MBA1029 Unexpected Speed Bumps in Starting an Online Business with Matt Jenks
2 Feb 2026 · 26 min
Matt Jenks, Program Manager at Weebly, talks about the real obstacles new online business owners hit: driving traffic is harder than expected, but you can validate ideas cheaply by asking your inner circle and going to meetups. Bootstrap first before taking loans, hire interns or virtual assistants early, and stop overthinking it.
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Hey O. Welcome to the 100 RMBA Show. Pumping business, building goodness in your ears every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher, Omar Zenholm. I'm also the co founder of the Hundred Dollar MBA, a complete business training and community online over at 100mba.net and today's episode is a very special episode. It's a bit of a new format we've been trying. We've done this once before. We got some really amazing feedback, so we're giving it another go. In today's guest teacher lesson, I'm going to be sitting down and chatting with an expert and we're going to be discussing unexpected speed bumps in starting an online business. Our guest is Matt Jenks. He's the program manager for customer success over at Weebly. Now, full disclosure, Weebly is a sponsor of our podcast, but they're a highly successful online business. So we reached out to them and said, hey, who can you offer from your team that can help our listeners? Matt has worked with a ton of business builders along the way and he's seen an array of challenges that new online businesses face. So he's perfect for getting to the bottom of today's topic. I guarantee you're gonna get a ton out of our discussion off the mic after our interview. After our chat, I was telling Matt how much value he added to our community with the information you're about to consume. So get ready. We're gonna jump right into the episode now. Just a quick reminder, if you want to get started with your business website with your online store, you can do it easily with Weebly and you could save 15% off. With our special link, go to weebly.com mba to get 15% off your Weebly website or online store. Weebly is more than just about building a beautiful website. It's about building a successful business. So let's jump right into that conversation I had with Matt Jenks. Let's learn how to deal with unexpected speed bumps when building an online business.
All right, I'm super pumped to have Matt Jenks with us today. The program manager for customer success at Weebly. Matt really answers a lot of questions from customers, especially new business builders as they're growing their business as they're facing their challenges. And that's why we really wanted to run today's episode and today's lesson on, you know, dealing with unexpected speed bumps when you're starting that online business. So we're so happy to have you. Matt, welcome to the show.
Yeah, thanks for having me, Omar. Happy to be here.
Great. And I know that you. You've dealt with every single speed bump that you've that's out there when you start a business. So I'm super happy to have you here. And I'm sure a lot of listeners that are going to be listening to this show today are going to be hearing the answers that you're giving to the questions that I'm going to be giving you. The most common questions that people have when they're starting a business. And they'll be like, oh, that's exactly what I'm going through.
Absolutely.
All right, so let's just kick it off.
And I know that this may sound like a very general question, but it's a good place to start. I want to ask you, when it comes to starting a new online business, what is the most common challenge people face? What is the most common challenge that.
You hear from customers?
Yep. Well, I think, you know, we all are familiar with the success stories and believe that, you know, if you build it, they will come. This is not exactly true. It's actually more like if you build it and you market the heck out of it, they will come. Or they might actually come. So I'd say, like, exposure and driving traffic to your site is one of the most common challenges you hear from business owners.
I definitely think you're right on the money. I remember when I started my first businesses online, I think the thing I remember the most is this feeling of, man, I hate being ignored, you know, And I think that's the kind of pain point that most people have. So what's your advice to them, given that's the most common challenge?
Yeah, I think early on, it's really important to try to keep things simple, especially when there's so much to do. You really need to just kind of start the conversation and take a lot of feedback from some of your earliest customers and really start, you know, start off by bringing it to your inner circle, right. Your friends and your family. Let them know what you're working on. Bring it to the people who you think are not afraid to give you criticism, too. So start with your inner circle. Get a couple family and friends involved and just kind of seek some advice from them. And then from there, I'd say, like, start tapping into some communities within your space. You can do this in an online or physical sense if you're doing something online. Obviously, social media has a ton of different communities that are geared towards what your product or your service is really trying to help. Achieve some sort of pain point or goal and then as far as like in the physical sense, like just start getting involved with local meetups. Right. Meetup.com is a really great resource that you can find like minded individuals who are really into the same thing you are. And this is just a natural, organic way to kind of meet people who are into the same thing you are and also tell them about what you're doing and get some feedback from them. And you'll probably get some good feedback from these people because they're not, you know, too worried about hurting your feelings. Like maybe some of your friends or family would. So that's a really important thing. I'd say that's a great starting point.
