Nicole Middendorf | The Team You Need to Propel Business Growth

As a financial advisor, Nicole Middendorf of Prosperwell Financial often feels more like a psychologist. She finds she has to change her clients’ mindset about money… and even gets involved in a sort of couples counseling.

We talk about that, as well as the roundabout career path that got her to where she is today, why she wouldn’t trade it, and what she learned along the way that she still uses in her current business. Plus, we talk about her refreshing take on the traditional “bucket list.”

Tune in to find out…

  • The first employee you should hire
  • What should be the ultimate goal for every business owner – that has nothing to with money
  • How your spouse should be involved in your business
  • Why driving a race car in Las Vegas had a huge impact on her business
  • And more

Listen now…


Mentioned in this episode:



Steve Gordon: Welcome to the Unstoppable CEO Podcast. I’m your host, Steve Gordon, and today I’m really excited for this interview. I am speaking with Nicole Middendorf. She’s a wealth advisor and she’s the CEO of Prosperwell Financial. In addition to that, she’s got a whole host of other things that she does. She’s a published author, a speaker, a frequent guest on all kinds of media, publishes all kinds of information through her website, and has a podcast of her own. Her goal is to help others, whether it be with their money or finding what truly makes them happy, and she’s built really a very interesting and very fast growing business. I’m excited to have her here.

Welcome, Nicole, to the Unstoppable CEO.

Nicole Middendorf: Thank you. Thanks for having me.

Steve Gordon: Yeah. I’m excited to dive in. Give us a little bit of background. I know you’re based up in Minnesota, in Minneapolis, but give us a little bit of background on you and your business so that listeners can understand where you’re coming from.

Nicole Middendorf: I never planned to be a financial advisor. I wanted to go to law school and be like Madeleine Albright or be like Ruth Bader Ginsburg. I wanted to work for the UN and make change. I had some money. I started working when I was 10. When I turned 16, I had some money, and I would hear my parents on the phone talking about Microsoft stock and Intel stock. I went to my mom and I said, “Mom, I want to invest.” She’s like, “Oh honey. You have to have $100,000 to invest”, and so I didn’t. I took the $10,000 that I’d accumulated by the time I was 16 and I used it to study abroad. There’s no price tag that you can put on studying abroad, that was just an amazing experience, but all the different lessons and the things that happened to me, I call them money memories. The thing that happened to me when I was a kid really set the tone for how I work today and how I run my business today and how I run my financial planning practice and how we treat other people.

I went to school for international business and marketing. I got married right out of college, and I married someone that was a financial advisor. I would help him. I was still at Mary Kay Cosmetics part time, and when I wasn’t doing a Mary Kay class, or at my full time job as a food broker, I would go with him on his appointments. Eventually, I started selling Mary Kay to all the men at the Morgan Stanley office here in Minnesota.

The branch manager over the years would be pull me aside and they’re like, “Well, if you can sell makeup to men, you should be a financial advisor.” Like, “Haha. Nope, nope. That’s not me”, but I ended up leaving being a food broker and worked for an insurance company as a recruiter. After a while, they had me take the test that I was having people take and my scores, they said, were off the charts. They’re like, “You should be doing this. This is the career that was meant for you.” I really just listened to everyone around me. It was one of those aha moments, where I’m like, “Gosh, people are seeing something in me that I’m maybe not necessarily seeing myself.”

That’s how I got started in the financial services industry. Never planned on doing this, and then I believe … So many times I get asked, “How did you become so successful?” For me, one, it’s doing what you love and being very authentic, but it’s also finding your niche. I’m not an advocate of divorce, but in 1999, I became a certified divorce financial analyst, and I was the first person in Minnesota to do that. The program had gotten started out of Colorado. With that, it made me different. One, I was different because I was a female in a very male-dominated industry, but two, I was a certified divorce financial analyst and I started helping people through the divorce process financially and dealing with the ramifications of that.

Which that led me to do radio and TV. I did a radio show for five years. Then now, fast forward, I’m generally on TV once a week. That could be anywhere across the country. Last week I was on in Vegas. The week before I was on in Washington DC. This week I’m here in Minnesota. That led me to writing books. My fifth book is coming out in September.

