BUSINESS IDEA | STARTUP

Annual Letters Platform 📨  

Leader’s Digest

Available Domain: Annualletters.com

1. Problem/Opportunity❓

The Problem/Opportunity: Normal people get super pumped when a new Netflix series drops, or their favorite artist drops a new album. But us business nerds? We get excited when business leaders release their annual letters.

Take Stripe who released their annual letter earlier this week. These letters from the world’s leading CEOs always contain pearls of wisdom, but finding the time to read them can be tough. These are some of the best resources in the world to learn about business, so why not make them easier to consume? Here’s how.

Market Size: The global business intelligence market was valued at approximately $36.6 billion in 2023

2. Solution ✅

The Idea: A platform for tracking and consuming annual letters from business leaders

How it Works:

• A user signs up to the platform and selects what annual letters they want to track (e.g. Warren Buffett’s, Jeff Bezos’ etc.)

• The platform contains a comprehensive, searchable database of annual letters from CEOs, chairpersons, and business leaders, and users are notified when new letters drop

• Users can read the letters or listen to audio versions, enabling them to listen to them on-the-go (assuming you have permission from the copyright holder to do so)

• Each letter comes with an AI-generated summary, highlighting strategic priorities, leadership vision, and any other takeaways from the letter

Go-to-market: Start a Twitter account which summarizes the key findings from annual letters, build an audience, then build the software

Business Model: Freemium model where users get restricted access to letters for free, but pay a subscription for the full experience

Startup Costs: You could start this cheaply by building out the product incrementally. Create the Twitter account, then simple software that simply tracks and links to different annual letters and over time build out the functionality of the platform

3. How You’ll Get Rich 💰

Exit Strategy: Acquisition by a financial platform like Bloomberg, Morningstar, or Seeking Alpha.

Exit Multiple: SaaS companies typically go for 6x to 12x ARR depending on growth rates and user engagement.

TOGETHER WITH TURBOTENANT

Landlords, fire your property manager

Being a landlord can easily take over your life—finding tenants, collecting rent, rewriting leases, and drowning in paperwork.

Many landlords hire property managers to ease the burden, but they take 10% of your rental income—and let’s be honest, they rarely manage your property like it’s their own.

That’s why Sarnen Steinbarth founded TurboTenant in 2015—now trusted by 700,000+ landlords as the all-in-one property management solution.

The best part?

It costs less than a Netflix subscription, no matter how many properties you own.

We met the TurboTenant team last month and instantly loved their drive to be the best. So, we got them to hook up Half Baked readers with 20% off TurboTenant Premium!

Just use code HALFBAKED.

Oh yeah, and if you're not a landlord but know someone who is, send them the code and make their life easier!

DRUNK BUSINESS IDEA

Dog Mood Collar

• Tired of guessing what’s on your dog’s mind? Wondering if they’re truly happy to be your best friend? Gone are the days of misinterpreting a head tilt or a lazy eye roll.

• With the Dog Mood Collar™, you'll finally know if your dog is truly excited to see you or just hungry (again). Equipped with state-of-the-art color-changing technology, this collar translates your dog’s deepest emotions into vibrant LED hues. Green for happy, blue for sad, red for angry, the list goes on.

• Warning: The Dog Mood Collar™ may reveal truths you weren't ready for, like discovering your dog prefers your partner over you.

Vote

• ✅ Yes this actually exists

• ❌ Nope you totally made this up

JUST THE TIP

Trend 📈: AI Development Agencies

• AI is changing software development. Tools like Replit, Lovable, Bolt.new and other no code AI development tools mean that anyone can become a developer in 2025. Which by extension means that anyone can now open their own development agency.

• Anton Osika, the founder of Lovable, recently shared on Twitter the story of a No Code agency that made $173k last month, which is insane.

• We think a ton of these agencies will pop up in the near future, so now is the best time to learn these tools to capitalize on this opportunity.

Business Ideas

• No-Code AI Development Agency: Create an agency which specializes in building AI applications using no-code tools like Lovable.

• Udacity for No-Code Development: Create a platform dedicated to courses which teach how to use these AI tools

TOGETHER WITH THE RUNDOWN AI

Learn AI in 5 minutes a day

What’s the secret to staying ahead of the curve in the world of AI? Information. Luckily, you can join 1,000,000+ early adopters reading The Rundown AI — the free newsletter that makes you smarter on AI with just a 5-minute read per day.

Sign up to start learning.

THE MONEYSHOT

Making $20m from Selling a Newsletter

Newsletters, when done right, can become huge businesses.

Just ask this founder, who sold his newsletter company for a staggering $27 million, pocketing $20 million personally in the sale.

This is his story.

Sam Parr's entrepreneurial journey began in an unlikely place…Belmont University in Nashville, Tennessee. While most college students were focused on classes and campus life, Sam was busy running a hot dog stand called, I kid you not, "Southern Sam’s: Wieners as Big as a Baby’s Arm." College wasn’t all smooth sailing, though. Sam even spent 24 hours in jail while at college…

However in 2012, Sam made a bold move to San Francisco, diving headfirst into the tech scene. During his time there he co-founded Bunk, a roommate-matching app that was eventually acquired by Apartment List. He also (almost) landed a job at Airbnb, but the offer was rescinded after a background check revealed his previous arrest. This setback didn’t deter him though…

Spotting a gap in the market for non-technical founders looking for practical business advice, Sam launched Hustle Con in 2014, a conference featuring successful entrepreneurs sharing their stories. With just $6,000 as his starting budget, the first event brought in $50,000 in revenue, largely through sponsorships and volunteer support. But the event business was stressful, and Sam realized his true passion was in content creation. So he decided to pivot, leveraging the email list he built from Hustle Con to launch a new venture.

He founded The Hustle.

Initially, The Hustle was a daily newsletter which featured viral content and quirky stories about unconventional business practices. But by April 2016, he pivoted the focus to business and technology news, inspired by the success of newsletters like TheSkimm.

Targeting millennials interested in concise, engaging business content, The Hustle quickly gained traction, reaching 100,000 subscribers in its first year. By the end of the second year, it boasted 500,000 subscribers.

Sam's approach to growth was unconventional. Rather than relying on traditional venture capital, he raised $1 million from angel investors, including Tim Ferriss, David Nemetz, John Battelle, and Scott Belsky. When the newsletter hit 200,000 subscribers, he opened up investment opportunities to his readers, raising $350,000 in under 48 hours.

In 2019, Sam expanded the brand by launching Trends, a premium subscription service designed to help entrepreneurs spot emerging business opportunities.

By 2021, The Hustle had become a media powerhouse, catching the attention of HubSpot, who acquired the company for a reported $27 million. As a solo founder, Sam walked away with $20 million. Not bad for a simple newsletter.

Since the acquisition Sam has been pretty busy. He went on to co-found Hampton and is the co-host of the excellent My First Million podcast, the podcast that inspired us to start Half Baked.

Sam’s story is awesome. He put in the hustle and got the reward he deserved, blazing a trail for other newsletter creators trying to follow in his footsteps.

So what’s stopping you from following in Sam’s footsteps too?

1 - 1 FOUNDER FEEDBACK

We Need Your Help

We're on a mission to become the world's #1 entrepreneurship newsletter, but to do that we need your help. Got feedback, ideas, or thoughts on what you’d love to see next? This is your chance to help shape Half Baked. Darragh (our Head Baker) is opening up his calendar just for you. Click here to book a 15 minute call.