How To Become A Self-Employed Snowbird Before 40 And Live Life Intentionally With Zach & Holly Overcashier

Is it even possible to be a snowbird before 40 in a world where the term itself is almost associated with retirement? Our powerhouse couple guests did just that in their 30s. Zach and Holly Overcashier own and operate the superfoods company Elderwise Organics. Driven by their motto, “Enjoy the journey,” the Overcashiers work hard running two businesses and a thriving family while making sure they’re paying attention to living in the present moment. In this conversation, they tell us exactly how it is possible for someone to become a self-employed snowbird and enjoy being so while still at their prime. Enjoy the episode and be inspired!

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How To Become A Self-Employed Snowbird Before 40 And Live Life Intentionally With Zach & Holly Overcashier

Folks, I have interviewed a lot of different types of people from all different backgrounds throughout the years but for this episode, my brother and I are going to be interviewing some of our dearest friends. I was at this couple's wedding way back when, Zach and Holly Overcashier have been married for several years. I’m blown away. They, together, now own and operate Elderwise Organics, the trusted superfoods company and homeschool their incredible two children.

From the beginning, they had this dream of being self-employed snowbirds by age 40 and they accomplished this more in their 30s but, mind you, they started as broke college kids, I remember. They didn't take on any outside investors and they did it while remaining debt-free. That is a complete feat in itself.

This powerhouse couple have learned how to use their gifts and talents to successfully run two companies and still have time to play hard and enjoy hobbies. What's funny is they have very different hobbies but they make it work, which is awesome. I can learn from them. Their motto in life is, “Enjoy the journey.” Right along with Mama P. That's why they get along so well.

The thing is, their definition of success is being able to say yes to the things that they want to say yes to and no to the things they want to say no to all while staying true to their value. There is a lot of epic principles in that. Folks, I am so excited to learn from them and have them share their story. They're so passionate about holistic health, living intentionally with their children and making those simple moments memorable and taking care of their body so they can enjoy many more years together building their dream life. Without further ado, Zach and Holly Overcashier, welcome to the show.

Thank you so much for having us.

This is going to be fun. It'll be like our kayaking times together stuff. A little therapy session around the lake.

You know I'm always up for a good therapy session.

Always. We never run out of things to talk about. We'll have to focus on the few things that we do want to cover rather than what do we want to talk about here?

What I thought was so interesting, when Holly and I got together to shoot a couple of videos, I had no idea we lost touch for a period of time in our friendship. I didn't know the struggle they were on and how they organically created this company. Ben, why don't you kick us off by asking them questions about the get go of how things got rolling?

I want to hear about, in the intro broke college kids. There's a lot of people reading this that could probably identify. I know, I identify. I was a broke college kid myself. What was the transition because I know, Zach, you did work in Corporate America for a little bit and now you're fully entrepreneur? I want to hear a little bit more of your story and chronological of how you guys got started.

As you guys said, college does empty your pockets to start with and not having anything to go for with that. We got married very young. After we got married, we moved into a small little condo. We were still finishing school. We were trying to get little side jobs to make things work. We wanted to do things on our own.

Even though our parents did help us out in a lot of different formats and in different ways, we hit some walls where we were struggling to make ends meet and to try to pay rent. We were even food stamps. It was eye-opening and humbling. Once I graduated with my 40-year degree in business, I went out into the world expecting to scoop up maybe a high paying job. Maybe had higher expectations than what the world treats it to be. It was a struggle.

I worked these little side jobs at Ace Hardware even making $7 an hour just trying anything and everything. Taking any job interview that we possibly could. Holly was doing the same thing. She was out there trying to grind anything that we could come up to make ends meet. Eventually, I did get hired with Wells Fargo in the home mortgage area. I also worked for Microsoft for a little bit. Once we got in, people were able to see that we were willing to work our tails off doing anything and everything to make it work.

We were great employees. From there, we decided, “How do we want to spend our money? How do we want to save? Where do we want to go for time freedom?” That's where our dream started as we started building our own family or having our own family. We started saying, “We want to start planning and preparing to be our own bosses to work for ourselves.” Working our tail off for someone else is great. There's honor and respect in that but at the end of the day, we wanted to see the fruit from our labors.

Working oyur tail off for someone else is great and there's honor and respect in that, but at the end of the day, you want to see the fruit from your labors.

From there, we started something small. We started and we saw little things that we used the college food license. We’re always making things in the kitchen and we came up with ideas. In my background in business, we started putting things together. We just started while I was still working in Corporate America. I ended up shifting over into the pharmaceutical health insurance area because that was a more stable situation in Corporate America.

In several years in Corporate America where I planned my exit strategy of saying, “This is our safety net. This is what's providing for a family while building our businesses.” It took a lot of sweat and sleepless nights and things where we thought we were crazy. A lot of times at the end of the night, I'd do my day job then we'd be working at nighttime where a lot of our friends were watching Netflix or going out having a good time. We were grinding. We were working building something so we could have our time freedom back on the longevity end later. That's a nutshell. Do you want to add anything?

