Help Wanted – “How to Win People’s Trust”
Podcast: Help Wanted
Hosts: Jason Feifer (Entrepreneur Magazine Editor-in-Chief), Nicole Lapin (Money Expert)
Date: September 4, 2025
Theme: Unlocking one of the most essential skills in work and business: how to earn and maintain other people’s trust by diving deeper into “knowingness” in your communication and marketing.
Episode Overview
In this episode, Jason Feifer focuses on the art of communicating with “knowingness”—going beyond being specific and demonstrating deep, nuanced understanding of your audience’s real-life experiences and emotions. He breaks down strategies and real-world examples to show how “knowingness” builds genuine trust, whether you’re marketing a business, pitching ideas to your boss, or just trying to connect more powerfully with colleagues and customers.
Key Discussion Points & Insights
What Is “Knowingness” and Why Does It Matter?
- Three Levels of Communication:
- Generalities: Too broad/vague, fails to connect.
- Specifics: Clear and focused, often sufficient but not profound.
- Knowingness: The highest level—“When you say things that only your target audience would understand, displaying your deep knowledge of their needs.” (Jason, 03:13)
- Knowingness is demonstrating that you not only understand what people need, but why and how it feels to need it—creating “felt understanding.”
The McDonald’s Ad Example
- Jason recounts a favorite McDonald's ad from 2010, where a dad repeatedly circles a drive-thru, whispering his order to avoid waking his sleeping baby.
- The staff finally helps him get his food, showing McDonald’s awareness of parents’ real-life challenges, not just food needs.
- Insight: The ad connects on an emotional level, reflecting not just a generic problem (hunger), but the nuanced struggle of parents.
- “McDonald's didn't just show a hungry customer getting food. They captured a hyper specific challenge that every parent understands...” (Jason, 06:50)
- Highlights how the emotional experience of the ad draws people in and makes customers feel seen and understood.
More Examples of Knowingness
- United Card Ad:
- “If your vacation doesn’t start until their movie does, you should probably have a United card.” (Jason, 07:46)
- Speaks directly to parents’ lived reality on flights with kids.
- StreetEasy Subway Ads:
- Images showing “cool” New Yorkers looking lost in the suburbs with captions like “Never become a former New Yorker.”
- These capture the anxieties of city-dwellers afraid of losing their identity if they move to the suburbs.
- “I saw these and I texted them immediately to friends of mine who had made the move from New York to the suburbs.” (Jason, 09:15)
How To Cultivate and Communicate Knowingness
- Step 1: Hear Their Nuanced Complaints
- Talk to your audience, listen for what truly bothers them.
- Go beyond superficial gripes—dig for the things people would admit after “maybe two drinks in.”
- “It is personal, small, but also meaningful. It should make their peers say, ‘That happens to me too.’ That right there, that is the core of knowingness.” (Jason, 10:07)
- Step 2: Reflect Their Reality With Specificity
- Speak/write in ways that scream, “I know your problems at a granular level.”
- Triggers psychological “felt understanding”—people feel genuinely seen.
- Examples:
- “I help founders who lie awake at 3am wondering if they made the right decision about that product, while also feeling guilty for how tired they’ll be with their kids the next morning.”
- For busy executives: “...every time they leave the office before their team, even though they know they need boundaries to be effective.”
- For LinkedIn: “...the expert who knows they should be posting, but stares at a blank screen for 20 minutes before giving up...”
Personal Application: Jason’s Own Story
- When pitching himself for speaking gigs, Jason tells the story of “Gary,” a long-time company man who said:
- “In the decades I’ve been going to these things, I’ve seen a lot of speakers do empty cheerleading. But you’re the first one to give us practical, useful things to do. So I just wanted to thank you.” (Jason quoting Gary, 11:47)
- Jason uses this story to show he understands what executives and employees actually value—practicality, not flashy motivation.
- “Clients love when I say this. You know why? It's because it shows how well I understand their needs and it shows I can deliver.” (Jason, 12:08)
- Takeaway: Knowingness “closes the deal” by making people feel deeply, emotionally understood.
The Broader Impact
- Practicing knowingness doesn’t just help you sell or persuade—it makes you a better human.
- “We should never want to just sell stuff, we should want to make lives better, which means we need to know those lives. So listen closely, dig deep, communicate deeper. You have to live in the nuance.” (Jason, 12:55)
Notable Quotes & Memorable Moments
- Jason on the definition of knowingness:
“That is when you demonstrate that you don’t just understand what other people need, but you understand why they need it and how it feels to need it. When people see that from you, they trust you more.” (04:20)
- On the power of specificity:
“Your words should scream, ‘I know your problems at a granular level.’” (10:56)
- Story about Gary:
“In the decades I’ve been going to these things, I’ve seen a lot of speakers do empty cheerleading. But you’re the first one to give us practical, useful things to do.” (Jason quoting Gary, 11:47)
- On empathy in business:
“Help Wanted is a production of Money News Network… We should want to make lives better, which means we need to know those lives.” (12:55)
Important Timestamps
- 02:23 — Show begins, intro of hosts and show segments
- 03:13 — Jason introduces the idea of three tiers of marketing/communication
- 05:17 — McDonald’s “knowingness” ad breakdown
- 07:46 — “If your vacation doesn’t start until their movie does”—United Card ad
- 08:45 — StreetEasy’s “Never become a former New Yorker” subway ads
- 10:07 — Two-step process: hear nuanced complaints, reflect reality
- 11:47 — Jason’s keynote story about Gary and why it works
- 12:55 — Why knowingness makes you better at work and better as a person
Overall Tone
- Jason’s style is storytelling-driven, empathetic, and practical.
- The episode is supportive and actionable—full of specific tools, real-life examples, and memorable lines.
- Listeners are encouraged to approach communication (and business) from a place of deep understanding and respect for the other person’s lived experience.
Takeaway:
To win people’s trust—be it customers, colleagues, or clients—learn their world so well that you can echo back not just their challenges, but the subtle, personal feelings they have about those challenges. That depth builds true connection and trust—the heart of effective communication, leadership, and business.