Day 15 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: Give a Shit. Seriously.
Welcome to week 3, day 15 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Last week we started to earn the attention of our potential customers. This week, it's about getting their permission to help with something they care about– a job they need to get done (Day 2’s MBA skill).
OK. Day 1 of sales week. I’m going to go off-format just a bit everyday this week. Because a lot of first-time entrepreneurs think that their product or service will magically sell itself. It will not. You’re either going to sell it or it's not going to get sold. The only good news is that in 2025, selling is no longer about cold calling or spammy email campaigns. That’s partly why last week our focus was on building a social media presence and planning out your content strategy– your sales funnel.
So– while we’re going to talk this week about how to engage a prospective client– not “how to talk to them”-- how to listen, how to empathize, how to lead with curiosity and transparency– while we’re going to talk about all that– we need last week’s exercises to start landing prospective clients into your DMs. As I just said, you should NOT be cold calling. You should not be setting up stupid little automated email campaigns. We’re spending the entire day this coming Friday talking about cold calling and email campaigns and the tentative title of that session is Trust Killers. Stay the hell away from those practices.
So yeah, let’s talk about selling today but if your socials– your content… based on your content pillars (from last week)... if they aren’t generating interest… positive comments, DMs… go back and revisit last week’s exercises. If you think your pillars are right, make more content and keep making it until there’s interest. And then… keep making more after that. If you need to rethink your content pillars, that’s fine. Rethink it. Make new, different content. And keep making more of it.
I’m not going to leave you hanging on this one. Here’s a simple exercise to extend the work you did last week.
First, pick one of your content pillars and craft a post that’s not about you—make it about your audience. Make them the hero. Ask a question that gets at a real frustration or desire your ideal customer has, or share a quick tip that solves a tiny but painful problem. The goal is to spark conversation. Use a clear, compelling image or a short video, and end with a simple call to action like “Drop a comment if you’ve ever felt this way” or “DM me if you want to work together.”
Just keep telling yourself that the audience is the hero. Helping them is your why. If you do that– if you spotlight your audience’s needs and invite them to engage– you’re going to help turn passive scrollers into people you can talk to in real life.
Second, once you post, don’t ghost the comments. Please. Go through any of my old content. I wasn’t selling anything. I was just genuinely grateful that people would take the time to comment. Reply to every single one of your comments—even if it’s just a quick “thanks for sharing” or “great point.” If someone DMs you, keep the conversation going by asking a follow-up question about their challenge or what they’d love to see next.
This back-and-forth builds trust– what we’re going to talk about all week– and it signals to the algos (our enemy) that your content is worth showing to more people. Remember: social media is a relationship engine. The more genuine the conversations you spark, the more interest you’ll land—and the more people will start to see you as the go-to solution for their needs.
Ok. Back to our usual format. If you’re like me, you’ve always felt awkward… anxious about “selling” so today– and this whole week– we’re diving into the deep end of the discomfort pool… with zero risk of drowning because we’re going to learn and practice what I call the trust builder mindset. It has 4 components and we’ll devote one day to each– empathy, listening, curiosity, and transparency. And then on Saturday, we’ll talk about some trust multipliers.
Quick disclaimer. This week is going to focus on b2b– business to business– sales– because that’s been my experience of the last 25 years– on both sides of the fence– buyer and seller. But the underlying framework for improving your sales skills should help you with any kind of hustle… including your day job. Why? Because we’re going to define sales as the ability to create and sustain trust at every stage of your buyer’s journey… whether that buyer is a complete stranger or they’re your boss or stakeholder at work.
So sales is really about some human being trusting you. I frame it that way because in the b2b world, you never really sell to some big complex faceless corporate customer. You never really sell to some super senior manager who all the sales literature says you need to “align”... which is corporate speak for making sure you get “the executives to pretend they agree with each other long enough to stop arguing and make a decision—or at least to nod along while someone else makes it for them.” Because that’s not an external salesperson’s job.
You sell to some real human being– 6 levels down from the C-Suite– some person with a real job and a real job to be done. And that buyer wants to buy from someone they believe will act in the buyer’s best interests– not simply the best interest of buyer’s company but the best interest of the buyer… the human being… in the best interest of the buyer’s career… the job that helps them support their family, helps them pay their mortgage. The job that they wish would become a more senior job, a higher-status, better paying role…. If they could just get their job done.
So the stakes around selling them are really high. Trust in that context isn’t given— and I know this sounds cliche but… it’s earned through four deeply interrelated (learn-able) skills– what I said two seconds ago: empathy, listening, curiosity, and transparency– what I call the trust-builder mindset.
Ok. Here are today’s two questions and the first one involves a little role play (potentially). Over the last two weeks you’ve hopefully been talking to some potential customers. Think about your last significant conversation with a potential customer.
