Afford Anything Podcast

Episode Title: The Hidden Information That's Costing You Money [GREATEST HITS]
Host: Paula Pant
Guest: Jeff Wetzler
Air Date: December 23, 2025
Theme: How mastering the art of asking for hidden information can dramatically improve your financial and professional outcomes, focusing on negotiation, feedback, and relationship-building through the “ASK” approach.

Episode Overview

This "Greatest Hits" episode, part of the FI/RE (Financial Independence/Retire Early) series, features negotiation expert Jeff Wetzler. The focus is the "first I"—Increasing Your Income—exploring how most people leave money and opportunities on the table by failing to ask the right questions and unlock hidden information. Jeff unpacks the art and science of asking for more in financial and everyday contexts—including job negotiations, business deals, feedback, and even used car buying—with a systematic five-step method called the "ASK" approach.

The conversation is rich with research, anecdotes, practical strategies, and actionable advice for anyone seeking to make smarter decisions, unearth buried insights, and build stronger relationships.

Key Discussion Points & Insights

1. What’s at Stake in Asking? (01:04–02:48)

Information: The undiscovered data and ideas others possess can change outcomes (“If we could actually find out the most important information that they are holding, we would make better deals together, we would make better decisions together.” – Jeff, 01:36).
Relationships: Asking questions not only uncovers information but deepens interpersonal connections. Stronger relationships improve business and collaboration.

2. The Illusion of Mindreading (02:48–04:13)

Research shows we greatly overestimate our ability to guess what others are thinking, even with close partners. The only reliable way to know: directly ask.
- "Even trained TSA agents at the airport know better than chance in terms of reading body language as well..." – Jeff (03:36)

3. Categories of Withheld Information and Why They’re Hidden (04:22–09:32)

Four Commonly Withheld Types:

Concerns and struggles.
Unexpressed true thoughts, especially if unpopular or controversial.
Feedback and suggestions for you (“If less than 3% of people are going to give us feedback about something we could just wipe right off... What percentage of people are giving us feedback about something much more high stakes?” – Jeff, 07:06).
Innovative ideas.

Why People Withhold:

Fear (of consequences, conflict, or relationship damage).
Difficulty articulating thoughts (mismatch between thinking speed and speech).
Lack of time or mental energy.
Assumption you don’t care or don’t want feedback.
- “They don’t think we are interested…” – Jeff (12:03)

4. The Five Steps of the ASK Approach

[1] CHOOSE CURIOSITY (13:05–14:23)

Curiosity is a choice, not just a trait. Center your intent on: “What can I learn from this person?” (13:17)
Genuine curiosity, not manipulation, is key for success.

[2] MAKE IT SAFE (14:23–19:40)

Reduce anxiety about sharing; trust and environment matter.
CEOs report the physical setting influences honesty (“I'm going to go where they want to go... wherever the other person feels comfortable...” – Jeff, 18:10).
Show vulnerability and reasons for asking to lower defenses.

[3] POSE QUALITY QUESTIONS (21:36–25:13)

Avoid "crummy" (leading, sneaky, multi-part, or attack) questions.
Quality questions help you learn something important:
- e.g., “How does that sit with you?” “What are you trying to solve for?”
Classic negotiation story: siblings fighting over an orange each want a different part (zest vs. flesh); deeper inquiry reveals win-win.

[4] LISTEN (29:04–37:16)

Most people overestimate their listening skills (“96% of people think they're good listeners, but in general we retain half of what someone else is telling us.” – Jeff, 29:10).
Listen for content, emotion, and actions.
Magic listening move: Paraphrase and reflect back, ask follow-ups, and allow silence.
- Doorknob moments: Important truths often come at the end (“So the actionable strategy is...just say to them, interesting. Say more about that, or what else?” – Jeff, 34:00).
Avoid “BS listening” (Back to Self), where you immediately shift the focus to your own story.

[5] REFLECT AND RECONNECT (37:40–43:03)

After gathering information, sift for most important points and turn them over in reflection:
1. Story (How does this change my understanding/situation?)
2. Steps (What actions should I take?)
3. Stuff (Deep internal biases, reflexes, or assumptions exposed by the exchange)
Reconnect: Let the other person know what you took away and how you’ll act on it. This increases trust and future openness.

