Visionaries Podcast

Embracing Fear As An Entrepreneur with Jessica Totillo Coster

Jessica Totillo Coster

Are you on the fence about taking the leap and starting your journey as an entrepreneur? The fear of not sure what is going to happen is too strong in your head? 

Well, today we are going to explore the perks of being an entrepreneur with Jessica Totillo Coster that shared with us her amazing journey.

Listen wherever you enjoy your podcasts!

In this episode, we’ll explore:

  • Embracing entrepreneurship without fear
  • Human side of being an entrepreneur
  • What you need to know before taking the leap

Notes from this episode:

  • [01:24] Jessica Totillo story from her corporate job to taking the leap
  • [10:57] There’s no perfect way of being entrepreneur, find what works for you
  • [15:07] Being scared is part of the entrepreneurial journey, if you are not scared you are doing something wrong
  • [22:46] Before taking the leap make sure you validate your idea

Click here to listen!

Rate, Review, and Follow on Apple Podcasts.

Subscribe to our YouTube Channel for Podcast Videos.

Other ways to enjoy this podcast:

Today's Guest

Jessica Totillo Coster

Jessica is an eCommerce strategy expert and supports female entrepreneurs. 20+ years of retail & eCommerce experience gives Jessica the ability to support female entrepreneurs in creating the right strategy for their business.

After 20+ years in retail and 3 years as the only employee of a 7-figure eCommerce business, now she is working with the top experts in eCommerce, SEO, web development, and digital marketing.

Jessica supports female entrepreneurs with actionable strategies and tactics to grow and scale their eCommerce businesses.

Facebook URL

Instagram URL

LinkedIn URL


Welcome to visionaries where we explore stories, strategies and insights from the world's most inspiring entrepreneurs, brands and creators. Were on a mission to help visionaries like you stand out and monetize their knowledge, influence and message online. Exploring topics like business, marketing, creativity, and personal development. Let's build your vision for a happier more meaningful life, business and community together.

Jessica Koster worked over 20 years in retail in three years as the only employee of a seven figure e commerce business. Now she's working with the top experts in e commerce, SEO, web development and digital marketing. Jessica supports female entrepreneurs with actionable strategies and tactics to grow and scale their e commerce businesses. Let's get into the interview with Jessica. Jessica, it's so good to have you on.

Thank you so much for having me. I'm so excited to chat with you today. Yeah, of course. So one thing I would love to get into is breaking down your personal journey into entrepreneurship. And you said kind of happened by accident. So tell us more about that. And how others listening or watching watching can relate. Yeah, absolutely. It definitely was by accident. So I had a full time job, a very demanding full time job. And you know, I loved what I did, but I didn't really love who I did it for. And I knew that I wanted to get out, I just didn't know what that was gonna be right. And I've been in retail for 20 plus years. So of course, I just naturally thought I would have another retail business. So I, you know, I played around with that for a while, and it just wasn't, I just wasn't that into it, I guess. And then, interestingly, it was right around the time where MailChimp, and Shopify broke up. And it was this whole big thing. All of these entrepreneurs, ecommerce entrepreneurs didn't really know what to do. And I was already in a bunch of entrepreneurial Facebook groups, because they just really loved to be around that energy. And so I started talking to them, but another email platform that I had been using at my day job for the last three years. And then all of a sudden, people started messaging me.

And they're like, Oh, well, I just switched to that platform, but I'm really struggling, can you help me or I want to move, but I'm so overwhelmed, or I don't have the time or something. And I was like, Huh, All right, let me help these people. still nowhere in my head, did I think I could create a business out of this. And then after working with the first my first two Oji clients, right, I remember working with them and thinking, this is like the best job I've ever had. And I'm sitting on the couch with my husband. And he's like, so are you going to create a business out of this, and I was like, I could create a business out of this. So one of the things I realize is for someone who is maybe you're still in the nine to five, you're kind of trying some different side hustles the things we know really well, we take for granted, because we think everyone knows them as well as we do. And what I learned is, that is not the case at all. So what I thought was like, common knowledge people are willing to pay me for, and I'm able to bring so much value to them. And so now, I was I did it on the side for about 18 months, because I was just too afraid to quit my job. And then in September of 2020, I went full time. And as soon as I took that leap, I saw an immediate, you know, like increase in my business. And it's been an amazing ride. And I'm just super excited for what's coming. Yeah. And that's all very recent, right? I mean, months ago, nine years ago. You know, what's so interesting, too, is I can totally relate to you on this because it wasn't too long ago that I was in similar shoes. I was also in LA working for it was a great company, big, massive global company. But then I started bootstrapping a business on the side and realize, wait a minute, I'm making more money with this side business. Yeah. And with my main day job, and then there's more of that autonomy as an entrepreneur. And so I think for the true entrepreneurs out there for those who are like, Hey, I have this ambition. I have these ideas. And maybe I'm not making money at it yet. Or maybe I'm starting to there's plenty of examples.

