Your Guide to Navigating Common Entrepreneurial Challenges

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One of the things that has consistently surprised me is the number of people that I talk to. And I'm like, is there really like a business in that? Are there and is there a demand for that? And yet. And there is there almost there almost always is. Because what I what I have come to realize is that if you're the person with the the first mover advantage there, like the total addressable market doesn't actually have to be that big for it to be pretty big business for you.

On today's show, you'll discover the most common challenges faced by entrepreneurs and how you can overcome them. This is the launch your business podcast because we know starting a business is challenging, but it doesn't have to be confusing. Each week we'll give you the tactical advice and the necessary tools to scale your business without feeling burnt out. I'm Terry Rice, Business Development consultant and staff writer here at Entrepreneur Magazine. Let's dive in. Here's a quick story about how I got fired on my first day at a job When I was a junior in high school, I got a job as a busboy at a restaurant that was considered fancy, at least by my standards at the time. Within one hour, I was clearing plates, folding napkins and stocking shelves, and while grabbing a tray from a cupboard, I accidentally bumped into a customer. I apologized and he just waved it off like nothing happened. And then things changed. A few minutes later, one of my co workers pulled me aside and said, hey, whatever you do, do not annoy that guy. As you may have guessed, he was pointing to the guy that I just bumped into. Within a few minutes after that, I was let go. Just like that, my career as a busboy came crashing down before it really got started. And as you can imagine, I was annoyed. I mean, how can one mistake justify firing me on my first day? But that's just how it goes. When you have a traditional job, one mistake can mean you're out the door without a chance to make up for it. Fortunately, I never had career aspirations of being a busboy, so it wasn't the end of the world for me. And it reminds me of why I enjoy entrepreneurship so much. As an entrepreneur, failure isn't final, it just teaches you a lesson so you can improve going forward. And the more we share these lessons with others, the faster we can all grow. That's why I'm so glad to be chatting with Alex Freeman today. Born and raised in Michigan, Alex has found himself all over the US in his career as a performer and stage director turned podcaster and businessman. Having served as the artistic director of a small professional theater in Missouri, Alex first learned the challenges of leading a company. He turned that experience into his position as the regional sales director at broadwayworld.com, where the regional sales book has grown from about 100,000 at his arrival to nearly $1 million in four years, a period which spans the pandemic and an industry wide shutdown. In addition to hosting the Upflip podcast, which explores the world of entrepreneurship, offering invaluable insights on launching and scaling a business, he is also an accomplished audiobook narrator with many business and real estate titles to his credit. And on today's show, we'll chat about the most common challenges that he sees among entrepreneurs, why it's crucial to say no even when it's tempting to say yes, and Alex's predictions for the future of entrepreneurship and what that Means for your business.

We were chatting for a bit before we started and found out that we both live here in New York City. But do you mind sharing more of your background with our listeners here?

Yeah, it's been kind of a long, strange trip in my, in my career, starting out as an actor from the state of Michigan and then kind of discovering that, okay, so from this acting thing, I actually like directing shows. Okay, great. From this directing thing, I actually kind of like, I like the administrative side of things. And then suddenly I found myself running a small theater in Missouri. And then after, right before the pandemic, making the move to New York to kind of jump into, into a sales role in a, in a theater focused company, and during the pandemic, like, really kind of ramping up. Voice work, podcast hosting, all of that kind of stuff. So it's been, it's been a long, strange trip with, with different expertise in different spots, but, but glad to be here now hosting the upflip podcast.

I can't remember who I heard this from, but it's like there's two different types of actors. There are stage actors who maybe get their energy from the crowd. And it seems like as a podcast host, you get a chance to experience both of those because, sure, when you're talking to the microphone, you can't see your audience, but the feedback is pretty immediate. I mean, especially if you're doing well. Is that the experience you've had or am I way off with this?

No, yeah, I definitely feel that in that you do have this kind of like, there is the produced feel of it, that that kind of compares to film in that way. And that like, okay, well, if I, if I make a mistake, we can, we can edit, we can ask the question again. We can do all of those things and we can kind of get it right. But then you do get that, like, very immediate feedback of, oh, everybody stopped listening to this episode four minutes in. What did we do wrong here? How do we fix it? And how do we make sure that we're, we're kind of making that, that little tweak of like, okay, we're starting to lose the audience. We gotta, they're responding to this thing a little bit more. We gotta do that. That definitely, like, feels more like, more like stage acting, to your point.

