May the Best of Your Today's Be the Worst of Your Tomorrow's: Ben McDougal's Insights on Entrepreneurship
00:01
Hello everybody. Thank you for joining me on the Healthy Project Podcast. I'm your host, Corey Dion Lewis. I have my first guest of 2024, a man I've known for a long time. He has a lot behind his name, but what I know Ben for the most is he is a man of coffee and community, a community and coffee, and all things entrepreneurship.
00:26
Ben McDougall, thank you so much for being here, man. I appreciate you. Cory, it's great to be here. I've looked forward to sitting in and sharing some space with you ever since this creative season began. So cheers to all the remarkable evergreen conversations you've hosted and it's a treat to be here. Yes, so, no, so I told this story before but I haven't told it on my platform because it's your first time being here but the first time I connected with you and it was, you probably remember
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after I've already told you before, but it was so, it was so funny. It was my entry into figuring out finding community around entrepreneurship. This was 2010, 2011, and I had a platform, I had an idea called Gamify Wellness. And I wanted to create this game around wellness. And I didn't know what I was doing, but I was trying to find people. This was when LinkedIn was not the LinkedIn that it is now. And we had a bunch of...
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bunch of people connected, I connected with you. And I was like, I think I connected with you because you had something about gaming in your title. That's right. But it had nothing to do with what this was console. Halo Guitar Hero Day. So I'm like, yo, I'm gonna connect with this guy. Maybe I can figure something out. And then I messaged you. And you wrote back and you said, I'll never forget it.
01:50
I don't know how I can help you. I'll meet you for coffee. That's about it. I just came from coffee that had no reason or agenda. Right. And, um, you know, just to jump into the meat, like you ask what gets me up every day. And I think about like the serendipity that awaits us, you know, when you're willing to say yes to adventure, when you have less objectives, um, when you are generous with your time in a way that invites
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some interesting collisions, maybe not knowing why, but knowing that if you say yes, it introduces that opportunity. And so I think I've always enjoyed meeting new people and find it interesting to learn how people spend their time and boy, the amount of understanding that folks who are willing to do such activity, the simple act of showing up requires initiative, but when you do, you are like,
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blessed in ways that you'll never expect. Right. And the more you do it, the more complex it becomes, the wider but also deeper the understanding is as you continue to explore people's passions. No, that's real. And that's part of why I wanted you in today, because I know a lot of people are like, okay, why do you have an entrepreneur on a public health equity podcast? And I was thinking, this has been something that has been on my mind for probably a year.
03:16
And when we're talking about social determinants or social drivers of health, um, income comes into play, social economic status. And I don't believe people think of entrepreneurship as a way of improving their life.
03:33
to get out of their circumstance. So who better than someone who is in the entrepreneur ecosystem, where I'm sure you have spoke with people who are way up here and all in between. Yeah. Right? Yeah. To how do we get people to think of a better way of improving themselves through entrepreneurship? I've started to call it the entrepreneurial lifestyle. And...
04:03
I don't want the word entrepreneurship to feel intimidating. And so when we think about like the creative spirit, when we think about the innovative mindset, that translates fairly well, no matter how you spend your time. And so that might be in an health organization where it's a large group of, you know, the team is a lot of people and being willing to like,
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you know, be the linchpin and build without a roadmap. Having that intrapreneurial spirit will help existing organizations stay ahead of the innovation curve no matter the industry. Then you start to like look at activating people's passion and different types of capital.
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when you're encouraging them to explore areas outside of what they're getting paid to do, knowing that that energy can translate into more action, you know, in their existing role. And then you also have folks who decide to build their own company and maybe turn the side hustle into a full time effort. And over time, maybe there's the stability of financial capital that emerges and they're able to build their own team, right, but stay connected to those that
05:19
opened the doors or created some paths that allowed them to get creative in their own way. I'll jump to a fun paradox. Do you think everyone has a create? I'm sorry, I jumped to my answer. Do you think everyone has an entrepreneurial spirit? I feel like everybody has. Yeah, I do. I don't play everybody knows it. I don't like people
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fearful of that term because they maybe have a different, they think it means something else. Yeah, I have to quit my job and go raise a billion dollars and be in the headlines and have this highly successful story. Right. When
06:05
It sounds weird, but releasing yourself from the constriction of financial capital, finding things you enjoy, looking for tribes you enjoy supporting and community that you like being a part of, like that type of activity will fuel momentum that draws in the types of capital you may want. So using the, you know, maybe it's human capital, maybe it's intellectual capital. Maybe it's institutional capital.
