Day 29 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: Turn Churn Into Growth
In the heat of firefighting– when things are going wrong and clients are starting to walk– it’s easy to miss the gifts right in front of you—every misstep, every complaint, every bit of feedback, is a big, beautiful piñata. And that’s the exact right metaphor, because you now know how to get the candy out.
Welcome to bonus week– week 5– Day 29 of starting your side hustle! We finished our month-long journey, and this week is all about all the lessons I wish we’d had time for. Today’s focus is a little all over the place. I want to touch on retention, recovery, loyalty. It’s meant to be a kind of masterclass on turning feedback, churn, breakdowns… into piñata candy– sour-patch kids… into growth.
I was originally going to do today’s topic last week– during scale week– because of 2 reasons. 1) Retention is a scaling lever. If your bucket has a hole in it, it’s worth your time to fix it because depending on the size of the hole, focusing on retention might get you more growth than everything you learned during sales week. Plus, if you’ve delegated sales– superskill #3–, it’ll drive your salespeople crazy to lose the clients they worked so hard to land. Reason #2: churn– another word for retention– is a different kind of strategic signal (Day 25)... it’s a source of data (Day 26) for the kind of product and process improvements (Day 24) that let you scale.
So yeah. I suck. Teaching is probably the hardest thing I’ll ever do.
Our real life example today is Des Traynor, co-founder of Intercom. Early on, he noticed that when customers left Intercom, it wasn’t always because the product failed—they often just outgrew the plan or needed something different. Instead of treating those goodbyes as a dead end, Intercom built automated “win-back” campaigns, exit surveys, and special upgrade offers… They built thoughtful offboarding workflows. They learned from every goodbye, improved their product, and even converted departing users into advocates and return customers. His story– Intercom’s story– is about how churn– how every goodbye– is a goldmine for learning, upgrades, referrals.
So… the two questions we’re going to ask today:
1. What’s the most valuable piece of feedback hiding in your latest firefight?
2. How can you turn every complaint, every exit, every mistake into a gift that makes your business better?
Both questions matter because they force you to slow down and look for the candy hidden in the chaos– the piñata candy. That first question is training your brain to see past the noise and frustration, to spot the insight that can actually move your business forward. It’s a tough skill to master but the best ideas are buried in the heat of the moment. The second question matters because it helps you build a habit of transformation. You need to stop seeing problems as setbacks. You need to start treating them like opportunities. To learn… To improve, To strengthen your business. Both questions help you develop a mindset that’s pretty rare in business– one that sees feedback—especially the tough kind—as something to celebrate, as something to fuel growth… if you can survive it.
Ok. Take a moment and try to answer the Day 29 questions for your hustle without AI and before you listen to the next section-- the 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: 💼 Profit From Churn: Today's Ivy League MBA Skill
I do think most companies treat outages and customer departures as a kind of piñata party. They definitely blindfold someone. They definitely hand them a stick. They definitely spin them around to make them dizzy.. They just make sure that when the spinning stops, that well-armed lunatic is facing all the kids, not the piñata.
Day 29, 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, I’m going rogue. Just having dessert. Because all the best desserts require you to beat something– eggs, cream, batter, dough, frosting. Dessert is a great example of the joy that can come from a good beating. Making it metaphorically perfect for a conversation about how to enjoy a good beating. How to have a playbook that lets your business benefit from the beat down.
Today’s MBA skill is: churn strategy– a playbook for when you and/or your hustle are the piñata.
Let’s talk through the playbook you’ll need… the moves you’ll actually want to make when someone’s approaching you with a menacing stick… metaphorically.
First… start by looking at which clients are leaving or threatening to leave… when, and why. Dig into the stories behind each exit and potential exit. Segment them by customer type, product, experience. When a customer leaves feedback—especially a complaint—pause and treat it as a gift. Thank them, even though it’ll sting. Next, create “graduation moments” which is jargon for… replacing generic goodbye with a much more personal offboarding playbook. One that asks for honest feedback. One that offers a parting gift. One that keeps the door open.
Share what you learn with your team. Use those insights to improve your product, your service, your support. Build a recovery playbook that anticipates the most common breakdowns. Script your ideal response to each—like… what to say, what to offer, how to follow up. And make sure everyone on your team knows they’re empowered to fix problems on the spot.
Every complaint is a gift. Use it to improve your product, your process, or your people. When you go above and beyond to make things right, ask for a testimonial or a referral. Let those stories become part of your brand legend. And don’t forget your alumni. Reach out to former customers with a thank you, a check-in, or a special offer. Sometimes, the ones who left become your biggest fans.
Here’s how to put everything I just said into action– whether it’s today, 6 months from now… 6 years from now.
