Day 19 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: Cat Food > Spam
If you were to compare our digital lives to some metaphorical war, cold calling and email campaigns would be atrocities. They’re intentional, large scale violence… that– and I can’t believe I have to say this– that you should avoid. No exceptions.
Welcome to week 3– sales week– Day 19 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Today’s topic are trust killers… specifically, cold calling (evil #1) and email as a scalable sales channel (evil #2).
If you’ve ever been on the butt end of a cold call or spam– and all mass emails are spam– you might be wondering when we’re going to train you on how to use these amazing sales tools.
The answer is never. Cold calling stopped being a successful sales strategy 20 years ago… maybe even more than that. And when it comes to email (as a channel), the “scalable” approach of mass emailing– using Constant Contact, MailChimp (which I mentioned on Day 6), HubSpot, etc… spamming is one of the most expensive mistakes you can make. Email campaigns look like an easy button, but for a young business– any sized business really– they cost you the one thing you can’t afford to lose: trust. So, you’ll want to flip the script on cold calling and email as a channel. No ifs, ands or buts.
A real life example here is someone I really respect: Paul Jarvis, creator of Fathom Analytics. Paul built his business by sending thoughtful, personal emails to his audience—never blasting generic newsletters (a mistake I personally have made in the past). He treated every subscriber as a real person. He replied to everything himself. There was a decency in how he approached the channel that isn’t there today. His approach built deep trust and loyalty, and it led– for Paul– to high open rates and word-of-mouth growth. Fathom Analytics became profitable without paid ads or spammy campaigns and all because one dude used email as a relationship tool, not an automated megaphone.
Today I’m going to try really hard not to spiral into angry rants about email campaigns. One example. My least favorite line in what are clearly automated follow up emails– like the 3rd or 4th email you’ll get from someone who clearly bought your email address. The line: “I hope you don’t mind my persistence, but I’m just really passionate about helping clients like you.”
Are you though?
Ok… while that’s still top of mind, here are the two questions you should be asking today:
1. How can you use research to make every email– every one-to-one email– feel like a face-to-face introduction?
2. What would it look like for you to use your phone email as a tool for service instead of marketing?
Ok– that first question. Imagine you’re meeting a potential client or someone you’re going to interview with. You’d never walk in cold—you’d check their LinkedIn, read their latest work, maybe even find a mutual connection or two. Why should email be any different? The best emails– aside from warm intro emails someone writes on your behalf– are the ones that show you’ve done your homework: and I don’t just mean “you’ve read their LinkedIn profile. I mean you’re referencing a recent project, a shared interest, a specific challenge that they’re facing… that you know they specifically are facing. How? They have friends and colleagues who in turn have friends and colleagues. Sweat the 6 degrees of separation between you.
This level of research takes more time, but it transforms your outreach from “just another annoyance” to a genuine, memorable connection. Why does this matter? Because in the early days, every new relationship is precious—and every first impression counts.
That’s why question one matters.
The point of asking question two is the word marketing is about scale (breadth) but the word service is about depth. Instead of thinking, “How do I reach 1,000 people at once?” ask, “How do I serve one person? How do I make them– that one person– feel like they’re the only one who matters?”
This means using your phone and your email to answer questions– not to ask what questions they’re asking. It means using all your comms channels to offer tailored advice… to check in with a thoughtful note.
So no salesy ask. Just service. Yes, it’s more work. But it’s the kind of work that builds trust. In the early days of a business. Every client-facing action you take should help build you a reputation for care and attention, not efficiency or scale.
There is no word-of-mouth– no referral— that starts with “that guy’s really efficient.” Every channel– but especially email because so many people live there– should be a source of delight, not digital noise; not your elevator pitch; not asking for time or anything else.
Ok. Take a moment and try to answer the Day 19 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: 💼 Research Your Six Degrees of Warmth: Today's Ivy League MBA Skill
Day 19, Part 2 of Lunch Break Millionaire– where we turn whatever you're eating for lunch into an Ivy League MBA degree. It’s Taco Friday– it’s Tacos EVERY day! And the MBA skill we’re going to pick up today: how to play Six Degrees of Kevin Bacon.
