The Underground Strategy for Bootstrapped Founders
Stop Underselling and Start Solving High-Value Problems
I’m going to tell you an underground strategy that savvy bootstrapped founders use to identify high-value problems and connect with business owners who are desperate to solve them.
I’ll show you how to stop underselling and wasting time on the wrong problems so that you can start maximizing your revenue and impact.
If you’re a bootstrapped founder, you’re fighting an uphill battle.
Limited resources mean every action counts.
Yet, most founders I talk to, including myself, fall into one of two traps:
Underselling Your Solution
You set your prices low, thinking it’ll bring in more customers.
Maybe you’re scared of rejection or feel you can’t justify higher rates without a big name or fancy marketing.
But here’s an even worse problem: low prices often attract the wrong customers, bargain hunters who churn fast, demand endless support, and never see the true value. Instead of growing, you’re stuck in a cycle of low revenue and high stress.
Solving the Wrong Problems
You’ve got a rough idea about what your customers need, so you build features based on gut instinct or the most likes on social media.
But without digging deeper, you might be pouring time and money into solutions that don’t actually matter to your market.
You end up with a product that’s “nice to have” instead of “must-have” and no one’s willing to pay a premium price for “nice.”
If either of these sounds like you, don’t worry, you’re not alone.
The good news?
There’s a way to flip the script.
Find High-Value Problems
Talk to Paying Customers Only
Set up 15-minute calls with current users, past clients, or even prospects.
Ask open-ended questions like:
“What’s the biggest headache in your business right now?”
“What’s stopping you from hitting your goals?”
“If you could solve one problem instantly, what would it be?”
Dig into Data
Review support tickets, survey responses, or churn feedback. Look for patterns, recurring complaints or requests that signal a deeper issue.
Listen Hard
Don’t pitch. Just listen. The goal is to uncover problems that are urgent, costly, and common across your target market.
For example, maybe you discover that small e-commerce owners are losing thousands because their checkout process is clunky.
That’s urgent (lost sales hurt now), expensive (revenue’s slipping away), and frequent (it happens every day).
Bingo—that’s a high-value problem worth solving.
Connect with the Right Business Owners
Identifying the problem is half the battle.
Next, you need to find decision makers who are feeling the pain, and most importantly have the budget to fix it.
Forget blasting ads or spamming LinkedIn.
Here’s a smarter way:
Go Where They Are: Find the communities your ideal customers already trust like industry forums, Slack groups, or niche events. For instance, if you’re targeting e-commerce owners, hang out in Shopify forums or local merchant meetups.
Be Helpful First: Share insights or answer questions without pushing your product. If someone asks about checkout issues, drop a tip based on your research. Build trust, not a sales pitch.
Spot the Seekers: Look for business owners who are actively complaining about the problem you’ve identified. They’re the ones ready to act and pay.
When the moment’s right, mention how your solution tackles their exact pain point.
No hard sell needed.
High-Value Problem Framework
I’ve boiled this down into a simple, repeatable process I call the High-Value Problem Framework.
Here’s how it works:
Problem Discovery: Use interviews and data to uncover urgent, expensive, and frequent problems in your market.
Solution Validation: Test your idea with a small group of target customers to confirm it hits the mark.
Outreach Strategy: Build a plan to connect with decision-makers who are searching for answers, without wasting time on cold leads.
What’s Next?
This Wednesday, I'm hosting a special live workshop with Bryan Harris—my go-to advisor for launching premium offers fast.
Here's what you’ll learn:
The #1 mistake SaaS founders make when monetizing their products (and how to avoid it).
How to get infinite users and clients without ads or social media.
3 questions to transform your SaaS idea into a high-ticket offer.
Exclusive access to Bryan’s High-Ticket Quick Start Action Plan.
You’ll leave with a clear roadmap to launching your $10,000 offer within 14 days.
Webinar Details:
Date: Wednesday, March 19th
Time: 1pm Pacific // 3pm Central // 4pm Eastern
Cost: FREE