I Lost My Job Because of a Swagger
In the fall of 2023, I lost my job. At that time, I worked for T-Mobile as a contractor in a digital product field. The team loved me, the manager loved me. They wanted to keep me. But unfortunately, the team I was in was dismantled, everyone joined other teams, and I got stranded. I was a remote contractor working on Washington (state) time from Florida, nobody knew me in person and, frankly, didn’t have a complete picture of my capabilities. I got an interview with another T-Mobile team right away, but they passed.
The way it was explained to me, it was because “I didn’t say a specific word the team expected to hear.” The word was swagger. I was asked what I need to request from an API team. I gave a good answer, but I did not say the word “swagger.” The job went to someone they knew personally.
I could not believe the stupid word made someone pass on a talented and experienced Product Professional like me (I am bragging a little here, but I am still sorta trying to be objective. I am that. I am.)
I was furious.
At the word, the question ambiguity, the world instability, and the weather.
And that’s when I decided that I was going to start my own consulting business because enough is enough. I felt powerful. Strong. I knew my stuff. And I was ready to show the world who I was.
Score
Literally. Next came Score. I sought mentors. I knew nothing about how to start, needless to say succeed in, a business. I wanted to leverage anything I could as fast as possible to take off and rise above employment to the league of entrepreneurs.
And, man, oh man… I didn’t know how much I didn’t know.
Long story short, within the next couple of years, I learned so much about launching a small business and saw so many mistakes beginner business owners were making that I simply had to say something.
If you’re a small or not-yet-large business, this article is for you.
Read carefully, because the gap between surviving and scaling often comes down to the strategy you apply when money is tight and options are limited.
Sell to the Wealthy
In a recent video, Alex Hormozi outlines why many businesses, especially service providers, should focus on large or wealthy clients. His reasoning is clear:
- High Structural Churn. Small businesses fail often, especially in the beginning. The revenue balance is fragile. They hit a bad month and stop paying for marketing, website support, and doughnut delivery.
- Babysitting. Small business owners often lack the underlying infrastructure, sales skills, or pricing strategies to succeed, meaning they demand far more hand-holding and custom help than they can actually afford.
- Financial Strain. Because a modest subscription or fee represents a massive percentage of a small business’s cash reserves, their expectations are unrealistically high, leading to constant dissatisfaction and price negotiations. Don’t even get me started with them complaining that their AI designed their banner better than you, and for free. It doesn’t matter that you immediately spotted 9 common design mistakes in that banner that would never be published in a respectable ad.
- Operational and Team Burnout. It’s just exhausting. Constantly swimming through a shark tank of low-end customers and those who most likely don’t appreciate your expertise, while the endless cycle of onboarding and offboarding strains company operations and ruins team morale.
Simply put, selling to larger, well-capitalized customers results in higher lifetime value (LTV), lower relative churn, better financial stability, and the ability to price your services appropriately for the actual value delivered.
You might be thinking to yourself right now: If selling to wealthy clients is so much better, how do I get those clients when I’m just starting out? A fair question!
And I don’t have the explicit answer I can squeeze into this article. There are ways, and most of them very much circle around your authority and positioning. But perhaps the most important thing to ask yourself is: who do I truly want to work with?
Maybe a wealthy customer is exactly who you don’t want to help. Maybe your client is exactly someone who doesn’t have a lot of money to start or doesn’t earn a lot of revenue. Maybe they are even a nonprofit… and maybe this is exactly why you want to work with them.
Who am I to tell you who to work with, Alex Hormozi? Just kidding.
He knows his stuff. I would consider his perspective, especially if you have not deliberately decided that your customers will have little to no money.
Find the Right Help
If you’re a small startup with limited funds, top-tier professional contractors usually avoid your segment. It’s not personal. It’s economics. Well, worry not, it’s mutual. A new business owner rarely has a lot of cash to burn on help before profits start rolling out, so you can’t afford them anyway.
So, what do you do?
You do creative and intentional outsourcing.
Here’s how to get the support you need without pretending you’re a big fish.
Hire students who need portfolio work
- Use platforms like Behance, design school boards, or even Instagram DMs
- Expect slower turnaround and guidance needs
- Give clear briefs. Make it easy for them to shine
Tap into skilled family or close network
- Got a cousin who’s a UX designer? Or a brother-in-law with SEO skills?
- Offer non-cash value: e.g., free childcare, vacation stays, or even barter deals like cooking for their family
- Family wants to help, but they need to see value and boundaries
Hire offshore via Fiverr, Upwork, or OnlineJobs.ph
- Always vet with small paid test tasks
- Ask for before-and-after examples or Loom videos explaining their work
- Use country-specific forums to understand pricing and norms
Learn to do things yourself
- This isn’t about becoming a full-stack developer
- It’s about becoming dangerous enough to do, direct, or delegate well
- Learn the basics of design, funnels, email, or even video editing, enough to judge quality and bridge gaps
Get Your Hands Dirty. In the Right Dirt.
There will be things that you either can’t outsource or simply want to do yourself. And if it doesn’t compromise the delivery of your main services, you can definitely take on some operational activities. The question is: should you?
Here is a quick filter you can use to decide if taking on any business chores yourself is a good idea:
- Does it directly generate revenue or grow your audience? → Learn to do it
- Can AI tools accelerate or automate most of it? → Learn the tool and get started
- Is it repeatable, scalable, and not super technical? → You can probably master it fast
- Would doing it yourself help you manage future hires better? → Worth learning
Examples:
- Learning Canva or Figma? Yes
- Writing your own landing page copy with ChatGPT’s help? Worth a try
- Doing your own legal contracts? Nope. Hire a pro.
Some things are not worth skimping on. Here’s a good rule of thumb:
If it defines your brand or is a high-trust item, pay full price.
- Logo & brand design: If done wrong, you’ll redo it multiple times
- Website development: Avoid template messes that break
- Legal, tax, and financials: Amateur mistakes are expensive
- Core software infrastructure: Bad tools slow you down more than you realize
Be frugal, but not where it costs you your credibility or compliance.
Never Stop Learning
If you’re doing it yourself, do it well. Here’s how to find quality self-study resources:
- Look for practitioner-led content: Not theory, but from those who do these things daily
- Avoid YouTube rabbit holes: Instead, buy 1–2 solid, structured courses
- Ask: does this guide show me how to think and make decisions? If it just shows buttons, it’s incomplete
- Leverage AI to accelerate learning: e.g., paste in course outlines and ask AI to explain key concepts or help create a checklist
- Follow creators who build in public: You’ll learn from their process, not just their product
Examples of good self-study platforms:
- UpGreatly (Created by a small business for small businesses)
- Skillshare (great for creatives)
- Udemy (look for highly rated, recent courses)
- AI + YouTube for execution support
Final Word
If you’re still small, it doesn’t mean you’re weak. It just demands smarter plays. Big businesses buy speed. You buy resilience, creativity, and personal skin in the game.
You don’t need to pretend to be bigger. You need to be sharper.
Like a shark’s tooth. 🙂