After spending four days on skills that build trust—empathy, active listening, curiosity, and transparency—today we’re focusing on the flip side: common sales practices that can destroy trust. The MBA lesson here is about equipping you with a unique, actionable skill to help you avoid these trust-killers, especially when reaching out to new contacts.
Today’s MBA skill: how to mine your social network. Step aside Kevin Bacon. We’re going to do something I call Six Degrees of Warmth. We’re going to use social proximity to get trustworthy introductions.
OK. A disappointingly large number of sales and business content tells you to “cold call” or “cold email” prospects— but these methods are necessarily transactional, they’re invasive, they’re fundamentally insincere. The result? Instant trust erosion. So instead, let’s use a framework inspired by social network theory and “six degrees of separation”: the idea that you’re never more than a few connections away from anyone in the world.
This approach is about systematically mapping your social and professional networks to identify the most credible, relevant, and respected person who can introduce you to your prospect. This is a technique emphasized in Ivy League MBA programs for business development, networking, and sales strategy, often referred to as “social network mapping” or a “warm introduction strategy.”
How do you do it? 5 Steps. Let’s go step by step:
Step 1. Map Your Network:
- List out your direct connections (friends, colleagues, mentors, alumni).
- For each, consider their own networks and industries.
Step 2. Identify Proximity (that’s a fancy way of saying how close they really are to you– how well do you really know them):
- Use LinkedIn or other social platforms to see if any of your connections are connected to your prospect.
- Look for mutual interests, shared groups, or past collaborations.
Step 3. Assess Credibility:
- Choose the connection who is most respected by both you and the prospect.
- The stronger the relationship between your connection and the prospect, the warmer and more credible the introduction.
Step 4. Craft the Ask:
- Ask your connection if they’d be willing to make an introduction.
- Provide context about why you want to connect and how it could be mutually beneficial.
Step 5. Prepare for the Intro:
- Give your connection a short, clear message they can forward.
- Offer to draft the intro email for them if they prefer.
Why does this work?
- There’s a principle in social psychology called Trust Transfer. People trust recommendations from those they know and respect. A warm introduction transfers some of that trust to you.
- The other reason is that there’s also a smaller level of perceived risk. Prospects are more likely to engage with someone who comes recommended.
Third reason:
- It’s evidence-based. Research shows that warm introductions significantly increase the likelihood of a successful business relationship compared to cold outreach. And before you ask me for exactly which piece of research, I inferred it from best practices in MBA curricula from Harvard and Wharton classes.
A quick example:
Imagine you want to pitch your software to a potential client at a large company. Instead of cold emailing, you check your network and find that your former boss is connected to the client’s manager on LinkedIn. You ask your ex-boss for an introduction, and suddenly, your outreach is framed as a trusted recommendation rather than a cold call.
That’s how you leverage your network, your 6 degrees. You become one with Kevin Bacon. That’s how you hustle smarter.
Part 3: Be Kevin Bacon
If– in the future– I ever have to make a cold call for my hustle… If I ever have to run an email sales campaign… I would shut her down. An act of mercy for me and that poor soul on the other end of that violence. I’m ready to get my first tattoo: Sooner cat food than spam.
This is Day 19, 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. Some humble bragging. I have 12K followers on LinkedIn and today’s exercise showed me that it means jack shit. I diligently did my network mapping and realized the massive chasm between a follower and a friend,
For instance, I searched for any first degree relationship with a title of Managing Director or greater and I got 100 pages of search results. And before you think I’m still bragging… Here's the polar opposite of a humble brag: in those 100 pages, I knew about 10 people well.
What can I say that I didn’t say on day 13– I suuuuuuuuck at networking.
Some more mind-numbing highlights of today’s analysis:
I validated that most of my senior connections are just followers, not people I’ve actually talked to or my much higher bar: having broken bread with. Most of my followers probably connected with me when I was regularly blogging on leadership on LinkedIn. And if I was desperate on the sales side, I could probably ask them for warm intros to a second degree connection (that’s first degree to them) but I’d probably have to explain to my follower who the hell I am first. So they’re there as a “resource”… and that’s only slightly better than a cold call. So, cat food.
