How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel) SB1721

11 snips

Aug 13, 2025

Cheryl McKissick Daniel, President and CEO of McKissick & McKissick, shares her family's remarkable journey in construction, emphasizing entrepreneurship across generations. She reveals strategies to turn challenges into opportunities, highlighting the value of reputation as a currency in networking. Cheryl discusses the importance of adapting financial plans and building strong teams to succeed. With insights on negotiation and resilience, listeners gain practical advice to thrive in their careers and businesses while navigating life's unpredictabilities.

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ANECDOTE

Two-Century Family Origin Story

Moses McKissick I started the family's building trade in 1790 after being taught brickmaking while enslaved.
That skill and location helped the McKissicks sustain a construction business across five generations.

INSIGHT

Why Multi-Generational Survival Is Exceptional

Passing a business through multiple generations is rare and exponentially harder at each stage.
The McKissicks beat the odds by combining craft, local ties, and adaptive strategy over generations.

ANECDOTE

Mother Took Over And Won Clients

Cheryl describes her mother taking over the firm when her father became ill despite minimal construction experience.
Her mother fixed the firm's mistakes and won clients by prioritizing integrity and hands-on problem solving.

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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:

How to use your reputation as a currency that opens doors and attracts opportunities
Strategies for building a network that works for you (even when you’re not in the room)
Lessons from landing multi-million-dollar deals — and how to apply them to your own negotiations
Why regularly reviewing your financial plan can save you from costly surprises
Smart adjustments to Medicare and insurance that protect your money and peace of mind
How to turn adversity into momentum, whether in your career or personal finances
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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