In this episode of the Control or Be Controlled podcast, host Darlington interviews attorney and founder strategist Sherri Prince. Prince explains how entrepreneurs should merge estate planning with business strategy to create a protective moat around their assets. She emphasizes the importance of reverse‑engineering an exit plan from day zero, tailoring legal structures (LLC, corporation, trusts) to the specific business model, and anticipating future goals such as sale, generational transfer, or retirement. The conversation covers common pitfalls that emerge as companies grow: lack of partnership agreements, leadership bottlenecks when founders operate within the business, and how rapid expansion magnifies existing operational weaknesses. Prince outlines warning signs that a company has outgrown its original legal entity—plateauing revenue, rising expenses, and inadequate systems. She offers a concrete first step for founders: ensure personal estate documents (will, trust, healthcare directives) are in place so business interests can be transferred smoothly. The episode concludes with resources for listeners, including Prince’s Play Big Faster video‑first podcast, quarterly free webinars, her upcoming book (October 2026), and her website and LinkedIn for further engagement.
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Hello guys, welcome to another exciting episode on Control or Be Controlled, a podcast designed to help you start thinking differently and take control of your life. And I remain your host, Darlington. Today's guest is Sherry Prince. Sherri, welcome to the show.
Thank you so much for having me. I'm looking forward to our conversation.
All right, Sherri, I would like you to introduce yourself to my audience.
Sure. So my name is Sherri Prince, and look, I'm a little hoarse today. Um, I'm an attorney and founder strategist. I help entrepreneurs merge their estate plan with their business plan to build a moat around their assets.
All right, thank you so much. That was quite a very, very brief introduction. So I don't know if I should add a little more to that, or we should just go into the questions that I have for you. So she specializes in ownership, governance, succession, and exit planning, working at the intersection of business strategy and estate design. She helps founders make smart legal and structural decisions today that protect their business through growth, partnership, partnership changes, disability disputes, or an eventual sale. She's also the— she's also the host of the Play Big Faster podcast, where she interviews founders and industry leaders about business growth, leadership, and the trends shaping entrepreneurship. Once again, Sherri, welcome to the show.
Thank you so much.
All right, Sherri, tell us, uh, what changes legally and structurally the moment a business becomes successful and visible?
Okay, so look, let me start by saying that even before we look at success— day zero, not day one, but before we open the doors— um, we need to anticipate things like how we intend to exit. Because all the changes that get us to where we're trying to go to, to reach that success, in my opinion, need to be reverse engineered. So some people purchase a business or build a business from scratch with the intention of never selling that business or never exiting. They may have a plan to pass that to the next generation. Well, in order to monitor success and to grow towards success, you need to figure out what that plan looks like. Is that plan death, which means you're going to be there until they roll you out? Do you plan on selling it? And I know in the tech industry, there's a great example of how you have so many tech founders that have a plan for 5, 7, or 10 years down the road to have a 7 or 8-figure exit. Mm-hmm. So what they do, they figure out where's there a gap in the market or is there something that's already working and it's doing great? And they take that company and they get it until they can get multiples of the value of the company. So you have to be very intentional. Your question was about success. Also looking at what does success look like for you? You know, everybody, every retail store doesn't desire to be Target or Old Navy or some big box store. You know, you may be satisfied being the mom and pop that is the location that people come to when they come to your hometown. So a lot of it's relative, but you have to, even before thinking about what success looks like, reverse engineer that exit so that you have those benchmarks.
So partnership conflicts often seem to emerge during periods of rapid growth other than at the beginning. Why is that the case? It's almost as if when the business begins to grow, they start having issues, but when So at the beginning stage, there were no issues.
Yeah, sometimes they're just, you know, you may have a partnership that may have started, you know, over the kitchen table with a friend. Hey, let's go into business together. Um, and there may not be formalities. Maybe there's no buy-sell agreement, no partnership agreement, nothing that memorializes what happens in the event you guys disagree. If you want to sell, maybe you don't want to sell the whole company, but maybe you want to sell your interest in the company. And if there are 2 of you or an even number of partners, what does a tiebreaker look like? You know, what things cause a default or a breach? How much time to cure that breach? Is it material or immaterial? So you have all these things that when you start your business, you may not consider because maybe you didn't go to an attorney, maybe just did it on a handshake. So that's why in the beginning, you know, Just like when you marry somebody, the person you marry is not the person that you divorce. So when you start a partnership and things are relatively new and small, you don't think about these things. But as you grow and the decisions become more complex, that's when you really start to consider, wow, you know, we didn't consider that. And now we just, we can't see eye to eye. So what do we do? And hopefully the answer is not call the attorneys. You know, hopefully you can get it worked out, but a lot of it is from the beginning not having a plan in place to address disputes, because the plan is not always going to solve the issue, but it will give you a mechanism on how to approach the issue to get to a resolution that will allow your business to continue to work and continue to grow, even in the midst of the confusion.
Okay, thank you so much. So, Why do some companies fracture under pressure while others become stronger and more unified?
A lot of it has to do with leadership. You know, believe it or not, like, these are not robots at the helm of these companies. These are people. So if you have a company that does not have strong leadership, um, a company that does not have the ability to pivot, you may have a company where the founder is not just the founder and the owner, but he's an operator. So he's working in the business day to day versus working on the business. So you need to, you know, you need to look at that as core. If you have the owner who's working in the business as an operator, and he may be the bottleneck, every decision has to come through here, through him or her. Every approval has to come through them. What does that look like if that person dies? become incapacitated, or just disabled and unable to take care of the day-to-day functions, is there enough continuity in that business for the business to survive? And when we say survive, I don't just mean survive, I mean also thrive, because you have to consider your investors, your clients. Are you going to be able to make payroll? Is what you contributed to the company essential? And is it something that your other partner, if you have a partner, can pick up on until you get back. And in the event that you're not coming back, what is the plan for that?
