Start With What Sucks

In 2009, Yannick Rault and Jonatan Gomes were running nonprofit projects in Brazil.

But there was a problem with how they worked.

Every process lived inside spreadsheets - from tasks, budgets, and reports.

This meant that every update required manual copy-pasting across tabs and files, and it slowed everything down.

In 2016, they built a simple tool that moved data between Google Sheets automatically.

The tool let users connect multiple spreadsheets so that data entered in one would automatically update in others.

So instead of copying rows manually, teams could set up workflows that synced information in real time.

It grew into Sheetgo, a cloud-based spreadsheet automation platform.

By 2024, Sheetgo had hit 1,000 paying customers and crossed $1.7 million in revenue.

What looked like a minor workflow issue turned out to be a common, painful problem for thousands of teams.

And that’s the kind of signal founders should look for early.

A Simple Framework: How to Tell If a Problem Is Worth Solving

Great startup ideas don’t usually start with vision. They start with pain.

Here’s a simple framework you can use to test if a problem is worth solving:

1. Frequency
How often does the problem show up?

The more often it happens, the more likely someone will pay to fix it.

2. Intensity
Is the problem annoying or unbearable?

A tool that saves someone two hours a week has more value than one that saves them five seconds.

3. Spend
Are people already spending time or money on a workaround? If yes, there’s already demand.

4. Unsolved or badly solved
Is the existing solution ugly, slow, or manual? Clunky processes are clues.

Sheetgo grew by replacing spreadsheet hacks that people quietly hated.

The problems that matter are usually hidden behind half-baked solutions. Follow the hacks, and you’ll find real needs.

Builder’s Playbook: How Sam Parr Built Three Companies by Solving His Own Pain

While running a food truck business in San Francisco, Sam Parr spent his off hours reading business news.

But most coverage felt distant, corporate, and lifeless.

It didn’t speak to people building things from the ground up.

So his sought out to solve a pain he had: business media is boring.

In 2015, he launched The Hustle, a daily newsletter with short, sharp takes on tech and startups.

• Within one year, it had over 100,000 subscribers.

• Three years later, it crossed one million.

• And in 2021, HubSpot acquired it in a deal reportedly worth more that $20 million.

But Sam didn’t stop there.

He saw that many readers were builders.

They weren’t just reading startup stories. They wanted to start something.

So he launched Trends, a premium newsletter under The Hustle, that broke down emerging industries and startup ideas with real data.

It started as internal research for The Hustle team, but subscribers were hungry for more. So Sam turned that demand into a new business line.

Trends sold for $299 a year and brought in millions in subscription revenue.

Then came Hampton.

After the acquisition, Sam found himself facing a different kind of challenge.

He had money, freedom, and traction.

But no community, and no space to talk honestly about what came next.

He co-founded Hampton, a highly vetted private membership for experienced founders and executives.

In less than a year, Hampton had 400 paying members and was a million dollar business.

So how do you build three successful products, in three different stages of your career, all built by paying attention to a problem you feel first?

What You Can Take Away as a Builder

1. Start with a frustration, not a market size
   Sam didn’t ask, “How big is the media industry?” He asked, “Why does this coverage feel so out of touch?”

2. Test demand by talking to people like you
   Before building Trends, he saw reader behavior.

   He used his own pain as a filter. Ask yourself what your peers would pay to make easier.

3. Build adjacent to what’s working
   Each of his companies stacked on the last. He didn’t pivot randomly.

   He listened to the next problem each user base revealed.

4. Charge for what matters, not just what scales
   Hampton is high-ticket and intentionally small. Trends was simple but sticky. You don’t need volume. You need value.

Helpful AI Tool: Loops

Once you’ve spotted a recurring frustration, Loops helps you test it in the real world—without code.

Loops is a fast, no-friction landing page builder built for startup idea validation.

Use Loops to:

• Create a simple landing page in minutes

• Add a waitlist, email capture, or early pricing

• Run A/B tests to see what messaging hits

• Share with your audience and track response

If nobody clicks, you’ve saved weeks. If people do, you’ve got a reason to build.

Resources Worth Bookmarking

📘 The Mom Test by Rob Fitzpatrick
Still the sharpest guide on how to talk to users without getting lied to. Read it before you run your next user interview.

Get it here

🎧 Indie Hackers Podcast – Aaron Patzer (Mint)
Aaron built Mint because Quicken was clunky. He validated the idea with friends, launched quickly, and sold to Intuit for $170M.

Listen here

📄 How to Identify a Problem Worth Solving — by Saeed Khan
This post breaks down a practical framework for evaluating whether a user pain is truly worth building a startup around.

It includes key factors like urgency, frequency, and whether people are already spending time or money to solve it, helping you assess how real the demand actually is.

Read it here

Audience Corner

What’s one workflow, task, or process you’ve duct-taped together more times than you’d like to admit?

Hit reply and tell me.

Final Thought

Most people wait for inspiration to strike. But the best founders pay attention when things break.

They take notes when something sucks. They build when it sucks for others too.

That’s how real companies get started.

Until next time,
Sefunmi