Question 1 is: What’s one thing they said—or didn’t say—that revealed a deeper need or concern? The answer matters because most of us listen for what we want to hear, or for cues that let us jump back into our pitch. But the real gold—the trust you want to build—comes from noticing what’s hiding just beneath the surface. Maybe it’s a hesitation, a sideways comment about “budget season,”... a casual mention of a competitor. Whatever it is, these signals are your roadmap to building real rapport and…. understanding what your customer truly values.
If you can’t recall a recent conversation with that level of detail– buy yourself an AI notetaker… and for now… imagine your next one: what would you listen for… that would help you see the world through their eyes?
Question 2– If you had to choose one question to ask your next prospect that would help you uncover their biggest challenge, what would it be? This question– and your process for answering it– matters because the best salespeople aren’t the ones with the slickest pitch—they’re the ones who ask the right questions and then shut the hell up.
This question second forces you to get specific and intentional about how you’ll build trust. It’s not about trapping them with a “gotcha,” but about opening a door that will let them share what’s really on their mind– what jobs they have that need to get done– again harkening back to day 2. And yes I used the verb harkening…. It was me, not an AI. Anywho, your question– the one you’re thinking about asking your next potential customer– should invite honesty, not defensiveness.
And if you’re not sure, that’s perfect— no one gets it right on their first try. Today’s exercise is exercising the muscle you’ll need– the more you craft questions like today– that feel authentic, that feel helpful, not transactional– the more you’re flexing that muscle.
That muscle is the mindset. Both questions are letting you exercise– or role-play the trust-builder mindset– radical curiosity, active listening, deliberate empathy, unflinching transparency. The habit you’re building is to ask question-after-question, to listen to answer after answer actively and to care deeply about helping that person get their job done.
Ok. Take a moment and try to answer the Day 15 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: 💼 Learn Empathy Mapping: Today's Ivy League MBA Skill
When I took Drivers Ed in high school back in the 80s, you’d never get into an actual car. The PE teacher– it was always the PE teacher– would teach you acronyms to remember when driving. For instance, what to do if you’re driving on the highway, and ahead of you– in the distance– you see a pedestrian-shaped-lump lying on the ground– and again… they’re in your lane.
Well… You BRAKE– the acronym– capital B-R-A-K-E:
Breathe deeply and stay calm.
Review the obstacle and your surroundings.
Assess your options for avoiding the obstacle.
Keep checking blind spots as you signal.
Exit the hazard area safely.
BRAKE. Its acronyms like this explain why so many Gen-Xers landed in prison for manslaughter. They’d be driving 65-70 miles an hour on a highway and see some poor bastard on the ground in their lane in the distance… and they’d try to BRAKE. Ok I see him. Step 1: breathe deeply. Step 2… [thump thump]. They’d never get to step 2.
Day 15, Part 2 of Lunch Break Millionaire– where we turn whatever you’re eating for lunch into an Ivy League MBA degree. Today’s lunch— square frozen pizza, tater tots and chocolate milk: the quintessential 80s school lunch– with your vegetable being ketchup. Thank you President Reagan! And our MBA lesson today: empathy mapping.
Don’t take notes because everything I’m going to tell you… about how to do it… is exactly as useful as Driver’s Ed in the 80s. What do I mean?
Imagine you’re face-to-face with a prospect and you want to sell them your hustle’s product or service. You’ve watched this series and you’re thinking “Trust Builder Mindset. Trust Builder Mindset. Trust Builder Mindset.”
Instead of the BRAKE acronym, you can use the EMPATHY:
Explore emotions: What is the prospect feeling? What emotions drive their decisions?
Map their words: What is the prospect saying? What language do they use to describe their pain?
Probe their thoughts: What is the prospect thinking? What worries or hopes occupy their mind?
Analyze their actions: What is the prospect doing? How do they behave when faced with this problem?
Tailor your approach: How can you adapt your pitch to their emotional, verbal, and behavioral cues?
Hear their feedback: What signals or responses do you get as you engage?
Yield results: How can you close the sale or deepen the relationship, informed by empathy?
EMPATHY. What does that have to do with Driver’s Ed in the 80s? Because you’ll be on that first letter of EMPATHY… explore emotions… What is the prospect feeling? [thump thump]
My point is that empathy– small e empathy– is a skill. And it’s the most important thing you should exercise while you’re sitting there quietly, actively listening to your prospect. And no acronym is going to help you. Because that conversation is driving at 65-70 miles per hour.
Real sales conversations are messy. It’s dynamic. And it never ever fits neatly into an acronym or a workshop or a template. You don’t have the luxury of consulting your notes or taking a quiet moment. You’re empathy mapping in real time—actively listening for what your prospect is saying, yes, but also for what they’re not saying, for the emotions beneath their words, and for the unspoken concerns that might derail a deal if they’re left hanging’.
