Day 18 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: Show Your Receipts. Unapologetically.
The luxury goods market has never been about higher quality goods. Better service– definitely. But higher quality… meh. The luxury goods market has always been 100% about signaling one’s wealth and status. People basically saying “Look, I’m wearing the same quality product as you but I have the flex to pay for the really expensive Italian tag that’s sewn into my clearly-Chinese-made product.”
The one upside to all the tariffs nonsense is that we crossed a bright beautiful red line when Chinese manufacturers stepped out of the shadows in the luxury goods market. Because the entire luxury market– like the bond markets of old… like the entire US healthcare system– is built on the least trustworthy pricing model out there: opaque pricing based on artificial scarcity… or in plain English: Snake-Oil-level inflated margins… shady, deceptive elegance… scammy, overpriced sophistication… exclusive, limited-edition late stage capitalism.
[Chef’s kiss]
Welcome to week 3– sales week– day 18 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. And today’s topic: the fourth skill of the trust builder mindset: transparency.
Buuuuut…. Like every day this week, we're going off format before we talk about how to sell. Before we jump into the mindset of radical transparency-- before we talk about owning your process, sharing your wins and losses, before we talk about you “showing your receipts” to your client. Before all that... let’s talk about what it actually means to get your content right… before you ever pitch a single sale. Because if your content isn’t built on honesty and openness from the start, your sales conversations will always feel forced. In 2025, people don’t buy products or services. They buy trust. And trust is built out in the open.
So, how do you make sure your content is ready for real sales conversations? Yes, you should be posting regularly. And yes, you should be following the content calendar we built last week. And… you should be making sure every piece of content—every post, every story, every video—reflects who you are and what you stand for. Hopefully, framing your client as the hero of that story. Yes– given our theme later today– your content IS about making your process visible, your thinking transparent, your values unmistakable.
So like every other day this week… our content has to be what we’re going to be when it turns into an actual conversation with someone who watched it. Our content has to be empathetic before we are, it has to listen before we do, it has to be curious before we are… and today, it has to be transparent before we are.
So… Here are 3 exercises to help you get your content right before you move to sales conversations. All 3 exercises build on everything we’ve learned so far—empathy, active listening, curiosity—but they hopefully push you to be even more open and authentic.
Exercise 1: What I call The Receipts Audit.
- Review your last five pieces of content and for each one, ask:
- Did I show my work? Did I reveal any part of my process—success, failure, or uncertainty?
- Did I explain why I made a certain decision or tried a certain approach?
- Did I invite my audience to see behind the curtain, or did I only show the polished result?
- Pick one post and rewrite it to include a “receipt”—a screenshot, a note, a reflection, a lesson learned from your process.
- And then track engagement on the revised post. Did people comment? Did they DM? Did they ask questions about your process? Did it spark a different kind of conversation?
Exercise 2: The “Why Not?” Experiment.
- Take a topic or decision you’ve been avoiding in your content—something you’re afraid to talk about because it’s messy, controversial, just plain uncomfortable… and create a short post where you explain why you’re not doing that thing, or why you’re hesitant to try it.
- Invite your audience to help you… to share their own experiences… to give you some earnest advice.
- And then use the responses to guide your next steps– content wise, product-wise, process-wise. And then the cherry on top: consider sharing what you learn in a follow-up post. Shampoo. Rinse. Repeat.
Exercise 3: What I call The Transparency Timeline.
- Create a simple timeline of your side hustle journey so far. Mark key moments—decisions, pivots, wins, mistakes—and write a sentence or two about each. Don’t use AI. Be authentic. Reflect on how it feels. Or if you can’t help yourself and you use AI, ask it to be authentic and to guess at how it feels.
- And then share your timeline in a post. Invite your audience to share their own milestones. Am I doing that? Yes. Can you do that too? Absolutely. Be a great artist. Steal.
These kinds of exercises matter because transparency– our sales training for today.. Our trust-builder mindset training– is about making your audience feel like they’re part of your journey. When your content invites people in—when it shows your receipts, your failures, your doubts, and your wins—you’re building a foundation of trust that makes every sales conversation easier. You’re inviting people to join a story they believe in.
Ok… let’s get back to our usual format and dig deeper into the trust builder mindset. But remember: one of the most powerful sales tools you have is your willingness to be open, to show your work, to invite your audience along for the ride.
Ok. Let’s get back on track.
In a world where every twelve year old is more sophisticated than the marketing that easily scams their Nana and PopPop, the healthiest– and tragically, the least common way to stand out as a founder, as a salesperson, as an operating model– is to show your receipts—openly, unapologetically, and before anyone asks. Transparency.
