Day 22 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: Implement Value-Based Pricing
When you sell yourself cheap, you're shitting on the people who actually paid what you're worth.
Welcome to week 4, Day 22 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Alright. I messed this whole series up. Today’s session is about monetization and pricing and it should have been done the week before last– before sales week. I suck. And I’m sorry.
All this week we’re going to focus on what’s called “operational leverage”— building processes and systems from the get-go to handle scalable growth (think monetization, automation, partnerships) and that word– scalable is super important because we’re going to touch on defensibility (a fancy word surrounded by other fancy words like data moats and churn reversal– all concepts that I’ll explain). Today’s focus on pricing is about operational leverage but it would have been good to do earlier. To be fair, I touched on pricing on Day 10 when we were building our website… but in retrospect, it wasn’t nearly enough.
Ok. Enough self-flagellation. Pricing might sound easy and straightforward but it's usually where most hustlers stumble. It’s not because they don’t understand their costs or their market. It’s because they don’t understand value. Too many people price their work like they’re freelancing– based on hours– not outcomes. And that’s a problem because hours don’t scale. Value does.
The real life example here is an oldie but goodie. Jason Fried, co-founder of Basecamp (formerly 37signals). Early on– like 20 years ago– Jason and his team resisted the urge to price their project management software by the hour or feature. Instead, they focused on the core value their product delivered: clarity and simplicity for teams drowning in complexity. They set a flat monthly price, betting that customers would pay for peace of mind. That value-based pricing model helped Basecamp scale to millions in recurring revenue and a fiercely loyal customer base– which included me. Jason’s approach proves that when you price for outcomes—not hours—you unlock real growth and freedom.
Ok. The two questions we’re tackling today are going to help you engineer a pricing system that grows with your hustle:
Question 1. What customer behavior data could reveal hidden premium pricing opportunities?
And question 2. How could you implement dynamic or behavioral pricing without alienating your base?
Have I mentioned lately that I love Quizzy! He always looks like he’s sneaking up on you– about to pounce!
The first question is meant to force you to look beyond surface-level metrics like sales volume or average transaction size. It’s meant to challenge you to dig into how your customers actually use your product or service, what they value most, and where they’re willing to pay more. Understanding behavior—like which features customers use most often or what drives repeat purchases—will help you figure out how to upsell, how to bundle, how to create premium tiers.
Question 2 gets into dynamic pricing—which is a fancy way of saying that you’re adjusting prices based on demand, on behavior, in context. It can be a powerful tool for maximizing revenue. But it’s a double-edged sword. If done poorly, dynamic pricing can make loyal customers feel…. less than… exploited… undervalued. And that’s a no-no. So this second question should make you think about how to introduce flexibility in your pricing while maintaining trust and transparency with your audience.
Answering these questions for your hustle really matters. Because your pricing strategy needs to be rooted in real-world data—not guesswork or gut feelings or a well-crafted ChatGPT prompt. You need to constantly gather data that’ll help you think through where your customers see the most value in what you offer– what your competitors offer– and how you can monetize that value effectively. The second question is just as important because your pricing needs to evolve as your business grows.
Pricing isn’t about numbers—it’s about psychology, strategy, storytelling. This might sound obvious but you need a path to deepening your share of your clients wallet without alienating them. You need a path to a data-driven pricing model that will let your business scale. Because scaling your business demands a pricing strategy that grows with you—grounded in data, aligned with value, and built for long-term success.
Ok. Take a moment and try to answer the Day 22 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: 💼 Play with Behavioral Economics: Today's Ivy League MBA Skill
Day 22, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. It’s Monday so let's go back to our usual overpriced salad. And the MBA skill we’re going to pick up today is something called– broadly– behavioral economics.
Again– a boatload of jargon (like data-driven dynamic pricing) but I’ll explain it in plain English. Pricing isn’t just about picking a number that “feels right.” The best hustlers– whether they’re solo or working in a company– use data to find out exactly what their customers are willing to pay, and then they use psychology to make those prices stick. That’s dynamic pricing, and it’s everywhere. Airlines, ride-shares, streaming services—they’re all changing prices based on demand, timing, and what they know about you. But you don’t need to be Amazon to use these tools. You just need to know what data to look at, and how to use it to create win-wins for you and your customers.
Let’s break it down. Dynamic pricing means your price isn’t set in stone. Instead, it flexes based on what you learn from your customers—like how often they buy, when they buy, what features they use, or even how they respond to special offers. Maybe you notice that a certain segment of your audience always buys your premium version, no matter the price. Or you see that people who come in through a specific channel are more likely to upgrade. That’s gold. That’s the data that tells you where you might be leaving money on the table.
But here’s where behavioral economics comes in. People don’t always act rationally about price. Sometimes, a higher price makes your product seem more valuable. Sometimes, a discount at just the right moment gets someone off the fence. Anchoring, decoy pricing, scarcity—these are all psychological levers you can pull. Anchoring is when you show a higher price first so the actual price seems like a better deal by comparison. Decoy pricing is when you add a less attractive option to make the product you really want people to buy look like the smartest choice. And scarcity is what luxury brands always do-- they make something feel limited or in short supply so people feel more urgency to buy it before it’s gone.
