Lindsay Preston Friedman began her career in technology when she founded and built WritingRoom dot com in 2006. WritingRoom dot com was an online social network for writers that launched in 2006. It is still operating today and boasts over 50,000 members and hundreds of thousands of pieces of content. WritingRoom.com won NEOSA’s Best of Tech Awards for Best Website 2009.
In her latest technology start-up, she went back to her college roots, where she worked as a State tested Nursing Assistant at Manor Care Nursing Home in Bainbridge, Ohio. Over the years, Lindsay often thought about how technology could be used to improve the quality of care given to seniors. After watching the lack of care towards her grandma at the end of her life, she came up with CareWear Systems. In 2018, she began to build CareWear to empower better personal care through data collection, analyzation, and actionable insights all while decreasing hospital readmissions and infections.
Lindsay is also a published author and award-winning writer.
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“It’s not what we accomplish but it’s who we become along the way and how we develop along the way” – [Mike]
“Being truly an entrepreneur is when you don’t know how to do something, you go figure it out or get someone to do it for you” – [Mike]
“When you’re an entrepreneur, you will fail… but if you can pivot or make the best of it.. you can consider it a success” – [Lindsay Preston]
“It’s only a failure if you don’t learn from it” – [Lindsay Preston]
“We have to surround ourselves with people who are smarter than us cos that’s how we progress and that’s how we get better” – [Mike]
“If you hear the same thing from a lot of really smart people over and over, it’s probably fact” – [Lindsay Preston]
[01:27] Today’s topic “Entrepreneurialism” and guest “Lindsay Preston”
[02:18] Lindsay describes herself and business strategy as “Motivated”
[03:08] Lindsay shares her backstory
[07:25] Where is the Writing Room today?
[10:04] What goes through your mind when you’re out of your space?
[11:45] What inspires you?
[12:53] Lindsay’s approach to failure
[14:54] Comparing entrepreneurship today to ten years ago
[16:24] What advice would you give a new entrepreneur today?
[17:30] Techniques and tips for Raising capital for a business
[22:15] Where do you see yourself in 3-10 years from now?
[23:37] Would you advise a new entrepreneur to do a start-up or buy an existing company?
[30:22] What do you need to learn today to take the next step in your entrepreneurial journey?
[33:33] Most memorable moment in the last 6 months
[34:17] How to contact Lindsay firstname.lastname@example.org
Welcome to this week’s edition of insider secrets. The show that turns multifamily investing into reality. Each show we interview guests who are seasoned professionals, actively closing and managing real estate deals. Your host Mike Moraski has more than 30 years of multifamily, real estate investing, and property management experience.
Mike is the founder of My Core Intentions. And he’s been involved in over $285 million of transactions focuses on helping you create short-term cash flow and long-term wealth. Here’s your host, Mike.
Hey, good afternoon. It’s Mike with, the host of insider secrets brought to you by my core intentions. And let me ask and I ask every week, have you been thinking about your intentions and what you’re planning on doing? let me ask you what matters most to you in your life and in your business.
A lot of times I say it’s not what we accomplished, but it’s who we become along the way. And how we develop and get there. So MCI invests in its client’s future through education, teaching, and coaching. My thing is, I like to help you create short-term cash flow and long-term wealth.
Empowering you to execute sound real estate investing and property management principles while living a well-balanced lifestyle and develop a strong foundation for your life. today we’re going to talk a little bit different. We’re going to talk about entrepreneurial-ism and being an entrepreneur and my guest today, and I’m joined by Lindsey Preston. Lindsay. You want to say hi?
Hello everybody. Thanks for having me, Mike.
Yeah, you bet. I’m glad you’re here, but we’re going to talk about her background and how being an entrepreneur in the multifamily real estate space makes sense because really when you buy multi-family, you’re buying a business and that’s what we’re going to talk about today as being in business.
So I’m excited about today’s guest. She’s been a mentor to me and been very helpful. Lindsey’s an entrepreneur who brings great value to the marketplace and or clients she works with. She’s a published author. Award-winning and has helped me recently carry my book, exit plan across the finish line.
