Day 2 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: Pinpoint Your Core Problem
Welcome to Day 2 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to help you (and me) build a side hustle that’s meaningful, impactful, and profitable. Today’s questions are designed to take the work we did yesterday– Day 1– on our Why and to narrow them into prioritized, actionable refinements. If Day 1 was about discovering your why, Day 2 is about identifying the what—the specific problem you’re going to solve first. Think of it as moving from initial spark (your why) to small flame (your what).
Today we turn yesterday’s inspiration into action. The goal is to move from a broad purpose to a single, concrete problem you can actually tackle—because focus–one of your big three skills– is what transforms ideas into action, into results.
If you’re playing along, today’s questions are:
1) Within the context of your day 1 answer, what’s the one problem you can’t stop thinking about—the one that keeps you up at night?
2) If you could only solve one problem for your audience, which would have the biggest impact on their lives?
The problem that keeps you up at night is the only one worth getting out of bed for.
Ok. Why do these specific two questions matter? Well, the first one is about further reducing scope. Narrowing your ambitions from that first broad why and what the question does is critical because it forces you to focus on what truly matters to you. To you personally. That “to you” part is really important. As much as you hear that EVERYTHING should be about the customer… EVERYTHING should be about listening to client voice… you need a psychological hack to get there. Because at its earliest stages, a side hustle will only get the love and attention it needs (from you) if you have either discipline or passion. And guess what? Most people don’t have discipline. But passion is a pretty reliable alternative. It can fuel the persistence you’re going to need… because if you’re solving a problem that deeply resonates with you, you’re creating the path to get to “EVERYTHING should be about the customer.”
When you pick a problem that matters to you, you’re more likely to stick with it through the inevitable setbacks. Passion is like jet fuel—use it or lose it. Although I’m not sure how you’d lose jetfuel. Unless you’re like a Canadian airline in the 80s. Or in 2001. I guess what I’m saying is don’t be a Canadian airline.
Anywho… That’s the difference between a hobby and a hustle. When I was a standup, there were comics who treated their material like it was a hobby and there were those who treated their material like it was a hustle. A hobby you do just for you. Make yourself laugh. But… the hustle, you’re doing that for the audience. The hustlers are all names you’d recognize. EVERYTHING should be about the audience. My point is that a real hustle starts when your focus shifts from what you want to what your audience needs most.
I also don’t think it's an exaggeration to say that the best businesses– the most enduring businesses– what I’d classify as epic hustles– started with founders who couldn’t ignore a particular problem— we’re talking OCD-level focus— whether it was a gap in the market, an inefficiency in a process, or just frustration they experienced firsthand. By identifying the problem that keeps you up at night, you’re adding kindling to the spark… to your why… you’re pinpointing an opportunity to create value– for yourself… for others who share the same pain point. So you’re doing this first part for you… for motivation… because money– or the potential of money– isn’t a sustainable motivation.
Sustainable hustles are built on solving real, persistent problems—not chasing trends, not quick wins, nothing easy. Don’t believe my stupid little hook about lunch breaks and salads. They’re just meant to kick off your longer journey. It’s going to be tough as hell to out-persist a persistent problem. But that’s no different than your day job. If you can do one, you can do the other.
Let me give you a cool example of sustainability, persistence and “The type of shit I'm on, you wouldn't understand”: James Dyson– the vacuum guy– spent five years and over 5,000 prototypes trying to fix one thing that drove him nuts—his vacuum kept losing suction. His friends thought he was OCD. But that relentless focus on a single, personal frustration turned into Dyson Ltd.—a company now worth over $10 billion. If you do it right, the problem you can’t stop thinking about is the one that changes everything.
Obsessing over the right problem isn’t some character flaw—it’s your competitive edge.