So, Alex, thanks for not mentioning the fact that I just had to re record a question, as you mentioned, how that comes in handy when we're doing a podcast. But can you just talk to us more about your podcast? Because I realized we just Kind of launched into it without getting more background on that.

Yeah. So the Upflip podcast, we talk to business owners. Entrepreneurs. Entrepreneurs primarily, but a lot of folks in all kinds of fields who have successfully launched and started to scale a business. We catch them at different levels of scaling, whether they're closing in on the first million, or they've hit, you know, ten hundred million dollars. And now we're kind of diving into, like, how did you do that? How did you get to that. Get to that point? And, yeah, we've been around for podcasting for about a little over almost two years at this point. Closing in on episode 100, I'm. I'm 85% sure it's. It's in the can and just hasn't been released yet. But we're. We're right about that point. So, you know that exciting milestone in podcasting.

Yeah, congrats on that. And one fun thing about having a podcast is all the people that you get to meet and all the various companies they might have as well. So I'm wondering if you can think of a unique service offering that one of your guests had. And I'm asking this because often people will say, hey, look, I have this idea. It sounds kind of crazy, but what do you think? And I'll give you one example just to kind of tee it off. There's this one woman that I spoke to. She said she wanted to start an online course teaching people how to create urban chicken coops. And I was like, that is so specific.

Yeah.

But we did some research and found that the demand for urban chicken coops was there, but the supply of information on it was relatively low. And she did great with that course. It took off because it was so unique. And there's an audience is waiting for her to create it. So that's. That's my. My story. But I'm wondering if you have one you could share too.

Yeah, I think that one. One of the things that has consistently surprised me is the number of people that I talk to. And I'm like, is there really a. Like a business in that? Are there and is there a demand for that? And yet. And there is. They're almost there. Almost always is. Because what I. What I have come to realize is that you. If you're the person with the. The first mover advantage there, like, the total addressable market doesn't actually have to be that big for it to be pretty big business for you. You know, you think about urban chicken coops, how many people actually need to. Need to be interested in doing that for, for there to be enough, enough business. But similarly, I was, I was talking to a guy who had kind of wanted to get into the space of, you know, mobile auto repair, where they're going to come to your office, they're going to come to, they're going to come to it in the garage. Which in itself not a particularly unique idea. You know, I think we, we've all kind of started to experience those companies. But then what he realized as he got into the space was that the, the turnkey tech tools didn't exist for it. So everybody was kind of just like making it up on their own. And he went, oh, I think I can, I can solve this problem of like making this much easier for the people trying to provide this service. And so ended up pivoting in the midst of wanting to do auto repair into a tech company in a, in a way that really made a lot of sense because they said, okay, well let's build the tool for us. Oh cool. Now this is like running this company is much easier and ultimately more profitable than us going out and fixing the cars. Let the people who are excited about going out and fixing the cars do that. And we've now provided them a much more interesting and useful tool.

Yeah, I love that. And it shows the value of just thinking one level deeper or second order thinking. Asking yourself what if? It's like, okay, cool, what if I had this system where people can get their cars repaired at their office. That's great, but what if I want a level deeper? You know, what else could happen? And I think oftentimes we put these limits on our potential because we don't ask what if? Or just go a step further. So this is a great example of what can happen when you do. We use cloud based storage and cloud.

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Another question I have is going to be related what are some other common but avoidable mistakes that especially emerging entrepreneurs make?

Yeah, I think one of the things that's been most interesting to me is the number of people that I've talked to who simultaneously were surprised by how quickly they scaled. And so it's in, in some way they, they like, they, they tried to do a shortcut in setting up the company and then that ultimately caused them a headache. And the simultaneous advice of like, don't necessarily make the full investment in like incorporating and spending like the thousands of dollars that come from that before you really have like tested out your product. And so I think like falling into that middle ground of being prepared to make the business structure shifts that you're going to need to make if and when the company takes off while simultaneously keeping yourself low costs upfront to actually test the idea. I think that that falling somewhere on the extremes of that spectrum is probably the, the biggest mistake that I've heard people making. And certainly I feel I've watched myself make in my own, in my own kind of business endeavors as well.