I just find it fascinating how financial services and being a financial advisor, it’s never a career that I ever thought I would be in, but I love being a business owner. I love having flexibility, especially because I’m a single mom with two little kids, flexibility of my schedule, as well as really defining the culture of my company and the firm and how we do things and how we help people, because we just really do things dramatically different than just any other financial advisor out there.

I really feel blessed that I really listened to people around me looking at the skills that I had of one, being super analytical and super intelligent, but also two, on the other extreme, being super creative and loving the marketing side of things. That’s where blending both of those together has really just been awesome. I’m very blessed to be where I’m at and to be a business owner. I love it.

Steve Gordon: You mentioned do what you love, and there is this whole line of thinking out there that if you do what you love, the rest will sort of take care of itself, but it sounds like you stumbled across the thing that you’re doing now. Is it the fact that you’re a financial advisor, that you’re in that field, that really drives you, or just the challenge of building a business and serving people and helping solve problems?

Nicole Middendorf: It’s the challenge of leaving a legacy. Before I went to college, I was the editor of my school paper. I always loved writing. I always had wanted to write a book. My mom was a business owner. She owned a hair salon, and so I just always watched my mom from a standpoint of like, “Gosh. I want to have kids, but yet, how am I going to do that? How can I work in the corporate world and have, and I hate the word balanced, but how can I have balance in my life?”

Then I did a few different video projects and things in college where I was like an anchor of a TV show gig. I was like, “Gosh.” I loved the communication side of things and the journalism side of things, as well as I loved organizing and planning. I’ve always just been an extreme planner and planning out everything in advance and being very creative, but yet, also, when I went to school for international business and marketing, I loved the marketing side of things. That’s where doing what I do now, it all fell into place, but I didn’t plan that it would happen this way.

Over the years, it’s really only in the last like about three years where everything has just kind of clicked. There’s the book from Malcolm Gladwell called The Tipping Point. For me, I have my own foundation. My personal life changed and I got divorced. We were separated in 2010, and I was like, “Gosh, how did I get where I’m at? How did from the outside everyone think I was so happy and had this perfect life, but on the inside, I was just completely miserable and unhappy?”

I sat down in 2010 and I rewrote my bucket list. On that list was a handful of things, but one of them was to drive a race car. I met with my best friend from college. I was like, “Hey, will you come up to northern Minnesota with me and drive a race car? I rewrote my bucket list, and I’ve committed to myself that I’m going to do one thing every month.” He’s like, “Nic, in anything you do, you don’t just put 100% into it. You put 180%.” He’s like, “You can’t just … ” This is nothing against northern Minnesota, but he’s like, “You can’t go up to northern Minnesota.” He’s like, “You need to go to a real speedway.” I’m like, “Well, where is that?” I didn’t even know how to drive a stick shift of a car. He’s like, “Well, go to Vegas or go to Florida.”

I hopped on a plane and flew to Vegas to drive a race car. On that plane ride, there was a gentleman sitting next to me. You know how you’re on a plane and they just have to talk to you the whole time? This gentleman was talking to me, trying to talk to me, the whole trip. He couldn’t understand why I wasn’t going to Vegas to gamble, like why I was just going there to drive a race car. I was like, “Well, I redid my bucket list.” He’s like, “Oh my gosh! I’m so sorry.” I’m like, “What?” He’s like, “You’re so young. Is it cancer?” I’m like, “No.”

When I landed, I texted Katherine, my chief marketing officer, and I said, “I’ve committed to do one thing every month to myself on this bucket list.” I’m like, “I can’t live the rest of my life telling people I’m doing something on my bucket list because they think I’m dying.” I’m like, “We need to come up with something”, so we came up with the Live It List, and I trademarked it. I just kept doing one thing every month. As I was doing this, clients would hear about it or I would go and do things with my attorney or my CPA. It just kind of started to spread.

Then I learned the statistic that one in three Americans is happy. I’m like, “Okay. I could change that.” I could help change that because people tie in so much to, “Oh, I’ll be happy when I have $1 million dollars, or I’ll be happy when I have $5 million or $10 million.” It doesn’t matter what the dollar amount. It’s just people tie so much of their happiness to money. I really don’t believe that at all. I have so many clients that would give every penny that they have away if they could save their wife from dying of cancer or cure their medical issues. I really learned how important your health is, as well as how important your happiness is.