Ok. If you need more structure than what I’m saying– you can make this process I’m describing easier on yourself by using a simple framework like a "Problem Matrix." Google that: “Problem Matrix.” I’ll put a picture up of mine:
And I’ll explain it in the next section when I use my current hustle as a case study… but it's basically, you list all potential problems related to your Day 1 answers in one column and rate them based on criteria like personal passion (1-10), audience impact (1-10), and ease of execution (1-10). The highest-scoring problem is likely your best starting point! More on this shortly but the point is that a simple scoring system keeps you honest and helps you PRIORITIZE– superskill number 2– helps you prioritize what really matters.
Movin’ on though. The second question is about taking two of the three skills that we’re constantly developing to better manage our growing day job– the skills of prioritization and focus (minus delegation)— and applying them to the side hustle. By narrowing down to the single most impactful problem– to solve first– you’re making sure that your efforts create maximum value for those you want to serve. And this second question can’t be answered without talking to potential clients. Lots of them. It can’t be done without listening for the intersection of your ideas and their high impact problem– the ones that they care about.
Don’t build in a Dyson– that’s my stupid vacuum reference. Talk to real people, listen deeply, and let their feedback shape your priorities.
If you’re an introvert, this part’s going to take a toll because you need to engage a lot of potential clients and active listening is hard. I spoke with dozens of creators about their frustrations with algos controlling their reach. Talking to them helped me prioritize building tools that empower creators to own their platforms over other ideas I had initially considered. Interpreting what they’re saying into high impact hustles is hard. But it’s worth the effort. Solving a high-impact problem for that person– doesn’t just eliminate their pain– it builds trust and loyalty and deepens the relationship because it addresses something meaningful in their lives. It also sets the tone for how your hustle will grow over time— because solutions that resonate deeply tend to scale well and attract repeat customers.
The more you listen, the more likely you are to build something people can’t live without.
Two other bits of my own experience with side-hustles that are related and worth sharing on all this. 1) Companies don’t buy things. People in those companies buy things. You’re never selling to the company. You’re not even selling to the people. You’re building relationships with those people. And 2) master hustlers sell transformation; they sell a certain feel; they sell identity and community. When people– not companies– feel that their lives are better because of what you offer, you’re winning. They become your champions, they advocate for your brand. They become your hype squad - your unpaid interns working 24-7 to have their friends slide into your DMs shouting 'SHUT UP AND TAKE MY MONEY'." So… answering Day 2’s questions thoughtfully ensures your hustle connects emotionally with your next champion, and your next and your next.
Ok. Take a moment and try to answer the Day 2 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: 💼 Apply the Jobs-to-be-Done Framework: Today's Ivy League MBA Skill
Day 2, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. It’s Taco Tuesday– my favorite lunch of the week. And the MBA skill we’re going to pick up today is something called the Jobs-to-be-Done framework. As frameworks go, it’s like the shredded lettuce in your taco. It’s not spicy– the good part– but it adds freshness to each bite. It’s like purpose– it makes everything go down easier.
The Jobs-to-be-Done framework is just a way of thinking that was popularized by a guy named Clayton Christensen in a book called Competing Against Luck. And I know, it sounds like more MBA jargon, but stick with me.
The example in the book that everyone remembers is the McDonald’s milkshake. The owners of the chain used the Jobs-to-be-Done framework and realized that many of their customers were buying milkshakes not for taste– and obviously not for nutrition– but to make their long, boring morning commutes a little more enjoyable. That might sound obvious but it's kinda brilliant because once you understand the job the milkshake was hired to do– if you want to keep those drivers happy– you don’t make the shake easier to drink. You make it harder to get through the straw. So it takes longer to finish it. It’s doing its job better.
Christensen’s big idea was that: nobody buys a product just for the sake of owning it. They “hire” it to do a job in their life. That’s it. It’s that simple. It should make you wonder why you’d pay Ivy League prices for an MBA. That’s the whole framework. Which should tell you… You’re selling a solution to a real problem, a way to get something important done, to feel a certain way, to make life easier or better or more fun. And if you don’t know what job your hustle is being hired to do, you’re SOL.
