For Mackey McNeill, owning her own business always seemed like the obvious choice. After many successful years of helping companies make better business and financial decisions, her daughter Sarah Grace joined the team, and the mother-daughter duo entered the world of family business. While this transition was not without its hardships, Mackey and Sarah Grace were able to employ introspection, as well as outside tools and advisors, to better understand not only the business but also each other.

Following the success of her own family business, Mackey decided to share her knowledge in a practical and accessible way through her new book The Prosperity Playbook. For Mackey, prosperity is about more than just having money; it’s about living your passion day in and day out, and understanding finances is a key part of this idea. With this book, she aims to provide concrete steps that family businesses can take to discuss finances in a way that eliminates the taboo surrounding the subject and boost their chance of success during succession.

In this episode of WiFB Conversations, Mackey McNeill and Ramia Marielle El Agamy discuss the importance of understanding finances, how to encourage a successful succession and what family businesses can do to survive during global economic crises.


R: Early on in your life, you were very clear that a Fortune 500 career was not going to be your path. What about it made you decide to build your own enterprise and end up in a family business?

M: I was in my twenties when I started my own business. Even before that, I only worked for small companies because my friends who tried to recruit me would always ask me to work for them.

I’d interviewed at several companies, but the layers of structure just didn’t appeal to me. In fact, a friend of mine even said, “You just have to brown-nose your way to the top.” Knowing the right people and political posturing just had no appeal to me.

My husband used to say to me, “You’re an entrepreneur at heart, Mackey. Get over it, and just go do it.” He was so right. I have a lot of creativity and desire to put my own thoughts, feelings and brands on things. So, he was absolutely on target. I needed to do my own thing.

R: Your career has evolved enormously, especially when you turned this into a family business. Tell us more about the actual business that you started out building.

M: I started out building a firm that was designed to help business owners be more prosperous. I had no idea what that meant or how I would do it. I had a degree in accounting, a CPA certificate and some experience working with small businesses. But there wasn’t a format that I could follow.

I talked to small businesses and asked them what problems they were having and what they needed in the area of finance. Things were going really well, and I was getting more business and gaining some traction.

Then, my husband quit his job.

Sarah Grace was three at the time, and our agreement was that he would stay the primary breadwinner until she was five and in kindergarten. We weren’t ready for him to quit, but he was ready.

I bought a CPA firm and thought making money enough money to pay the bills in the family household was a good idea.

My goal switched from purpose-driven concerning the companies I was serving to taking care of my family, and I was successful. I built a very nice CPA firm, and it became one of the largest CPA firms in greater Cincinnati, Ohio.

I was doing very well, winning awards and getting accolades, when my husband committed suicide.

That put me through a spiral of inner reflection. I went through a lot of healing and therapy with my daughter. I have not experienced a lot of death in my family, but this was a time when I recognised that life is very short.

Here I was, running one of the largest CPA firms in Cincinnati, and I wasn’t having fun anymore because I wasn’t living my passion. For me, it was never just about the money, but somehow, I had become focused only on making money.

In a business, there are so many fires, and all you can do is put those fires out, go to bed and start over the next morning. I had gotten into that mode, and I decided to recreate myself.

I started selling parts of my CPA firm, and that gave me the capital to go back to where I started. I wanted to create a model of assistance for family business enterprises to help them succeed.

I always believed that many businesses are missing a good grasp of their financials. They may have a bookkeeper, so it’s not that they didn’t have the information. However, they don’t always know how to turn that information into something useful – some wisdom that they could extract to make good decisions.

That is missing from 90 per cent of small businesses, but there was no system to give them that wisdom. Luckily, I’m a systems-oriented thinker.

So, I decided to put a system together. Over the years, I have had wonderful clients who let me try things with them. If it worked, I tried it on other clients.

This business has evolved into what we now call a financial operating system that comes with a coach, and that system is called Prosper for Business. It’s very transformational for family businesses.

The Prosperity Playbook: Understanding Finances within the Family Business
Image courtesy of Mackey McNeill

R: When your husband committed suicide, it must have been such a difficult but transformative time that changed how you define family. I’m interested in understanding your perspective a little more.

You talk about healing and moving towards purpose-driven activities. It’s interesting that you felt such a strong appeal from the family business side, where these typical issues crop up. A lot of families face these problems, including mental health issues and conflict, which can affect people’s happiness. In spite of having lived through this trauma, you were still attracted to helping families who deal with these issues.