Now let's, let's dig into our own, we'll call them challenges that happened during our career and I'll bring up mine. When I first started my business, I was also teaching at a school called General assembly. And as a result of that I was leading workshops for my target audience like three times a week and getting paid for it. So I was getting paid to deliver workshops and the attendees would often hire me to get one on one help, which was great. And I was easily pulling in six figures within just a few months because of this process I had. But it also made me very lazy. I had no clue how to actually get my own clients. And when people came to me and said, well Terry, how do you, how do I grow my business? You know, and I was like, oh well, I only have one channel and you already saw it, right? So I couldn't grow quicker And I couldn't help other people scale their business because I was just being spoon fed lead. So that I would say set me back about two years in regards to becoming a more like, more full fledged entrepreneur because essentially all my leads are being sent to me and I didn't know how to get them outside of that context. So that was my mistake, which I've remedied since then. But if you don't mind sharing one of yours, I think that would be helpful.

Yeah, I think for me one of the biggest things that I have constantly struggled with is the, the biting off more than I can chew side of things and, and not understanding. Oh, if you leave yourself space, if you're not afraid to say no to, to a potential opportunity that you look at and you're like, ah, this is like a lower rate than I want but like if I but a lower rates better than no rate. And it's like, no, that's I'm constantly fighting that in myself of taking on like lower pain things when you know, the calendar looks empty. It's, it's learning, learning that fact that it is more worth my time to try and to not have something that I'm working on to go find the higher paying clients to go find the higher paying thing that will more than make up for maybe the, the couple of days that there isn't a, a client actively on the roster in that spot.

Yeah, I think it was Alex Hermosi said a lot of people can't make big money because they won't turn down fast money.

Yeah.

And that really stuck with me too because you know what it's like when you're looking at your calendar or like your monthly recurring revenue, you're like, wow, it's kind of dipping. And then you're tempted to take these lower paying jobs but then all of a sudden something big comes and you can't complete that as well because you're working with these other people. So that's a good cautionary tale as well. But I want to go back to your early career because you're a creative and now you're doing like, you know, business, business work too. How do you balance that out? Because sometimes I'll get in flow state when I'm creating content. Maybe I'm writing an article or script and I get almost annoyed when I have to like attend a meeting or like, you know, just do some kind of admin stuff that I can't give to my assistant. So how do you find time to both create content and express your creativity but also run a business as well.

Oh man, Terry, if I had the answer to that. That's a billion dollar idea, I think. No. Yeah. I mean, it's really, really hard. And like, it's, it's. For me, it's really being conscious and clear when I'm setting my calendar for the week and, and, and understanding. Okay, like, for me, for me, Thursdays are just like the worst day of the week because I end up having to do a little bit of work on every, every single facet of, of what I'm up to and not. And it's always, it is like pivot, pivot, pivot, pivot, pivot. And flow state is not, not possible on Thursdays. But I can like, you know, look at my calendar and be like, okay, great, like, like Wednesday morning. This, this week is pretty much wide open on the calendar. And I know that it's wide open. So as, as the inevitable things come up in the, in the calendar, making sure, like, okay, protect the open space where, where I can actually like, get into flow state on a project. What's the biggest problem I need to tackle on Wednesday morning in this particular week? And, and how do I make sure that we, you know, keep that, keep that safe and secure so that I can achieve, achieve that certain level of flow state? But yeah, I mean, it's there, there are some, there are some weeks where I'm awful at doing that. And I get to the end of the week and I go, well, did not accomplish nearly the things that I wanted to accomplish. A lot of things got done, but I don't think I accomplished anything.

Yeah, that's, that's tough. I mean, even before we hopped on, one of my partners asked me if I could meet tomorrow at 9:30 for something. Right? That's when I'm at the gym. So I try to schedule my work life around my personal life, including going to the gym. So hopefully they're not listening to this podcast because I have to give them an excuse for why I cannot Talk tomorrow at 9:30. But the thing is, if you give an inch, all of a sudden that turns into miles. And at the end of the week you're like, or end of the month you're like, I haven't done any of this stuff because I kept on making these concessions. And sometimes the concessions, it goes back to our last conversation where there's a client that wants to meet you, like a new client, and they're saying, hey, Alice, can you meet Wednesday at 9:30? You know, you have that time blocked off for creative work. So.

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I'll pose that to you. Alex. What do you do? All right, you have a client who wants to work or a prospect who wants to Talk to you 9:30 on a Wednesday, but you had that block time blocked off to write some amazing blog or work on your podcast. What do you do?

