Life Lessons on Resilience, Leadership, Laughter, Overcoming Obstacles with Tessa Greenspan-REIA 493

In this Streams to Impact podcast episode, host Dr. Allen interviews Tessa Greenspan, former owner of Sappington Farmers Market in St. Louis. Greenspan recounts her personal origin story—from a poverty‑stricken childhood in an outhouse‑filled home to becoming a multimillion‑dollar retailer and best‑selling author. She details how she turned a supermarket from $1 million in debt to $10 million in annual sales through a series of creative, community‑focused strategies: operating a bread‑truck, partnering with a father‑son grocery team, designing a larger store with a toy train attraction, sourcing niche products for Bosnian immigrants, and creating a low‑cost cheese operation. Greenspan emphasizes the importance of resilience learned from her mother’s hardships, and she shares leadership practices such as profit‑sharing, employee recognition, and high retention. She also describes her charitable “wishing‑well” program, monthly community events, and the philosophy that charity fuels business. The conversation moves to her current work mentoring CEOs through her company No Limitations Ever, using a framework called C.A.N.C.E.L., and promotes her book “From Outhouse to Penthouse,” which is slated for a movie adaptation. The episode closes with promotional plugs for Steedtalker Capital’s passive‑real‑estate investment program.
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Welcome to Streams to Impact, the podcast where busy professionals are empowered to develop multiple streams of passive income built on solid, secure, hands-off commercial real estate investments. This show is not just about wealth development. Every episode, we dive deep into inspiring conversations with professionals who are living life to its fullest while making significant and meaningful impacts on a world in great need. Engage with us each week and discover how you can thrive and flourish abundantly in all areas of your life. Now, here is your host, Dr. Allen.
Hello, Enlightened Investors, and welcome back to Streams to Impact. We're so delighted that you are with us here today. We have such a fascinating story to share with you today. Tessa Greenspan is one of the most influential women in business as the former owner of Sappington Farmers Market in St. Louis, Missouri. She owned that for about 28 years, and during that time, Tessa took a supermarket from $1 million in debt to $10 million in sales. Now a best-selling author, she mentors business owners and speaks on business motivation and health. Tessa's Renowned for her leadership, positivity, and generosity, earning her numerous awards and global recognition. So Tessa, you have a fascinating, fascinating story. So tell us about your journey from outhouse to penthouse.
Well, I'll start with, yes, I took a business from $1 million in debt to $10 million in sales, and I will really discuss how that all came about. I think it's really important though to start with where I came from. My mother, I'll tell you about my mother, who was from the back hills of Arkansas, went to a picnic and met a cute guy, and he pulled her in the woods and raped her.
Mm-hmm.
And she was pregnant with me as a result. I was born in this house that had a hard dirt floor, no electricity, no running water, and an outhouse out back. And so that's where I began. So it really is a good story, I feel, because I had a role model in my mother who really didn't have any education, but she was positive.
She—
nothing stopped her. Nothing stopped her. So just on— I will say it's really important for everyone to know what shaped their life.
Mm-hmm.
Sometimes people, something happens, or, you know, when they're young, or maybe a teenager, or even 12 or 14, something happened, maybe consistently, of something that made them who they are today. And that is, you're always going to be this way, or you're never going to be that way. And when I was 4 and a half, my mother had married a person that was in the Army. He came. And she had another little girl, by the way, from this man that she married. He came to visit when he was on leave and brought my sister a doll and a pearl necklace and nothing for me. It was that moment that shaped my life. I went into the kitchen and an aunt said, honey, don't you worry, that's not your daddy anyway. That Was the moment that shaped my life. I decided I'm going to be so cute, so smart, so everything, that no one could ever ignore me again. And I became an overachiever in life. And that particular incident shaped my life. Many times people will have several different things where they decide they're always going to be this way or never going to be that way. And as I said, I became an overachiever. And actually, it's the best thing that could have ever happened to me because I was able to achieve massive success because I would not let anything stop me. My mother, as I said, was a great role model. When I was 5, she was coming to get my sister and I with a friend, had a horrible car wreck. They had to cut her out of the car. She was in the hospital for 13 months. That's how bad— every bone in her body was crushed from her waist down.
Wow.
It was really, really a sad thing. After 12 months, the psychiatrist came in to tell her they were going to have to amputate her left leg because gangrene had set in. She said, I have to get out of here. I have 2 little girls to raise. And that's the kind of spirit that she had. She was so positive.
She—
we got out of the— she got out of the hospital. We were on welfare. We lived in the Gompers in East St. Louis, Illinois. And though she did not want to be on welfare, she found a government program that taught people with disabilities how to have a new occupation. She was a waitress before. She went to school on a bus, on— with crutches for over a year while her leg was healing, to learn how to be a secretary in an office. This was my role model. So I think it's really important for, for everyone to know exactly why and how a person became who they became. Fast forward, I got married and I had 2 children, and my husband and I had a small store.