Thanks for that again, by the way. And, Lindsay will tell us in one word, what best describes you and your personal, businesses strategies motivated. So if I asked you then today, what are you motivated for? What would you say?
I would say, I think there’s something to be molded for motivated for every day. I go under the belief that whatever that task you have to do, even if it’s laundry, you do it the best you can, and you go forward with it with a positive attitude and you get it done and your task is complete and you can be proud of what you did, no matter what it is during the day.
That’s awesome. That’s pretty impressive when we can even look at laundry that way. Do you cook? so sometimes if a child who only eats noodles, so we’re basically on a noodle bide at the moment.
So Lindsay, tell us your backstory. How did you come about being an entrepreneur? Do you think that you were born that way or did you develop or.
it’s definitely been a learning curve. So I think it’s been more developed. I started out as a writer and an editor and I was a ghostwriter and so probably 20 years ago now I was doing a lot of ghostwriting and there was no Facebook wasn’t around.
And I felt that writers needed a place that they could go and communicate with each other and connect and find editors find help, find people who you could really work with today. It’s very readily available 20 years ago, not so much. So I came up with my first startup and it was called writing room.com and it was where writers could go post their work.
It free, help communicate with each other, and learn about the publishing industry. And so I wasn’t an entrepreneur until then when I decided I’m going to build this website and I actually went about, I was really young. So I learned how to code, to build the website on my own and then realized once you get it to that point, you still need help and you need to hire people.
And that’s when it started to become a business. And when I saw people starting to come do it and the ability to make monetize that I was like, Oh, I have something here. So my journey became began because I had a need. that’s interesting. what you said is you needed to learn how to code in order to get something done.
So you went and figured that out, and I think that’s really at the heart a lot of times, true on being truly an entrepreneur is when you don’t know how to do something, you go figure it out. Or you get somebody to go do it for you, So you kinda covered that whole base there. So would you say writing room was similar to what blogging was or morphed into blogging or so we were a little earlier than logging.
Cause I remember having a PR person explain to me, maybe you want it to just be an article site and a blog and blog was a new word at the time. And. It has morphed into that, but what I really wanted it to be was for more writers who were writing long, longer material. Okay. so where did you take that business?
Did you, when you started that business, did you know that you were going to make it a full blown business or was it started as a hobby? It started as a hobby. Then I saw it was before my space even sold. Since you remember there that big sales, like the first big sale and it started as a hobby and then my space sold and I was like, I could have something.
Wow. Interesting. Yeah. I never got to be like anything like my space, obviously much more niche, but it, the most interesting thing to me was that the community took over what, from what I thought it was going to be. Which was an interesting thing. Cause I was like, I wanted people to post their books.
Innopsis is and ask for editors and work together. And it turned into much more of a sharing site asking for comments, which I think is what a lot of social media is. It turned into what social media is when I was in, that was not my exact plan. Yeah. It’s I think you have to, as an entrepreneur, or be able to transition to what your users tell you they want to do.
And I think Mark Zuckerberg said that, Facebook wasn’t his initial plan either. Didn’t it start out as a little platform for college kids to talk to each other at Harvard. Yes. And then he started expanding slowly your user base, or your customer will tell you what they want or they don’t want.
So it’s interesting where things can go or where you can take things and not even really understand yet to where they could go. So it sounds like you were, it might’ve even been at that level where you didn’t really even understand where it possibly could go. So where’s writing room today.
Writing room is still up and running. It has millions of pieces of content. a lot of users, I let it live now and it’s become its own community. And the members run everything, which is great for them. I use it as a marketing tool or authors that I work with. So it has in the end, it never sold.
It was never in my space, but for what I was doing, it has been a successful endeavor for me. Good for you. So where did you go after a writing room or where did you transition? I should say so I was doing these interviews on writing room. I would go to writing conferences and interviews authors and put them up on writing our site.
And I remember one day an author said to me, you’d be really great. If you could put my book behind me. Now, this probably goes back to 2005 or six. Whereas like everyone knows now with zoom, you can change the background and it doesn’t work real well yet, but I came up with it. I actually came up with that technology in 2005 to change the background without a green screen.