What else? I validated that most of my real-world contacts are at big banks: either at JP Morgan, Bank of America, the Bank of NY and Wells. Makes sense. That’s 25 years of my day jobs.
What else? I know an unusually large number of people at Citi. Way more than I previously thought. And weird because I’ve never worked there. My guess is that Citi hires more than its share of ex-JP, ex-B-of-A, ex-BNY, etc…
Oh… and Goldman and BlackRock also kept coming up and I haven’t worked there either. My guess with those followers is that– unlike me– they’re just good networkers. That skill landed them there and they continue to exercise it.
None of this network mapping helps me yet. Because my content is giving me enough people to help. But I’m psyched that I did the exercise. All those connections are a kind of dry powder… for later… when I need a fire.
Ok… so let’s jump back to the day’s questions.
The first one was “How can you use research to make every email– every one-to-one email– feel like a face-to-face introduction?” The answer– isn’t “read my prospect’s LinkedIn. It’s “use LinkedIn the way it was meant to be used.” For network mapping. It can help you answer one of the hardest questions in sales– Who is the most credible person who could introduce you to a prospect… so you can go from a cold to a warm conversation.
Question 2 was: What would it look like for you to use your phone or email as a tool for service instead of marketing?
Again, you’re living the answer in its social media form. If I can validate with potential prospects that this content is useful to them– if I can get their permission to share it with them regularly– then I’ll repurpose it from post and blog to newsletter. That– by the way– is the whole point of the superserious mobile app– to funnel your social media followers into a platform you own so you can serve them, engage them, hug them and call them George.
I loved today’s MBA lesson because it was all about avoiding trust-killing sales tactics… by using my existing network for warm, credible introductions—a skill rooted in social network theory and widely taught in Ivy League MBA programs.
Now… go forth and build trust.
Prompt #1 - Make It Personal, Make It Powerful
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Prompt #1 - Make It Personal, Make It Powerful ○
Today, you’ll learn how to use email as a direct, high-trust channel to connect with your audience, nurture leads, and drive real growth-even if you’re starting with zero subscribers. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in digital marketing, customer relationship management, and persuasive communication:
- **Professor David Bell, The Wharton School, University of Pennsylvania:** Expert in digital marketing and customer acquisition.
- **Professor Jill Avery, Harvard Business School:** Specialist in customer loyalty, email strategy, and brand storytelling.
- **Professor Sheena Iyengar, Columbia Business School:** Authority on choice architecture and persuasive messaging.
**What Today’s Coaching Will Help You With:**
You’ll map out your first email sequence, learn the basics of segmentation and personalization, and discover best practices for building trust and driving action-so your emails get opened, read, and acted on.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **Who is the first audience you want to reach with your emails, and what do they care about most?**
- Think about your ideal customer’s pain points, interests, or goals.
2. **What is the one action you want your subscribers to take after reading your first email?**
- Is it to reply, book a call, download a resource, or make a purchase?
3. **What’s your biggest worry or hesitation about starting email outreach?**
- Be honest-whether it’s fear of annoying people, not knowing what to write, or tech overwhelm.
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### Step 2: MBA Skill – Email Sequence Design
Today’s MBA lesson is about designing a simple, effective email sequence that builds trust and drives action:
- **Welcome Email:** Introduce yourself, share your “why,” and set expectations for what’s next.
- **Value Email:** Offer a tip, resource, or story that solves a real problem for your audience.
- **Ask Email:** Make a clear, specific ask (reply, book a call, share feedback, etc.).
- **Follow-Up:** Gently check in if there’s no response-always with respect and value.
Keep each email personal, focused, and easy to act on. Segment your list if you serve different audiences, so each group gets what’s most relevant to them.
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### Step 3: Coaching & Action Plan
After you reply, I will use the writings of Professors Bell, Avery, and Iyengar to:
- Help you clarify your audience and the most compelling message for your first email.
