Matt Howard, CEO & Co-Founder of EatStreet

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Full transcript from video/podcast below:

Derek: Welcome to Intrepid Insights. Matt, thank you very much for joining us today, I really
appreciate it.

Matt: Thanks.

Derek: To get things started, please tell me a little bit more about yourself and what your
business is all about.

Matt: My name is Matt Howard and I started EatStreet about seven years ago. What we do at Eat Street is we connect diners with local restaurants for online food orders. So you go to, you type in your address, you see all the restaurants that deliver to you, and you can order from those restaurants. Live in Madison today; originally from the Fox Cities area, so just about two hours north of Madison in a small ... very small town of Larson, Wisconsin. But now I'm in Madison today and love it.

Derek: Awesome, thank you. So looking back at the earlier stages of your business journey, what do you wish you could have known then, seven, six, five years ago that you now know?

Matt: In the early days of starting the company, I guess I didn't realize all the resources that are out there that are available to start and grow companies. In the very early days, it was all three of ... Myself and my two co-founders just doing everything ourselves. And I think we ... What I know today is that there's a lot out resources that you can use, whether it's legal advice ... There's free services out there that you can use, there's local conferences that you can go to, there's fellow entrepreneurs who are willing to help you as you think about growing and starting your business. So I think I would have used the Madison community a little bit more to help grow and really start Eat Street in the early days.

Derek: Right on, okay.  Matt, talk more about your business. You started EatStreet for a reason, and my guess was there was a problem you saw and you wanted to solve it. Why was it important to solve that problem for you and for your customers?

Matt: Looking at the industry seven years ago, a lot of restaurants didn't really have access to offer ordering capabilities to their diners, so a lot of restaurants didn't really have the resources or the wherewithal to be able to offer ordering capabilities, so I think it was really important for us ... And it's even more important in the smaller cities that we are really focused on, because we are focused on the medium sized cities like Madison to really help restaurants offer those capabilities. Ultimately, diners, especially in a city like Madison where you have a lot of college students and young professionals, they want to order from restaurants by not picking up the phone to call. They want an app that they can download and be able to order directly from them. But the restaurants just didn't really have the resources to offer that. Helping both the diners connect with the restaurants and really helping the restaurants connect with the diners was really important to us.

Derek: Sure. So EatStreet really has two customers at the end of the day.

Matt: It definitely does, yeah. It's not just the restaurants, it's not just the diners, it's both. We have to serve both of our customers and make sure that they're both happy.

Derek: Right on, okay. So now that your business has had some growth over the last seven years, and I don't know if we can say hockey stick yet, but you're going up, right? How has that impacted your family life?

Matt: It's definitely been challenging as the business has grown because I ... Originally I thought that I would have more time because I would hire more people and they would help me grow the business. But, realistically, the bigger the company has got, the more demanding it's gotten. So making sure I balance my work and family life ... My wife, Laura, my son, Jack, they want to make sure that I'm at home every so often to spend some time with them. Jack is only 15 months old, so he's growing really fast. So making sure I'm spending time with him is really important to me and my family. I think it's something that ... I want to make sure I find the right balance between work and family life because it's something that's important to me.

Derek: Sure. And there's no book written on how to do it, is there?

Matt: There is not, unfortunately. Some weeks are harder than others, when the business is ... Really needs me that week, it's hard to balance family life. But when the business is going well and there's not a fire to put out, I need to make sure I'm at home spending time with the family.

Derek: Definitely. Thank you, Matt.

Matt: When you look at these relationships that I've built, it's also really important because these are not just business relationships, these are personal relationships as well. These people have really helped me grow Eat Street to where it is today. In the future, whatever I do, like I said, I want to be here in Madison. Whatever I do in Madison, I know I can call on these people, because I trust them, they trust me, we've developed this personal relationship that I know that they're going to have my back if I ever want to start something else in the future. And I think that's really important forme on a personal level, to know that I have that backing and I have that trust with key people in the city that can help me.

I've always told myself as the business would grow I'd have more time to myself. I think that is the furthest from the truth. As your business grows, it even gets more demanding and you're ... You even have less time to spend at home. So I think it's been really hard to make sure to balance that family life with the business life. As it's continued to grow... I've been having to focus on that a little bit more and making sure that I have the right balance between the two.

Derek: That's terribly important. As a father, now, too, right? You understand that on a whole new level.