Yeah, I like what you said about, you know, starting with your friends and family. One of the things I mentioned on the show a whole bunch of times is that if you're starting out and you're talking to your, you know, even just the people in your household about what you're trying to build, if you can't sell them on it, you're definitely not gonna sell strangers. You know, if people that know you, that support you, you know, that will put up with you in the house, you know, they're not gonna, you know, you need to be able to sell those people first. And also you gotta make sure that they're on board. You know, you're sharing a life with them. You want to make sure that they understand that you're trying to do something new and that you need their support.
Absolutely. And just being vocal about it, I think a lot of times people start to get into this place where their insecurities of like, is this going to be successful? Will people judge me? And you really need to throw that aside and just start talking about it because it might be that everyone you know knows one or two other people who might be able to help you achieve your goals. So if you don't vocalize that and get that out there to the world, you'll never have the opportun. So very important to always be talking about it.
Good point. I mean, you were just talking about some of the thoughts that go in entrepreneurial's heads. I'm entrepreneurial heads. I think entrepreneurs, especially new entrepreneurs, have more conversations with themselves than anybody else in the world. And one of the problems with that is that often when you're starting a new business, you overthink things. How do you stop yourself from falling into what's called analysis paralysis?
Yep, absolutely. This is always the case, especially when you're sitting In a room, thinking to yourself, you know, my recommendation there, like I give any client, is to don't be meticulous about the decisions you make and what you try, but rather just being meticulous about what you're documenting and, like, what you've done and what the outcome was for that. I think it's. It's almost as simple as using a simple spreadsheet just to kind of document what you did, what the outcome was, and you kind of just see how things pan out from there. But don't overthink it. Trying something that fails is also a good outcome. You start to learn that way. You learn from your failures as well as your successes. So just start doing things and don't worry about perfection at first.
Love it. Yeah. So, I mean, a lot of us, when we start a business, one of the first things on our mind is like, okay, you know, a lot of people start the business because they need some side income, and therefore they don't have a lot of money on the side to start the business in the first place. So when it comes to funding, like, what's some advice that you can give or maybe you've given in the past when it comes to funding that new business? Should you bootstrap that business? Should you get a loan, get investors? I mean, how much money do you need when you get started? How can somebody find out how much they need?
Yeah, you know, the great thing is we live at a time where there are plenty of resources that are either free or they are like a freemium nature, or pay as you go. And so you can really get up and running with not too much of an initial cost to get started. And so you know my rules. I have two rules, right? Rule number one would be bootstrap for as long as you can. And then rule number two would be, see, rule number one. You know, at a bare minimum, you'll just need. If we're talking about E Commerce specifically, you'll need enough money to establish some inventory and really just to, like, pay for the website's hosting. Whoever you choose to use enough money just to kind of at least satisfy those first orders and be very, very clear with making sure that you're saving everything you can and just kind of grow it incrementally and scale it very slowly. And while you're taking inventory of what customer feedback is like, because the moment you take someone else's money is the moment you start to give up some control of your business. So you really want to avoid this as much as you can. Until there's no other option. And in regards to getting a loan or investor bringing investors into the mix, you'll have to kind of see how it works out for you and how quickly you're looking to scale and the nature of what you're putting those funds to. But some general tips that you might just want to consider would be loans might be a little bit harder to get and might eat up some of your profit, but you still have control over your company. And so for this reason, I would go this route first. If you're strapped for cash and when it comes to investors, there's a lot of people out there who can provide money, but you want to actually be very, very particular with who you choose to take on as an investor. And really, investors should bring more to the table than the money itself, right? Ideally, they should have some experience in your field or have connections that might help you advance your position. Something that kind of gives them a little bit more value than just the funds themselves, because once you do take on their money, they're going to want to have a say in how you spend their money. And so it's really important to know you're taking on a partner who also can bring something to the table as far as helping you with your strategy.
