Jennifer Stewart, Gateway Productivity

00:00:55] Sanjay Parekh: Today's guest is Jennifer Stewart. Jennifer founded her company Gateway Productivity in 2016 to help clients better understand digital solutions through teaching, training, and organizing. Jennifer is based in St. Louis, Missouri. Jennifer, welcome to the show.

[00:01:11] Jennifer Stewart: Thanks Sanjay.

[00:01:13] Sanjay Parekh: So, I'm excited to have you here because I have lots of opinions on the things that you do and they're all good. But before we start talking about what you do as a company, tell us kind of your background and what got you to where we are now. 

[00:01:26] Jennifer Stewart: Sure. I'll start with a little bit of nuggets about me. So, I'm a musician and I play the flute and I sing. And so, I went into entertainment management in college, but as many of us do, I did not continue. And I had one job in that and then figured out it wasn't the right thing for me. So, I moved into the financial management world and was in client service there and I did that for about seven years, and it was getting more and more corporate and so, from there it just, it wasn't feeling right to me. I felt like I was not making a difference in anybody's lives. And so, I decided at that point to start my own business. So, that’s a little bit about that background and why I went into business. 

[00:02:17] Sanjay Parekh: I can't believe you didn't stick with the flute because you could have been Lizzo. Look at where she's gotten with the flute.

[00:02:26] Jennifer Stewart: Yeah. No, I actually I wasn't in performance I was the realistic person who had to put music with business. So, entertainment management because I knew I did not want to go into it, but good for her. 

[00:02:40] Sanjay Parekh: Okay. Tell me a little bit about Gateway Productivity and why you decided to launch this. 

[00:02:47] Jennifer Stewart: Sure. So, Gateway Productivity is actually the second company that I had, and the first one was along the same lines. I actually started when I left that financial firm, I started a home organizing company, and within probably about six months, I figured out that was not quite the right fit, which, you started company, you got an LLC, you've got the whole deal. And I was like, oh, no, what am I doing? And so, I worked with a marketing coach and that was so helpful. And the marketing coach walked us through, you know, you can't sell what you don't love. And so, that was where we started. And I was like I don't quite love what I'm doing. So, he had us go through, what were all of our previous jobs? And what did we love doing in those jobs? 

I always loved training people on computers, and it was never in my job description. So, then fast forward a little bit and I was like, okay technology organizing, I could do technology organizing and training. And so, that's what I was with that first company.

And I actually had a colleague that's also in the organizing world. She sent me my first client and I just loved it. And I knew that was what I wanted to do from then on. So that was 2012. And then in 2015, I closed that company to open Gateway Productivity. It was originally Gateway Organizers because we were doing business organizing and there were three of us, there were two partners and myself.

And what we had decided is we were all headed in that business organizing direction. One was doing things with startups. One was doing business organizing, physical in the office. And then I was doing more of the digital or technology organizing, if you will. And so, from there, it went into different iterations. Gateway Organizing then became one less partner when one decided it wasn't for them and they wanted to do home organizing again. And then in, let's see, I guess that was 2019, switched the name Gateway Productivity. So, it was really starting to sound more like a business company or a company that works with businesses. And in 2020 is when I lost my second partner. We knew this was coming. They were headed in the direction of ADHD coaching, which didn't really fit again with that business organizing or business productivity world. They split off in 2020 and I became a one woman show again. And I was so scared of it, I have to tell you, but it turned out so well. I again worked with a different marketing coach at that time. Marketing coaches have just been my world. I've worked with several of them. And so, in 2020, I worked with one, went through an entire class on branding, rebranded in 2021. And I have stayed that ever since. And I just love it. It's who I am. 

[00:05:55] Sanjay Parekh: Yeah. Yeah, I've now realized like okay with the flute you could have been Lizzo and then with the home organizing you could have had a show on Netflix but you've gone deep on this, which I love by the way. I said this at the top, because I’ve got kids now. I used to be the tech support for everybody in the family, so my parents, my in-laws, extended family, everybody, but man, once you have kids, they become the first tier tech support and my responsibilities have gone down so much. So, I very much appreciate people like you that teach people how to do tech. Because it means people like me have to do a lot less work and be less free IT support for those folks out there. So, thank you very much for doing that. 