Tell us how the psychology of how that functioned in your mind. Why did you move towards that rather than away from it?

M: I was born with a yearning for family. I was adopted at birth, and I met my birth family when I was 38. There’s something about growing up as an adopted child, especially in a closed adoption, where you’re not allowed to know anything about your heritage, that creates a constant yearning.

Having a child of my own was a big piece of that, and having my own family was a huge deal for me. Then, I lost a cornerstone of my family through death.

At that point, I’d already worked with small businesses one-on-one for 15 years. They’d tell me about their problems and dynamics, such as paying a family member who’s doing the bookkeeping as if they were the CFO. I saw these interweaving conflicts and unspoken commitments, and I wanted to help businesses manage them.

The business itself often can’t financially overcome these personal obligations of family, especially when the business is dying or struggling. The need to keep everybody employed and not speak the truth of what they were contributing to the business is really difficult.

I eventually started studying the Enneagram, and I became a certified Enneagram teacher. At some point, I decided that I knew enough about money and wanted to know more about people. I wanted to have transformational conversations with people around finance, and there are two elements to that conversation – money and people.

I had to know more about people, and this frame of reference that I developed from learning about the Enneagram was incredibly healing for me. I began to use it with clients to understand them, and I even offer it to them. I give them a little book and tell them how helpful it has been for me.

I can see more about their struggles from that frame of reference. It’s very helpful, and my entire team is trained in it. Everybody on my team has that perspective when they start working with a new client.

R: There are a lot of systemic approaches to confusing and emotional challenges that we face in the family business. For those inside the family business, these can be hard to look through. Having third-party advisories is absolutely essential for survival.

What’s interesting about your situation is that your business eventually turned into a family business when Sarah Grace joined you. Let’s talk about that moment of truth. You’ve suddenly gone from advising businesses on how to deal with relatives and finances to confronting your own relative in the business.

What was that like for you when Sarah Grace joined the team? What phases did you go through during that transition?

M: We had three primary phases.

The first phase was when her father died. I was a single mom, and I needed to be around her more, so I had her work at the office, not by her choice but by mine. In those days, she would come in and file papers. That allowed us to be closer together, and I could keep an eye on her and know where she was.

Then, she left to get “a real job,” as she called it, when she was in high school.

Later on, her college education was disrupted. She’s like me, and she has a lot of interests. She would try something for a while, and then she would decide that it wasn’t for her.

At one point, she was in between what she was studying at college, and I had an available job for her. I knew it was temporary, but I had hoped that she would take it and run with it. However, she left eventually to go back to school and take another job.

I remember someone asking her what it was like to work for her mother. She said, “It was terrible. I hated working for my mother.” I was just devastated. I didn’t think it was awful, but that’s her truth, and I honour everybody’s truth.

A few years went by, and I had a part-time marketing position that was just perfect for her. She was between what she was doing, and she wasn’t in college full time, so I called her and told her about the job.

I had already found someone I wanted for it, but it kept nagging at me that she would be so good at it. I said, “If you want the job, it’s yours. But you have to call me before nine o’clock tomorrow. Here’s the pay, and here are the hours.”

She called me at 8:30 and said she’ll take it.

We definitely had our challenges during that first year. I felt like she needed to push against me. I don’t want to speak her truth, but there was often a level of upset that would appear out of what seemed like nowhere.

I can also be very focused on work. Even though I’m very curious about people, I know that I’m not always in tune with them. Sometimes, I’m just focused on work, and I don’t notice that I’ve hurt someone’s feelings.

R: Anyone working with family members understands the brutality of their perception of us. You really have to want to do this.

I always tell people that a family business is not for everyone. You’re going to have to hear things about yourself that you might not feel are true. However, you have to accept it as their truth, which is a hard thing to do, especially for a parent.

Sarah Grace has been with you for a long time and has done extremely well in the company. You’re working together very well and in harmony now.

How did that relationship progress? Once she came on board full time, did you do anything consciously to make sure that the relationship would evolve and get healthier, or did you just let it happen?

M: It was definitely a conscious effort on both of our parts. Because of what we’d been through together, we both had tremendous amounts of therapy.

Sarah Grace said to me one time that she didn’t want any more therapy because she’s not mentally ill. I said, “I think only sane people have therapy.”

