Chief Milestones
Chief Milestones is a business podcast exploring how founders and parents build meaningful companies without sacrificing their health, families, or values.
Through honest conversations with entrepreneurs, investors, parents, and next-generation leaders, the show dives into the real milestones that shape business, wellness, and life.
New episodes release Tuesdays and Fridays.
Chief Milestones
Triplets, a Crash, and a $50k First Deal | Lynn Schwarber | Part 1
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This episode isn't about real estate advice.
It's about what it takes to start a commission-only career the year after the housing market collapsed.
In Part 1 of this conversation, Lynn Schwarber - agent with Comey & Shepherd and investor in long-term and short-term rentals - breaks down how she went from 20-year TV news anchor to full-time agent in 2010, right after the crash, with newborn triplets at home.
This was not a career-change story.
It was an income-risk problem.
We cover:
- Why she left two decades in journalism to bet on a fully commission-based business
- The math behind starting full-time the year after the housing market bottomed out
- How a routine house showing turned into a one-hour bidding-war decision - and her first Airbnb
- Why 75% of new agents quit in year one, and what separates the ones who don't
- Why she's now cautioning against short-term rentals in markets that have gotten crowded
If you're building something with no guaranteed paycheck, or making a bet on timing you can't fully control, this conversation will feel familiar.
This isn't a highlight reel.
It's a practical breakdown of how a real operator built a business under pressure, not in hindsight.
Reach out: ChiefMilestones@gmail.com
Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.
New episodes release Tuesdays and Fridays.
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Meet Lynn And Her Big Family
Lynn SchwarberI'm Lynn Schwarber and I'm a real estate agent with Comey and Shepherd. I had triplet boys. They're 22 now, and my daughter's 21. So I had four babies in a year and a day. So you got in in 2010. Yeah.
Reshma VadlamudiSo what was that like?
Lynn SchwarberThat's a good question because the crash was in 2008. So it was really a difficult time to start in real estate. Once I was walking through a house and it was a kid's room, and they had written on the wall, I loved this house. You know, and they still had some other toys and drawings around it. Just you're just so sad. You know, so it was a really difficult time for so many people back then. But also when you have a time like that, there's so much opportunity. My very first property was a bank-owned, it was a foreclosure condo in Westchester that I got for I think $50,000. And they sell now for $200. Had that for a while. It was a great rental. And same thing. Sold that, took the money, bought something else. I'm Lynn Schwarber, and I'm a real estate agent with Comey and Shepard. So and you also invest. And I invest, yes. I have some rental properties, including um a couple of short-term rentals. So yes. Yes, okay. And a mom of four kids in college. Yes. Yes. Yeah. Not as busy as you with little ones, but yeah. You were busy. I was busy. Yes. I had triplet boys. They're 22 now, and my daughter's 21. So I had four babies in a year and a day. They're a year and a day apart. So yeah, it was crazy when they were little, but a lot easier now.
Reshma VadlamudiYeah. Yeah. So what month were they born in? What is the November?
Lynn SchwarberNo. Just yeah, right at the holidays. So right at Thanksgiving. Yeah. So yeah, the boys are, yeah, the 25th and Katie's the 26th. So we got Thanksgiving, then Christmas, it all all yeah, at the same time. Yeah. Yeah. Crazy time.
Reshma VadlamudiYeah, it's crazy year for you.
Lynn SchwarberIt's a crazy time of year. Yeah. Yeah. Busy, busy. A lot to be thankful for for sure. Yeah.
From TV News To Real Estate
Reshma VadlamudiYeah. Okay. So tell us, how did you start in real estate? What were you doing before real estate? And how did you start in real estate? Okay.