The trick with all three is to not use them as tricks… It’s to use them ethically, to help your customers feel good about what they’re getting, not tricked or squeezed or manipulated. And that’s hard… but worth it.
Now, let’s tie this back to today’s questions. When you’re asking, “What customer behavior data could reveal hidden premium pricing opportunities?” you’re looking for patterns. Who are your power users? What features do they love? When do they buy, and how much do they spend? Dig into your sales data, your website analytics, even your customer emails. Look for signals that some customers are willing to pay more for certain things—faster shipping, exclusive access, custom features, or just the status of being your “VIP.” And when you ask, “How could you implement dynamic or behavioral pricing without alienating your base?” you’re really asking, “How do I make sure my pricing feels fair, transparent, and rewarding?” The answer is to test small changes, communicate clearly, and always offer real value. Maybe you introduce a premium tier with extra perks, instead of raising prices for everyone. Or you use time-limited offers to reward loyalty, not punish latecomers.
Take a sec and look at your own data. Who are your best customers? What do they buy, and what else might they pay for? Sketch out a few pricing experiments you could run—maybe a premium offer, a bundle, or a limited-time discount. Don’t just guess. Use your numbers, and pay attention to how people respond. If you can, talk to a few customers and ask them what would make your offer a no-brainer. And if you’re worried about backlash, be up front about why you’re trying new things—most people appreciate honesty, and you’ll learn faster if you keep the conversation open.
Keep telling yourself, the smartest pricing isn’t about squeezing every dollar—it’s about matching value to the right customers, at the right time, in a way that feels good for everyone. When you use data and psychology together, you’re building a business that can grow and adapt as you learn. That’s how you hustle smarter.
Part 3: Practice Pricing Strategy: The 28-Day Case Study
This is Week 4, day 22, Part 3 of Lunch Break Millionaire. This is the segment where we #BuildinPublic– where I answer the daily questions every hustle should– using the MBA skills we just learned– and showing my work– sharing how I’m building my hustle from scratch-no filters, just the real journey. You don't need to actually 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 learn from them and help them level up, too. We all deserve better than just making rich people richer.
Ok. I am still thinking about pricing for Metatorial and superserious. I hope that never stops. I produced a bunch of subscriptions pricing charts like this:
But I’ve known from day 1 that I can’t just slap a number on it and call it a day. This isn’t a commodity— no one else has anything like it. And how much is it worth to a creator to reclaim control over their audience and revenue streams? Pricing something like that requires nuance because the value isn’t just in the software—it’s in the empowerment it provides.
Here’s how I answered today’s questions:
Question 1: What Customer Behavior Data Could Reveal Hidden Premium Pricing Opportunities? I started by asking myself: What do creators value most about our value prop? Is it the ability to get more eyes on their content across platforms? Is it the idea of owning their audience? Is it being able to monetize their content? To figure it all out, I reached out to my early beta users and asked them directly: “What feature would you pay double for if we took it away tomorrow?” Their answers were eye-opening.
Turns out, creators loved our little analytics dashboard—the ability to see exactly where their content was resonating across platforms—and they were willing to pay more for advanced insights like predictive analytics or audience segmentation tools. That feedback led me to consider offering a premium tier with enhanced analytics as part of the package.
Question 2: How Could You Implement Dynamic or Behavioral Pricing Without Alienating Your Base? Dynamic pricing feels risky at first—it’s easy to come across as greedy if prices fluctuate too much or they fluctuate without clear justification. So I decided on a hybrid approach for now: keep the base product affordable (or even free) but offer premium features as add-ons. For instance, creators can use superserious for free to distribute content, but if they want to charge for it (dot dot dot) or if they need advanced analytics and integrations with third-party tools (dot dot dot).. that would be a part of a paid tier.
Transparency is so important here—I make sure every user knows exactly what they’re paying for and we have to agree on why it adds value. No hidden fees, no surprises—just clear communication about what each tier includes and how it benefits them.
Today’s process validated something I’ve learned again and again: pricing is about signaling value. When it’s done thoughtfully, pricing becomes part of your brand story—a way of saying, “This is worth it because you’re worth it.”
Prompt #1 - Monetization and Pricing
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Prompt #1 - Monetization and Pricing ○
Today, you’ll design a pricing strategy that reflects the true value of your hustle-so you can get paid what you’re worth, attract your ideal customers, and avoid rookie mistakes like undercharging or overcomplicating your offers. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in pricing, behavioral economics, and value creation:
- **Professor Sunil Gupta, Harvard Business School:** Expert in pricing strategy and digital monetization.
- **Professor Eric J. Johnson, Columbia Business School:** Authority on behavioral economics and how pricing influences customer decisions.
- **Professor Jill Avery, Harvard Business School:** Specialist in value-based marketing and customer perception.