One other thing, one other detail. Your— the marriage to your mother's husband didn't work out, so she—
No, no, he died after he got out of the service and said he didn't want the responsibility of 2 kids. So we had no father figure in our house. Good, thank you for reminding me that was an important thing. So she had the 2 children and nothing else.
Yeah.
So again, fast forward, I got married, grew up, got married, had a really wonderful husband. We had a store, and we serviced a lot of peddlers. We had a big cooler in the back of our store, and These men would pick up their produce and then go to wherever their spot was and sell produce. Well, this was a long time ago. I was looking for a way to help my mother and my sister. I didn't want to take away from my family, so I thought if I could do something extra, that would help. So these men, though, I saw these men making a lot of money. More than you could ever make in an office or any other kind, even as a waitress. I said to myself, I can do that. So I bought a big bread truck, and there was a little problem. I couldn't drive a stick shift. But I learned, I learned quickly. I rented an empty gravel lot in Illinois, and I was in business. It was just an empty gravel lot. I learned to drive the truck. I would pick up produce, and then I was in business. Displayed the produce on milk crates and plywood, and I made so much money. You couldn't even believe how much money I made. So I did this for 5 years. Then I was looking— when I stopped doing that, I was looking for something else to do. And so I contacted a father and son who had 3— had some grocery stores, and I asked them if they wanted to partner with me, and they said yes. And our agreement was that they would run the store because they had a lot more experience in retail than I did. And so I take responsibility for this too. I was not paying attention. I was really They were running the store, and I thought, and wasn't watching. And this is one thing that I always say to people, and I'm sure that your audience really does this, but it's really important to not let someone else take care of your business without you watching it. It's really, really important. So I was not watching, so I take responsibility for that. After three or four years, they wanted a meeting. They handed me the keys and said they were declaring bankruptcy. Well, this traumatized me. I did not know what one I wasn't paying attention and really did not know what had happened. So when I got into the books more, I saw that they had siphoned a tremendous amount of money in different ways. You know, they would get buy something and. Charge the store, you know, 5 times or more what the product was. And then they would get one vendor and go as high as they can go and then switch vendors. So a lot of different ways that looked legal, but it was not. And that's how, in today's money, it's equal to really more than $1 million. And by the grace of God, little by little, I was able to turn the store around. I paid off, I paid that money, all of the vendors, to all of the vendors, and so I was solid. I had built a business in the meantime to where there was so much business that people would go around and around in the parking lot and couldn't even get in. So I decided to open a store 3 times the size as the original store. And there again, by the grace of God, I designed that store and did a lot of things much better than the original store to begin with. So this is really, it's an interesting, I mean, I'm giving really the Cliff Notes, so I would suggest everyone read the book. It's inspiring, it will encourage you, and it shows what's possible in life. There are many things that I did That I was not aware that it was creative until after the fact. It was just learning to survive is really what I was doing. So I designed the second store and did a lot of really good things, which again, I didn't realize how good they were until after the fact. One of the things that I did, I wanted it to be a family store, and I had a toy train when I was designing the store. that went around the entire store up above. And I put a train, a G-gauge train, and then I had a flat car on one of the cars, and I had a cardboard piece that had the special of the day.
Oh.
And this train went around the entire store. So parents and men, everyone absolutely loved it. They would go around the entire store. And so all of the end caps were around that. Into our store, which there too was really creative, and I didn't realize how creative. So you had to go past all of the end caps where the money-making really was. So it was really— that was good. That became really such a draw that people even who had company from out of town would come to the store or bring their relatives because it was really so good. It was a community too. I wanted to attract Families, because families really buy more product. So, so many things I did. And I want to encourage every single person, and I'm certain that you know this, but charity is good for business. And that is, choose a charity that you love, not just because it's a thing, but choose a charity that is really good. And I'll tell you what I did, and you might want to do a takeoff. I would every month, I first I made a wishing well that everybody could come in and put money in, no purchase necessary. I chose an organization that was a nonprofit. Every single month I would contact them, I mean they would, they would apply. I would then contact them. They would put it in their newsletter. So these are really good Suggestions. They would put it in their newsletter and say that I would match whatever monies was put into the wishing well up to $400. I then had a big check at the end of the month that the executive director and I would have a photo. They would put this in their newsletter also. This really was really good. I was able to give away a lot of money over the years. And a little at a time, and it worked beautifully. It was really good publicity. I didn't do it for that reason. I did it because I wanted to make a difference in business and in life. It was really one of the best things I ever did, and I would encourage every single person somehow, you know, have a can drive, whatever. Really important to choose a charity that is Of the heart, of what you feel very strongly about. That was really a great thing. One of the other things I did was I saw that there were a lot of Bosnians that just came into St. Louis, and I thought if I could bring something from their homeland to— that they would want, that most people didn't have, you know, it would make them feel at home. I then advertised in their little newspaper in their language, and it was amazing. I started with a, with a, just a pallet of product that I found an importer in New York, brought it in, and little by little, it built into a 16-foot of international foods, which was really a really great also idea. I also saw that they loved Cubanela peppers, which is a long green pepper that we didn't have. I imported that from Chicago and started carrying that. Again, advertising in their little newspaper. And so I'm saying these things because I really would like to encourage every single person to be creative. It's really creativity, you know, find a niche and then fill that niche. And that's exactly really what I did. Again, I didn't know I was being creative. It was really a matter of just surviving and finding new markets.