[00:06:38] Jennifer Stewart: Exactly. And that's a lot of my clients, honestly, because either their kids have grown up and they're out of the house. And so, they don't have that live-in tech support or their kids are like, no, I'm done, mom. Get somebody else to help.

[00:06:55] Sanjay Parekh: Yeah. So, you mentioned there that you were scared when you lost both of your partners to do this on your own. What was it that was making you nervous about being a one woman show? 

[00:07:07] Jennifer Stewart: So, being honest, my first company, when I closed it in 2015, it was probably headed to be closed anyway. My accountant came to me and she said if you're not showing more of a profit within the next year or two, you're going to have to close your company. And so, my head went straight to failure, failure, failure. Haven't done well in my company. And then all of a sudden, poof, two partners came out of nowhere, closed the company that was quote unquote a failure, and then moved on to this new partnership. 

And so, what my brain went immediately to in 2020, besides COVID, was, oh, you're going to go back to being that one-woman business failure person. And luckily my business partner that was leaving, as I said, is a coach. And so, they spent the time to do a little coaching for me. And around how I had grown and gotten more successful and learned so many lessons and all this stuff. And so, I had a lot of support from a lot of different people that helped me get over that fear and really the fear of going back to being a failure. And when I took that class and rebranded, it’s only gone up since then. So, whatever everybody did for me, worked.

[00:08:34] Sanjay Parekh: So, the previous company, was that the first time you'd done anything entrepreneurial or had there been things when you were a kid? Hustling things or anything else like that? No? 

[00:08:44] Jennifer Stewart: No. I'm definitely not that saleswoman. My uncle did that from the stories I heard. He would sell used roller skates and all the other stuff. So yeah, so he had an entrepreneurial spirit. I actually had it from all sides. It was wonderful because my grandfathers, both of them, had their own companies. And then my mom had a business partner and ran her own picture framing company. 

[00:09:14] Sanjay Parekh: Did you work in any of these businesses, the family businesses?

[00:09:19] Jennifer Stewart: I did work for my mom. I was the help that cleaned things and stuff like that. I never sold anything or anything like that because they were very much like a in-person, talk to the client kind of situation, so I wasn't ever involved in any of that. But yeah, oh yeah, I did the cleaning, and I was doing that probably, oh, good grief. Probably when I was eight, 10, something like that. 

[00:09:45] Sanjay Parekh: Sounds about right. Like families do that on the farm when you're old enough to get out in the field, you do that. Same thing happens here when you're old enough to start helping out in the family business, you do it. Okay. So, the current business that you had when you started with the two partners. How did that all come about? Were these people that you knew, or did you approach them? Did they approach you? How did that all happen? 

[00:10:08] Jennifer Stewart: Great question. So, I have been a part of the, and it's going to be a big mouthful. Bear with me. National Association of Productivity and Organizing Professionals. It is NAPO for short for everybody who knows it. And I've been a part of that ever since I started my very first, even before I started my first business. And so, I've been in community with all of these colleagues that do similar things to me. And so, it was two of those colleagues that came to me and at the time they said, Oh we're both trying to focus on business. Maybe we should all three go into together and really focus specifically on all the different aspects of business. It really came up, now that I think about it, I'm glad you asked that. I hadn't thought about this this conversation. One of them was talking to me about I keep trying to refer clients to you and they never pull the trigger and go work with you. And I said the same thing's happening to me. I'm trying to refer them to you, and they won't ever go work with you. So, we were like why don't we become our own company? And then we just immediately move them into business into working with the other person because we have each other's calendars and it's a real smooth transition. 

[00:11:27] Sanjay Parekh: Yeah. Did, is that what ended up playing out? So, when you were together, then did clients actually move better?

[00:11:34] Jennifer Stewart: Absolutely. The first partner that broke off, not as much. She was in a completely different space doing work with startups and things like that. So, it was a little different from what the other two of us were doing, but yes, the two of us that originally had that conversation, yes, we were passing people back and forth smoothly. Not every client fit that mold, but a lot of them did.

