Opportunity → Expert AI Sales Agent

Framework → PESTLE Analysis

Tool → Kick

Trend → Outcome-Based Selling

Quote → Don’t Let Bad Reasons Stop You

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Aditya Singh shares the founder ownership % after each funding round (Link)

• Martin Tobias shares what founders don’t have that he makes bets on (Link)

Growth

• Marc Lou shares 32 principles of a viral product (Link)

• Jake Castillo on the type of trust that converts (Link)

• Maja shares what the moat is (Link)

ICYMI

• Level up your workflow for Q3 with 25% off Google Workspace (Link)*

• Matt Gray on 10 things he lives by as a founder (Link)

• Starter Story shares the 24 startups he tried to build & why they failed (Link)

• Jared Friedman on how to find a truly impactful idea (Link)

• Jay Yang shares Patrick Collison’s advice to young ambitious people (Link)

💡 Opportunity: Sales Reminder Agent

Sometimes you just need a little nudge.

That’s at least what Adam Wazzan, co-founder of orchid.ai (which went through YC last year) thinks:

A simple agent that bumps you in Slack or over iMessage, WhatsApp, or email to follow up with someone is probably more useful and timely than whatever system you’re using to set reminders right now.

An interesting observation here: even agents with seemingly small, discrete tasks still need a ton of context and access to be able to do their jobs well.

To me, that implies that the future (where we all have tons of agents working for us, managing each other, etc) will require robust permissions and access controls, and the traditional software platforms that there are likely many more opportunities in the MCP space too.

🧠 Framework: PESTLE Analysis

Startups are fragile and not everything is within your control.

Macro factors can materially shift your chances of success, and you simply have to be adaptable to them.

PESTLE is a framework that describes the types of risks to look for:

• Political → Leadership changes, taxes, and trade rules. Look for policy risks before expanding or entering regulated markets.

• Economic → Inflation, spending, interest rates, and costs. Assess customer affordability, pricing power, and fundraising timing.

• Social → Attitudes, demographics, and culture. Align your messaging with real trends.

• Technological → Innovation, adoption, and access. Inform your product choices and pivot to new approaches when needed.

• Environmental → I’d consider this one a bit more optional for most industries, but you can look for sustainability-focused edges where it makes sense to.

Together, you’ll have a good handle on external factors if you review these monthly or quarterly.

🛠 Tool: Kick

If bookkeeping is the task you keep pushing to “future you,” it’s worth taking a look at Kick.

Kick is an AI-powered bookkeeping platform that automatically categorizes transactions, matches receipts, reconciles accounts, and generates real-time financial reports. It connects with banks, Stripe, PayPal, Gusto, Ramp, and thousands of other financial institutions.

If you’re a founder, freelancer, consultant, or small business owner who wants cleaner books without the usual bookkeeping headaches, try Kick.

Get 10% off 12 months here*

📈 Trend: Outcome-Based Selling

Still charging by seat? Or by tokens used?

Your customers probably wish you weren’t.

Increasingly, companies that charged based on the number of positive outcomes they achieve for their customers (i.e. booked meetings, impressions generated, etc) are being preferred by those customers.

The reason is simple: it fundamentally de-risks a customer’s purchase since, really, would you rather pay to consume (and hope the results work out and deliver real value) or pay per result?

Here are some reasons it generally makes more sense:

1. Risk is assumed by the vendor, not the customer

2. Cost aligns with actual business value generated

3. The vendor has a stronger incentive to perform

4. Customers get a more clear map of CAC to LTV

Honestly, it also is kind of a flex. If a vendor has outcome-based pricing, it makes customers feel confident that they know what they’re doing.

If you’ve tried outcome-based pricing for your startup, I’d be curious to know how customers have responded… shoot me a reply and let me know.

💬 Quote: Don’t Let Bad Reasons Stop You

Founders can’t afford to be defeatists.

Many successful startups have been built on top of the graves of others that tried something very similar. For example, Instacart is worth $10 billion while Webvan crashed and burned.

There are reasons why things fail, of course.

In Webvan’s case it was a combination of excessive burn, market conditions (aka the dotcom crash), and it being too early for the tech to really solve what it tried to.

My point is that even if someone’s failed before, or the market’s crowded, those are among the many bad reasons to assume you’ll fail.

Assess the opportunity objectively. Do you have a unique way to acquire users/customers, retain them, or some other defensible and actually disruptive reason why you will win?

If so, that’s all that matters.

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You meet and build a relationship with your dream partner to start a new company with.

They mentor you, you do academic research together.

Then you ask them to become co-founders and… they turn you down.

Disappointing to say the least, right?

Not for Alina Su.

She managed to turn a no into a “hell yes” six years later and started Generation Lab with legendary longevity researcher Dr. Irina Conboy and Michael Suswal (co-founder of the unicorn Standard Cognition).

So far, they’ve raised $15M including having Accel lead their seed round, with participation by Giannis Antetokounmpo, Steve Aoki, me, and other great folks.

She told me the story (and more, like why she keeps on a clock on her desk counting down to roughly when she expects to die):

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Most founders don’t realize how much time they’re losing to scattered tools.

A file in Dropbox. A meeting link in Zoom. A doc in Word. A calendar in Apple. None of it talks to each other, and you’re the one paying the price.

Google Workspace with Gemini changes that. One login. One ecosystem. Gmail, Drive, Docs, Sheets, Slides, Meet, Calendar, and more — all built to work together from day one. Also with built-in AI, Gemini is a co-pilot that helps you write, summarize, and respond faster.

It’s not just software. It’s the infrastructure serious businesses run on.

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Treat Every No as a Not Yet

In 2018, Alina joined Dr. Conboy’s research lab at UC Berkeley.

She was just an undergrad studying bioengineering after immigrating to the US a few years earlier.

Over the next 3+ years, she helped out in any way she could even if it meant getting coffees and donuts for their group.

Alina was obsessed because she knew Dr. Conboy’s research, which showed how many traditional markers of aging were actually reversible through plasma exchange, should be used in commercial products to change lives.

That might sound surprising, but you’ve likely seen billionaire founder Bryan Johnson talk about doing regular blood transfusions (originally with his son) as part of his longevity protocol.

One of Dr. Conboy’s insights is that the main benefit of plasma exchange has nothing to actually do with “younger” blood, but rather it’s just the dilution of the older plasma.

She’d first released work on plasma exchange way back in 2005, with this new insight coming in 2016.

But throughout that whole time, she (nor anyone else) had commercialized it with a product.

Alina was determined to both convince and help her to do that, though Dr. Conboy turned her down initially.

Many founders in this scenario would have either given up, or tried too hard to push for a yes.

Alina, instead, looked at what she would need to do in order for Dr. Conboy to say yes. She realized that she had no experience building companies, so what value was she truly bringing to the table for an established researcher like Dr. Conboy?

Before circling back to start Generation Lab in 2023, Alina built and successfully exited another company, NovaXS.

She went through Techstars with it and, there, met Michael Suswal. At the time, Michael was building Standard Cognition to a billion dollar valuation.

After NovaXS was acquired, she went back to Dr. Conboy and Michael and pitched them both. Michael, on the longevity space. And Dr. Conboy, on commercializing her research together.

When you want to build something world-changing, finding a truly world-class subject matter expert is hard. Convincing them to build something with you is harder still.

Alina’s journey makes it clear that playing the long game, and making yourself the type of person with the right experience that your desired co-founder would want to build with in the first place, is the right response.

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How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

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Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

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Opportunity → Internal AI Skill & Prompt GitHub

Framework → Value Proposition Canvas

Tool → Viktor

Trend → Founders Are The Happiest People In Tech

Quote → The Biggest Risk Is No Delusional Goals

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Most founders don’t realize how much time they’re losing to scattered tools.

A file in Dropbox. A meeting link in Zoom. A doc in Word. A calendar in Apple. None of it talks to each other, and you’re the one paying the price.

Google Workspace with Gemini changes that. One login. One ecosystem. Gmail, Drive, Docs, Sheets, Slides, Meet, Calendar, and more — all built to work together from day one. Also with built-in AI, Gemini is a co-pilot that helps you write, summarize, and respond faster.

It’s not just software. It’s the infrastructure serious businesses run on.

👉 Get 25% Off Your First 6 Months

Get 25% Off Your First 6 Months

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Brent Fulfer on the shared trait between the best founders he’s backed (Link)

• Karri Saarinen on how to approach fundraising (Link)

• Jason Yeh on what founders don’t realize (Link)

Growth

• Steven Cravotta shares everything your paywall needs to make $10k/mo (Link)

• Gabriel Jarrosson on what hiring decision kills startups slowly (Link)

• Adrian Partain on the #1 lesson learned that transformed how he builds (Link)

ICYMI

• Generate leads, convert website traffic, or hire sales AI SDRs (Link)*

• Gloria Lin’s founder dating playbook (Link)

• Ayman Al-Abdullah on the 3 things you can’t delegate (Link)

• Paul Graham on how to make startups AI-proof (Link)

💡 Opportunity: Internal AI Skill & Prompt GitHub

Basically every startup uses GitHub.

It’s a no-brainer. If you’re reading this and have any background in engineering, I don’t need to extoll the virtues of version control, not to mention GitHub’s collaborative platform.

It’s just what you use to host your codebase.

And every startup has a codebase.

Well, soon (if not already), every startup will have a need to host their agents’ proprietary skills, and their company’s prompt library.

GitHub was acquired by Microsoft for $7.5 billion. If you believe making markdown files easy to use will be anywhere near as valuable for companies as code, the opportunity here is massive.

When you consider that the actual userbase for this tool would include a significantly larger percentage of the company than GitHub can reasonably touch, it gets pretty exciting.

🧠 Framework: Value Proposition Canvas

This week’s framework offers a simple tool (thanks to Mooncamp for the share!) to design products and services that customers actually want by mapping their reality against your offer.

On one side, you have a value map. This includes what you offer, how you reduce customer pain, and how you amplify their success.

On the other, you have a definition of your ICP (what job they’re trying to get done, and what pain and successful outcomes look like for them in the first place).

The goal, when mapping this out, is to identify where the “fit” is between what you’re able to offer and their priorities.

Here’s a simple way to use it:

1. Pick one customer segment

2. Map their customer profile (stack rank their pains and “gains”)

3. Identify gaps or misalignments in your current offerings to ideally address these

4. Decide which gaps to address

🛠 Tool: Viktor

Most AI tools answer questions. Most AI tools answer questions. Viktor actually gets work done.

It operates inside Slack and Teams, connects to tools like Google Drive, Notion, Shopify, and Airtable, and can handle everything from reports to workflow automation. Teams are using it to eliminate repetitive work and move faster without adding headcount. Viktor recently crossed 2,000+ organizations using the platform and raised a $75M Series A.

New users get $50 off through our link.

Try It Here

📈 Trend: Founders Are The Happiest People In Tech

My pal Lenny Rachitsky surveyed 8,200 tech workers about their happiness (and other things, it’s a good read).