Review your last 10 customer exits. What patterns do you see? Figure out your top three most common breakdowns. Write out your ideal recovery response for each. Set up a recurring system/process to capture, analyze, and act on customer complaints.
And don’t wait for people to grab a stick. For instance, this week, reach out to one former customer or one former prospect that didn’t say yes. Reach out without a pitch… just gratitude and curiosity. That’s how you hustle smarter.
Part 3: Design Graduation Moments: The 28-Day Case Study
What if I told you that one of America’s most beloved brands built its reputation on how it helps people through their hardest goodbyes?
This is Day 29, 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. Most people don’t think about strategies for growing thicker skin. We all just figure that it happens naturally as life beats you down over and over and over again. Starting a side hustle just accelerates the beat downs. That’s what today’s conversation about churn was really about: thinking strategically about your reaction to a beat down. Turning it into a positive.
Most young-ish business owners treat churn like some dirty little secret—something to hide, something to fix. They obsess over every lost introduction, every “no thanks,” every silent unsubscribe. They haven’t yet grown their thick skin. Because experience changes your instincts– from “patch every hole every day” (which you should)… to… design a better hustle.
So let’s talk graduation moments for metatorial and superserious. We’re manually tracking when our creators hit certain milestones—like publishing their 50th curated post, or when their audience engagement’s doubled. Instead of begging them to stay on the basic plan, we’re trying to get that to trigger a “graduation” message: “You’ve outgrown the starter tier—are you ready to unlock advanced analytics and custom branding?” Suddenly, potential churn becomes a celebration. If we do it right, our creators feel seen, celebrated. In theory, upgrades go up. Social capital gets built. And yeah, I need to automate all of this but right now, a personal message from me is kinda cool, very human.
Will everyone upgrade? Hell no. Some will even leave. When I was a younger man, I’d write them off. Now that I have gray hair? I reach out. I thank them. I ask them what didn’t fit. I offer a “refer a friend” bonus… or something of value for free. Why? Because they bought into my dream. It’s that simple.
In my experience, my best referrals come from people who didn’t buy anything—people who left for a better fit. They respected what I was trying to do and how I was trying to do it. And they sent me prospects who were perfect for what I offered. They actually know better than I do. They have a real perspective that I try to fake.
And all that taught me. It should teach you. Churn isn’t failure. It’s a fork in the road—one path leads to upgrades, the other path leads to… referrals. And that learning forces me– in every new hustle– to design graduation moments and treat every exit like it’s an opportunity.
I’ll close today with my favorite example of getting churn right: Chewy. They’re an online pet supply company, but they’ve already reached legendary status– not because of their fast shipping or endless dog toys. No. When a customer cancels a subscription because their pet has– sadly– passed away, Chewy sends flowers. Sometimes a handwritten card. Sometimes a portrait of the pet. No sales pitch, no win-back offer. Just a moment of deliberate empathy. The result? Most dog people will– after grieving– inevitably get another dog. And when they do, they will never ever buy dog food from any company other than Chewy. And those few dog moms and dog dads who choose to live without a dog– I’m talking about people who will never buy from Chewy again– well, they become Chewy’s loudest advocates. They tell everyone they know. That(!) is churn turned into a referral engine-and a brand story that money can’t buy.
Prompt #1 - Turn Churn Into Growth
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Prompt #1 - Turn Churn Into Growth ○
Today, you’ll learn to see customer churn not just as a loss, but as a goldmine for insight and growth. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in customer retention, behavioral economics, and business model innovation:
- **Professor Peter Fader, The Wharton School, University of Pennsylvania:** Leading expert on customer lifetime value (CLV) and retention analytics.
- **Professor Frances X. Frei, Harvard Business School:** Authority on service excellence and turning customer exits into loyalty opportunities.
- **Professor Sunil Gupta, Harvard Business School:** Specialist in digital business models and using churn data to drive smarter strategy.
**What Today’s Coaching Will Help You With:**
You’ll benchmark your churn rate against industry norms, uncover why customers leave, and design “graduation moments” that turn exits into brand advocacy or even new revenue streams-so churn becomes a lever for growth, not just a metric to fear.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **What is your current churn rate (monthly or annual), and how does it compare to industry benchmarks for your type of business (SaaS, ecommerce, services, etc.)?**
- If you don’t know your churn rate, estimate how many customers you lose each month or year.
2. **What are the top reasons your customers leave, and how do you know?**
- Are you tracking exit surveys, support tickets, social media, or just guessing?
3. **What’s one thing you could do to learn more from exiting customers or to keep the door open for their return?**
- Think about exit interviews, “win-back” offers, or ways to celebrate customers who “graduate” from your service.
