Lindsay May, Happy Marketing Co.

[00:00:55] Sanjay Parekh: Today's guest is Lindsay May, the brains behind the Happy Marketing Co., a SEO website and marketing consultancy. The Happy Marketing Co. aims to help small businesses grow via strategic marketing. Lindsay, welcome to the show. 

[00:01:10] Lindsay May: Thank you so much for having me. I'm excited to be here. 

[00:01:13] Sanjay Parekh: I'm excited to have you on because marketing is such a critical part of small businesses. So, I'm going to love to hear how you marketed yourself to start all this up. But before we get there, tell us a little bit about you and what got you to where you are today. 

[00:01:27] Lindsay May: Yeah, so I started out as a journalist. Right out of college, I was obsessed with writing and telling stories. And so, I jumped into a local publication in Colorado.

And it was so much fun, like for a 21-year-old who got to interview celebrities and go to restaurants, I was obsessed. And I climbed my way to be the editor-in-chief of this magazine. Again, dream job. But after about five, six years, I was like, okay, I think I need more like a grownup job now. I think I need a way to get benefits, have a higher income, be able to make it on my own.

And so, I started learning about marketing. I had a minor in marketing, so I already had a base for that, but I jumped into digital marketing because that was where things were going. And being a journalist these days, you either have to go to New York or LA or travel the world.

So I was just obsessed with the marketing, social media, email, and particularly SEO, which is search engine optimization. And basically, that just helps you get on Google, helps you be visible, whether you're an entrepreneur or a business. And so, I started at the bottom with marketing, and I climbed my way to the top.

And again, I loved it. It was so fun. And as you said, marketing is so powerful and so important, but about 10, 11 years in, I started realizing, not only does it get lonely once you climb the corporate ladder, but it starts to get a little bit toxic. And so, for me, I was working 60 hours a week and nights and weekends and traveling all the time, and I thought, there's got to be more.

And so I started my side hustle. I started putting myself out there to do marketing for brands and companies on the side of working 60 hours a week. And I realized about a year ago that I could do this full time. And so even though I had been in marketing now for about 15 years, I was like, I'm going to go all in. I'm going to quit. I was at the time a CMO and I left it all behind and started my own business, Happy Marketing Co. and it's been a journey for sure. 

You know, those listening, if you're an entrepreneur, you know what that is like. But it's incredible when you can take your side hustle to the next level and realize that so many people need marketing support, and you can help them without having to work so hard and without having to experience burnout all the time.

So that's how I leaned into entrepreneurship. 

[00:03:57] Sanjay Parekh: Yeah. Okay. I got to ask you before we leave this. In journalism, you were a beat writer and then editor-in-chief. What is the coolest interview that you ever got? 

[00:04:09] Lindsay May: Oh my gosh, so many, so hard to choose from, but I would say the most random one was probably Magic Johnson.

I went to this event for a nonprofit and he was the keynote and no one was going up to him afterwards. They were just watching him and taking photos and I was like, you know what? I'm going to go up to him. So, I asked him for a photo and I got out my recorder and I was like, can I ask you a couple of questions?

And he was like, yeah, no one else is talking to me. So that was kind of off the cuff. But a dream and I had to text it to my dad and say I just randomly met Magic Johnson, but that was an amazing interview. One that I'll never forget. 

[00:04:49] Sanjay Parekh: interesting side note. We are apparently one degree separated.

I was on the same flight as Magic Johnson. I was heading to Japan and the flight stopped over in LA. Obviously he was going to LA, and if I recall correctly, did he take my seat? I think he took my seat. I was in business class as well because I was flying overseas and there was like somebody there and he was like, oh, can I sit?

I was like, yeah, and so we swapped seats at that point. He did get hassled a little bit on the flight for autographs and things like that. I did not ask him for an autograph because he was just trying to take a flight. So, let's leave him alone. 

[00:05:29] Lindsay May: That's amazing. 

[00:05:30] Sanjay Parekh: Yeah. So, you and I are one degree separated by Magic Johnson, apparently.

[00:05:32] Lindsay May: Our friend, Magic. 

[00:05:33] Sanjay Parekh: Yeah, both of our friends, Magic Johnson. I'm sure he meant to connect us earlier than this, but just forgot. So, is this your first time having an entrepreneurial experience? Is this the first time you've done anything entrepreneurial? Did you do anything as a kid, as an entrepreneur?

[00:05:49] Lindsay May: So, my dad has been an entrepreneur pretty much my whole life and kind of the smaller scale of having his own business, a market and things like that. So I always grew up knowing someone who had their own business and kind of went through that. And I never thought I would go in that direction, but I definitely got some experience from following my dad.