Lynn SchwarberWell, I was um a TV news reporter and anchor for more than 20 years. So I'm from Philadelphia. I went to Temple University, studied journalism, loved journalism. I mean, I it was my passion. You know, I worked in Philadelphia and Delaware and Maryland and radio and TV. And I came to Cincinnati for my job at Channel 9, the ABC affiliate here in Cincinnati, WCPO, and I loved it. So every day it was something different, you know, because you're a reporter. I was out there covering anything, you know, big stories, you know. Um the tornado came through, you know, big car accidents. It was usually tragedy, you know. So it got to be a little depressing, shootings, you know, murders, I mean, all that kind of stuff. So um, I mean, it was exciting, I loved it, but after a while, I started to get kind of burnt out from it. It's just a little depressing. I had kids, then I had my babies, and uh at that point I actually left because I was home because I had triplets, newborn triplets. So I left at that point, stayed home with them, had my daughter. So I was home for about two and a half years, full-time mom, and then went back part-time. So then I had a really nice mix of part-time, you know, work at Channel 9, a couple nights a week reporting, and then home with the kids most of the time. That was great. So I love that. But then I went into real estate because I thought this would be something I could do. All the kids are little, I could do it as much or as little as I want, really flexible. So, and I loved it. I mean, I always had an interest in real estate. I bought my first investment property uh back then uh with a realtor friend of mine, and she was the one that said, You would be really good at this. You should, you should maybe look into doing this. I was like, Yeah, maybe I will. I bought a two-family in Oakley, great property. Uh, my mom lived in the first floor, and I had a tenant in the second floor, and the tenant's rent paid for the entire thing. So my mom didn't have to pay anything, you know. So anyway, worked out great. So I went into real estate.
Reshma VadlamudiWhile you were doing while you were part-time uh in 2009, yeah.
Lynn SchwarberSo I kind of did that while I was still part-time at Channel 9. Then I got my license. And then beginning of 2010, I left uh Channel 9 and I decided to go into real estate, like pretty much full-time. I joined a team, Sandra Peters, she was the number one agent at the time in the whole state of Ohio, not just Cincinnati. So I was with her for a couple of years, learned a ton from her, and then I went out on my own. And um, the first couple of years are really hard when you get started in real estate because it takes a while to get going. You know, people don't trust you until you have a reputation, uh, even though they knew me from the news or whatever, like, well, you know, what houses have you sold? What have you done? So it it takes a couple years. Um, but once once it started, it really took off. Yeah. So it's been busy.
Reshma VadlamudiSo you got in in 2010. Yeah. So what was that like?
Learning In The Post Crash Market
Reshma VadlamudiI only heard yes.
Lynn SchwarberThat's a good question because the crash was in 2008. So it was really a difficult time to start in real estate. So it was a lot of short sales and foreclosures happening at the time. Um, I mean, I did them. I did, and it's a lot of work. I mean, a lot of short sales that take forever. It was sad. I would go through houses with people, and people had just left them because they were underwater. They owed more than the house was worth. So they would just give up, stock paying their mortgage, live there for free as long as possible till they were, you know, evicted and it became bank owned or and and the houses would just be trashed. And I once I was walking through a house and it was a kid's room, and they had written on the wall, I loved this house, you know, and they still had some other toys and drawings around. And just you're just so sad, you know. So it was a really difficult time for so many people back then. And but also when you have a time like that, there's so much opportunity because the housing prices were so low, and then the interest rates, you know, dropped. So I wish if I could go back in time that I could have bought a hundred properties because now those properties that were selling for 200,000, you know, are 400,000. It was just crazy the difference. Yes.
Reshma VadlamudiAnd what was the first house that was that you brought in Oakley? What did you pay for it back then?
Lynn SchwarberOkay, so that was that was a really nice 100-year-old two family in Oakley, um, a lot of character, hardwood, stained glass. And I believe it was like 220,000 or something. Wow. Yeah. Um, and those same houses are selling now for like at least 450. Yeah. Yeah.
Reshma VadlamudiYeah.
Lynn SchwarberSo I sold that one a while back and I took that money and bought a different property up in Liberty Township that was a rental. Um, because I was afraid with the old house, you know, all the things that can go wrong. Yeah. But anyway, it was a good investment for sure. Yes. Yeah. So you traded in.
Reshma VadlamudiRight. Yep. Traded for something else. Um and that's how that's how real estate works. Uh onto the bigger and better deals.
Lynn SchwarberExactly. My very first property was a bank owned. It was a foreclosure condo in Westchester that I got for I think $50,000, you know, and they sell now for $200. Yes. Um, had that for a while. It was a great rental. And same thing. Sold that, took the money, bought something else. How did you know that by bank owned like it was that one was listed as a foreclosure? It was actually already bank owned and on the market as a foreclosure. Okay.