You know, Jessica's one. I'm one many others that hey, it's gonna be scary no matter what it's kind of like, Jessica, I don't know if you have any kids, but we just had our second Get one, when you have Thank you. When you have your first one, it's like, you're never really ready to become a parent. You know, people are like, they're trying to prep you, and there's never that right moment. And the same thing is with other decisions. And so it's just you just got to take the leap. And yeah, things will work out. What was it? So after you quit, right, exit interview, I imagine all those things. The day that you're sitting at home, working on your own business, I like officially full time. What was that feeling like for you on that first day? So what's so funny is so obviously COVID happened, right? And so we had been working from home for a long time at that point. And it didn't hit me right away. Right. Like I knew, obviously, I wasn't working on that other stuff, though, I actually still consult for that business, because we had some big projects we were working on when I left that I really wanted to see through and they needed the help. And I'm still now almost 10 months later, still working with them. So but those first few weeks, like it took a while to sink in. And I think it's so silly. I think it was the first time where I was able to in the middle of the day in the middle of afternoon, say, Okay, I need to put this all away, and I need to go run out to do an errand whether it was like going to the dock, it was something really silly like that, oh, I don't have to get permission to do this. I don't have to take the entire day off so that I can go to the doctor for an hour. And that was a moment that was where it like actually clicked. And it was really freakin cool. I really love it. Yeah, you know, and it's, it's funny, too. I mean, so I've gotten more used to, but it's like the next day. Like it, it is kind of that odd feeling as you get used to that new kind of work lifestyle, because it's unfamiliar, so many who don't go that path or even, you know, what 2020 taught us more is like, hey, virtual working is even if you work for big employer still, which is amazing. Yeah.

There's gonna be a little bit more of that autonomy with your schedule. Yeah, and less monitoring. And like, when you walk into an office, and you have all these employees around you, there's kind of that accountability. And in that structure, that if you're not there at a certain time, you don't leave at a certain time. There can be kind of that added strain. Within those hours, sometimes, there's still jobs that demand that and need that. But we're just seeing a big shift in the workforce. I feel like around this, not only opportunity to jump into entrepreneurship, but just to simply work from home for great employers out there. Yeah, absolutely. And, you know, the company that I worked for super old school, like super old school. I mean, we had key cards, and if you were swiping that thing late, like they knew, we also like time cards, just to get out of the building. Okay, yeah, right. Yeah. So it was for that, but it serves some other, you know, like underground purposes, too. And I get it, we had like, alternative work hours. So we didn't, you know, we had every other Friday off, which was really cool.

But then they became really, really strict about that time. And, you know, I mean, like, we all need to go to work and be on time, but it was like, when we all went working from home. I the the productivity actually went up, right? Because you're not distracted by each other, getting up going to the kitchen running into someone in the hallway having a random conversation about nothing, just like trying to do anything other than sit at your desk. I feel like when you're in an office, you're just home working and I feel like people actually work more at home. So I think like that discipline piece goes a little bit both ways. When I first left, that first like week, I watched a lot of Netflix but I was like to ask you like working Netflix? Yeah, I was like, I just need some time. Like I've been doing this on this side for 18 months. I just heard this is like my little mini vacation. But it's I thought it would be harder actually to keep myself disciplined while working for myself. But I have to answer to my clients. right because I do a lot of done for you stuff and consulting and things like that. So I do have someone to answer to so that keeps me in check. Yeah, yeah. Which is important to recognize that Yeah, cuz I think there that is a big common fear and maybe maybe misconception is that hey, how like I'm not that self directed, self disciplined person to know. I'm going to show up from from nine to five Every day to know that I'm going to work and hat, sometimes you have a boss, but they come in different forms. And they may not be as bossy. But they keep that accountability in check. Which Yeah, which I think is is important to have, especially from a done for you or agency. Time place. Yeah, absolutely. And you know, I think you, you eventually find your groove. So, you know, my husband's an entrepreneur too. He does real estate photography. So he goes and shoots, you know, during the day, he's also a night owl, right? So he'll get home from a shoot in the afternoon, he'll just kind of do whatever he is going to do. And then you know, later that night, he'll go maybe edit a video or something like that. And I work a lot late, too, because, you know, sometimes I need my day to go, do whatever. And I'm also a night owl. And so you just kind of figure out what works for you. But there's no, there's no perfect way, or there's no right way to be an entrepreneur. I'm so glad you said that, by the way. I was. I think when we're early on to it, we get caught up with it be like, oh, there is this right way.