So that company was called flip and filed a bunch of patents on it. And that was one that I was out of my space. It was a very good learning experience. I did not know video, whereas writing, remind new writing, and I knew the technology end, but I was not an expert in video processing. So had to bring someone in and.
Worked a really long time on it ended up having the patents on background, video removal without doing anything, just using your camera. So in February of this year actually sold all the patents and it was a great learning experience because when you are an entrepreneur, you will fail right. You will not come.
It will not come out to be the way you want it to be. But if you can pivot or make the best of it or find a way to, monetize in a way you weren’t expecting, you can consider it a success. So you said a couple of things that are really interesting. We could probably do a fleet podcasts on both of these topics, but you said out of your space and boy, that really resonates with me because as an entrepreneur, don’t, we so often get into these places that we operate outside of our box and not really sure what we’re doing or how we got there.
What do you think gets you through that? So when you’re in that place, what are you feeling what’s going on for you? What w what do you want to accomplish? What goes through your mind? especially with flip, it was really about learning everything I could. And I, at some point realized I was never going to be an expert in AI and machine learning and video processing.
So knowing that you need to bring in somebody who’s better than you at that. And I had an incredible partner who is probably one of the best in the industry doing that. And he took over the CTO role, but I was still running the company, which I wasn’t equipped to do. I hadn’t run anything like a YouTube or something you’d seen out there before.
And. I think when you can acquiesce to what you’re good at and what you’re not good at and realize that if you have to bring somebody in who’s better than you take their advice. So you’d say get a coach, right? How coach there. That was a good segue. Yes, no, you definitely need somebody who knows what they’re doing and to be open to that, a coach or a mentor.
Sure. Yeah. so what inspires you. everything. I know that’s a big one. You can find inspiration anywhere, during a day’s time, but when it comes to, being an entrepreneur, the things that inspire me are more, the things that I found a need at a given camp. And I think if you move forward thinking I want to do something incredible.
What is needed. You don’t think of a feature. Don’t think of, something that would be cool. Think of something that’s going to really meet somebody needs. And typically if you start with your own needs, then you’re not going to be the only person who needs something that isn’t there. And I remember, I remember being a kid and my dad telling me, Hey, if you’re going to go into business for yourself, go into food, shelter, clothing, the three basic needs, in a human being. And if you go into any one of those, you’re probably going to have success. I’ve been in real estate and it’s never failed me. So it’s interesting. Speaking of failure, which you mentioned, how do you, what happens to you when you fail? What, how do you respond to it? How do you deal with it?
you pick yourself back up, you learned from it. I think that is the biggest thing. When something doesn’t go right, look at why it didn’t go. And really take a hard look at what you can do differently. Not about the situation around you or someone else who didn’t work out in your favor. what can you do differently the next time?
Because it’s only a failure if you don’t learn from, so you sold flip successfully or Fe, or was it, in your own mind? Because everybody has their own judgment, right? So you have a judgment and people around you have a judgment were in your own mind. Was it a successful sale or not? So I had some high hopes for that piece of technology.
It’s not even the companies much, but having the patents on this particular piece of technology and during COVID, it popped up on zoom on Tik TOK on Instagram. So I think that was a disappointment, but that was really, That was a disappointment because I wasn’t capable of doing it. And it’s really opening your eyes and saying that was out of my realm of connections of where I live.
It was not conducive to, finding more investment. And so I had bigger hopes for it, but it’s not a complete failure. So in your own mind, you’re a success. And I don’t know that anything else matters at that point, does it? No. Like I can look at the end of the day, I don’t lose sleep over it. so being an entrepreneur today versus 10 years ago is different.
10 years ago, you didn’t have social media and you couldn’t be as loud as you can be today and post content and for free. And so from an entrepreneurial standpoint, what do you, what’s different for you today in how you run a business or how you operate? There’s so much that’s different and I think it’s good and bad.
10 years ago, if you had a solid plan, good idea, and proof and a team that could execute, you could go out and raise money relatively easily. You’re not letting, not just like sticking your hands out, but it wasn’t quite the challenge of that. At least I am finding it to be today. Now, the marketing’s really different too.