Now, fast forward, I have my own foundation. We grant Live It List experiences. We raise money to help other people that … It’s a child that ended up with cancer and they’re then in remission, and then we take them and do something. Or like last year, we do tons of various things, but the one that stuck out the most was this woman, she’s a grandma, and she all in last year, all this stuff happened for her. She became diagnosed with stage four cancer, her husband became disabled, her son was killed in a car accident, and her grandson was in a four-wheeler accident and broke both of his legs all in one year.

Steve Gordon: Oh my goodness.

Nicole Middendorf: All she wanted to do was go and take her grandkids to a waterpark before she passed away. I had never been to Wisconsin Dells, this waterpark in Wisconsin. My kids had never been there. My parents had never been there. So I took my kids and my parents, and the same weekend, we sent her and her family. One, it was a giveback for me. We never met them. I did offer. I’m like, “Here’s my cellphone. If you want us to take you out to dinner one night, we will.”

We never met her, but for my kids, who now they’re nine and 10, for them to be at a place and know that there is someone else there that their grandma may not be around in a short period of time, it brings about really what money’s about. It’s that sense of appreciation and helping people and having experiences because that’s what really matters, not necessarily having a certain dollar amount, because what is that money for? Is it helping you really live life to the fullest and achieve your goals?

That’s why I have the whole Live It List, and that’s why we’re not your typical financial planning firm. We’re really helping people be happy in life and really live life to the fullest. Tying in the marketing and the analytical and my own personal bad experiences, because I believe from some of the worst things in life that happen to you come some of the best. The Live It List, I didn’t plan for it to take on this huge life that it has. I just wanted to find my own confidence back and be happy. That’s what’s so cool about it, is that I’m able to tie everything into my financial planning practice and really help inspire people across the country and really help people be happy.

Steve Gordon: Wow. Yeah. It’s amazing how the little interactions sometimes that you have put you on a different path and get you refocused and in a new direction. It’s fantastic work that you’re doing.

I want to take a quick break, and when we come back, I want to dive into how you approach working with business owners around their money and really, thinking about the people who are listening, what are some of the key things that they should be looking at? I know everybody’s different, but I think that would be hugely beneficial for folks to begin to wrap their heads around, “How do I deal with money? How do I think about money?”, and then go forward. We’ll be right back with more from Nicole Middendorf.

Hey. Welcome back everybody. This is Steve Gordon, and I’m again talking with Nicole Middendorf from Prosperwell Financial. Nicole, you got a fascinating story. I’m sure you hear that, and that’s probably one of the reasons you’re on TV every week is you’ve got a heck of a story to share. To do what you’ve done, if you look at what you’re doing with the foundation and the idea of the Live It List and all of that, you’ve gotten to a place in how you deal with money inside your own business that a lot of business owners never get to.

Nicole Middendorf: Right.

Steve Gordon: A lot of business owners that would be sitting here listening to this saying, “Oh that’s great for her. She’s super successful, and I’m not there yet. That’ll be something that maybe I never get to or that is 10 years down the line.” I think that’s probably false thinking, but how do you help business owners improve their thinking around money? What’s your perspective on that?

Nicole Middendorf: A lot of it is, going back to, and I mentioned this earlier, what is your money memory? What are your values? How do you think about money? So much of it … I don’t know if you’ve ever read the book Traction, but I’m a huge advocate of that. I have learned the most by making many mistakes. I always say I’m trying to make mistakes faster so I can learn more from them. Traction for business owners and for myself has just been a huge tool because what it’s done for me in my own business and as I’ve helped advise other business owners is it takes it away from the owner and really empowers the leadership and the ability and the knowledge of the business and the goal focus of the business off to the employees.

The whole goal as a business owner is that your business can run without you. That’s really my goal is to help other people have that amazing experience and have that great business. A lot of times, I feel like I’m working with business owners that have developed … Let’s say they’ve developed this amazing product or they have this phenomenal service. They have this amazing hair style salon, or whatever it is, but they’re horrible with numbers. A lot of times, the business owner’s great at coming up with the idea or coming up with the business, “But how do I really manage it?”

