7 Years of Side Hustling Turns into Full Time Entrepreneurship With Keshia M. White

Keshia M. White worked on her side business for 7 years while holding a full time job, then she made the jump and now works full time as an online entrepreneur. This is a story of perseverance in a different light, when someone cares so deeply about what they’re working on that they’re willing to […]

Keshia M. White worked on her side business for 7 years while holding a full time job, then she made the jump and now works full time as an online entrepreneur. This is a story of perseverance in a different light, when someone cares so deeply about what they’re working on that they’re willing to put in overtime for a very long time to make it a reality.

Keshia’s website: https://www.keshiamwhite.com/

Episode Transcript

Josh Haynam:
Hi everyone. This week, we’re here with Keshia White. She’s a brand strategist who is currently replacing about 90%, almost all of her previous salary, but now working for herself. So that’s where you are today, Keshia, but where did that all begin?

Keshia M. White:
Yeah. So it’s been quite a journey. I’ll say for sure. But I guess I’ll start back to my corporate days. So rewind, I guess, about eight or nine years ago, I got my first corporate job after really not having a job for a little bit because I kind of did a miracle work for like a year. I didn’t have to move back home with my parents a couple of times after college, I graduated in 2010 on the heels of the recession. So once I finally found that first corporate thing, it was in corporate sales. So I moved to the Atlanta Georgia area to work at AC&T. They had this sales training program and I did not really want to be in sales at all. It was just all that I could get in that desperate point at the moment. So that led me into that sales career and then was kind of found myself in jobs every day that I didn’t really like.

Keshia M. White:
And I was just there for the money. The money was okay, but I just was not enjoying what I was doing every day. So in my free time, I would always just keep looking for other options because I’m not the type of person to just, if I don’t like my job, just sit there and be, I hate this job, but this is just the life I have to get stuck with. I was like, I’m not going to be stuck with this life. So I would just do, pursue different hobbies in my free time from singing and random stuff like that. So I eventually hire a career coach to kind of help me get some clarity on what do I want my career to be? Then eventually I started a lifestyle blog because I kind of had some interest online with seeing people talking about what they were interested in online.

Keshia M. White:
So I was, Oh, that might be a fun, creative hobby to just make a blog online. So yeah, so from there, I just noticed people online who were full time bloggers who maybe sold a service in addition to their blog. So that had my wheels kind of turning and I was, oh, that might be a cool business model, to be able to have an online business where I’m making money off of a blog and then also making money doing a service. So since I was, at the moment, I was enjoying doing web design, creating my own blog websites, so I, of course, it was a hobby, so I wasn’t about to pay a web designer to just do a hobby blog. So I was, okay, that might be a good service thing that I could offer to be able to make some money doing something and also doing a blogs.

Keshia M. White:
So started taking web design courses in the evenings, kind of popped over to my next sales job in software from there and a couple other sales jobs after that, but I was just always in my free time slowly working on the business, but barely making any money back then. Because I had no business plan and yeah, and stop me if you ever want some clarity on any because it’s a long story. Okay. So yeah, so it was a few years where I was just doing random task and services, I guess, because people at my day jobs, they would be, oh, well you have professional cameras. Oh, take my pictures. So then I would just randomly take pictures or they would ask me to do a logo because they knew I would do websites. And then I used to do random $25 website audits and eventually I made a $29 “How to be a blogger” work sheet.

Keshia M. White:
So back in those days I was just trying a bunch of random cheap stuff that really wasn’t getting me anywhere. And then in the meantime, still popping around from sales job to sales job, because one software sales job at this company, that was when I was a business development rep, so we were cold calling [inaudible 00:03:49] and I took the job thinking it was going to give me more flexibility to kind of work on my business because they said that you had work-from-home days, but ended up getting there, we didn’t really, it wasn’t flexible at all. They wanted us to take our work home a lot and I was like, oh no, this is taking time away from the business. So then went to a different company where I was in consumer products, and then while I was working there, that job was pretty easy. It was super easy.

Keshia M. White:
So it was the perfect job, for me to be able to work on my business at night, because it was just super easy and kind of Miller’s, one of those Miller’s type sales jobs where you were just kind of, “Yeah, you want this kind of paper? Cool. Here’s your order.” So at night I would go home and do all that random cheap stuff I was doing and yeah. And then eventually from there, I feel when I used to go to work every day at that job, they could tell I wasn’t into the job and I wasn’t. It was a paper type consumer products company, so it was super boring to me, but I just stayed because it was so easy. And then towards the end of my time there, we got a new director and they kind of acted like they wanted me to, give me a shot to move to the marketing department from sales, which didn’t end up working out.