Reshma VadlamudiSo you found it on the market, on MLS. It was on the MLS. Okay.
Lynn SchwarberAnd being a realtor, of course, I would see it immediately as soon as it came on. Yes. Yeah. Yeah. Yeah. There those deals are really hard to find now. You're not seeing those kind of deals now. Yes.
Reshma VadlamudiSo you were you were an investor first and then you became an agent, right?
Lynn SchwarberI guess I was, yeah, because I did buy that investment, the Oakley property first and then became an agent. Yeah. And then bought the uh condo and then just kind of went from there. Yeah.
Trading Up With Rentals And 1031
Reshma VadlamudiSo you started in Oakley, and then are you still in Oakley, like Hard Hyde Park, all those areas?
Lynn SchwarberAre you No, um, no. So I live in W I've lived in Westchester for 25 years. So I decided I I really didn't want to drive down there to manage my rentals. So when I sold that one, I bought one in Liberty Township, and all of my my rentals would be Liberty Township, Westchester, Mason. Yeah. So, and then as you know, I sold just in the past couple of years, really sold a couple of my other long-term rentals, took that money, did a 1031 exchange, and then put that into uh a short-term rental. So I have two in Mason, and the returns on those are so much better than the long-term rental. I wish I had done that a long time ago. You know, yeah. Yeah. So they're doing really well. Yes.
Reshma VadlamudiSo for what made you switch the gears from long-term rentals to short-term rentals?
Lynn SchwarberWell, um, you know, a funny thing is working with you and you were buying your short-term rental in Hamilton. I think that was your first one.
Reshma VadlamudiYes.
Lynn SchwarberAnd and that that kind of inspired me, honestly, seeing what you did. I was like, well, you know, that's a really good idea. You know, doing Airbnb and finding the right spot for it. So it was kind of in the back of my mind. You know, no, I knew some other people that were doing that. And I thought, maybe I'll do that eventually. So it was the the seed was planted, and then I was showing someone this house in Mason, and it was last minute, showed it to her that afternoon. It was a bidding war, really super cute house right near downtown Mason. It had been totally renovated. It was, she was out of her, she she didn't want to bid on it. It was getting too high. And I walked in there, and you know how you just have that gut feeling. And you know, that's one thing. It's like you have to follow your gut and that little inner voice. I walked in that house and something told me, like, you need this house. This is your house. Like, you need to buy this house and make it an Airbnb. As soon as I walked in, I was like, oh my gosh, this would be a perfect Airbnb. Um, so I called the agent. They're in multiple in multiple offers, accepting highest and best by whatever. I had like an hour. So I went to the coffee shop, had my laptop, did the, you know, the offer. Luckily, had some financing I could hurry up and get in place and um and put the offer in and and I got it, you know. And uh, and I'm so glad that I did that. I had no idea how how good it would do, like if Mason was even a good market for an Airbnb. And um, and it's been great. It's and it did so well that that's why I bought a second Airbnb in Mason. So yeah. Yeah. And it's so much fun. I love, isn't it fun? I mean, you buy the buy the property, then you decorate it, you know, you make it a great place for families to come stay.
Reshma VadlamudiAnd it's also a hospitality touch. Yeah, like it's like you feel like you're providing something, it's not just a rental, right? You feel like you're connected to it.
Lynn SchwarberRight. Like I just had a family uh stay at the it's called the Cozy Bee Cottage, and I decorated it like with bees and stuff. It's really cute. Um, and the family that was just there, her daughter had just finished her cancer treatment at children's hospital for brain cancer, and the whole family had flown in from like three different states to be at the house to celebrate with her. You know, it's like, oh they are like I'm I'm so so glad that they could be there to do that together at the house. You know, yeah.
Reshma VadlamudiI I heard similar story for one of our Liberty houses, and I was like, every time someone comes there and uh someone like from Kentucky came down just to celebrate that it's like her last treatment, and it's like she is in remission now, and that's like even though it's not the total end of it, but they're like very hopeful. And I was like, every time I hear that story, oh gosh, it it's like chills.
