Lauren Ramsey, Betsy Bash

[00:00:55] Sanjay Parekh: With a creative writing and data analysis background, Lauren Ramsey brings all of her skills to the table as the founder and Chief Engagement Officer of Betsy Bash. Founded in 2010, Lauren and her team help local businesses get more leads and make more sales using social media. She’s taken her business from her hometown of Houston to her new home in Chicago. Here today to talk about her business journey over the last 12 years is Lauren Ramsey. Lauren, welcome to the show!

[00:01:23] Lauren Ramsey: Thanks so much for having me.

[00:01:25] Sanjay Parekh: So, I'm excited to have you on because I've lived in the world of social media for quite some time. I think we could probably do a very long podcast, just about all the good and bad of social media. But we're going to talk about other stuff first. First could you give us like a quick background, just a minute or two about your background and how you got to where you are now.

[00:01:46] Lauren Ramsey: Yeah, so my mom, when I was growing up, my mom had her own business as well, and I started helping her when I was like 11, 12, 14. And learned a lot about small business from her but also really learned a lot about marketing and helping her market her business, and I loved it. And then, fast forward to college. I really wanted to do programming, so I learned C++, HTML, Java, all that, and graduated with an MIS degree. But on that process, I had to take a marketing class for my business degree and fell in love. I was like, oh my goodness, this is it. I should change my career. I’d have to change my degree, like everything needs to change. But I was right around the corner from graduating. There was no way all that was going to happen. So, I'm like, all right, I'll graduate. I'll figure it out.

And then, I was in a philosophy honor society. I was the president and one of our members asked us if we wanted to help volunteer. And so, I was like, okay, yeah, sure. And she worked for Radio Disney. She was the promotions manager. So out of college I started volunteering with her, working part-time till I found a full-time job. I found a full-time job, still kept working for Radio Disney. Because I was like, this is just so fun. So, then I learned a lot about branding and marketing and client relationships from Disney, so I did that for about five years until I was like, okay, I need a side hustle. I'm going to start doing marketing on the side and just figure it out. And right about then is when social media started to really develop into a business tool. So, Instagram was just about to be born. Facebook was getting a little bit more robust. It was 2010. So that's kind of how I started got started in my marketing business.

[00:03:32] Sanjay Parekh: Yeah. So, I've got to ask you a question about your mom, since you said you worked in her business. What kind of business was it that you worked in?

[00:03:38] Lauren Ramsey: Yeah. So, I grew up overseas and when we moved back to the states, my parents got divorced and my mom, she comes from a long line of quilters and when we lived in India, she was teaching quilting classes and sewing classes. And so, she had a huge network of people in the textile industry in India. We lived there for three years. So, lots of people that she'd met over the course of time we were living there. So, she put all these skills together and she was like I'm going to design quilts stateside. I'm going to have them pieced and sewn together in India. And then sell them wholesale back to little cute quilt and cottage shops, all around the United States. So that's what she did. She designed quilts and sold them wholesale.

[00:04:25] Sanjay Parekh: Okay. That's awesome.

[00:04:28] Lauren Ramsey: We would go to markets, so we would have to market her booth and we started off with like temporary booths and then graduated to a bigger temporary booth and then graduated to like a full showroom, and she would win like awards for design, and it was so fun.

[00:04:42] Sanjay Parekh: That's a huge logistics challenge too, right? Starting like, hey, we're going to have the people there and moving all the stuff back and forth. And I think in the last couple years with the pandemic, obviously this was a long time ago, but with the pandemic, it's become more clear to everybody. Like, logistics is a huge deal. And probably just the challenges she had with that were probably immense.

[00:05:05] Lauren Ramsey: Oh yeah. I'm sure she could tell you stories for days on containers.

[00:05:11] Sanjay Parekh: Good on her. Glad I've never had to deal with containers. That's a great thing. So, what drove you to decide to do a side hustle? Was it that you wanted to continue learning or was there something that you were like, hey, I need to make some more money? Or what was it that made you decide to do a side hustle on top of your full-time job?

