Try Again

Hey y’all — here’s today at a glance:

🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Pritesh Kumar on how he almost killed his company by chasing investors (Link)

• Lotanna Ezeike on the mindset shift that helped him close his round (Link)

Growth

• Cody Schneider on how it kills him when founders don’t do paid ads (Link)

• Andrew Gazdecki on the best marketing for startups (Link)

ICYMI

• Find out if your company is enterprise-ready with this practical checklist for B2B SaaS apps (Link)*

• Rubén Dominguez Ibar on the $1B market map (Link)

• David Haber on the value of seeing great early (Link)

• Hubert Thieblot on why startups really fail (Link)

• Tom Bilyeu’s 3-step pay-or-pass idea validator (Link)

• Baxate Carter on why finding co-founders is so hard (Link)

• Yacine Sibous on the dead giveaway to know if a founder will succeed (Link)

💡 Opportunity: AI Meal Planner

No, this isn’t just an idea to have an AI system recommend meals to you based on fitness goals.

Those are commoditized and, also, limited to people who have those fitness goals in the first place.

Let’s tackle a larger market by focusing on saving users money rather than building diet plans.

Instead of telling it about your caloric restrictions, you’d give it a weekly budget and it would scan grocery options near you for sales, prep a weekly menu, and order them for delivery on your behalf.

With respect to Trader Joe’s, most grocery stores are available via Instacart, DoorDash, etc by this point. And Whole Foods is on Amazon.

So you’d need to build a scraper to pull in current prices each week and then an agent to fill up your cart(s) and place the order(s), while considering your preferences for delivery time and likely your GCal availability.

🧠 Framework: The CC/CD Framework

Apple’s App Store was the last paradigm-changing platform shift before LLMs.

If you think comparing the two is hyperbole, you aren’t paying attention.

It’s actually easier to think of LLMs as a platform on top of which you build software. But, obviously, with any platform shift comes new principles for developing said software.

Lenny Rachitsky shared a guest post in his newsletter recently where Aishwarya Naresh Reganti and Kiriti Badam shared the Continuous Calibration/Continuous Development (CC/CD) Framework to try and capture this new way of building:

The article is quite long, so let me quickly break down the framework:

What I like about it is that it basically eschews the idea of “production readiness” and replaces it with a constant tension of agency (for the system) vs control (by you, the builder).

On one side, you have development where you:

1. Scope capabilities & curate data, with milestones by levels of agency (i.e. it can route support tickets, then suggest responses, then auto-resolve)

2. Set up a minimal version of an application with logging, human overrides, and basic guardrails. Your focus here is on observability, not overengineering.

3. Design evals based on your chosen performance metrics

Then launch to a small group of users and calibrate:

1. Run your evals

2. Analyze user behavior and spot errors

3. Apply fixes

Once fixes are applied, return the development side. It’s a continuous, six-stage loop that lets you reduce unpredictable behavior in the system and build trust in its ability to handle agency.

📈 Trend: Budgeting App

Let’s do the math:

1. Financial literacy is up

2. App-based gambling is up

3. Inflation is (still) up

As a result, people are more actively looking to set budgets and manage their money.

Isn’t it shocking, still, that Intuit decided it was a good time to shut down their personal budgeting app, Mint?

Years down the road that decision will look even wilder than it already does.

No wonder you have competitors like Refresh, Monarch, Origin, Copilot, and others all competing for different slices of this market.

I’d like to see an AI-first player enter this space (LMK if you’re using one you like), but I expect we’ll see continued fragmentation in this market for a while before something new takes over broadly. Lots of opportunity to get a slice.

💬 Quote: Try Again

No matter who you are, sometimes it hits you.

The losses. The failures. The almosts.

If just one thing had been different, it all could have been different.

If you’d moved faster, the company would be IPO-ing instead of shut down.

Personally, I’ve seen the depths of failure after the highs of success.

Nothing’s worse. You feel like you let your co-founder(s), your employees, your users, and your investors if you had them all down.

But it’s in those moments where we define ourselves.

Who are you going to be?

After you fail, is that it?

Is that your story?

No one’s going to answer those questions for you.

And the answers aren’t that you’re going to rise up by default.

You have to will it to be so.

You have to decide to own it, and to be more, and to take another shot.

So if you’ve been there or if you’re there right now… dust yourself off.

Get up.

And try again as a slightly wiser captain.

When I left my old startup I had no plan. No money coming in.

But I wasn’t about to give up and go back to big tech.

So I went in on this newsletter.

Now it’s been 2.5 years. We’ll hit $3 million in revenue in the next couple months, totally bootstrapped.

When you’ve built something new, you’ll be thankful you pushed through.

Believe me.

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