That’s where I’m such a huge advocate of. It’s so important that you have a great CPA, a great bookkeeper, a great attorney. You have all of these people, and in my opinion, the wealth advisor should be the person that’s coordinating all of those people to help get you on track and stay on track. One, it’s our job, or a wealth advisor’s job, in my opinion, to help come up with the financial plan. That’s driven by what’s important to you with money, what are your values, what are your goals, where do you want to be, and really then coordinating your CPA and all of the other people that advise you to help implement that plan.

Many times … I’m a huge advocate of if you’re in a relationship that you bring your spouse to the meetings and that your spouse is involved. A lot of times, that’s where this amazing dynamic can happen because you’re answering some of these tough questions that can be uncomfortable. There’s so many days where I feel like I’m a marriage therapist. That’s what my next book is about. It’s coming out on September 20th and it’s titled Who Pays: Navigating Love and Money. It’s for individuals that are single, that are out dating, as well as it’s people that are married.

It’s got questions in there because so many times … There’s two themes that I feel like I give a lot of advice on as homework for clients that come in. One is go have a money date. That is, sitting down with your significant other, and maybe they work in the business, maybe not, but they’re having the conversations. It can be anything as simple as what credit card debt you have or what’s the interest rate on your mortgage or what life insurance you have or how your investments have done. The talks that you can have around money really are endless.

Then the second thing I feel like I handout a lot of advice is go home, take your credit cards, put them in a class of water, and put them in a freezer. The money date and doing the freezer example, a lot of the times it’s helping people change their behavior. I didn’t go to school for psychology, but I feel like I’ve read enough psychology books, and so much of it is … So much of where you want to be and where you want your success is driven by mentally taking off a lot of these mental blocks and figuring out, “Where am I? Where is my business? Where do I want it to go? What can I do to make it happen and make it get there?”

Steve Gordon: Yeah. I can see behavioral psychology being probably the key thing you need to know and need to employ to get people to change. I think it’s such an important point to involve your spouse in the financial planning of the business, particularly in an entrepreneurial business where your personal finances are so completely wrapped into the business that you almost need to do that.

I don’t see a lot of entrepreneurs actually doing that because I think it can be difficult. Sometimes you feel like maybe the spouse won’t fully understand. Oftentimes, there are a lot of pressures, outside pressures, that accompany all of that. When things aren’t going well, there is certainly embarrassment and fear and all of that that get built into it that make it very difficult to have that kind of open exchange. I know myself, having been through really great highs in business and been through a few times that weren’t so high, the tendency to retreat is always there, but I always feel like you’re so much better off being open about it and actually going out and leaning on the people around you in those times to get through.

Nicole Middendorf: Right. I particularly also feel like it’s hard for women to ask for help. I was actually at an event last night. It was a Girl Scout event that was awarding … The majority of female business owners out there were actually Girl Scouts. I’m a former Girl Scout. I was at this event last night, and that was really the theme of it, is these women who are CEOs or executives, high powered … There were four of them that were honored and given leadership awards last night, and all of them said one of the things that they need to get over and learn is how to ask for help.

I’ve had to do that. It took me a while. The moment for me that clicked was I am really the only single mom in our neighborhood and I have a pool, and all of a sudden, one day, I had 12 kids in my pool. They were all the neighbor kids. Where were the moms? They were on the tennis court next door doing cardio tennis. I had this aha moment of like, “Okay. I’m a single mom that what lacks for me is working out.” I’m like, “I’m the one that should be on the tennis court working out while these other moms, who are stay at home moms, should be with the kids.”

It’s really important to say what you want and own your own voice and be very authentic and not hesitate to ask for help. That was one of my … I am naturally a perfectionist, so nowadays, I call myself a recovering perfectionist, which it bodes well in the industry that I am in because I have to be. I can’t go in and buy a stock when I should be selling a stock, or I can’t … We need to dot our Is and cross our Ts and be perfect when we’re doing projections and numbers and all of that.

