Day 17 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: Feed the Hunger. Endlessly.
Curiosity opens doors. But you still have to abide by vampire rules. You can’t just walk into someone’s house. You need to be invited in.
Welcome to week 3– sales week– day 17 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Over the last couple of days we explored the first two skills that’ll help you adopt the trust builder mindset. On Monday it was deliberate empathy. Yesterday it was active listening. Today we’re talking about the third skill you’re going to master: relentless curiosity.
Buuuuut…. Like every day this week, we're going off format before we talk about how to sell. Because before we jump into the mechanics of a curiosity, we should reinforce what it really means to have your content working for you-- sending you people to talk to, people you can help, people to be curious about and with.
If your content isn’t sparking real curiosity—both in you and your audience—then you’re not ready for this week's lessons-- the sales conversations. The best sales, especially in 2025, start with content that invites engagement... questions. Content that’s too polished, too “final,” or too self-focused-- more about you or your product than about the hero (your customer)... well, that content doesn’t give your audience a reason to lean in and ask for more.
So, let’s get practical... before we talk about sales. If you want your content to set the stage for real, trust-building conversations, it needs to open doors for conversation— it needs to get you an invite in.... to make your audience curious enough about what you have to say next... and to make you genuinely curious about what they think, what they feel, what they need.
Just like yesterday-- before we talk about talking-- let's do three exercises to help you get your content right.. to stretch before you run. The good news is these exercises build on everything we’ve said is important from a trust-building mindset perspective so far— empathy, active listening, and later today curiosity.
Exercise 1: What I call The Curiosity Gap Challenge.
- Review your last three social posts or pieces of content and for each, ask: Did I leave a “curiosity gap”— a question unanswered, a story unfinished, a problem unsolved? Or did I try to tie everything up with a neat bow? I confess I do that myself. I'm still learning too.
- If you realize that you are too... Rewrite one of those posts to intentionally leave a question open or some kind of hint at a future reveal. For example, and this is completely true-- everyday I've shot a post since the beginning of this series, I've recorded something that I've intentionally edited out and will reveal next Tuesday. I kid you not. Your version for this exercise does not have to be that elaborate. For you it can be like “I just tried this new strategy last week. Here’s what happened. Want to know the twist? DM me and I’ll share the full story.”
- Do that and then track the engagement on the revised post. Did more people comment, DM, or ask about the rest of the story?
Exercise 2: The “What If” Experiment
- Pick a topic related to your hustle that you haven’t covered yet and create a short post or video that starts with, “What if we tried [something new, something unexpected, something a little risky]?”
- Don’t answer the “what if” in the post. Instead, invite your audience to share their thoughts, their predictions, their experiences.
- Use the responses to fuel your next piece of content. Think of it as co-creating with your audience.
Third exercise: What I call the Assumption Flip
- Identify one assumption you’ve made about your audience—something you’ve always taken for granted.
- Create a poll or a question in your next post that directly challenges that assumption. For example, “I always thought my audience cared most about price. Do you? Or is there something else that matters more to you?”
- Use the results to guide your next piece of content... and to guide your next product decision.
You shouldn’t skip these exercises. They matter. Because today’s sales skill– curiosity– is about creating space for your audience to help them answer their questions. When your content leaves room for curiosity, it invites your audience to lean in, to share, and to trust you with their own questions and concerns. That’s sales before sales– curiosity before curiosity– trust-building before… you get the point.
So let’s get back to our usual format and dive deeper into the trust builder mindset. Today’s focus: curiosity. It opens doors. And it eventually helps get you the invite in.
And when curiosity opens the door, it's trust that walks into that house. If empathy– deliberate empathy– is about giving a damn, and active listening is about shutting the fuck up, then relentless curiosity is about feeding your insatiable hunger for the details.
The best founders are the best salespeople and they are relentless question-askers, always digging for the “why” beneath the “what,” the tension beneath the surface, the story under the story.
And that should explain today’s two questions.