And now my dad is an incredible businessman, but it was so much fun to be a kid and be behind the cash register and learn concepts of being an entrepreneur and also seeing the struggles of it. So, it is my first business, but I definitely have a really close connection to someone in the family who's been an entrepreneur.

[00:06:29] Sanjay Parekh: Yeah. Do you lean on your dad for advice or, things aren't going so well, like somebody to talk to?

[00:06:36] Lindsay May: Yes. He's definitely the one where I'm like, what am I doing? Are you sure this is possible? And he's like, Lindsay, you can do this. Calm down. And he always answers my calls because the first year, especially of entrepreneurship, which he knows and everyone else knows, is tough, right?

You have so much, so many questions and so much, I don't know, in your head, you're stuck in your head. You're wondering, can I actually do this? And for me, he's been the number one person who's gotten me through that. So, it's definitely helpful. 

[00:07:08] Sanjay Parekh: Yeah. You mentioned you started this as a side hustle. And then you built it up to a point where you're like, okay, I'm going to go all in. What was it that tipped you over? Was it a dollar amount? Was it revenue? Was it like, what was it that you were just like, okay, this is, going to happen? 

[00:07:23] Lindsay May: I really was initially doing it just for extra income because I was working for a lot of startups, and I quite wasn't hitting my goals.

I had a lot of big financial things going on. And so I started at thinking, this is just extra until I find the full time job that I don't need to work extra for. And really the point where I thought I'm going to do this full time is when I was given an ultimatum where in my last job, they said, you're going to have to travel two or three times a month on top of working every day, 10 hours a day, 12 hours a day.

And I just thought, I can't do this anymore. So that was my sign that I needed to go all in. And I really didn't think I could make this work as a full-time gig, but when it happened, I realized that's what was supposed to happen all along. So, it worked out. 

[00:08:11] Sanjay Parekh: Yeah. So, was there a particular dollar amount that you were like, okay, I can make it?

Or did that happen in the beginning or at some point through? Like when did that kind of crystallize for you? 

[00:08:24] Lindsay May: So, my first month, I didn't make any money. I had zero clients that were retainers, at least. There were smaller projects that I had previously that would end. And so, I was like, okay, there's got to be a way to do this.

My second month I started making a little bit more where it was two, three, four thousand. And then my fourth month I hit twelve thousand and I was like, if I can make $12,000 in my fourth month ever in business completely on my own, then there's got to be a way to replicate that. 

So yes, once you realize, okay, like this is possible and I can actually make more than I did in my full-time job, then it starts getting really fun. But it's also scary because you're like, okay, what did I actually do to earn the $12,000? So yeah, once I hit that point, it was like, I can replicate this and it's going to get easier from here, which it did a little bit, but entrepreneurship, it's never the same exact every month.

But yeah, that really showed me that I can make this work. 

[00:09:22] Sanjay Parekh: Yeah. So is the company still just you or do you have people with you now? 

[00:09:27] Lindsay May: Yeah. It's just me. I am a solopreneur still, and I'm very A-type. So, you know, everyone's like, you’ve got to hire, you need some more support. But for me right now, I'm just enjoying, getting my hands in to all the projects and working with all the clients one on one.

So right now, I am still a solopreneur in year two now, and I will be hiring this year, but I'm not quite ready right now.

[00:09:52] Sanjay Parekh: Yeah. So, what are you going to, how are you going to think about that as you hire? Is it going to be just one for a while and make sure you did it right? Or hire a couple and see how it all shakes out?

How are you thinking about this? 

[00:10:05] Lindsay May: Yeah. The best advice that I've been given is, What am I struggling with right now in my business? What is keeping me from growing to the next level? And I think it's just having someone support me with the everyday tasks, with the operational functions. And so, for me, I will be hiring someone more in an admin level role, but being in marketing, I think they're going to be more marketing operations. Where they're helping with the project management of everything going on, and they're helping onboard clients.

That takes me a lot of time and it keeps me from jumping into a project right away, especially with a website design or SEO audits. And so having someone on the team who can really work the operations. That's where I'm going to start. And I feel like that's just going to help me get to that next level. 

[00:10:51] Sanjay Parekh: Yeah, that's great. Okay. So, it's you're going into year two. It's been a little over a year now. When you made the jump, obviously you were nervous in the beginning. Zero dollars that first month. Was there anything else that made you nervous or question what you had done and what you got yourself into, and how did you overcome that? 

[00:11:14] Lindsay May: Yeah, well, I think entrepreneurship, like I said, in corporate, I felt really lonely when I was in the C-level role. But when I made the move to entrepreneurship, it also felt lonely. 