While you might think the cushy button-color-changing product managers at Google are the happiest among us, you’d be wrong.

It’s actually us, the founders. In fact, founders are the only group in the survey who were growing more optimistic about the future as well as outranking everyone else in overall workplace well-being.

We also reported the lowest burnout.

These things go hand-in-hand. A high sense of purpose, fulfillment, clarity, belonging, and excitement directly leads to happiness.

A $400k+ big tech salary can’t compete when you feel like what you do doesn’t matter as much.

Also, let’s be honest, even though we have the most responsibility on our shoulders and surely deal with the most stress, we’re built for it. We’ve self-selected into this life.

💬 Quote: The Biggest Risk Is No Delusional Goals

A friend (who was mentored by Elon Musk) told me he believes the difference in effort required to build a unicorn and an SMB business is actually not that different for the founder.

They’re different, sure, but the argument was that it’s not like they are multiple orders of magnitude different.

Honestly, building any business takes a ton of effort and time. We all know this.

And the most successful people I know set really big, “delusional” goals.

Take a second and think about the biggest thing you’ve ever seen someone accomplish.

Then remember they are just a person, like you.

They simply set out to achieve something extraordinary.

It’s easy to forget that. It’s easy to forget that we each have the ability to bend the world to our will.

So if that’s true, you might as well go after something huge and audacious, right?

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Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

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Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in this newsletter to get in front of 65,000+ founders.

That sounds a bit surprising, right?

Well, Ratmir Timashev sold his last company for $5 billion, and he recommends founders look for what he calls “waves” instead of markets.

I sat down with him to discuss the difference, what “founder magic” really is, and why he’s now betting $130 million on Columbus, Ohio becoming the go-to-market headquarters for North America through his new company, OH.io:

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Fundraising and building a startup require serious organization. Notion gives founders one powerful workspace to manage it all — from investor outreach to internal docs, product roadmaps, and team workflows.

Through the Founding Journey AI Fundraising Kit, founders get access to Notion fundraising agent workflows, including a 10,000-investor database, 50+ real pitch decks, and ready-to-use fundraising templates.

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Waves Over Markets

There’s a lot of FOMO out there in the startup world.

Everything moves so fast, and everyone’s worried about missing the right time for their big idea.

For example, many founders I know who had raised money for non-AI companies in the last few years have told me they felt like they were missing out on building something AI-native.

But whenever a founder tells me they’re worried they’ve missed the boat on a market, I give them the same advice.

Being a founder is like being out in the water on your surfboard.

You’re watching the waves as they come towards you, looking for one you can ride into shore.

And if you miss a great one, it’s actually ok, but there’s another one coming soon behind it.

Innovation and the startup ecosystem works the same way.

Today’s big ideas create new space for tomorrow’s.

Ratmir Timashev’s philosophy, that’s led him to two massive exits so far, takes my analogy one step further.

He says that founders shouldn’t be looking for “markets” in the first place because, by the time a market exists, someone else is already building for it.

Instead, founders should look for “waves” that are just now starting to form. And you either catch it or let it fully pass you by.

The distinction matters. And Ratmir’s done it twice.

First, in the 90’s, Ratmir co-founded Aelita Software which was sold for $115 million after riding the wave of internet adoption.

Ratmir noticed that servers would crash without an easy way for IT administrators to quickly recover their data, so he and his co-founder built one.

Next, he started Veeam Software which saw a similar type of wave forming with virtual servers.

VMware was turning physical servers into virtual ones. Every company was adopting it. And the backup tools that worked for physical infrastructure were useless in a virtual environment

Both were built with the same insight: every new technology layer creates a management problem. And whoever solves that management problem first cleanly, for the actual people running the system day-to-day, wins.

Right now, the entire stack is being reimagined due to LLMs. And the layer Ratmir’s looking at is distribution and GTM strategy.

I believe the technology barrier is even smaller now. It’s all gonna be about go-to-market.

The companies that are gonna win in this AI race are the ones that figure out the best go-to-market motion and figure out the distribution.

Ratmir Timashev

And he believes in Columbus, Ohio’s potential to be a hub for GTM knowledge and talent, in the same way SF is a hub for engineering talent.

When Ratmir first came to the US after the collapse of the Soviet Union, he landed at a PhD program at Ohio State University, so it’s an area he both knows well and has an affinity for.

But this isn’t charity. Through OH.io, he’s investing in the region building something unique to capitalize on and ride this new wave of AI adoption.

How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 70,000+ founders.

Opportunity → Permit Zoning AI Agent

Framework → AARRR Framework

Tool → Google Workspace

Trend → Super ICs

Quote → Build Products You Would Pay For

PS — Become a member to get access to my founder membership including an engaged community, fundraising support, fireside chats and more.

Subscribe now

Fundraising and building a startup require serious organization. Notion gives founders one powerful workspace to manage it all — from investor outreach to internal docs, product roadmaps, and team workflows.

Through the Founding Journey AI Fundraising Kit, founders get access to Notion fundraising agent workflows, including a 10,000-investor database, 50+ real pitch decks, and ready-to-use fundraising templates.

You’ll also unlock $15,000+ in founder credits and up to 3 months FREE of Notion’s top business plan to run your startup more efficiently while raising capital.

Get started here

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Carina Cunha shares 3 rules founders can’t break during a raise (Link)

• Abdelkader Yousfi on how funding stages exist for a reason (Link)

Growth

• Jon Xu on what your startup’s growth rate really is (Link)

• Ayman Al-Abdullah on what problems at different revenue stages (Link)

ICYMI

• If users understand your product in 60 seconds, your sales cycle gets a lot shorter (Link)*

• Gokul Rajaram on startup hiring (Link)

• Can Vardar on what most founders really need (Link)

• Kaari Saarinen on the fallacy of working 7 days a week (Link)

• Jake Castillo on the most underrated thing in business (Link)

• mal on what the best founders he knows don’t do (Link)

💡 Opportunity: Permit Zoning AI Agent

One of my favorite early AI companies in this era was DoNotPay.

It started off back in 2015(!) using machine learning to fight parking tickets for you.

Why it’s appealing seems obvious. Everyone knows how tedious and convoluted most government-run processes are (how was your last DMV trip?) but they’re notoriously hard to innovate for.

DoNotPay gave people a way to get both their time and money back in one of these situations.

All of this to say, I like this idea that Eren Bali shared for the same reason:

Whether you want to do anything, from building an addition onto your house to setting up a retail store, you need an in depth understanding of the often confusing zoning and permitting laws in your area. In some parts of the country (cough cough SF) these are particularly complex

This, maybe surprisingly, is a high-leverage point to claim ownership of as a result and exactly the kind of idea that looks small at first but can get much larger as it gets embedded into how users solve these types of problems.

…or you could just build it as the agentic equivalent of a micro SaaS and help people out regardless.

🧠 Framework: AARRR Framework

Hold your pirate jokes, we’ve got the AARRR framework this week.

Pirates don’t really have anything to do with funnel design and customer acquisition (though I guess they “acquire” treasure…? Kind of a stretch tbh) but here we are nonetheless.

The takeaway here is that if any of these five stages is leaky or not working right, you’re going to be wasting money on acquiring new customers in the first place.

So, before you go spend your treasure, make sure each stage (below) is running smoothly.

🛠 Tool: Google Workspace

If your team is still bouncing between a dozen different apps, there’s a better way.

Google Workspace with Gemini gives you Gmail, Drive, Docs, Sheets, Meet, Calendar, and more — all connected, all in one place.No more “which version is final?” or hunting down files across platforms.

And with built-in AI, Geminican draft emails, summarize documents, and cut through busywork faster than ever. Designed for teams that want to move — not manage tools.

👉 Get 25% Off Your First 6 Months*

📈 Trend: Super-ICs

The concept of the 10x engineer is dead, actually.

Olivia Moore from a16z shared a chart from Cursor showing that the gap between the number of lines of code that are committed per week by the 90% percentile of engineers vs the median is rapidly growing.

The best engineers have always shipped more than the average, but now that delta is getting larger and larger.

Wait… doesn’t that mean 10x engineers are more valuable, not dead?

Stay with me here.

We’re moving into an era of “super ICs” more broadly.

What we’re observing here is that the value of ICs who master LLM-powered tools and workflows is growing much faster than the value of those who don’t.

So the 10x engineer is getting more valuable.

But engineering is just the easiest discipline to measure this in.

Olivia and I agree that the this is likely happening across every type of role.

So it’s not worth singling out engineers as the only discipline where “10x” is possible, and these super ICs are more than 10x more valuable than an average performer at this point anyway.

💬 Quote: Build Products You Would Pay For

Last weekend’s deep dive was about why you should build what you know, and the advantages that gives you.

Let’s take that one step further.

It’s one thing to know a space or a problem.

It’s another thing for it to be impacting you to the degree where you would legitimately pay for the solution you’re building.

Not only can you move faster by speaking the language, so to speak, but you are also inherently motivated to solve the problem because it will make your actual life better.

So when you’re building something new, and trying to decide if it’s worth going to market with, hold it up to that exact standard: would you buy it yourself?

That sounds easy but it requires a lot of integrity on your part. It’s easy to delude yourself here. You want it to be true. You want to have uncovered something worth building.

It’s a super common founder impulse to fall in love with your own idea.

Fight that. Stay true to how you evaluate products and services in your actual life. And then it becomes a useful filter.

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How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Audience Building

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in this newsletter to get in front of 70,000+ founders.

For some founders, building a startup is opportunistic. They look for the biggest problem and try to go solve it.

For others, they look for a problem they already understand because they’ve lived it.

Chris, Lindsay, and Michael Lenard of Horse Spot fit the second category for a T.

They’re taking a larger-than-you’d-think niche (and insular) market that’s running on 20+ year old software, and modernizing it.

But why they’re succeeding is because, even in a market that’s skeptical of change, they fit right in and can build trust quickly. They understand the problem at a level outsiders would not.

This is a story about why, sometimes, it’s a good idea to build in areas you’re passionate about:

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Every founder reaches a point where the patchwork of free tools starts slowing them down.

Separate apps, broken workflows, files living everywhere — it adds up fast.

Google Workspace fixes that. It’s the all-in-one productivity suite trusted by businesses worldwide — Gmail, Drive, Docs, Sheets, Slides, Meet, and AI features supported by Gemini to help you draft, summarize, and get more done in less time.

Everything syncs, everything shares, and your whole operation lives in one place. Cleaner workflows. Fewer headaches. More time for the work that matters.

👉 Get 25% Off Your First 6 Months

Build What You Know

There are perks to being an insider.

All of them allow you to move faster, and generally be preferred by your customers over competitors.

Here are four advantages Horse Spot has had that can easily apply to other verticals as well:

Skip The Guesswork

Perhaps the most obvious benefit is that you can often build with confidence.