It's important, too, to say we started two businesses around the same time. He started football doctor, which is selling fantasy football draft kits which is very seasonal. While you do work at that time, it is so busy then I started selling elderberry syrup. There's a whole story and background behind that. I've had seven knee surgeries and a heart surgery. My holistic health and passion for health and Zach has had his own experience with healing his body from chronic migraines and being able to be off medications and stay away from that route and being able to experience what holistic living and holistic treatments and the benefits of that.

When we started our companies, it wasn't just Zach and I. We had a new baby at the time also and I was also pregnant. Our babies are only twenty months apart. There was so many things. I was also watching two little boys that were the same ages as mine. I felt like we had so much that we were spinning and doing and trying to balance. We also remodeled a whole house from the bottom up with our own bare hands and Zach's dad's help. I look back at it and I'm like, “What were we thinking?”

That is not easy. If I've seen marital strife, it's usually during remodels.

I'm not kidding you, guys. There were nights that we cried ourselves in sleep. I'm like, “I don't know what we were thinking.”

There was 30 days solid where Holly was doing over the house, either painting or remodeling something and I was doing my day job then fulfilling my orders until about 1:00 or 2:00 AM and getting up at 6:00 or 7:00 AM and doing it all over again in 30 days straight. We were burnt out.

Our babies, we're in diapers. It was insanity but what got us through was we knew what our why was. We kept saying that to each other like, “It's worth it. We know what we're putting into it. We know what the end goal is.” We kept envisioning what it was going to be like to be self-employed and to be essentially retiring early. We always kept saying like we want to be able to have a home that we can vacation to. That's what we kept focusing on and kept pushing through.

To take you back a little bit, when Zach first started fantasy football selling those draft kits. I would put the kids down for a nap and he's like, “Can you fold boards?” I would clear up our whole kitchen island and we would sit there. I would fold all of these boards and paper cut after paper cut and doing all of it by hand. Those are the memories that we have and our kids would be crawling around at night when we're doing it. They did everything with us. That is what makes us such a dynamic and strong team. We homeschool our kids because our kids don't know life apart from us.

We never had babysitters or outside help. I didn't ever drop my kids off. I always had the people bring their kids over like, “I'm at home anyway, bring your kids over. They can all play together.” I watched two little kids during the day also so that became like my own. We had a busy home. We had our house full, our hands were full and our hearts were full.

There were times at night where Zach and I were like, “Babe, what is this life that we're living?” When it goes back to the elderberry, I had this passion for wanting to help or help my own family stay healthy. The kids were always having the runny nose but then you know what that's like. The kids go to the gym or child care or get dropped off of the nursery at church and they always have this snotty nose or the little cough. My kids weren't having that and experiencing that. The other ones are like, “What in the world? Why are your kids not sick?” It's like, “I give them elderberry syrup.” They're like, “What is that like?” I’m like, “It’s so easy to make. I'll bring you a jar next time I come.”

I was handing out these jars of elderberry and pretty soon Zach’s like, “Are you charging people for these?” I'm like, “No, I’m just giving them away.” Zach is like, “You need to start charging people because this is costing us money.” I was like, “I suppose I could do that.” From there, I had to get licensed to cottage food to be able to do it legally. I put on a post one day on Facebook and I was like, “Would anyone be interested?” I had like 50 comments of people like, “Yes, I want to buy it.”

Pretty soon, I'm looking at that and I'm like, “I think I have a business.” I started doing these little pop-ups where I would go and sell it. I realized it's easier people come to me. People would show up at my front door and I would set them out with their name on them because I was also nursing a baby or feeding a baby or changing a diaper and always the doorbell would ring and I'm like half way between a diaper change.

I had this little box that I set them out in and people would come. They would either send me electronic payment or put cash under the table or under the little door mat. That was how it started then we eventually reached a point where we were making too much money to still be considered cottage food. Zach and I had to decide, “Are we going start shipping this and keep doing the liquid?” we were at this standstill, so we're like, “What do we do?”

I'll never forget the day that I brought him a Ziploc baggy with all of the ingredients in because I had attempted to send a jar of it to an acquaintance. She was like, “It broke while it was being shipped in the mail,” because I didn't have all the packaging and all the different things that were correct for it. I was still in the very new process of shipping liquids. She was like, “Can you just send me the ingredients? I feel like I could make it.” I'm like, “You could make it. It is so easy to do.”

I sent her the ingredients in a Ziploc baggy and I wrote out by hand the instructions that I brought to Zach. I'm like, “Can you put this in the mail for me?” He's like, “What is this?” I was like, “This is the ingredients to make elderberry and the instructions.” He's like, “Why aren't we selling this?” I'm like “Honey, nobody’s going to buy that.” He's like, “They are.” That is how Elderwise Organics has turned into what it is now. It was because I was selling the syrup and selling it on my front doorstep and it turned into, “What if we sold the ingredients so that people could make it themselves?” We could ship it and do it for a fraction of the cost because then all those things of like the honey, the liquid, shipping and the time that it took me compared to putting it into a baggie, sealing it up and sending it.

Less liquid and messy logistics.

It's probably way cheaper to ship because you don't have to deal with liquid.

It helped stable. It's made fresh and you can do it yourself.

You can customize it. Sometimes people like it sweeter and the affordability thing was huge for me because being where we were with our finances. I remember being at that point of looking at elderberry syrup on the shelf in the stores and being like, “That's so expensive.” We can't afford that. That was why I started making it myself.