There are a lot of. Easier less expensive ways to market yourself to a much more crowded group of people who are now very, used to just growling over ads. So it’s good and bad, and I’ve seen some benefits and some things that very have not been as great for people, at least in the industries that I’ve been working in.
So what advice today would you give a new entrepreneur who said, Hey, I’m going to open a business and it doesn’t matter what business, but what advice would you give a new entrepreneur to make sure you have a solid plan, know why you’re doing it, know who your customer is and what they want to make sure you really truly understand the market because just because you think they want it doesn’t mean they do.
And then be ready to pivot at that point in time. It’s really an important piece. Isn’t it? you’ve mentioned that a couple of times is being able to recover or move in a different way. Yes, it really is important. And also listening to people and knowing that if someone is telling you not to just do it, because you’ve been told to do it to really back that up.
So also take the information you’re being given and validated. Very good. So have you ever had to raise capital or attract investors at being an entrepreneur for your business? and any techniques around that, how have you gone about doing that? So that is my beast. Favorite part of being an entrepreneur like absolutely.
I would rather fail and go raise money. which I guess you do sometimes feel if you don’t raise the money, have your ducks in a row, have all the paperwork you need. be humble when you go to them. be open, make sure your valuation makes sense, and make sure you’re targeting investors who are in your space.
when you talk about valuation, you see some of these valuations today and you go, are you kidding me? it was something that comes to mind is a valuation on a technology company that is an unproven asset and they can raise billions of dollars. And it’s like, how do you do that?
And I have a proven model and how do I go raise money? so I like what you said about being humble and have a plan and stick here, plan. How do you brand yourself around that though, so that you look the part or can produce what your investors might want to see? I think to look the part, it really takes the time.
You need to understand your business, understand your market, understand how you’re going to make money. Understand what it costs to run that business. And if you’re really knowledgeable and can you have all the answers or if you actually don’t have the answer, and you’re honest enough to say, we need to be further down the line, or we’re really trying to evaluate that.
Or we brought in an expert to look at that and being honest with where you’re are, where you are. I’m trying to at least understand everything is probably the best way to position yourself for an investment. I know a lot of startups like to go in and I’ve done it with both my startups where you raise money pre-revenue and it’s a much harder raise and you’re going to give up a lot more equity.
So again, it goes back to when you go in and you’d be humble and it’s in realize that the investor is taking a huge risk. It’s interesting. So you’ve done two startups. Do you think that you’ll do another startup or do you think that maybe you might go buy another business and what’s easier? So I’m actually, I have started my third startup and I’m working on it now.
It’s in a completely different space. I came up with the technology it’s for, here compliance. In elderly patients, home healthcare and nursing homes. And I came up with after having the lack of care for my grandmother. So it was a need, it’s an, it’s a large market. It’s a need that we knew that most people know are there.
But I, so I came up with this, but with this startup, I was knowledgeable enough at this point to know that I’m not the run it because I am not in healthcare. So somebody else is actually CEO and running the company right now. So how do we go from technology to healthcare? that’s a pretty big flip, right?
it is a technology play in the healthcare space. So it has to do with sensors and, software tracking, behaviors of caregivers and patients. So it is, it’s a stretch and the fact that it’s a different market, but it is still a technology play. Okay. So interesting. and here’s what I, What you said is this time you realized, Hey, I’m not smart enough to run this.
I need to get somebody who’s smarter than me. And. And one of the things I teach a lot is we have to surround ourselves with people who are smarter than us, because that’s how we progress. And that’s how we get better. If we don’t know something, go find somebody who does know it and let them operate it.
And I have found over the years that when I do that, one of, one of the big things I always did when I hired people was hired up, hired smarter than me, because I knew that. They would help over the long haul and it’s played out that way. so where do you see yourself? as an entrepreneur, three years, five years, even 10 years from now.