5. Concrete Examples of the ASK Approach

Salary negotiation: expand curiosity beyond money (benefits, timing, titles, etc.).
Selling a couch (19:40–21:30): even single-issue deals can include delivery, sentimental value, or added flexibility.
Car buying simulation (43:03–58:31): illustrates how to surface hidden interests on both sides and how “multi-issue” negotiations differ from single-issue ones.

6. How to Use AI to Improve Your Asking and Listening Skills (59:01–64:47)

AI as a “brainstorming buddy for questions”; helps generate alternative perspectives, especially when feeling righteous or stuck (e.g., “What might I be missing?”).
AI can also help summarize transcripts (content, emotion, actions) for self-training in listening.
Creative use: ask AI for dream interpretations or deeper “stuff” reflection (“My wife tells AI her dreams and asks AI to interpret her dreams...” – Jeff, 64:25).
AI won’t replace essential human-to-human insight but can sharpen your skills.

7. Anyone Can Learn This (64:53–65:28)

“These are a set of very powerful human practices that I believe anyone can learn. I think we actually all have it innately in us because we were all kids once and kids are so naturally curious.” – Jeff (65:00)

Notable Quotes & Memorable Moments

On what’s really at stake:
"The stronger our relationships, the better we're going to be as partners when we do business together." — Jeff (02:27)
On feedback:
"If less than 3% of people are going to give us feedback about something we could just wipe right off... What percentage of people are giving us feedback about something much more high stakes?" — Jeff (07:06)
On curiosity:
"Curiosity is not just a trait that some people have and other people don't... It's an actual choice. And we can decide to be curious. And that choice is always available to us." — Jeff (13:14)
On quality questions:
"A quality question... helps us learn something important from someone else." — Jeff (21:36)
On listening:
"One of the most powerful ways…is simply to paraphrase back what someone is saying to you and check if you heard them right… It's like a magic listening move." — Jeff (31:43)
On the power of AI:
"AI can also help you literally to generate better questions...and they won’t all be perfect...but I can almost guarantee there will be two or three questions you never thought to ask." — Jeff (61:11)

Timestamps for Major Segments

01:04 — Introduce stakes and importance of asking for more
02:48 — The illusion of understanding others
04:22 — Four big categories of withheld information
07:06 — The “smudge experiment” on feedback
13:05 — Step 1: Choose curiosity
14:23 — Step 2: Make it safe (environments, vulnerability)
21:36 — Step 3: Pose quality questions (vs. crummy questions)
29:04 — Step 4: Listen (content, emotion, actions)
37:40 — Step 5: Reflect and reconnect (sift, turn, act)
43:03 — Car negotiation role-play (all five steps in a real-world scenario)
59:01 — How to use AI to improve conversation and reflection
64:53 — Final encouragement: Anyone can learn to ask better

Tone

Conversational, supportive, curious, and practical. Paula Pant and Jeff Wetzler combine expertise and down-to-earth storytelling to inspire actionable change for listeners who want to improve outcomes in money, work, and life by mastering the art of the ask.

For Listeners Who Haven’t Heard the Episode

This episode delivers a research-backed, step-by-step guide to discovering the hidden information that impacts your finances and relationships. You’ll walk away knowing:

The types of valuable information people rarely volunteer (and why),
Why curiosity, psychological safety, and question quality are critical,
How to listen far beyond basic comprehension,
How to integrate AI as a powerful tool in your negotiation and feedback processes,
And, most importantly, how to transform your approach for better financial, professional, and personal results.

If you’ve ever wondered how to get more feedback, negotiate more effectively, or just build better connections—this is your playbook.

Afford Anything Podcast

Episode Overview

The conversation is rich with research, anecdotes, practical strategies, and actionable advice for anyone seeking to make smarter decisions, unearth buried insights, and build stronger relationships.

Key Discussion Points & Insights

1. What’s at Stake in Asking? (01:04–02:48)

Information: The undiscovered data and ideas others possess can change outcomes (“If we could actually find out the most important information that they are holding, we would make better deals together, we would make better decisions together.” – Jeff, 01:36).
Relationships: Asking questions not only uncovers information but deepens interpersonal connections. Stronger relationships improve business and collaboration.