I wanted to keep that as our core value or something that I could pass on to other moms who were in the same place because I knew I wasn't alone. I knew I wasn't the only mom who was on a budget who wanted to use holistic remedies but couldn't afford them. Being affordable, it was literally a fraction of the cost to make it yourself. I'm always all about teach them to fish rather than fishing themselves. That was how that whole thing turned into.

I love it.

Pretty long answer to the one question.

First of all, what that shows is like I'm the guy at a party. I can talk about real estate all day long. I tell people, I'm like “We don't have to talk about real estate but if you want to talk about real estate, I'll talk about it all day long.” It shows your passion for your business, which is amazing. I'm going to go back to what was the switch that flipped for you where you're like, “I want to be the entrepreneur. I want to work for yourself.” Maybe it was kids. What do you think flipped that switch for you?

I'll never forget the day that I thought of it. I was sitting in my basement and I had my corporate job. We had a static income. It was set. There was nothing more I could do or less. There was bonuses and such, but those are not. I was already doing everything I possibly could besides maybe taking on another job and I was already spending so much time doing that. We couldn't go on a vacation and I wanted to take my wife on a vacation.

I couldn't even get the charity and that was something we were passionate about. I was like, “We're making ends meet.” It's paycheck in and paycheck out. I was like, “I refuse to live this way. What can we do?” One day, I ordered a fancy football draft kit from offline and I got it. I looked at it and I was like, “It's something I'm passionate about. I enjoy doing.” I looked at it and I was like, “I think I can do this.” That's how it was born. I started doing all of the research, how to source it, how to create it, and make it. Fast forward several years later, I just bought out that competitor that I bought the first draft kit from.

No way. Good for you.

That's a cool full circle moment.

Several years later I bought the one from. He's no longer in business now.

That's awesome.

It was a point where I said, “We wanted more in life. We wanted more out of our finances. We wanted more. How do we make it? How do we do it?” Creating something or work for yourself in some other avenue was the only thing that we could come up with. We just started working toward that in any step that we could, whether it's baby steps or anytime we had the opportunity to go pedal the metal. We would do that, too. It was always a decision-making process through it. It made the most sense. We didn't want to be stuck where we were.

Snowbird: We wanted more out of life. We wanted more out of our clients. How do we do it?

I also love that you got started in a niche business. There's so many people who are like, “I want to have a business that appeals to everybody.” It's like no. You can be in a niche business and even if there is a competitor, you showed right there like, “There was a big competitor. I have some no name. Several years into it, I get to buy out my competitor because I did it better. I did it more efficiently.” I love that story because there's so many people who are like, “I don't want to start it until I have the perfect business.” There's no perfect business. Get out and start.

There's no perfect business. Just get out and start.

That's one of the things that I say to everybody when we're talking about what the startup is or what the business is. You just start it. Some way or somehow, you start it because the biggest thing that people do is they say, “I'll wait for this or I'll wait for the perfect timing.” There's never that perfect timing where the stars align to do it. If you do something then you work as it goes. I had a friend who's doing a business startup and he kept coming back to, “I need to do this first. I need to do that first or maybe I'll talk to clients when I'm more polished.” I'm like, “Go out and do it. Go get polished as you go.” It’s a mindset that holds people back of starting it and they never start it.

Going back to this, he was the first one that brought color labels to the industry when it comes to football. He was looking at it at everything was Black and White. He was like, “What if I put the positions of the players by color?” He was the first one to roll that out then everybody else followed suit. Within 2 or 3 weeks, everybody was had to trash their Black and White ones and bring it out because Zach was going to crush everybody because they can have color versus Black and White. What do you think people are going to choose?

It changed the entire industry. Anywhere you go, to see now that there's color by position labels is because it was started by me.

Which is such a cool thing. Those are the things that we talk about with people like, “How are you going to set yourself apart?” That was for us in the beginning with Elderwise and for him, too. He was like, “How am I going to set myself apart this year?” He's like, “I got to figure out how to do color but color is always more expensive.” We had to go through figuring out what is the printing look like and how much are we going to raise the prices by.

All those different components. When it comes to Elderwise, we always say that you can go online and you'll see lots of different varieties now. Back then, we were one of the first ones that were out there but it would always came back to quality and price. Our customers always know that we are going to give them the best price always. We will never ever overcharge people. We have not rose our prices.

You just come up with your core values. You stay true to those and you strategize as you go along. These are little strategy things that you put in place after you've already started. A lot of times, looking at someone who's already done it or has done it well or someone that you maybe could take advice in. Those are little nuggets that are invaluable.

I can't tell you enough that those little pieces that put together, for example, I gave Ben a call. I had a situation with a tenant and I was like, “Ben is an expert in this field. What's your advice? Any insight?” Any time you can have any relationships where those people can speak into those ways, have already done it and they show you by example. Those words you hang on to every word they say.

One of my goals, I instituted this a couple years ago but I want to continue doing it. It’s to take somebody out to lunch more successful than I am once a month. It doesn't even have to necessarily be monetarily. It can be like, “This guy has a solid marriage and I want to learn as much as I can from that or they raised some amazing children. I want to learn from that.” I agree with that.

