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And I’m actively involved with everyone we work with. Unlike many other creator-led agencies, I’m not just a frontman who’s going to hand you off to an account manager.

Anyway, here’s today at a glance:

Opportunity → HVAC Failure Maintenance Platform

Framework → The 4-Question Close Framework

Tool → Radiant

Trend → Generative AI 3 Years In

Quote → People Pay To Stop Feeling Pain

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

  • Arohi Jain on how many LOIs You Need To Raise $1M (Link)

  • Leon Eisen shares 9 Fundability Upgrades (Link)

  • Evan H. Fisher on how top founders handle fundraising (Link)

  • Olivia O’Sullivan on how fundraising isn’t a one-way interview (Link)

Growth

  • Jon Brosio on what a good funnel is like (Link)

  • Lenny Rachitsky’s interview clip on what the worth growth problem is (Link)

ICYMI

  • Never Make Another Financial Decision Alone (Link)*

  • Ayman Al-Abdullah on the 5 things CEOs actually do (Link)

  • Chris Orlob on why most deals die (Link)

  • KP on the 4 things founders need to win in a crowded market (Link)

💡 Opportunity: HVAC Failure Maintenance Platform

If you’re in the US, you know that we love our air conditioning. If you’re in Europe, I’m sorry but you’re missing out.

If you’ve ever had your HVAC unit break though, you know real pain.

If it’s a commercial system, neither the tenant nor the landlord often thinks they should have to pay for it.

If it’s residential, sometimes that still happens but the bigger problem is that the tenant has to actually live without it for some amount of time without another place to go.

But most failures are pretty predictable if only you were able to collect data on the system as it runs.

This data would save on having to do unnecessary checkups and also alert you to failures before they happen.

You’d need to produce a small hardware device to plug into HVAC units, but the costs would be more than covered by the pain saved down the road. You could sell subscription access to a monitoring dashboard + alerts as well.

I’d recommend focusing on the commercial market, likely in the southeastern US where usage is high and so is buying power.

🧠 Framework: The 4-Question Close Framework

This one’s for the closers.

One of the easiest ways to get better at closing (deals, sales calls, investors, prospective hires, etc…) is to stop pushing at the end of calls or meetings.

Don’t let yourself live and die by the outcome — focus on the process.

Here’s a simple four question framework to help:

  1. Based on everything we’ve discussed, what feels like the biggest obstacle right now? → reconfirms the pain point using their own words

  2. If nothing changes in the next 6 months, what does that actually cost you? → reminds them of real impact of not saying yes

  3. What would be different if the obstacle was fully resolved? → lets them paint their own better future

  4. Given what you’ve shared, what feels like the right next step for you? → at this point, they’re basically closing themselves and you’re not being pushy

This is simple but it works because it follows how humans actually make decisions: problem → cost → vision → choice.

🛠 Tool: Radiant

Radiant is a Mac app that turns meetings into completed work.

It captures meetings automatically, without bots, then drafts follow-up emails, summaries, documents, and next steps in seconds.

Chat with meetings to pull context, generate drafts, and move work forward. Edit and format everything before sharing.

Radiant completes all your next steps before your next meeting.

📈 Trend: Generative AI 3 Years In

In my lifetime there have been three major platform shifts:

  1. From local machine to internet

  2. From desktop to mobile

  3. And now from “dumb” to AI-powered

I’ve seen a lot of direct comparisons in how fast these were adopted, like the chart below. (You can argue crypto should also be on it, with over half a billion users now.)

It’s undeniable that AI is being adopted and implemented at a pace we’ve never seen before but, personally, I don’t think these comparisons are fair.

AI is being adopted much faster largely because the internet already exists and has been widely adopted.

The internet didn’t have the internet to help it spread faster.

This doesn’t change the story — AI’s adoption, and the new discoveries that come about as a result, will continue at a torrid pace at least until there’s a bubble that bursts.

I was talking to a billionaire VC, who had been actively investing during the dotcom era, earlier this week and he estimated it would be another 3-4 years before we had to worry about anything imminent there.

💬 Quote: People Pay To Stop Feeling Pain

Startups solve problems.

And problems are only, you know, problems if they cause pain.

Sometimes we forget this. We think about solving a problem, or even a painpoint, as some sort of abstract mathematical equation.

Concern + solution = revenue.

But doing that removes the actual humanity of why startups are valuable in the first place.

It’s not overly grandiose to say that startups make the world a less painful place.

This is obvious in some cases, where a startup is directly addressing a physical or mental pain — even software like Calm or BetterHelp.

But think about social media.

Its societal function is obvious now, but a common joke 10+ years ago was to tease by asking what problem a platform like Facebook was really solving. And while not everyone would consider it a net positive for society, it’s clearly addressing a pain of loneliness and disconnection, among other things.

Even an upstart hardware device like friend.com (which I wrote about when they paid seven-figures for their domain name) is addressing pain. Their founder talks about it relentlessly.

An index of pain (volume * intensity) is a lens through which we should evaluate how effective a startup could be.

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