How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel) SB1721
The Stacking Benjamins Show
Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
4.4 • 2K Ratings
🗓️ 13 August 2025
⏱️ 62 minutes
🧾️ Download transcript
Summary
Ever wonder how to build a career, business, or financial plan that actually lasts — no matter what life throws at you? This week, we’re bringing you lessons from someone who’s done it for more than five generations. Cheryl McKissick Daniel, president and CEO of McKissick & McKissick, joins Joe and OG to share the strategies her family has used to overcome obstacles, land major deals (like the arena in Brooklyn and countless buildings on the historic register of places), and turn connections into opportunities. Whether you’re growing a business, climbing the career ladder, or managing your money, you’ll walk away with practical ideas to strengthen your network, protect your reputation, and keep moving forward.
From the art of negotiation to turning big challenges into bigger wins, Cheryl offers insights you can use right now to build momentum. We’ll explore how revisiting your financial plan regularly can help you avoid surprises, why reputation is an asset you can’t afford to neglect, and how a strong team can take you further, faster.
Plus, we’ll take a break for our TikTok Minute to look at what happens when your vacation budget disappears in the name of “fun” spending. And in our headline segment, we’ll cover important Medicare and insurance updates that could save you money and headaches later.
Here’s what you’ll learn in this episode:
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How to use your reputation as a currency that opens doors and attracts opportunities
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Strategies for building a network that works for you (even when you’re not in the room)
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Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations
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Why regularly reviewing your financial plan can save you from costly surprises
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Smart adjustments to Medicare and insurance that protect your money and peace of mind
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How to turn adversity into momentum, whether in your career or personal finances
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A lighthearted look at how “just a little fun” can destroy your budget faster than you think
FULL SHOW NOTES: https://stackingbenjamins.com/story-about-building-america-1721
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
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Transcript
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| 0:00.0 | At some point far in the future, historians will probably ask, what was daily life like |
| 0:07.6 | in the early 21st century? |
| 0:10.6 | Well, one thing we know for sure. |
| 0:14.1 | Nobody will ever point to these two clowns and say, this was how you should have been stacking |
| 0:18.9 | Benjamins. This was how you should have been stacking Benjamin's. |
| 0:30.5 | Live from Joe's mom's basement, it's the stacking Benjamin's show. I'm Joe's mom's Neighbor, Doug, and on today's show, let's share a story you probably haven't heard. |
| 0:45.6 | The story of a black family who built America. |
| 0:49.3 | From the McKissick family of McKissick and McKissick fame, we welcome Cheryl McKissick Daniel. |
| 0:55.8 | I'm not sure if you caught that, |
| 0:57.7 | but that's the McKissick family, Joe. |
| 1:01.0 | Of the McKissick and McKissick fame. |
| 1:03.9 | In our headline segment, |
| 1:06.2 | Medicare benefits are a change. |
| 1:08.6 | What does that mean for your wallet? |
| 1:10.5 | We'll share. |
| 1:11.5 | Of course, we'll also share a TikTok minute, yet another headline, and way better |
| 1:17.0 | than everything I've mentioned so far, I'll also include, at no extra cost, my incredible |
| 1:23.0 | trivia. |
| 1:24.1 | And now, two guys who treat summer like their investment strategy, just winging it with sunglasses and fruity drinks, it's Joe and oh, jia, jujah, oh, I ran out of breath. |
| 1:37.2 | Gee, you just get on with it. |
| 1:39.9 | I said too many McKissick's. |
| 1:41.7 | I like, I have no breath left. |
... |
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