One of my go-to mentors, Chris Harder. He taught us out of league lunches. Who is out of your league? Maybe they're an epic mom or an epic dad or maybe they're incredible in their fitness or their business. Whatever that is, wherever you are wanting to up level, build that relationship, add massive value to them, and you never know how that's going to come full circle.

I also loved your mantra just like both of ours. It's that ready, fire, and aim. You can pivot as you go along. You're not going to have it all figured out. Was there a point in either one of your journeys with the football business or with Elderwise Organics where it was like that rock bottom moment that you're like, “I don't know if I want to continue or has it been that progressive upward?” Tell me more.

There's been a lot of those.

It's why we value our success based off being able to say yes and no and staying true to our values. Oftentimes, what it comes back to is this reflecting our values. This is what we want because we can be wealthy people and our children want nothing to do with us or we have a strict children when we are older or Zach and I's marriage fall apart. What the heck's the point of that?

Our business is not what gets us up for the day. Our children and our marriage is what gets us up for the day. We love each other. Unrelenting love that we have for each other and our kids. Our business is something that we get to do together to be able to live the life that we want to live. We don't live for our business or our companies and we used to. There was a time where it was we put that before each other. We learned quickly that if we continued to choose that, it was going to lead us down a path in living a life that we wouldn't enjoy, so what was the point of it? There's been times.

There's a rock bottom where we were burning ourselves out. We got to a point where it was looking at our lives and saying, “If everything else is going to fall apart, what are we working for?” It was reeling back in what's the point of it and getting back on the same page of things. We have tons of business logistics that have gone sideways or expensive learning lessons. We had a vendor once before who had ripped us off.

There's lots of different stories where we've hit some pretty lows and we could have given up. We could have quit or said, “This is too hard,” but we always are like, “Let's pivot. Let's figure this out or let's do the hard work.” Working with the FDA alone. It's why people don't do it. It's hard work but it's also like, do you want things to be worth it and are you going to do the hard things to make it worth it? Without losing yourself. That's what Holly's message is, too. We've hit some rock bottoms of losing ourselves in the process because it takes a lot from you. It's a dedication but the fruit of your labors can be amazing. We are so glad we kept going.

The other piece, too, is like not trying to do it all alone and having great conversation. Zach is so good at the logistics, the backend and making sure that all the orders are fulfilling. I'm great at healing the customers, all the questions and making everything look beautiful. I do all of our packaging. I do all of our photography. I do every single one of our social media like posts and designs because I truly love it. It's something that I enjoy. In the beginning, it was out of necessity because hiring that out was not an option.

It was so expensive. Anytime we wanted to change packaging or do anything, then we would have to hire somebody to change and make all of those tweaks then we were on their timeline and calendar. That was something that myself taught. I learned how to do all of it through Canva and using my phone. I don't have the bright light and the white light. I go outside and take photos or have my little white box. That's the thing, too. People are like, “You have to have all of these other expenses,” and you don't. You can just learn how to do it. Watch a couple of YouTube videos and figure it out. If you want to do it, you'll do it.

The packing originally had stickers. We made stickers and put stickers on before. Now we have a whole manufacturer that produces them all for us. It's steps and figuring those things out as you go. If you don't do any of them and say, “It's not flashing up or I have to spend all this money to do it this way.” You're probably looking too far ahead instead of looking at where your next steps are.

I love the phrase, “Everything is figure-outable.” Especially in with this day and age with YouTube. If you want to figure something out, you can figure it out.

Everything is figureoutable.

It doesn't have to cost you a bunch of money.

I will tell you, a lot of my business education is not from my four year degree. It's from YouTube.

I love it.

Knowing somebody or seeing someone who's done it successfully, and show it. Why not?

I am going to ask a follow-up question. You said, “I've made some expensive mistakes.” What's one of your most expensive mistakes? If you can say it. If you can't say it, that's fine.

I'll go with the vendor one. Sourcing CMOs from and doing importations is a process. We found someone who was going to do the importation process for us. We found out the hard way that that is a slimy side of the business where it's a little sketchy and if they're doing the right process. We had a vendor through one of the Islands of Bernada who was going to be sourcing our CMOs.

We end up making a large order and they said it was going to come shipped. A month goes by, nothing came. Another month comes by and nothing came. They said it was it coming. They said it's coming. We got what six months in and we had to file basically, but since it was international aspects, we lost a lot of money on that.

You should share like a general number.

We lost thousands.

I'm one that I always tell people like, “You can learn from my experience.” I hired a contractor one time and he gave me a quote of $45,000. I didn't follow up. I didn't like, “Make sure whatever.” At the end of the project, it was $90,000. It was double what he had originally quoted me. It was because I wasn't monitoring. That's totally on me. It should have never happened but it's one of those things that you learned from it. Don't do that next time.

We then changed to a very good vetting process. We've even gone to St. Lucia is where we get our CMOs now. We haven’t gone to Ireland, but we vetted Ireland too. We have a vetting process, how's it done, where's it done, who are the people and what's the reputations. Also doing the importations ourselves. Everything's legal.

We work directly with customs and everything now to get it all done properly so that we don't have to rely on somebody else.