Matt: It's only more important once you're growing your family and have children, for sure.

Derek: Matt, your situation is unique. Your business has had a lot of growth over the last couple years. In the press, we tend to only hear about the successes of the business; maybe it's another raise, the successes of the founders. Tell me about one of the dark days that you've had over the last seven years that people may not know about and what did you learn from it?

Matt: There's always challenges that could come with growing a startup. I know we only talk about the great things, but as a founder and a CEO of a company, I think a lot of founders and CEOs can really call on my issue which is ... Was, in the early days, raising capital. Our first ... Our seed investment after we ... We were through the generator program was very challenging to raise. Back then, now it's five years ago, raising$500,000 in the state of Wisconsin was a little bit more challenging than it is today. Convincing those investors ... Because we were really early back then, and the company was just getting going, we were just getting traction in a couple markets ... We reallyhad to get investors to believe in what we were doing. And that's really hard to do when you're 22 years old; I don't really have a track record, this is the only job I've had after college. To convince investors to believe in me and what I was building and my vision... It was really challenging. And raising that $500,000 was definitely the hardest thing I had done at EatStreet.  I keep telling myself that newer things are harder, but back then it was definitely a very big challenge to get that $500,000 raised and to get investors to really believed in me and my vision.

Derek: Were you 22 when you did that?

Matt: Yes, yep.

Derek: So you just graduated and they're looking at this kid who's got this really awesome idea and you're trying to get money.

Matt: That's exactly it. Again, I had just graduated college, so I didn't really have the real world experience that a lot of people say. It was just growing EatStreet. It just took a little ... Investors a little bit longer to get comfort around the idea that we were on to something.

Derek: Sure. Interesting. Starting, building, and even selling a business brings us challenges, especially financial challenges, both on a business level and a personal level. What was a catalyst for you to start actually considering your personal financial situation?

Matt: Up until about 18 months ago, I had never really thought about ... Thinking about my personal situation. It was always about the business, it was always focused on the business finances and what was going to get the business to the next level.  Recently, I've started to think about myself personally, and the catalyst was my son being born. It's kind of cliché to say, but it's not just you and your wife anymore, there's more people relying on you. It really made me start thinking about myself personally and what our future was.

Derek: Having a family changes a lot of things.

Matt: It definitely does.

Derek: What insights would you say now, being a dad, and starting to look at things on a more personal level, what insights would you have for other founders? What they should be thinking about maybe earlier on.

Matt: It's two things. One, you've got to make the time, first of all. If you don't take the time, you can always make the excuse of, "Oh, the business needs my attention today", and that was something I did years longer than I probably should have. I think number one is you got to make the time to think about your personal finances.Number two, I would say, is ... I think as founders, you get ... You kind of push things off because you're so focused on today and the business, and you don't really think, "Oh, my future is my business; I can focus on my future later when the business is
successful."  Things like focusing on retirement. You don't really think that thinking about retirement today and especially, you know, I'm 28 years old, thinking about retirement is probably not something that comes to mind first, but I do think you need to take the time to think about those things. A lot of people who are 28 working in the corporate world are focusing on those things and are stating to think about those things. As a founder of a company and an entrepreneur, you need to do the same as well.

Derek: That's a really good point, to take yourself out of the founder position for a minute and think if you were an employee of your company instead. What are they actually thinking about and dealing with their lives? That's a really good insight. What resources on a personal level, for your own personal planning, did you find of value that you wouldmaybe suggest others take a look at or that you just found really helpful when you were actually going through your planning?

Matt: I think for me ... For myself and my wife, the core focus when we were starting to think of our financial planning was finding a financial planner that we could really trust and really shared our values and understood what we were trying to accomplish, because we were really new to this. It was not something we had really thought about before.  Because I want to continue on growing the business and my focus wants to focus on her career as well, we wanted to find someone who could really ... We could really trust and know that they would have our back and help build the blocks up of our financial planning.

Derek: I can appreciate that. If you don't trust them, then what else ... Nothing else matters, really.

Matt: As an entrepreneur, you have ... I have enough going on in my daily life that I wanted a help ... Someone to help me on that side.

Derek: Matt, your business is unequivocally a part of who you are. Because of that, the lines between you and your business are easily blurred. How has being a founder of a fast growing business benefited you on a personal level, and have you had any challenges because of it?