So, let’s bring it home. Think about the questions you need to answer today. You need to narrow down your Day 1 “why” to the one problem you can’t stop thinking about, the one that keeps you up at night. That’s a job that needs doing. And your audience? They’re out there looking to “hire” something—anything—that gets that job done for them. They don’t care about your features or your clever branding or your origin story, at least not at first. They care about getting their job done, period.
Another way to look at it: imagine your hustle as a candidate in a job interview. Your customer is the boss. The job description? Solve their problem, deliver their desired outcome, make their life better. If your hustle can’t clearly explain what job it’s applying for, or if it’s not the best candidate for that job, it doesn’t get hired. It’s that simple.
Let’s make it even simpler. Take a sec and think about your product or service. Finish this sentence: “People hire my [thing] to help them ______.” Fill in that blank. Don’t overthink it. Don’t make it fancy. Just get to the core. Are they hiring you to save time? To feel confident? To avoid embarrassment? To get healthier? To look smarter in meetings? The more specific you get, the better.
And here’s the thing: sometimes the job is obvious and functional… like “I need to get lunch fast because I only have 20 minutes.” Sometimes it’s emotional… like —“I want to feel like I’m making progress on my goals.” Sometimes it’s social… like—“I want to look cool to my friends.” The best hustles nail all three. They solve the practical problem, but they also deliver a feeling and maybe even a little status boost. That’s how you build something people actually want to use.
Now, let’s tie this back to today’s questions. When you picked the one problem you can’t stop thinking about, you were really identifying the main job your hustle is being hired to do. And when you asked which problem, if solved, would have the biggest impact for your audience, you were getting at the “must-have” job—the one that’s so important, people will actually pay for it, talk about it, and maybe even tell their friends.
This is where the Jobs-to-be-Done mindset flips everything. Instead of asking, “What should I build?” you start asking, “What job is my audience desperately trying to get done, and how can I help them do it better, faster, or with less pain than anything else out there?” That’s the question that leads to real insight, real demand, real momentum.
So take a second: take your Day 2 answers and write out a “job statement.” It’s as simple as, “Help me ______.” Or, “I need to ______.” Or, “I want to avoid ______.” If you can’t fill in those blanks for your hustle, you’re not ready to build yet. If you can, you’re way ahead of the game. Say it out loud. Share it with a friend. Ask them if it makes sense. If they don’t get it, try again. If they say, “Oh, I need that,” you’re onto something.
And don’t stop with just one job. Most great hustles get hired for a main job and a few side gigs. Think about the functional job, the emotional job, the social job. Write them all down. The more clearly you see what jobs your audience needs done, the more likely you are to build something they’ll actually hire—and keep hiring.
And keep telling yourself that you’re building a solution that gets a job done for real people, in the real world. If you keep that front and center, you’ll hustle smarter, not harder. And that’s how you turn your lunch break into something way bigger than just another delicious taco.
Part 3: Examine My What: The 28-Day Case Study
This is Day 2, Part 3 of Lunch Break Millionaire. This is the segment where we #BuildinPublic– where I answer the daily questions from part 1– using the MBA skills we just learned in part 2– and showing my work here in part 3– 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 apply today’s questions to my current side hustle so you can get a real world example. Question 1 was: Within the context of our day 1 answer, what’s the one problem you can’t stop thinking about—the one that keeps you up at night?
Let me put up my problem matrix– all my potential problems related to my Day 1 answers in one column and my ratings for them.
I even fed it to my AI and it produced this:
But let me explain it all.
Quick confession: I’m an ideas guy so I started with hundreds of ideas about how to serve content creators. That’s not an exaggeration. Hundreds of ideas about how to help creators own their content, own their followers, own their revenue. But of all the ideas, I couldn’t stop thinking about two of them. One is what I call the Substack problem (and I’ll explain in a second) and the other is an idea that’s been guiding my designs for years. I call it humble design and we’ll come back to it.
First, the Substack problem.