Rather than believing somebody else is going to do it.

Another one comes up to mind is we do sell a lot on Amazon, especially for the football doctor. Amazon has a policy book that is probably twenty Bibles worth of pols. They make enough policies to be gone basically.

We're not talking just ten commandments here.

Whatever Amazon wants or says is what happens. It's very hard to follow everything to a T or know everything. Learning processes through what's allowed, what's not, and navigating that. We've lost a lot of inventory. We've had a lot of shipments go bouncing back. We've lost a lot. That has been a tangled mess to come figure out.

Now once we're in, we even have partners that we've outsourced from Canada that help us with this. They have been fantastic. We've seen our sales increase. We've seen a lot of more fruits of someone that has expertise in this area that we have brought in to say, “Now it's worth it.” We've tried to do it on our own and balancing those risk to award type of situation.

It’s just how Instagram has an algorithm for things, so does Amazon. For us to try and keep up on all of that and figuring out all of the loops and hoops and this changed this week and now this month. Zach and I just both said, “The amount of time that it's going to take for us to learn it and do that and apply it. Why don't we hire that out?” Those are the things that we have learned and that is, is there somebody else that can do it better that still fits with the way that we want our company represented and our brand represented?

That's the other thing, as soon as you hand that key over, you're trusting them to represent your company the way that you want it to be represented. That, to me, is so important because we care so much about the quality. We care so much about the affordability and the pricing. Those are two things that are super important to us. The other thing is we keep everything local. I want to do a shout out to our team. We have an incredible team.

Our manager was here. We love her. She's so awesome. She was a goat farmer. She still technically is, this is a cool story. I'll make it short. We exacted a post about asking, “Does anybody know where we can get fire for our new wood burning stove?” People were like, “You got to go here. They have the best. The kids all chop it. It's something that they do as a side business.” I'm like, “This is great.” We show up and we're loading it into the back of our truck and there's goats running everywhere.

This old man was helping us. He was so kind and I was like, “What's up with all the goats?” He's like, “That's my daughter-in-law’s. She got a facility here where it's all licensed and legal. She's selling goat cheese and goat milk.” I'm like, “All of my friends are going to want that. Can you give me her number?” He's like, “Gosh.”

Before we even get down the driveway, I'm like, “Nikki, my name’s Holly. You don't know me but I would love to talk about.” In the meantime, Zach and I, we have ten acres of land in Minnesota. We were looking at what it was going to look like to build our own facility. I had so many questions about who did you use? What did you do? We came over and she gave us a wool tour and let us like milk the goats with her and take some cheese home.

Pretty soon, conversations led the other things and led the other things. She started working for us pro bono. She just wanted to be a part of what we were doing amazing. She's like, “I want to be a part of that.” Pretty soon, Zach's leaving corporate and she's like, “How else can I help? What else can I do?” We ended up hiring her you. Now we rent her facility. She transformed the whole thing over and kicked the goats out. Now it's an Elderwise Organics whole facility. She transformed the whole thing to serve and be able to be what we needed so that she could rent because she was realizing, “All of the effort and the time and everything that I'm putting into these goats, am I even making money?”

We sat down and analyzed everything for her and said like, “How do you want to live? What do you want?” Now, she gets to home school her kids. She's at home. Her work is in her backyard. It's all of those different things of what Elderwise has done, the nonprofits that we've been able to support and the things that we've been able to do, Zach and I.

I always said from the beginning. I was like, “I want to employ moms. I want to help moms be able to make money and not through network marketing and not through having to have a whole bunch of inventory in their closet.” All of these different things that I saw were required. We have employees now that are moms. We have an incredible team. It's not just Zach and I.

It's one of those things where it comes back to values of what you want to do. For us, we could have outsourced the core packer easily but to be able to have a little bit more control in how our products are handled, what they're done, and how we can have people in the community come. That person's doing instead of machine. That was important to us. That's something that we can do for our team that we now come to know and love. The story is incredible how that all have came to fruition.

Our joke is always like, “Always ask about the goats.”

Amazing epic thing will happen. I can't even put into words how this makes my heart jump because seeing you guys and knowing you for how many years since Zach's mom and my mom competed in Mrs. Minnesota together then we became friends and Holly came on the horizon. To see how you guys have not only come into your own but helped so many other people. Not only create a business plan for themselves but a life plan.

That's a lot of times what people sometimes forget, like, “Business, let's go.” That can be the backbone to give you the freedoms that you want in your life. At the end of the day, if you forget to create the life plan, then good luck in the quality of life down the line. That's the value that I've seen that you guys have maybe got a little or maybe some blurred lines at the beginning. Now you've kept the main thing, the main thing. Zach, I didn't even know that you do mentorship. Why don't you tell a little bit about that aspect because that's so powerful for some of those people that have a dream inside of them but they're like, “Where do I go from here?

It's a passion of mine. I do free sessions for anybody who has business questions or is starting a business, especially. I specialize in startups and starting small. Everybody has a different place and background in what they're doing. Everything is always unique, which I love. I love helping people. It's something I feel like I'm an expert in the field of doing by example. I had several people with startups. There was somebody who wanted to bake. They wanted to sell their goods. How can I get my goods into a legal format and knowing the ins and outs of those because that stuff can be daunting. I love to be helpful and a resource for those things and see people go after that.