That’s probably my least popular opinion when it comes to sales. I am 100% convinced that the best way to handle your client-cost discussions: unflinching transparency. Don’t hide the messy parts of your process; invite the client to look behind the curtain and see exactly how things work, exactly how much it costs you to offer your product or service; and how much you need to make for the hustle to be worth your time. The clients you want will respect that.
So today’s questions are:
1. Where in your sales process are you tempted to overpromise, hide a limitation, or gloss over the messy details? This question matters because– and I risk sounding like a total boomer– trust is built on honesty. The urge to hide flaws or exaggerate capabilities is natural, but it’s also the fastest way to erode credibility.
When you’re transparent about what you can and can’t do, you’ve already differentiated from 95% of salespeople. Because 95% of salespeople keep selling features their company doesn’t have. When you’re transparent about what you can and can’t do, you set clear expectations, you reduce anxiety (internally and externally), and you invite your clients to trust you—even when things go sideways.
All the research shows that unflinching transparency is more and more a baseline expectation in every industry. Not a nice-to-have. A baseline expectation. And customers reward it with loyalty and referrals.
Question 2. How can you proactively communicate your strengths and limitations to your next prospect or partner? This one matters because proactive, unflinching transparency has zero to do with damage control. It’s 100% a competitive advantage. By openly sharing how you operate, what you value, and where you draw the line, you differentiate yourself from competitors who hide behind jargon and vague promises. This kind of clarity prevents misunderstandings. And in my experience, it attracts clients who have been burnt in the past… which is about 100% of clients.
Everyone values integrity over the oh-so-common alternative.
Ok. Take a moment and try to answer the Day 18 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: 💼 Go Rogue with Open, Ethical Leadership: Today's Ivy League MBA Skill
There is no Ivy League professor– that I’m aware of– that’s teaching the idea of a mindset rooted in unflinching transparency. Not those two specific words. Those two are mine. In the Ivy League– at places like the Harvard Business School and at Wharton– they call THAT mindset something way more scary. They call it open communication. They call it accountability. And the scariest one of all– they call it ethical leadership– the metaphorical beating heart of the Ivy League’s teachings on leadership and organizational behavior.
So they might not use my words but unflinching transparency is definitely framed as a strategic necessity for building trust, for building resilience, for building long-term business value– and maybe most importantly, for building a business that actively changes the world for the better.
Ok. So how do the Ivy League MBA programs teach their version of what I call unflinching transparency?
- They stress Open Communication. It’s a skill. Students are trained to communicate decisions, risks, and setbacks as openly as they share wins. For you– this means saying what you’ll do, sharing why, and delivering on your word—then explaining candidly (and with kindness) when things don’t go as planned.
- They stress Stakeholder Engagement. Two fancy words that just mean “be honest with your client”... invite their feedback… treat that feedback as a gift… and always, always, always share your reasoning behind decisions, demonstrate that governance isn’t a black box… that it’s open to feedback, open to change.
What else?
- They stress Visible Processes: Whether it’s pricing (which I think we’re going to talk about again next week)... whether its pricing, supply chain, product limitations– the important stuff– MBA students are encouraged to make the “how” as clear as the “what.” It’s a muscle you should flex. Use companies like Buffer and Patagonia as your inspiration and openly share everything– your salaries, your supply chain practices, your mistakes. That’s you setting a new standard for unflinching transparency in business.
Maybe one more?
- Use Transparency Tools. The biggest one right now– I’d argue– is social media. Not sure they’re teaching that level of crazy in the Ivies. But they are teaching the importance– internally– of using dashboards, feedback systems– just regular updates– to make unflinching transparency actionable. These kinds of tools help everyone stay accountable. They ensure that openness is a daily practice.
The whole point here is that unflinching transparency builds trust. Why?
- It reduces information asymmetry– a fancy way of saying that everyone’s looking at the same numbers… which necessarily makes clients feel like partners. What else?
- It mitigates misunderstandings. It accelerates problem resolution.
- It increases loyalty.
- It differentiates you from competitors who want the world to think that their shit doesn’t stink.
Have the tough conversations.
Ok. Transparency is about showing up authentically in your sales process. If you’ve had prospects reach out because of your social media posts or content (from last week), lean into that openness. Invite them to a Zoom or call to discuss how you can help, and be clear about what you offer and what you don’t. This kind of honest, direct approach builds trust. It sets you apart.
If you’re not seeing many people reaching out, let transparency guide you back to your Week 1 and Week 2 work. Ask yourself if your value proposition and problem validation are clear and compelling. Refine your messaging and content until you attract genuine interest. Remember: trust is built when people come to you because they see real value and honesty.
It’s how you hustle smarter.