1. What’s one area of your client’s business, life, or challenge you’re genuinely curious about but haven’t explored yet? The answer matters– or better said, the process to get to the answer matters because most people stop at the obvious. Most people miss the real breakthroughs—the moments that build trust and spark opportunity—that come from asking about the things everyone else ignores. When you show relentless curiosity about a client’s world, you signal respect, humility, and a willingness to learn.
Question 2. How can you frame your relentless curiosity as a way to add value? The answer to this one matters because there’s a thin line between feeling like a salesperson is interested in helping you… and… feeling interrogated. On the flip side, you can understand that the best questions are motivated by a desire to help and still get that thin line wrong.
I’ll give you two single-word steers here. One: patience. Two: practice. If it's worth doing, it's worth doing poorly. Just make sure that your relentless curiosity is anchored in service—“How can I help you solve a problem you care about?” You’ll still get it wrong at first. You’ll keep crossing the interrogation line so your only saving grace will be knowing that your goal is service.
Ok. Take a moment and try to answer the Day 17 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: 💼 Exercise a Growth Mindset: Today's Ivy League MBA Skill
Day 17, Part 2 of Lunch Break Millionaire– where we turn whatever you’re eating for lunch into an Ivy League MBA degree. For today’s lunch— we’re jumping back to Day 1’s choice– every big city’s answer to curiosity– the overpriced salad… which can be eaten two ways: mindlessly with a shovel or deliberately, where you explore each ingredient and each combination of ingredients. I’m a shovel guy by the way. Not going to pretend otherwise. My wife says I eat like a child… like I’m the one getting pelted by croutons.
Anywho…. Our lunch choice today is appropriately metaphorical because our MBA lesson today is leadership’s overpriced salad: what I call a curiosity-driven mindset but what every top MBA program– Harvard, Wharton, Columbia– they call it by another name– a growth mindset. And like salad, everyone in HR believes it's good for you… and in my experience, it’s exactly like chess: easy to learn, hard to explain… nearly impossible to master.
So… let’s get into it. How do the Ivy Leagues teach a growth mindset?
Well, they teach you how to:
1) Ask better questions. MBA programs teach students to move beyond “yes/no” or surface-level questions. Instead, they encourage open-ended, exploratory questions like:
- “What’s the biggest challenge you’re facing right now?”
- “If you could wave a magic wand and fix one thing, what would it be?”
- “What’s a risk you wish you could take, but haven’t yet?”
What else? They teach you how to:
2) Challenge assumptions. Students are taught to question the status quo. They’re taught to ask why things are done a certain way, what rules are sacred, and what opportunities might be hiding in plain sight. This habit of “constructive poking” is what leads to trust-building.
What else? They teach you how to:
3) Frame your relentless curiosity as service. The best students learn to use relentless curiosity to both gather data and to show they care. Questions are positioned as a way to help the other person think differently, solve problems… to grow.
One more how… They teach you how to:
4) Practice “curiosity loops”: In classroom discussions and client projects, students are encouraged to keep asking “why” and “what if” until they reach the root cause or a breakthrough insight. Asking why a billion times is annoying but it uncovers a ton of hidden crap you wouldn’t normally uncover.
And all of this– relentless curiosity– this growth mindset– builds trust because:
- It signals humility: You don’t assume you have all the answers.
- It uncovers hidden needs and opportunities.
- It demonstrates investment in the other person’s success.
- It makes the conversation feel collaborative rather than transactional.
Ok. Curiosity helps turn questions into action. If you’ve had prospects reach out to you, especially as a result of your social media or content (from last week), use your curiosity to deepen those relationships. Invite them to a Zoom or call to learn more about their challenges and goals. These warm conversations, rooted in genuine interest, are the best way to build trust and uncover real sales opportunities.
If you’re not seeing many people reaching out, let curiosity guide you back to your Week 1 and Week 2 work. Ask yourself what needs refining in your value proposition, messaging, or content to attract more interest. Trust is built when people come to you because they see real value, not when you chase them down.
That’s it. Hustle smarter.