I love it. I want to hear a little bit more about your guys' relationship in terms of entrepreneurship because I know like me and my wife work together. Every once in a while, we catch ourselves and she's my transaction coordinator. She's a lot of the back-end paperwork but we catch ourselves constantly talking about business. How do you guys navigate that relationship of entrepreneurship/relationship?

This question is a doozy.

You can unpack it.

We talk shop a lot, I'll be honest but we're passionate about it. It's not something like, “We're talking about work.” It's something that's very dear to us. It's something that we enjoy doing. As she said before, she loves designing and creating. She has her hand in our company. My expertise come with logistics and scaling and what those things look like. It's like a one-two punch and getting on the same page with things. We make decisions together. We talk about those things but we also have a little bit of balance. For our date nights, we like to go to Costco.

Get the $1.50 hot dog.

No shopping cart where you have to balance everything.

You should see the looks we get. People are all like, “What the heck is wrong with these people?” I'm like, “This is my cardio for the day. Leave me alone.”

A lot of time, Holly does break down and gets the cart and the game ends. We have fun with other things that don't necessarily equate. We've homeschooled kids that takes up a lot of time. We're passionate about that. We love enjoying some of the passion. She loves to run. I like sports. We talk about those things. Maybe our interests are there different but we still talk about those things together.

Very different.

Raising a family together is a whole other category as well. I feel like we have a good balance but at the same time, we don't feel like even though we do talk shop a lot, we don't feel like it's talking shop.

Snowbird: We have a good balance, but at the same time, even though we do talk shop a lot, we don't feel like it's talking shop.

For us to be able to share with other people who do feel like that's all that you talk about. We have had it in the past where we had to say, “Tonight, when we put the kids to bed, let's go through some questions.” We have these like little date night questions where if we're not intentional, we will find ourselves not focusing on the asking each other like,

“How was your day or was there anything?”

We spend every single day together also. If he's having a bad day, I already know it. It's not he’s coming home from the office and I'm like, “Tell me about your day.” His office is my office. We're always together. That is also a different dynamic of our marriage and our relationship but we do. We have certain nights that we set aside. We also start every single morning together as a family and we say our family vision and what we're passionate about. We say, “We have eyes of compassion and love to see ourselves and the beauty in ourselves and the people in the world around us.”

To us, it's like if we can start our day off right and we put on our armor and we say something that we're grateful for that day. That is how we start every single day of the family. We find so much value in that. When we start that way, we have the right vision for the day rather than starting on our phone, email, or our to-do list. It's all about how we start our day and we have learned that. We've found that. If you are an entrepreneur, I would highly suggest that if your value is your business. That is how you're going to start your day.

If that is all that you care about, if that is where your heart is at, and I'm not saying it's wrong. If you're trying to navigate into more of a, “I want to have more of appreciating life and setting those goals for like what I want,” then start your day that way. Don't start your day on your phone because we've lived a certain season of our life where it was like as soon as we wake up, it was like, “Let's get after those emails. Let's get after everything rather than drinking a cup of tea, going out and taking in the sunshine on our eyes and starting together as a family.

If you don't have a family, start it with your spouse. If you can't do that, call them on the phone while they're driving into work. They probably have a little bit of a commute. Be creative with things because how you start your day is going to be a trajectory for how the whole day goes. If it starts on your device, it's going to be a different experience compared to when you're starting connecting.

I feel like her touching on the cards or the questions. I love those because we've been married for several years and we've talked about almost everything. Sometimes, when we're eating sushi, staring across each other. There's times where we won't say anything. We're just happy being together. There's other times, we have to go into it like, Holly's like, “I want to talk.” What do we want to talk about? Setting the expectation so we know like, “Are we talking shop or life? Are we bringing the questions?” We do the random questions and have conversation organically created from there. Sometimes it's nice, at least for me, to have the expectation of like, “What are we talking about?”

I got another question for you because your story is cool. We were on food stamps for a little while. We launched. When did you feel like, “I've made it or I'm out of it or I'm making something of myself?”

I feel like there was certain parts that made me feel accomplished in certain areas that worked hard toward. I would set a goal and I've realized I can set realistic goals and still fall down to the height of my systems. I will always fall to whatever my systems are and that's something that I've realized is like I love to set goals. I go shoot for those goals but if I don't hit those goals, I always fall to whatever my systems are.

Putting those in place, I feel like enhancing those every year, setting goals, what are my systems, whether that's relational or business. I would say from a business standpoint, I've I feel like I've been successful when I had a goal. I spent eight years in Corporate America. I worked very hard, had a lot of trials and errors, but being able to walk away from Corporate America saying, “We're going to be okay and we're going to do this from now on.”

For me, it was impactful. I don't think there's ever for me like I have arrived. It's more of a journey. That’s what our motto is but there's accomplishments. We like to celebrate our victories. That's part of a huge thing in life. We love to celebrate and just say, “We did this or babe, this was hard and we did this.” Whether that's with Holly running races or us having the walk away from Corporate America or hit sales pinnacles or hear customer testimonies. We get so many custom testimonies. I'm like, “This alone is worth it.” It's a hard question to answer.