You should always do user research and talk to customers, but when you’ve lived the problem in the past you can afford to make some assumptions (because your assumptions are based on real knowledge and will legitimately be better and higher accuracy than they otherwise would).

In Horse Spot’s case, industry knowledge let them entirely bypass most of the early requirements gathering before they started building the product.

They’d already spent years doing that without realizing it.

Speak the Language

Communities are based around shared culture, norms, etc.

It’s those little nuances that let you build faster. You implicitly know things that outsiders will literally take months, or in some cases years, to realize.

Horse Spot understood from day 1 how other insiders would react to certain features, pricing structures, and the right long term vision.

This is the type of advantage that even a more well-funded competitor wouldn’t be able to compete with quickly.

Of Course, Relationships

It’s way easier to sell to people you already know and who already trust you, or who you’ve been introduced to by a mutually trusted intermediary.

There’s no substitute for direct relationships and the warm intros they bring as well.

But it’s not just sales. Relationships mean faster feedback loops, and an ear to the ground on how the market’s preferences shift over time.

It can let you plan for what’s coming rather than just being reactive.

Genuine Credibility & Love

Particularly in tight-knit, insular, community-based industries like the horse show world, the best way to build trust quickly is to be able to show clearly that you genuinely understand and love the industry you’re building for.

And there’s no real way to fake this.

Horse Spot spent years working at and riding in horse shows, and even went back to work in show offices again when they first decided to build the company.

Those are more than compelling talking points when they go to sell, now. It’s a longterm demonstration of their interest in the space that makes others, who have that similar lifelong interest, feel like they can trust the product.

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How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

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If your answer wasn’t “immediately go start another company with a bigger goal” then you’re not quite like Emil Barr.

Emil is essentially following the Elon approach. After Elon sold Zip2 in 1999 and made $22M from the sale, he used over half of that to start PayPal.

When you win big early, you’re time-rich too and can afford to double down on what’s next.

I sat down with Emil when we were both out in SF a few months ago during his fundraise for Flashpass (which hit $4M ARR in its first year and is on track to quadruple in its second). They ended up with an oversubscribed $4.25M seed round that I participated in.

He was candid about how the level of commitment required basically left with him with a very non-traditional college experience, and what made his Wall Street Journal op-ed go viral:

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A founder went viral last week. I saw the post, knew nothing about them, and had a call scheduled for the next morning.

Hyperagent made this happen.

It pulled their best interviews, surfaced the arguments they keep coming back to, flagged what nobody had asked them yet, and drafted a question arc to outline their story. Full prep brief, ready to go.

I walked in knowing exactly where to take the conversation.

You could do the same — investor outreach, customer discovery, hiring pipelines, launch PR lists. A fleet of agents, running autonomously, doing the work.

The Founding 500: $200 for $20,000 in Hyperagent credits. 500 spots. Deadline May 31.

Apply → hyperagent.com

How to Front-Load Success

What Do I Mean?

When I say front-loading success, what do I mean?

The traditional path in life is not going to lead to happiness. Work a 9-5 at slightly higher salaries over the years, get your 401(k) match, and then retire one day to do… what you really want to do.

Fewer people are buying into that today than ever before, but it’s still a dominant narrative.

Emil takes the opposite approach to the extreme. His perspective was that it wasn’t enough to be successful, he wanted to ensure he’d achieve success as young as possible.

Success is leverage. Capital is freedom (of time, movement, you name it).

Many founders wait years before starting their first company. They want the big company logo for credibility. They want the skills they’ll acquire there too.

But instead of planning to spend years until being ready to build a big business, Emil asked himself what it would require to achieve that right out of the gate.

The Playbook

Emil’s success is an outlier but it wasn’t an accident.

Here’s the currency he spent to achieve it:

• 3.5 hours of sleep per night so he could spend over 12 hours a day on his business

• DoorDashing every meal, skipping the gym and living on Red Bull (he gained 80lbs at the time)

• Sacrificing friendships and “the college experience”

That’s not standard, and he admits it was a brutal cost, but it led to things that he says were worth it:

• Financial freedom at 20

• Personal mentors who are billionaires

• Deferred admission to Stanford’s Graduate School of Business

While intense, Emil doesn’t think his approach is outlandish. He cites Elon, Kobe Bryant, and J.K. Rowling as examples of how outlier success comes from outlier levels of commitment.

Last fall, he published this op-ed in The Wall Street Journal about why work-life balance will keep you mediocre.

The piece hit a nerve and became one of their most talked about pieces of the year with over 2,100 comments on their site alone (I didn’t even know that many people still went to legacy media websites, but I digress…).

Even months later when it gets reshared on X it draws thousands of engagements.

What’s Next?

Young, successful founders are not abnormal in Silicon Valley, but they’re considerably more rare in Ohio (where Emil is from and still lives, though he told me he’s buying a plane to make traveling back and forth easier).

It puts Emil in an interesting position.

On one side of his life, he sees the excitement around AI in the tech world (though also some anxiety about white-collar layoffs). And on the other side, he sees the skepticism around how it will impact various industries and the availability of jobs that’s common in much of the rest of the country.

It’s clear to him that tackling AI-driven employment concerns is going to be a major issue over the next 5+ years.

I’m worried for all my friends in Gen Z. The job market they’re entering is changing rapidly.

Emil Barr

Flashpass builds software to power trade schools, which are going through a massive influx of interest right now. If AI takes the white-collar jobs, trade schools will likely supply a good chunk of the next wave of employment.

And if Flashpass is successful as a venture bet, Emil will have the leverage to do whatever he wants next. It’ll almost certainly be something even bigger.

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We can also help your startup in a few other ways:

Content Creation

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Growth

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Fundraising

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Advising

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Opportunity → AI Personal Trainer For Execs

Framework → The Chain Of Success

Tool → Notion’s Fundraising Kit

Trend → Founders Are Selling Less Per Round

Quote → It Comes Down To Pain Endurance

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I’m flying to SF in three weeks. Built an agent to find me the people worth meeting.

Its job: find rising builders, aligned partners, people doing interesting things.

Every morning, it scans LinkedIn, X, recent press, and events. Adds new people as they show up. Ranks the pipeline by fit. Sends personalized outreach and follows up.

I had a growing pipeline by lunch.

You could do the same — investor outreach, customer discovery, hiring pipelines, launch PR lists. A fleet of agents, running autonomously, doing the work.

Check out The Founding 500: $20,000 in Hyperagent credits per founder. 500 spots. Deadline May 31.

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Jesse Middleton on the biggest misconception in fundraising (Link)

• Colin Gardner on what not to tell people about your investors (Link)

• Chris Saum shares two fundraising red flags he’s seeing lately (Link)

Growth

• Paul Yacoubian on what not to put your sales team in charge of (Link)

ICYMI

• TheFutureParty helps you spot the cultural shifts shaping what your customers will want next (Link)*

• Ben Lang on how Jack Dorsey says any company can now be a mini-AGI (Link)

• Eurie Kim on the trait that all the best founders she’s backed share (Link)

• Harsh Makadia on what most people get wrong about AI in business (Link)

• Shweta’s hot take about first-time founders (Link)

• Taylor Shapiro on how the most important work is the invisible work (Link)

💡 Opportunity: AI Personal Trainer For Execs

Some of the best advice I got earlier on in my own journey as a founder was to sell things to people who have money to spend.

The quality bar will be higher but the ticket size, willingness to try (for the right offer), and revenue stability are all better.

Here’s another opportunity that fits that mold:

There’s probably a venture-scale shot you could take here, but also forward this to your friend who’s a personal trainer. You could change their life by telling them to spend a couple weeks learning the basics of OpenClaw and starting to scale their business even just a bit.

🧠 Framework: The Chain of Success

This week’s framework comes from Nascent Startups and is a pretty straightforward analogy:

Imagine your startup is a sequential machine (or chain) of things that need to go right in order for it to succeed.

Nascent identifies those as:

1. Paying customers

2. Team

3. Product

4. Marketing

5. Sales

6. Legal

I would encourage you to think strategically about the right things, and right order, for your particular startup.

Regardless of your chain, Nascent’s three takeaways are worth considering:

1. Fragility → The chain can break at any time, and it’s easy for this to happen. Too easy. Protect your chain.

2. Signal → Don’t build a link in the chain until you have some early insight that doing so will hold for the longterm.

3. Focus → You’ll need, as the founder, to shift your attention between the various links based on where you see weakness (to reinforce) or strength (to double down on).

🛠 Tool: Notion’s Fundraising Kit

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📈 Trend: Founders Are Selling Less Per Round

When we negotiated the terms of our Series A with a16z, we held on to our equity tightly and pushed hard on valuation.

Honestly, we were too stingy (especially since we had only raised one previous round rather than the normal two) and should have prioritized more capital and/or letting more folks in the round.

(And fwiw, I also wouldn’t recommend this because it puts you in a tougher position for the next round. You have more work to do to grow into your valuation.)

But, since then, it’s become something of a trend.

Realistically, the obviously acknowledged transformational power of LLMs and the inability of legacy competitors to compete is giving founders more leverage than ever in valuation negotiations… and they’re using it.

Here’s data from Carta showing that, at basically every stage, founders are selling less equity per round:

You can argue this either means they’re taking less capital (unlikely given the massive investment interest in AI-native companies by GPs) or, more likely, that valuations are up.

Inflation, a willingness to “overpay” just to get into deals, and more trends are likely converging into this.

I’d love to see someone overlay this with whether similar dynamics played out during the dotcom era, or the post-App Store rise of mobile apps…

💬 Quote: It Comes Down To Pain Endurance

Hey, founder… you’re signing up for something that is going to suck sometimes.

It’s going to be painful.

You’ll make tradeoffs that surprise you, sacrifice things you thought would be near-non-negotiables, and of course deal with rejection.

The reason most startups fail is simply because there’s some pain threshold that’s too much for the founders to navigate and manage successfully.

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How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Audience Building

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Fundraising

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Advising

I’ll help solve a specific challenge you’re facing with your startup.

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Opportunity → AI For Normies

Framework → The 6 Company AI-Pilled Levels

Tool → Google Workspace

Trend → Customer Service’s Bumpy Road

Quote → No One Cares About Your Idea

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Fundraising and building a startup require serious organization. Notion gives founders one powerful workspace to manage it all — from investor outreach to internal docs, product roadmaps, and team workflows.

Through the Founding Journey AI Fundraising Kit, founders get access to Notion fundraising agent workflows, including a 10,000-investor database, 50+ real pitch decks, and ready-to-use fundraising templates.

You’ll also unlock $15,000+ in founder credits and up to 3 months FREE of Notion’s top business plan to run your startup more efficiently while raising capital.