I went from managing a team and having a boss to having no one to talk to every day. And so, for me I was like, how can I do this if I don't have anyone to talk to? No support. And so, I had to find a community of other entrepreneurs who were making it work and get in the room with people who I wanted to get to their level, who could inspire me and show me that it was possible.

So that's definitely something that I struggled with especially, but loneliness just being a solo entrepreneur especially. But once I started meeting people who were like, I did it, here's how I did it. And you can do it too. Then it just gets easier. And you realize that you're really not alone. You're not in a silo, even if you're working by yourself in your office all day, there's a whole world out there to connect with.

And that really helped me break down that roadblock. 

[00:12:17] Sanjay Parekh: Yeah. Okay, let's, let's switch gears a little bit. You did this as a side hustle for a good while. How many years were you doing it as a side hustle before you went all in? 

[00:12:27] Lindsay May: Yeah. I was contracting for five, six years on and off through my corporate job.

[00:12:33] Sanjay Parekh: Okay. So how did you manage that and manage specifically the stress of that, of doing the side hustle while working full time and then now thinking about how do you manage the stress of having a full-time business? 

[00:12:46] Lindsay May: Yeah, I definitely didn't manage it well. And I'll tell you, it was a lot of work. I was very motivated, especially financially, but I didn't realize that I was experiencing a lot of burnout.

And I think back then, only five, six years ago, I didn't hear people talk about burnout a lot. They didn't talk about how it can take a toll on your health to not have a routine and to not have some consistency in your day. And so, I went from being completely burned out and overworked to experiencing that again when I started getting clients.

And it went from having one boss to five bosses. And so for me, I really had to create that routine. I really had to remind myself that I'm a human and that I can't keep working 60 hours a week because that's basically what I was doing and working weekends just to fulfill some projects on the side.

And so for me, it was all about a schedule. I had to time block everything. Even when I had one client, I had a time block them. So I didn't get to the end of the week and say, Oh my gosh, I didn't finish that project or I worked too many hours on it. So, for me, it was just all about finding some balance and a lot of meditation to work through the stress and the questions and all of that. So, for me, it's all about balance and routine. 

[00:14:05] Sanjay Parekh: Yeah. It sounds like you're using time blocking as the way of setting the boundaries for you between business and personal. Is there anything else that you do to make sure that those boundaries stay where they are? 

[00:14:17] Lindsay May: Yeah, I feel like I had zero boundaries when I worked in corporate. So having boundaries was very important for me into entrepreneurship. And so something that I do is I cut off communication with clients and really with the Instagram world at 3pm every single day. And I know it seems like, oh, but what if you get a client who asks a question or there's something urgent going on?

And for me, I just make sure there's nothing urgent. Like I'm not running ads for clients or anything like that. And so for me, I don't look at my email until about 9am and then I check out at 3pm every single day. And I'm very strict with that. I tell my clients that when I onboard and I don't have any client communications over the weekend.

So some clients will throw in a text every once in a while and I just won't respond to them because they know my boundaries and it's never an emergency. So I just have to keep that. Otherwise, we'll go back on it and I'll be in the same place that I was. So that's really important to me. 

[00:15:17] Sanjay Parekh: Yeah, so I was going to ask about weekends. So, weekends are strictly no work. You don't do anything.

[00:15:22] Lindsay May: No work.

[00:15:23] Sanjay Parekh: You don't think about it. You don't, attack any projects? 

[00:15:27] Lindsay May: Yeah, I don't I think there's never a time that I'm not thinking about my business just because being an entrepreneur, I'm the only one kind of making things move along but no work. I'm really staying out of the DMs on social media. Staying out of my email.

And if the only work that I'm doing is personal work, like a personal development or taking a course or something like that, but I really try to stay away from overworking my brain because I think that happened a lot when I was in corporate and it's just not something that I want to do anymore.

[00:15:59] 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, business insurance experts.

[00:16:20] Sanjay Parekh: Okay, any other routines that you have? It sounds like nine to three, is email time and that's it. Outside of that, in terms of wellness or things like that, is there routines that you stick to and abide by every single day?

[00:16:35] Lindsay May: Yes. So, I wake up in the morning, I have two dogs, so I don't really need an alarm clock.

They wake me up when they're ready to get up, which is about 5am and starting about 5am after I take them out, I make coffee. I have an old school coffee pot just because I enjoy the experience of making coffee and having the house smell like it. But I don't turn on TV, I turn on maybe some light music and I do some stretching to just really get myself ready for the day and ease into it.

