Navigating Entrepreneurship's Unexpected Challenges with Caitlin Saenz

0:02Who's ready to rock today, Fire Nation? JLD here and welcome to Entrepreneurs on fire brought Brought to you by the HubSpot Podcast Network, the audio destination for business professionals with great shows like Billion Dollar Moves. Today, we'll be breaking down how to navigate entrepreneurship's unexpected challenges. To drop these value bombs, I brought to Caitlin Sines and the EO Fire Studios. Caitlin is the InsureTech leader at CoverHound Insurance Solutions. She's an entrepreneur, speaker, writer, problem philosopher, grit coach, and she supports small businesses and their growth and scale journey through insurance.

0:34In today's Foundation, we'll talk about what is keeping small business owners up at night, how to better manage uncertainty, the role that grit plays in entrepreneurship, and so much more. And a big thank you for sponsoring today's episode goes to Caitlin and our sponsors. Hustle & Flowchart, hosted by Joe Feer, is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Join Joe as he discusses systems, mindset tweaks, reframes, and strategies to help you build a business that gives you freedom and fuel for your life. A recent episode on using AI for effortless content creation is a must listen.

1:05Listen to Hustle and Flowchart wherever you get your podcasts. Want to meet me, JLD, in person? Attend Clay Clark's two-day interactive business workshop and meet me, Tim Tebow, and Clay Clark this June. Experience the highest rated business workshop in America and hang out with me in person at thrivetimeshow.com slash eofire. Again, that's thrivetimeshow.com slash eofire. Learn more and request your tickets at thrivetimeshow.com slash EO fire. Caitlin, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. Hello, Fire Nation.

1:43One of the biggest things about coming successful that people would disagree with would be kind of the sacrifice that comes with it. I think that we all know becoming successful might be hard work and it might be this or that, but to be successful and to be able to put energy into that means that other energy or time and things, resources have to come from other places. And so I would think of Oprah as an example, which is an extreme example, but she's very successful by most definitions, right? She talks a lot about having a really bad relationship with her mother and how her success railroaded that.

2:17And so I think that's a sacrifice, whether it's good, bad, indifferent. For me, it's the sacrifices that come along with it. And Fire Nation, that is right on theme with our conversation today, which is all about navigating entrepreneurship's unexpected challenges. You know, we all expect something and have expectations about the challenges that we're going to face. But what about those unexpected challenges? And I want to talk about the elephant in the room. What the heck, Caitlin, is keeping small business owners up at night? I think if you were to ask them, you'd get a wide variety of answers, They would tell you very specifically what's keeping them up.

2:53But the bigger piece, if you were to sum all that up, is uncertainty. It's uncertainty about what might be coming, what obstacles might be coming, uncertainty about supplies, uncertainty about laws that might impact their business, but it all comes back down to that uncertainty. So Fire Nation, one thing that I really want you to think about is that word uncertainty and what it means to you. What would you say the word means to you, Caitlin? To me, uncertainty just means that feeling underneath of not knowing what's going on, not being able to control certain aspects of your entrepreneurship journey, your business, your life in general.

3:32And sometimes not knowing what to do with that and then managing it to the best of your ability. Because if you get stuck in being too uncertain, being too afraid of what may or may not happen, it can be detrimental for your business. Now, I want to do a deep dive on your opinion on how we can better manage this uncertainty that we're talking about. Take it away. There's probably therapists out there that have books about this, you know what I mean? Like how to manage that. But from my perspective, it comes down to like mindset first and foremost. And then secondly, it's kind of risk management, which is really interesting.

4:07But again, something that we all do in life and that we all do in business. So if you're going to be dealing with uncertainty, which everyone is, the first thing you have to understand is like, what's my mindset about this? Is this going to be crippling? Is it truly keeping me up at night to a point where it's detrimental? Or is this something that I can learn to be comfortable with and learn to kind of work through? And then what does that look like, which is so individual for each of us. But you got to have the right mindset. You got to be okay with that. And you have to have certain risk management that can help you get in the right mindset and also help manage some of that uncertainty.

4:43You could be uncertain about 100 things, or you can do some risk management and be uncertain about 50. And I don't know about you and Fire Nation, but I'd much rather be uncertain about 50 things than 100. Now, you just say mindsets. So what specifically should our mindset be, in your opinion? Can you give an actual example of what that would look like? Yeah, absolutely. I'll kind of take it in my perspective, right? I run an insure tech brokerage, and we have a digital platform. We got acquired three, four years ago, now almost four years ago, which is a really uncertain time. Like post-acquisition, what's going to happen?