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as ways of attracting more of capital that you don't have. It's like a liberating thing, but it does require extra gears. You know, you have to work when someone else doesn't. And so, you know, it's kind of a joke, but you have to play 80 hours to avoid working 40. Bar.
06:58
And the lady making cakes and selling them on the side is an entrepreneur. 100%. You know, in fact, I wrote about this. The term small business is like an economic category. 99.9% of all businesses are in it. So I'm not sure what the point of categorization is at this point. But one of the things I find interesting is the term connects to maybe the smaller business owner or the main street. Less like...
07:27
scalable tech flavored startup. But when you use such a term to bring folks together, because it, okay, it resonates, this is me, I'm gonna show up. Once they're in these environments, use it if you want, but there are so many better words to describe these individuals. Leaders, heretics, entrepreneurs, founders, you know, there are ways that you can.
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encourage folks to use that creativity, use that innovative mindset, no matter who they're trying to, you know, impact with their business. You talked about different types of capital, and one capital that I'm thinking about is community. Yeah. And using community. Can you talk us a little bit about the importance of community to an entrepreneur, and maybe vice versa? Like, what does that look like? Yeah, yeah. Community is chapter two.
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You know, it comes pretty soon after the idea. Yeah. And I think in our connected era, it allows more people to do what they want to do more with less. Leveraging community allows you to find customers, to do that customer discovery early on. Feedback is data, right? And so knowing that you might have a good idea, but it needs like chiseled.
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in order to find product market fit so that it's not just cool from your family members but cool from people willing to write the checks. Yes, who don't know you. And so showing up in those environments allow you to let those ideas breathe and vice versa allows you to learn from a diverse collection of perspectives that you might not have immediate access to in your existing network. And so.
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The willingness to show up. I know it sounds easy, but it's not. You have to say yes when it feels like no. And then also a willingness to go beyond just what do you do, like getting curious to learn about what other people are doing and maybe releasing the transactional networking and trying to build connectivity over a more lasting experience. And then feeling, kind of completing the circle. After standing out, ask.
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after asking good questions, creating inverse charisma with folks that you're interacting with, almost releasing like the agenda that you have in your mind, but knowing that it will emerge. And then following up and continuing to connect dots, introducing others that art of connection exists so much longer than the moment of maybe an event. Over time, this form of generosity builds trust.
10:17
And as your engaged network expands, it really allows you to caffeinate whatever you care about. Yeah. And you talk about, you talk a lot about patients and in the book and in one of the chapters, but I want to, I want to connect that to the, the networking and building community because I feel like a lot of people when, and correct me if I'm wrong, cause you, this is, you know, you're about that life, but
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when people first start trying to connect and build community and they go to a networking event or to insert whatever event, they go up to a person, yes, I sell this, buy, here's my card. And it, to me, guilty. I've been there, but it kind of ruins that connection. How can somebody...
11:07
What is the first thing somebody should do or can do to build, to start to build their community or even find a community that will be supportive and understand. Yeah. I mean, uh, showing up and having a variety of conversation starters that aren't, what do you do? There are so many more interesting ways of, uh, getting deeper, faster. Yeah. Um, and so, you know, how do you spend your time? Uh, where are you from?
11:35
There's a variety. Would you do this if you weren't getting paid? There's a million different little ways to captivate a more interesting conversation. But I also think that there's probably value in thinking about the reality that this first degree of interaction probably doesn't get you the value that you look for.
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And so trying to drive home like, you know, a sale right in the transactional moment is so uncommon. And the amount of people you'll turn off is much higher than the one person that it might resonate with. And so thinking about, oh, I mean, let's use LinkedIn as an example, thinking about the second degree, the third degree of connectivity when you're talking to someone almost releases the required, Hey, I need to make sure to deliver my action.
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right here, right now. And in the connected area, you're gonna follow up. You know, you're able to find them online. Hopefully you'll see them at the next gathering. Or find, you know, different folks that start to connect dots along the way. And so more of a sequenced mindset will help folks, I know it's helped me, just release the urgency. Yeah, that's where I was trying to connect it with patience because it's...
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feels like for some people, and I've had some of these experiences where they're so, they're so fearful of not getting that next connection or not that next sale that they missed the connection. And maybe, maybe it's been too long. And so now you are in kind of an urgent position, right? You're trying to make that next sale to.