Mm-hmm.
I brought the Cubanelle peppers in from Chicago, and then I had a farmer that, that grew things for me to grow the Cubanelle peppers. I then sold it by the case. They absolutely loved these Cubanelle peppers. So there's many, many things that I did that was creative, That, again, I did not know about, that I was creative until after the fact and after it worked, actually. So I can stop here for a minute. And do you have any questions for me, Alan?
Well, I think that that's extraordinarily fascinating. You were saying that it was important to be creative. I think another thing that I hear from your story that you really hadn't pointed out here is that you knew your community. You knew, you knew your customers, not just on a customer basis, but you knew about them.
Yes.
Talk to us about that.
My goal when I opened the store was for it to be a community, that people love to come, that it was an enjoyable experience. And actually, kids didn't really want to go to the store with, with their parents. They love to come to the store. because there were things to do, and I would give out cookies and different kinds of things. And so it was a community. We had— I had different events, you know, Red Cross, lots of different kinds of events at least once a month that made it even more of a community. I think what's happened in the world is things and businesses have gotten so big that you lose the touch of Families. And I feel that there's many things that even large companies can do to make the people feel that it's a community or that it is a caring company. You know, many times you are just a number, even employees, and it no longer is like the small community store. Not that big companies can do that, but there are a lot of things they can do. That will make a major difference.
For sure. But what impressed me about this is that, you know, I think that a lot of business owners would, you know, would come to the realization that, well, there's a Bosnia community here and Bosnians are shopping here. And they may have, you know, some realization that Bosnians like this or that or the other. But it seems to me like you just went even beyond that. You not being a Bosnian, how would you know these things about Bosnians unless you knew the Bosnians? And so you knew them beyond just customers. How did you discover all this about them?
Well, I had a customer who came in that was a long-term customer that was originally from Bosnia. And she was telling me that all of these people, they had to— they came from Germany because they could only be in Germany 7 years. And so there were a lot that came to St. Louis.
Mm-hmm.
So I had a customer that told me about this and it just gave me the idea. You know, if I could find something that is Bosnian food, it would make them feel more at home and really develop a new customer base.
Yeah. Well, another thing that you haven't touched on, but you were the head of this organization, this head of this supermarket. So you had to have a team to help you with this.
Yes.
So where did you learn the leadership skills to lead a team of that magnitude?
That's an excellent question. I think my whole life was learning, and my mother was a great example of never quitting, never giving up, always being resilient, making the turn when it was necessary. So I had a really phenomenal role model, and many people do not have. I, and I, by the way, mentor and have a business that I mentor a lot of people in business because I've learned. Over the years some really great ways to really make a difference and to really increase sales in so many different arenas. I'd like to share another event that I feel is really important for your audience, and that is to be creative. I had cheese. I had a huge cheese department. The problem is that I could not compete with the chain stores because My prices were the same as theirs. So I thought if I could make a difference and have cheese that were different, lower price, then I would certainly be competitive. So I found a cheesemaker in Wisconsin, Cheese America actually. My manager, my store manager and I went, and by the way, I had 80 employees. So that was the amount of employees I had. My manager and I went to Wisconsin, made a deal with the cheesemaker that I would buy 2,000 pounds a month. And then I built a room where the girls did nothing but cut, wrap, and slice the cheese.
Mm-hmm.
I was able to sell cheese $2, $3, $4, $5 a pound less than the chain stores, just by doing that. And so I'm telling these stories because I would like to encourage everyone to be creative. You know, just because something is a certain way, Don't accept that. If you want to expand or learn more or grow as a business, be creative is really what— be resilient, you know, make that turn, find alternatives rather than just saying this is the way it is.
Well, lots of great examples there, Tessa, in terms of the creativity and And just finding things that work and just— and putting those things in place, and then— but I mean, you didn't just really stop there. You always embellished just a little bit, just adding some embellishment that made— that was really a tipping point in terms of making the difference there. I mean, like the story you just shared with us about the cheese, you didn't just go out there and find a vendor to supply the cheese for you and then just sell it as the vendor provided it for you. You found a way and a means to make that more personal for your customers by customizing the product according to what— Your customers wanted. Impressive things. What— I mean, you had 80 employees.