[00:05:29] Lauren Ramsey: It was really that drive of, I can't stop thinking about it. What if this was a thing, what would that look like? And I loved my job, and I had a great career, so I'm always like, ooh, it's like, would you jump out of a perfectly good airplane? I'm like, I had a fine career. I could have stayed there, but I just kept having this calling of, Lauren, help small businesses, Lauren, help small business to understand social media. Because a lot of business owners around 2010 were in like the boomer generation, right? So, they didn't grow up with social media the way that we did. And there just wasn't as many business owners in our generation yet. I think Gen Z has really taken that forward and been like, oh, millennials, like you guys started a bunch of businesses, we're going to do that even younger. They're in high school and college. I'm like, dang. Alright, go you. So, that was a generational gap of I know I need to be on social, but what do I need to do? What is good? And so that's really where I wanted to help.

[00:06:38] Sanjay Parekh: Yeah. Yeah. It was that same gap that happened when the web started, right? It took a long time for these companies to even have a webpage.

[00:06:47] Lauren Ramsey: Yeah, like I remember we were at a market in Atlanta, and we were walking down the hall with my mom and one of her business partners, not business partner, but they worked a lot together. And she was like, so what do I need to do? I need to get a website? My mom was like, yes, they're very important. You need to have one. She's like, I don't know. So, it's just so crazy to think of there was a time when people were like, maybe I'll get a website. And now of course you can't get away without that.

[00:07:16] Sanjay Parekh: Yeah. The alternate was like I'm in the yellow pages. Like, why do I need a website? Like people can find me in the phone book. What is this web thing for? I want customers to come to me in person, not on some computer. Like I don't do computer things. And it is so funny those shifts that happen over time. And so, it sounds like you're in that or have been working in that shift of like, why is social media important? Obviously, I think we get it now, but when you started, it wasn't maybe as clear to a lot of these folks. So, what then took you down that path? So, you started the side hustle thing, to help. At what point was it that you were like, okay, I've got to do this full-time. I need to quit my job and go all in.

[00:08:07] Lauren Ramsey: Sure. So, first I just wanted to prove the concept. Like I wasn't doing everything, right? I wasn't a PR agency. I wasn't like a big creative service agency. I delivered social strategy, postings, all that stuff, but it was only social media. So, I wasn't even sure if it would work. So, a few years of just making sure people would just pay for this. And if this was the only marketing they were doing, would it work? Or does there need to be a bigger marketing mix? So, I did that for a little while. Proved that it would work. And then in my career they were asking me to take on more. They wanted me to manage people. And I was like, okay, I'm really at a place where I have to decide, because I was working full-time, I was coming home, working at night, I was working on the weekends, and I was just exhausted. And I knew that I had this great career, and it would serve me well going forward. But I also knew I had this passion that was doing well, like doing good, good enough to give it a chance, but could it replace my career? Could it be my full-time job? And that was the big question, that was the big leap of faith of ooh, quitting my job. It's crazy. But it worked out.

[00:09:27] Sanjay Parekh: Yeah. Yeah. So, how long was it from when you did the side hustle, when you started the side hustle, to when you quit and went all in?

[00:09:34] Lauren Ramsey: Five years.

[00:09:36] Sanjay Parekh: Five years, okay. And so, during those five years, you alluded to this I want to make sure I get the fine point on it. You said you wanted to make sure that it worked. So, how is it that you figured that out? Was it that you were taking data or like seeing what your client's sales were before and after? Like, how did you figure out that yes, definitely what I'm doing is working?

[00:09:55] Lauren Ramsey: Yeah. There wasn't as many tools back then. But for us it was more of, are we delivering value? Is there more of a benefit in these touchy-feely posts? Is there more of a benefit of just straight ads? Is there more of a benefit of just selling what they're trying to get people to buy? And of course, it's a mix of all three, right? And so, first it was, will they pay what I want them to pay? Can I deliver the value that they're paying for? And then is it scalable?

[00:10:31] Sanjay Parekh: Right, right. Yeah. Okay. So, you also alluded to this and I want to dig into it a little bit, is, we often don't talk about the things that scare us as founders, or at least in media, it doesn't get discussed, because we just want to talk about the glitz and glamour, but I think all of us have fear. Fear when we start and then fear ongoing. So, what scared you about doing this, either starting as a side hustle or when you went all in, or both? And what scares you now and how do you manage that?

[00:11:03] Lauren Ramsey: That's a great question. I think when it was a side hustle, nothing really felt scary, other than maybe just not being able to have enough time to do everything.

[00:11:13] Sanjay Parekh: And is that because you felt like there was no downside or because it was a side hustle? Like why did it feel like nothing was scary?