Therapy is about understanding more about yourself. It’s so sad that we stigmatise therapy because it can be helpful, especially in times of great need. We learned a lot about ourselves, and we were challenged now to put that to work.

It’s one thing to know; it’s another to act. Now, we were in the business of acting.

She would come to me often and say that we were so far behind. However, I worked with small businesses every day, and I knew that our systems were not at the bottom of the barrel.

Two things happened. First, we began to learn to talk about the business in a different way, and we learned to talk about how we can move forward in areas where we can improve.

Second, she gained some experience with the small business centre. She began to circle with other people working in their family business, and she realised that we really had our act together.

It was helpful to have that perspective from working with small family businesses. The blessing of what I do is that I get to see a lot of their insights – not just their financial insights but their relationship insights.

Life is a process, and business is a creation. It’s a living system, and you have to treat it like a living organism. Just because you have some problems solved today doesn’t mean that they’re going to stay solved tomorrow. You have to have a system to keep it alive and working for you.

The other thing that was really transformational for us is that I put in an outside board of advisors.

As a mother, I can either wear rose-coloured glasses, or I can have glasses that are way too critical. I know enough about myself to know that sometimes I’m kidding myself. Sometimes, I don’t see the truth of what’s there.

I met with the outside board for three or four years. Their primary objective was to see how we work together to help us facilitate our relationship and how we communicate about the business.

I asked the Board to give me feedback on whether Sarah was ready to step. I had to get outside feedback because, in my head, the conversations ranged from “She isn’t ready” to “I am holding her back”.

That was transformational for me when all three of them told me that she was ready. I know that they weren’t doing it to make me happy. They definitely had the interest of the company in mind before anything else.  

They also worked directly with her as much as they did with me. They had a really good opportunity over the years to watch her and experience her progression.

The Prosperity Playbook: Understanding Finances within the Family Business
Image courtesy of Mackey McNeill

R: She’s doing such a lovely job now and is such a wonderful leader in her own right. I enjoyed our conversation enormously when we did the podcast with her. She’s such an insightful and kind person, and it’s lovely to see how that can lead to success in a business.

We’re often taught that you have to be shrewd and cunning. Sarah Grace is one of those people who proves that you can lead through kindness and get just as far. When you talk to women in business, it’s encouraging to see those qualities being rewarded.

There’s an old-fashioned notion that comes from a primarily-male working environment that certain hard qualities are the only way for a woman to build a career and be successful.

I was delighted to hear that you two finally sat down and put everything into a book. Tell us more about why you’ve decided to write this now. Why did now feel like the right time? How long ago did you realise that you wanted to do this?

M: This is actually my second book. About 16 years have passed between the first and the second one, and I think knowing how much work it would take affected when I wrote this book.

This book was in me for a long time, but I knew that once I started, I would have to finish. I’m a finisher, even though I knew I wouldn’t even want to look at it anymore by the end. After you write the book, you have to reread it, and you’re constantly refining it.

At some point, just like I did with my first book, I realised that if I’m going to write this book, I can’t keep it as a thought that I’m going to do someday. Like with anything I do, if I’m going to do it, I’m committed.

I booked myself two weeks in Puerto Rico on the island of Vieques in the middle of winter last year. I went by myself, and I got up every morning and wrote while looking at the Caribbean.

I would meet people, and they would ask me what I was doing there. Most everybody was on vacation, but I told them that I was writing a book. I event went to an event with my Airbnb host, and he asked me, “What makes you think anybody wants to read your book?”

Nobody had ever asked me that question, but it’s a really good question. He probably wouldn’t want to read my book because he’s not a business owner. It’s not for everybody. However, I think for business owners, there’s a lot of wisdom inside.

Writing in Puerto Rico was a good start. Then, I had to make a commitment when I got back of how many days a week I was going to write and stick with it.

R: That first hurdle was out of the way, and that first intense investment had been made. After that, you pushed it to the finish line, and you published it. It’s called The Prosperity Playbook: Planning for a Successful Family Business Succession.

There are a lot of words in there that I want to talk to you about because a successful family business succession does not happen easily.

Tell us more about what you set out to do with this book and what it brings to family businesses.

M: I have always been focused more on prosperity than I have been on money. If I have money, I may not be prosperous. However, if I’m prosperous, I have money.

Prosperity also includes your heart. Am I loving what I’m doing? Am I living from my inside out? A lot of those ideas are in the book.