Lynn SchwarberI know. And it's like, oh, I'm glad that my property can give them that kind of comfort. Cause who wants to be in three different hotel rooms? It's not the same. Yes. You know, and they can sit by the fire pit at night and hang out with the colours. And yeah, play games and you play in the game room, and so yeah, you feel good, like you're providing something for the community. And yes. Um, so yeah, so I really enjoy that part of it. Yeah, too.
Reshma VadlamudiYes. Yeah. Yeah. Okay.
Why Most Agents Quit Early
Reshma VadlamudiSo everyone talks about real estate, but not everyone laughs. So what's the secret? You know, it's funny.
Lynn SchwarberI was just looking at a statistic from the National Association of Realtors just yesterday. It came out in an article, and it said that uh across the country, 75% of real estate agents drop out in their first year. In their first year, 87% within the first five years. So most agents don't make it. Yeah. And it's sad, but it's because I think they they have the impression it's easy. You know, I can just get it, make some big, make some money quick. But um, it's hard because, you know, first of all, you have to build that trust. You have to have it takes a couple years to get the reputation, to know what you're doing. You can't just do it part-time while you have a a different job. Uh the good agents really are in it full-time, know the market, you know, they know the strategies to use in negotiation and know the people to call. I mean, there are so there's so much to know. And I I think it's it's hard in the first couple years to do all that. And so people would kind of drop out. Um, so the ones that last are the ones that uh really know how to self-regulate because you're self-employed. You know, you have to be disciplined every day. Work, you know, work nights and weekends and make calls and keep the relationships going and have the context and the networking. And you don't get paid unless something sells. So you could do a ton of work, you could drive people around looking at a hundred houses, you don't get a dollar, you know, unless they actually buy one. Yes. And it can get frustrating, you know. But I love it. And uh and it it kind of just it becomes addicting, you know. So for me, luckily when I started, I was married. My husband was the sole, he was the main provider back then. So I was I had the flexibility so I could start slow and build that, you know, which was great. And then it took off and then it can kind of take over your life, yeah. You know, if you let it, yes. Yes, which I let it for a few years was a little bit too much, a workaholic, yeah, yeah. Not healthy. Yeah.
Mentors Lenders And A Trusted Rolodex
Reshma VadlamudiOkay. So someone listening to this, wanting to become an agent and have zero contacts in real estate. Right. If there are two things that they can work on right now, what would you tell them?
Lynn SchwarberWell, I mean, I think the networking is huge, you know. So, number one, when you get into a brokerage, like find a mentor. If you're not on a team with a with a lead agent that can guide you, you know, find some other agents that have been around a while and you know, go to lunch with them, kind of learn learn from them and their experience. So, and and then also there are a lot of events you can go to, networking events or different lenders. You need to have, first of all, you need to have a Rolodex of contacts, you know. You need to have a a few, at least a few really good lenders that you trust that are great, you know, and go have coffee with them, learn from them. Hey, send me information on your loan programs. What do you have for first-time home buyers? What do you have for veterans? What do you you know? They have all kinds of programs. So you really have to educate yourself on all those things and who what lenders do what and have them in your phone. You can call them immediately. So if you're at a house with a client, oh, I got a lender that specializes in VA loans, let's call him real quick. You know, so and and then your client's impressed. Oh wow, you would, you know, and then ask other uh agents who they recommend for, you know, electrician, a plumber, a roofer. I have all these guys that if we're in an inspection and we're worried about the roof, let me call Jason real quick, my roofer. He'll pop out tomorrow and look at the roof. So you need to, you know, really work on those contacts and having those associations. So and that really will it helps, you know, then you're an expert.
Reshma VadlamudiYeah, so first thing is mentor and then start going out with the lenders and uh and maybe talk to more agents and find that start building that roller soft, yeah.
Lynn SchwarberRight, yeah. Of con of of contractors and people that you trust, you know, to handle your clients. Yeah. Yeah, to make you look like the expert, you know, that you have all these contacts. Yes.
Investing Edge And Market Saturation
Reshma VadlamudiSo yeah. Now you're an experienced agent. So how did like being an agent give you an edge with your investments?