[00:11:22] Lauren Ramsey: Because I think it was exciting. I was a part of the first people that were like helping people market on social media. And in Houston we had a huge creative community that was on Twitter. And so, I've made a lot of friends on Twitter that are still like really close friends of mine now, but all of us are like, how do you do this part? What should we do here? Or, like I remember even there was a question of, is it okay to look up people's social media profiles before an interview? We were just, we were all figuring it out. And so, it was more exciting, right? It was more of you're on the cusp of something new and just exciting.

And then, fast forward to quitting my job. That definitely felt scary. There is that feeling of financial security with a job, even if it's not entirely true. The company could go through layoffs, like something could happen, right? But it feels more secure than having your own company. So, there was that part of it. And then there was also, what if I fail, what if I can't do this? And of course, I made it more complicated by moving from Houston to Chicago. So, I started over, basically. I had no network, it was kind of crazy, but I figured if I didn't do it then I would get really comfortable in Houston, and I wouldn't move to Chicago. And it was really a dream of mine to move here.

[00:12:56] Sanjay Parekh: Yeah, it's funny because as entrepreneurs, I've heard this story multiple times and I've lived through this story too. I feel like we make it harder on ourselves. Like we do things that, then in retrospect, it's like, huh, that probably wasn't the smartest thing. I just made it worse to be successful because I piled all of these things on. So how did you deal with that fear, that scariness of going all in? And how do you manage it even today?

[00:13:27] Lauren Ramsey: Yeah, I mean for me at that time it was a lot of support. So, I had family in Chicago that really supported me through my first year of moving to Chicago. And then I made a couple friends, and they helped me just get to learn the city. I didn't realize how hard it is to move to a new city as an adult. You can't just make friends as easily as you could when you were in college or high school or whatever. It's so weird, right? It's like the fears I have now are that like, I don't know something, like something's just going to completely blindside me or, all of my team is going to quit. I have a lot of irrational fears, but then I try to play it forward. Like if somebody left, who could backfill or, I try to mitigate my fears so that my anxiety goes. But I don't know that my fears ever go away.

[00:14:25] Sanjay Parekh: Yeah. Yeah. And I think for a lot of entrepreneurs, fear is one of the things that probably drives you as well, right? This is totally unrelated to the startup and entrepreneurial thing, but I've got to ask you because you just alluded to it. So, one of the hardest things as an adult is to make new friends. How did you do that?

[00:14:45] Lauren Ramsey: Oh my God, it was awful. I just don't wish it on anyone. But we all do it, right? Or no, we don't. We don't all do it, but there's lots of us that do. So, one of the things that worked for me really well in Houston was I had a really big creative community. And there was like one main group that I was a part of that was like creative women. And so many of my good friends came from that group. I learned a lot about business from those ladies because they all had their own little side hustles or businesses. And so, I was like, all right, creative women, let's just start there.

So, I went on Meetup and found some creative women groups and started showing up. And then I slowly made friends that way. And so, there was a girl, Andrea Klunder, and she was the founder of a creative women's group. And she became one of my, she was my first friend in Chicago. And then from there, gosh, I don't know. I joined an improv class so I could learn improv and made really good friends there. In fact, we took improv classes right before the pandemic, winter of 2019. And so, we were in like class one, class two, we were starting class three, by the time like pandemic came around and we all thought, oh, two weeks, couple months. So, we stayed in touch thinking like in a couple months we'll be back out into the real world. So, fast forward three years later, we're still all like meeting up and like having virtual happy hours, like half the group’s moved across the world or across the country. But we still stay connected, which I think is really special.

[00:16:24] Adam Walker: Support for this podcast comes from Hiscox, committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available. At Hiscox.com. Hiscox, the business insurance experts.

[00:16:45] Sanjay Parekh: Okay. Let's get back to the talk of business. So, I think you've actually just touched on some of these things, but how do you manage the stress of owning a business and everything else about life and things like that? Like how are you balancing those things in your life for yourself?

[00:17:07] Lauren Ramsey: Yeah, I think, not to be cliche, but you have to take care of yourself first. And I didn't do that at first. At first, I was like, it's all about the business. I'm last. Who cares if I go to the doctor? I just need this business to work. And then I started having just issues where I'm like, I need to go to a therapist, I need to have a business coach. And so, I started setting myself up with these tools that are really just like helpful for anyone, but I think particularly for entrepreneurs, because we have so much stress on a day-to-day basis. The support of therapy is really important for me and the support of my business coach and the support of mentors. And just surrounding yourself with people who have been through it, and can tell you that your anxiety is a little off chart, a little off the path or is right on track, like you should fix this. Like you need to put that process in place.