Like whether you have a mentor to follow or you've seen, you're trying to model someone else's success based on the like, step by step process they may have taken. And I was watching this parody video that was kind of making fun of the grinding, hustling entrepreneur. Yeah. And that like, Oh, my morning routine, I wake up at 3am I do the series of steps check them off. And then I jumped to this next thing, and I'm like, highly productive. And then it's like, and I never see my kids and family and I don't care. Yeah, not about that life. Um, so we're recording this at 9am pacific time. I usually like I don't have my first call before 11. That's just how I do it. And that's the beauty of being an entrepreneur, like it's your business, you get to make your decisions and do it your way. I've never been a morning person, I'm never gonna get up at 5am and have like a 12 step morning routine, like my morning routine consists of roll out of bed with one eye open, go get coffee, don't talk to me while I'm drinking that. And that's it. I still have a successful business. Yeah, you know, and it's interesting, too. I feel like sometimes people need permission.

Because there's sometimes a shaming part of the entrepreneur culture around, bingeing on Netflix, or doing these other things like my wife, and I can have a routine where we enjoy our TV shows on like the hundreds of now streaming platforms that exist. Yeah, and, and that's just just a part of like, how we disconnect or connect, and have fun with that leisure entertainment side. But But I felt like I remember that early on is like, you can't be successful. If you're watching Netflix or doing these things. And I there's just, there's certain messaging that gets put out there, that definitely rubs me the wrong way. And I think it speaks more to what you've been referencing, is this idea that we all have our own personalized vision for our business in our life, and it's not going to look like someone else's. And that we need to recognize that and then craft what that schedule may look like. And be happy with that. And know that may evolve over time. And it will, it will evolve. And look, I I got into entrepreneurship, yes, to help people, but also to build a life for myself. I didn't do this to create another job. And so I'm really, really intentional. And I've, you know, there's services that I have offered and stopped offering. And I've made a lot of adjustments just in the 10 months that, you know, I've been full time. Because I'm being really intentional in do I enjoy this. If I don't enjoy it, I'm not going to give it my all I'm not going to do a great job, it's not going to be as valuable for the person I'm working with. And ultimately, their success is my success. So the way I do that is by offering things that I'm really passionate about. And really leaning into that and being realistic. You know, there are some people that we talk to my husband talks to and you know, they just have a different, like, they don't care if they never travel or, you know, they'll just work the grind every day day in and day out.

They'll take every last gig they can get because they're so afraid that the next one's not going to come. And I'm just not about that life. Just not so, yeah, you know, it can be scary, but I think That, like, if you are not I heard someone say this, I think I don't remember who it was. But she said, like, if you are not scared as an entrepreneur, like you're doing something wrong. You know, it's interesting, because I feel like we can relate on a lot of levels from working, we'll say for corporate, which, personally, it was an amazing experience. And I, as I was starting to side, hustle, you know, side work on a side business, I recognized, oh, wait, I've always kind of been entrepreneurial. So like, I can own this. But one thing I recognized with a lot of my co workers is they were very comfortable. That I guess is the word where you get into this job, and you're getting comfortable, and maybe you're in it for 1020. Some, you no longer in the same company, you know, it's not going anywhere, anytime soon. And you know, you're getting bonuses and pay raises every year, maybe some promotions, every little bit. And that's a great structure, and especially that existed in the previous generation of those who are now retiring. Right. I mean, I saw that definitely with my dad who retired a couple years ago. And it was it's one of those shifts. In reality, though, where this same company I worked for 2020 hit them, probably one of the hardest of any company out there. It's a massive global company, they have 1000s upon 1000s of employees. And now all these people who were seemingly comfortable, all sudden, are out of work.