This is where most non-salespeople get tripped up: they either default back to pitching– the hard sell– or they miss the subtle signals– the cues that reveal their prospect’s true needs.
I didn’t say it was going to be easy. It won’t be. Empathy mapping in the field isn’t about filling out quadrants on a whiteboard. It’s about being present. It’s about being curious. It’s about being disciplined enough to notice patterns, ask insightful follow-ups, and adjust your approach on the fly. If a prospect says, “We’re looking for a more efficient solution,” but their tone is hesitant, your empathy map might flag a hidden concern about implementation risk or change management. Or, if they keep returning to a specific pain point, that’s your cue to dig deeper.
The Ivy League literature is clear: effective empathy mapping requires both structure and flexibility. All that research and all those best practices recommend using interviews, observations, and open-ended questions to gather data—but in a live sales call, you’re synthesizing all of this on the spot. It’s a skill that combines active listening with emotional intelligence, and it’s what separates top performers from the rest. Studies show that sales professionals who can adapt their approach based on real-time customer cues close more deals and build stronger relationships.
So, as you practice empathy mapping today, remember: the real power comes when you move beyond the theory and learn to map in the moment—when you’re not simply following a process– a stupid acronym– but truly engaging with another human being, uncovering their story, and helping them find a solution that matters to them. That’s how you turn EMPATHY from a stupid acronym into your competitive advantage. Practice. Practice. Practice.
Ok. Take a napkin (or your phone’s notes app) and sketch out an empathy map for your ideal customer. What’s keeping them up at night? What’s their job to be done? How can you help them get that job done? You can fill the napkin without having talked to a prospect but it's so much better if you’ve done some listening and learning first.
Also, now that you’re building empathy as a core skill, put it into action with your emerging sales process. If you’ve had people reach out to you through social media or other channels because of your marketing (from last week), don’t let those conversations just sit. Schedule a quick Zoom or call with them—not as a “sales pitch,” but as a genuine chance to listen and learn what they need. This is the kind of warm outreach that builds trust and real relationships, not the cold calls or email blasts that break it.
If you’re not getting many people reaching out, that’s a signal to revisit your Week 1 and Week 2 output—refine your value proposition, problem validation, and messaging until you start seeing real interest. Trust is built when people come to you because they see something valuable.
Part 3: The Thump-Thump in Action: The 28-Day Case Study
This is Day 15, 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.
Okay. Long long looooong before I started building my current hustle—a platform for creators to own their audiences—I hated the idea of “selling.” Still do. It makes me feel dirty. I’d rather write code, design features, brainstorm new ideas– ANYTHING– other than pick up the phone and ask someone to buy my baby.
But here’s what I learned– and it's the simplest truth in modern life– if you don’t sell, you don’t eat. And if you don’t eat, your hustle dies.
Look… I could answer today’s questions for you. Tell you how I use EMPATHY– the acronym or the real thing.
But I’d rather share a small vulnerability.
I was never terrified of rejection. It was the opposite really. I was terrified of what it would say about me if I became a salesman. I was terrified that it would be me compromising my values– the ones that say that money is not what I live for.
I mean I might have been afraid of rejection on some level but not really. I might have been worried that if someone said no, it meant my idea wasn’t good enough… but not really. I probably have thicker skin than you.
I– personally– just hated feeling like a “salesperson”-- a class of people I always connected for myself with manipulation. With materialism. I didn’t want to bother people and I definitely didn’t want to come off as being pushy or desperate or as a raging Capitalist.
My fears– Mr. Selfless Spiritualist– were all about me, not about those who I wanted to serve (if I were being genuinely selfless. My fears were about me, not my customers. Even though it was wrapped in the fancy wrapping paper of spirituality– of selflessness. It was always really about my giant fucking ego, not their needs.
I still hate selling. But I know why I should do it now. On a superficial level it’s because if you don’t sell, you don’t eat. And if you don’t eat, your hustle dies. On a deeper level, it’s because sales– if done correctly– is service. It’s living your values. It’s serving others.
And that’s the best reason for why it's raining money.
Prompt #1 - Empathy
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Prompt #1 - Empathy ○
Today, you’ll learn how empathy—the ability to truly understand and feel what your customers are experiencing—becomes your most powerful tool for building trust, loyalty, and lasting relationships. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in customer experience, emotional intelligence, and trust-building:
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and creating environments where people feel heard and valued.
- **Professor Frances X. Frei, Harvard Business School:** Expert in service excellence and building trust through authentic connection.
- **Professor Adam Grant, The Wharton School, University of Pennsylvania:** Specialist in reciprocity, giving, and the power of empathy to drive engagement.