Part 3: Curiosity in My Hustle: The 28-Day Case Study
My first memory as a stand up comic was when I was in the third grade. We were all eating lunch in class at our desks and it got a little loud for our teacher. So she turned off the lights. That was her cue for “everyone quiet down.” It got completely silent in the room. And she said “Is that better?”
And I said– out loud– it’s making my milk warm. Not particularly clever but it killed.
Great for the 3rd grade and I couldn’t articulate it back then but…
That’s the secret behind great comedy: Say what everyone else is thinking out loud.
This is Day 17, 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. In my current hustle— I’m building tools for creators who want to own their platforms—and relentless curiosity is my most valuable skill. Here’s how I use it to answer today’s questions and build trust:
1. What’s one area of your client’s business, life, or challenge you’re genuinely curious about but haven’t explored yet? Great question.
Recently, I realized I’d never asked creators what their “dream” audience engagement would
look like if there were no algorithms, no restrictions. So I started asking, “If you could design the perfect way to connect with your followers, what would it be?” The answers surprised the hell out of me: some wanted more direct feedback, others wanted ways to collaborate with fans, and a few just wanted to know their audience better. That sounds obvious but the obvious has a way of staying unnoticed until someone says it out loud. That’s the secret behind great comedy: Say what everyone else is thinking out loud.
Question 2. How do I frame relentless curiosity as value?
Instead of grilling creators about their pain points, I approach every conversation with, “I’m genuinely curious about what would make your creative life easier or more fun. If you could wave a magic wand, what would you change?” This framing turns the conversation into a co-creation session, not an interrogation. It builds trust because it’s clear I’m there to learn and help.
How do I use today’s MBA Skill?
- I ask open-ended questions and keep digging until I hit something that makes the other person pause and say, “No one’s ever asked me that before.”
- I challenge assumptions—mine and theirs—about what’s possible.
- I use what I learn to shape my product, messaging, and outreach.
- And I always follow up with, “What else should I be asking you?”—because the best insights often come last.
The Result?
By making relentless curiosity my default mode, I’ve built deeper relationships, uncovered new product ideas, and earned the trust of creators who are tired of being “sold to.” Relentless curiosity isn’t just a tactic—it’s my competitive edge, and it can be yours too.
My key takeaway from today’s exercise? Curiosity—when practiced relentlessly with humility… with intention… and with a service mindset—is the ultimate trust-builder. The more questions you ask, the more doors you open… the more invites in you get.
So… be a good vampire… a well-informed vampire… Feed the hunger(!!!) your curiosity... endlessly.
Prompt #1 - Curiosity
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Prompt #1 - Curiosity ○
Today, you’ll learn how curiosity—the genuine desire to understand your customers’ needs, challenges, and aspirations—can become your most powerful tool for building trust and lasting relationships. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in customer engagement, business psychology, and relationship-building:
- **Professor Francesca Gino, Harvard Business School:** Expert in curiosity, decision-making, and the power of asking better questions.
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and learning cultures.
- **Professor Adam Grant, The Wharton School, University of Pennsylvania:** Specialist in reciprocity, authentic connection, and the science of motivation.
**What Today’s Coaching Will Help You With:**
You’ll practice leading with curiosity instead of assumptions, learn how to ask questions that deepen understanding, and discover how curiosity can help you uncover hidden needs—so your hustle becomes a place where customers feel truly heard and valued.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **When was the last time you approached a customer conversation with no agenda—just a desire to learn? What did you discover?**
- Think about what happened when you focused on understanding, not pitching.
2. **What’s one assumption you often make about your customers that might be worth questioning?**
- Consider if there’s a belief or stereotype you bring to conversations that could be limiting your understanding.
3. **What’s one open-ended question you could ask your customers this week to uncover a new insight or need?**
- Brainstorm a question that invites them to share more about their challenges, goals, or frustrations.
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### Step 2: MBA Skill – Curious Inquiry
Today’s MBA lesson is about the art and science of curious inquiry:
- **Lead with Curiosity:** Begin every customer interaction by asking yourself, “What can I learn here?” instead of “What can I sell here?”