If you’re not familiar with SubStack, I full-on love them. They’re an absolute gift to content creators. They offer a platform that champions independence and creativity like no other. It allows writers, podcasters, and video creators to connect directly with their audiences through beautifully simple email newsletters. What’s really cool is how it puts creators in control—whether it’s through paid subscriptions that keep the majority of creators earnings in their pockets or tools like analytics and SEO that help them grow. Substack– to me– isn’t just a platform; they’re a partner in helping creators thrive without interference from algos or middlemen.
So… I hope that you get that I’m fawning over them. They share my values– the kind of unwavering commitment to empowering creators– in their case, mostly writers– to own their work and build meaningful relationships with their audiences. For anyone who values storytelling, connection, and independence, Substack– when compared to the social media giants– Substack is nothing short of a revolution—and it deserves every ounce of praise for what it’s doing to elevate creators everywhere.
And guess what? I don’t think SubStack goes far enough. I don’t think their business model can– because it’s about a shared platform; it's about owning the code; and letting creators rent it. They have noble ambitions but because of their design choices, those ambitions will break as they scale– and definitely if they head to the public markets– if they get bought or go public– it all goes to shit– the same way Facebook went from cool to scary, the same way Google went from “don’t be evil” to we have shareholders who really need us to be evil.
So Substack is a giant step forward… and still leaves creators renting, not owning. And that little insight led me– during my Day 2 exercise– to narrow my why to my first what. I’ll offer content creators a mobile app that’s 100% theirs. It won’t even have that little stupid “powered-by” ad at the bottom. I’ll go total open source. They can use it as a supplement to something cool like Substack or something evil like Instagram, Facebook, YouTube, TikTok…. Or content creators can go fully independent with their mobile app– their platform– and detach from the mothership completely. They don’t have to say goodbye to social media– they can just use those platforms as funnels to their platform, their business… which they own completely.
Part 4: Continue the Case Study
This is Day 2, Part 4 of Lunch Break Millionaire. Just finishing up today’s #BuildinPublic segment.
Ok, we just answered today’s first question… What's the ONE thing you should offer first? And because every rule is worth breaking. I didn’t stop with one product– a mobile app in every pot. I committed to two products. The second product is complementary to the creator-owned mobile platform and it’s based on my personal design philosophy– what I call humble design.
If you’ve never heard me talk about humble design, I always start by explaining the opposite: arrogant design… which is what the entire current paradigm is: every website saying “if you want my value, come to me… come to my site.” It's a little better if the site offers an API but even that is still “if you want my value, do the technical work required to integrate my value into your context.” Which is better(?) I guess… but still arrogant.
Humble design says…. Hey… I recognize that you– as a consumer of my content– don’t live your digital life on my digital properties. You have your own systems, your own preferences, your own digital habits; and that it shouldn't be your responsibility to make my life easier; it shouldn't be your responsibility to do the hard work of integrating my value into your digital experience.
So humble design asks the most obvious question in the world: where does the client already live digitally? It's the most important question and the only people asking it right now are advertisers– digital mosquitos. And they’re not asking to add value to your experience. They’re asking to interrupt it.
Humble design encourages you– as a content creator, as a business– to figure out where your users already go and to wait for them there…. To integrate your value into their digital destination. Not just drive them to your portal. Not just drive them to your app. But… integrate your content into the sites they already live in.
Enter my second answer to “what’s the one thing you should offer?” And I’ve built it already. An embedded AI agent that follows a creator’s audience on their unique browsing journeys and looks for ways to integrate the creator’s content into other people’s sites– the ones their audience are visiting. An AI agent that says “Oh hey, you’re on The New York Times or The Wall Street Journal or Reddit and there’s some content here that your favorite creator– me– has some complementary content for.
If you haven’t seen the demo of what I’ve built, now’s a good time to look for the link in the post description and see it in action. I probably didn’t get the product right, but that’s why I’m sharing. Once I get it right, it should feel– to the audience– like their favorite creator is sitting next to them as they browse…. Saying “read this article on this site because I have something that builds on it. Listen to this content on the site you’re currently on because I have an opinion on it. Watch this content– right here– because I have something that’s cool and related.”