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Pavel Prata on what seems to be driving VC fundraising (Link)

• Kev shares an insight after reading 217 pitch decks (Link)

Growth

• Adam Robinson on what will always be present when PMF is real (Link)

• Chris Pisarski on the “email your boss” sales hack (Link)

ICYMI

• An AI agent that handles customer conversations across calls, texts, chat, and email (Link)*

• Internal Tech Emails showcases the texts between Sam Altman & Mira Murati - part of the evidence in the trial over Elon Musk’s lawsuit against Altman and OpenAI (Link)

• Bilal Farooqui shares two things that define a startup (Link)

• Ryan Deiss on the graveyard for founders (Link)

• Jordan Mitchell on how the founder “delusion” narrative is overplayed (Link)

• Elizabeth Yin on the paradox of hiring (Link)

💡 Opportunity: AI For Normies

It feels like everyone is using AI, right?

It feels like when you go home for the holidays this year, your grandpa will be telling you about his agentic team.

But the truth is we’re still so early.

Only 0.3% of the people in the world are actually paying anything to use LLMs.

Whether or not you agree with Andrew that IRL experiences are the best way to benefit from what AI has to offer, it’s clear there’s still so much whitespace for new ideas and new startups that leverage LLMs.

We’re not anywhere near the end of this run yet, even if OpenAI is starting to feel valuation pressure.

🧠 Framework: The 6 Company AI-Pilled Levels

Remember the mad rush around self-driving cars?

Waymo has largely solved it as a technical problem even if the service has been expanding outside of SF slowly.

You don’t hear much about the “levels of autonomy” for driving anymore.

But the concept of having different levels of AI-y-ness (yes that’s the technical term) are a good way to consider how companies have adopted LLMs across their entire business, too.

And Floodgate’s co-founder and GP Ann Miura-Ko did exactly that after hosting many companies claiming to be AI-native at Floodgate’s offices.

Her position is that most people are looking at whether they are “AI-pilled” as a binary idea when, in practice, companies differ both in how deeply AI is embedded as well as the technical capability of what AI is actually allowed to see, do, and change.

For example, a company where employees use ChatGPT to summarize meetings is not in the same category as one where agents can query systems of record, take bounded action, and improve the way future work gets done.

The questions Ann asked are:

1. What can AI see? How much context are you feeding it? Does the real way your company works only exist outside of queryable systems?

2. What can AI do? Summarization only or can it take action?

3. Who can extend the system? Engineers as the true power users only, or non-technical folks too?

4. How has the organization changed (relative to a few years ago)?

The whole piece is worth a read, but in short here are the six markers of what she considers to be a fully AI-native company:

🛠 Tool: Google Workspace

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📈 Trend: Customer Service’s Bumpy Road

The bumpy road for the customer service sector since the pandemic continues.

a16z shared this chart on X:

And if you break look at a longer time horizon you see this:

No one has seemingly known what to do with customer service hiring since COVID hit.

Most famously, Klarna did a total about-face on AI-driven customer service:

In late 2024, Klarna’s CEO Sebastian Siemiatkowski announced that AI could already perform the jobs humans do. The company paused hiring for more than a year, cut its workforce from 5,500 to 3,400, and promoted an AI chatbot it said was performing the work of 700 customer service agents.

Six months later, customer satisfaction had fallen sharply, and service quality was inconsistent. Klarna was now asking software engineers, designers, and marketing staff to help answer customer inquiries. The same CEO who once minimized the role of people was acknowledging that the company had prioritized cost over experience.

The wrinkle that, now, hiring in the space is outpacing overall hiring hints that current sentiment towards AI could be that customer service is one of the areas least likely to results in layoffs in the longterm.

That may sound counter-intuitive, given how many CS-related startups there are pushing AI tooling, but it makes sense. When you have a problem with a product or service, who do you want to talk to? Surely not an AI. You want empathy, service, and the human touch then more than ever.

As we covered in yesterday’s deep dive with Cape, relationships are currency in a world where the busywork can be automated with LLMs.

💬 Quote: No One Cares About Your Idea

This tweet only got 25 likes.

A few years ago it might’ve gotten 100+.

On X these days it’s popular to talk about the rise of the idea guy.

Execution is perceived as easy (or at least less important than it used to be).

Let me tell you something.

Having the right idea has always mattered. And so has how you execute it.

Just because you can build software faster doesn’t mean building a big company is easier.

In fact, it might be harder.

If it’s easier to build something of your own, more people will want to do just that… leaving them unavailable to help you build yours.

Execution was never just about pushing code to production.

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Your perfectly personalized cold email isn’t being read by your targets because they’re getting hundreds of them.

The best way to cut through the noise in this new world is through human relationships. Events, conferences, and warm intros.

I sat down with Ben Gusberg and Kai Zheng, two founders who saw this coming.

They built Cape, an AI tool that helps you turn relationships into revenue by showing you the best paths in your extended network to help you get in touch with your dream prospects.

Here’s why more founders are focusing on events, partnerships, and warm intros:

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Turning Your Relationships Into Revenue

What’s Happening

Traditional, digital growth channels are more oversaturated than ever.

When LLM-based sales tools first came out, everyone was excited.

Suddenly, they’d be able to stand out more in people’s inboxes because their messages would be hyper personalized.

The problem is that so many people understood that so quickly that, now, no one’s reading the emails and they’re getting more of them.

It’s gotten so bad for me that I should probably build an agent just to auto-respond “Unsubscribe” to these types of cold emails.

The evidence is everywhere that the real GTM evolution in the AI era won’t be just better personalization.

Why IRL + Warm Intros

The bet that Cape is making, and that I agree with, is that when standing out in inboxes becomes pointless you have to look elsewhere.

And so far, more and more founders are looking to event marketing, partnerships, and warm intros as those new paths forward.

Over three years ago I wrote about how IRL experiences and partnerships would be one of 8 types of moats in an AI-native world.

And that’s proven to be true. My good friend Andrew Yeung has multiple IRL events businesses that are growing rapidly.

There’s an energy at these events right now, where every conversation feels important and potentially business-changing. It’s a reprieve from the constant AI slop we read online. When you meet someone in person, it’s make or break but it’s also very humanizing and relaxing.

This is an inconvenient truth for those of us who are outside of traditional startup hubs like SF or NYC, but there are still ways to get involved.

How Cape Helps

Ben and Kai were ahead of this trend too, and they’ve built a tool that lets you make the most of it (even if you’re just in town or at a conference temporarily).

They look at events and conferences you’ll be attending and help you have meetings booked and identify people to meet before you’re even there.

But they also help when you’re not “in town” with a more robust founder-led GTM workflow that lets you unlock value (partnerships, investor convos, etc) that’s sitting in your network but you may not know is even there.

They comb through your LinkedIn and inbox to see who your second-degree connections are. The people you don’t know yet, put that people you know already do.

And they let you know who your strongest paths to those folks are and help draft your outreach to get them to make the intro for you.

How I Know This Works

IRL works.

Often better than you’d expect (since it’s hard to measure the same way something like ad spend or cold email is).

Before I started writing Founding Journey, my own IRL company for founder masterminds and retreats did over $3M in revenue in our first two years in business.

But that isn’t really how I know it works.

When I pop into a new city for a bit, or when I think about who I want their take on a business problem I can’t solve easily, or even when I need a warm intro myself, the relationships I built IRL are the ones that I go to first.

They’re lifelong relationships.

When things matter it’s not about who’s making the best pitch in your inbox from a cold message, it’s about who you feel you can trust already.

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We can also help your startup in a few other ways:

Content Creation

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Growth

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Fundraising

Share your round with hundreds of investors in my personal network.

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I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 70,000+ founders.

That’s the story of AppSignal, the well-known application performance monitoring startup that grew to over 2,000 customers processing over 100 billion requests per month and built a deep reputation within the Ruby on Rails community for 13+ years.

I had used AppSignal when I was building projects with Rails in college because other options were too bloated so, when I saw that they had raised $22M from Elsewhere Partners years later in 2025, I was interested in the story behind the decision.

Why would the founders of a company that had done millions in revenue while bootstrapping suddenly raise a ton of capital after years of turning down offers?

I sat down with two of AppSignal’s co-founders Thijs Cadier and Roy Tomeij, as well as the company’s new post-investment CEO Brandon Swalve to find out:

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13 Years Bootstrapped, Then $22M

Know What Kind of Founder You Are

For years, Roy was the face of the brand to customers and partners. When the investment happened last year, even though he remained with the company as a board member and brand ambassador, he stepped back from his role as Chief Customer Officer.

What’s interesting about it is that this was initially his idea. When we spoke, he was very candid, saying that “I think my qualities are in taking something from 0 to 10 and not so much from 10 to 1,000.”

He, Thijs, and their co-founder Wes, took the company to millions in ARR despite, as Roy says, “knowing only my high school economics class.”

That type of self-awareness as a founder, even after 13 years, is hard to reach. But admirable. Roy didn’t wait for the company to struggle, he put all ego aside and focused on what was right for AppSignal.

Be Pragmatic About Outside Capital

AppSignal stayed bootstrapped for years in part because every funding conversation went down a rabbit hole of trying to turn the business or product into something it wasn’t.

Roy and Thijs knew outside capital comes with expectations that tend to lead to feature bloat, which was the exact thing they built AppSignal to push back against from incumbents in the first place.

So, despite offers, they held onto their bootstrapped identity.

It wasn’t that they were anti-VC. Bootstrapping just allowed them to keep the product easy to use, and raise on their terms.

Keep Your Product Simple

AppSignal is loved by users and has done millions in revenue in part because the product’s original philosophy of deliberate simplicity in a market where competitors get bloated has stayed true since day one.

Thijs highlighted that their mindset is “always build from simple primitives instead of all these separate flows and bells and whistles everywhere.”

It’s easy to say that when you found the company. It’s much harder for it to still be actually true after nearly 15 years (despite continuous development on the product, improvements, etc).

Bloat is a choice, and one that works against you in many ways.

If you want to make something people not only want, but love, it has to feel like it’s built for them specifically rather than them feeling like they have to navigate menus and tabs to find what they’re looking for.

Culture Is A Competitive Advantage

Roy, Thijs, and Brandon all mentioned AppSignal’s culture as the most important thing that’s let them have success and that they want to preserve in the future.

Put concisely, they always want to make sure AppSignal customers and the broader developer community are treated the way they themselves would want to be treated.

In fact, the “no-asshole company” approach was Roy’s #1 consideration for whoever stepped in to take the reins. And Brandon’s commitment to it made it clear that he was the guy for the job.

This is yet another factor that has led AppSignal to be loved by their users over the years. It made their community outreach (events, conference sponsorships, their involvement with the Rails Foundation, and more) all ring authentic rather than extractive.

And, in the age of LLMs where product is easier to build than ever, customer love is a moat.

Choose The Right Partners

When I spoke with Roy he told me bootstrapping wasn’t just a financial strategy, it became part of their identities.

So stepping past that and into a new future meant finding partners who don’t want to do what so many others had wanted to over the years (aka changing AppSignal into something it isn’t).