I love what you say here. One of the things I like to kind of remind our listeners is that the whole, you know, these questions about getting loans or investors or, you know, VC funding, all that kind of stuff, these are questions you shouldn't be asking at the start, Especially if you haven't sold anything yet. Like, if you haven't, like, you know, I always do this example, like, if you're selling graphic tees, have you sold 5T shirts to people that you know? Like, if you haven't, like, with no website yet, just like you sold it to them physically at a dinner party, you know, like, if you haven't sold five T shirts yet, then you shouldn't even ask this question because you don't even know if you have a business on your hands yet. You don't even know if you have something that people want yet, you know, and at the same time, you know, an investor is going to ask those questions. You know, somebody who's going to loan you money, someone who's going to invest money. They ask you, like, how many sales do you make? Me? We all have seen Shark Tank at one point, and that's the first question they ask when they're in front of the sharks. Like, hey, how many units have you sold? And if if it's none, they're not looking to invest. You know, they want to look at, they want to back a winner. So I definitely, definitely wouldn't ask any of these questions. I would bootstrap, like you said, as long as possible until, you know, until, until you absolutely need it. And some, sometimes people don't need it.
A lot of people don't realize a.
Lot of great businesses. Spanx was, is a, is a self funded business that's a billion dollar company now, you know, completely owned by the founder. So it's a great story. So yeah, I definitely agree what you're saying when it comes to the money. One of the other concerns a lot of people have, especially when they start out is they see competition out there. You know, they see competition, they get worried because hey, they're already established, they already have their customer base. How am I going to compete with them? You know, should they be worried? I mean, should you be worrying about your competition?
Not in the least bit. In fact, like you should really embrace it for you, your competition. They're actually giving you a little bit of a preview into some of the knowledge base that you can start to acquire. And so, you know, worrying is really like a rocking chair and it gives you something to do, but it really gets you nowhere and you only have so much bandwidth to expend. So don't be worried about the competition, but respect them and really make an effort to learn from them. And by focusing on the competition early, you'll really speed up the learning curve on like your customer discovery. And so some of the things I would say when you're looking at your competition, keep an eye out for some of the following things like price changes, the content and the stories they're producing, the events they're hosting or attending, some of the social networks they're on and the communities they're a part of. And if they start to build or bundle in complementary products and services, these are definitely things you want to take note of because it'll help, you know, like it'll help with the learning curve especially and just kind of understanding like, where are my people, what do they care about, what are they into, what other products and services might be complementary, that maybe I can try to start to, you know, filter my way into that. So it's definitely, you know, the competition is something to respect, but it's also a way for you to learn quicker. So there's some really great tools out there too that can kind of help with that as well. Google Alerts is something that's Wonderful. You're living in email already. Set up Google alerts with your competitors and stay in the know of what they're doing. Social mention is really cool because you can understand what customers are saying. So obviously the formula there is, I want to replicate the good and I want to avoid the bad. Right. So let them be the testing person there.
I love it. I love it. You remind me of a great story. Nicole and I were traveling once, and we were just waiting in the lobby of the hotel, waiting for dinner, and we just chatted with this gentleman who owns three McDonald's franchises, right? I asked him, like, just frankly, hey, like, you know, McDonald's is kind of known and it's this franchise. Aren't you guys, like, kind of a little bit worried about all these gourmet burgers coming out? You know, all these little hipster spots are coming out kind of a little bit more expensive than McDonald's, and people are liking them because they taste so good. And his answer was brilliant. He's just like, at McDonald's, we love anybody who's selling burgers because our competition is marketing for us, you know, so if you have competition out there, they're marketing for. For your actual marketplace, for your actual idea. So if I'm also selling T shirts and my competition is selling T shirts, when they market, they're marketing the idea of you should get a new T shirt. And the same thing goes with this story with this gentleman with McDonald's. They're just happy that people are eating burgers. People eating burgers are gonna eat our burgers at one point. So I was just like, that's a brilliant way to look at it. I really enjoyed that story.
Absolutely. Yeah. Thanks for sharing. That's a really good anecdote.
Yeah.