I’ll close with some key decisions from doing this exercise for myself:
1) Like every other founder on the planet, I thought a lot about Apple—and how people don’t just buy iPhones; they buy into an identity– they buy into innovation, simplicity, status. And I kept asking, what’s the identity that I care deeply about? Looking for emotional connection helped me get from my why to my what.
2) The exercise forced me to validate my gut instinct with actual data… from conversations with real creators struggling with algo issues. The exercise forced me– Mr. Introvert– to shoot the shit with creators who I didn’t know across platforms like Instagram and YouTube—and that gave me invaluable insights into their pain points!
3) Don’t be surprised in the next 28 Days if you hear the language of revolutions and uprisings because the most important insight– the one that stood out during these interviews– was how often creators felt powerless against the algos. They described it as being at war with an invisible enemy. They inevitably used emotionally-charged language– and that will help me refine my messaging.
4) During those conversations I tested some early prototypes– shared some mockups– and their excitement was genuine. Nothing validates that you’re on track like seeing genuine enthusiasm. It validated exactly how important early feedback loops are if you want to hustle smarter..
Prompt #1 - From Why to What – Pinpointing the Problem Worth Solving
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Prompt #1 - From Why to What – Pinpointing the Problem Worth Solving ○
Welcome to Day 2 of your 28-day Lunch Break Millionaire journey! Today, you’ll narrow your big “why” from Day 1 into a single, high-impact problem that your side hustle will solve first. You’ll be coached by Ivy League faculty whose research is foundational in problem validation and customer-centric innovation:
- **Professor Clayton Christensen, Harvard Business School:** Creator of the Jobs-to-be-Done framework and expert in identifying real customer pain points.
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and learning from customer feedback.
- **Professor Sunil Gupta, Harvard Business School:** Expert in value creation, business model innovation, and prioritization.
**What Today’s Coaching Will Help You With:**
You’ll move from inspiration to focus-pinpointing a problem that matters deeply to you and your audience, and learning how to validate that it’s worth solving.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **Within the context of your Day 1 answer, what’s the one problem you can’t stop thinking about-the one that keeps you up at night?**
- This is about narrowing your ambitions from a broad “why” to a single, actionable “what.” Focus on what truly matters to you and could fuel your persistence.
2. **If you could only solve one problem for your audience, which would have the biggest impact on their lives?**
- Think about what would be most transformative for your ideal customer. What pain, if eliminated, would make them say, “I can’t live without this”?
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### Step 2: MBA Skill – Jobs-to-be-Done Framework
Today’s MBA lesson is the Jobs-to-be-Done (JTBD) framework, pioneered by Professor Christensen. The core idea:
> Customers “hire” products and services to do a specific job in their lives.
- Write a simple “job statement” for your hustle:
- “People hire my [product/service] to help them _______.”
- Or: “Help me _______.”
- Or: “I need to _______.”
- Consider the functional, emotional, and social jobs your audience needs done. The more specific, the better.
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### Step 3: Prioritization Matrix (Optional)
If you have multiple problems in mind, use a simple matrix to rate each on:
- **Personal Passion (1–10)**
- **Audience Impact (1–10)**
- **Ease of Execution (1–10)**
Choose the problem with the highest combined score as your starting point.
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### Step 4: Coaching & Validation
After you reply, I will use the writings of Professors Christensen, Edmondson, and Gupta to:
- Help you clarify and refine your problem statement so it’s focused and actionable.
- Guide you in applying the JTBD framework to ensure your hustle solves a real, “must-have” job.
- Offer practical tips for validating your problem with real customers (mini-interviews, surveys, or observation).
- Share a real-world case study showing how focus and validation lead to breakthrough businesses.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft “job statement.”
- Your Ivy League coaching panel will help you refine your problem statement, validate your focus, and suggest next steps.