I can remember it. When we were sitting in your office in Minnesota and you were like, “Babe, our Elderwise is continuing to grow. Our sales for football doctor could replace my Corporate America.” It was never a place of like, “As long as we can replace what you're making,” because what if next year he went negative then how do we do that? It was like, Elderwise was on the rise and it was doing very well.

We had his Corporate America plus this extra, so it was like a buffer. That was when he felt like he could take off the weight. We call them the golden handcuffs of Corporate America and be able to feel good about that. I feel like that was a monument for me, especially because then I didn't feel so much pressure with Elderwise to feel like it had to perform and continue to grow because Zach had built that.

Not that I don't help him with football doctor but that was his thing. He did way more of it than I did to help with that. When he grew that company to be able to replace what he was doing in Corporate America, then we had that extra, as I said buffer. That was when we put in the like, “How many more months are you going to be doing this?” To be able to run two companies and work full-time Corporate America, be an incredible dad, and be a dedicated and loyal husband, he was burning all candles. Any candle that you can burn, he was burning it. It was like, “Why do we keep doing this if you don't need to do this?”

I’m going to grind anything I do, I do 100%.

We had the goal of doing that by age 40. We were both like, “Let's be snowboard by age 40. Let's be self-employed so that we can go, do and be whatever we want to by age 40.” He was able to do it by age 34 or 35. It was that time frame that he walked away.

I'll say this. I'll pivot from the question from arriving to feeling accomplished from what I set out for what we wanted to do.

That main goal.

After a decade of working hard, working my tail off, working smart, learning and growing that I can wake up in the morning and go, “What do we want to do today?” There’s things that I have to do still. There's plenty of logistics and my calendar gets filled with stuff. We go around in our family, our kids and us and we say one thing we're grateful for or thankful for every single morning. I even said, “I am so glad I do not have to go off to some job now.” It’s the best feeling ever.

Snowbird: Waking up and not having to go to some job is the best feeling ever.

We get to be a part of our kid’s lives. That was my ultimate goal as a mom. I don't want to miss any moments. I don't want to miss them. If I choose to miss them, that's on me. I don't want to be forced to miss any moments.

It's a big value of ours.

It was of utmost importance to me. When we talked about that as a family, like Zach and I when we were starting our family. I'm just like, “This is more important to me than any amount of money.” We also said, “Being successful, how are we able to make those choices?” You need some money to be able to do that and to be able to have resources to be able to do those and make those choices. It's cool to sit back and reflect and talk about it of where we've been and where we've come to. You guys know, we were so poor.

We were college students that loved each other and knew we wanted to take on this big world together. That's what we did. We have this sign in Minnesota and we'll be bringing it down when we get our house finished and it says “Together they build the life that they love.” It's true. We've worked so hard. It's just in those beginning years, we didn't take a vacation until we had been married for what eight years. That’s insane,

The other thing is you have to come up what are you willing to sacrifice to have or what's the hard working you’re going to put in? There's working smart too. I know great people that work 3 or 4 jobs hard but they're not efficient. If there's one person who's helped them direct them, hard workers can produce more than what they're doing. Going even back to the food stamps, it was tough.

We're buying canned beans and eating. It was a rough time but we never lost sight of who we are and what we want to do and be willing to do the hard work and the sacrifices of like what Holly said. We didn't go on a vacation for 6 or 7 years. It was killing me. I wanted to give the charity. I couldn't do that. Some of these things were I’m like, “There's more to life than just paycheck to paycheck. How are we going to do it?”

We sacrificed. We didn't go on vacations. Guess what? There's other people putting stuff on their credit card going on the vacations because that's what they wanted to do. They wanted a bigger house. They wanted cars. They wanted whatever that is and I said, “We can't afford that.” We could have gone indebted and still be digging our way out. I said, “How can we work towards these goals without having these repercussions later of what people want now?”

Play the long game. That's one of Ben's mantras. He's taught me of that a lot, even in the real estate arena, long game and relationships. Any other words you want to share before we go to lightning round with the lady boss?

Play the long game.

Sounds like the Bazinga game from Friends.

We're going to have some fun, friends. All right, how it works, 30 seconds or less.

I'm talking to you, Holly, 30 seconds or less.

Answer these questions. We can go back and forth so that you guys don't get confused with who answers. Who's going first? Holly, Chipotle or Chick-fil-A?

Chipotle.

Got it. Your favorite way to spend downtime?

Reading.

What are you absolutely addicted to?

My kids.

What are you reading now?

It's a great book. It's called The Midnight Library.

 Is it fiction?

Fiction. It's with my book club.

Nice.

Book club.

Zach, the best piece of advice you've ever received?

The days are long, the years are short.

I identify with that especially with kids.

That made me enjoy the moments that are hard.

The most embarrassing moment.

You only got 30 seconds, go.

I pooped my pants one time when I was driving down the road when there's a turtle. It’s a long story.

I loved I pooped my pants when I was driving because there was a turtle. I’m kidding.

We'll keep it at that.

That's why she's laughing.

Favorite food.

Sushi, probably.

Who inspires you? Who do you aspire to be like?

There's like different facets that I aspire, whether it's relational or business or sports.

Holly, do you have one?