[00:11:58] Sanjay Parekh: But it's interesting that was the friction point that caused them to drop off and just by solving that one little thing, because that's not the thing that you would expect, right? You would expect that it's the cost of the service or something like that. It's just the scheduling piece or the handoff piece that was the problem. That's so interesting. 

[00:12:18] Jennifer Stewart: Yeah. I will tell you, though, with that person was focusing on business coaching and business organizing, and typically people are in a place where it gets really bad in one realm or another. And so, they'll focus on, okay, my office is a mess, this is something I can visually see, and this is driving me crazy. So, they'll take care of that. But when it comes to the technology, often, I will get the people that are at the point where they're losing emails, things like that, but it doesn't usually flow quite as seamlessly as you would think. Because once they've taken care of the thing that's visual, they may not want to continue working on the technology because they can deal with the technology. Or if they're really having a hard time with the technology, they don't want to deal with the office once they've now taken care of the technology. But we were able to then have those conversations with them. We have another partner that does this and then why it made sense for them specifically.

[00:13:24] Sanjay Parekh: Yeah. Interesting. Okay. Let me ask you a question about this tail end of it. When you ended up basically having to unwind the thing that got you started, how did that go? And how did you manage that process? Were the three of you equal owners? Did you buy them out? Like, how did you manage to do this in a way that made sense for all parties?

[00:13:48] Jennifer Stewart: Yeah. So, when the first partner left, which was about a year and a half after we had started the company that partner wanted to go do her own thing in home organizing again. So, that one didn't go quite as smoothly. I won't go into all the details, but it wasn't quite as smooth. She wanted a little more than we were trying to give her – her client list and all of these different things to make it just real seamless and easy. And she wanted a little bit more than that. And so, we had to work all that out. We did have a lawyer involved in all of that and made sure that everybody at the very end was happy with what it was. And then she went off and she has a very successful company now. And so, very happy for her in that. 

And then when my second partner left, I knew that one was coming because, since they were moving in the direction of ADHD coaching, then it was just, we knew that it was coming at some point. But then some personal things happened, and so we had to cut it off quite a bit earlier than expected, probably five or six months earlier than expected. And so, with that one, that was super easy because we're still the best of friends and we didn't even have to get any lawyers involved – just for the paperwork, really. Because both of us were like, oh, I think you should have this. And the other person's like, oh no, you keep it and that kind of stuff. And that worked out really well. It just ended up they got what they put into the company back, of course they kept all their clients because they didn't make sense for me. And yeah, everybody, we were all very happy at the end of that as well. And I still support everything that they do. And they, again, they also started their own company, have a very successful company and podcast. 

[00:15:49] Sanjay Parekh: Yeah. So, that's interesting. You've been kind of on both ends of the relationship breakup type of thing, right? One went really smooth, and one went less smooth, a little bit more rough. Do you feel like the one that went smooth, because it went second it was smoother because you both experienced the roughness of the first time? 

[00:16:11] Jennifer Stewart: Possibly, and I think we were just more in tune with each other. As I said, we're still very good friends. I'm an acquaintance with the other person, but we're not very close. But I've always been friends with the second person. Yeah, so I think that was more than anything, but yes, we saw what went wrong the first time, and absolutely, we were both on the same page about it. We were both mad about the same things, and so it didn't go that way when we split. 

[00:16:40] Adam Walker: Support for this podcast comes from Hiscox, committed to helping small businesses protect their dreams since 1901. Quotes and information on customized insurance for specific risks are available at Hiscox.com. Hiscox, the business insurance experts.

[00:17:01] Sanjay Parekh: Okay, let's talk about health and wellness and stress. You've now been through the whole gamut of stuff, right? Starting out with two partners. And even before, doing it by yourself. Focusing on this time, two partners, then one partner, then no partners. Like how have you managed the stress through this whole experience and life cycle?