2. The Illusion of Mindreading (02:48–04:13)

Research shows we greatly overestimate our ability to guess what others are thinking, even with close partners. The only reliable way to know: directly ask.
- "Even trained TSA agents at the airport know better than chance in terms of reading body language as well..." – Jeff (03:36)

3. Categories of Withheld Information and Why They’re Hidden (04:22–09:32)

Four Commonly Withheld Types:

Concerns and struggles.
Unexpressed true thoughts, especially if unpopular or controversial.
Feedback and suggestions for you (“If less than 3% of people are going to give us feedback about something we could just wipe right off... What percentage of people are giving us feedback about something much more high stakes?” – Jeff, 07:06).
Innovative ideas.

Why People Withhold:

Fear (of consequences, conflict, or relationship damage).
Difficulty articulating thoughts (mismatch between thinking speed and speech).
Lack of time or mental energy.
Assumption you don’t care or don’t want feedback.
- “They don’t think we are interested…” – Jeff (12:03)

4. The Five Steps of the ASK Approach

[1] CHOOSE CURIOSITY (13:05–14:23)

Curiosity is a choice, not just a trait. Center your intent on: “What can I learn from this person?” (13:17)
Genuine curiosity, not manipulation, is key for success.

[2] MAKE IT SAFE (14:23–19:40)

Reduce anxiety about sharing; trust and environment matter.
CEOs report the physical setting influences honesty (“I'm going to go where they want to go... wherever the other person feels comfortable...” – Jeff, 18:10).
Show vulnerability and reasons for asking to lower defenses.

[3] POSE QUALITY QUESTIONS (21:36–25:13)

Avoid "crummy" (leading, sneaky, multi-part, or attack) questions.
Quality questions help you learn something important:
- e.g., “How does that sit with you?” “What are you trying to solve for?”
Classic negotiation story: siblings fighting over an orange each want a different part (zest vs. flesh); deeper inquiry reveals win-win.

[4] LISTEN (29:04–37:16)

Most people overestimate their listening skills (“96% of people think they're good listeners, but in general we retain half of what someone else is telling us.” – Jeff, 29:10).
Listen for content, emotion, and actions.
Magic listening move: Paraphrase and reflect back, ask follow-ups, and allow silence.
- Doorknob moments: Important truths often come at the end (“So the actionable strategy is...just say to them, interesting. Say more about that, or what else?” – Jeff, 34:00).
Avoid “BS listening” (Back to Self), where you immediately shift the focus to your own story.

[5] REFLECT AND RECONNECT (37:40–43:03)

After gathering information, sift for most important points and turn them over in reflection:
1. Story (How does this change my understanding/situation?)
2. Steps (What actions should I take?)
3. Stuff (Deep internal biases, reflexes, or assumptions exposed by the exchange)
Reconnect: Let the other person know what you took away and how you’ll act on it. This increases trust and future openness.

5. Concrete Examples of the ASK Approach

Salary negotiation: expand curiosity beyond money (benefits, timing, titles, etc.).
Selling a couch (19:40–21:30): even single-issue deals can include delivery, sentimental value, or added flexibility.
Car buying simulation (43:03–58:31): illustrates how to surface hidden interests on both sides and how “multi-issue” negotiations differ from single-issue ones.

6. How to Use AI to Improve Your Asking and Listening Skills (59:01–64:47)

AI as a “brainstorming buddy for questions”; helps generate alternative perspectives, especially when feeling righteous or stuck (e.g., “What might I be missing?”).
AI can also help summarize transcripts (content, emotion, actions) for self-training in listening.
Creative use: ask AI for dream interpretations or deeper “stuff” reflection (“My wife tells AI her dreams and asks AI to interpret her dreams...” – Jeff, 64:25).
AI won’t replace essential human-to-human insight but can sharpen your skills.