**What Today’s Coaching Will Help You With:**
You’ll learn how to set prices that reflect your value, test what the market will bear, and use behavioral economics to nudge customers toward your best offers-without racing to the bottom or leaving money on the table.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What is your current pricing model (or what are you considering)?**
- Is it a one-time fee, subscription, tiered package, pay-what-you-want, or something else?
2. **How did you decide on your price?**
- Did you use competitor research, cost-plus, value-based, or just a gut feeling?
3. **What’s one thing that makes your offer more valuable than the competition?**
- Think about unique features, customer experience, results, or guarantees.
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### Step 2: MBA Skill – Value-Based Pricing & Behavioral Nudges
Today’s MBA lesson is about value-based pricing and the psychology of pricing:
- **Value-Based Pricing:**
Set your price based on the benefit your customer receives-not just your costs or what others charge. Ask yourself: “How much is this solution worth to my ideal customer, and what would they pay to solve this pain?”
- **Behavioral Nudges:**
Use simple psychology to encourage action:
- **Anchoring:** Show your best offer next to a higher-priced option to make it look like a deal.
- **Decoy Effect:** Add a “middle” option that nudges customers to choose your preferred package.
- **Urgency/Scarcity:** Offer limited-time pricing or bonuses to encourage faster decisions (but only if genuine).
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### Step 3: Coaching & Pricing Strategy
After you reply, I will use the writings of Professors Gupta, Johnson, and Avery to:
- Help you refine your pricing model and test for market fit.
- Guide you in communicating value so customers see your offer as a no-brainer.
- Suggest behavioral nudges to increase conversions without feeling pushy.
- Offer examples of real businesses who used pricing strategy to grow faster and more profitably.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft pricing idea.
- I’ll help you sharpen your pricing, communicate your value, and suggest next steps for testing and optimizing.
- Remember: The right price isn’t just a number-it’s a story about your value and a signal to your best customers.
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Ready? Share your answers and pricing approach below. Let’s hustle smarter, one lunch break at a time!
Secret Dessert Course
Even though today’s main AI coaching session was about how to move beyond “charging what everyone else charges” and how to implement value-based pricing, it’s never a bad idea to know what everyone else is charging.
The prompt below helps you conduct a “Competitor Pricing Audit” by bringing together two important skills we’ve learned in the first two weeks: Porter’s Five Forces and value-based pricing frameworks. The exercise takes a close look at how your top competitors price similar products or services.
It’s yet another data point in helping you figure out how you can stand out, where you might be leaving money on the table, and what customers are already used to paying.
This isn’t about starting a race to the bottom; it’s about understanding the market so you can confidently position your offer, justify your value, and avoid noob mistakes like underpricing or overcharging.
Plus– if it goes well, you’ll get cool ideas for packaging, discounts, or premium options that can make your business more profitable from day one.
Just copy and paste this next prompt into your favorite AI assistant to enjoy Day 22’s dessert.
Prompt #2 - Audit Competitor Pricing
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Prompt #2 - Audit Competitor Pricing ○
**Today’s Focus: Competitor Pricing Audit – Ivy League MBA Exercise**
*Uncover pricing opportunities and avoid costly mistakes by analyzing your competitors’ strategies.*
**Coached by real Ivy League faculty:**
- **Professor Sunil Gupta, Harvard Business School:** Leading expert in pricing strategy and digital monetization.
- **Professor Eric J. Johnson, Columbia Business School:** Authority on behavioral economics and how pricing influences consumer decisions.
- **Professor Michael E. Porter, Harvard Business School:** Pioneer of competitive strategy frameworks.
**What Today’s Coaching Will Help You With:**
You’ll learn to dissect competitors’ pricing models, identify gaps in the market, and position your offer to maximize value and profitability-without racing to the bottom.
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### Step 1: Reflection Questions
**Answer these in a few sentences each:**
1. List 3–5 competitors offering similar products/services to your target audience.
2. What pricing models do they use (e.g., subscription, one-time fee, freemium, tiered plans)?
3. What unique features or benefits do they highlight to justify their prices?
4. Where does your offer differ most from theirs (quality, convenience, customization, etc.)?
5. (Optional) What type of business are you building (industry, product/service, target customer)?
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### Step 2: Coaching & Pricing Strategy
After you reply, I will use the writings of Professors Gupta, Johnson, and Porter to:
1. **Analyze Competitor Pricing:** Map their pricing against their value propositions and customer segments.
2. **Identify Gaps:** Highlight underserved price points, overpriced features, or unmet customer willingness-to-pay.
3. **Recommend Pricing Models:** Suggest optimizations (e.g., bundling, premium tiers, pay-as-you-go) based on behavioral economics and market demand.
4. **Avoid Common Traps:** Warn against underpricing (commoditization) or overpricing (value mismatch).
5. **Offer Packaging Ideas:** Propose strategies like limited-time discounts, loyalty programs, or “good/better/best” tiers to increase perceived value.
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**Coach verification:**
**All coaches listed above are real Ivy League faculty, and guidance aligns with their published research on pricing and competitive strategy.**
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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 pricing audit and actionable recommendations.
- You’ll leave with a clear roadmap to price confidently, differentiate your offer, and maximize profitability.