[00:17:25] Jennifer Stewart: It's been a learning experience. Obviously, I teach productivity and so there's a lot of tools that I teach that I have had to learn the hard way that I really needed to implement for myself. And so, I teach them with more vigor now because I know why they're there. The biggest one for me and it’s so funny because I was telling you before we started that I ran a four-hour class this morning and this is one of the big things that I taught is the big rocks, which is a Stephen Covey concept. The idea being that you take care of the big things that are important to you first and then all the little things will trickle in and fill in the gaps. And it's a whole video that you can look up, but I won't go into any more with that. But I've always loved this concept from the first time that I saw it. And that is how I've gradually improved it over time. I was definitely not perfect to begin on this, but I've improved over time, figuring out what those big rocks are for me, and especially my calendar tends to run my life for me, and that's just the way I work. And so, the big rocks, the big, important things to me go into the calendar first. And so, those for me are time spent with friends and family, traveling with my husband, hobbies, things that bring me joy and refuel me go in the calendar first. And then I figure out where the clients go because that's definitely one of the next most important things for me. And then all the other business things fit in and fill the gaps and fill in the free time. And so that's how I like to run my calendar, which then runs how I do everything. 

[00:19:14] Sanjay Parekh: Yeah. So, that's interesting. Like looking forward at it, then obviously you might be scheduling clients and whatnot. So, if something on the personal side comes in, then that takes priority, and you reschedule all the clients. Is that the way you manage it? 

[00:19:31] Jennifer Stewart: It probably would be if it was an emergency. Now, if it was just something fun that came in, the client takes priority. For me, it's typically what's on my calendar already takes priority unless it's an emergency. If one of my parents got sick or something like that, obviously I would rearrange everything to take care of that, but for the most part, all of my refueling things go on the calendar first, then clients go on the calendar and then everything else from there. And so, that's how I try to keep my sanity and keep that work life balance, if you will. 

[00:20:11] Sanjay Parekh: Yeah. Okay. So, talking about work life balance, let's talk about setting boundaries because the business that you're in, people have problems with technology all the time. 24/7. You could be on speed dial and being called all times of the day and night. How do you set boundaries between your clients and let's just call it sanity, and having to deal with all that stuff?

[00:20:38] Jennifer Stewart: Yes, exactly. Most of the clients understand that I pretty much follow a business schedule Monday through Friday. And then most of my clients also understand, I say most because we can't say all, but most of them understand that I am also a night owl. And so, I don't tend to take any clients before 10 a.m. I will, if someone really needs it before then. I will shift things. But I won't go before nine. And yeah, it's just the way I'm built. And so, if I'm not going to be helpful to somebody early in the morning, I don't want to work with them early in the morning. And sometimes I'm not up early in the morning. 

That's one of the boundaries that I set and they also, I have the conversation with my clients because of what I do. A lot of my clients have email overwhelm. So, we have that conversation about, what is your best mode of communication? And so, whether it's texting, emailing. Mine is email and a lot of them know that and they're fine with that. And so, that's another boundary that inserts itself. I've had a few more clients lately that are very text based and I'm still actually learning what my boundaries are going to be around that. Because they are texting me, not at all hours of the night. But sometimes at really random times. So, I think some more communication with my clients is going to be called for there. But that's the thing with any kind of boundary is just communicating those boundaries. And then again, going back to the big rocks on my calendar, what's the most important, those are set in stone on my calendar. And so, everything is, that's a boundary in and of itself that I've created. 

[00:22:33] Sanjay Parekh: Yeah, that's interesting. I, like you, I'm a more of an emailer than I am a texter. But with some recent newer innovations, like I love having texting in the browser sync to my phone through Google messages. That’s fantastic, it makes it a lot easier. And having WhatsApp on the desktop and being able to deal with them and having the whole history there. It does definitely make it a lot easier, but you do have that issue of you expect that instantaneous response and to me, even when I send text messages, I'm like, you respond whenever it's not urgent. If it's urgent, I'm calling you on the phone. Like I'm talking to you live. That's urgent. Everything else is not urgent at this point, but it's interesting. Not everybody views these mediums the same way as you and I do. 

[00:23:24] Jennifer Stewart: Absolutely. Yeah. Many of my clients, it's text me or I'm not going to see it. Which is, that's new and different for me, because I have the whole range of clients. I have young clients that just never really learned digital organizing and digital productivity, but then I have the older clients that just don't know how to use any of the digital stuff. And so, they're the whole realm of communication styles too. 

[00:23:53] Sanjay Parekh: Are most of your clients, do you work with them online, in person, a mix of that? How is it? 

