Kristi Winfree - Building A Legacy One Transaction At A Time


Kristi Winfree is a former teacher that discovered she has a passion for helping people and loves to use her natural gifts of being highly detail oriented and implementing systems and processes. She launched Legacy Transactions to help agents grow their business and provide education to them along the way. Her personal motto is "wake up every day to create Raving Fans and make someone's life better!" She is also the host of "Not Just A Daydream - Business Insights and Inspiration for the Work At Home Entrepreneur"

In this episode hosted by Mike Swenson, we discussed:

  • How Kristi found their true calling in helping agents with productivity and training.
  • How Independent TCs prioritize working with higher-producing agents to maximize financial stability.
  • How Kristi grew their team from 1 to 6 transaction coordinators in 2021, prioritizing growth and service quality.
  • How setting boundaries, have proper expectations, and educating your clients are important to exceed their expectations.
  • How Kristi transitioning from a steady job to pursuing real estate and transaction coordination.
  • The importance of setting boundaries and having downtime to avoid burnout in real estate.
  • Tips for effectively balancing a side hustle with entrepreneurial pursuits.


00:00- Intro to Kristi's Career
01:32- Finding her true passion in transaction coordination.
05:48- Independent TCs to financial stability.
10:48- Importance of Setting boundaries
13:11- Having downtime to avoid burnout in real estate.
17:53- Passion to become an Entrepreneur
19:10- Personal story of a team member who pursue being a transaction coordinator.
22:16- How to Find Kristi










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Minnesota Real Estate

Read the full transcript here:

Mike Swenson
Welcome to The Real freedom show where we inspire you to pursue your passion to gain time and financial freedom through opportunities in real estate. I'm your host, Mike Swenson, let's get some real freedom together.

Mike Swenson
Hello, everybody, welcome to another episode of Real freedom talking about building time and financial freedom through different opportunities in real estate. And one of the reasons why I started this podcast is, I really love highlighting different stories from different entrepreneurs inside of the real estate space. Because we're all different, and we can follow different paths. And so as you listen to these episodes, my goal is is that you would find somebody that you connect with, find a path that really resonates with you and see that opportunity and pursue it. And so today, I'm excited to have Christie Winfrey on and she is the owner of legacy transactions. And so she does transaction management, she has her own company. She's also a podcast host, not just a daydream, and we'll talk about that a little bit too. And you live in Texas. So yeah, we'll talk about kind of your journey as an entrepreneur, and then really, to how you can help other people in their journey, because part of growing and getting better and adding more to the bottom line is having good administrative support. And so we can talk about that. And so welcome to the show. Christy. We're so excited to have you. Thanks, Mike.

Kristi Winfree
I appreciate it. I'm excited to be here. 

Mike Swenson
Well, why don't you just talk a little bit about your journey, you know, leading up to before you got into real estate before you got into transaction coordination. And we'll go from there.

Kristi Winfree
So I feel like my my path has kind of windy and there was like, not like a straight and narrow path, you know, to to this position. So you mentioned not just a J dream, and I, I created that podcast, kind of because I've always been a daydreamer all my life. And I've always had, you know, dreams and aspirations of how I wanted my life to look. But I feel like throughout my 20s and early 30s, I really didn't know what path to take career wise. And I read a book called 48 days to do the work you love. And he mentioned in there, basically, think about the kind of life you want and design your work around it. And then he really challenged you to focus on okay, what are you? What are you passionate about, and at the time, I knew I loved music, even though I'm not. I don't know if I'm musically inclined, because I haven't like learned to play an instrument. But that is a goal. And then I thought I would really enjoy real estate I read that book Rich Dad Poor Dad right after college and knew that I would eventually want to get into real estate investing. And so I was torn because I was like, Okay, I think I would love both of those things. And I was living in Houston at the time, I was like, Okay, well, if I wanted to go into music into the music industry, in some form, I probably made the move to Nashville that I felt like real estate was probably the more logical, made more sense. And I could go ahead and pursue getting my real estate licence. And it wasn't a massive investment upfront. So that's what I did. And I started taking the classes and absolutely loved it. And so I get it, I got into real estate almost 10 years ago. Now. That was an agent my first year, but I quickly discovered that I was better. I really enjoyed helping agents and training and mentoring and helping them with you know, their struggles, versus trying to get a buyer and seller. And so I ended up shifting into becoming an assistant productivity coach at Keller Williams that those next next year and a half. And then then I found my true passion and transaction coordination. And that's what I've been doing since 2016, I believe. And so yeah, that's kind of how I got here. But it was, like I said, it was kind of a windy road. It wasn't, this is what I'm going to do and and go for it.

