Compete On The Problem

Be essential for your customers

Hey y’all — here’s today at a glance:

Opportunity → AI Matchmaker For Student-Tutor Pairings

Framework → Google’s HEART Framework

Tool → Sidekick

Trend → 30 Year Old Life Readiness

Quote → Compete On The Problem

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

  • Ray De Leon on how to protect your ownership while raising capital (Link)

  • Ashish Saboo on what founders should know before investor meetings (Link)

  • Jorian Hoover on how to stay organized during a fundraise (Link)

Growth

  • Mostly Metrics shares the playbook to forecasting pipeline at scale (Link)

  • YC’s Tom Blomfield shares the sales playbook for founders (Link)

  • Jason Shuman shares PMF data through vertical AI demo to close rates (Link)

ICYMI

  • Find newsletter subscribers who already want your content (Link)

  • Paul Stansik on why nailing your ICP is hard (Link)

  • Alex Nguyen on the 5 core skills every founder needs (Link)

  • Alejandro Cremades on startup compensation (Link)

  • Deedy Das on the most common mistake young founders make (Link)

💡 Opportunity: AI Matchmaker For Student-Tutor Pairings

From private gradeschools to elite universities, it seems that as the prices rise so does the competitiveness required to get in.

And there’s an incredibly limited amount of time for parents to get it right for their kids.

This is a scenario where the customers are money rich and time poor, with a huge willingness to pay.

Why not build an LLM-based system that interviews them and their kids about where they are in their learning and what their goals are, and then recommends a personalized list of tutors specifically for them?

You could charge an upfront fee to the parents and then later, once you’ve built up credibility in the space, onboard the tutors to your platform and take commission as well.

🧠 Framework: Google’s HEART Framework

Why do your users keep coming back to your product or service?

Google developed the HEART framework to help product builders (or founders, in our case) go beyond what users do and the data we collect, but also understand how they feel, what they love, and where they have issues.

If you couldn’t guess, it was developed by a UX research team. UX sometimes gets a bad rap in big tech as being impractical but I always found the opposite, and the UX mindset is one of the most important skills I took with me from my Uber and Airbnb days to being a founder.

The framework offers you five different lenses through which you can view whether your product is successful or not for the people actually using it:

Let’s break these down briefly.

  1. Happiness → measured by satisfaction (NPS or PMF score — here’s my breakdown of the two) and critical for referral or brand-first products.

  2. Engagement → how often, how much, and how deeply are your users using the product? Measured through usage metrics, cohort analysis, and usually centered around key actions you want users to take that indicate stickiness.

  3. Adoption → Engaging is one thing, but actually getting value is another. Measured by conversion rates and duration metrics (i.e. time to value) often starting with activation. Look for where people are dropping off.

  4. Retention → Without this, nothing else you do will result in a stable business. Measured by cohort analysis, and churn vs expansion. Look for the key indicators either in demographics or usage that correlate with better retention.

  5. Success → Does your product let users actually do what it promises? Can they get out of it what they want? Is that easy for them? Measured by time spent, completion rate, and similar metrics. Tools like Posthog help here — watch their journeys.

🛠 Tool: Sidekick

LLMs birthed a whole new generation of workflow automation tools.

No longer were Zapier and Make’s ability to link together tools enough. Users wanted to be able to create workflows that natively called and prompted LLMs with various settings.

Tools like Gumloop, Lindy.ai, n8n, and my personal favorite — Plumb were born.

Sidekick takes it one step further by creating your workflows for you, all you need to do is use their chat interface.

Worth noting that Zapier tried to implement something similar but lacks the ease of user with LLM nodes that the new generation of tools have. I’m interested to see if Sidekick start becoming a go-to.

📈 Trend: 30 Year Old Life Readiness

I’ve been thinking about this chart ever since it went viral earlier this month:

In case you hadn’t seen it… yes, you read it right.

In the last 35 years the amount of 30 year olds in the US who are married and own a home has dropped from 45% to ~10%.

There’s a lot to potentially dig into here, but overall what it’s implying for founders is simple:

Moreso than ever before, new ideas are needed to make traditional families achievable for the average person.

That extends at a surface level from dating and housing all the way down to quelling anxiety about the financial impact of those things and the perceived tradeoffs millennials and zoomers feel they must make in exchange.

These are deeply rooted, genuine concerns that don’t have easy solutions but do present both an imperative and opportunity to help solve them.

💬 Quote: Compete On The Problem

Users will forgive you for anything else if you’re the one they trust to deliver.

The one they believe understands their needs.

The one who can solve their problem best.

The one who can make their lives easier.

Don’t make them choose your product out of spite.

Don’t make them choose your product to save a few bucks, even though they really don’t want it.

Don’t be the used car.

Be the Mercedes. Be the Tesla. Be the Koenigsegg or even the Hyundai if that’s what the market calls for.

Compete on the problem.

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