**What Today’s Coaching Will Help You With:**
You’ll practice seeing your business through your customers’ eyes, learn how to listen for unspoken needs, and discover how empathy can turn even a small interaction into a moment of genuine trust—so your hustle becomes a place where people feel understood, respected, and eager to return.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What is one frustration, worry, or challenge your customers face that they might not always share out loud?**
- Think about the emotions or concerns that might be bubbling beneath the surface.
2. **When was the last time you or your business could have been more empathetic to a customer’s situation?**
- Reflect on a missed opportunity or a moment where empathy would have made a difference.
3. **What is one small action you could take this week to show your customers you truly understand their experience?**
- Consider how you might adjust your language, process, or follow-up to demonstrate empathy.
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### Step 2: MBA Skill – Empathy in Action
Today’s MBA lesson is about putting empathy into practice:
- **Empathy Mapping:** Imagine you are your customer. What are they thinking, feeling, seeing, and doing at each stage of their journey with your business?
- **Active Listening:** When customers speak, listen not just for facts, but for emotions, frustrations, and hopes. Repeat back what you hear to show you understand.
- **Empathetic Language:** Use phrases like, “I hear how frustrating that must be,” or “I understand how important this is to you,” to validate your customers’ feelings.
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### Step 3: Coaching & Empathy Action Plan
After you reply, I will use the writings of Professors Edmondson, Frei, and Grant to:
- Help you identify the emotional undercurrents in your customer interactions.
- Guide you in crafting empathetic responses and actions that build trust.
- Suggest ways to practice active listening and empathy mapping in your day-to-day work.
- Offer examples of businesses that have turned empathy into a competitive advantage.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your empathy action idea.
- I’ll help you refine your approach, suggest ways to deepen your empathy, and offer next steps for making trust your signature move.
- Remember: Empathy isn’t just being nice—it’s the foundation of loyalty, advocacy, and real growth.
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Ready? Share your answers and empathy ideas below. Let’s hustle smarter, one lunch break at a time!
Secret Dessert Course
It’s Day 15 so I think I’m 15 days too late for this advice: You need to be journaling. Every. F#@$ing. Day.
It should be filled with moments of friction—as you experienced them– not just with customers, but within yourself. Empathy is so much more than a tool for mapping customer pain. It’s a muscle you flex every time you reflect on your own emotional responses to the challenges of building something new. Today’s dessert course is a private invitation to slow down and journal: to notice how your feelings shape your decisions, to spot patterns in your reactions, and to sharpen the empathy you bring to your business—and to yourself. Grab your notebook, your favorite snack, and a few quiet minutes. It’s time to get honest with the person in the mirror.
Prompt #2 - Empathy Journaling for Founders
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Prompt #2 - Empathy Journaling for Founders ○
**Today’s Focus: Empathy Journaling for Founders**
**Ivy League MBA Coaching by:**
- **Professor Laura Huang, Harvard Business School:** Expert in founder mindset and overcoming adversity.
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and learning from setbacks.
- **Professor Alison Wood Brooks, Harvard Business School:** Specialist in anxiety reappraisal and emotional self-awareness.
**What This Prompt Will Help You With:**
You’ll practice empathy journaling to deepen your understanding of your own emotional triggers and responses, making you a more resilient, customer-focused founder. This exercise builds self-awareness and helps you translate personal insights into stronger, more empathetic business decisions.
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### Step 1: Reflection Questions
Take a few minutes to answer these questions in your journal or digital notes. Be honest—this is for you, not for anyone else.
1. **Think back to a recent business challenge or decision. How did you feel in the moment?**
- Were you frustrated, nervous, excited, or something else? Describe the emotion and where you felt it in your body.
2. **How did your emotional state influence your actions or decisions?**
- Did you react quickly, pause, or avoid the issue? What did you notice about your behavior?
3. **Imagine your customer or team member in a similar situation. How might they feel?**
- How would you want someone to respond to you if you were in their shoes? What would make you feel heard or supported?
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### Step 2: Empathy Journaling Exercise
Set a timer for 5 minutes. Write freely about a recent interaction—with a customer, teammate, or even yourself—where emotions played a role. Focus on:
- **What you felt** (your emotions and physical sensations)
- **What you noticed about the other person’s emotions** (if applicable)
- **One small way you could respond with more empathy next time**
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### Step 3: Coaching & Insights
After you journal, use these prompts to reflect and plan your next steps:
- **What surprised you about your own emotional responses?**
- **How can you use this awareness to improve your next customer or team interaction?**
- **What’s one habit you’d like to build to practice more empathy—toward yourself or others?**
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**How to use this prompt:**
Copy and paste these questions into your favorite journal or AI assistant. Take a few minutes each day to reflect on your emotional responses and how they shape your decisions.