Mike Swenson
Now in terms of starting your business and finding clients. How did that work? Were you still doing some of your own production to offset that? Or did you just jumped in and started serving clients? And then how did you get those clients? I'm curious to see how that works. Because I know for a lot of admin people, they love supporting people. And so sometimes it's a little bit of a challenge to go churn up business and reach out and put yourself out there to find people.

Kristi Winfree
Absolutely. So when I first started doing transaction coordination, I had actually joined a friend's team. And I was with her probably four months or so. And it just wasn't quite working out. So So I ended up going out on my own. But I had a few clients with her whenever I was on that team. But by doing those transactions, I was picking up clients from the other side of the transaction and then also people who already knew me in the industry who had been around Keller Williams, they they knew now knew I was doing transaction coordinators so I started picking up clients that way as well. But yes, the the TC side of things, you know you can be really gifted and detailed and know the process but if you're going to be an independent contractor that is still a piece of the puzzle Do you do have to go out and get clients?

Mike Swenson
Yeah, they hear about you and they want to reach out to. And sometimes there's a challenge too. And as transaction coordination has gotten more and more competitive over the years, it's more difficult to differentiate yourself versus, you know, there's a while ago, where it was more widely accepted as a way versus hiring a full time person, I just love the versatility of that we've used third party folks in the past to because it's nice, where you don't have to have a salary and when when things are seasonal, then that's something that you have to work through on your end, which is an additional challenge to come through where they can send you files, they might not, they might decide to go with somebody else, or they might take two months off, and you still have to continue to bring in money. So it kind of talk about that cash flow management or even just building and growing and kind of getting that stable income. How did that work for you? Or what challenges did you have to work through?

Kristi Winfree
Yeah, I mean, I think that's the challenge for independent PCs, just like it is for agents, because like you said, our businesses, seasonal agents, business is seasonal, and so as buyers, and we are depending on the production of those agents, so it is really important that as much as we can, we definitely want to work with those higher producers. And I know I do get a lot of referrals. And a lot of those referrals are some are newer, newer agents, I get a lot of referrals from brokerages, because I'll refer their new agents and say, hey, you know, have this transaction coordinator help you because he, they can teach you the process. And those are fantastic. We absolutely love new agents. And we get a lot of the mentoring of for my financial standpoint, and probably not necessary profitability, but a financial standpoint and making sure that we are able to cover all of our expenses, we do have to also work with agents who are producing a little bit higher. So those are things that you have to take into account and actively seek out those agents.

Mike Swenson
It's kind of like working with first time homebuyers, you enjoy them. But you also have to educate them through the process. And so if you take on a lot of new agents, that's going to suck up a lot of your time, but you do a good job with them. Hopefully, you have a client for life, because they want to just continue to use you as they grow. But they may not have a lot of transactions right at the beginning,

Kristi Winfree
Right. And we have found that sometimes those are our biggest, like raving fans and supporters, they are so grateful for the training and mentoring shift that we've done throughout the transaction, they tell everyone about us. And so you know that that warms my heart, it's like multiple passions, right? It's another piece of the passion that that I absolutely love is to be able to help those people. And now they're referring us even more, we also have to take into account that you can only work with so many agents. So if we take a bunch of clients on, you know, whenever maybe in the silver market hits, when the busy market hits, and all of a sudden you've got, you know, a tonne of files to you have to think about okay, well, I'm busy right now. But how busy am I going to be in the spring and summer market? 