[00:24:00] Jennifer Stewart: Yeah, it's almost a complete split right now. I actually do quite a bit of corporate training through third parties as well. And so, I'm contracted to come in and do those trainings. So, it's a really good mix, probably a third of each. So, a third of corporate, third that's in person, and then a third that's on Zoom. 

[00:24:19] Sanjay Parekh: Is there one that you find more fun than the others? 

[00:24:27] Jennifer Stewart: I always love the one on one the most, but honestly, in person or virtual, it doesn't matter. Just the fact that it's one on one. I can't do like back-to-back-to-back Zoom or Teams or whatever. I can't do all of those back-to-back-to-back. So, I probably can't do as many as I could as in person, but if I definitely have been working one on one with a client, that is what refuels me and makes me excited. And I love what I do. 

[00:24:56] Sanjay Parekh: And so, what's interesting is when you started this in 2016 it was probably all in person, right? The virtual is not as much. 

[00:25:07] Jennifer Stewart: Yes, that's a really good point. I hadn't thought about it cause I'm so in the virtual mindset now, but yes. So, what happened is, yes, we were very much in person for everything. And then 2020 just kicked us in the pants and said, okay, time to go virtual. And that was actually also when I started my YouTube channel, because I had always wanted to do it. I knew it was something I needed to do. I needed to get online. I needed to be in front of a lot more people. And again, COVID and pandemic is what pushed me to get that done as well.

[00:25:44] Sanjay Parekh: Yeah. Yeah. That's interesting. Silver lining for you that COVID and the pandemic happened because you were able to get those things going. Okay. So, let's talk about going back in time. You've now been doing this for, what is it? Seven years, right? Seven years with this new company.

[00:26:03] Jennifer Stewart: In total with, yeah, with the new company in total, it's been about 12 years. 

[00:26:07] Sanjay Parekh: Twelve years, so lots of learnings, lots of time. If you could go back in time and do something differently, what would that be? And why? 

[00:26:19] Jennifer Stewart: I think the only thing that I would do differently is how I approach it. All of the choices I made, because you always hear this when people talk about going back in time, I would do all the same things because it made me who I am today, which it's actually very true. And the partnership, sure, it was really hard when I lost one partner and then two partners. And each of those transitions was very hard for me, but it made me stronger, and I think it made my business better. So, what I would change is knowing that I can be myself from day one. I was trying to fit a mold and I was trying to fit a mold that didn't really exist. So, it was kind of like, I was trying to see what organizers were doing, but technology organizing, or technology productivity and training didn't really exist as a small business. It was usually big companies, tech companies that were doing trainings and things like that. And so, I was trying to fit what I thought the mold should look like. And I was trying to fit what other people were doing. Colleagues that really weren't doing the same thing as me. And so, I think that's why that first company didn't do very well because I wasn't being myself and being true to who I wanted to work with and what I wanted to do with them.

[00:27:42] Sanjay Parekh: Yeah, that makes sense. Okay. Since you're a tech person helping people with productivity and all this stuff, is there a technology or an app or a system that you've implemented that you would recommend to everybody that they should absolutely use this one thing? 

[00:28:02] Jennifer Stewart: Okay. So, the very first thing I want to say as a productivity trainer, is there is never a one size fits all. So, that's the first thing I would point out. 

[00:28:13] Sanjay Parekh: But as the host, I get the option of making you say a one size fits all. So, that's my prerogative. 

[00:28:20] Jennifer Stewart: I will. I'll give you a couple of things that I use, but I do want to preface it with have your system first, figure out what works for you, have a plan and know exactly what you need the technology or the app or whatever to do for you before you implement it. Because so many people are like, oh, the cool new app, I'm going to use it. And then they're like, it didn't work for me. I used it for a week, and it didn't work for me. It's because you didn't have a system in the first place. I've worked with several clients where they're like, the next tool, the next tool, the next tool. But the system wasn't in place in the first place. And so, none of the tools will work if you don't have a good system. And so that's the first piece. 