Lynn SchwarberWell, you know, I am in and out of houses all the time being an agent. So it probably does naturally give me an edge with investments. Well, like when I walked in the Mason house. Yeah. It wasn't just out of the clear blue sky that it I thought, oh, this would be a great Airbnb. You know, I'm in and out of Mason houses all the time. I know what's a good area, I know how they appreciate, I knew it was a decent deal, even though I was paying a lot for it at the time. Um, so you kind of get a feel because of your expertise, because that's what I do all the time. So it definitely does. And I know of things coming on market. I've uh a couple of the properties I've gotten were contacts, you know, through being in the in the industry. So you hear of things that they're not on the market yet and you can buy them. So it definitely helps being an agent to get the inn. Yes, you know.
Reshma VadlamudiYes, and especially like you know the areas in and out, and this creates would make much more sense. And you actually told us, like when we were starting out with with Hamilton, what's happening in Hamilton. Right. And uh that's how that's how we got started. Like when I was looking, like with the lowest possible money that we got, and and you told us this is where you should be looking, and uh we just took that step, and then even though it looked scary, everything in Hamilton looked scary at that time, but then I was just going off by whatever you said. Well, are you glad you listened to me that it worked out? Okay.
Lynn SchwarberSo a lot of people were investing in Hamilton and buying the you know, little Airbnbs, and um and you bought a property that frankly I was kind of scared of. Are you sure you want to buy this? Because it needed you. I was impressed with you buying that property and taking on that project. I remember I think I said to you, are you sure? I mean, because you had to gut that property, redo the whole thing, and you did an amazing job. Yeah, I mean, it is just incredible what you did. And I was I was shocked. Yeah. Um, and then you've done it since to other properties. And you guys have been just incredible what you did.
Reshma VadlamudiBut yeah. The neighborhood, and it was a two-bed, one bed. And you were hearing us telling, like, it'll be a four-bed, three-bed.
Lynn SchwarberLike, how are you gonna make this a four-bed? Okay, but you did. Yeah, you took on more risk than I would have, you know, at the time. So I was impressed with that. But um, and then but when you buy uh a short-term rental now, especially now because so many people have gotten into that game, you gotta really watch what areas because now I think Hamilton's become a bit oversaturated. Yes. Just like Hyde Park, Oakley. Like I look, and there's so many in some of these areas that they're not getting much per night, and there's so much competition. So be careful if you do want to jump into that arena. You really have to do some research on where you do it first.
Reshma VadlamudiThe number of I think it's it all depends on the number of bedrooms and bathrooms and how many of like four beds. I think that particular house is still doing great because it has four beds and like three baths, and people coming to Spookinog, they would want more bathrooms because it's like two families coming together, or a bunch of kids, yes, and also a bunch of coaches coming together. Okay, so that's what they're looking for. That's why it's still doing better. But you also know that there is one more smaller property there. That's the one. It's not it's not as great as the other one, but then that one tends to like with no other houses that we have, we have like 10 to 12 days bookings, never happen usually at other places. Okay, but this one is smaller and it tends to get like longer stays. Longer stays, that's interesting. Yes, yeah, and we don't have uh two properties of that size to compare and do that. But then this is a unique property that we have, like the smaller size, and then it tends to do okay, like even in winters. Well, that's good.
Lynn SchwarberYou probably get you get a lot of those uh like the traveling nurses and people like that that come in that need, you know, or they might they might need a few months. I mean, there are those midterm rentals you can do. Yes. Um, so there's so much opportunity.
Reshma VadlamudiYes, with that, yeah, with that size of a house, especially right, yeah. Yeah, yeah. And also I think with Hamilton right now, what we are seeing is there are more people that are coming in to like for construction or maybe for Miami University, they're coming there to stay more than nurses or medical professionals. It is someone that's coming there to work for a certain amount of period. Oh, so that's what we're seeing. That's why it's like the longer stays there. Yeah, other than spooky men.
Lynn SchwarberYeah, gosh, it's been so amazing to see what the transformation in Hamilton. Yes, especially that main street. Yeah, main street, the restaurants, yeah, yeah, the condo. I mean, all kinds of things that have gone in there. It's really exciting. Yeah, I love it. I mean, and and you got in at a time, and still, I mean, you can still get something reasonable, it's something that needs total renovation.
