The Skinny Confidential Him & Her Podcast - Solo - How To Start A Side Hustle Or Your First Business To Generate New Income

Episode Date: May 3, 2024

#695: On today's episode Michael is solo discussing practical steps to start a side hustle or your first business. Michael disucsses the early days of starting a business or side hustle and the mindset and sacrifices that need to be made in order to generate a new income stream or stand up a new business. Michael also disucsses practical ways to slowly transition into becoming a business owner and ways to make your side hustle worth your while.    To connect with Lauryn Bosstick click HERE To connect with Michael Bosstick click HERE Read More on The Skinny Confidential HERE To Watch the Show click HERE For Detailed Show Notes visit TSCPODCAST.COM To Call the Him & Her Hotline call: 1-833-SKINNYS (754-6697) This episode is brought to you by The Skinny Confidential    Produced by Dear Media

The following podcast is a Dear Media production. My daughter and I love to bake. We bake probably four times a week. We do sugar cookies. We do cupcakes. We do pizzas. We just like love to be in the kitchen together. And I cannot believe it, but up until recently, I just had regular baking sheets. I already had switched all of my pots and pans to Caraway. I even got their pizza cutter and garlic press, but now all my bakeware is switched to it. I'm really passionate about this brand specifically because I think it's such an intentional, thoughtful way to switch something in your kitchen to non-toxic. You guys know I've been on this non-toxic journey for a long

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you can take an additional 10% off your next purchase. This deal is exclusive for our listeners. So visit carawayhome.com slash him and her, or use him and her at checkout. Caraway, non-toxic cookware made modern. She's a lifestyle blogger extraordinaire. Fantastic. And he's a serial entrepreneur. A very smart cookie. And now Lauren Everts and Michael Bostic are bringing you along for the ride. Get ready for some major realness. Welcome to the Skinny Confidential, him and her. Lauren and I are getting ready to kick it back old school and do an episode asking a bunch of Q&'s that came

through on a recent post that she just posted where we're going to answer listener questions for long time listeners of this show. You'll remember that's actually how we started the show. There was an ask him and her hashtag, and we used to facilitate questions and then answer audiences questions. And so that's really how the whole show started. That was the idea of it in the beginning. It's obviously evolved, but I realized as those questions were coming through that since the time has passed since the last, you know, over the last eight years or so, since our businesses and lives and things have evolved, some of the kind of like the basic core competencies of the things we used to talk about and things that have been proven since then maybe don't get talked about enough in recent times. And we can also maybe share a greater expertise now that we have a little bit more experience for people that are maybe earlier on in the path. So one of the topics that comes up on this podcast a lot is around personal finance and how to save and how to invest. And what I was thinking is one of the core competencies around that, not only how to

implement those strategies, is also how to generate more income. And I feel like talking about that is just as important as talking about what to do with it. And so I want to tailor this episode from my perspective, again, I'm not claiming to be an expert in every area, but I do have now what I would say some experience in launching businesses and multiple different endeavors and arenas and at multiple different scales, side hustles included. So I want to tailor this episode to people that are earlier on in the path thinking about potentially launching a side hustle or a business of their own. Maybe they're working a job and saying, hey, I want to generate a little extra income with a side hustle. Or maybe they're thinking about taking that leap and becoming an

entrepreneur and leaving their current gig to go start a business of their own. And I want to talk about some of the early days around what that looked like for Lauren and I, and I'll tailor it around this podcast specifically, namely because this podcast started as a side hustle where Lauren and I were running other businesses and other companies or had different jobs at the time. And off the success of this podcast, obviously there's been businesses built, including Dear Media and some of the things we've done in the commerce space. So I think it's relevant to talk about some of the early days and what that could look like. And again, you don't