So I, the plan with this health tech startup is for an exit, a five-year exit. I would tell you today, I probably won’t do another startup, but I said that after the second one, I think by these, have you get to that finish line, unless you have some massive success when you get there, whatever that finish line is when you finish, when you truly finished.
And it’s not just a complete shutdown, if it isn’t like a race where you’re like the front of the pack, you’re a little tired. Yeah at the end. So I was definitely a little tired, but had this idea and, and it was very much enjoying it. And I feel like this is probably this company has a much bigger fit in the market.
So we’ll see. This might be like my, it might be like my Olympic race where I like get a metal and I’ll do something at the end again. what’s interesting is they call people like you and I serial entrepreneurs. Cause when you think you’re done, you’re not done. Something comes up. So I want to ask this question is so a new entrepreneur today that you might be talking to, or, they might be picking your brain.
Would you advise them to do a startup or buy an existing company? So I think the biggest difference between startups and a traditional business is I look at start as if something with an innovative business model. It’s not a flower shopper pizza shop where your model is very simple. You’re going to make pizzas and you’re gonna sell them.
And that’s what you do. Whereas. More of these technology startups. They, there’s something very innovative either about the way they’re doing business or what they’re selling. So if you are not looking for doing something brand new, that’s different that people haven’t seen before. Then I would say, get a business, something that has a customer base.
If you’re doing something really innovative, then you’re going to have a startup. I think that’s the real difference. I will tell you what the startup you better be ready to commit every second of the day. a true entrepreneur, right? And we hear this a lot in the marketplace by some people is that they roll their sleeves up.
And while everybody else is at a frat party or out with their friends or on Friday night, they’re out to dinner or watching the football game on Sunday. A true entrepreneur is working and has their sleeves rolled up and they’re putting in the time and the grind and the effort, To get to a point where then they can do all those other things.
But I think that as an entrepreneur, there’s that play before or pay before you play. and the other mentality in life is play before you pay, do you have any thoughts around that or what it takes really to. Be successful. It takes a lot of commitment, and it takes the ability to, if you fail, if you’re failing or if you’re getting criticism to analyze why and to switch what you’re doing with an and move forward from that.
So do you buy into the criticism? So this’ll be an interesting one because as I’m a writer and writers get a lot of, constructive critics. So I know. and I give a lot of constructive criticism, but as a, this is a great example. As I told you, when you were doing your book, there’s some things I can tell you that are just right or wrong Ram or syntax, that’s a right or wrong kind of thing.
The content is not right or wrong, but if you hear the same criticism over and over, it’s no longer just someone’s opinion. It’s probably not. So you have to weigh someone’s opinion with fact. How do you, how do you determine fact? I look at it as if you hear the same thing from a lot of really smart people over and over. It’s probably fact, but what we discussed when we were going through your book something’s style, bullet points versus number, Doing antidotes throughout your book.
Some things are really just a style and how you want to present yourself and really understanding what’s truly wrong. But if you get a lot of people telling you this isn’t right, this isn’t right, this isn’t right. This isn’t working. There’s a chance that they’re right. Do you think that the general public buys business buys from a particular business? No, regardless of the industry, because of style or because of the owner’s style or personality, I take that as branding. Okay. And a great way to look at the branding is what’s a hand sanitizer name, a hand sanitizer cheese. How many you’re out? But if you go in and you buy, there’s no pure out, you’re not going to buy, not buy the one that’s right next to it.
However, if you see Purell and you see the other one probably going to grab the pure out. Sure. So I think it’s that branding makes a difference and it doesn’t mean that one is right and one is wrong. Cause both of those things are getting Trumpians clean, but that’s, we’re really focusing on your brand.
Is why you choose one thing over another. So let’s talk about branding a little bit more for a minute. So take a company like Gillette. Okay. Razor’s been around for a hundred years, right? a company comes along like Harry’s and I’m not trying to brand anybody here, but. But all of a sudden starts to take a big chunk out of the marketplace.
When you’ve got a company that’s branded themselves for years and years, people know Gillette, and July comes out with new products and they put new things on the marketplace. What makes another company come into the marketplace like that and disrupt the industry? I think it has to be something different.
