Subscribe here | Unsubscribe here | Aug 28, 2025 | FIV #91

✅ Today’s Checklist:

• Founderland: The most fun you’ll ever have closing deals

• How to transform your biz into a media co. (and win with AI)

• The skills that will make or break founders by 2030

QUICK LINKS

📈 Biz growth. A study of where AI gets its facts from (and how to win zero-click search)

🚀 Marketing. How this founder growth hacked Reddit to building a $1M ARR SaaS company.

📣 Leadership. Founder mode. An eye-opening essay by Paul Graham.

🌱 Personal development. Naval’s 22 vital habits for a better life packed into one simple tweet.

🛠️ Self-improvement. Is the best way to avoid avoidable errors simply to be more ‘careful’? In short: no. Here’s what to do instead.

Not Another Stuffy Founder Event—This Is Founderland

Founderland is built on a simple truth: the best deals happen when founders are relaxed, having fun, and connecting as humans first.

Think less “conference hall fluorescent lights” and more “energy, laughter, and conversations you actually want to keep going.”

Founderland is where founders have fun and deals get done.

👉 Apply now.

How to Transform Your Biz into A Media Company (and win with AI)

Here’s the raw truth: you don’t just run a company anymore—you run a media company.

Whether you’re building SaaS, selling sandwiches, or pitching seed investors, you’re in the same business: the attention business.

The uncomfortable part? You don’t get to opt out. You can build the smartest product in the world, but if nobody sees it, nobody cares. And if you don’t own your narrative, somebody else will: a competitor, a journalist, or an anonymous Reddit thread that defines you before you even know it’s happening.

👉 In the Attention Age, you either play the media game or you disappear.

Why Media Is the New Moat

Product used to be the moat. Build something great, and the market would come to you. That’s gone. Features get copied in months, prices undercut in weeks.

But the story? That’s untouchable.

• Stripe made payments cool not just through product, but through developer docs and essays that inspired a generation.

• HubSpot didn’t just sell software—they invented a movement: “inbound marketing.” Then they owned the language, the content, and the playbook.

• Tesla spends nothing on ads. Musk tweets, the media covers, and Tesla dominates global headlines without buying a billboard.

👉 The moat isn’t your code. It’s your content. Not the features. The feed.

Gut check: if TechCrunch ran a headline about your company tomorrow, would it be the story you want told? Write it down and spread your company gospel.

AI Just Changed the Game Forever

In the past, building a media engine required a team: content marketers, video editors, designers, writers. Today? You can build a distribution machine from your laptop.

The problem is most founders will use AI wrong. They’ll use it to automate mediocrity:

• 500 soulless blog posts for SEO

• LinkedIn updates that sound like they came from a corporate intern

• Newsletters that read like cardboard

That’s how you drown in noise.

The opportunity is to use AI as leverage—to scale you.

That means AI amplifies your voice it. It takes your ideas and spins them into formats, channels, and campaigns that make your content scroll-stopping.

The Founder Playbook: How to Win The Media Game with AI

Here’s the step-by-step framework you can use right now:

1. Nail Your Founder Narrative

Your story is the sharpest weapon you have. Without it, AI is just decoration.

Ask yourself three questions:

1. What’s the uncomfortable truth about my industry no one is saying out loud?

2. What problem am I solving that competitors are too afraid or too boring to talk about?

3. What do I believe that others dismiss?

Example: Instead of “We’re a better project management tool,” try, “Project management is broken because it was built for managers, not teams.” That’s a narrative.

How to sharpen it:

• Brain dump 10 contrarian takes about your market.

• Drop them into ChatGPT and ask: “Turn these into headlines that would stop a founder mid-scroll.”

• Pick the spiciest one and build content around it.

2. Train AI on Your Voice

Generic AI is forgettable. But trained AI can scale your unique founder voice.

• Gather assets: past blog posts, LinkedIn posts, investor updates, even spicy Slack messages.

• Feed them into a system like Jasper’s “Brand Voice” or ChatGPT custom instructions.

• Test it: prompt AI with, “Write a LinkedIn post about X in my style. Make it about what’s in it for my audience and make the information actionable.” Keep refining until it actually sounds like you and aligns with your goals.

👉 Pro tip: Record a voice memo ranting about your market, then transcribe it with Otter.ai or Descript. Feed that transcript into AI. Raw founder rants often turn into the best content.

3. Atomize Everything

Every founder moment is content fuel. Stop wasting it.