[00:18:07] SanjayParekh: Yeah. How do you think about your boundaries between all of these things as well? Like personal and business. Are you strict because as entrepreneurs we could really work 24/7. And so how do you think about that and how do you deal with those things?

[00:18:27] Lauren Ramsey: Yeah. When first starting out, similarly, I was just like, whatever it needs, I'm there. 8:00 PM — whatever, 2:00 AM — I got you. But then I also started to realize that wasn't healthy. Like I needed that time. I needed the day to end and for my relaxation time to start. And so, I don't really know when it was, maybe two or three years ago, or maybe even pre-pandemic. I started getting really strict about my work hours, and I was like, I'm going to work nine to six, maybe seven. But after that, its Lauren time. I'm going to go to yoga class, I'm going to cook dinner, I'm going to meet my friends for dinner. And of course, I'm addicted to emails. I'm always checking. But now I just read it and I don't action on it. So, I'm like, okay, tomorrow I've got something to deal with. Or if it's an emergency, I'll deal with it. But if it's not an emergency, then I know it can wait till tomorrow.

[00:19:27] Sanjay Parekh: Yeah. Those very often social media emergencies, right?

[00:19:31] Lauren Ramsey: Some of them you can't ignore for sure.

[00:19:36] Sanjay Parekh: So, let's talk about you. You talked about some of the things that you've put in place. Business coaches, things like that. But are there any other like technologies or apps or systems that you've put in place over the years that help you manage the business and make it so that it doesn't cause as much stress as it did before?

[00:19:56] Lauren Ramsey: Totally. I'm one of those people that's mostly organized and some part like crazy. Like I'll have like things piled on my floor, but all my projects are in order. So, I had that kind of going for me, but I knew that the systems I had in my business could be better. And so, I have a friend down in Houston. He's like an operations coach and he worked with me for 12 months and really dug into my systems, learned them in and out so that he could advise on what the best process was. So that, operationally, things run smoothly. And so, the tools that we have in place are the Google Suite, so we keep everything in Google Docs and Google Drive, then Asana for all of our project management tracking. Slack for all of our team communication. So, that means like my team and I do not email each other. We do not text each other, unless it's not work related. And it's Hey, I saw this, so I thought that would be fun for you. And also, that means if I'm texting you, it's probably an emergency, so it allows that channel to be very siloed. We use Whereby for all of our meetings We use Canva for all of our designs. We use Sprout Social for all of our scheduling and posting as well as our community management.

[00:21:22] Sanjay Parekh: Yeah. So, this suite of stuff then is basically everything that allows you to do all the things that you need to get done on a day-to-day basis.

[00:21:31] Lauren Ramsey: Yeah. Yeah. And then some of the feedback that I've gotten from team members is that a lot of businesses don't have it so siloed. Or they're like, sometimes you email me, sometimes it's in Asana, sometimes it's on Slack, whereas only the project details are in Asana. Any communication around the task is in Slack. And that way you don't have to search a million places to find it. So, all the things I set up were so that we could work faster and not be confused. Because, also from the very beginning, I wanted this business to be remote. And so, all of my team members are remote. We work all over the US, and I went to Texas for a month because it's winter in Chicago, so why not? But it's the beautiful thing about being able to work from anywhere. But I think being organized really helps facilitate less frustration. When you don't have that face-to-face interaction, you need your tools to work really well.

[00:22:28] SanjayParekh: Yeah, I could imagine that being really hard if you have to go hunt for a piece of information and all this stuff. I don't know how companies actually do that. We're very much the same way. We've got, Slack is probably our main thing, and if I get emails from teammates, it's because there's a big attachment or something like that I need to look at, that Slack's not going to handle. That might be the only reason. Okay. So, you've been doing this for a while now. And I'd love for you to take a kind of a look back and think about, if you could go back in time, is there something that you would do differently? And what is it and why would you do it differently and how would you do it differently?