So you start your business, you know, you're aware of your competition, you know, you're bootstrapping it. You're making it happen. When should you make your first hire? When it comes to your online business, a lot of people, you know, they do everything themselves, and they try to do it all themselves, but at some point, they need help. Yep.
Yeah. There's, you know, you're going to start to see where people come out of the woodwork trying to sell you different services and telling you essentially, like, you're going to fail if you don't have this and that and the other thing. Right. And so not to say that you won't need it at some point, but when we're talking about bootstrapping and it's really early on in the first phase of things, you want to keep it as lean of an operation as possible. And so for me, like my favorite bootstrapping hack, I would say, is to hire an intern. Right. Everyone's got some local community college or university around them, and so, you know, this is a mutually beneficial relationship for you and for the, for the student. Right. They need a resume builder and experience, and you need a helping hand without breaking the bank. So you're going to have so many different daily tasks, completing orders, you know, putting out content and blog posts onto the website. So many different things to do that, you know, your head could spin, quite frankly. So let the intern take on some of those tasks that maintain the business while you focus on tasks that help grow the business.
I love that. I love that. I mean, and a lot of people don't know how, you know, inexpensive it could be to hire somebody overseas or, you know, a virtual assistant. You know, for four or five, $600 a month, you can get somebody full time that can do a lot of admin work. Things that are repetitive, whether they are, you know, updating your website or editing certain emails or even transcribing things like that, that, that you probably do on your own that you really shouldn't be. So pretty inexpensive exchange in terms of how much you pay and how much you get.
Yeah.
I mean, the one thing I was super surprised about when I started my first business online is how hard it is to deal with a bad day. I mean, I remember when you have a job and you go to work, it's so easy. Kind of just like, okay, it's a bad day. I'm just going to go through the motions, check in, check out. Eventually the day is over. I don't really need to be completely switched on. It's completely different when you have your own business. So what do you do when you have those days? You just want to throw in the towel.
This is definitely going to happen to everyone at some point or another. And there's two things that I think are really, really important to always remember when you're having that type of day. The first one, and this should be the leading reason for everything you're doing with this entrepreneurial endeavor, is never forget the why. Why did you start this in the first place? And this is something you really need to think about way before you ever do it. And you hope that, like, your mission is something bigger than just making some money because, you know, you're not going to be making a lot of it in the beginning. And so it can be Very frustrating when the money just doesn't come pouring in. So whenever I'm working with a client, I immediately will start to actually ask them a bunch of questions about this and why are you doing this? And what happens if it doesn't work out? And I do this on purpose because I'm almost testing them in a way where I want them to remember this why and really have it solidified. It's almost like their mission statement. And it's important because the moment I can feel their frustration level rise is where I stop to them and say, like, the reason why I'm doing this is so you and I can both be confident that you're going to fight through the hard times when they inevitably arise, and because they definitely will. So always remember your why and what you're doing this for and why there. And then the next thing is like, you're definitely going to need to have a reset button, right? There's something that hopefully can take five or ten minutes of your time that just says, you know what, Put the work down, put it aside for now. And whether it's going for a walk or a run, reading a letter from a happy customer that wrote to you, Sing one of your favorite songs, play a quick game of FIFA or Sudoku, you know, something that just isn't too, too long because it's hard to get in the zone, but just enough to take a quick reset and, you know, refocus yourself.
Oh, man, you just reminded me of a great YouTube video. You all should check it out when you have a moment that deals with this. And it's a. It's a video by Jim Rohn. And Jim Rohn talks about, you have to have enough reasons to do anything, you know, and you have to have these reasons. And he mentioned some reasons for him. For him, it was one time a Girl Scout came to his door and he couldn't afford to buy the cookies she was offering, you know, and that was just enough reason from, like, I never want to be in that situation again. I want to be able to buy all her cookies and support, you know, this young girl that comes to my door, not feel like such a bum, you know, So I encourage anybody to kind of YouTube that and find that video. So it's like, it's a good one. I want to kind of wrap this up with one really important question, especially when it comes to online businesses. You've seen a lot of people build online businesses. Being the head of customer service and being the program manager of customer success at Weebly, I would Love to know.
Where do people go horribly wrong?
Where do people just realize, oh my gosh, this is not going right, you know, and sometimes they realize too late. So I kind of want to give everybody a heads up.