The team spent a year talking with potential investors, and operators to step in as the new CEO. They went with Elsewhere Partners and Brandon, respectively, because they already understood AppSignal’s market inside and out, their motivation was to amplify what already existed rather than transform it, and they had the GTM experience that the team wanted.

Now their goal a massive US-focused expansion in 2026 and beyond as new opportunities like AI and OpenTelemetry are expanding the market organically, not a radically different product.

AppSignal’s journey proves you can build bootstrapped, stay human, and still reach meaningful scale. If you do that, the opportunity for capital will be there when it’s right for you.

If you’re trying to figure out if you’re still in the 0-to-10 stage or staring at your own “what’s next?” moment, AppSignal’s playbook is one of the most clear-minded recent examples of doing it right.

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How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 70,000+ founders.

Opportunity → AI-Blocked Backup Storage

Framework → AI Company Design Loop

Tool → Angels Partners

Trend → Stripe Atlas Startup Incorporations Are Up

Quote → 4 Roles Of A Founder

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I’m hosting a 2-day Delegation Mastermind with my friends at Oceans.

We’ll be going deep on the right ways to use OpenClaw, Claude, and how to hire the right AI-fluent operators to give you time back and more leverage to let you grow faster.

The goal of the mastermind is giving you more execution capacity.

Here’s the deets:

• May 30th - 31st

• San Diego, CA

• Cost = $1,500 (transportation and accommodation not included/provided)

Spots are super limited, as we want to keep this to be a highly curated group, so signup here (no obligation).

Signup to Join Here
PS — Become a member to get access to my founder membership including an engaged community, fundraising support, fireside chats and more.

Every founder knows the pain of skyrocketing cloud infrastructure costs. But how to reduce AWS expenses without compromising your product’s potential?

Spendbase, in partnership with AWS, offers up to $100k in free AWS credits for the Founding Journey community. All you need is a startup under 10 years old with a corporate website. Works for both new & existing customers (even if you got credits before).

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Geoff Woo on what not to put on your moat slide (Link)

Growth

• Jen Abel on the three things that matter in enterprise sales (Link)

• Aaron Will on how his sales team is purely ran by AI (Link)

• Brian Moran on the same 5 hires he makes scaling companies make first (Link)

ICYMI

• Happy Small Business Week! 🎉 Save 25% on eligible Google Workspace plans with Founding Journey (Link)*

• Manuel Medina‘s biggest founder regret (Link)

• Rohit on the things that kill startup ideas before they launch (Link)

• Sarah Lacy on what she’s noticed from her founder interviews (Link)

• Karl Mehta on how LLMs are becoming intelligence rails (Link)

• Christine Carrillo on how founders sequence AI adoption backwards (Link)

💡 Opportunity: AI-Blocked Backup Storage

What would you do if your LLM deleted your codebase and all backups?

The better question is what could you do?

I saw this story last week about how this actually happened to a startup called PocketOS. The data was gone in 9 seconds via a single API call to Railway (whose slogan, ironically, is “Ship software peacefully”).

Claude’s response when the founder asked what happened?

“I violated every principle I was given.”

Obviously, this calls Railway into question as much as anything else.

Modern, LLM-based systems need appropriate guardrails when given access to sensitive data. If I were interested in building in this space, I’d get to work on an LLM-native competitor ASAP.

🧠 Framework: AI Company Design Loop

Last week I dove deep on the 7 attributes of an AI-native startup after watching this YC video:

This week let’s apply how to set that up, in a simple framework from Kenneth Lou.

He proposes 5 “layers” that startups should have:

1. Sensors + data → Ingesting information from the outside world. This can be as simple as support tickets and emails, or something more unique. The key is an engine that gets better because it’s being fed more data. If it’s not captured, it didn’t happen.

2. Policy + governance → The rules of what the system can do on its own vs what it needs human sign-off for, and what must be logged.

3. Tools → This isn’t SaaS tools you pay for. These are things that live in code, not English. Garry Tan says that figuring out what belongs in markdown vs code is 90% of the battle. These are your tools.

4. Quality Gates → You do need safety / accuracy checks and human review for high-stakes or irreversible decisions.

5. Learning Mechanism → It’s not enough to have the system do these things, it needs to police itself. It needs a layer to recursively make itself better as you sleep.

Even if you have some or part of these, you likely don’t have them all yet, and they likely aren’t the core focus on how you run your business (you probably don’t really focus on running everything through this yet).

But you should. We all know how much speed matters in startups, and AI-native startups will have a compounding advantage in speed that others will not be able to catch. That’s defensibility in the LLM world.

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📈 Trend: Stripe Atlas Startup Incorporations Are Up

What follows layoffs?

Startups.

As we’ve been predicting, the rise in AI-related layoffs is leading to a huge uptick in entrepreneurship.

Patrick Collison from Stripe flagged that new companies incorporating with Stripe Atlas are up 130% from Q1 last year:

You can argue that some of this is due to Stripe’s general growth and proliferation, but Stripe is not some young scrappy startup anymore. The company was founded in 2010 which, unbelievably, is 16 years ago.

It’s not like Atlas is a new product.

People are building.

Some of these companies will fail, others will become unicorns, others will be Silicon Valley Small Businesses.

But more companies is generally a good thing, as it ends up leading to more wealth creation and, yes, jobs.

💬 Quote: 4 Roles Of A Founder

“Founder” is not a job.

I don’t just mean that in the sense of it having more ownership or upside or risk.

Jobs have distinct responsibilities.

Founders need to find and motivate people who then have jobs. Founders need to be adaptable to the needs of the moment, whatever those are.

Maybe this week you’re a growth marketer, next week you’re a vibe coder, then you’re fundraising.

The four roles below likely resonate with you more than any “job” ever will.

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We have to look for opportunities to be contrarian… and right.

LLMs have created many new markets and also re-opened some that VCs previously thought were capped.

Dating is the perfect example.

Conventional wisdom would’ve told Keeper.ai’s (full disclosure: I invested in their pre-seed) founders to go after a market that sees larger outcome potential (most dating app acquisitions don’t disclose the price, for a reason, and even Bumble’s stock has dropped 90% since its IPO)… even though it’s one that’s so obviously broken.

Those disappointing (in venture terms) outcomes aren’t a sign that dating can’t be a venture-scale market, instead they’re precisely the reason the market requires a radically new way of thinking about it.

So, instead, Keeper’s built an incentive-aligned business (users only pay if they get into a long term relationship) that leverages LLMs to take the best parts of dating apps (scale) and matchmakers (precision) to build something that could not have ever existed before.

I sat down with Keeper.ai’s founders to talk about:

• Why dating has historically been considered a tough market

• How they found a business model that was literally impossible before LLMs

• How they’ve flipped dating from a zero-sum market into a positive sum one

• Why incumbents can’t and won’t be able to compete

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How To Be Contrarian And Right

The Alleged Ceiling

Match Group, the holding company originally behind legacy dating website match.com, acquires most dating apps before they reach true venture scale.

It’s actually crazy. Their assets do a combined $3.3B of the roughly $6B in revenue in the entire dating market each year. One company owns more than half the market. Literally.

Acquisitions aren’t just a good and defensible strategy for them, they also tend to be good for the founders who built an upstart / niche dating app once they realize they aren’t going to be able to reach venture scale in the first place.

So even though market is, in theory, giant since it includes every person on earth it’s never been loved by VCs and has only achieved $6B in total annual revenue after decades.

To me, a radically new approach seems like the only way forward.

A Better Model

Despite the broken market, meeting people through apps has quickly become the most common way to do so.

Within the “met online” category there are really two options:

• Dating apps

• Online matchmakers

Apps have solved the scale problem. Their pitch is that instead of just having access to whoever happens to be around the proximity of your life, you get access to thousands or millions of potential matches. However, they want to get you swiping and using the app so their filtering system is very imprecise. A few surface-level questions and you’re off to the races).

Also, most people are too selective on dating apps in the first place even with the minimal amount of questions they ask — Keeper built a fun tool to show you the actual amount of people who fit your dating preferences so you can see how large the pool you’re going after actually is.

Matchmakers have the opposite setup: they get to know you really well, but can realistically only work with a small handful of people at a time (even counting their “databases”).

Why I liked Keeper from the moment I first heard about it (aside from the fact that they fit my arbiter thesis perfectly) is because they’re using LLMs to get the best of both worlds, without the downsides.

They can have the scale of a dating app (and have already had over a million organic signups) but know you as well as (if not better than) a matchmaker, with an onboarding process that is intentionally high-friction.

It took me 45 minutes or so, but that didn’t stop me because I knew the offer they were making of scale + precision was the most compelling option that, for them, has led to 1 in 10 first dates leading to a marriage. That’s a lot better than Tinder’s 1 in 100,000.

Radical Idea = Defensibility

Right now we’re all in search of defensible models.

Keeper’s got it figured out. Existing dating apps simply cannot compete on the one metric that matters most, helping people find lasting relationships, because their business model is built on the opposite incentive.

Traditional apps run on subscriptions + in-app purchases. Its their goal to keep you subscribed, not churning. The matches need to be good, but not so good you go off the app.

If Tinder switched to Keeper’s outcome-based pricing model, their ARR would crater overnight. It’s so big of a bet for them to make that the risk is too high for a business of their size.

Keeper’s using incentive-alignment as an uncopyable moat. They weren’t concerned with building a better algorithm, they built a company whose success is tied to that of their users while incumbents are trapped by their own economics.

The Takeaway

I’ve been keen to share Keeper’s story because it’s a reminder to all founders that being contrarian and right is not only possible, it creates defensible models that can unlock larger TAMs than are accessible to everyone else.

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Opportunity → Trade School 2.0

Framework → The Proactive AI-First Team Member

Tool → Pophatch

Trend → Average Per-Unicorn Market Cap

Quote → It’s Hard When No One Listens

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Most people will sit on their ideas this weekend.

You’re probably here because you don’t.

The Remy Hackathon (May 1–3) is a virtual, async weekend to turn an idea into a working product — without writing code.

Join hundreds of builders (Meta, Google, Oracle + more). $5,000+ in prizes.

After this weekend, you could have something real.

Go win $2,000

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Eric Bruckner on the VCs you should find (Link)

• I hosted Usman Gul for a chat on how to fundraise faster with better data (Link)

Growth

• Vitalii Dodonov shares his biggest hack running a $30M ARR startup (Link)

• khushi.vy on the different places to launch your startup (Link)

ICYMI

• Get matched with a fee-only fiduciary advisor — start the free quiz (Link)*

• Blake Mycoskie on the lessons he wishes he’d learned after selling (Link)

• Arjun on the best age to found your own startup (Link)

• Ayman Al-Abdullah on the 3 kinds of moats left in business (Link)

• Paul Graham compares what worrying about model companies is like (Link)

• Joe Speiser on the best time to sell your company (Link)

• Todd Saunders on the future of vertical SaaS companies of the AI era (Link)

💡 Opportunity: Trade School 2.0

Private equity is pouring into trade schools across the country.