All right, uh, thank you, Sherri. So, uh, we often say expansion amplifies existing weakness— weaknesses instead of creating new ones. What do you mean by that?
Could you repeat the question, please?
We often say that extensions, they amplify, uh, hidden weaknesses or already existing weaknesses and not just create new ones. What do you mean by that?
Yes. So if you are already not doing something well, like for instance, say for instance, you do not have a CRM. I mean, yeah, CMR. And now your clients have gone from 50 to 500 and you were already not managing 50 clients very well, that's going to be even more exposed because your customer service is going to suffer, your sales may suffer, your logistics may suffer, and your distribution may suffer because you have something that was already hanging on by a thread. And once the— when the problem was smaller, you were able to patch it. Okay. And maybe it was not as noticeable, but as you grow, it's going to be amplified and it's going to be harder to patch. So things like that, when you're small, can easily kind of be looked over and then even the urgency to fix it. While you have the 50 customers, that may not be high on your list, but now you are 10x where you were and now you can't ignore it. Well, so not only do you have logistics, sales, operations, and all these other problems, do you have the financial wherewithal to go in and fix the problem that now is first and foremost before you. So that's the other issue.
Okay, so moving on. Many founders focus on building the business but rarely think about succession or exit planning. When should those conversations actually begin?
Yeah, they have to— like, when you're talking about starting the business, you should also be looking at, looking at what an exit looks like. Let's talk about Um, founders who may have a partner who are at different ages and different stages in life. You know, one of us may be thinking retirement looks like 55, and the other one may be thinking retirement looks like 75. So, you know, what are our individual goals? What is the mission for the company? And based on that, and when I would like to exit, How do we do this in a way that our company is not disrupted and that the partnership can live through that, survive that? And once one of us or both of us decide to, to leave, you know, what does that look like? So that is very much something to consider.
Okay, so what's the biggest mistake that you see entrepreneurs— legal mistake you see entrepreneurs make during their growth
The biggest mistake that I see them make during their growth stage is trying to solve a temporary problem with a long-term solution.
No, Sherri, I said the biggest legal, legal mistake.
Oh, okay. The big— oh, the biggest legal mistake is that they have not considered prior to this growth and expansion what that looks like in terms of their structure. You'll have so many founders who will just go and in the States they'll open up an LLC. Okay, and everybody thinks that LLC is one size fits all for their business, but depending on what type of business you have, that may not be the best structure for you. And if you are considering like maybe taking payroll, having employees, and depending on whether you are a company that is public-facing or you require anonymity. And if you are service-based versus you're selling products, there are so many things to consider. Even though your legal status does not automatically give you tax protections, there are some legal entities that can also have tax benefits. So one of the very biggest legal issues is not considering everything that you're doing and all your business activities and having some negative tax consequences because you chose the wrong legal entity.
Okay, Sherry, so what are the first warning signs that a business has outgrown the structure it was originally built on?
So when you start growing, you would hope that your revenue increased, but as you start growing, You have the need to grow, you need more equipment, more people, but your revenue numbers start decreasing. And that tells me that you don't have— that you're not optimized, that you don't have your systems in place. It tells me that maybe you are not doing tax planning. Maybe all your accountant is doing is preparing your taxes. And when you prepare taxes, that's like looking in the rearview mirror versus looking forward. So, you know, as you grow, if you're kind of at a plateau— and I'm talking about growing in size, um, in expenses but not in revenue— so that's one of the main things that I see.
All right, uh, so here's my final question for you. If every entrepreneur listening today could take one practical step this week to better protect their business, What would you recommend?
Yes. So I know you said to protect their business, but believe it or not, remember when we first started, I said that I help entrepreneurs merge their estate plan with their business plan to build a moat around their assets. You can't protect your business if you have not protected your life and your personal assets and the direction for your estate. So the very first thing you need to do, if you have not done this, or maybe you have and you just need to review it, Go and make sure that you have a will or trust, or you've properly designated the items that you want to go to other people by a transfer on death type designation or beneficiary on death designation, so that if something were to happen to you, all of your business interests can be properly assigned to the person that you would like to have an interest in your business. Also, in doing that, if you don't have a living will, a healthcare, or any sort of healthcare directive, um, or healthcare power of attorney, then you need to make sure that you have that in place so that someone can speak for you if you become incapacitated. Because if you're not personally taken care of, you cannot take care of your business.
That's right, Terri. Thank you so much. Thank you for sharing your expertise. and helping us understand that building a successful business isn't just about growth, it's about creating the right legal and structural foundation to support that growth for years to come. So, uh, you had a pod— you have a podcast, Play Big Faster Podcast. So for those that would like to learn more about your legal work and your podcast, how can they do that?
Oh sure. Um, the best way to find out information about the podcast, we're on YouTube. We're a video-first podcast, and you can check us out there at Play Big faster. And if you want to connect with me, the best place is LinkedIn. I love chatting with people about business stuff, and I offer a free webinar once a quarter. You can find that at cherrieprince.com, S-C-H-E-R-R-I-E-P-R-I-N-C-E dot com. And lastly, um, Darlington, I am writing a book that will be out October 2026. So a lot of what I talked about today is in the book. It's— and it's not a legal manual. I mean, anybody can read it and you'll be done over a weekend, but you'll have a lot of great tips and tools for your business.
All right, thank you so much. Thank you. And thanks to all my audience as well. You guys are the reason why we do this. If you enjoyed this episode, subscribe, leave us a review, and share it with a fellow entrepreneur Or a business owner. Do not forget to check out Sherri's links and check out our podcast as well. Thank you all so much for coming, and you all do have a wonderful day ahead. Bye guys, thank you, Sherri.
