Day 27 Transcript
NOTE: Today’s transcript is followed by an AI prompt that can be used with your AI provider of choice. Just copy and paste it into ChatGPT or Perplexity and it will help you answer today’s questions for your specific side hustle… the way a human teaching assistant would help you in an Ivy League university. If you’re eager for more on today’s topic, I’ve included a Secret Dessert Course at the very end — a bonus section that isn’t directly covered in today’s video but has a lot of value practical, hands-on value. That dessert also comes with its own AI prompt.
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Part 1: Analyze Incumbent Weaknesses
Rules were invented to perpetuate the status quo. So... Their rules are designed to ensure they win. Your goal is to change their rules, to play by your rules... until years from now someone younger, smarter, and way better looking realizes that your rules were designed so you win… and they do what a younger you did. Circle of life motherf….
Welcome to week 4, Day 27 of starting your side hustle! We’re taking 28 Days-- yeah, don’t get all weepy on me– 28 small steps-- to build a business that’s meaningful, impactful, and profitable. This week is all about scalability, and today’s topic is something called Counter-Positioning. Jargon for how to make your competitors’ strengths work against them. If you want to outmaneuver the people currently dominating your space– the ones who benefit from the status quo– you need to understand their sacred cows and build a business model they literally can’t copy without blowing themselves up. Counter positioning.
Our real life example is Brian Chesky, co-founder of Airbnb. When Airbnb launched, hotel chains dismissed the idea of regular people renting out their homes to strangers. Hotels’ business models depended on owning and operating massive real estate portfolios, with strict standards and high overhead. Chesky and his team counter-positioned Airbnb as a platform—no hotels, just people, flexibility, and unique experiences. If hotels tried to copy Airbnb, they’d have to abandon their core assets and brand promises. Airbnb’s model turned the industry’s strengths—reliability, control, and real estate—into liabilities, and built a moat– not a data moat but a counter-positioning moat that hotels couldn’t cross.
So let's apply these ideas to your hustle. The questions we’ll want to answer today:
1. What “sacred cow” in your industry are all incumbents trapped defending?
2. How could you make your business model incompatible with legacy players’ economics?
Every week I mentioned how I love Quizzy – our tiny little zombie squirrel. “Nuuuuuts!”
Ok. Let’s talk about why these questions matter:
Most founders obsess over beating competitors at their own game. But the real hustlers flip the script: they find the thing that every incumbent is terrified to touch—the sacred cow—and build their business around breaking that rule. Why? Because sacred cows are usually leftovers from a different era, and defending them keeps the old guard slow, bloated, and blind to new opportunities. If you can call out what everyone else is protecting, you can zig where they zag—and win customers who are sick of the status quo.
Here’s the twist: don’t focus on being different. Focus on being incompatible. If your business model makes money in a way that would actually hurt the incumbents if they tried to copy you, you’re untouchable. Think: Netflix and Blockbuster—Blockbuster couldn’t kill late fees without killing their entire P&L. Your goal is to make it so the old guard literally can’t follow you without setting their own house on fire.
Ok. Take a moment and try to answer the Day 27 questions for your hustle without AI and before you listen to the next section-- the 28-Day Ivy League MBA. I personally think it's useful to try to answer questions without AI first, but if you'd rather do that: The AI teaching assistant prompt will drop with today's case study... in a couple of hours. If you don't know what I'm talking about, check out Lunch Break Millionaire Day Zero... or go over to superserious.com where I’m posting daily transcripts. The AI prompts are there too. That's it. Hustle smarter.
Part 2: 💼 Practice Counter Positioning: Today's Ivy League MBA Skill
Day 27, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. Not sure how it took a whole month to get to a burger– but it’s the perfect lunch for today given what we just talked about. The MBA skill we’re going to pick up today is how to eat a sacred burger– how to play offense with counter-positioning.
The last couple of weeks have probably made you feel like David in a world of Goliaths. So today, we’re going to put a nice pebble in your sling. Most people spend their energy trying to beat the big players at their own game- like better features, lower prices, more hustle. But the secret to the most joyful of hustles is to change the game entirely, to make the rules work for you and against them.
Ok. Counter-positioning. As I said, that’s jargon for how to build your business in a way that makes the strengths of the big incumbents actually work against them. Your goal is not to be different. It’s to be incompatible. That’s a much better word.