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### Step 2: MBA Skill – Profit From Churn
Today’s MBA lesson is about “Churn Alchemy”:
> The best businesses turn customer exits into learning loops and new opportunities.
- Benchmark your churn rate: SaaS (5–7% monthly is healthy), ecommerce (3–5% monthly is average), services (2–4% monthly is strong). If you’re above these, you’re in the danger zone; if you’re below, you’re best-in-class.
- Map your top churn reasons. Are they fixable (onboarding, support, pricing) or natural (customers outgrow you)?
- Design a “graduation moment”: When a customer leaves on good terms, celebrate their journey, ask for feedback, and offer ways to stay connected (referral, alumni group, special offer).
- Use churn data to improve your product, messaging, or customer experience. Every exit is a chance to get better.
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### Step 3: Coaching & Action Plan
After you reply, I will use the writings of Professors Fader, Frei, and Gupta to:
- Help you benchmark your churn rate and interpret what’s normal vs. what’s a red flag.
- Guide you in diagnosing root causes and prioritizing fixes that matter most.
- Suggest ways to turn exits into advocacy, referrals, or even future sales.
- Offer examples of businesses that grew stronger by embracing and learning from churn.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your churn insights.
- I’ll help you benchmark, learn from, and profit from churn-so you build a business that gets better with every customer cycle.
Secret Dessert Course
Every company loses clients. The question to answer is whether your churn rate is normal. The AI prompt below is a “Churn Benchmarking Guide” that is here to save your sanity and give you an industry-specific data-driven perspective.
No need to panic over every lost customer. The AI can ground you in your industry’s normal churn rate- whether you’re running a SaaS, ecommerce, or service-based business. You’ll quickly see if you’re in the danger zone or just experiencing the natural ebb and flow that even the best companies face.
Just copy and paste the following prompt into your favorite AI assistant to enjoy Day 29’s dessert.
Prompt #2 - Benchmark Churn Metrics
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Prompt #2 - Benchmark Churn Metrics ○
**Today’s Focus:**
Compare your churn rate to industry standards and learn whether you’re in the danger zone or experiencing normal fluctuations. You’ll be coached by Ivy League faculty with expertise in customer retention, behavioral economics, and industry benchmarking:
- **Professor Peter Fader, The Wharton School, University of Pennsylvania:** Leading expert on customer lifetime value (CLV) and retention analytics.
- **Professor Frances X. Frei, Harvard Business School:** Authority on service excellence and turning customer exits into loyalty opportunities.
- **Professor Sunil Gupta, Harvard Business School:** Specialist in digital business models and SaaS/ecommerce metrics.
**What Today’s Coaching Will Help You With:**
You’ll learn how to interpret your churn rate, contextualize it against industry norms, and take action to stabilize or improve it-without panic or complacency.
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### Step 1: Reflection Questions
**Answer these in a few sentences each:**
1. What is your current monthly/annual churn rate?
2. What industry are you in (SaaS, ecommerce, service-based, etc.)?
3. What is the main reason customers leave (price, product fit, service, etc.)?
4. (Optional) What tools do you use to track churn (e.g., ProfitWell, Baremetrics, custom dashboards)?
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### Step 2: Coaching & Benchmark Analysis
After you reply, I will use the writings of Professors Fader, Frei, and Gupta to:
1. **Compare Your Churn to Industry Standards:**
- *SaaS:* 5-7% monthly churn (healthy), >10% (danger zone).
- *eCommerce:* 3-5% monthly churn (average), >7% (critical).
- *Service-Based:* 2-4% monthly churn (strong), >5% (needs intervention).
2. **Diagnose Your Situation:**
- If **above benchmark**: Identify 1-2 high-impact fixes (e.g., exit interviews, onboarding tweaks, loyalty programs).
- If **at/below benchmark**: Highlight retention strengths and warn against complacency.
3. **Offer Actionable Next Steps:**
- For high churn: “Implement a 3-question exit survey this week to uncover root causes.”
- For healthy churn: “Double down on your ‘wow’ moments-how can you surprise 10% of customers this month?”
**Example Framework:**
- **Danger Zone:** “Your 12% SaaS churn signals urgent action. Let’s audit your onboarding and pricing tiers.”
- **Normal Fluctuations:** “Your 4% ecommerce churn is expected post-holiday. Focus on reactivation campaigns.”
- **Best-in-Class:** “2% service churn? Celebrate-then replicate what’s working for your top 20% loyal customers.”
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**How to use this prompt:**
- Respond with your churn rate and industry above.
- Your Ivy League panel will return a tailored analysis with clear benchmarks and action steps.