Rollups are acquiring some schools and taking stakes in others. They’re paying for the reputation, knowledge, credential, and acquisition capabilities of existing schools.

It’s a reaction to LLMs seemingly being capable, at an increasing rate, of automating “knowledge work.”

It’s a complex issue because the following things are all likely true:

1. White collar companies are very bloated and employ a lot of people doing jobs that LLMs can do both better and cheaper

2. Those same companies would be better served trying to reorient themselves to get more out of their employees than doing mass layoffs

3. Blue collar work will become more valuable since AI will have a harder time taking it on

Regardless, it’s clear that trade schools are going to see a renaissance over the next few years because of a combination of capital injection, value, and likely applications as well.

But while private equity is pouring into older trade schools, there’s an opportunity to start new ones. What would a trade school built with the help of AI look like? What about the software to support them?

🧠 Framework: The Proactive AI-First Team Member

Even if you want to be “AI-native” you actually need to be solving real problems.

You don’t want to be “playing startup” or doing work that feels like you’re making yourself and your company more productive, but in actuality doesn’t drive you closer to your actual goals.

You can keep spending Claude credits to build systems that make your business more efficient, but don’t help you better serve your customers.

And, equally importantly, you need to screen for this when you’re hiring.

Allie Miller shared this framework on LinkedIn for how to identify a proactive AI-first team member.

It’s very similar to the traits you’d look for in any A+ new team member, just applied specifically to people who are actively using LLMs in their role.

The added execution capacity that LLMs give us mean truly top hires can make a bigger impact (or be more of a drain) than ever before.

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📈 Trend: Average Per-Unicorn Market Cap

I’ve been diving into this report from Elad Gil about the state of unicorns and there’s some interesting trends happening.

Right now we’re seeing one of the largest YoY increases in the average market cap of unicorns in recent memory (maybe ever) after years of this being relatively flat.

Typically, average market cap growth for unicorns has been primarily due to new companies becoming unicorns, and decreases have been primarily due to existing unicorns reaching an IPO.

However, from what Elad found, around 80% of the increase last year was due to existing unicorns growing their valuation with additional funding.

It’s sort of a perfect moment for exactly this to happen.

On one hand, you have “last gen” unicorns like Stripe, SpaceX, and ByteDance which have all stayed private for much longer than startups traditionally have.

On the other, you have they incredibly quick rise of foundation model startups reaching higher and higher pre-IPO valuations due to a combination of the immense value they’re creating and, to a lesser degree, inflation.

So, while the number of new unicorns is up compared to the last two years, it’s below the two prior yet we’re still seeing the average unicorn market cap at unprecedented levels.

💬 Quote: It’s Hard When No One Listens

Startups are hard.

And it particularly hurts when you pour hours, days, weeks, months, or years into something that ends up being “wrong” in the sense that you failed to make something people actually want.

Maybe you asked leading questions in your user research calls so you never truly understood their pain points. Maybe what you were building wasn’t unique or defensible enough to survive how fast things are changing these days. Maybe a black swan falsified PR crisis destroys your company out of nowhere.

All those things are hard to deal.

But you know what’s harder?

When you’re struggling to get to even one of those outcomes because no one is listening and paying attention to what you’re doing.

When you think something is going to work but can’t motivate anyone to do those user interviews for you in the first place.

Conventional startup wisdom would tell you to move on, find a new idea.

And 99.9% of the time it would be correct.

But we convince ourselves we’re in that 0.1% of the time where we’re sitting on something big no one else has figured out. That we are contrarian… and right.

Only you can decide where you think you’re at, and what the potential opportunity cost is worth to you, but it’s hard when no one listens.

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Not in terms of what problem you’d pick to solve, or who you’d hire, but how would it actually operate?

I saw this video from YC the other day that makes the case for making LLMs act as the true operating system for your startup and it got me thinking:

We talk a lot about AI-native work, but what does a truly AI-native company look like?

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The next coffee giant has a billion-dollar playbook.

Dunkin’ was acquired for $11B. JDE Peet’s IPO’d at $17B. Starbucks is currently valued at a $110B market cap.

While these are massive success stories, they all achieved their status without one major advantage: Owning the whole supply chain.

Green Coffee Company is vertically integrating the entire process from “seed to sale.”

They’ve already seen revenue grow from $1M to $37M in three years.

Now, they’re reigniting the legendary Juan Valdez brand in the $100B U.S. coffee market.

Invest in Green Coffee Company ahead of their targeted 2027 U.S. IPO.

Take a look

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7 Attributes of AI-Native Startups

Your Moat is Your Data Flywheel

Everyone’s worried about defensibility these days.

They’re concerned that since LLMs make software easier to build, software moats don’t exist.

The new moat is your data, and how you use it to acquire more data as an increasingly fast rate. Your internal data becomes a private moat that compounds faster than any public model can match.

Founders who treat every meeting note, support message, and usage log as structured data can create a compounding advantage that widens MoM.

Self-Improving Product Engines

It’s not enough for your agents to be writing code. It’s not enough to have them do QA.

You need orchestration layer agents whose sole focus is identifying issues in the current execution layer processes and outputs, and then communicating those to the execution layer agents so that they improve on their own.

It’s not your job to monitor the agents, it’s another agent’s job.

If you’re writing specs and tests, and the system underneath improves by itself, you can become a 1,000x engineer building a software factory instead of just a 10x building software.

Make Your Company Queryable

If you haven’t diligently had an AI bot in all your calls for the last few years, you’re at a disadvantage compared to the people who do.

Making every process machine-readable (even in simple ways like chatting in public Slack channels vs DMs) is the single highest-leverage infrastructural decision you can make right now.

It unlocks every other closed loop and gives you (and your company’s AI-brain) real-time, loss-free visibility that no legacy company can copy. It’s how the fastest moving companies are making such quick decisions at a highly accurate rate.

Founder = Swarm Orchestrator

I talked above about how agents need to act as orchestrators for other agents.

That’s true.

But your role is designating roles and governance rules for the entire swarm (rather than just prompting).

Reduce your human “middleware” and the chances your agents go rogue by setting up and owning these macro level orchestration responsibilities.

A good tool to start with her is Paperclip.

AI = The OS

LLMs aren’t some tool you “integrate” into processes.

Treat them as the single hub you run all workflows through. Treat every action like context farming.

The whole system should be a closed loop, and each process running through it should be a smaller one too.

If you treat it this way, and make your company queryable, you’ll free up tons of time that legacy companies spend on coordination and decisions that, to you, will seem easy and straightforward. That’s a massive W.

Track Intelligence-per-Dollar

Tokenmax but not blindly.

It’s ok to have an uncomfortably high API bill from Anthropic. In fact, it’s probably good. But spending tons of tokens needs to have a purpose.

You want to tokenmax more than you want to headcountmax, but set a counterweight by tracking the effectiveness per token as well.

You’ll need to set the right metric for your own business here (usage, users, ARPU, etc). But the key is to no longer look at those metrics in a vacuum and instead look at how well you’re doing per token.

Quick example: big companies get measured by revenue per employee. Why not measure your own efficiency, effectiveness, and decision making by revenue per 1,000 tokens?

This is the new capital-efficiency superpower that is going to let small teams out-execute big incumbents without burning tons of cash.

Flatten the Org Chart

Minimize human “middleware” that routes info from one area of the business to another. These busywork tasks and roles are no longer jobs for people.

Use your queryable company OS as the intelligence layer that can handle coordination.

The result is that there are three roles for humans:

1. Builder-Operator → This is the new IC. The “doer” who directly builds and runs these systems. It’s not limited to engineers (my historically ops-centric Chief of Staff has become one of these over the last couple months). They use agents as their primary tool to make impact at a larger scale than would have been possible manually.

2. DRI → The directly responsible individual owns one clear outcome and nothing else. They are focused on strategy and customer results, not managing people or processes. They have total accountability and, essentially, nowhere to hide. This replaces the traditional “manager” role. Since your company will be queryable, these folks get freed up to spend time on high-judgement decisions (often one-way doors) rather than managing people and coordination-level problems.

3. Founder → This is you. You build, coach, and lead by example. You never delegate your AI strategy, keep it as one of the few things you hold onto indefinitely like fundraising. Your job is to set the company up for success and how they use AI is a core part of that. You also need an insane level of conviction in the value of AI to make this all worth it.

As much as you can, spend time 1:1 with both Builder-Operators and DRIs. Don’t have one manage the other by default. Your job is not to create little pods where a DRI manages a few Builder-Operators. You want to keep the DRIs free to learn and make strategic decisions as much as possible.

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We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

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I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 70,000+ founders.

Opportunity → Brains For Enterprises

Framework → 3 Steps To Align And Execute

Tool → Notion

Trend → Top Cities By Unicorn Market Cap

Quote → You Are The Pitch

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Building with AI is easier than ever. Building a real growth engine? That’s still hard.

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Stop stitching. Start compounding. Explore the AI Tech Stack

Explore The AI Tech Stack

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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Stephane Nasser on how much equity founders own at exit (Link)

• Nicole DeTommaso on what due diligence is really about (Link)

Growth

• Erik Torenberg on how content succeeds today (Link)

• Lily Yang on how there is no correct GTM strategy (Link)

• Christian on when you should never share a Calendly link (Link)

ICYMI

• Claim up to $100K AWS credits via Spendbase (Link)*

• Martin Tobias on what your wedge product does (Link)

• Abby Borden on the most dangerous thing about AI (Link)

• Jesse Tinsley on what 99% of founders miss (Link)

• Tom Blomfield on if a company should go full stack (Link)

💡 Opportunity: Brains For Enterprises

You don’t need product engineering, you need context engineering.

We called this prompt engineering at first, but eventually these LLM-based systems will need minimal prompting from you. Instead, they’ll need better and faster ways to locate and share context between each other.

This is already “solved” for engineering since the codebase all lives in one place. But for much of the rest of what companies do, aka “knowledge work,” it’s spread between your meeting recorder, your Slack messages, etc.

There’s an opportunity for a filesystem for knowledge work that is specifically built for agents but also easy to navigate for humans.

Currently a lot of folks building with Claude Code or OpenClaw are using Obsidian for this, but it wasn’t really purpose-built for it. If you were around 5-6 years ago, Obsidian was first released among the wave of Zettelkasten “second-brain” tools like Roam Research.

These never really took off despite the value they provide in having linked records, simply because of the amount of time it takes to maintain them. For most people, the value was outweighed by the commitment.

Agents don’t have this issue, so Obsidian in particular is seeing a bit of a rebirth.

But just because they lucked into a new market doesn’t mean they will be the best tool to serve it in the longrun.

🧠 Framework: 3 Steps To Align And Execute

This week’s framework comes from a reader!

Ryan Batchelor, a navy officer, emailed me after one of our recent issues to share this alignment and execution framework he created as part of his work with Crux Leaders.