7. Anyone Can Learn This (64:53–65:28)

“These are a set of very powerful human practices that I believe anyone can learn. I think we actually all have it innately in us because we were all kids once and kids are so naturally curious.” – Jeff (65:00)

Notable Quotes & Memorable Moments

On what’s really at stake:
"The stronger our relationships, the better we're going to be as partners when we do business together." — Jeff (02:27)
On feedback:
"If less than 3% of people are going to give us feedback about something we could just wipe right off... What percentage of people are giving us feedback about something much more high stakes?" — Jeff (07:06)
On curiosity:
"Curiosity is not just a trait that some people have and other people don't... It's an actual choice. And we can decide to be curious. And that choice is always available to us." — Jeff (13:14)
On quality questions:
"A quality question... helps us learn something important from someone else." — Jeff (21:36)
On listening:
"One of the most powerful ways…is simply to paraphrase back what someone is saying to you and check if you heard them right… It's like a magic listening move." — Jeff (31:43)
On the power of AI:
"AI can also help you literally to generate better questions...and they won’t all be perfect...but I can almost guarantee there will be two or three questions you never thought to ask." — Jeff (61:11)

Timestamps for Major Segments

01:04 — Introduce stakes and importance of asking for more
02:48 — The illusion of understanding others
04:22 — Four big categories of withheld information
07:06 — The “smudge experiment” on feedback
13:05 — Step 1: Choose curiosity
14:23 — Step 2: Make it safe (environments, vulnerability)
21:36 — Step 3: Pose quality questions (vs. crummy questions)
29:04 — Step 4: Listen (content, emotion, actions)
37:40 — Step 5: Reflect and reconnect (sift, turn, act)
43:03 — Car negotiation role-play (all five steps in a real-world scenario)
59:01 — How to use AI to improve conversation and reflection
64:53 — Final encouragement: Anyone can learn to ask better

Tone

For Listeners Who Haven’t Heard the Episode

This episode delivers a research-backed, step-by-step guide to discovering the hidden information that impacts your finances and relationships. You’ll walk away knowing:

The types of valuable information people rarely volunteer (and why),
Why curiosity, psychological safety, and question quality are critical,
How to listen far beyond basic comprehension,
How to integrate AI as a powerful tool in your negotiation and feedback processes,
And, most importantly, how to transform your approach for better financial, professional, and personal results.

If you’ve ever wondered how to get more feedback, negotiate more effectively, or just build better connections—this is your playbook.

[I] The Hidden Information That's Costing You Money [GREATEST HITS]

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Summary

Afford Anything Podcast

Episode Overview

Key Discussion Points & Insights

1. What’s at Stake in Asking? (01:04–02:48)

2. The Illusion of Mindreading (02:48–04:13)

3. Categories of Withheld Information and Why They’re Hidden (04:22–09:32)

Four Commonly Withheld Types:

Why People Withhold:

4. The Five Steps of the ASK Approach

[1] CHOOSE CURIOSITY (13:05–14:23)

[2] MAKE IT SAFE (14:23–19:40)

[3] POSE QUALITY QUESTIONS (21:36–25:13)

[4] LISTEN (29:04–37:16)

[5] REFLECT AND RECONNECT (37:40–43:03)

5. Concrete Examples of the ASK Approach

6. How to Use AI to Improve Your Asking and Listening Skills (59:01–64:47)

7. Anyone Can Learn This (64:53–65:28)

Notable Quotes & Memorable Moments

Timestamps for Major Segments

Tone

For Listeners Who Haven’t Heard the Episode

Summary

Afford Anything Podcast

Episode Overview

Key Discussion Points & Insights

1. What’s at Stake in Asking? (01:04–02:48)

2. The Illusion of Mindreading (02:48–04:13)

3. Categories of Withheld Information and Why They’re Hidden (04:22–09:32)

Four Commonly Withheld Types:

Why People Withhold:

4. The Five Steps of the ASK Approach

[1] CHOOSE CURIOSITY (13:05–14:23)

[2] MAKE IT SAFE (14:23–19:40)

[3] POSE QUALITY QUESTIONS (21:36–25:13)

[4] LISTEN (29:04–37:16)

[5] REFLECT AND RECONNECT (37:40–43:03)

5. Concrete Examples of the ASK Approach

6. How to Use AI to Improve Your Asking and Listening Skills (59:01–64:47)

7. Anyone Can Learn This (64:53–65:28)

Notable Quotes & Memorable Moments

Timestamps for Major Segments

Tone

For Listeners Who Haven’t Heard the Episode