- Remember: This is about narrowing your focus to what matters most-so your hustle starts with momentum, not overwhelm.
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Ready? Share your answers and job statement below. Let’s hustle smarter, one lunch break at a time!
Secret Dessert Course
The AI prompt below helps you create a problem validation mini-interview script. The idea is to read the script to a potential customer to validate your thinking about your hustle.
Why use it?
Well, before you invest a ton of time or money into building the rest of your hustle, you first want a direct line to the people you hope to serve— your potential customers. The prompt below takes your idea out of your own head and puts it to the real-world test: Do others actually experience the problem you want to solve, and do they care enough to want a solution? By using a simple, conversational script, you’ll (hopefully) quickly discover whether your chosen problem is urgent, painful, and widespread-or just a personal annoyance.
These early interviews help you avoid wasting months building something nobody wants, and instead, let you refine your idea based on real HUMAN feedback. I capitalized “human” because this exercise should NOT start and end with the AI.
The face-to-face process not only builds your confidence, it also gives you the language and insights you’ll need to attract your first users, partners, or investors. In other words, this mini-interview is your shortcut to building a business people genuinely need-before you spend a single dollar on solutions.
Just copy and paste this prompt into your favorite AI assistant to enjoy Day 2’s dessert course.
Prompt #2 - Problem Validation Interviews
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Prompt #2 - Problem Validation Interviews ○
Today is Day 2 of your 28-day business journey. The focus: validating that the problem you identified is real and painful for others-not just for you. You’ll be coached by real Ivy League faculty with expertise in customer discovery, innovation, and entrepreneurship:
- **Professor Clayton Christensen, Harvard Business School:** Pioneer of the Jobs-to-be-Done framework and customer-centric innovation.
- **Professor Eric Ries, Yale SOM guest lecturer (Lean Startup):** Expert in validated learning and rapid feedback.
- **Professor Amy Edmondson, Harvard Business School:** Renowned for her research on psychological safety and how to ask open, honest questions that get real answers.
**What Today’s Coaching Will Help You With:**
You’ll learn how to reach out to 3–5 potential customers and run short, effective “problem validation” interviews. The goal: avoid building in a vacuum by hearing real voices and real pain points before you commit to your solution.
**Step 1: Instructions & Sample Script**
Here’s a simple script you can use to reach out to potential customers (friends, colleagues, LinkedIn contacts, or online communities):
> “Hi [Name], I’m working on a new project and would love your quick perspective. I’m trying to understand if [describe the problem in one sentence, e.g., ‘finding healthy lunch options during a busy workday’] is something others struggle with too. Would you be open to a 10-minute chat? No sales pitch-just want to learn from your experience.”
During the conversation, try these interview questions:
- “Can you tell me about a recent time you experienced [the problem]?”
- “How did you try to solve it? What worked or didn’t?”
- “How big of a pain is this for you, really?”
- “If you could wave a magic wand, how would you want this fixed?”
**Step 2: Reflection Questions**
Please answer these before you reach out:
1. Who are 3–5 people you could talk to this week who might have experienced this problem?
2. What’s your one-sentence description of the problem you want to validate?
3. What’s your biggest fear or hesitation about reaching out for these mini-interviews?
4. (Optional) What type of business are you building (industry, product/service, target customer)? If you’re in a specialized field, let us know so we can bring in additional Ivy League customer discovery experts.
**Step 3: Coaching & Debrief**
After you reply, I will use the writings of Professors Christensen, Ries, and Edmondson tol:
- Help you refine your outreach script and interview questions for maximum honesty and insight.
- Coach you on how to interpret feedback (what’s real pain vs. polite noise).
- Guide you in deciding if your problem is worth solving-or if you need to pivot.
- Suggest additional Ivy League experts if your business is in a specialized field.
Please respond with your answers to the questions above. After you do, your Ivy League coaching panel will guide you step-by-step through validating your problem with real customer conversations.