Mike Swenson
Yeah, because if you're at capacity in the slow season, that's going to really spike and so you have to come up with ways to handle that either extra hours or find additional people to help serve your needs. So talk through that growth, then because I know you have more than just you. And so how, how did that happen? And where are you at with the growth as a business owner versus just being a transaction coordinator for people.

Kristi Winfree
So I have a team of six now. I would say really my first few years, I did it on my own other than having a part time assistant. And then and then you know, they slowly grew into a full time assistant, but it was really 2021 when my team started taking off. And I will say those years before or especially 2020 2020 was extremely hard because as you all know, or everybody knows the real estate market just like went crazy after that couple of months that the world shut down and then all of a sudden it opened back up. And I didn't have a whole lot of support in that moment. So that really pushed me okay, like Chrissy you got to start building a team, because I had agents who were referring me business and they were really busy. And so I didn't want to lose any agents. I didn't want to lose any agents because of service. And thank goodness, I didn't, I still gave, you know 100% raving fan service and but I didn't want to have to stop growing our business either. So that's whenever I decided, okay, now now I needed to bring on another transaction coordinator. And so I was diligent about those years before I started documenting all my systems and processes through like loom videos and creating an Operations Manual. And I knew that growth was in my future. And I would say that I was strategic about that because I knew how hard it was going to be to train somebody whenever I if I really desperately needed somebody in the moment. It's so much harder to train at that moment if you don't have those systems put in place. So I had started putting those systems in place. And so when I brought somebody on, I had basically like a structured training four week training programme, okay, this is what we're going to work on this week, this next week. And then by the end of the four weeks they were truly trained on the whole transaction process and then I just duplicate that process over and over. So I brought on like three, three new GCS in 2021. And I think another VA as well, and others, there's the six of us,

Mike Swenson
It is certainly a challenge, because the seasonality is difficult because like you said, it's, it's tough when you're in those really, really busy seasons, you don't want to over staff, and then in the slow seasons, you want to try to grow your business. And it's a difficult thing. And so I know for some people, you know, if you're a transaction coordinator, and multiple states will, maybe you can find a way to balance that out a little bit based on the states that you represent. But it absolutely is a challenge. Talk about setting boundaries, setting expectations, follow my processes, even though you may have done things different talk about how you're able to educate your clients, and then get them to hopefully follow what you would like to have them do to help your systems that you've created. Yeah, absolutely.

Kristi Winfree
That's such a good point, too, because I would say my first like two years in the business, I did not have good boundaries. I wanted to serve, I wanted to be all things to everybody. And that's just not possible. So I now know that by setting proper expectations, and having that conversation in the very beginning, when we have like a consultation, I am truly able to give raving fan service, because if they know what to expect and what we do and what they do, there's no blur, blurred line. And so that's whenever we can truly exceed their expectations. Because I had that conversation to the very beginning. I would say I'm a people pleaser, like or recovering people pleaser. I want to be all those things to everybody because I want to truly help and serve. You know as much as I can. That was hard setting those boundaries. And I think for a lot of TCS, we are that like SC personality a lot of us are if you're familiar with a disc, and so a lot of us just truly do want to serve and so sometimes this conversation so hard to have, but for any admin TC out there listening, I would definitely encourage you to have those conversations. Because when you read a phrase, the way you think about it, it's not like it's not a hard conversation, or it's not something that disappoints somebody, it's just truly saying, This is what we do, this is what you do. And you can serve them better if you do that.

Mike Swenson
We talked about it, you know, you teach people how to treat you. And when when I was training admin staff, I wouldn't say you know, look, you can choose to respond to an email at 8pm on a weekday. If you do that, just know that agents probably going to think, oh, they respond to my emails at 8pm on a Wednesday. So you think you're doing them a favour by being responsive after hours. And now that's something that maybe intentionally, maybe unintentionally, they're just like, Oh, she's going to respond back because she did last time. And so that's a difficult thing. And so even maybe timing your responses to send out at 8am The next morning, that's a way that you can do that. And it's difficult to it's because agents sometimes are used to working all hours of the day. And so they just think well, why can't you and it's just maybe you don't want to write maybe you don't want to maybe you need your your batteries recharged by being able to unplug at a certain time. And so it is difficult for folks that aren't that same way as you and wiring to understand that, hey, that might work for you. That doesn't work for me. And for me to be at my best. I got to recharge the batteries to recharge the batteries. 