I don't know. It's so hard. I feel like there's attributes from certain people. I've learned over my lifetime to not put anybody in this one place to idolize because it had happened too many times. It make a life choice that I would never ever make and it crumbles. I find myself crumbling because I put so much of my identity or authority into them. When they make a misstep, I find myself not being able to step because I follow too close to them. I try to not follow too closely in anybody's footsteps and see where people have stepped and choose to make my own path.

That's good.

Coffee or chocolate?

Chocolate.

Coffee.

Describe yourself in one word.

Spontaneous.

Conservative.

That definitely defines your relationship right there.

You did amazing with the lightning round with Lady Boss. Whole stretch, last three questions. If someone met you and said, “I want to become the boss of my own life and call the shots. What's my first step?”

Go do it. They have something in mind that makes them want to do that. I would just tell them go do it because so many people get stuck in those logistics of like, “What do I do?” Figure out a way to do it. You'll do it.

If you have something you want to do, just do it. You’ll figure it out.

Find somebody who's doing it well and mimic or take tips and advice or whatever you can do. Somebody who's already doing what you want to do and do it.

To Ben's thing that he commented with the resources that we have in YouTube. When Zach and I started several years ago, compared to what's available. Zach and I are like, “If we would have known what we knew then.” Take advantage of all the resources that are online and go do it. There's so many opportunities out there. You don't even need a college degree anymore, to be honest. You can learn anything. It's crazy.

I'll say one more thing to that. Be humble and be open to listening to someone else who's done it and not get so narrow minded that you're doing when you haven't done it yourself.

What is your definition of a boss?

Someone who's in charge of themselves and maybe others.

It's that person who's able to have that success like what we define it as. The person that gets to say yes to the things they want to say, no to the things they want to say no to and stay true to their values. There's plenty of bosses that I know that treat people like garbage and are a slave to their job or their business because they've created in a way where they can't step away from it and they don't have a life. If they're a boss but they don't have a life, and to me, that's what a life is. It’s that freedom.

The bosses are who's making the decisions whether they're in good or bad.

Any last words of wisdom before you share your handles and where people can get in touch with you guys?

I'll say anything to anybody who's feeling sick or is uncertain that there are always going to be calculated risks. There's always has to be labor before there's fruit and being wise knows and how you're going to move forward. There's got to be decision-making. Things don't just happen for you. If you're not working towards something, you're not going to wake up one day it's going to happen. For some reason, a lot of us feel stuck and they expect some other thing to handle or take care of it.

There might be influences that can associate or help with that. If you don't go and make it your happen yourself or you don't make those calculator risks or it's a you thing. That doesn't mean you have to have a capital. It doesn't mean you have to have a bunch of money and the smartest person in the room. It doesn't mean anything, but if you are working toward it and you are working toward it in a way that is wise.

The fruit to your labor will come. It's just a matter of time. I do want to put a little caveat because I love to push people in that way and for my perspective in business is know what you're giving up and what you're going to be sacrificing. Is it worth it? For me, I wouldn't sacrifice my time raising my kids. I've already had a couple of opportunities to come up and I'm like, “I could make a lot of money doing this or that, but it's going to take a lot from me to do it now.” I'm not going to say yes to that because I have other values in place. Know what the sacrifice is going to be and make sure you're good with that. That's the track you got to go toward.

Why don't you guys share your handles? Where people can get in touch with you? Zach, for mentorship, and also Elderwise Organics. Where can they find that as well and check out all the amazing health products that you guys have to offer?

Elderwise Organics, we're on social media everywhere at @ElderwiseOrganics. Our website is also ElderwiseOrganics.com. You can see everything on there of what we do and we provide this one. As far as the mentoring goes, if you can look up to Zach Overcashier, I'll pop up. Send me a direct message.

You can message us on social media, too.

The boss life has a lot of glitz and glamor that comes along with it, but it's not everything.

You can use the companies as well. It's fine.

Thank you from the bottom of Ben and my heart. I'll speak for Ben. We love you guys. We're so grateful for both of your friendships, your wisdom, and insight on and off the court. You folks are epic humans. Thank you for joining us. For all of our friends on the other side, I want to encourage you, as I say every episode, now is your time to fire your fear, build your faith, and become the boss of your own life. Let's get after it, folks.

Thanks for having us.

Thank you. I love you guys.

Important Links

About Zach & Holy Overcashier

Zach and Holly Overcashier have been married for 14 years and together, they own & operate Elderwise Organics “The Trusted Superfoods Company” and homeschool their 2 children who are 8 & 10.

They started as broke college kids with a big dream in their hearts and an unrelenting love for each other.

They were able to accomplish their dream of being self employed snow birds in their 30’s all while staying debt free and not using any outside investors!

Together they are a powerhouse couple and have learned how to use their gifts and talents to successfully run 2 companies and still make time to play hard and enjoy their hobbies too (which are very different and quite honestly opposite of each other.)

They live by the motto “enjoy the journey” and their definition of success is: Being able to say YES to the things they want to say yes to and NO to the things they want to say no to while staying true to their VALUES.

They are passionate about holistic health, living life intentionally with their children, making the simple moments memorable and taking care of their bodies so they can enjoy many more years together building their dream life!