And, and so it's, yeah, and I think it's an interesting shift to be like, wait a minute, I think whether you're an entrepreneur, an employee, doing amazing whatever company you work for, there's that, that sense of feeling uncomfortable, but what was that word? Use that emotion? discomfort, or, oh, what about being an entrepreneur? I think I said, scared. Scared. Yeah, there we go. Yeah, like, in some ways, you kind of need to have that scare, always kind of back there to know, like, maybe you have a backup plan, or maybe you just know, like, things will never be 100% the same day to day, yeah, here. And they need to be ready to ship. I mean, I've been talking my wife about this, with how the business has evolved and in good ways. And like sharing all these fears, and like ways that I'm scared of what's going to happen. Like it could turn out this way it can turn out this way. It's just that's the human side of being an entrepreneur is like, there are a lot of what ifs or unknowns that you can't plan for everything. Yeah, and know how it's gonna go down? Yeah, oh, my gosh, totally. And I, I it's so funny, because when I went to school for fashion merchandising, right, I thought I was going to be a buyer. And I was going to work my way, like up the retail ladder, corporate ladder and all this stuff. And, you know, then I spent some time in the industry. And I was like this, this sucks, actually. And then I went down, like working in boutiques, and I opened my own frickin mortar boutique. And that was all I loved that. But you know, I was like, stuck being in this like store. And then about 11 years ago, I decided, Okay, I don't want to live in the snow anymore. I'm originally from New York. And so I picked up, I moved to California, close my store, moved to California had to start all over. And then I started going down this marketing path. And I thought, Okay, I'm gonna do this this way instead. So I was working in marketing for retail companies, because that's just what I had always done.

And then I was in that same mindset, okay, I'm just going to work my way up the ladder here. And I, what I realized later on is that wasn't my story. That was the story of some of the people around me who didn't really know any better. Because that was the story they had. And I think about to when I and I'm a grown woman, right, if you guys are only listening to this in audio, I'm a grown woman, I have a big gray streak. That's real. But when I was quitting my job to go full time. I did not tell my mother until it was already done. Because I knew that she was going to want to talk about it. Is this the right decision? Are you sure right, and it's all coming from a place of love, and I appreciate that, but that is her own fear being projected on us. So I think that also has a really big effect on whether we decide to take a leaf, the leaf bright and how we kind of end up going about it. So if you're like those of us who were like teetering on the entrepreneurship seesaw, you know, We're just kind of we, we just have to get really, really clear on an honestly just like, if there are naysayers, like, just don't even talk to them about this stuff, like just do your own thing. And you can tell them when you're making the big bucks. Right? So when I first started doing it on the side, and my mother was kind of like, oh, not sure. And then I told her how much a client paid me to do something. She was like, oh, like, yeah, see. But you know, that was, that was her story. And that's what she's done. She's worked for the same, you know, company for a lot of years. And now she's just kind of waiting it out until it's time for her to retire. And that's just what they did.

But you know, it's a different a different world now. And I mean, companies, they don't have the same loyalty to their employees, either. anymore. Yeah, the whole idea of pensions or the I mean, there's still plenty of benefits in many companies, but it just looks so different. It looks so different. Yeah, you know, it is interesting, too, because I mean, I, I would definitely say though, if, if you don't have any kind of way that, you know, if you rely on your source of income from an employer, before you quit, you definitely want to make sure that you know how you're going to bring in money. You know, just be like, I want to be an entrepreneur, like I, it was funny I was this is couple years ago, I think I was at Disneyland with my family. And we're talking to some people on you know, one of those long lines. And the couple were older, I think they're retired. They're like, you're asking, oh, so what do you do? I'm like, Oh, no, I'm an entrepreneur. I think I described that a little bit. But usually when I don't know people, I keep it generic to be like, yeah, yeah, yes, I run this kind of company. And they're, they're like an entrepreneur, and they kind of like, you could tell in their eyes and their body language or like, to them what an entrepreneur meant, was someone who didn't make any money. They just said ideas. And yeah, it was pulling from personal experience, I think their son in law is a self proclaimed entrepreneur who doesn't make any money for their, you know, their daughter's family. And so yeah, it was just one of those things, though, where it's like, okay, like, let's make entrepreneur means something.

Like, there's a lot of pride, I think, with an entrepreneur, being an entrepreneur. And so make it mean something for everyone. That means, like, you can do it, or you can be working for another employer. But make sure that you know, your product or services validated in some form that people are willing to pay you for it and don't just like jump into an idea that is not going to make you any money. Oh, my God. Yes. So, so important to validate first. And, you know, I tell, you know, that I work, usually with product based businesses, and I tell them the same thing, you know, like you have to prove product market fit, is there a demand for what you're selling? And then how do you set yourself apart? Right? Because, and this is true in product art, or service? Like, very rarely are you doing something so unique from everyone else out there? You know, like, it's not enough to just like, build a website and say, Hey, I offer this like that. That's not how this works by any means. And when I made the leap, my husband and I, he's much less conservative than I am when it comes to money. But he also because we're old, right? Like, we have like real bills, if I were in my 20s, it would have been like, it doesn't matter. Let's just see what happens, right. But as a grown up, you're like, Oh, I got all this stuff I got to pay for. So I mean, I had six months of living expenses before I even took the leap to just and I had already been making money in my business before I did it.