have to launch a podcast or something in the media space, but I think some of what I'm going to say here is relevant to anyone. So first, I'm going to tailor this to people that are maybe, you know, maybe they're happy with their job, have a gig, but they're looking to earn a little bit of side money and have a side hustle of their own. And I want to talk about what that looks like. First, if you have a passion or idea for anything, for us, it was speaking. I would lean into whatever that passion may be. For Lauren, it was scrapbooking. So for her, it looked like a blog. For some people, that's personal shopping. So they start linking out. For others, they have a real passion about health and fitness. So maybe they become a trainer or they created a course online on how to take care of someone's fitness

needs, whatever it may be, whatever your passion may be, whatever you feel excited about, whatever lights you up. For me, again, it was talking. Lean into that when you're thinking about a side hustle, because the difficult thing with a side hustle is if you trade a side hustle like a job, it's going to be hard to sustain it in the beginning when you're not generating an income. To give you some context, when Lauren and I started the podcast, I was running two separate businesses. She was working two separate jobs and running her blog. And we just knew that we would be passionate about talking on a mic together. So there was no intention to make any money in the beginning. There was no intention to have it be a business. It was really the exercise was,

could we do this podcast for a year together passionately and with excitement? And could we potentially build an audience that's interested in what we have to say? There was no thought on how much money could we make. There was no thought about building a business like Dear Media. There was no strategy around things that would live off of this podcast. It was literally, if we decide to do this, could we stick with it for a year with no money? So if you're thinking about doing a side hustle, I think that should be the number one criteria.

Is this something you would be excited about doing for a year with generating no income while you're supporting yourself, either with a job that you currently have or a company or whatever it may be? Because the reason I mentioned that is if you can do that and get in that mindset to start something as a passion project, that one, you're going to be excited about, one, you're going to stay with it. And two, then if you're going to stay with it, you're going to have the consistency and the longevity to refine it along the way, which is really important.

Okay. So what it looked like for Lauren and I in the early days, we had both jobs. We had other income streams. We would podcast on the side when we were done with those jobs. We started it from a very kind of version one, version A of this show. If you go back and search the Skinny Confidential Hemingway Show episode one, it's still on YouTube. It is atrocious. We're interrupting each other. We had no refinement. The topics were all over the place. The sound was bad. We literally went and bought two to $300 worth of equipment and use that equipment. Googled how to work it ourselves and started filming with a camera that Lauren had that she was using for her blog. On the video side, we had one shot,

and then we used a couple of shitty microphones. And the reason I mentioned that is if you've listened to this show for a while, you'll hear me say launch fast and adjust on the way. There's a lot of different headlines now around this show and around Dear Media. And what I like to try to point out to people is all of this was started really from the podcast side in 2016 with $300. And it's obviously grown since then. But I say that to bring awareness to anybody that's out there. You can start a side hustle or start something very, very small and work to grow it. So again, we started with a theme. It was talking to an audience, answering their questions, getting them involved, you guys involved in the

show so that we had feedback so that they felt part of it so that we could grow with them so that we felt we were part of it. They felt they were part of it. And we just started this process slowly. As you start to think about creating a side hustle like this, I think it's really relevant to start tapping into a core demo of people. It could be five, 10, 15 people. Don't think about thousands and hundreds of thousands and millions. If you start thinking that way from the beginning, you're going to struggle because when you're not there in the beginning and you're looking for those numbers, they become really daunting. So we live in an age now where people are going viral and audiences are building very quickly. And you'll see something from a creator or a business owner that's further along with more

revenue or more customers or more followers, and you'll get overwhelmed. In the beginning, your sole job is to build a small audience and a small consumer base and consistently serve them over time. And this doesn't just have to do with creating content or media businesses. If you have a product and you're selling even five items to a customer, get in touch with those customers at the beginning, ask what you can do better, ask what they like, what they dislike, you know. Really just work to cater to that demo early on because those are going to be the people that do all of your marketing later on. Okay, so lesson number one, you have a passion. You lean into that passion.