Yes.
And so how would you describe your leadership style? How did you come from essentially no experience in leadership to have— I mean, you started off with your own little fruit stand and you were the person there, and you ultimately ended up with over 80 employees to, to manage, take care of, inspire, and keep them as a workforce for you? What— how would you describe your style?
Well, first of all, I love people, and I can be very firm. I could be very firm and never raise my voice. People know. I feel that I've always been a leader. And really developed more and more. I've been self-taught, and still I'm taking courses. I feel it's really important to be a lifelong learner, first of all. I have been into books for— since I've been very young. So I've learned. And really, all of these self-help gurus, gurus, I have followed many of them and really learned and grew to be a leader. I treated people, my employees, as if they are the most wonderful customers we could ever have. I treated them well. I really would, on a PA, when, you know, and by the way, the customers really got into it too. I would say, Pam, it's Pam's birthday at register 4. Everybody wish her a happy birthday. And so people would make a point to go through Pam's aisle and wish her a happy birthday. I also developed a profit-sharing plan because I felt it's really important for all employees to feel that they're part of it. Not, this is not my job, or any of these kinds of things, which can really become serious when, when you're in a larger company, as a matter of fact. So I feel that was probably also one of the most important things. I let them be involved in it and really would say, you know, the more money we can make, and if we would wash the trash or help each other in their job, this is the more money that you can make too.
Mm-hmm.
So I really wanted to involve all of the employees so that they felt That they were part of it. And really everyone did. I could not make people leave. I mean, people would come in high school, work part-time, and then after they got out of college would come. So no one left, which is really a good thing. There are very few people that have held on to people for a long period of time. But no one left. So that—
That's great.
Well, you know, part-time, you know, they— that was just their part-time. I still am in touch with one of the cashiers, for many of the people that work there. So it's really, I feel, helping people feel important is very important, that their contribution is really important. It's not just one person, certainly it's not just me. They were representing me. And again, I'm going to back up to say, I treated my employees as the most important client or customer that we could ever have. And I made them feel— I helped them to feel important, that their part was really important to the whole process of success of the store.
Yeah, you really You not only made them feel important, but you ensured that they were taking ownership and that—
Exactly.
And through your profit-sharing plan, they actually were part owners in the company.
Yes.
And wow, what a record. I mean, recruiting is such a major expense for so many companies.
Yes, it is. There's so many statistics that tell you, you know, it is so much better to keep So much costly, less costly to keep employees as it is to hire and train new ones. That, I mean, over and over again, that is a very costly thing. This is, you know, I love my life and I'm so grateful for so many things and that I was successful. You know, some people can do a lot of things and still not be successful in life. And I'm really grateful, first of all. That's, to me, it's really important.
Well, Tessa has written a book. It is From Outhouse to Penthouse, and I've started the book, and it is a really fascinating story. And you've heard a portion of her story today, but I encourage you to go out and get the book. I guess they can get it through Amazon. Is that—
Yes, through Amazon. And by the way, it's going to be a movie.
Oh, really? Fascinating. Wow. Well, it'll make a terrific, terrific movie as well. Well, Tessa, beyond getting a hold of your book, you offer mentoring and coaching services. Tell us a little bit about that and how we could take advantage of that.
Well, it's a I say it's transitional mentoring. And I'm really contacting— I'm really targeting CEOs because many times they do not have anyone to talk to. And so I have developed processes that really help CEOs really get more balanced because many of them work far too long and many other things. And really, it's a work-life balance, not just work. So My company is called No Limitations Ever. That's an LLC too, No Limitations Ever. And many times when you are a certain place in life, you really have so much going on that you don't have anyone to talk to. And so I feel strongly, I've been very successful in helping a lot of people over the years and still do. Of getting them to the next level and having it fun, not just work, work, work all the time. So I have a process that helps many. It's called C.A.N.C.E.L. And so I have many processes that help anyone actually to get to the next level of peace, the peace that passes all understanding in their heart, and learning to trust, learning to let go of of constantly being oversight, so many other kinds of things, because I've learned so much over the years and I'm really grateful. So it's really important to pass it on.
Absolutely. Well, No Limits Ever, No Limitations Ever.
No Limitations Ever, yes.
And is that, is that the website we go to?
No, it isn't. I have a website for my book, which is tessagreenspan.com. And if anybody wants to email me, it's tessa@tessagreenspan.com.
Okay. Well, Tessa, wonderful conversation. I'm so grateful you were with us today, and I know our audience appreciates knowing your story and knowing you. So, folks, take some time to get to know Tessa. Reach out, get her book, and reach out to her Uh, in any way that is appropriate. Thanks, Tessa, for being with us today.
Thank you, Alan. It was really great. Appreciate you.
Thank you. Okay.
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