And that just takes the pressure away. And lets you really feel out what you want the business to look like. And you don't have to take every client right? A lot of people when they're if they're in a service based business and working with people they don't like working with because they're like, I just need more money. I need to pay this bill, I need to pay the rent. How am I going to do this? And I really did not want to be in that position. So I don't recommend anyone leaps before without a net. There we go. Yeah, have a parachute. Yeah, for sure. Man, this is so good. We you know, and it's it's interesting, too, because I didn't imagine our conversation going this direction. Pretty good. Because you know, here you are a digital marketing expert for e commerce, you know, retail type brands, right? And we could have talked all about that and what that looks like, all the strategies and tactics, but I find the storytelling behind other people's experiences can build up confidence and maybe like every find identity for people to know like, hey, maybe I can do this too. Or maybe I followed a similar path and I It kind of validates to know, like, Hey, I'm, I'm going the right direction, there's something here I can do. Or it's good to be in this role, whatever it may be for you watching or listening. definitely take note around what Jessica story may look like for you.

Yeah, I love and I love talking about this, because I think being the person who wasn't sure who was afraid to take the leap, and I remember, you know, when we were my husband and I trying to plan Okay, planning my exit, right, and we're doing this together, because we're married. And that's what you do when you're married, right. And I was originally planning my exit for the beginning of 2020. And then COVID happened. And like I mentioned earlier, my husband does real estate photography. So for those, like first two weeks, they had no jobs, and we were alive. Well, I'm not going to quit now. Because we don't know like, What's going to happen? We got lucky in that, you know, California deemed real estate essential, and they were able to continue working. And then so many people were moving out of California, they got really busy. But, yeah, but we were still like with this uncertainty. I'm not gonna leave my job right now. Right. And my company had actually furloughed, a bunch of people because all we had 35, retail stores, all of them were closed.

Being part of eecom is kind of what saved my butt. And then we were busier than ever. And at that point, I was just like, I'm just grateful that I have a job. And I'm not gonna rock this boat right now. But while him and I were talking about it, and trying to decide, and you know, there was a part of me being the scaredy cat that I was, that was really waiting for him to give me permission to quit. And say, like, Don't worry, if it doesn't work out, we'll figure it out. Like, I needed to hear that. But what he said instead was, you'll know when the time is right. And I did. So just like they tell you, you know, with relationships, like you'll know when it's the right person. And I didn't really believe that until it happened to me in my mid 30s. And I'll say, Oh, that's what they mean. Okay, I get that now. And the same thing was with taking the leap full time in my business. So that's not to say it's always an easy path. But your intuition is really smart. And can really if you learn to listen to it can really bring you down the right path. Yeah, what a great message. What a great message. You know, and trust in that too.

I think a lot of us second guess the thoughts and feelings we will be having around a choice. And sometimes I feel like the right choice may be identified after we take action, and make the right for us to feel like oh, maybe this was right, in retrospect. Well, this has been so good, Jessica. Where can people learn more about you and what you're doing in the online space? Yeah, you can find me in all the places at e commerce badassery. So that's my website, my podcast and my social handles. I hang out mostly on Instagram. Easy, so good. Yeah. Make sure to include that down below in the description of this episode. And Jessica, thanks again. This has been amazing. Thank you so much for having me. Great combo.


Dallin Nead

Dallin believes in putting family and God first.

He's the Chief Vision Officer of Content Supply, Advisor to multiple startups, serial entrepreneur and an award-winning producer.

He helps brands create authentic, results-driven media so they can share their message and vision with the world.

He helps brands clarify, create, and communicate their vision for a happier, more meaningful life, business, and community.

He consults with small and large companies including Princess Cruises, U.S. Marine Corp, Teachable and many others.


Hire A Certified Marketing Agency

Certified Content Supply Agencies will grow your brand with 100% done for you agency services. Full service video ads, course launches, photography, podcasting, and more. Book a free strategy call to get started.

Hire An Agency


3 Shifts To Skyrocket Your Business With More Visibility, Revenue And Impact Using Video