It is a tricky, tricky situation. I mean certainly it's like, it's weighing the opportunity cost. It's, it's saying, okay, where, where does this client, you know, all of our clients are favorite clients, let's be clear. But where does this client kind of like rank in the terms of like, okay, if I accomplish these things that I was planning to get done on Wednesday or even just even like if I go to the gym on Wednesday at 9:30, what is the rest of that day going to look like? Am I going to be, I know that I'm, you know, more effective if I've gotten my workout in, if I've done these, if I've done xyz. So I, I have to say, I have to say no in those spots. But my hope is that more, more and more of us are, are talking about these things and how important that like, you know, like we use the phrase work life balance, but it's really like it's really just like one life and there's, there's not necessarily like what is it, what does it mean to, to be balanced between your work and your, and your quote unquote life? You know, if you're pursuing the things that you want to be pursuing, you're doing the things that you want to be doing and sometimes that means that you have to, have to do things you don't want to do. But that's part of pursuing those things you do want to do. It all just kind of like feeds into one calendar and, and then like usually what I'll do in that situation with the client is I'll say I can't do 9:30. Here are, you know, three, four other alternative times and then here's a day of the week where like you tell me the time I will make it work into to meet with you. So it really certainly feels like it doesn't come across as like, no, I'm going to the gym, you're not important to me. It's like I have this thing as previously scheduled. I got to get it in then or it won't happen. Here's all of these other times that are available for me. Let's find the compromise.

Yeah, there's this one guy I used to work with, he was a sales, sales rep and he would never say no to a client. He would always say what he could do. So you're taking a similar approach here. And as we're wrapping up, let me ask you one more question here. Actually I'll give you two options for the question you want to answer. What trends are you seeing in entrepreneurship that you find to be notable or what predictions do you have about entrepreneurship that you would like to share?

I think I'll take predictions, I'll take predictions in that I predict that the skills of entrepreneurship, not necessarily the, the ability for everybody to, to take that massive leap of faith and start a business, but the skills of entrepreneurship are so important to have even when you're working in someone else's company in, in almost any role that that is truly what people want is they want people that are entrepreneur esque in their companies working is that I think that we'll start to see those skills come, come more into the fore in like primary school education. Like we'll start to see teaching like decision making because more and more facts are easy to find, also easy to make up. But that's a whole different discussion. Facts are easy to find and so like your ability to like know exactly. The thing is is less and less important. But your ability to go find the answer and your ability to then implement the answer are increasingly important as we move further and further away from the days of schools creating factory workers, now schools need to create thought leaders.

Yeah, and I think that's true for anyone. I mean adults, children, you know, whoever it is, because information is largely free and available, but the actual curiosity to even explore it and the resolve to apply what you've learned to is what we're missing sometimes. So I think you're, you're spot on. And that's why I also feel like the best entrepreneurs, maybe they don't even need mentors because they can just learn from people remotely and they don't necessarily need that one on one attention. I'm not saying it's not useful, but if you're really driven and really curious, you can make a lot happen just by observing people and leveraging self education.

That's why I think like the Mastermind model is more interesting than like the mentor mentee model in modern days is that like get together with other people that are, you know, more or less in the same, same realm as you and kind of pursuing the thing. So you do have somebody to bounce the ideas off of live. But yeah, like sit around it, like talk about, you know, what you just listened to on the launch, your business podcast or the UPFLIP podcast, right? And then say like, okay, great. How does that, how does that actually apply to my business? How does that apply to what I'm trying to do? And so that somebody can like call you out on your crap when you, when you are like espousing something and they're like, yeah, but you're not doing that.

Yeah, I love it. So Alex, we talked about a lot, but I know people are going to want to learn more about you, so what's the best way to do so?

Yeah, I'm, I'm on LinkedIn. Alex S. Freeman on LinkedIn. I, I'm, I'm recently converted to threads. Alex Underscore S. Underscore Freeman over there. And then make sure to check out the Upflip podcast wherever you're listening to your podcasts.

And that's our show for today to learn more from Alex and his amazing guests. Be sure to check out the Upflip podcast and if you got value from this episode, help us spread the word by sharing on social and leaving a review. Thanks again for listening and I'll catch up with you next time. Apply what you've learned on today's show. You'll find the show notes and more resources at TERRYRICE CO. Again, that's TerryRice Co podcast, and the best way to support this podcast is by subscribing, telling a friend and leaving a review. Also, you can get more tips by following me on instagram at its terryrice or follow me on LinkedIn. This episode was produced by Josh Wilcox of Brooklyn Podcasting Studio and edited by Dan Lardy. Special thanks to my wife Dominique for keeping our kids relatively quiet as I recorded. Thanks again for listening. I'll see you next time.