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Hi {{first_name}},
thank you for being part of this newsletter.
As I mentioned before, the main goal of The Bootstrap Insider is simple: to help you find equity-free prize money and opportunities that actually move your startup forward. That's the hard business side.
But on Sundays, I do something different.
Bootstrapping can be a lonely game. While everyone else is celebrating fake VC-funding rounds on LinkedIn, we are the ones actually figuring out how to survive on cash flow.
Thatās why Sundays are for the unglamorous reality. I share the behind-the-scenes learnings, the roadblocks, and the raw stories of what it actually takes to build a business without a safety net.
Itās a new format, and I want to make sure it hits the mark for you.
Do me a quick favor: Hit "reply" and just say "Yes" if you want more of the unpolished behind-the-scenes stuffāor tell me what your biggest headache was this week. I read every single one.
Best,
Bartosz
Letās go!
Iām about to trash the single most repeated piece of advice in the startup world.
Every mentor, every blog post, and every marketing textbook preaches the exact same mantra:
āYou need to define your target audience. Build your empathy map. Figure out their age, their income, their hobbies.ā
So, we sit down and define our ideal customer: "Male, 30-45 years old, high income, likes tech." Let's call him Klaus.
But a while ago, I had an "aha-moment" that completely shattered this approach for me. I realized that the classic concept of a "target audience" is a massive conceptual flaw. Itās the reason why so many brilliant products launch to absolute crickets.
Here is the hard truth:
We need to stop thinking in target audiences, and start building for ROLES.
Why? Because the exact same person makes completely different purchasing decisions depending on the role they are currently playing.
Think about our guy, Klaus. When Klaus sits at his desk at 9:00 AM in his role as a Head of Department, he has a very specific set of fears, needs, and problems. He needs to look smart in front of his CEO. He needs to cut costs. But when that exact same Klaus steps into the role of a loving father at 5:00 PM to pick up his kids, his purchasing triggers completely flip. He isn't looking for efficiency anymore; he's looking for safety, love, and connection.
We don't build products for Klaus. We build products for the role he is playing right now.
I actually have an infographic hanging on my office wall to remind me of this every single day. It keeps me from falling back into the demographic trap. It breaks down into three simple visual anchors:

š The Costumes (The Fluidity of Roles): Our identity is fluid. Every day, we put on and take off dozens of different roles like costumes. A static demographic profile is a trap. If you sell to a demographic, you sell to a ghost.
āļø The Rules (The Pillars of Expectations): Every role has rules. Sociology calls them Must-, Should-, and Can-Expectations. What must the department head do to avoid getting fired? What should the father do to be socially accepted? And how can he go above and beyond to get a standing ovation?
š¬ The Stage Props (The Internal Drivers): This is where it gets deeply psychological. When we act in a role, we actually use products merely as "props" for our personal stage. The expert buys an expensive course to appear competent. The father buys the safest, most ridiculously over-engineered car seat to feel like a protector.
Read that last part again. People don't buy from you because of a feature list. They buy from you to feel more competent, more independent, or more respected in their current role.
My Takeaway for Your Everyday Hustle
These reflections led me straight down the rabbit hole to the Jobs-To-Be-Done (JTBD) Framework. It is the only logical consequence.
If you haven't heard of it, JTBD was popularized by the late Harvard Business School professor Clayton Christensen in his brilliant book Competing Against Luck.
The core premise of the book is mind-blowingly simple, yet it changes everything you know about product building: People don't buy products. They "hire" them to do a specific job in their lives.
And here is the kicker that connects right back to our friend Klaus: The "job" Klaus needs to get done changes entirely based on the role he is playing at that exact moment.
Once you see business through this lens, you can't unsee it. It applies to software, services, newsletters, and pitch decks.
So, before I write a single line of code, design a landing page, or type an email to this community today, I force myself to answer one single question:
"In what specific role is my customer right at this very momentāand what 'prop' do they need from me to successfully master this job?"
Anyone who understands this perspective shift from "person" to "role" stops building nice-to-have products. They build painkillers. They build tools that people desperately reach for when the pressure of their role gets too high.
Are you building a vitamin for Klaus? Or are you building a painkiller for the Head of Department?
P.S. I want to put this to the test right now. I want to make sure the Bootstrap Insider is delivering the exact "props" you need for your current role.
Hit "Reply" to this email and tell me in one short sentence: What is the specific role you are playing in your startup right this second (e.g., The overwhelmed marketer, The nervous closer, The exhausted coder), and what is the #1 thing you are struggling to get done?
I read every single reply, and Iāll use your answers to source the exact playbooks you need for next week's issue.
Let's get to work!
Do you know a fellow bootstrapper who needs to read this?
Entrepreneurship can be lonely, but it doesn't have to be. If you enjoyed this story, forward it to a friend or co-founder who needs a little motivation today.
About The Bootstrap Insider
The Bootstrap Insider is a newsletter that helps startups discover and apply for pitch competitions, ensuring they never miss out on valuable opportunities. It addresses the problem of missed funding and exposure chances due to lack of information. Created by Bartosz Kajdas, an experienced entrepreneur, venture builder and Pitchtrainer, the platform leverages his expertise to provide timely and relevant updates.
Disclaimer:
This newsletter is for informational purposes only. We do not guarantee the accuracy or completeness of the information provided. We shall not be liable for any damages arising from the use or non-use of the information provided.