Kristi Winfree
I got to turn off 100% Yes. And like you said, you know, if you respond after hours, and you think you're helping them now they they've had that idea of okay, well, maybe she'll respond again. And then if you don't respond the next time, then it could be disappointing him and then you know, and then that's where it's creating a blurred line. And so if you're firm with your with your line then like I said, then you're not potentially creating a situation where they'd be upset but but yes, I mean, everybody at Jim's include included need to have downtime, and I know real estate can be a 24/7 business and but even agents need to have like a day or, or some time where they take off and they're not responding to emails, text messages, phone calls, because you'll get burned out. I mean, you can't work 24/7

Mike Swenson
You got to have the long term mindset there of Yes, I might be able to do it for now. But if I want to be in real estate for a long time, I want to create a schedule that's going to work for me long term. Absolutely. Yeah. So talk about now in terms of your life goals, how has this fit in well with that assuming you know kind of going back to that person of still trying to figure out what I'm doing now you've got a business that's hopefully accomplishing what you want to accomplish for people that are out there and like I don't know if I want to make the jump or I don't want to leave the safe stable w two lifestyle talk to that a little bit about the potential rewards on the other side and yes, there's a whole different set of challenges that come with it but hopefully being in your in your sweet spot

Kristi Winfree
I would say I never could have imagined that it would be this good. I mean yes, we all have bad days and and there's challenges just like you said, but when I left a steady job and you know started pursuing real estate and then whenever I got into the TC side of things, and being an independent contractor income is you know, it It's not as it is a steady income, but it's not a steady income, if that makes sense. Like it's we fluctuate with the market next month is super, super slow for me. But you know, the past few months have been pretty good. So it's not a consistent income anybody that can say that that way, but being a TC owning TC company has allowed me to do things that I would not have been able to do before. So, for instance, in 2019, I decided that I just wanted to move to Nashville just because and you know, didn't know anybody there, but it was gonna take the risk. And I wanted to explore something new. Because the transaction coordination role allows me to basically live and work from anywhere, as long as I have my computer and internet, I could do that it's allowed me to start, you know, mentoring others, I never expected to have a team of a team, below me at all. But now, having leading a team of six, that's amazing, I've gone I've been able to go through IVF the past year, and everybody knows how expensive that is. So I would have never been, I don't think I would have ever been able to do that if I had not started this career that's allowed me financially to be able to do those things. And then like purchase my house and 2020 all on my own. And you know, it's just been, it's been a lot of great things. And now I'm moving into a new, I don't want to say a new side of the industry, but I'm adding adding more on to the TC role, because I have a passion to that I do want to coach and mentor other transaction coordinators who are just getting into the business, or who have been in the business a little while, but want to enhance their skills and learn how to run the transactions better. So they can manage more, but still have that that raving fan service. And so now I'm creating an online course that they can take that teaches them from A to Z, how to set up the business, how to get clients how to run transactions. And then I've got, you know, my checklists and email templates that they can purchase. And then also an air table template that is like a system that to basically see all your transactions at one place. And to know your numbers, your production numbers, your agents, production numbers, all at a glance.

Mike Swenson
Yeah, I mean, you get to really build your business, however you want to do it. And if you wanted to tell a client, you don't want to work with them anymore, you get to do that. And so you get complete control and say over how you run your business. And the challenge sometimes can be looking over your shoulder looking at other business owners in the similar industry or other transaction coordinators, and you might think, Oh, I'm not growing as fast as them or oh, they're doing this and comparing yourselves to others. But the reality is, is you can put blinders on and choose to run your business how you want to run your business. And we can talk here about starting a podcast like you can do that if you want to. And if you don't want to, that's okay, you get to decide how to do that. And so, yes, it comes at a cost to other things, maybe that stable paycheck, but you never know when that stable paycheck could just get pulled away from you too. And so being able to bet on yourself and build your own career that can't get taken from you in the same way that a job could or a paycheck can

