Explain their Product

Tool → Cimphony AI

Trend → Software Development Jobs

Quote → We Are So Back

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

  • Peter Walker on Series A valuations by ecosystem (Link)

  • Alejandro Cremades on uninvestable cap tables (Link)

  • Karim Boussedra’s top 10 non-dilutive financing options (Link)

Growth

  • Amanda Zhu on why you should stop tracking metrics if under $1M ARR (Link)

ICYMI

  • Join Copy.ai and others who swear by Arc.dev as a "huge shortcut" for hiring pre-vetted remote talent fast.*

  • Jonas Baum on things he messed up on his last startup (Link)

  • Rubén Domínguez Ibar on a16z's favorite AI apps (Link)

  • Ilya Strebulaev on top 50 VC firms by number of unicorn investments (Link)

  • Muhammed Umar on the Collison brothers' biggest mistake (Link)

  • Andrew Gazdecki’s acquisition tip (Link)

💡 Opportunity: AI Email Churn Predictor

Little is more valuable that knowing with certainty how likely customers are to stick around vs churn.

I’m always looking for ways to better predict retention.

One idea would be using LLMs to analyze email conversations, Intercom interactions, or Slack messages if you have shared channels set up with customers to score how likely each individual customer is to churn.

While this probably won’t lead to a venture-scale business, I see it as an easy opportunity for a profitable micro SaaS.

And it may actually be even more valuable for large teams than small ones, since customer interactions may be spread across more surfaces.

🧠 Framework: Why Founders Struggle to Explain their Product

I hate writing copy for landing pages.

Traditionally my pages have converted pretty well, but it takes me forever to write them because I’m too close to the product and it’s a challenge to go up to a customer-level altitude when talking about it in such a static way.

But that’s not the only reason founders struggle to explain what their product or offer actually does… here are five, and why they happen:

And here are my solutions for each:

  • Curse of Knowledge → Simplify your messaging by focusing on customer pain points, not technical details, using clear and jargon-free phrasing.

  • Moving Target → Build a process to regularly update your messaging. Continuously test and iterate with customer feedback. Make it part of your DNA.

  • The Platform Challenge → Prioritize core features in your messaging and communicate one primary value proposition clearly. You might be doing too much.

  • The Sunk Cost Fallacy → Ruthlessly cut underperforming features. Focus your messaging on what delivers real customer value.

  • Focused on Vision → Realize your customers are not looking at your product like an investor. Craft customer-centric messaging that highlights immediate benefits, not your longterm vision.

🛠 Tool: Cimphony AI

Don’t get a second-rate lawyer.

Startups move fast. Lawyers don’t.

Old-school firms charge $800/hour to do slow, bloated work.

You’re building, closing deals — you don’t have time for that.

Cimphony delivers real legal work at startup speed: flat rates, no hidden fees.

General Counsel, Fundraising, IP, cap tables — fast, clean, founder-friendly.

Hundreds of startups are already using Cimphony. $100K in fees deferred if you need it.

📈 Trend: Software Development Jobs

Founders: be honest here.

Are you likely to hire more or fewer engineers now than you would have before the rise of LLMs?

The only way I see the answer to that being “yes” for most of you is if it’s as a result of automating more other roles (customer support, ops, etc) as a result of LLMs.

That’s why it’s not surprising to see this chart about how many job listings exist for engineers over the last few years:

Maybe you’ve seen this chart. It’s been circulating for the last year or so. And each time the volume has gone down slightly more.

Many people see this and jump to the conclusion that Cursor, Devin, etc are making engineers obsolete.

While I agree that people will do less coding as AI continues to improve, I actually think the real takeaway here is that thinking like an engineer and understanding how systems are built will become important for a larger group of people.

For example, this week I’ve been working on some AI workflows for our business and once you start working with these systems it’s immediately clear that writing good prompts not only means understanding how a process is done but also how to describe that to a machine.

It sounds simple but if I hadn’t started my career as an engineer, I don’t think I’d be anywhere near as good at prompting.

So I’d expect this chart to reverse course, though the jobs may have different titles than “software engineer.”

💬 Quote: We Are So Back

It can actually be fun to emphasize the highs and lows with a startup. Tweets like this are funny:

But I always try to be mindful to never feel either one of those things too much.

The bumps and the wins will come and go, but letting your emotional state oscillate back and forth will drive you nuts, stress you out, and undermine your ability to focus.

The “in-between” is actually where you should keep yourself 99% of the time.

It’s never over, and you’re never back — you’re just on a mission.

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