You set up a structure that you can work within for at least a year without any anticipation of money and you support yourself with the current job that you're in. This is going to mean that you're sacrificing time on the weekends. It's going to mean you're sacrificing time with friends. It's going to mean that you have to make some sacrifice to allot the amount of time to do that. And you have to at least allot yourself one year, in my opinion. This goes for a business as well. When you're starting a business, I do not think it's a good idea to abandon everything else you're doing. I would pick something that you can do for a year period of time. If it's going to be a business structure, I would speak to a council about which type of entity is right for you. In most cases,

it's going to be an LLC or an S-corp. I would definitely spend the money to set up a structure and not do this on your own. Anything that Lauren and I have done, we've always made the investment to set up a company for an assortment of different reasons that will make themselves apparent later on. Speak to an attorney and speak to your CPA about what it looks like to set up a company for whatever type of entity you're going to do, whether it's a commerce business or a media channel or whatever it may be. Okay. So early days for us, that's what it looked like.

We had jobs. We were supporting ourselves with those jobs. We were consistent. We made sure never to miss a moment. And then as the business evolved, we started refining it along the way. As it started to get some traction, we picked a number. And I'm not going to say the number because everyone's going to have their own individual number. But for us, the number was what is a quarter of what we make as a couple with the jobs and companies we have that if we got a quarter of that revenue, we could use that money to support this new business endeavor. And so we started backtracking.

So let's just say you pick a number, I'll say $10,000. So you pick 10,000 that you want to earn in a year from your new side hustle. Work backwards. That's roughly about $800 or so, $833 or so a month that you need to earn, which means roughly call it $200 a week that you need to earn. Figure out what you can do and what you can implement in the business to make that small amount. If you sit down on a piece of paper and you write 20 ideas of how you could start generating that specific income, whatever it may be, you'll be surprised. The first four or five ideas are going to be easy. The next 10 to 15 are going to be a little harder. The last

five is likely going to be where you find your answers on how to generate that income. So we slowly did that. Again, this was years and years of just doing this, supporting ourselves in other areas, launching, making sure that as we got feedback from our audience and customer base that we were refining, okay, less interrupting. hey, we'd really like you to talk about these things. Oh, can you go into these subjects? Spending a lot of time with the community to figure out what they actually wanted. And then when it became time to start monetizing, we had picked a specific number and had backtracked on how we got to that number. If you notice, we had not burned all the boats and we had not jumped into the thing. We were still able to support ourselves.

And so any found money in this endeavor that we were passionate about, again, I'll go back to the passion, we're excited about doing it and would do it for free, was like found money for us. And it was just like icing on top of the cake. We took the majority of that and just put it right back into the business. In this case, the podcast got better equipment, got some help, started spending more time. And then after that, we picked a number and said, okay, this is the number that it would require for us to stop our current jobs or to focus on this full time. And we did the same exercise. Okay,

now we have a small amount of money for us to make the leap and make this side hustle or business a real business. Then we took the time and said, okay, what is the number for us to abandon the other stuff so that we could work full-time on this? I think the difficulty for people when they're thinking about starting a new endeavor is they distract themselves with steps A through Z and they don't think A to B what they can do that day

and they overwhelm themselves with all the different things. If I was gonna pull the lens back a little bit here and imagine if I had the idea of Dear Media from the beginning, and I said, okay, I'm going to start a podcast. And then that podcast is going to become successful. And then all these people are going to listen. And then all these brands are going to pay to fund it. And then that funding is going to lead to me launching a whole network that's then going to fund commerce businesses that's going to then have 90 shows and 50 employees and all that. I would have been so overwhelmed. There would have been no possible way for me to do this. So the advice that I give to people that I speak to now is, what is the first thing that you can do? What is A to B? And once you've done B completely,