That investor deck? That’s 20 tweets.

That keynote? That’s a month’s worth of video clips.

That email to your team? That’s a newsletter draft.

Here’s the system:

1. Create one long-form piece each week (a talk, blog, or video).

2. Use Descript or OpusClip to slice it into short, subtitled clips.

3. Feed transcripts into ChatGPT: “Turn this into a LinkedIn post, a tweet thread, and an email draft.”

4. Schedule the pieces with Buffer.

One insight → 50 touchpoints. That’s distribution leverage.

4. Ship Short-Form Video

Text alone won’t cut it anymore. Video builds trust at founder speed.

You don’t need a studio. Use AI:

• Runway (love Runway Aleph for effortlessly manipulating elements within a video) / Veo 3 (built-in sound design but has room to grow in terms of hyperrealism) / MidJourney (now offers video—great for stylized and artistic outputs) → cinematic short-form video generation.

• Descript → edit and subtitle clips in minutes.

• Opus → slice long webinars into TikTok-ready highlight reels.

👉 Start small: record a 60-second founder take on your phone. Use Descript to clean it, subtitle it, and publish it. Do this weekly. In three months, you’ll have a media presence most startups can’t buy.

5. Stress-Test Before You Publish

Don’t “publish and pray.” Publish and know.

• Drop your headline into ChatGPT and prompt: “Rip this apart like a cynical Redditor.”

• Ask: “Would this make you click? If not, why not?”

• Run your pitch through Claude. Compare tone and clarity to competitor messaging.

This feedback loop makes your content sharper and harder to ignore.

6. Build a Rhythm

Media is a muscle. Consistency beats intensity.

Here’s a lightweight schedule:

• 1 hour/week → create one long-form asset (memo, podcast, keynote).

• 1 hour/week → repurpose into 5+ micro-assets.

• 30 minutes/week → test hooks and schedule distribution.

That’s 2.5 hours a week to build a media machine.

7. Add Fuel: Paid Media

Here’s the part nobody likes to admit: a lot of “viral” media isn’t organic—it’s amplified. Under the hood, even scrappy startups are running paid distribution to make sure their best stories actually get seen.

This doesn’t mean throwing cash at ads blindly. It means taking your highest-performing organic posts and putting $50–$200 behind them on LinkedIn, Twitter, TikTok, or Instagram to test amplification. If a piece resonates, scale it up.

👉 Action tip: Each month, pick your top 1–2 organic hits. Boost them. Use paid media as jet fuel for the stories that already work.

A Founder Challenge (Do This This Week)

Here’s my 7-day challenge for you:

• Day 1: Write down three contrarian truths about your industry.

• Day 2: Drop them into AI and generate 10 hooks. Pick one.

• Day 3: Record a 60-second video rant on that hook.

• Day 4: Use Descript or OpusClip to subtitle and cut it into two short clips.

• Day 5: Post the video + one LinkedIn text post.

• Day 6: Ask AI: “Turn this video transcript into a tweet thread and an email draft.” Publish both.

• Day 7: Review analytics. Take your best-performing piece and boost it with $100 in paid distribution.

By the end of one week, you’ve shipped across multiple platforms, created reusable assets, and learned which story deserves more fuel.

The Closing Punch

Here’s the takeaway: you’re already in the media business—you just may not be acting like it yet.

The founders who win in this era aren’t the ones with the fanciest features. They’re the ones who make themselves unignorable. They use AI as a tool to scale their strongest ideas into unstoppable distribution. And yes—they put a little paid media behind the winners to make sure their story spreads.

So don’t ask, “Do I need to become a media company?” You already are.

The only real question is: What story will you own—and how will you harness AI (and a touch of paid amplification) to make sure the world can’t look away?

Because in the Attention Age, silence is fatal.

And the founders who figure this out? They don’t just build companies. They build movements.

Sean’s Pick of The Week

A new World Economic Forum report mapped out what skills employers expect to dominate by 2030—and it’s a wake-up call for founders. The usual suspects like “reading, writing, math” are sliding out of focus.

What’s rising? Creative thinking, resilience, tech literacy, and emotional intelligence. In other words: the very skills that help you spot opportunities, adapt fast, and lead people—not just processes.

The kicker? AI and big data top the list. Pairing those hard skills with adaptability, leadership, and curiosity is what will separate the average companies from the category-defining ones.

👉 Translation for us: if you’re not building these muscles now—personally and inside your team—you’ll be behind the curve before the decade’s halfway over.

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