It’s a three step framework that turns a vague vision into focused, team-wide action:

1. Gain Clarity → This is where you develop a strategic plan by breaking each initiative into specific milestones, measurable outcomes, and action steps. Use the pillars of your business (team, business, empire, and lifestyle)

2. Ensure Alignment → Explain the reasons for the strategic plan you set. It’s not enough to have clarity; your team must understand why the plan exists (throughout all levels of the company). The benefit here is that questions can get answered quickly and genuine buy-in can be achieved.

3. Execute the Plan → Start implementing by rolling out the action steps within your team, followed by the other pillars as you hit milestones.

🛠 Tool: Notion

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📈 Trend: Top Cities By Unicorn Market Cap

Was there ever any doubt about where the most unicorns come from? Or, more specifically, where the most really large unicorns come from?

Elad Gil notes that generative AI is creating a super-cluster in the SF area. The US has 83% of the total market cap of companies that became unicorns in 2023 or later (compared to 60% before), but even more strikingly the SF area is at 63% of that (vs 33% before 2023).

During COVID there were feelings that SF was losing at least some of its importance as the undisputed center of the startup world. VCs were moving to Miami, founders were moving to NYC (myself included), and with the rise of remote work people were questioning the importance of being in SF.

While it’s likely that the gravity of the SF capital and talent ecosystems would have kept founders coming there as the top option regardless, the rise of LLMs has conclusively ended the debate for now.

If you’re building in AI, or in general, it would be objectively better for you to be in SF. You don’t have to be anymore, but it would be better.

💬 Quote: You Are The Pitch

As a founder, your job is to make people believe in you.

Your deck is just a sales document.

Its goal is to get you a meeting.

It is not the pitch.

If you’re early stage, investors are betting on you.

Every time I’ve had a big win as an investor, it’s been because of the founder.

Even if they were going after the wrong market. Even if their product wasn’t there yet. Even if they barely had traction so far.

So if you’re having trouble closing investors, look inward first. Are you making it impossible for them to not believe in you? Do they see you as a force of nature?

Because the biggest risk in the deal is you. Minimize it.

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Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Audience Building

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in this newsletter to get in front of 70,000+ founders.

I’ve learned that time and time again after running nearly 50 founder retreats over the years, but each time is a unique experience with new lessons.

A few weeks ago I partnered with Tyler Denk (CEO of beehiiv) and his newsletter Big Desk Energy to host 9 founders for a 5-day mastermind in Costa Rica.

We curated a hand-picked group of incredible founders (over $100M in combined annual revenue) to teach each other new things, build stuff, pick apart each other’s strategies, and generally help each other succeed.

(We also surfed, rented a boat, had a private chef all week, and more).

TLDR, it was a vibe. Here’s the recap:

I don’t live in Silicon Valley these days. I’m down in Charleston where, despite being an amazing place to live, you don’t get that same cracked founder energy on a daily basis like you do in SF.

So this retreat got me thinking… why not start bringing together some of that Silicon Valley energy more often like I used to? I’ve already set up the next one:

I’m hosting a 2-day Delegation Mastermind with my friends at Oceans.

We’ll be going deep on the right ways to use OpenClaw, Claude, and how to hire the right AI-fluent operators to give you time back and more leverage to let you grow faster.

The goal of the mastermind is giving you more execution capacity.

Here’s the deets:

• May 30th - 31st

• San Diego, CA

• Cost = $1,500 (transportation and accommodation not included/provided)

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Your CRM can’t do this.

“Tell me why we keep losing to our biggest competitor.”

“Build a report on our pipeline for my board deck.”

“Find everyone who mentioned the feature we just shipped, and send a win-back email.”

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Founder Retreat Takeaways

This retreat had both bootstrapped founders and VC-backed folks (including one from YC).

And from the opening night hot tub conversations to the presentations we each did to teach each other something new, there was a lot to learn and take in.

So I took a couple weeks to digest it all and start implementing some of it in my own business.

Here’s what I brought back with me:

Aim for Excellence

The youngest founder in our group inspired me quite a bit.

He pushed all of us in the group to aim for excellence. His company is in a crowded industry where differentiation is hard, but he’s managed to stand out by taking a counterintuitive approach to just about everything he does, and explicitly making his goal to be the best in the world at it.

A great example of this is cold outbound email.

A lot of people say cold outbound is dying because of the oversaturation of AI spam emails. I get 3-4 per day on a good day.

But one of the founders at the retreat, who used this strategy to get multiple billionaires to reply and become his clients, believes the opposite.

He believes that everyone’s digital footprint has enough breadcrumbs for you to draft hyper-personalized outreach that truly grabs attention… if you’re creative enough with it.

His approach goes against the traditional advice of not wanting to invest too much time and too many resources before knowing if something will be successful. He explicitly ignores this and ha at times spent an entire month proactively building something for a prospective client he hadn’t even contacted yet.

(No surprise: it landed him the deal.)

His thinking is that the traditional approach talks about what you can do, but in a world where anyone can easily do that now, he wants to stand out by showing what he can do.

When it fails, it sucks. But when it succeeds, it’s a big win.

Most people won’t commit 10+ hours of time to something that might not work out. The best founders will.

Pivot With Confidence

I had invited my buddy Keith from Lightfield but even though he wasn’t able to make it down, I wanted him to share his story with the crew — it’s inspiring.

After building Tome to 25M users, raising over $81M, and reaching a $300M valuation he and his co-founder decided to pivot.

They realized that LLMs, while being great at drafting first drafts, lacked the deep context necessarily for high-quality finished work on their own.

Their solution was building the data right into the product by creating an AI-native CRM.

But, seriously, imagine telling the investors you recently raised $81M from that actually you weren’t convinced enough your own idea was worth building further.

That must’ve been hard.

But they did it, and Lightfield is awesome. It’s the first CRM I’ve used that feels like I don’t need to do the tedious work at all, it does it for me.

Embrace the Cringe

Let’s be honest, LinkedIn is a pretty cringey place.

A public resume of your professional experiences, and a lot of braggy yet vapid content in your feed? Sounds bad.

But three of us at the retreat have over 40,000 followers on LinkedIn, including me.

One of the founders presented his entire LinkedIn strategy, and how it drives tons of inbound business for his startup (including converting over 25% of all outbound cold DMs he sends).

Here’s a way oversimplified version of his process:

1. Identify the right leads ahead of time

2. Add 25 of them as connections every day

3. Post content every day so they see you early (LinkedIn is more likely to show your posts to recent connections) including a mix of authority building, showing off your business, and straight up promotion.

4. Send them a DM a couple weeks after connecting

5. Follow up relentlessly (if necessary)

He’s used this to grow his business to nearly $10M in annual revenue and his process is very similar to what my team and I do for tons of founders at Megaphone Studio.

If you want to build your own inbound and outbound LinkedIn lead gen engine, book time with me here.

Custom Software is Here to Stay

Basically everyone there had used OpenClaw or Claude to build extremely specific, custom agents or software to support niche use cases within their business.

Tbh, I felt behind.

And since I came back it’s basically all I’ve been doing.

It’s let me cancel some of our subscription SaaS tooling, but not all.

And also tbh, would it really be a good use of time to do that?

While you should certainly automate what you can easily, you don’t to sync countless dev cycles into rebuilding everything from scratch just to save a few bucks. That’s a scarcity mindset.

Better to automate the easy things and use that time to invest in growth.

With that said, custom/personal software absolutely is here to stay. Just because the caSaaStrophe of 2026 is somewhat overblown doesn’t mean it isn’t real.

Your Environment is Everything

The #1 thing this retreat reminded me of (which was the first I’d done in 2 years) is that if you want to know where things are headed and feel inspired to push yourself harder, whatever you goals may be, there’s no better way to do it than being surrounded by people who are doing it too.

If this looks like a good time to you, join me and Oceans for the next one in San Diego in late May:

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Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 70,000+ founders.

We’d spent hours making spreadsheets with data on…

• Which companies various GPs at various firms had backed

• What they’d publicly said about their reasons for investing in those companies

• How the companies had gone on to do

• Whether we had folks in our network who could warm intro us

The simple truth is that founders who leverage data to shape how they spend their time during a raise will almost certainly close their round faster, and know what to say to the right investors when they have the chance to.

That’s why I’m co-hosting a session next week (on April 23rd!) on how to use data to fundraise faster with Usman Gul (the founder of Metal.so). He’s seen thousands of founders use Metal to close their rounds faster and knows what’s moving the needle for folks right now.

It’s totally free, and you can also get 20% off of Metal’s fundraising intelligence platform. It would’ve saved me a lot of hours back when we were raising.

RSVP (it’s free)

Anyway, here’s today at a glance:

Opportunity → Google Cloud For Context

Framework → Startup Rocket Framework

Tool → Warmy

Trend → The GTM Engineer

Quote → Do Reps

PS — Become a member to get access to my founder membership including an engaged community, fundraising support, fireside chats and more.

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Fundraising and building a startup require serious organization.

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You’ll also unlock $15,000+ in founder credits and up to 3 months FREE of Notion’s top business plan to run your startup more efficiently while raising capital.
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🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Taryl Ogle shares 10 fundraising secrets nobody tells you (Link)

• Martin Tobias on what to do to not “die” in a pitch (Link)

• Brett Calhoun on what the best founders do in their pitch (Link)

• Ali Sheikh’s X article on how to reach out to VCs (Link)

Growth

• Yacine Sibous on how he grew from 0 to 8-figure ARR in 13 months (Link)

• Haley Bryant on what the best 2026 GTM strategy might be (Link)

ICYMI

• You launched. Now what? PopHatch thinks through it with you. (Link)*

• The Boring Marketer on the barbell strategy that you should now have (Link)

• Federico Waldman on how early-stage hiring has completely changed (Link)

• Tim Stoddart on how to think small for big results (Link)

Upcoming Events

• RSVP here to my session on how to fundraise with data, co-hosted with Metal. You can also get 20% of Metal.so here to get signals like who the “most likely” investors to be interested in your round are (and who in your extended network can potentially intro you to them).

💡 Opportunity: Google Cloud For Context

Photos and videos are valuable assets.

In the age of LLMs, the context within them is more valuable.

Google Drive, Apple Photos, etc all let you store your videos but don’t let you dynamically search based on the context within them.

As Brycent notes, there are creator-centric applications here but the bigger opportunity is likely in B2B.

Imagine trying to find that one meeting where that guy you met once said that thing that is now relevant to another conversation you’re having.

Mission impossible.

But if you could vaguely describe it to an LLM, it could find it (I just found a tweet I’ll be using as inspo for a future deep dive that I saw once two months ago, by asking Grok to find it).

A few folks in the comments shared Eden which looks like it’s focused on creative work, so there’s likely still room here for a B2B-first option to win the market.

🧠 Framework: Startup Rocket Framework

Most frameworks talk about how to manage. This one talks about the full lifecycle, starting from ideation.

The Startup Rocket Framework is used as an operational guide, starting in the early days.