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ensure this company can survive. And so I, you know, recognize that there's, of course, valuable urgency as you're building companies. But balancing that, balancing that, and knowing that when you give first, when you accelerate others, that trust that's built allows more, I think interest in others helping
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to connect dots for you. I mean, it's not uncommon for me to ask so many questions that people are just like, so stop. What do you do? And then I'm like, it's a secret. Yeah. But having that much interest in active listening, it's interesting how loud listening can be.
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absolute how loud listening can be. I love that. Talk about when you first started your entrepreneurial journey and how maybe how hard it was to get into it, how easy it was compared to now that we are so connected. There are a lot more platforms and software that people can utilize for free.
14:40
You mean like what's the difference between now and somewhat then and someone trying to start their entrepreneurial journey now? So I'm part of the NES generation, right? This group that grew up before the Internet, but was at an interesting time when it arrived and was able to leverage technology and now see the world post Internet. Right. And so I think the biggest difference is that.
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You know, we are all weird and being able to connect the most like viable audience is much smaller than trying to build a global brand or a national brand using a single medium of one TV or radio channel that used to exist back in the day. Right. And so I also think that is liberating because it means that if you can find a thousand true fans, you can have a sustainable business.
15:40
You might not be buying islands, but it might be an interesting compliment to other activities that also might have some financial stabilizations. And now you're able to explore areas that you're passionate about. Um, and, and I like to use the word diversified career portfolio. Um, there are more people doing more things without diluting themselves to mediocrity.
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And so keeping your eye on personal bandwidth as you say yes to something while saying no to other things. Right. Being quick to say yes, but also a no is better than a long wrong yes. And so having kind of that experimentation, a willingness to explore a new creative season, right? Versus feeling the weight of a new venture, a new company, a new project. Like, I'm just going to say yes to this. Here are some milestones that I can personally
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if this is a good use of my time, and almost being willing to lead in a way that this might not work. Those are some of the capabilities that we now have that might not been as available in the industrial age. And so I just think entrepreneurship, exploring your side hustle, being an intrapreneur, perpetual learning is so much more available in our modern times that
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I would go as far as saying I feel bad for people that don't explore some form of entrepreneurial venture. Yeah. I want to, I want to get to, um, some, some selfishness. I talked about this before. Well, I like, I like how curved up those pages are, my friend. You showed me some of the highlights. So first and foremost, thank you for spending some time with me. Yeah. So you don't need this book. Before I, I kind of talk about.
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some of the things I want to talk about, because they do resonate with me, but I think they will resonate with that person who's like, I'm not happy with where I'm at. I'm not sad with where I'm at, but I want to start something else. And that's kind of how it started with me. I had this energy for wanting to build, and I found it, and I would do this for free forever if I could, but I'm blessed to be able to, you know, make a little bit of change off of it as a side hustle. But there are a lot of people that are
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afraid of the side hustle, whatever the case, whatever it is. But I really want to talk about some of this side hustle stuff, man, because I need more. I need more in depth answers. And I come on my two hundred and two pages wasn't enough. Dude, I've been a side hustler most of my career, but I didn't know it was called that. Right. When I grew up, we were getting expensive pieces of paper to build someone else's dream.
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Entrepreneurship was not a word startup wasn't a word like it wasn't nourished in the way education invites students to explore it right now. And so I love that I'm envious of students that are coming up these days. But it was it was a way of like, accessing the side doors of areas I was curious about, but might not have had the bandwidth capability or understanding to go full time.
19:02
My example was I went and got a computer science degree to build video games. I went to California, looked at what it was going to be. If everyone's seen Grandma's Boy, that would have been me, like bottom of the totem pole, like four jobs in an expensive environment. Came back and fell into internet development instead. But I didn't realize that you could build something and activate.
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the area that you were so passionate about was something that you crafted on your own through community, in fact. Yeah. Right? So we built a social network back when MySpace was cool for video game enthusiasts. And so it invited people to have profiles, to share their favorite games, to connect through what they cared about. And we also activated the live event.
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experience. So eSports before it was eSports. I was playing Guitar Hero in Times Square with Blackberry down in Disney World going to E3, you know. And so this is an example of how a side hustle unlocked just untold adventure and was not like the most obvious way of pursuing my career, but really continued to explore side hustles.
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And now you've got Flightbright, which is craft beer technology. We built a electronic beer flight paddle that has a touch screen. Yeah, has nothing to do with the platform. I love the logo. The logo is just dope. The logo is sweet. Yeah. And yeah, the logo, that's the whole story. But everyone wanted to make it beer, beer, beer, because our first like embodiment was for craft beer.