Think about the hotel industry before Airbnb. Hotels had these massive portfolios of real estate. They had strict standards. They had armies of cleaning staff. And their brands were built on reliability. Then the guy we just talked about– Chesky and the Airbnb crew– came along and said, “What if we built a platform with no hotels, just people, and let the market decide what ‘home’ means?” Suddenly, all those hotel strengths-reliability, control, real estate-became liabilities. If a hotel chain tried to copy Airbnb, they’d have to throw out everything that made them who they are. They’d have to explain to shareholders why they’re letting strangers sleep in their assets, why they’re risking their brand on a bunch of random property owners they’ve never heard of, why they’re abandoning the very thing that’s supposed to make them safe. And that’s the beauty of counter-positioning: you build a moat not with data (Day 26), but with a business model that the old guard can’t imitate without setting their own house on fire.
So let’s try to make this real for your hustle. I want you to look at your industry and ask: what’s the sacred cow everyone is protecting? What’s the thing that every big player is terrified to touch, the rule they refuse to break? It’s exactly what drives comedy. Find the sacred cow. Eat it. That’s your opportunity. Most founders obsess over beating the competition at their own game, but you should look for more joy. You should find the one thing the old guard can’t or won’t change, and then build your business around breaking that rule.
Again… Your goal is to be incompatible. You want to make money in a way that would actually hurt the incumbents if they tried to copy you. Netflix didn’t just offer DVDs by mail-they killed late fees, which were a massive, massive chunk of Blockbuster’s profits. Blockbuster couldn’t follow without gutting their own business. That’s the move. Your job is to make it so the old guard literally can’t follow you without blowing up their own economics, their own brand, their own identity.
Take a minute and try to answer today’s two questions for your own hustle: what’s the sacred cow, and how can you build a model that makes it impossible for the big players to copy you without self-destructing? If you’re stuck, hit up the AI prompt in the post description later today. Let it help you brainstorm a few wild ideas. And if you come up with something cool-even if it’s not for you-drop it in the comments so someone else can run with it. Together! That’s how we hustle smarter.
Part 3: See Counter-Positioning IRL: The 28-Day Case Study
Don’t quit your day job—let it pay for your dream job.
This is Day 27, Part 3 of your evil, evil plan for financial freedom. You don't need to like or subscribe. I'm not doing this for the clicks. But if you’re leveling up from other creators you follow or know, introduce us. I want to help them level up, too. They deserve better than making rich people richer.
Ok. I’ll put up my grid…
But I have never in my life thought that the way to win a hustle was just to “out-feature” the competition. LOL. Turns out, the big players have sacred cows everywhere: they were obsessed with keeping creators locked into their platforms, obsessed with ad revenue, obsessed with controlling the algorithm. Everyone in the space treated “platform lock-in” like gospel—nobody wanted to let creators truly own their audience or their data.
So I decided to make creator ownership my religion. I went open source, made it easy for creators to export everything, and refused to take a cut of their revenue. That move was pure counter-positioning: the incumbents couldn’t follow me without nuking their own business model. If they tried to let creators own their data, they’d lose ad revenue and control. If they tried to go open source, their investors would riot.
The lesson? Don’t just be different—be incompatible. Make your business model so fundamentally at odds with the old way that the incumbents are trapped by their own success. That’s how you build a moat they can’t cross.
Takeaway: The best way to beat Goliath isn’t to fight on his terms—it’s to change the game so he can’t even show up.
Prompt #1 - Outmaneuver the Incumbents
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Prompt #1 - Outmaneuver the Incumbents ○
Today, you’ll learn how to use “counter-positioning”-the art of doing what the big players can’t or won’t-to carve out your own space in the market. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in competitive strategy, disruptive innovation, and market dynamics:
- **Professor Hamilton Helmer, Stanford (visiting at Yale):** Creator of the “7 Powers” framework and authority on counter-positioning.
- **Professor Michael E. Porter, Harvard Business School:** World’s leading expert on competitive strategy and industry analysis.
- **Professor Rita McGrath, Columbia Business School:** Specialist in spotting market inflection points and exploiting incumbent weaknesses.
**What Today’s Coaching Will Help You With:**
You’ll analyze where incumbents are stuck-by business model, brand, or culture-and design a strategy that highlights your strengths by doing what they can’t (or won’t) do, so you can attract customers who are ready for something new.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What is one thing the biggest players in your space refuse to change or are unable to offer?**
- Think about their business model, pricing, product features, customer experience, or even values.