It walks you through ideation, validation, creation (of value), growth, and funding for a startup through the lens of how to acquire and retain happy, paying customers (instead of just writing a business plan or strategy doc).

🛠 Tool: Warmy

Sending emails but getting zero replies? It might not be your copy.

Many startups unknowingly have broken email deliverability, causing messages to land straight in spam folders.

That means lost leads and wasted outreach. Warmy automatically warms up your email accounts, protects your sender reputation, and keeps your emails landing in real inboxes. If email is part of your growth strategy, this matters.

Fix your deliverability before your next campaign.*

📈 Trend: The GTM Engineer

Remember “growth hackers”?

In 2026, the term feels like when you look back at your hairstyle from high school or college and think “why did I ever think that looked good?”

No? Just me? Ok moving on…

Anyway, back in the early/mid 2010’s growth hackers were these loosely defined hybrid roles whose job focused on simply producing rapid, scalable growth as their true north.

They were a sort of mix of marketer, ops person, analyst, and occasionally engineer too who ran low-cost experiments to find things that could scale.

Ultimately the term became an overhyped buzzword and the role lost any real meaning and basically got absorbed into other growth roles. You went from wanting to be a growth hacker to wanting to never be known as a growth hacker.

However this general idea is rising again, this time as the more professional (sounding, but also in approach) GTM engineers.

Pave, the compensation benchmarking platform, shows the rapid growth of the role

GTM engineers use new, LLM-powered tools and workflows to rapidly test and iterate on new ways for their startup to grow faster.

The main difference is that GTM engineers have the power of software engineering (thanks to Claude, etc) by default, so they can do even more with less.

It remains to be seen if GTM engineers will be here to stay or if their responsibilities will ultimately get absorbed into other roles.

💬 Quote: Do Reps

It’s not 10,000 hours, it’s 10,000 iterations.

Just putting time into something doesn’t do much.

It’s about focusing that time on testing, experimenting, and just plain trying.

Everything you do should be to prepare yourself for success.

Work to understand the environment you’re operating in, your goals, and how to reach them.

Doing that 10,000 times really will make it “unreasonable” to assume you’ll fail.

The key, as a founder, is being able to do that enough without losing time.

We all know speed is the most important thing.

So, think to yourself today: how can you speed up your cycle time? How can you go through the iterations you need to, faster?

Subscribe now

How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Audience Building

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in this newsletter to get in front of 70,000+ founders.

We’d spent hours making spreadsheets with data on…

• Which companies various GPs at various firms had backed

• What they’d publicly said about their reasons for investing in those companies

• How the companies had gone on to do

• Whether we had folks in our network who could warm intro us

The simple truth is that founders who leverage data to shape how they spend their time during a raise will almost certainly close their round faster, and know what to say to the right investors when they have the chance to.

That’s why I’m co-hosting a session on April 23rd on how to use data to fundraise faster with Usman Gul (the founder of Metal.so). He’s seen thousands of founders use Metal to close their rounds faster and knows what’s moving the needle for folks right now.

It’s totally free, and you can also get 20% off of Metal’s fundraising intelligence platform. It would’ve saved me a lot of hours back when we were raising.

RSVP (it’s free)

Anyway, here’s today at a glance:

Opportunity → API Access Control for Agents

Framework → Startup Narrative Design Framework

Tool → PopHatch

Trend → Data Center Building Boom

Quote → Spend Time On Things That Compound

PS — Become a member to get access to my founder membership including an engaged community, fundraising support, fireside chats and more.

Subscribe now

Every founder knows the pain of skyrocketing cloud infrastructure costs. But how to reduce AWS expenses without compromising your product’s potential?

Spendbase, in partnership with AWS, offers up to $100k in free AWS credits for the Founding Journey community.

All you need is a startup under 10 years old with a corporate website. Works for both new & existing customers (even if you got credits before).

Claim your AWS credits now

_{Want to stop seeing ads? Upgrade now. Want to get in front of 70,000+ founders? Go here.}

🔗 Houck’s Picks

My favorite finds of the week.

Fundraising

• Brett Berson on what to do if an investor isn’t pulling you forward (Link)

• Bilal Zuberi on the incorrect argument about early-stage funding (Link)

Growth

• Chris Orlob on how many sellers subtly put themselves below the buyer (Link)

• Tobby_scraper on how to write an app store description that converts (Link)

ICYMI

• Get access to Notion Fundraising Agent workflows (Link)*

• Elizabeth Yin shares one of her biggest pet peeves as an investor (Link)

• Jason Yeh on how most founders treat their network like an ATM (Link)

• Ayman Al-Abdullah on how CEOs who try to fix everything fix nothing (Link)

• Dave Kline shares 4 tests to know if your 1:1s are actually working (Link)

• Charles Cormier on what the winning founders do (Link)

Upcoming Events

• RSVP here to my session on how to fundraise with data, co-hosted with Metal. You can also get 20% of Metal.so here to get signals like who the “most likely” investors to be interested in your round are (and who in your extended network can potentially intro you to them).

💡 Opportunity: API Access Control for Agents

As the number of agents each business uses increases, new issues emerge.

One obvious one is around API access auditing. Ideabrowser outlines it well.

I would bet that most startups using agents are having each one use the same API keys.

But without an audit trail, diagnosing issues when they arise will be more challenging.

A tool that agents can reference to ensure they’re getting a unique API key for each service they’re interacting with, and keeping tabs on access on a simple dashboard, would solve this — and this is a market that seems clear to explode over the next few years.

🧠 Framework: Startup Narrative Design Framework

Startups need a coherent story.

Setting your mission, vision, values, culture, elevator pitch, and full pitch deck in vacuums is going to lead to misalignments.

Obviously, you’ll likely want to do these at different times but that doesn’t mean you shouldn’t aproach them all from within a singular framework.

Sean O’Brien’s Startup Narrative Design Framework intends to be just that.

It acts as a living, narrative document rather than a one-time exercise.

It uses a 6×3 grid to answer questions across three audiences: your team, the market, and other stakeholders (investors, partners, etc).

When you’re filling it out, identify and remove contradictions. And you’ll be left with a rock-solid narrative that makes everything from fundraising to selling or leading your team just a bit more coherent.

🛠 Tool: PopHatch

You launched, but growth is chaos. You’re shipping features and chasing threads, but the real signals are buried in the noise. Finding your first 100 users is a brutal grind—doing it alone is how founders burn out.

PopHatch is your 24/7 partner that thinks through the mess with you. It documents every test, connects the dots between your experiments, and gives you the logic to iterate until it finally works.

Founder pricing open now.*

📈 Trend: Data Center Building Boom

Even though as many as 25 new data center projects were canceled in 2025 due to local community pushback (re: expected electricity cost increases), demand isn’t slowing down anytime soon.

The bigger story here may be how this is seemingly directly impacting the new construction of offices for human workers.

It’s the digital workers who are being prioritized now.

Many people thought COVID would kill offices.

But it’s clear AI is having a bigger impact on them already.

💬 Quote: Spend Time On Things That Compound

Some businesses can scale with ads.

The recent rise (and alleged fraud) of Medvi is proof that you can scale to hundreds of millions, and potentially billions, in revenue just primarily through ads.

But that’s in a niche with an incredibly quick payback period and low costs to begin with, with a product that has extremely wide appeal.

Most startups cannot replicate that.

It’s not that ads are bad, it’s just that channels that compound are typically better.

The same is true for basically everything you do as a founder or a person more broadly.

Play longterm games.

You’re trying to build something, not just go from one thing to the next.

Subscribe now

How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Audience Building

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in this newsletter to get in front of 70,000+ founders.

If that’s you, you probably haven’t kept up with an underdiscussed trend in the NBA over the last 10 years… positionless players.

But maybe you should, because the exact same thing is now happening in the startup world.

Let me explain…

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Video is becoming the fastest way to build trust and move deals forward and startups using AI are winning.

In HubSpot’s upcoming session, “Video is Shortening Sales Cycles: Here’s How,” we’ll break down how modern GTM teams are using the newest generation of visual AI tools to increase creative output, educate buyers faster, and reduce friction in the sales process.

No hype. Just what’s working, what’s usable today, and how to test it without slowing your team down.

If you’re a founder or GTM leader looking to drive revenue with lean resources, this is a tactical session worth your hour.

Register Now

Positionless Basketball

What are you even talking about…?

I know, I know.

For most of you reading this newsletter, spending time paying attention to basketball doesn’t seem particularly interesting compared to building your business.

But stay with me on this.

A little over 10 years ago in the NBA, the Golden State Warriors debuted a lineup where all 5 of their players on the court were small, could pass well, and could shoot.

This proved dominant and was dubbed their “Death Lineup” since other teams were not well equipped to defend against it. Always, the other team would have some big-but-slow guy guarding a small-but-fast guy, which allowed the GSW to move around and get someone open for a good shot.

The Warriors’ players were effectively positionless since they were all relatively comparable in size and agility, unlike traditional teams that had a point guard, shooting guard, small forward, power forward, and center with defined roles.

Can we get to how this relates to startups…?

The “Death Lineup” (and the 10+ years of basketball strategy it has spawned) has been on my mind lately because it reminds me a lot of what’s going on with AI.

In basketball, it was GSW’s former power forward Draymond Green flexing his ability to also play against the opposing team’s center or small forward.

Right now we’re seeing a very similar dissolution of boundaries of traditional roles.

Founders have always worn many hats, but that should increasingly extend to your team members as well… regardless of stage.

But why make this analogy at all?

Be honest.

In 2026, would you rather have a “designer” or a “positionless designer” aka someone who can spec a product, prototype it, write copy, design landing pages, analyze data… you get the idea.

You should be optimizing for hiring high agency generalists first, while most candidates are still thinking of themselves like “I’m a backend engineer” or “I’m a designer.”

Specialists can be useful if they bring truly deep experience, unique POVs, and know how to ask the right questions but while most zig to pigeon-hole and “differentiate” themselves by niching down, you should zag and find the action-oriented, capable, and versatile unicorns who don’t care about their title.

Taken to its extreme, you could bring the specialists in as 1099 contractors / consultants / advisors / mentors, and keep your core team as AI-superpowered generalists.

They’re not scared of the Block layoffs nor are they looking to optimize their job security or their “role” but rather how much they can move the needle themselves in order for the company to be a success.

Those are the people who will turn your company into an AI-native, high-margin, forward-thinking place other high agency people will want to come work at. Maybe you’ll even get an angel check from Kevin Durant…

Subscribe now

How We Can Help

Become a member to get full access to our case study library, private founder community, and more.

We can also help your startup in a few other ways:

Content Creation

Let my team and I ghostwrite for your newsletter, X, or LinkedIn.

Growth

Grow your audience + generate leads with my growth service.

Fundraising

Share your round with hundreds of investors in my personal network.

Advising

I’ll help solve a specific challenge you’re facing with your startup.

Advertise in my newsletter to get in front of 65,000+ founders.