Matt: I would say on the personal level, over the last few years, it's been very helpful for me to make contacts in the local community. Whether it's investors that have invested in EatStreet, or maybe investors who hadn't invested in Eat Street, fellow entrepreneurs, successful entrepreneurs ... There's a few entrepreneurs in the area that I call friends today that have really helped guide me. I don't think it's really ... They didn't do it because they were trying to help EatStreet. They were doing it because they were trying to help me on a personal level in growing a business. The contacts I've made throughout the Madison community is something I'm going to keep far beyond being the CEO of EatStreet. I'm going to use that in all of my future endeavors.  On a personal level, I've benefited from those contacts just as much has the company benefited from those contacts. That's a huge benefit for me and my future because I want to be in Madison for the rest of my life, and I think those contacts are important.  I would say on the challenges, there's definitely a lot of challenges. It's, once again, trying to find the balance between family life and business life. I am traveling quite a bit with my schedule, and it's really hard when this week - I'm going to be in three different
cities this week - and it's really hard to make sure you're finding quality family time, especially ... My son is only 15 months old, and every day he changes. And you miss little things when they're growing that fast.  It's a huge challenge; any parent can relate. When they're gone a week from their child, and that's a pretty regular thing for me, because of my schedule. That's definitely the biggest challenge that I have to overcome.

Derek: I can appreciate ... They change so quickly, don't they?

Matt: They do.

Derek: They really grow so fast.

Matt: Every week, it's like, "Wow, you've grown so much." So it's hard to miss out on those things.

Derek: Matt, working as a startup founder of EatStreet means you've taken a lot of risk, probably going to take a lot more risk as the years go. You work a lot of hours, whether you're working on the plane or working at home. What insights do you have for entrepreneurs on how to balance the commitment you've made to EatStreet with that family life that you have; and your personal life, even?

Matt: It's really important. One thing I did was made myself not work on Saturdays. Saturday is my day and my family's day for me to not think about the business and not ... And focus on myself. It's really important for entrepreneurs to do that because it allows you to recharge on top of ... You need to spend time with your family and you want to spend time with your family. You also just need time to recharge and not think about the business or not open your computer. I literally have a rule where I can not open my laptop on Saturdays. That was probably the best thing I ever did for my family life, my mental health, the business health, because it allows me to recharge and rethink and reenergize myself for the business week.  It's little things like that that entrepreneurs have to force themselves to do, and it's really hard. When you're working seven days a week and you live and breathe your business, to take a day off ... A lot of people will listen to this video and say, "It's easier said than done." And I understand. But you definitely need to do it.

Derek: Sounds like by forcing yourself to do that, although it might be difficult, you personally and the business probably benefit more from that disconnect a little bit.

Matt: Completely. It allows me, again, to just recharge and refocus on myself for that day.  When Monday rolls around, I feel more refreshed. I can get more done at the business.  It's going to make me better and it's going to make the business better in the end.

Derek: Matt, it's been great chatting with you today. I really appreciate you joining us. For our viewers, if you could just leave us with one last insight about you, your business, or just what it means to be an entrepreneur that they'll find of interest.

Matt: Yeah. Being an entrepreneur is one of the most rewarding things you can do. You need to understand what you're going to put yourself through in order to do that. It's a lot of work; you're working a lot of hours. It's something that I tell every entrepreneur is you've gotta build a network of people around you to help you, because you can't do it alone. Even if you have a couple founders, it's still important to use, especially in Madison with the entrepreneurship community being so strong, you've got to use the resources around you to make sure you're successful. Because ultimately, it is going to be a lot harder and probably take longer than you think it's going to to start and grow a business. You got to have the network of people to help you.

Derek: I appreciate that ... That sounds like having that network, that team, having those really strong connections makes all the difference.

Matt: Definitely does. And it was definitely crucial to our success over the years.

Derek: Right on. Matt, thanks again for joining us for first edition of Intrepid\id Insights, I really appreciate it.

Matt: Of course.

Derek: To all viewers, please make sure to follow us on social (LinkedIn, Facebook, Twitter) so you don't miss our next episode, and thanks again for watching.

This is for informational purposes only. The ideas, opinions and concepts expressed here should not be construed as specific advice. You should consult your professional business advisors regarding your particular situation. The businesses listed in this article are not meant as an endorsement.

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