- **Ask Open-Ended Questions:** Use questions that can’t be answered with a simple yes or no. For example: “What’s the biggest challenge you’re facing right now?” or “What would make your life easier this week?”
- **Listen for the Unspoken:** Pay attention to what’s not said—emotions, hesitations, or topics they avoid. These often reveal the real needs behind the words.
- **Challenge Your Assumptions:** Notice when you’re filling in the blanks for your customers. Pause and ask, “Is this really what they mean, or am I projecting my own ideas?”
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### Step 3: Coaching & Curiosity Action Plan
After you reply, I will use the writings of Professors Gino, Edmondson, and Grant to:
- Help you identify opportunities to bring more curiosity into your customer conversations.
- Guide you in crafting open-ended questions that invite deeper dialogue and trust.
- Suggest ways to challenge your assumptions and uncover hidden customer needs.
- Offer examples of businesses that have built loyal followings by making curiosity a core part of their culture.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft open-ended question.
- I’ll help you refine your approach, suggest new ways to practice curiosity, and offer next steps for making genuine inquiry a signature strength in your hustle.
- Remember: Curiosity isn’t just a sales tactic—it’s the foundation of trust, innovation, and real growth.
Secret Dessert Course
Curiosity means turning every answer into a new question. In business, the most valuable feedback is the insight that makes you pause, tilt your head, and wonder what you’re missing. Today’s dessert course is for the founders who know that feedback is only as valuable as the curiosity you bring to it. This prompt will help you set up a curiosity-driven feedback loop: a way to collect, analyze, and—most importantly—question every nugget of input from customers, teammates, and partners. Use it with Day 15’s steer: daily journaling!
Prompt #2 - Loop the Gift that is Feedback
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Prompt #2 - Loop the Gift that is Feedback ○
**Today’s Focus: Curiosity-Based Feedback Loop**
**Ivy League MBA Coaching by:**
- **Professor Francesca Gino, Harvard Business School:** Expert in curiosity, decision-making, and learning from feedback.
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and team learning.
- **Professor Alison Wood Brooks, Harvard Business School:** Specialist in anxiety reappraisal and turning feedback into fuel for growth.
**What This Prompt Will Help You With:**
You’ll design a feedback loop that doesn’t just collect opinions, but actively seeks out the questions and surprises hidden in every response. This approach will help you uncover blind spots, spark innovation, and build a culture where curiosity is your most valuable currency.
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### Step 1: Set Up Your Feedback Loop
**Instructions:**
Identify one recent source of feedback—customer reviews, team check-ins, or partner calls—and collect the raw notes or transcripts.
**Reflection Questions:**
1. **What were the main points or suggestions in the feedback?**
2. **Did anything surprise you or contradict your expectations?**
- (If so, what? If not, why not?)
3. **What assumptions did you have before reading or hearing the feedback?**
4. **What new questions does the feedback raise about your business, team, or customers?**
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### Step 2: Analyze with Curiosity
**Curiosity-Driven Feedback Analysis:**
For each piece of feedback, ask:
- **What’s the underlying need or emotion behind this comment?**
- **What does this feedback suggest about our blind spots or opportunities?**
- **What would happen if we explored the opposite of what the feedback suggests?**
- **What’s one small experiment we could run to test a new idea inspired by this feedback?**
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### Step 3: Create a Curiosity Action Plan
**Action Steps:**
1. **List the top three new questions or hypotheses that emerged from the feedback.**
2. **For each, design a tiny experiment or next step to explore further.**
- (Example: “If feedback says customers want faster support, try a 24-hour response window for one week and track results.”)
3. **Share your findings and new questions with your team or a trusted advisor.**
- Ask: “What else should we be curious about here?”
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### Step 4: Coaching & Insights
**After you complete the above, reflect:**
- **What did you learn about your own assumptions or biases?**
- **How can you make curiosity a regular part of your feedback process?**
- **What’s one habit you’ll build to keep asking ‘what if?’ and ‘why not?’**
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**How to use this prompt:**
Copy and paste these steps into your favorite journal or AI assistant. Apply them to your next round of feedback—whether it’s from customers, teammates, or partners.