One of the processes that we go through in our business is helping people figure out if they are living their passions and running their business in a way that fulfils them.

Why do something every day that you don’t love? That should be part of the conversation – not only how to enjoy yourself after work. The passion has to be there from the start.

Additionally, your finances cannot be separated from it. I see finances in a very holistic way. It’s not a separate aspect; it integrates everywhere. Your strategy and how you work in the business relate to your financial situation.

That’s the first piece of the title.

Next, it’s a playbook because it gives you step by step instructions. It includes the structures that you can put in place in your family business to help you communicate honestly, openly and concisely when you talk about money and finance, which is often the most difficult conversation you’ll ever have.

I have talked to many groups about money and finance. I met a woman once who said, “I have a group of women I’ve met with every week for my entire life. We talk about everything, including our intimate sex lives, but we never talk about money.”

Money is a taboo subject, and in a family, it ignites our emotions. We all have feelings about whether someone is making too much or too little. Those thoughts may or may not be rational, but they all get in the way.

We wanted to create a common tool of language around money and finance without teaching everybody how to be a CPA. That’s a big part of the book. How do we put information together that’s easy to understand, actionable and creates a decision-making capacity within the business so that people can see the finances in a collective way?

In other words, the person who’s more in tune with the finances shouldn’t be the only one looking at it. Everybody should be able to see the information, and they need to have common knowledge.

If we speak the same language and have common knowledge, we can get a lot further. That’s a big piece of the playbook aspect of the book.  

Next, I took a deep look at the clients I love working with the most, and they were all family businesses. However, I also think that if you‘re in any business, you’re in a family business.

Even if no family member works for you, your business is probably supporting your family, and your family is likely involved in your decisions. You don’t go home at night and think the day’s over; you go home and talk to your family about your day.

The Prosperity Playbook: Understanding Finances within the Family Business
Image courtesy of Mackey McNeill

R: The family makes sacrifices along the way as you build that business.

People always say that the next generation feels entitled to the business. However, if you’re the child of a founder, you’ve already paid into that business more than anyone will ever know. You’ve shared your parents’ attention with that business all your life, and that is a huge sacrifice that can either stimulate resentment or enthusiasm for the company.

M: Sarah Grace always says, “My mother has two children – the business and me.” It does take a lot of time and attention. I started my business from ground zero; you don’t start from ground zero and work a nine-to-five schedule. Her dad helped, as well, and we all sacrificed for it.

R: You managed to do what so many founders don’t.

We tend to dwell on the success stories of businesses. The truth of the matter is that there’s an enormous failure rate. Even if you have a great, charismatic founder, the succession is usually very hard for a variety of reasons.

Maybe the industry has become redundant or has been disrupted, maybe other family members are just not interested in continuing the business or maybe including them in the first place was a mistake. There are many reasons why a business can be challenged in terms of continuity.

You’ve purposefully included the word “succession” in the title of your book. Tell us a little bit more about why you accentuate this generational transition as part of what you’re trying to achieve for family businesses.

M: If you have a family business, you have an enormous family wealth asset that can serve future generations. However, you have to speak openly and with integrity about the dark subject of money and finance without getting your feelings hurt.

The statistics around succession are shocking. Only 30 per cent of businesses achieve a family succession, even though 70 per cent want to. The failure rate is intense.

Just like Sarah Grace is in a round table with her peers, I’ve served in round tables with my peers. If people don’t have good resources when it comes to the financial aspects, and they don’t deal with the underlying resentment that might be present around money, then everything is going to fall apart.

People often have unspoken requirements surrounding money. A gentleman in my CEO group had taken over from his dad. His dad just wanted his son to pay him his salary for the rest of his life. That was an enormous amount of money – much more than the company was worth.

They had unrealistic expectations, and the company wasn’t making enough. His dad had made progressively more money over time. He had ratcheted up his lifestyle, but he had not saved any money outside of the business, and the business had to continue to support that lifestyle.

A family succession is a leveraged buyout. If the business will not support the Generation One’s retirement requirements, the business fails and everyone loses. To win, all three entities – Generation One, Generation Two and the business – have to find a point where they can all be financially healthy, at the same time.

That’s an enormous challenge, and I love challenges. I love that intersection of people’s thoughts, feelings and emotions around money. I also love using my talents to put together a system that supports people and gives them communication tools. This particular challenge hits on all the elements that I feel passionate about in business.

