Excel

A few years ago I was hired to perform due diligence on a $100 million dollar startup’s Series A round.

Part of the due diligence included building the company’s pro-forma financial model. This particular business was complicated which led to a relatively complex financial model.

There was a point I became frustrated as the Excel file became bloated, overcomplicated and almost unusable.

At the time, I had recently learned software development and something clicked.

In software, the backend (where the data lives) and the UI (what users interact with) are separate.

You get to organize and structure your data optimally and THEN connect it to an interface designed for the user.

In Excel?

It’s all mashed together. The UI is the backend. Each tab is a 2D array where data is stored AND where the user interacts with it.

No separation. No abstraction.

I took a step back and considered how to organize and structure the data given this limitation.

I rebuilt the model and it forever changed how I build any spreadsheet.

A short time later, I built a financial model for another startup.

The CTO looked at it and said, “This could be a SaaS product.”

Even though my “Excel insight” transformed how I worked, I never saw it as something that might be valuable to others.

Insights » Ideas

Fast forward to this past week, and I shared this insight responding to a post on X:

The response was strong. I have limited followers on X (<200) so to receive over 9,000 views in under 24 hours is a good signal. Further, the bookmarks-to-likes ratio of 55% is VERY high.

I thought, should I build a course? To test this further, I spun up a landing page to see if I can get actual signups.

Will there be real interest? Time will tell. I will update you in future issues.

The point is that insights from your experiences are a tremendous, yet an often overlooked source for ideas. The problem is you are either unaware of or discount their potential value to others.

Let’s walk through five ways to uncover your valuable insights. Each section includes a prompt to get you thinking.

5 Ways To Uncover Your Insights

1. Intersection Method (Venn Diagram Thinking)

Your unique value often lives where your skills and experiences overlap. Possibly the greatest example of this comes from Apple.

Steve Jobs famously audited a calligraphy class after dropping out of college. Years later, that seemingly unrelated experience shaped the typography and aesthetic design of the first Macintosh. It became the first computer with beautiful fonts and proportionally spaced type.

Jobs didn’t invent calligraphy or computers.

His insight came from the intersection of the two. How something elegant and human could elevate something technical and cold.

That intersection became part of Apple’s DNA.

How could overlaps in your experiences be hiding great insights?

Prompt: What do I see in [X] because I’ve also done [Y]?

2. The Frustration Filter

The things that once annoyed or confused you are gold.

You have probably used or heard of Slack, the chat-based collaboration platform.

Slack was born out of a video game studio. The studio’s team hated email as much as internal status meetings so they built a tool to solve for both.

The video game studio ultimately failed. Months before going out of business, the founder used what little money remained and hired a dev shop to make their internal tool production ready. The rest is history and their initial frustration became one of the fastest growing B2B software products ever.

Necessity might be the mother of invention but frustration is the father.

Prompt: What do I understand now that used to drive me crazy?

3. Pattern Recognition

Insights hide in repetition. Watch what others always ask you and make certain you’re listening for potential problems underlying the questions.

Marie Kondo is a famous tidying consultant from Japan. Marie noticed her clients struggle with clutter, overwhelm, and emotional attachment to stuff.

Her insight was that people didn’t need another storage or organization system, they needed a philosophy for letting go.

That insight resulted in global brand including a best selling book and a Netflix show.

You likely recognize patterns daily but have you ever stopped to think more deeply about them?

Prompt: What do I get asked about more than anything else and what is at the core of the question?

4. Undervalued Obvious

What’s obvious to you and amazing to others?

Last week I wrote about the Expert’s Curse and how it can limit effective communication. It can also prevent you from relating key insights.

In James Clear’s famous book Atomic Habits, the core idea isn’t revolutionary because everyone knows good habits are important.

However, the central framing, “Habits compound like interest.” fueled one of the best-selling books of the decade and one I re-read annually.

Your obvious is someone else’s epiphany.

Prompt: What do I assume is “basic” that consistently blows people’s minds?

5. The “That’s Interesting” Test

Listen to what others latch onto when you speak or write.

Probably the quote that launched Andrew Huberman to science and wellness podcast fame was (paraphrasing), “The first light you see in the morning sets your clock for the day.”

The “That’s Interesting” Test isn’t about going viral though.

It’s about noticing when something sticks with people more than it stuck with you.

If someone replies, “Wait, say that again,” don’t brush it off.

Write it down. Repeat it. Test it again. That might be your next product seed.

Prompt: What comment or phrase have people often asked me to explain or expand upon?

The Next Step

If you use these methods to become more aware of your own insights you will uncover a treasure trove of potential ideas.

The important step is to share your insights with others.

When something resonates whether it’s a comment, a quote, a process, or a belief-pay attention. That’s a signal.

You don’t need to build a full product yet.

You just need to test if the interest is real.

Here’s how:

• Turn the insight into a follow-up post, a short guide, or a landing page with a tool like Kit

• See if people engage, click, save, or ask for more

• Start small. Let the signal lead you.

To go further, you can use the FI₂R₂ST method I describe in a previous issue (99 Problems) to validate business ideas.

The best ideas come from your unique insights. Once uncovered, test for validation then get started building!

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.