Should I Fire Myself?

Hey y’all — events are back! I’m hosting a fireside this Thursday with Rob Schutz, co-founder of Ro.

Here’s today at a glance:

🔗 Houck’s Picks

My favorite finds of the week.

• Learn how Chatsimple's AI Agent increased website engagement by 4X and boosted qualified leads by 30% in just 2 months! Check it out.*

• Why “launch and iterate” doesn’t work in consumer (Link)

• The best reason for startups to raise less money (Link)

• A tip for when you’re telling your story to investors (Link)

• Sam Altman on how much equity to give your first 10 employees (Link)

• The benefits of growing your headcount slowly (Link)

• The most valuable skill needed when building apps (Link)

• Inside Canva’s SEO strategy (Link)

• Steve Jobs best hiring advice (Link)

• A list of 30+ startups that pivoted and why they did (Link)

• 32 rules for being a founder (Link)

💡 Opportunity: Early Clubhouse for Group Chats

Clubhouse in 2020 - early 2021 was a special place.

Clubhouse isn’t part of the cultural zeitgeist at all anymore due to well established problems with the model that made it a sensation at first.

Part of the reason it became a hit, though, was the high-quality curation of the discussions that took place on the app.

In the few years since, those conversations have mostly moved into disconnected groupchats spread across Telegram, WhatsApp, iMessage, Signal, and other messaging platforms.

The Biden years and the global awakening about the internet censorship complex that exists during them have resulted in more people feeling like they’d be better off only sharing their full thoughts in private, trusted spaces.

So… why not build a product to service them?

I love this idea from On Deck’s founder, Erik Torenberg:

With audio rooms, catching up if you join late is impossible. With text, that’s not the case.

You’d need a highly curated initial set of groupchats to make it happen, but you wouldn’t necessarily need to start your own — you’d instead need to convince people to list their existing ones and deeplink into them (with some way for admins to vet requests).

🧠 Framework: Should I Fire Myself?

Marc Andreessen famously said that “if you don’t have anyone on your founding team who is capable of being CEO, then sell your company.”

It’s true early on — having a “professional CEO” is a bad idea. They won’t have as much skin in the game as a founder. There’s a reason founder-led companies grow faster.

With that said, it isn’t true forever.

Speed is your biggest advantage early in your startup’s journey, but the delta between its importance and the importance of other things like

At some point you need to expand your skillset and evolve from “founder” to “CEO,” and not every founder pulls it off.

Even if you’re not the CEO, your actual responsibilities will naturally change as the team expands from under 10 to over 100 or 1,000.

But how do you know when it’s time (if ever)?

Anand Sanwal, the co-founder and former CEO of CB Insights, created a framework to help.

Consider how excited you are about the company’s future and how equipped you are to execute it.

If you fall into quadrant 3 (above), it may be time to consider stepping aside.

📈 Trend: Accountability as a Service

In 2024 you’re more likely than ever to be working:

• On your own company

• Remotely

• On what you actually want to be building

While this can increase your motivation for your work, it also makes you more reliant on yourself for accountability.

As a result, you’re also more likely to be a member of some tribe / community (digitally or IRL).

People join communities for a sense of identity but also, in many cases, that missing sense of accountability.

I’m not sure if there’s a scalable business within this trend, but I’d be curious to hear about anyone who’s pursuing it.

💬 Quote: Steve Jobs on Ideas and Products

The hardest part about being a founder isn’t finding a good opportunity, it’s everything that comes after.

You learn little things every day that you need to remember and piece together into a product. It’s impossible to get it exactly right ahead of time — you need to listen and learn.

This is why being a founder is such an intense “job.”

You need to constantly make the tradeoff between moving as fast as possible and implementing true craftsmanship into your product. You can’t assume either will happen — you need to be in the details with your team and your users on every bit of it.

Steve Jobs talked about the importance of craftsmanship, which clearly came through in Apple’s products during his lifetime:

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