Reshma VadlamudiI can't believe we bought a property with 70,000 there.
Lynn SchwarberWas it so it was 70, right? Yeah, but look at you now. Yeah, you start with that. Yes, and that's the whole thing. Like you said, you've got you buy one, yes, renovate it, right? Run it out, renovate it. Yes, uh, maybe uh refining. Right. And then you take the equity out and then you buy another one and just keep and that's how you build generational wealth.
Leverage Passive Income And Real Freedom
Reshma VadlamudiYes.
Lynn SchwarberAnd you've discovered that. You've been amazing at doing it. Um, and I just really feel like real estate is the way to build real wealth, you know, for you and your family, uh, more so than just keeping your money in the stock market. Yeah. In fact, I believe that so much. I've taken my money out, the money I had in retirement, I've taken it out through the years and I've put it into real estate because I feel like the returns are better. Yeah. And I want the liquidity. I want, I mean, I sat in my pajamas for the past two days at my laptop in my island, drinking coffee, you know, working, you know, doing emails or whatever, phone calls, and then ding, ding, ding. I have Airbnb, V RBO, you know, deposits going into my account. So that that passive income just coming in. And it's your money is working for you. And so I'm finally at the point in my life, you know, now I'm in my 50s where I can relax a little bit. I don't have to work as hard. I can my my rentals are going to keep bringing in money, even if I'm sitting there in my jammies at my laptop all day. Yes. You know? So it's just that freedom. I mean, that's really true wealth is to have that freedom you know in your life to just let that work for you.
Reshma VadlamudiThe time freedom and the financial freedom to do the things that you really want to do, or exactly. Or you don't really have to do anything. Right. Yes. Right, yeah. And whenever you want to do it.
Lynn SchwarberYeah. Yeah. So I think I wish I discovered that a little earlier. You know, I mean, I started investing, well, I guess it was 15 years ago. But I had my career in journalism and and I made decent money, but it still wasn't, it was still just paying the bills, you know, which most people you get a paycheck, you pay your bills, you know, and then you save a retirement and then you retire and collect money. So I think it's just the mindset. And and I read the book, Rich Dad, Poor Dad, which so many people I think that's a pivotal moment when you read that book. And I was like, wow, it was just mind-blown. You know, I read that. I'm like, yes, why am I? I need to let my money work for me. I mean, why buy if you have $50,000, why buy a car, you know, for $50,000? Buy a buy a junker car just to get you around, you know, and take the money and invest in something that's gonna then make more money for you. Leverage that $50,000. You can own a $200,000 property, you know. Now you own a $200,000 asset and you spent $50,000. And now the people renting it are gonna pay for it for you. You know, and then you're gonna be able to refi or whatever eventually, or sell it and get something bigger. So once you start realizing that, I mean you just mind shift.
Reshma VadlamudiYeah.
Lynn SchwarberAnd your life changes. I mean, I really just am so passionate about that. It really how it can change your life and just yeah, get you off that hamster wheel of work, work, work, you know, living paycheck to paycheck.
Reshma VadlamudiYes. That was one of my questions. Like, do you think someone can save their way to wealth? Save their way? Yeah. People try like cutting back on Starbucks, cutting back on things that they like, but then they think like investing is also dumping money into something that they don't even like try to understand what leverage is, and people are too scared about debt. And they think and then people were I've seen people with two percent interest rate trying to pay it paid as fast as they can. Right. All right. If there is that cash sitting in the bank account, would you go buy a different house or would you try to pay off the two percent interest rate? Okay.
Lynn SchwarberWell, good question, because right now in our country, I think the average equity is something like $300,000. Like people that own a home, the average equity that is is higher than ever before because housing prices have gone up so much. So you're sitting in this house, the value has gone way high. Your interest rate, you probably refinance and you've got a two and a half percent or whatever interest rate. So you're you don't want to move. So your money is just tied up in this house. You're not gonna get that money until you sell it or whatever, retire, whatever, downsize. So, right. So, why if why pay off that two percent mortgage?