5:17Are there going to be layoffs? Are they going to keep certain aspects of the business? Are they going to sell it off? Are they going to close it down? There's a lot of uncertainty that comes with that if you haven't been through that kind of transaction before. And when it comes down to mindset, like A, you can choose to be in the mindset of all the bad things that you think could happen are going to happen. And you can try to plan and risk manage around that. Or you can be in the mindset of like, I know my worth. I know what's going on. I know what I bring to the table. I know what I'm capable of.

5:46I know what I can produce. I know my contacts, my network, and just have that like, even though it's uncertain, I know I'm going to keep putting one foot in front of the other and I'm going to make this the best damn business I possibly can. And whatever happens is still going to happen. I love that. And Fire Nation, I hope you're fired up about that as well. And I want to talk specifically next, Caitlin, about grit. What exactly do you define the word grit as? How would you actually define that word? I love that word. That's my favorite word. Grit, how I would define it, I think grit is made up of four key pieces.

6:22And grit is an essential ingredient in any business, any hardship, and life truly. But I define grit as essentially having goals, resiliency, intuition, and tenacity. And some of those words feel like, are they similar? They are, but without the other, they're not going to get you grit. And so when I think of grit and I define grit, those are the four words that kind of go into it. And with those four things, those four words, those four practices, you can be gritty. You can get through the hardship. You can get in the right mindset. So you're speaking to entrepreneurs, to small business owners, to solopreneurs, to entrepreneurs, to side hustlers, to, again, people that are both running businesses that are maybe a couple years old, to just starting out, to anywhere in between.

7:13So what role have you found grit plays specifically in entrepreneurship? To me, it's the key ingredient. So you can have fantastic ideas. You can have a great network. You can have the right marketing. You can have the right production. You can have all of that, but without grit, without being able to manage what's naturally going to come, you're not going to be able to get through. You're not going to be able to be successful and you're not going to know which sacrifices kind of going back to that original question makes sense and which sacrifices don't because there's got to be a line, right?

7:47Which is different for everyone. But let's say you're a solopreneur. We'll use my husband's business, for example. He is a fantastic carpenter, woodworker. It's not his main thing, but like he is really good at it. Like I met this man at 20. He's built a bar in his like dining room. I'm like, I don't understand. Out of wood. Wasn't pretty, but it was effective. And so he wanted to create designer wood tiles, kind of like you would create a tile in a kitchen. And he wanted to market it. That's all great and dandy. He's bringing a new product to market with like no network, no ends in the, you know, anything like that.

8:22And there were several setbacks. Like one wood skyrocketed out of nowhere. And this was, again, a few years ago. So the price of lumber tripled, quadrupled. So that in itself was a problem. He wasn't able to find wood types that he needed. Because the prices of wood, other supplies started to shift. At that point, also, people were a little unsure about buying designer tiles. So all of these things are uncertain. All of these things are impactful to that solopreneur, that man who's just trying to get this off the ground. And without the grit to try to problem solve and say, no, my goal is important enough.

8:57And my intuition tells me I have a really good thing here. People love this. When I show this, people want it. And I've got the resiliency, meaning that when I found out about wood prices, I was able to pop back. I was able to find different avenues, think about different ideas, approach things differently, try different substrates. And he had a tenacity to say, I'm going to keep going. I can keep this momentum and I'm not going to stop. And so that is the role that grit plays. That's the difference between him trying to launch something and deciding this is way too hard and this is not the right moment versus him saying, no, this is coming and I'm going to figure out a way to do it.

9:29And all of our entrepreneurs, solopreneurs, wannapreneurs are going to be in that situation at some point or another, early, late, both, all of the above. Fire Nation, think about the role that grit has played in your journey thus far. And we just got a great example from Caitlin. I'm going to ask her for another one. When we get back from thinking our sponsors, every entrepreneur knows that growing a business is hard. Trying to figure out which software to use, when and for what purpose can be frustrating. You've got your email marketing system, your payment software, your CRM, your content tools, your email tools, your tools to retool your tools.

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11:49Become the next success story and request tickets to join Tim Tebow, myself, and Clay Clark at the June Business Conference today at Thrivetimeshow.com slash EOFire. This episode is sponsored by BetterHelp. Can you believe we're already halfway through 2024, I mean, time flies, especially when you're head down trying to grow your business. But one thing I've done consistently for the past 12 years is check in on where I'm at with my goals. Now is a perfect time to do that. And therapy can be a huge help when it comes to taking stock of progress and making adjustments for the remainder of the year.

12:22That's right. Therapy isn't just for those who have experienced trauma. It can be incredibly helpful when it comes to learning how to set boundaries, leveraging your time most effectively, and getting back on track with your goals. Not sure where to start? Give BetterHelp a try. It's not only super convenient and flexible, it's also easy to dive right in. Just fill out a brief questionnaire online and get matched with a licensed therapist. Take a moment. Visit betterhelp.com slash fire today to get 10 % off your first month. That's betterhelp.com slash fire. All right, Caitlin, we're back and you gave a great example of the role that grit plays in entrepreneurship.