I think a lot of times I would jump on email right away in the morning and see like an urgent chat or something that I felt like I had to respond to. And so, for me, I just want an easy morning, stress free. And then every day after work, I'm taking the dogs for a really long walk, and making dinner, going out with friends, doing that kind of thing.

And I always end the day, with a meditation just to erase everything from the day. The stress that I have to stop thinking about my to do list for the next day. And I'm not like a super woo-woo person, but I definitely think meditation is good just to clear your mind, especially when you're an entrepreneur and there's so much going on and all of that.

So I like to end it with a meditation and no more technology after that. And that's how I ended the day. 

[00:17:56] Sanjay Parekh: Yeah. How long of a meditation do you usually do? 

[00:17:59] Lindsay May: It depends on how stressful the day was. Sometimes it's an hour long where I'll listen to a Jay Shetty meditation.

Sometimes it's just like a sound bath or something. And I fall asleep in five minutes, but it just depends on what I need in that moment. 

[00:18:17] Sanjay Parekh: Okay. Okay. So this is like meditation, basically falling into sleep. 

[00:18:21] Lindsay May: Yes. Yeah. And again, it depends if I'm like after work, if I'm stressed out, then maybe I'll add an extra one in, but usually it just helps me get ready for bed.

I might read afterwards. But just, I don't like to have stress in my life. So, I like to start the day and end the day just with a little bit of ease. 

[00:18:39] Sanjay Parekh: Yeah, love it. Is there anything that you do in terms of managing the business that technology, apps, systems that you're like, man, if I didn't have this would be just so much more difficult to do? 

[00:18:53] Lindsay May: Yeah, I mean I have a huge calendar on my wall so I can see any big things that are coming up but I put everything…

[00:19:00] Sanjay Parekh: And I can see it in the corner over there.

[00:19:02] Lindsay May: I know. I have a few different things that I look at every day.

I put everything in my personal calendar, so I use Gmail. Everything's in my calendar, even if I'm going for a walk with a friend or whatever, everything is in my calendar. So, I could not live without that. But I love project management tools. I use Asana. I've used probably all of the tools out there, but I just needed something super basic. So things like that, just get me through, just to make sure that I don't have to remember everything in my brain and it's all there to support me. 

Obviously, I'm in marketing, so I use a lot of marketing tools and Google is my best friend. But yeah, I think just simplifying the technology that you do use.

I think it's easy to overcomplicate things and have 10 different tools and then not know where you wrote a note or where you put a document or whatever. So, for me, I just try to simplify things and only use what's going to help me every day. 

[00:19:58] Sanjay Parekh: Yeah. So this is interesting. You mentioned Gmail, but yet we were both talking about the big giant calendar you've got on the wall there.

So how are those different for you? The old school hand calendar that's on the wall versus the fancy digital one that's on the computer. 

[00:20:13] Lindsay May: Yeah, that's a great question. For me, the one that I write on the wall — I have my own podcast. And so I put podcasts release dates up there, the guests that I have on the show, big events that are coming up. So kind of things that I need to prepare for. 

And then my calendar on my phone is the things of, what's happening today? What calls am I on? What are the tasks I need to get done? So stuff like that. But I am a little bit old school. I like to see the big events and things that are coming up, our launches, things like that, but the kind of smaller tasks or like the to do list, that's all on my phone.

[00:20:48] Sanjay Parekh: Yeah, I like that. I don't have a big giant calendar like that, but I probably should. 

[00:20:50] Lindsay May: You need one. 

[00:20:51] Sanjay Parekh: Yeah. Because it's exciting to see that, oh, this big thing is coming and it keeps you going up until that date. That is a good tip and I might have to do that. 

[00:21:04] Lindsay May: Yeah, you do. 

[00:21:05] Okay, so let's talk about your experience now. You've been doing this as a side hustle for six, seven years, full time for a little over one. You've learned a lot now. So, knowing what you know now, what would you go back in time and do differently based on everything that's happened to date?

[00:21:26] Lindsay May: Yeah. I think my journey, I needed all the steps that happened, but I think the biggest thing is I was stuck in my head for so long. I was stuck thinking, I don't have enough experience to become an entrepreneur, or I don't have all this income and savings to go start a business. But really it's little steps that you take to start a business moving, especially from the side hustle to the full time.

You really just have to get it organized and you have to plan out your business. And I actually did that in a restaurant. I put myself in a restaurant with my laptop one day and I was like, I'm just going to create my business plan away from my house, away from my dogs. And so, I think, looking back, I would just start sooner.

I would just go for it and get out of my head sooner, because now I know it's possible. And I think so many entrepreneurs just get stuck. And so many people who are currently in the side hustle, they get stuck thinking they have to reach a certain amount of revenue or become this incredible entrepreneur before they fully commit.