Part 3: Transparency in My Hustle: The 28-Day Case Study
Here’s my impossible dream for the grandkids I don’t yet have. Some day, we’ll walk into stores that sell anything– groceries, clothes, healthcare, drugs, electronics– and next to each price will be a breakdown of how much that store paid for the product, how much above that is going to pay down that store’s expenses like salaries and rent– and how much profit they expect to make from that specific sale. And you know who’ll look at those tags obsessively? No one. And yet, we’ll all feel a little less like we’re lambs being taken to slaughter. We’ll feel more trusting of that store, of that entire society.
My point is that you don’t need to look at a company’s charitable giving to figure out their values and principles. You don’t need to look at their internal culture. Just look at how transparent they are with their pricing. Because being fair and efficient and accountable and client-obsessed starts with you not treating everyone like they’re mindless consumers– sock puppets.
This is Day 18, 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. Let’s run with an idea that I really believe in: that trust is the foundation of literally everything good in business. If I’m right… When people don’t know how much your product or service really costs you, they can and should assume the worst. Customers should absolutely believe that they’re being ripped off. But if you just lay your cards on the table—show everyone exactly where every dollar goes—suddenly, people start to trust you. They see that you’re not hiding anything, that you’re playing fair; that you expect to make a fair profit for your hard work… which no one who trusts you would begrudge you. In fact, when people trust you, they buy more. They give your missteps the benefit of the doubt. They stick around longer. It’s not rocket science, but somehow, most businesses act like it is.
Ok, let me get off my high horse and share how today’s exercise improved my hustle.
Question 1 was: Where am I tempted to over promise or hide the messy parts?
My answer is that right this second, my company is me. Solo. Want another feature in the mobile app? I can definitely deliver it. But right now, I’m not scalable. And to get scalable, I need to hire more engineers…. Which will raise the price of my services– because they’ll now be “our services.” When I’m talking to creators, it’s tempting to gloss over the limitations of my platform—which are mostly the limitations of being a one-man-show. Would I like more and better integrations with certain social networks? Absolutely. Better analytics? Hell yeah!
A younger me might have waited for someone to ask before admitting these gaps. Now, I lead with them: “Here’s where I’m strong, and here’s what’s still a work in progress. If you need X, I’ll be honest—I’m not there yet, but here’s the roadmap. And I’ll post regularly about progress on that roadmap.”
That’s transparency. It leads to better conversations, more realistic expectations, a few prospects who I’m sure will come back in a couple months… maybe not because they trust my honesty… but because they want to.
Question 2 was: How do I proactively communicate strengths and limitations? You’re kinda watching it. If I hit a snag, you’ll see the video of me– from me– first. That’s the power of the hashtag– BuildInPublic.
This level of openness will turn skeptics into people who root for you, because they know you’re not hiding anything.
It’ll lead to more referrals, as creators tell their peers, “You can trust this guy—he’ll tell you the truth, even when it’s not pretty.”
I’m not sure how you can answer either of today’s questions and not exercise the muscle that is our MBA Skill– ethical leadership. But if you need more a explicit steer for your hustle, here are some suggestion
- Set up regular updates and feedback loops to keep your clients in the loop about progress and setbacks. It’s why God invented social media.
What else?
- Invite clients and potential clients to share their concerns and suggestions. Make them part of your process.
- Celebrate your wins publicly. Just as powerful: share the lessons you’re learning from failures. Reinforce and reinforce and reinforce that unflinching transparency we talked about as your core value.
I think the result of making transparency your default will be deeper relationships, much-much-less churn, and once you have a team– a culture where everyone— employees and partners and clients– feel safe to be honest.
I mean really. When was the last time you heard someone suggest honesty as your strategic differentiator?
My key takeaway for today? You can’t sell without trust. And transparency—when practiced unapologetically and proactively—is the foundation of trust– the absolute fastest way to build loyalty, the absolute best insurance policy against misunderstandings. So…
Show your receipts. Unapologetically.
Prompt #1 - Transparency
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Prompt #1 - Transparency ○
Today, you’ll learn how transparency—being open, honest, and clear about what your business can and can’t do—builds trust, deepens relationships, and sets you apart in a crowded market. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in ethical leadership, trust-building, and authentic communication:
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and creating cultures of openness and learning.
- **Professor Francesca Gino, Harvard Business School:** Expert in behavioral ethics and the power of honest communication.
- **Professor Adam Grant, The Wharton School, University of Pennsylvania:** Specialist in reciprocity, authenticity, and the science of trust.
**What Today’s Coaching Will Help You With:**
You’ll practice being transparent in your customer conversations, learn how to address concerns and limitations head-on, and discover how honesty can turn even challenging moments into opportunities for trust and loyalty.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What is one thing about your product, service, or process that you worry might disappoint a customer?**
- Be honest—think about limitations, risks, or areas where you’re still improving.