what is B to C? You're going to give yourselves 18 different reasons to be overwhelmed. If you think so far ahead, you should have an idea and a vision of what maybe you might want to do or might not want to do. And again, that's going to change and be refined over time as you execute on your plan. But if you think so far ahead, you'll stop yourselves from executing. And what I see is such a tragedy to so many people that I speak to is they have these great ideas, but they never execute on them, whether that's a side hustle or a creative endeavor or a new business, because they keep waiting for that moment to be perfect and waiting for all the dominoes to be aligned before they execute. And if you look at what we've done in this space in particular, nothing's ever

been perfect and nothing's ever been lined up. Honestly, just bulldozed our way into the space by executing consistently and constantly all the time, one foot in front of the other, never thinking too far ahead. And I think that makes all the differences. You have a lot of dreamers and a lot of talkers, but you have very few executors. And I say that bluntly because I want people out there to think about the actual actionable steps that they can take on their side hustle or business venture today, right now. If you stop listening to this podcast and you have this idea and you've been sitting on it, what is the thing you can do today? You're going to build what I call momentum

and you need momentum in any endeavor, whether it's a side hustle or a business to carry you forward in the path as you go along. And if you don't start building that momentum by taking the tangible actionable steps on each process along the way, you're just going to continue to stop yourself from getting going. So for long-time listeners, if you've heard me say it, it's launch fast, which means go now and adjust as you get consumer feedback along the way. This show has changed multiple times and has had so many renditions and our interests have changed and Dear Media has changed and the branding's changed and been updated. And if you've been paying attention, you see that what we do is we just wait for that feedback and we just slowly adjust along the way. So once you get your side

hustle to a place where it is generating an income that can replace your main income, you then have the decision to make of, okay, you can keep your job and work too and have side and main as something that supports you. Or maybe you've started your business venture and that is now starting to be a venture that can support your lifestyle and you can abandon the other ventures. That's a critical moment because in our case, we stopped working on some of the other things we were working on. I actually left the companies I was with and went full-time into podcasts and dear media, and then slowly have built that along the way. But I think the first tangible steps are, what is your passion? What can you be consistent with? How can you start to slowly replace income and look at that new income as just icing on top of what you're already

doing? And then with refinement and feedback along the way and taking tangible, actionable A, B steps, A, B, C, D along the way, can you then make that side hustle or that business your main thing? And so this episode is really tailored for anyone that is thinking about leaving their job, thinking about starting a side hustle, looking to earn a little bit more income, looking to figure out what those first steps are along the way to get going. And what I would say to you is just find something you're excited about and get going and know it's not going to be perfect and know that you're probably not going to make any money for the first year or two and that that's okay. Listen to the audience or the customer base that you do have.

Tailor their experience to a point where they feel so good about it that they want to go sing high praises to everybody else. And then pick tangible financial benchmarks that you can use to slowly replace your current job or your current business or not replace at all and just decide that, hey, this is just extra money. I think sometimes people say save or invest and they don't realize you might be living paycheck to paycheck and you might not have the opportunity to scrounge out anymore. You might not have any extra left even after making the cuts and the sacrifices that you need to make. So creating a side hustle or a new business that you've been thinking about is relevant. And again, it's going to require a

sacrifice of time and there's going to be a commitment and it's not going to be easy. But if you've been waiting to do that, now's the time. Get going. Pick the first actionable steps. Pick something you're excited about. Slowly do it. Be okay with the long process. And you never know what that leads to. If you would have asked me eight years ago if I'd be sitting here doing this, running a company like Dear Media, sitting on different commerce businesses, representing shows outside of our own, partners like the ones I have. I would have looked at you with a funny look, but it's all taken place because we've taken this step-by-step A, B, C, D approach and just taken it as it's come and been really

patient along the way and made sure that the audience we're speaking to feels included and heard along the way. And I think many of you can do the same. So that's my spiel for the day. If you've been thinking about that side hustle or starting that business, start it now, turn this podcast off, go do it, stop procrastinating, stop giving yourself excuses, stop waiting for the perfect moment. It's never coming and just get going and adjust along the way. See you next week.