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But the electronic serving system that we have in place was built both from a team perspective, from a branding perspective, and even from a legal and IP perspective to transcend beer into cheese, into wine, into all these different types of experiences, where as a consumer, that plate of sushi arrives, which one is which? This is the question that we can answer.
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with technology and it allows consumers to enjoy it now, but also enjoy it later in different environments. And for a taproom that's serving craft beer, how much more valuable is someone knowing the name of that beer at the grocery store or at the other brewery or at the different environments than like number four on a washed up piece of paper. Right.
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So that was an interesting path that we pursued now We have a craft or a beer festival app as well and flightbright is another side hustle that has like a Full story connected to it Wow And so I think the side hustle chapter means a lot to me Because it's the way that I think I was most hands-on introduced to entrepreneurship Yes, so there's there's a part in here where you say winners quit all the time. They just quit
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the right things at the right time. 100%. Quitting is a good thing. The cousin that most people would put to quitting is failure, but it's not. You either learn or succeed. And if you're able to find things that are lasting proper yeses, then great. But as I mentioned earlier, a quick proper no.
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is so much more valuable than a long protracted, incorrect yes. And community, customer discovery, those types of collisions help you get out of your own bubble and recognize that this might be a no or might be a pivot. It might just need to evolve. Usually, the original idea is not the one that captures product market fit.
22:55
Yeah, and I feel like with community, they can tell you in a way, if you, if you foster the, uh, safe and positive community, they can tell you, no, in a way that's not going to make you feel any type of way. You may feel butthurt about it because it's your baby's ugly, but they can say your baby is not pretty.
23:16
Right, right. And being conscious of that as you're providing that feedback, right? Yeah. Appreciate the initiative. Here's some feedback from my experiential wisdom and remembering that feedback is data. So one person's perspective, that feedback is valuable, but it should be taken with a grain of salt. The more feedback you collect, the better decision making you will have. Do you feel like people stop?
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before they need to because they didn't get enough feedback. 100%. Maybe they asked one person. They said, oh, I don't like it. And then they said, OK, never mind. Oh, and in contrast, someone says, great idea, perfect. I'm going to build it. That's all I needed, just one more person. Just one more person. Yeah. I mean, I would suggest the customer discovery is ongoing. And so being willing to invite those collisions and also sharing those back with folks.
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who are just as passionate about what they're building as you are with yours. Um, I think that's another huge value when you think about interacting with community and honestly, customer discovery is the work. Um, and it always is, it just, there's other things that emerge as the journey continues. Right, right. So there's another one here I want to talk about really quickly. And it's about patients.
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And you said the luxury of not needing to make money can lead to crippling procrastination. Indeed. Woo. Yeah. It's, it's, it's bar. I wish I had sound effects right now. It is a privilege, um, to be in such a state where you're exploring commercialization of an idea. Um, and it might not need to work in order for you to feed your family. Um,
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That is something that I've appreciated in working alongside of my co-founders with Flightbright. We'll stick with that example. It was a hobby that paid. We continued to build it. When we got together, this was fun for me, you know, playing pinball and talking about a business along the way. And so I'm thankful for that. But it also like doesn't have to work.
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And so we can just wait till next week. We can just not do that until it gets done. And so it is very easy to slip into a very procrastinated culture. And once that really goes that far, it's hard to activate urgency again. And so one way to ensure that if you're working on a team
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getting that elephant in the room and talking about, okay, we're eager now. What happens if one of us feels a little less interested in building on the timeline of now, you know? Right. And that will happen. And so knowing that you need to have flexibility, this is not a race, it's a dance, but people are gonna dance at a different pace, even when it might've started in sync.
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Um, and, and having transparency is a good way of maintaining culture and maintaining a team vibe that will evolve, but can evolve even if people go different directions.
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still in a similar direction. Right. What about that solo entrepreneur that? Lone wolves can do a lot. Yeah, that's doing the side hustle, same scenario, doesn't need it, but they don't have the other person to bounce off of. It's just them. What is something for someone like that to stay focused in it and engaged as much as possible? Yeah, I mean, you have to be all of the superpowers instead of potentially having to be
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having the exponential capabilities of more superpowers in the team. And so that said, you can get a long ways as a lone wolf, if you're willing to turn more gears and continue the initiative of showing up, activating and leveraging community. And I've
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done it in a variety of different creative seasons. And I celebrate the lone wolf. I think side hustles and lone wolves are common. And it's interesting because most folks who explore a side hustle or maybe pursuing a lone wolf kind of environment are envious of those who have burnt the ship and are gone all in or are building a team or raised a co billion dollars or sitting in the headline.