You have to be putting out something. That’s a little different, a little more of a lifestyle. I actually can’t think what it’s called, but I know that there is a shaving company that is pretty large now, and it was a disruptor of the industry. They actually have like them at the mall and it was more of a fancy man’s beard trimming them and they just, and they would be a disruptor for July.
I think if you’re going to come in and try to disrupt the industry, it either has to be something for a different lifestyle, a different demographic, finding that niche that people are going to cling onto. and I think that’s a harder play. I think if you’re saying like, I’m just going to be, I’m going to disrupt this industry because I’m going to be my branding’s different.
You better have a lot of money to back up that marketing? Yeah. Yeah, for sure. listen, we’re getting to the end. any thoughts that you would, two questions. So what do you need to learn today, to take the next step in your entrepreneurial journey? I need to learn so much. There’s probably a lot I could learn.
not just today, over forever. I don’t think you ever stop learning. Yeah. So what do you do to learn, read a lot. Talk to people, go to different net. not now, but prior go to different networking events, ask a lot of questions. and it’s interesting how that whole part of the world has shifted too.
People are saying, maybe we’re, school’s not all it’s made up to be, and there’s other ways to learn and there’s other platforms and that’s become an interesting trend in the marketplace also. So I think that’s something to watch for right now. Absolutely. There’s a lot of ways to disrupt the worlds right now for people staying at home.
so give one idea that you might be thinking about. Actually, if I had a really good idea, I’d probably do another startup. I don’t know. Cause I’m someone who I think it’s the bad idea is going to have to come from someone who. Is missing something from being common. I’m sure there are a lot of people.
I enjoy the being at home. And which goes back to what you said about the technology piece, the healthcare technology piece, because you had challenges with your grandmother and this. Came out of a result of that. And I think that a lot of times people miss opportunities because they just blow it off.
So I think you have to be more self-aware too, it’s chic to be an entrepreneur today where 10 years ago, 15 years ago. It was, if you were an entrepreneur, people just thought you were a glorified salesperson. and today it’s like it’s chic, but a lot of people, I think shouldn’t be entrepreneurs because they’re, I’ve heard it said they live off mommy and daddy, you have to be prepared to, you’re not getting a weekly paycheck.
It’s about, you have to have a lot of passion. Yeah. So on a lighter note, where are you calling from today? By the way, I am in Cleveland, Ohio. in Cleveland, Ohio, what is your favorite restaurant? this is what, I’m not a restaurant person. I’m like my nine-year-old. We can eat noodles or peanut butter and jelly sandwich.
Every single day. Oh yeah, that’d be perfect. So favorite restaurants, noodles at Lindsey’s house is that Lindsay actually mine’s peanut butter and jellies. Lily’s is noodles good for her? how about a favorite tourist attraction? No tourist attraction in Cleveland. I would say the rock hall. Oh. And if you’re going to come to Cleveland, probably.
And you like that. Say it again and you like music, I would say. Yeah. Cool. And then, most memorable moment in the last six months. So we were fortunate enough literally like days before COVID hit and stuff started closing down. I got to see the brothers, the Allman brother’s 50th-anniversary tour in New York City.
Wow. Nice. There are some clips of that on YouTube. I was just the other night. Fantastic. Cool. Yeah. Yeah. I bet. I bet it was the last concert of since COVID. Yeah, so you’re an old rock and roller is what it sounds like old soul. That’s good. So listen, if people want to get ahold of you or pick your brain a little bit more, how did they do that?
You can reach me at email@example.com and I’m pretty good about getting back to emails. Great. listen, thanks for today. Thanks for the time. And the insight. The knowledge is always great for people to dive into and get some results from. And, we’ll be here next Tuesday again on insider secrets.
I want to thank everybody for listening in our listeners today. And Lindsay really thank you for being here and for all your input. Thank you.
Thank you, Mike, and thank you for joining us for another great episode of insider secrets as always Insider Secrets is brought to you by my corn tensions. Join us on social media and visit my core intentions.com where you can get expert coaching on all things, multifamily investing in property management.
We’re looking forward to having you back again next week for more insider secrets.