R: This is one of the hardest things to talk about in the family. It often gets mixed up with other emotional histories that we might have with each other, and it even amplifies those issues. We have to figure out how to deal with that emotional threat hanging over our heads when talking about finances.

Right now, we’re in a global pandemic, but we’re also ringing in potentially one of the hardest economic crises the world has seen in a very long time. Many countries are experiencing a depression, which has not been seen in almost a century.

You’re in a great position based on your expertise in understanding what this can do for or to family businesses. What is your go-to advice for family businesses in the face of these problems compared to what you would normally suggest to them?

M: Some businesses have been shut down, and some businesses are busier than ever. Then, there’s a variety of truth in between those two spectrums.

Whenever there’s an economic crisis, our number one focus is cash. We have a lot of tools around managing cash, but we get much more aggressive about managing cashflow during crises like this.

Our first role with any company is to make sure that they have sufficient working capital and that they can manage themselves in difficult times.

Of course, I never imagined that businesses would have to shut up their doors tomorrow by executive order of the government. That’s a whole new paradigm, but we want to make sure that people have a cash flow and have access to any government resources that are available.  

You can have a great business plan, but if you don‘t have cash, you’re out of business. That’s the number one issue on which we focus.

Once we have the cash managed and we’re consciously forecasting our 16-week cashflow, we can move on to taking opportunities.

This is an incredible time of change, and whenever there’s change, there’s an enormous opportunity. If there is something that you have always wanted to try in your business, such as providing a new offer, packaging or pricing, this is the best time to try it.

People are expecting something new, so you can test different ideas to see if they work. I’ve had companies test new things that have become their new model. They’re more profitable now than they were under their old model because they were willing to try new things.

It’s scary, but this is definitely a time of opportunity. You have to look at it from a deeper level.

Technology is super important. How can you deploy more technology? Even if you’re in a retail environment, how can you reduce the touchpoints using technology? Anything you can do to focus on health and safety and be more compassionate with your customers is important.

Customers are changing their buying habits, and it’s important to look at what’s happening in the marketplace to be effective.

I’ve been doing a series of blog posts called “The Three R’s to Recovery.” It’s about reimagining people, reimagining structures and recovering revenue. It will include about 20 posts when it’s all put together with short ideas on how to re-engineer your business because I think this is the time to really rethink everything.

The Prosperity Playbook: Understanding Finances within the Family Business
Image courtesy of Mackey McNeill

R: We’re assuming quite a high level of emotional health in a business for that to be a possibility. What is true and proven about what you’re putting forward in this book is that this emotional health has a lot to do with financial health.

I know that this is an exceptional circumstance, but imagining and questioning yourself requires courage to confront issues that haven’t been confronted even in the best of times.

How do you bring that conversation to the table? How do you champion this conversation in your family business now that there is this window of opportunity?

M: One of the things I would suggest is finding an outside advisor. Unless your family already has a lot of tools around consciousness and reactivity, it’s important to find someone who can help with that.

We all have areas where we get stuck. That’s what I love about the Enneagram. It tells us where we fall into our own little pits of unconsciousness.

Unless everybody in the family has done a lot of inner work, you need someone from the outside to show you the reality.

I was just talking to a client recently who was struggling financially. They’ve been using the tools in the book for about three years now, but they had resisted getting started with us in the beginning.

When we finally had our first meeting, they said they felt like they’d been hit in the gut. It was difficult for them, but I don’t think they could tell the truth to each other because they didn’t know how to put it together in a way that they could see it.

How you put information together so that it’s very clear is important. We use a lot of graphics and pictures more than columns of data, which can be very difficult to wrap your head around. A picture is much easier to understand.

Once you see the truth and get past that initial awful feeling, it’s a relief. When people don’t know the truth about money, whatever they’re imagining is often worse than what’s really happening. It’s like opening that dark, scary closet, looking in and realising that it’s not nearly as scary as you thought it was going to be.

Having someone who’s not attached to the dynamics of the family to bring that truth is really important.

R: It can be a really key catalyst.

You can start by reading a great book, like The Prosperity Playbook by Mackey McNeill. We’re including the link below this podcast for everyone to check out on Kindle, hardcover and paperback. Hopefully, one day, you’ll record an audiobook of it, as well.

Thank you so much for coming on the conversation with Women in Family Business.

M: Thanks for having me. It’s been a delight and a pleasure to spend this time with you and to meet you in person.