Kristi Winfree
Absolutely I would rather any day I'd rather be building my own dreams than working for somebody else and building their dreams. And we need the people who do want to work for other people. I'm so grateful for my team that they do want to work for me. But I think everybody's wired a little differently. And so for those who have that passion in their heart to become an entrepreneur, I would say lean into it, and do what it takes to follow that dream. And you may not be able to like necessarily leave your nine to five right away. Or you might just have to give yourself a runway of have some savings before you step out. Whenever I did start my TC business. I was waiting tables on the side for the probably first six months until I had enough income coming in from the TC business to be able to finally step away from that. And so sometimes, yeah, you might need a little bit of a side hustle to make it until you have enough

Mike Swenson
Well, and even to you running your business, I would think the goal for you is you get to then employ people who come to a job that they love that get treated in a way that they love, get the support and the career growth that they love. And so yes, that person is still choosing to work at a job but you get to be hopefully the model boss, the model company that they're looking for that they can't find in another place. That's my goal of the people that I hire them I want them to love what they do and love working for me and love the support that they're getting in the care that they're getting versus other places where they might not get that

Kristi Winfree
Absolutely to be able to change their life is just amazing. I remember one of my team members, she said that. She left teaching to pursue being a transaction coordinator and had no real estate knowledge at all. And I was able to train her and and now she's an amazing transaction coordinator. But she said how impactful it had been for her to be able to switch to this career because now she can be at home with her kids when they get home from school. She was able to like she had enough energy to be able to pray with them in the evenings before they went to bed. And like when she was a teacher, she was just so mentally drained. And so that was just like, made such an impact on me to know that by me pursuing my dream and taking a chance and betting on myself like now I'm able to I'm not just influencing her I'm employing serving her family and her children.

Mike Swenson
Have you ever heard the phrase you're the average of the top Top five people that you hang around. Well, real estate agents, I'm excited to increase your five with you. We're launching the real freedom investor agent tribe to help you get educated and connect with others to build your real estate investing journey, and also to help you along the way as you're working with real estate investors. So come check it out on our website, real Go to the store, we have a membership. We have a mastermind group and private coaching to help you stay accountable to your real estate investing goals. And to make sure that you connect with like minded people to accelerate your progress. And to cheer you on along the way. Check it out real Click on the store that talks about your podcast, not just a daydream, how did that come about? And what are you looking to do with it,

Kristi Winfree
I knew I wanted to be inspirational, motivational. And the goal is to truly just inspire other people to step out and take that risk and bet on themselves to follow their dreams. And so it took me forever to come up with that name. But I have this t shirt that says Daydream believer that I absolutely love. And I just kind of clicked one day of not just a daydream because it's about taking the actions you need to chase those daydreams and not let them be just daydreams. But actually turning them into, you know, your, your passion and your goals and move forward towards them. So it's truly just about entrepreneurship. It's not necessarily specifically to real estate. I've interviewed so many different people doing all types of things from financial planners, wedding planners, coaches. And so I have guests on the podcast, and then I also have solo shows, and I try to keep it 45 minutes or less that way, you know, people can hopefully listen to it on their way to work or dropping off the kids at school, and, you know, get some inspiration, and hope I would love to hear stories about people who said, Hey, I took that risk. And this is what I'm doing now.

Mike Swenson
Awesome. And I think people more and more seeing the reward on the other side of that I think our society entrepreneurship has certainly grown to where people see that value. So I love that you're highlighting that for people that want to learn more about you're doing the courses that you've got going on the support that you're doing to help people build their own transaction business, but then also the support you're providing to help them grow their real estate business through transactions. How can people find you? 

Kristi Winfree
Absolutely, you can find me at Christine Winfrey on Instagram. And then Christine will give more information about my courses and the checklists and email templates airtable template that you can, you can find and if you're interested in our transaction coordination services, we're in Texas, so we only serve Texas right now. But if they can reach out to me on Instagram and I'll be happy to talk to them.

Mike Swenson
Well thank you so much for coming on Christy and sharing best of luck to you in your future and being able to design your business however you want it to be. Thank you so much. It was a pleasure.



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