But you really do that over time and you just have to take that step and you have to go for it. 

[00:22:35] Sanjay Parekh: What's interesting is that we hear so much about the myth of the college dropout or whatever that starts the company and that makes it huge and whatever. And it's not like those individuals or anybody special had any special skills or anything else like that at that point.

And yet exactly what you said, so many entrepreneurs like, I need to go get this job and that job and this skill and that skill before I start doing this. How did you break yourself out of that for yourself? Because you obviously made that leap. But so many other people that you and I both know, won't make that leap because of it. 

[00:23:13] Lindsay May: Yeah, well, what's funny is I worked for two entrepreneurs throughout my career, so not the recent ones necessarily, who told me that I wasn't ready for certain things.

They said, you're not ready for grad school. You're not ready to start a business. And so, I was literally told that I also wasn't ready. So I was really stuck in my head. I think for me, it was just making the jump. And people have asked me, how did you get the courage? But really, I got the courage when I did it because I realized, oh, I could take that step.

And so for me, it was creating the LLC. If I could just cross one thing off the list and make it official, then I really have to go for it. I'm starting to invest money in this and now I really have to commit to it. So, I think it literally was taking action and doing it scared because I was so scared.

I had no idea what was going to happen. But that's what you have to do because otherwise I would not be here. I would still be stuck in a job that I hated. And so I think it's just, taking that first step and doing it scared, but still doing it. And, telling people in your life too, if you're like, Can you support me in this? Can you follow up with me and just ask me if I created the LLC by a week from now? 

You have to do it or you're never going to do it. No one's going to do it for you. So you really just have to take that action. 

[00:24:32] Sanjay Parekh: Well, what's funny to me is when I quit my first job, literally my first job after college to start my first company. My calculation was, Well look, if this doesn't go well, somebody else will hire me.

I mean I'm going to have a lot more skills because I'm going to have this experience of goofing up behind me. And I'm surprised that more people don't have that approach because what really is the downside? If you had done this, and it hadn't worked out, what would you have done after that? 

[00:25:05] Lindsay May: I would have applied for every corporate job out there just to get back into it, because we need income, we need all of that.

Yeah, I mean if I would have failed, I would have just done something different. 

[00:25:16] Sanjay Parekh: Right. It's not like you're unemployable after trying something and failing. People understand that you try things and sometimes it doesn't work out. So, I think that's a story and a lesson that needs to be told more to prospective entrepreneurs.

And it's unfortunate that you had the experience that you had entrepreneurs that were telling you, you weren't ready because clearly you were ready a long, long time ago. 

Okay, last question for you. And I think we've already given a bunch of this advice but if you were talking to somebody who was thinking about doing what you did and taking that leap and starting a side hustle or going all in like you did, what advice would you give them?

[00:25:58] Lindsay May: Yeah. Something that I didn't mention is I also workshopped like what I actually want to do with my business or even just in year one. Like, how do I want to start this business? What services do I really want to offer? And so, I would recommend doing the same thing. I would get out your whiteboard and say, what do I really enjoy doing in my career right now that I could help other people with?

What challenges do I want to help people with? What problems do I want to solve? And I also wrote down, what am I good at, but I don't want to do in my business? And so, I think once you get clear on what you actually want to do, and especially what you don't want to do, then I also think it gives you clarity and visibility to go toward that entrepreneurship level, right? 

I also think taking one action a day. What is one action that you can take today? Whether it's forming the LLC or just deciding on a business name. Whatever it is, take one action. Creating a business account on LinkedIn, one action that will just set you up to work toward going all in, and it'll become easier every single day because you're checking things off the list.

[00:27:06] Sanjay Parekh: I love it. I love it. Lindsay, this has been fantastic. Where can our listeners find and connect with you online? 

[00:27:12] Lindsay May: Yeah, so you can look at my website. It's called TheHappyMarketing.Co. That's where I do all my SEO and website work. You can also find me on Instagram @TheHappyMarketingCo. I'm also on LinkedIn @Lindsay May, but I love to connect with other entrepreneurs, especially people who really are interested in taking that step toward full time entrepreneurship.

I'm here to support you. I know what that's like. So, I'd love to connect. 

[00:27:38] Sanjay Parekh: Awesome. Thanks so much for being on today. 

[00:27:40] Lindsay May: Thanks for having me. 

[00:27:41] Sanjay Parekh: Thanks 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 intelligence insurance solutions, visit hiscox.com. And to hear more side huste to small business stories or to share your own story, visit hiscox.com/sidehustletosmallbusiness. I’m your host, Sanjay Parekh. You can find more about me at my website, sanjayparekh.com.