[00:23:06] Lauren Ramsey: I would get like a giant loan, and I would've started this business in 2011. Full on. I always think like I had the right idea. I just didn't realize that it was, like, such a big idea. Yeah. I just thought oh yeah, probably somebody else is thinking of this too, but I think the interesting thing about our business is that we only focus on social, right? And social changes so frequently, that having a team that only focuses on social can really make you feel confident that they've got your social. So, we end up being a lot of white labeled. We're a white labeled company for a lot of agencies, because they've got all the other stuff, but they don't want to keep up with everything that's happening in social. So, they bring us in when they need a, have a client that really needs that social expertise.

[00:24:05] Sanjay Parekh: Yeah. Was money, the only thing that kept you from doing this earlier? Was that the stumbling block?

[00:24:12] Lauren Ramsey: No, I would say the money, but also the courage and then the belief. I was always like, maybe this will be, I have an idea. I was, like, very timid about it, but I was like, I did have a good idea. Like I should have just gone for it.

[00:24:31] Sanjay Parekh: Yeah. Yeah. And it's funny because it's easy to realize that in retrospect, right?

[00:24:36] Lauren Ramsey: Hundred percent.

[00:24:37] Sanjay Parekh: It's really hard and really easy to question yourself and like that thing that you just said, right? Somebody else has got to be doing this one. Not necessarily. Somebody else might be thinking it, but they might be going through the same exact thing as you of oh, somebody else is going to do this, so I'm just going to sit and wait for them to do it. So, what would you tell somebody who's thinking about, like you, thinking about starting that side hustle? Or, like you, trying to take that side hustle into a small business. What would you tell them?

[00:25:11] Lauren Ramsey: Oh, I don't know. That's so big. Such a big question, I mean. I would definitely say work with a mentor who's done it before. And let them provide you with a little bit of a guide map. I was just talking with a friend about a company here in Chicago that launched really smartly, and they were like a food company. And they partnered with a coffee shop and just sold food at the heaviest commuting times, and then proved that people wanted their food. And then like all the next steps, they laddered up until they had a brick and mortar. They didn't start with the brick and mortar. And I think a lot of people do it backwards where they're like, I'm just going to do it all. And then they realize, oh gosh, this is expensive. Or I don't have enough customers, or things like that. I would definitely say get a roadmap from somebody who's done it before to help yourself out.

[00:26:17] Sanjay Parekh: Yeah. Yeah. That's great advice. I like that. And I think we're seeing that with a lot of people that start out with things like food trucks and then eventually move into brick and mortar. That's that nice stepwise approach.

[00:26:29] Lauren Ramsey: And I think people love that, as customers, they're a part of that journey. It's like, I remember when you were a food truck, I was like, you're one of those old OG customers.

[00:26:40] Sanjay Parekh: Right, right. Yeah, I like that. Yeah. Okay, so now one last question for you really honed in on your expertise. For our listeners, what's the one kind of secret thing or thing they should know about doing marketing on social that they should absolutely do or not do right now?

[00:27:02] Lauren Ramsey: Oh, that's a good one.

[00:27:04] Sanjay Parekh: What are you seeing people mess up, or do phenomenally well?

[00:27:10] Lauren Ramsey: I would say there's a couple things.

Try before you feel ready when it comes to social. If you feel like, I'm nervous being on camera, I don't want to do a video, use a silly filter, put makeup on yourself, turn yourself into a lemon. Take that fear away because the sooner you try, the sooner you'll get good at it.

[00:27:39] Sanjay Parekh: Okay. Yeah. I like that. And now you've got me thinking that maybe I should turn myself into a lemon for these podcasts. Something to think about. Laura, this has been fantastic. Where can our listeners find and connect with you?

[00:27:53] Lauren Ramsey: Sure. So, we have a website. It's www.Betsybash.com. We're also really active on LinkedIn. Lauren Ramsey. You can find me that way. Instagram, on TikTok as well. All the socials, you can find us out there.

[00:28:09] Sanjay Parekh: Awesome. Awesome. Thanks for coming on.

[00:28:11] Lauren Ramsey: Yes, this was so fun.

[00:28:15] Sanjay Parekh: Thank you for listening to this week's episode of the Side Hustle to Small Business Podcast, powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit hiscox.com. And if you have a story you want to hear on this podcast, please visit www.hiscox.com/shareyourstory. I'm your host, Sanjay Parekh. You can find me on Twitter @sanjay or on my website at www.sanjayparekh.com.