13:02I really love that as a personal example. What's another one where you really were like, wow, grit is playing a really huge role in this person's entrepreneurship journey. I can actually think of one of our clients. Again, as you think about uncertainty and not knowing what's happening, we insure a bookstore. And this bookstore is a small, local, independent bookstore. It's in a community, fantastic people. And one week, a car ran through their bookstore. Luckily, no one was hurt. There were no barriers in front of it. It wasn't like a big shopping center or a new building or anything. And literally, a car went through their bookstore, took out, I don't remember the percent of inventory, but probably it was upwards of 20%.

13:46I do know that. And so that's a really big moment. So as an independent bookstore owner, this person took their savings, they took retirement, and they were like, I'm going to open a bookstore. So that in its own self is like huge. They've had to buy inventory. They've had to, you know, rent, lease a building, all of those things. And so at that moment, they're like, I don't know if I want to keep going. This has been an uphill battle. I was finally starting to like make some money, right? Still not profitable, but like on the cusp. And now I have to go like buy new inventory. I'm going to be closed for a certain amount of time.

14:17It was, it was very intense. So that's a decisive moment. And the role that grit played was saying like, no, there are options here. There are solutions here. I don't know them. I'm very uncertain about like what that looks like, how long these things will take, but I'm not giving up. And so because we're, you know, part of this bookseller community, I understood there was a charitable place that would essentially help bookstores. Like that's their mission for things like this. So I'm like, you need to call them. On top of that, they were insured very well. And so like, Hey, like, yes, you're going to have a deductible, but like, again, this is not the end of the world.

14:49We can help you out. And you have business interruption coverage, which I know is very techie. But still, the fact that you can't be selling right now, you've got some coverage for that. And all in all, because that person decided instead of like, I'm just going to close down and cut my losses, they had an action plan. They worked through. They stayed resilient. And they're open. They're doing better. This is their third year in business now. And they're profitable. And it's really cool to see them continue to grow. And they're thinking about buying a second location and putting in a cafe, which is also awesome.

15:16Fire Nation, again, I love when people are telling stories and giving examples that you hopefully can put yourself in that place and say, how can this apply to my business? How can this improve my life? How can this take down some of my uncertainty? How can this minimize some of my fear? Because both risks and insurance needs are different for startups compared to small businesses that are on their scale journey at this moment right now. So talk about how these are different. These journeys are different and the needs as a result are different, Caitlin. It's interesting when you think about risk management, when you think about the role grit plays, whether it's, again, a startup or someone who's seasoned and is now trying to scale because they're equally hard.

16:02It's hard but different, right? Equal but different. And so as a startup, really grit comes into like fighting through what you don't know. You could be in an industry for 20 years and decide, you know what? I've been doing this long enough. I'm going out on my own. And there's going to be something about that journey that you had no idea that's going to smack you in the head. And you're like, is this worth it? Right? Like, is like what just happened? And so as you think about, again, that startup piece, all of the risk is kind of related to launching. Like it's, you know, probably funding. It's trying to get the idea like out of the nest and into fruition.

16:36It could be marketing. Like, Do you have a set market that you've been working with? Or are you trying to talk to new customers? So all of that is risky. And then whether or not you've invested and what the type of risk is, it's like the insurance piece is different. So for a startup, if you've, again, started a business, let's say my husband's running his business out of the garage, the garage floods. And now all of his wood is ruined. right? For a startup who just spent say$40 ,000 in like, in a bunch of lumber, like that's a huge deal. And if you can't just pull$40 ,000 out of your pocket and replace that inventory, you're done, right?

17:13That's it. And insurance gives you the legroom to say, no, no, like we got you, we can pay for it. And so the insurance risk and needs are just very much associated with giving you the ability to keep going so that you can get to the point of growth and scale, because that's what we want for all of our businesses, right? And then when you get to the point of growth and scale, your problems are probably a little different. Like you're probably profitable if you're thinking about getting a second bookstore. You're probably more established. You have a market. And that grow in scale could mean that you're just trying to like produce more and there's certain things and risks that come along with that.

17:48Or it could mean that you're trying to get into a whole other segment, right? Like, hey, we want to put a twist on this and break into that. And as you start to grow and scale, you're buying new equipment, you're onboarding more people. And if you're not careful and you're not thinking about risk management, there's going to be gaps there. Could you imagine leasing or buying a second building and then overlooking having insurance right before a storm? So that whole scale journey, insurance can, again, make or break that second piece. And I really like to think about, again, risk management, insurance.