2. **How could you proactively address this concern with your customers—before they bring it up or experience it?**
- Consider how you could communicate this openly and constructively.
3. **What’s one way you could turn a moment of transparency into a trust-building opportunity?**
- Think about how you could use honesty to deepen your relationship or offer extra value.
---
### Step 2: MBA Skill – The Power of Transparency
Today’s MBA lesson is about transparency as a trust-building tool:
- **Transparency is not just about sharing information—it’s about being honest about what you know, what you don’t know, and what you’re working to improve.**
- **Addressing concerns proactively:** When you disclose limitations or risks before your customer discovers them, you demonstrate respect and build credibility.
- **Inviting feedback:** Let customers know you welcome their input and are committed to learning and growing together.
- **Turning mistakes into opportunities:** If something goes wrong, own it, explain what happened, and share how you’re fixing it—this builds trust faster than perfection ever could.
---
### Step 3: Coaching & Transparency Action Plan
After you reply, I will use the writings of Professors Edmondson, Gino, and Grant to:
- Help you identify the most important areas for transparency in your business.
- Guide you in crafting messages that address concerns honestly and constructively.
- Suggest ways to turn moments of vulnerability or limitation into trust-building conversations.
- Offer examples of businesses that have built loyal followings by leading with transparency and authenticity.
---
**How to use this prompt:**
- Respond with your answers to the reflection questions and your ideas for transparent communication.
- I’ll help you refine your approach, suggest next steps, and offer strategies for making transparency a signature strength in your hustle.
- Remember: Trust is built when people know you’re being real with them—even when it’s not easy.
Secret Dessert Course
Transparency is about what you explain before they even ask. In business, nothing sows the seeds of doubt faster than murky pricing or hidden fees. It’s so important that we’ll be revisiting how to price early next week. But in the meantime…today’s dessert course is your chance to shine a light on the numbers. This prompt will help you craft a pricing story that “shows your receipts” and explains the value behind every dollar. Because– in my experience– when customers see the math, the logic, the heart behind your prices, they trust you more. Leave your calculator at home. What you need for this exercise is courage. Let’s make your pricing as clear as your mission.
Prompt #2 - Share the Prices Behind Your Prices
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Prompt #2 - Share the Prices Behind Your Prices ○
**Today’s Focus: Transparency in Pricing**
**Ivy League MBA Coaching by:**
- **Professor Sunil Gupta, Harvard Business School:** Expert in pricing strategy and value creation.
- **Professor Leslie John, Harvard Business School:** Authority on transparency, nudges, and consumer trust.
- **Professor Michael Luca, Harvard Business School:** Specialist in behavioral economics and digital transparency.
**What This Prompt Will Help You With:**
You’ll learn how to make your pricing structure transparent, articulate the value behind your prices, and build trust with customers by showing—not just telling—why your hustle is worth every cent.
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### Step 1: Pricing Audit
**Instructions:**
Review your current pricing structure (or draft your first one if you’re just starting out).
**Reflection Questions:**
1. **What are you charging, and why?**
- List your prices and the reasoning behind them (e.g., cost, market rates, value delivered).
2. **Are there any hidden fees, add-ons, or unclear charges?**
- If so, how can you make them more visible and understandable?
3. **How do your prices compare to competitors?**
- Are you charging more or less, and what justifies the difference?
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### Step 2: Value Storytelling
**Transparency Exercise:**
Write a short explanation (2–3 sentences) for each product or service that answers:
- **What does the customer get for this price?**
- **Why is this price fair or better than alternatives?**
- **How does this price reflect your values or mission (e.g., sustainability, quality, local sourcing)?**
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### Step 3: Customer Communication
**Prompt:**
Draft a pricing FAQ or a pricing page section that includes:
- **Clear breakdown of what’s included**
- **Any optional extras and their costs**
- **A brief story about why you set prices the way you do**
- **An invitation for questions or feedback**
**Example:**
> “Our $99/month plan includes unlimited access to our core features, 24/7 support, and regular updates. We charge less than competitors because we believe in making powerful tools accessible to everyone, and we keep costs low by staying lean and focused. If you have questions or suggestions about our pricing, we’d love to hear from you!”
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### Step 4: Coaching & Insights
**After completing the above, reflect:**
- **What surprised you about your own pricing decisions?**
- **How can you make your pricing even more transparent and customer-friendly?**
- **What’s one habit you’ll adopt to keep your pricing honest and open as your business grows?**
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**How to use this prompt:**
Copy and paste these steps into your favorite journal or AI assistant. Use them to audit your pricing, tell your value story, and communicate clearly with your customers.