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This creates a sense of envy for folks. But know that other folks are envious of your flexibility, your nimble nature. Maybe you have stability of a full-time job alongside of it. Must be nice to have health insurance. Exactly. So don't get lost by the headline trap. And being patient, knowing you'll have to do more,
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And maybe thinking honestly about what you're good at, but maybe what you're not. And as you're in the community environments, creating connection, maybe there's someone else who could be doing something very different. But you groove, you have good times. The type of mindsets are shared, but also not cloned. Maybe that co-founder emerges. Maybe that new team member emerges over time.
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versus maybe the rushing into a bad idea because I think I need to have a second person or that third person in order to feel a sense of legitimacy. Right, what do you feel, thank you for that, because that was great. There's so many more highlights by Matt.
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be mindful of your time. Whatever. This is three hours. But I want to know more. And you probably answered this question for me before, but I want to know more about your, your connection to this book. What was it about this book that made you say, I have to write this, the potential regret of not synthesizing. Um,
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my understanding as from like my own experiences, but perhaps more importantly, what I've learned from others. I've been having coffee at 1 million cups every Wednesday for over 10 years. As an entrepreneur, I've been active in all the other, you know, ecosystem activities for so long. And with my current position inside the Kauffman Foundation, as the regional
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I'm helping to support teams of organizers in rural, medium, and large entrepreneurial ecosystems across the country. That type of like cosmic mosaic of collision is what gives me a lot of confidence in the fact that A, the entrepreneurial lifestyle is never A to Z.
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and is never the same for anyone. But there are some frameworks, there are some different things that are important along the way. And being able to pack that in for first time founders while creating enough wisdom and depth for maybe more of a veteran entrepreneur, I knew I could do it. And I was thankful that I was able to release that potential regret.
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by synthesizing this, even if it was just for my little startup that pays in love. Mmm, pays in love. I love it. For somebody that is listening, that wants to, they like, hey, I'm ready Ben. I got the idea. Let's go. I got the passion. Yeah. Where do I start? Who do I talk to? What should be their first step, their next step?
31:52
Let me take a look at the table of contents. Because it says. So chapter one is ideation and learning how to listen, training your brain, exploring the opportunities that we all have to think about creative things, solving problems, and looking at the world in a positive some way.
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Then communities, so we've already talked a lot about that. Getting into the mix, doing some research. This is an interesting shift. Don't hope it doesn't exist. Talk about that. What do you mean? Try to find it. Yeah, OK. Yeah. Try to find it. Try to find the name that you've fallen in love with too soon. Yeah. You know? You're just avoiding future complications, if you can be honest earlier.
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And that's not an uncommon misstep. And so look for view the competitive landscape, appreciate what's there. Think about wrinkles that would separate you and like start turning knobs, right? No one cares about your great idea. They care about how you execute. People wanna see your idea in reality.
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And the more signals of traction, it doesn't even need to be paying customers. The more signals of traction, the more momentum you will captivate, which will fuel the next knob that needs to be turned. And maybe that's a co-founder, maybe it's that website, maybe it's that next marketing twist that you need to build. And so there's endless things that you can continue to build toward a direction with.
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but being honest with your capabilities and not trying to boil the ocean when it's hard to warm up a cup of coffee. Yes. Hey, I'm, I'm going to, I'm going to drop the mic there for anybody listening that wants to learn more about you and get to know you a little bit more. Where can they find you? Thanks, Corey. I knew this would go fast.
34:06
After we cut the mics, we'll probably be here for another four and a half hours. So I'm super easy to find. I can't wait to learn what your listeners are building. I am with you. People are like, who are you with? You. It's an interesting state when the way that I spend my time is accelerating others, often through the art of connection, but in different ways of investing in your success. And so.
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That's an open invitation for friends who are listening and are interested in ways that they can continue to pursue their innovative ideas in an existing company as a side hustle, as a student, or as a full-time founder. BenMcDougal.com, it'll be in the show notes, I'm sure. That has links to me. I live all throughout the internet and I just can't wait to see what this conversation does for folks who are exploring what's next in their lives.
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And I guess I'll wrap it with the way that I sign all my books and even say good night to the little one. May the best of your today's be the worst of your tomorrow's. That's it. Ben, appreciate you. Keep building. Yes. Thank you, everybody. Thank you for listening to the Healthy Project podcast.