2. **How could you position your business to highlight this difference-making it a reason for customers to switch to you?**
- Consider messaging, product design, customer service, or community-building that makes your approach stand out.
3. **What risks or tradeoffs are you willing to embrace that incumbents can’t (or won’t) because of their size, legacy, or reputation?**
- Are you willing to be more transparent, more niche, more affordable, or more innovative?
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### Step 2: MBA Skill – Counter-Positioning
Today’s MBA lesson is about counter-positioning:
> Counter-positioning means offering a product, service, or experience that the incumbent could copy-but only by damaging their own business.
- Start by identifying the “sacred cows” or unbreakable rules of your industry that the big players are stuck with.
- Ask: What would they have to give up (profit, brand, customer trust) to copy your approach?
- Design your offering and messaging to make this difference obvious and meaningful to your target audience.
- Remember: The best counter-positioning strategies make it costly or risky for incumbents to follow you.
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### Step 3: Coaching & Action Plan
After you reply, I will use the writings of Professors Helmer, Porter, and McGrath to:
- Help you clarify your counter-positioning strategy and how to communicate it.
- Guide you in identifying the incumbent weaknesses that you can exploit for maximum impact.
- Suggest ways to turn your “difference” into a rallying cry for your audience.
- Offer examples of businesses that won by doing what the big guys couldn’t or wouldn’t.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your first draft of a counter-positioning statement or strategy.
- I’ll help you refine your approach, sharpen your message, and suggest next steps for outmaneuvering the competition.
Secret Dessert Course
I love the term “flip the script.” We all intuitively understand it. But what if you took the idea literally? Imagine that there was an actual script from which all your competitors were reading. It would be like getting those glasses in They Live.
The AI prompt below will help you write their script. Not your script. Your competitor’s script. Your industry’s script.
No more unwritten rules. Because they’ll be written.
And those rules will be easier to break.
Just copy and paste the following prompt into your favorite AI assistant to enjoy Day 22’s dessert.
Prompt #2 - Reverse Engineer with the Anti-Playbook
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Prompt #2 - Reverse Engineer with the Anti-Playbook ○
**Today’s Focus:**
Uncover the unwritten rules of your industry-and systematically break them to create disruptive advantage. You’ll be coached by Ivy League faculty with expertise in strategic innovation and market disruption:
- **Professor Rita McGrath, Columbia Business School:** Authority on industry inflection points and escaping "best practice" traps.
- **Professor Hamilton Helmer, Stanford (visiting at Yale):** Creator of the "7 Powers" framework and expert in strategic rule-breaking.
- **Professor Karim R. Lakhani, Harvard Business School:** Specialist in digital disruption and disruptive innovation.
**What Today’s Coaching Will Help You With:**
You’ll identify the hidden assumptions governing your industry, then design an "anti-playbook" that turns conventional wisdom into your competitive weapon.
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### Step 1: Reverse-Engineer the Industry Playbook
**Answer these in a few sentences each:**
1. What are 3-5 "rules" everyone in your industry follows but never questions? (e.g., "Always prioritize scale over niche focus," "Premium pricing signals quality," "Growth requires heavy ad spend")
2. What outdated practices persist simply because "that's how it's always been done"?
3. What customer needs or behaviors does the current playbook ignore or dismiss as "not viable"?
4. What would happen if you broke your industry’s most sacred rule?
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### Step 2: Build Your Anti-Playbook
After you reply, I will use the writings of Professors McGrath, Helmer, and Lakhani to:
1. **Map the Hidden Rules:** Help you articulate the unspoken assumptions behind industry norms using McGrath’s "Inflection Point" framework.
2. **Identify Breakable Rules:** Apply Helmer’s "Power Progression" to pinpoint which rules to violate for maximum strategic advantage (e.g., counter-positioning, scale economics).
3. **Design Disruptive Alternatives:** Guide you in crafting anti-rules using Lakhani’s digital disruption principles (e.g., "If everyone uses paid ads, build word-of-mouth engine").
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**How to use this prompt:**
- Respond with your answers to the questions above.
- Your Ivy League panel will return a tailored anti-playbook with actionable rule-breaking strategies.
*(This exercise combines McGrath’s inflection point analysis, Helmer’s power frameworks, and Lakhani’s disruption models.)*