But once you know what it is that you need and want, and you have a plan for it, then you can start to look and see what apps fit the best. So, I work in both the Microsoft realm, the Google realm, really all the realms. And my favorites – I love task and to do apps. And so, for Microsoft and Google both. I like their task apps they have. So in Microsoft, it's Microsoft To Do. And then in Google, it's Google Tasks. And I really like both of them. I tend to use Google tasks more just because that's the program that my email runs through. But I really like both of those task programs. 

[00:29:40] Sanjay Parekh: Yeah, that’s great. I feel like I'm perpetually on the hunt for the task manager that works for me. And I think I've narrowed down on the thing that works for me, but which happens to be neither one of those, which is interesting. 

[00:29:54] Jennifer Stewart: Yeah, exactly. And everybody's different and there's so many different things. The reason I like those two is just because they're simpler and so they don't have the bells and whistles that you have to learn. And especially for my clients who are older. There's less that they have to deal with. 

[00:30:08] Sanjay Parekh: Yeah. And that seems to be one of our challenges with technology, right? It's fine for people like you and I that are technical and understand it. But I feel like I see a lot of apps and there's just so much. And honestly, there's some apps and I can't figure this out. This is like too much. And I don't know who this is targeted to, because if I can't take the time and figure it out, who actually is out there? And so, I think there's definitely a challenge with things that are being built for consumers today and businesses today that it's just, it's too much. Sometimes simpler would be better. 

[00:30:43] Jennifer Stewart: Yeah. And sometimes what I'm tending to see, more and more, is very niche products, which I think is good. So, if you fit this exact mold with all these different pieces, then this is the app for you. And again, I still hold to, think about what your system is first, because your system may still may not match what theirs has, even though you fit their niche.

[00:31:07] Sanjay Parekh: Yeah, that's great. Okay. Since you've done this now a couple of times, if you were talking to somebody who's thinking about taking the lead and launching a small business like you, what advice would you give them?

[00:31:23] Jennifer Stewart: The advice that I would give is something that I've heard a lot lately, which is, don't wait for it to be the perfect time. Because it's never going to be the perfect time. Never the perfect time to have a kid. It's never the perfect time to buy a house. It's never the perfect time. It's never the perfect time to open your business and give it all of your time and energy. 

Caveat to that though, you've got to make sure that it's going to be stable, especially if you're the person who's bringing in, paying all the bills and things like that. You've got to make sure realistically that it's going to work, but if you've done that work and you can see clearly that this business is going to be successful, just go for it. And the other piece to that, that I was not very good about, and one of the reasons I think that first business wasn't doing as well, is ask for help. The biggest thing that entrepreneurs often try to do is do everything. And so, you have to realize what your strengths are, and maybe even do this before you would step out on your own and leave that full-time job. Figure out what are your strengths, what are your weaknesses? Focus on your strengths. If there's a weakness that you want to increase and get better on, then absolutely focus on that, but really focus on your strengths and then find people that can fill in the gaps for your weaknesses and get help from them, whether it's coaches or consultants or getting people to outsource with. That's what I would recommend is go ahead and try it. If something's not going well, then find the person who knows how to do it and hire them. 

[00:33:01] Sanjay Parekh: Yeah, that is great advice. I often say to founders or wannabe founders. That if this is something you want to do today is the best day to start doing a company, right? Not tomorrow, today. And the only better day than today was yesterday. So, since we can't do that today would be the day. 

Jennifer, this has been fantastic. Where can our listeners find and connect with you online? 

[00:33:28] Jennifer Stewart: My website is GatewayProductivity.com and then the best way to connect with me or to see more of me is my YouTube channel. I've got over a hundred free videos that are technology training from all different realms. I don't have a ton on Mac yet, that's coming. But, I do have Microsoft, Google, all those different things and then I'm on LinkedIn. I'm very active on LinkedIn as well. 

[00:33:52] Sanjay Parekh: Awesome. Thanks again for coming on today Jennifer.

Thanks for listening to this week's episode of the side hustle to small business podcast powered by Hiscox. To learn more about how Hiscox can help protect your small business through intelligent insurance solutions, visit Hiscox.com. And if you have a story you want to hear on this podcast, please visit Hiscox.com/shareyourstory. I'm your host, Sanjay Parekh. You can find out more about me at my website, sanjayparekh.com.