- Guide you in mapping out your first 2–3 email sequence steps for maximum engagement.
- Suggest ways to personalize your emails and avoid common mistakes that kill trust.
- Offer tips for tracking open rates, replies, and conversions-so you can quickly improve your approach.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft welcome email or sequence idea.
- I’ll help you refine your email strategy, personalize your outreach, and suggest next steps for building your list and growing your impact.
- Remember: Email is still one of the highest-ROI channels in business-when you use it to build real relationships, not just blast promotions.
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Ready? Share your answers and email ideas below. Let’s hustle smarter, one lunch break at a time!
Secret Dessert Course
Ever feel weird about using “only 3 spots left!” or “ends tonight!” in your one-on-one emails? Every time I try to, it sets off my cheese-o-meter. Backspace, backspace, backspace….
The AI prompt below walks you through how to use “Ethical Scarcity & Urgency Phrases.” They help you motivate your audience to act-without the sleazy, high-pressure sales tactics that make everyone cringe.
It’s a real skill to use honest, transparent phrasing– i.e., “We’re limiting this to keep quality high” or “This offer is closing so we can focus on our current customers.”
The prompt will help you create a real sense of urgency that feels respectful, not manipulative. It’ll build trust, boost your credibility, and still get people off the fence– so you can grow your business with integrity and attract customers who actually appreciate your style.
If you want to nudge your audience without feeling gross, just copy and paste this next prompt into your favorite AI assistant to enjoy Day 16’s dessert.
Prompt #2 - Craft Ethical Scarcity & Urgency Phrases
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Prompt #2 - Craft Ethical Scarcity & Urgency Phrases ○
Today’s focus: mastering the art of ethical scarcity and urgency in your *one-on-one* emails-so you can encourage timely replies or decisions without sounding pushy, desperate, or manipulative. You’ll be coached by Ivy League experts in behavioral economics, business ethics, and persuasive communication:
- **Professor Eric J. Johnson, Columbia Business School:** Authority on behavioral economics and how urgency influences individual decision-making.
- **Professor Amy D. Sepinwall, Wharton School, University of Pennsylvania:** Specialist in business ethics and responsible, trust-building persuasion.
- **Professor Sheena Iyengar, Columbia Business School:** Renowned for her research on choice architecture and how to frame options for action in personal communication.
**What Today’s Coaching Will Help You With:**
You’ll learn to use scarcity and urgency phrases that are honest, clear, and effective in *one-on-one* emails-so you get more timely responses, decisions, or commitments, while building trust and professional rapport.
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### Step 1: Tell Us About Your One-on-One Email
Please answer:
1. Who are you emailing (role, relationship, and context: e.g., prospective client, collaborator, mentor)?
2. What is the main action or decision you want from them (e.g., reply, schedule a meeting, confirm a decision)?
3. What is your real deadline or reason for urgency (if any)?
4. (Optional) What’s your biggest concern about using urgency or scarcity in a personal email?
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### Step 2: Ethical Scarcity & Urgency Coaching for One-on-One Emails
After you reply, I will use the writings of your Ivy League coaching panel to:
- Analyze your email context and goal to recommend specific, ethical scarcity/urgency phrases (e.g., “I have a few openings left this week if you’d like to connect,” “I’ll be finalizing the project list by Friday, so please let me know if you’re interested,” “This opportunity is limited to the first three collaborators who reply”-but only if true).
- Help you craft transparent, non-manipulative language (Sepinwall) that sets clear expectations and avoids pressure.
- Suggest ways to highlight real timelines, limited availability, or exclusive opportunities-without exaggeration (Johnson).
- Guide you in balancing urgency with respect, so your request feels motivating and professional, not pushy (Iyengar).
- Provide 2–3 sample follow-up lines or closing phrases you can use or adapt.
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**How to use this prompt:**
- Respond with your one-on-one email details above.
- Your coaching panel will return a step-by-step guide to writing ethical, effective urgency and scarcity phrases for your unique situation.
- You’ll leave with actionable, MBA-level language that boosts your response rate and strengthens your relationships.