18:23It's all the same. There's other things we can do. But risk management plays a huge role in being able to hit that next step. And it only comes in when there is uncertainty, when something has happened that you cannot foresee. Because if you could foresee it, you probably wouldn't put yourself in that situation. So that's how some of the needs shift and where some of the opportunities and some of the blind spots are. Now, building off of this, you believe that a lot of entrepreneurs are not utilizing this insurance that we're talking about properly. Can you share how we can actively fix that? That's a big thing to actively fix on a lot of different sides.

18:59But I do think that there's just enough friction in the insurance shoppings and claims process to make it sometimes easier to avoid than deal with. And I can certainly give an example of that as well. We're working with another client and this business has scaled and grown exponentially. like insanely, so exciting, huge revenues over a million, like fantastic. Their insurance policy has not changed. When they try to contact their broker to get like, Hey, I think things have changed. I probably want to talk to you. Right. Cause they're just a person. They're not in the industry. Their broker's unresponsive.

19:36And this has gone on for years. This has been like three years. So I meet this person. They're like, Oh, you're an insurance. We should talk about this. And it's not a niche that we usually work in. But once I start looking at it, I'm like, Oh my God, A, you're not insured properly, but B, what you were doing is so different three years ago than today that this insurance policy is written for X and you're Y. And so even if a claim does happen, they are not going to cover that because that is what they thought you were doing and what you're actually doing are two different things. And it's really scary.

20:05So that's an example of just enough friction, right? That this person's assuming things are fine and now they've got this huge exposure, which for me, someone who like value security and values managing uncertainty, like I'm stressed out. I'm not even like part of it. And so if I think of how we can work together collectively, I think a having a partner who's giving you what you need, like if you had a partner in your home, who was not fulfilling, like whatever, like needs you have, right, they're either they're not helping you get whatever that looks like, you probably wouldn't want to like, Keep going that direction.

20:40It's the same thing with insurance. If you have a business partner who's not being responsive, they're supposed to be managing the books or whatever, and they're not. You're going to be looking for a different partner or a way out or something. And so I think that part of it goes on making sure you have the right person aligned with what you're doing. And when I say person, it really just means business. You could never talk to this person, but if they've got the resources that's making it really easy for you to update whatever's happening in your life, that's a good partner. So I think that's part of it.

21:10And I think the other side is as business owners, knowing when it's time, like when is it time for me to check into this? When is it time for me to be actively engaged? And so I think we try to offer resources for any partnerships that we do or clients we have to help with that because we know as a small business, you're thinking about growth, you're thinking about scale, you're thinking about, you know, what does that next level look like? Or what is keeping the doors open? You're not thinking, oh, wow, my insurance is renewing. Maybe I should look at that. So I think those are a few things that certainly help on both sides.

21:44And then, you know, as an industry, which is not the conversation for here, I think there's still some opportunity to make sure that as entrepreneurs, as solopreneurs, small businesses are still getting the support they need because it is their business, but we can be better partners than sometimes we are. Fire Nation, a lot of great content has been shared today, just all around this topic of navigating entrepreneurship's unexpected challenges. Again, we can do a lot to prepare for the expected challenges, but how do we navigate the unexpected challenges? Caitlin, if Fire Nation wants to connect with you, wants to learn more from you, what is your call to action for our listeners today?

22:26So if you want to learn more, if you want to hear more, I would certainly say go to coverhound.com slash Fire Nation. We've got a landing page set up for you to provide some information. We've got all kinds of resources for small businesses, all that good stuff. So I would say, please go there and learn more. And you can always contact me as well. Fire Nation, you're the average of the five people you spend the most time with. And you've been hanging out with CS and JLD today. So keep up that heat. For links to everything we talked about, visit eofire.com. Just type Caitlin, C-A-I-T-L-I-N in the search bar.

23:01The show notes page will pop right up. Caitlin, and thank you for sharing your truth, your knowledge, your value with Fire Nation. For that, we salute you and we'll catch you on the flip side. Thanks, guys. Thanks, Fire Nation. Hey, Fire Nation, a huge thank you to our sponsors and Caitlin for sponsoring today's episode and Fire Nation. Successful entrepreneurs accomplish big goals. That's why I created the Freedom Journal to guide you in accomplishing your number one goal in 100 days. And we're talking step by step. Visit thefreedomjournal.com and I'll catch you there or on the flip side. hustle and flowchart hosted by joe fear is brought to you by the hubspot podcast network the audio destination for business professionals join joe as he discusses systems mindset tweaks reframes and strategies to help you build a business that gives you freedom and fuel for your life a recent episode on using ai for effortless content creation is a must listen listen to hustle and flowchart wherever you get your podcasts want to meet me jld in person attend Clay Clark's two-day interactive business workshop and meet me, Tim Tebow, and Clay Clark this June.