Yeah, it's, it's one of those where I've seen some really great products never really make it anywhere and most of the time it has to do, especially if we're dealing with E commerce. This is your bread and butter. It's the website look and the layout in general. It goes back to the simple fact that you really only get one chance to make a first impression. And so some of these that you know, aren't very clear as far as like, who are you, what are you doing, why should I care and what do I do next? You really lose that opportunity to make an impression on that visitor. And, you know, we live in a place now where they're just going to go right back to that Google search and go to the next one that hopefully satisfies their needs. So really important to kind of keep it very simple and, you know, less is more. Try not to clutter your elements and focus on one thing at a time there. So images are really important too. We are all visual creatures and you know, a lot of times we're scrolling through things on our phone and the images can tell a lot. So you want to make sure that they're nice and professional. And honestly, I would go back to like one of your other questions, which is like, if I was going to make a first hire or start spending money, I might even end up doing that on my images itself just because they are that important, especially when you're dealing with the website itself.
So yeah, I definitely agree. I remember I had an E commerce store back in the day and I invested in some really good images and in fact, I didn't spend too much because I just went on Craigslist. I found a freelance photographer that was just between gigs and, you know, needed some extra cash and in one day shot a whole bunch of great images for me, edited them within a week and I was good to go for a good year. And it was just a few hundred dollars and it was a great, great investment, I mean, at the time. So I definitely agree with that. I mean, especially if you're in the E commerce space, you know, your images is really what they're basing the purchase on. Like, what am I actually going to buy? What's this going to look like? And if they're high quality, you can, you know, zoom in and zoom out. And you can really see the detail of what the product is. So, yeah, definitely. I agree with that, Matt. This has been incredible. I mean, I think I've. I feel like we've gotten so much out of you. I think our listeners are going to love this episode. And I just want to say thank you for being with us today. You've really added a lot of value.
The pleasure is all mine, Omar. It really is. This is what I love to do. I love talking to entrepreneurs, so I'm blessed to be able to be in a position where I get to speak to them on a daily basis and be able to chat with you. And hopefully some of our listeners have gotten some really good little tidbits here, and hopefully it helps them.
Wow.
So much was covered in that lesson. I want to give a big thank you to Matt and the whole team at Weebly for making this lesson possible. I also want to point out that Weebly really thinks differently. We have a ton of sponsors on the show, and they're all great brands that support the show. But I found it interesting that Weebly were so willing to help our audience with great information and not just a.
Great offer or a great discount.
They deal with customers all day long trying to build that successful business. People just like you and I. So for them to allow us to tap into that knowledge and have their best talent, give us some great information on the show is a testimony to how much they care. If you do want to get started with Weebly and support them and support the show, go to weebly.com mba and you'll get 15% off your Weebly online store or your business website, whatever you decide to do. Again, that's weebly.com MBA. Weebly is built and designed to help you not only have a beautiful website, but have a successful business. I'm a user of Weebly. I love their customer service. So I tip my hat to you, Matt, for running a great team. So check them out and thank me later. Thank you so much for listening to the $100 MBA show. If you love what you hear, let us know in an iTunes rating and review. We read every single one. I like to read them first thing in the morning. It allows us to know what you love about the show and allows other people who check out the show to learn what other people think they learn about your favorite takeaways and why they should subscribe. So thank you in advance for that. Before I go, I want to leave you with this. We talked about a lot of things, but one thing I want to just remind you of. Sometimes we live in our head too much. Sometimes we analyze things over and over. And what I realized over the course of my career as an entrepreneur is that it's actually faster to just do things, try them out, see the result, and even if it's not the best result, if you fail, you'll know which direction to go. After that you'll learn a ton and you'll probably learn it and move on to the thing you have to do faster than if you just thought about it and contemplated oh man what should I do?
And just had that whole analysis paralysis situation.
I learned this concept from Robert Kiyosaki, the author of Rich Dad, Poor Dad. His whole theory in life is fail fast, get your failures out of the way so you can learn which way to go.
Alright, that wraps up today's episode.
Thanks again for listening. I'll check you in tomorrow's episode. Until then, take care.
Of sam.
