How to Know You're Ready to Go All In

And why you should fix your product, not your support

Hey y’all — here’s today at a glance:

Opportunity → Streamlining the Startup Stack

Framework → How to Know You’re Ready to Go All In

Tool → Supademo

Trend → Falling Fertility Rates

Quote → Fix Your Product, Not Your Customer Support

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

  • The playbook to selling lifetime deals to fund your startup (Link)

Growth

  • How to deal with seasonal revenue and churn trends (Link)

ICYMI

  • Transform your industry insights into powerful content. At Startup Cookie, we host webinars and repurpose them into engaging videos, insightful blog posts, and compelling social media content. (Link)*

  • Why Jeff Bezos says it’s ok to “wander” (Link)

  • Useful prompt engineering strategies (Link)

  • Sam Altman on why you should bet on AI improvements (Link)

  • A series of guides on all things startup building (Link)

  • Chris Dixon on good startup ideas and where to find them (Link)

  • A list of random but mostly true observations on Silicon Valley (Link)

  • Having a technical co-founder from outside the US can work (Link)

  • Useful guides from Wing VC (Link)

💡 Opportunity: Streamlining the Startup Stack

How can you get experts to share the knowledge that’s stuck in their heads?

An interesting approach to this is Founder Stack, from Alex Lieberman (co-founder of Morning Brew).

Yes, it’s just a Google Sheet for now but it could grow into the vision Gaby outlined in the X post above.

Another is Sam’s List from The Hustle’s founder, Sam Parr, with a more robust UI but focused exclusively on accountants for now.

The larger trend here is new ways for experts to share the knowledge that’s locked inside their heads.

The old guard in the space is services like Tegus and GLG. It’s a high-margin space that’s in need of some disruption — but the challenge is that existing services have established themselves as known quantities, and their businesses have network effects.

A good strategy is to start at the low-end of the market like the above examples are doing, but these are just side projects for both of them — a full-time team could move faster.

🧠 Framework: How to Know You’re Ready to Go All In

Going all-in on an idea is the most important decision a founder has to make, like I wrote about last year.

Andrew Rea’s framework (reposted here), outlines 5 factors you should consider when making the decision:

All are important, but I’d rank the importance of them like this (from most to least important):

  1. Health → You’re not going to get far without this (though you don’t need to be Bryan Johnson to build a startup).

  2. Confidence → Maybe a surprising pick, but when things get hard you need to believe you’ll get out of it.

  3. Judgement → You’ll make wrong decisions no matter how good your judgement is, but things like picking what to work on in the first place and navigating that path can be huge assets to avoid wasting time.

  4. Financial savings → In some ways having less saved can help you prioritize revenue and building a good business right away, but it gives you much less room to be wrong or explore larger ideas.

  5. Skills → Your ability to learn quickly is more valuable than any specific skill… by a lot.

🛠 Tool: Supademo

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📈 Trend: Falling Fertility Rates

If we don’t have enough babies, humanity will die out.

That may sound overdramatic but it’s a simple fact, and many countries have trendlines that don’t look great right now:

Jack Raines did a good deep dive on this trend, but the crux is that it’s a cycle that’s hard to break out of once a society falls too deep into it, and even though it may not feel like it, we’re getting closer to that threshold.

Government incentives to promote having children, and reducing the hold regulatory bodies have on captured industries may help lower the cost of living to a degree where more people feel able to have children, but the deeper change is just making people aware that we all have a part to play in this and it’s later than we think.

So… how can founders help?

Increasing productivity through automation is a way to fight back against inflation and high costs of living. The more founders focused on making everyday life and products cheaper for people, the more time and money they’ll have on their hands to feel comfortable raising kids.

💬 Quote: Fix Your Product Not Your Customer Support

A counterintuitive tip about startups is that more customer support tickets are a sign of product market fit.

If users didn’t love the solution your product was offering to a painful problem, they wouldn’t care enough to write in support tickets. And more tickets = more users.

But when support tickets grow at an exponential rate, they become a problem where you simply can’t get to all of them and still work on the product, growing it, managing the team, talking to investors, etc.

So how do you solve that?

Most people’s first instinct is to hire a customer support person, but this is almost always the wrong first move:

  1. You take yourself further away from your users, making it more complex to understand their issues.

  2. If your startup keeps growing, you’ll just have the same problem again soon.

Instead, take Jessica Livingston’s advice (below) and focus on making the product better.

💡 How I Can Help

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