Would You Spend 2 Years In Jail For $20 Million?
Social Proof Podcast
Social Proof Network
4.9 • 2K Ratings
🗓️ 28 May 2026
⏱️ 40 minutes
🧾️ Download transcript
Summary
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In this episode, David and Donni dive into real conversations around money, entrepreneurship, risk, freedom, and the psychology behind financial decisions. From “Would you spend 2 years in jail for $20 million?” to “Would you rather make $500K working from home or $1M in the office?” — David asks a series of wild “This or That” questions that force you to really think about how you view money and success.
They also break down:
Fear vs confidence when investing money
Why some entrepreneurs never leave their jobs
Paying cash vs financing property
The mindset behind high income skills
Contractor vs employee culture
Money trauma, foreclosure, and financial freedom
The book “Happy Money” and how your beliefs affect your bank account
This episode is packed with entrepreneur mindset gems, honest stories, and deep conversations about wealth building.
👇 Leave your answers in the comments:
Would YOU take 2 years for $20 million?
Would you choose $500K from home or $1M in-office?
Pay cash or finance?
Subscribe for more conversations on entrepreneurship, money, business, mindset, and financial freedom.
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Transcript
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| 0:00.0 | We had already made seven figures before they quit their job, but it was the, it was like they were still connected mentally to the thought of, what if something happens with this and we have insurance. |
| 0:11.7 | I'm like, you're making seven figures. You can go and get the insurance plan. |
| 0:16.2 | Would you spend two years in jail for $2 million? |
| 0:18.9 | There was a version of me that would have done it for $500,000. |
| 0:22.6 | $500,000 a year working from home or a million dollars a year going into the office five days a week, nine to four. |
| 0:30.0 | She could make $100,000 in a week or a month or something like that, and then she'll just stop. |
| 0:34.9 | She'll take her foot off the gas because she feels guilty |
| 0:38.0 | about making too much money. And then there's somebody who settles for just enough money. |
| 0:45.5 | All right. Let me get my questions. I got questions for you. You have questions for me. |
| 0:49.7 | Yeah. Okay. Okay. So would you rather, would you rather spend two years in jail? |
| 0:58.5 | Okay, okay, no, no, no. |
| 0:59.6 | Jesus Christ. |
| 1:01.3 | So I'm going to ask the question, and I want y'all to answer in the comments. |
| 1:05.4 | But I'm going to ask you this question. |
| 1:06.5 | I know your answer, but then I'm going to ask another question around that. |
| 1:09.6 | Okay. |
| 1:10.7 | Two years in jail around that. Okay. Two years in jail, |
| 1:13.8 | okay, would you spend two years in jail for $2 million? No. Okay. I know why you're saying that. |
| 1:25.1 | Let me change it for you. Okay. Two years in jail or $20 million. |
| 1:29.3 | No. |
| 1:30.3 | Okay. |
| 1:31.3 | I know why you're saying that. |
... |
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