It bodes well to my career, but at the same standpoint, being a perfectionist is … I had to get over myself of, “Okay. I have employees”, and just let them go. They’re going to do things sometimes a little bit differently than how I would have done them, but I really … And now I’m on the opposite end, that I delegate everything I possibly can, but in the beginning, it was very difficult for me because I was such a perfectionist. I just kept thinking, “Oh, it’ll take me 10 minutes versus if I show someone how to do it, it’s going to take me 30.” Really, I was hurting myself because I would take the 10 minutes, but then I would keep doing that activity over and over again versus taking 30 minutes, showing someone else how to do it, and then being done and being able to free up my time. That’s the joys of learning from our mistakes and the experiences that we have.

Steve Gordon: Yeah. I think we all have to go through that transition, particularly if you start a business literally from scratch and your bootstrapping and building as you go. As an owner, as a founder, you end up being the one that wears a lot of hats in the early days, and it can be very tough to give it up because you know, “Hey, this is what we do to deliver for clients.” You also know that that’s where the money comes from.

Yeah, it can be hard to let go, but one of the things I always advise our clients is there are really just four roles that you fulfill in the business, and sometimes fewer. It’s really around developing the vision, setting the message, developing the relationships, the key high level relationships that you need, and creating the intellectual property, the ideas. To the greatest extent possible, if you can draw a very tight circle around those four things and keep everything else out, all of a sudden, now the business can grow because you’ve had to build a team around you that can handle the other things.

I always think the big mistake that … I see this with so many businesses. They go and they want to grow and scale and do all of these things, and so they spend all this money on the outside trying to expand the message, and all that’s important. That’s the business we’re in. I know it’s important, but oftentimes, the single biggest and most effective lever point is just getting an assistant for the owner.

Nicole Middendorf: Right.

Steve Gordon: And freeing up five or 10 hours in a week.

Nicole Middendorf: Right. That’s a hard leap. I just had that conversation recently with a client who’s a business owner. She has employees, but she doesn’t really have like an executive assistant. She’s like, “I think I need to, but I’m scared.” She’s like, “Gosh.” I was trying to help her think about it, saying, “Okay. That’s great. You’re paying someone, but what is it doing to free up your time? Don’t look at necessarily paying your employees as a cost. You’ve got to look at what are you then bringing in as revenue from that.”

Steve Gordon: Yeah, absolutely. Absolutely. Nicole, I know we’ve only got a few minutes left, and I want to give you the opportunity to share where folks can learn more and if you’ve got any final thoughts for folks who are listening about how they can begin changing the way that they think about money, how they can begin optimizing how they leverage the money that is flowing through the business.

Nicole Middendorf: They can find me at or We have blogs. We have newsletters. We have videos. There’s TV. There’s tons of podcasts. There’s tons and tons of information on there. That’s where you can learn. We have everything from estate planning to credit cards to business ownership to Roth IRAs to all of that. That’s a great place to start.

Then always, I’m just a huge advocate … I find a lot of times that people are hesitant to see a financial advisor or see a wealth advisor. A lot of times people think, “Oh, well I don’t have enough money to see someone.” I’m this huge advocate. It’s like, “Okay. Well, how are you going to get money if you don’t get some advice and have a plan?” Don’t hesitate to interview a bunch of financial advisors and find someone that’s a good fit for you.

Then advice, I would say having a mentor is huge. I had a man, and he actually has passed away a couple years ago, but very rarely is there a day that goes by that I don’t talk about him or think about him. One of the things that he would say all the time is, “Give yourself grace.” There’s so many moments where I, as a planner, am so focused of, “Okay. I need to do more and more and more.” Now that my fifth book is done, it’s like I’m already working on the sixth book. So many times, it’s stopping and really just enjoying where you’re at and enjoying the ride because life goes by so quickly. Even out of some of those tough times that you have in the business, the nights that are sleepless or that you’re worried about something or something’s not working or you’re moving your office or you’re taking that next big leap of faith, it’s really just living within that moment and enjoying the process and giving yourself grace.

Steve Gordon: Absolutely. I think that’s great advice. Thank you for investing time with us today. This has been a lot of fun, and you certainly have a very inspiring story. I encourage everybody to go and check out and learn more about what you’re up to. Thanks for being here.

Nicole Middendorf: Thank you so much.

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