Keshia M. White:
And then they ended up letting me go out of the blue. I didn’t even have a bad performance interview or anything like that, but I feel it was just, I guess they could just tell I wasn’t interested, which I wasn’t. So it is what it is. So, ended up finding another sales job at Infusionsoft, this marketing automation software company for small biz and entrepreneurs. So I was like, oh cool. That’ll be the perfect job for me to be able to use my business expertise in my actual one, 9-5, because in that paper company, I would have to hide the fact that I was working on something outside of work. You couldn’t talk about it at work or it was kind of looked shunned in a way. “Why aren’t you 100% into your job? You shouldn’t be working on something else.”

Keshia M. White:
But at that company, the fact that I was working on something else was an asset, because then I could relate to the people I was selling to more. So as when I was working there, I did end up pausing and I didn’t even work on my business the whole year that I was working there, because it was kind of intensive, it was a older startup because they were maybe 15 or so years old, but they were really ready to go public and trying to go really, really hard at aggressive holders. So it was a ton of work, so I really didn’t even have time to work on my business. But while I was working there, I would talk to small business owners about online marketing every single day. And I learned so much of what businesses needed to really be successful online.

Keshia M. White:
So it pretty much subconsciously was just kind of making entrepreneurship less intimidating too, because I was talking to full time entrepreneurs every day. And before I used to feel it was going to be so hard and so intimidating to make full time income, but just talking to those people in real life and the job everyday, I was like, wow, if all these people are doing it, I know I can do this too. So eventually there, I was in a remote office away from their home office. So if the culture kind of went a little crazy with our remote office to where I got demoted at 30 years old, it may not be that old to some people, but to me it was old to get demoted to entry level job. So I was demoted back down to that business development rep kind of job while other people got fired and I was like, Oh my God, now I have to cold call again all day. I hate that.

Keshia M. White:
And I did not want to say after that demotion. So I kind of tried to do a job search to see if I could get a job where you could help people get started on the software. That was that customer success type of software job, but I couldn’t get a offer. I would get to the final interviews for a few companies, but I couldn’t get a offer. So I was, okay. It was either go to another sales job again. That would have been my fourth company, I think maybe fifth company, I guess at that point, working in sales or I could just use these web design skills that I had started working on years ago and try to take my business full time. So at that point I was like, I know when I wanted to quit because I had some money saved up from the commission checks.

Keshia M. White:
So that was the good thing about being in that uncapped commission job, you can save a lot of money fast and I pay off credit card debts, so didn’t have any credit card debt to worry about, but I was just really, really nervous and scared to quit. And so then I ended up around that time when I was getting rejected from the jobs that I was applying to, I had a yoga retreat to Bali plan that I had already booked early at the top of the year in January, and the yoga retreat was in September in the fall, September 2018. And so I was like, okay, I know I want to quit, but I’m really scared. Let’s go on the retreat and just forget everything and see how I feel when I get back. And so it was pretty much going on that retreat, there were a lot of other women on the retreat who loved their careers and some of them have made a career change too and left the corporate world, and one of them, she had left and became an interior designer. She was all encouraging me to just go for it.

Keshia M. White:
And they all liked what they did for work. And I was like, I want to be somebody that likes what I do too. I’m tired of being miserable, because it had been seven years in sales and the jobs that I hated at that point. So once I got back, literally as soon as I got back, I was like, I’m putting in my notice, I’m leaving. And so I pretty much quit literally as soon as I got back from the retreat, and the day I quit, I started working on a marketing plan. So this was after not working on my business for a year, I was like, okay, I got to hurry up and ramp up the marketing again to get clients before I run out of money because I had six months of money.

Keshia M. White:
So ended up working on marketing. It took maybe a few weeks, only a few weeks really to get the very first client I got. And I came out of the gate with a $1,500 package back then. So I had done away with all that small stuff I was doing, a few years prior to that where I was barely making money. And then before I knew what I had, I had some more $1,500 clients and I brought the price up to $2,000 and this was for a brand and web design package at the time. And then before I knew it, I was overbooked to the point where I was like, okay, I have to increase my rate to $5,000 and take less clients. And so yeah, so it’s pretty much has been busy from there, and now I’m in a transitional stage to where I’m focusing on new service providers and helping them get their businesses started and getting the clients they need from the start, and I’ve kind of moving away from web design now. So yeah, so quite a journey.

Josh Haynam:
That’s amazing. That’s really cool. I think what stands out to me is it sounds like you saw a problem, you saw something that was going on and you actually experienced it for yourself from the story where you were trying to custom brand, custom design your own lifestyle blog, and you figured, or maybe you saw it’s expensive to have someone do that. It’s expensive to try to hire somebody for that, but it doesn’t seem that hard. So then you learned and you taught yourself how to do that. I’m curious what, because that’s a very particular mindset, right? Of, I see a problem and I want to try to figure it out myself. It’s not everybody that thinks that way. I’m curious where that comes from. Have you always been the type of person that sees a problem and wants to find a way to solve it yourself? How did that kind of mindset get into place?

Keshia M. White:
So I think, I guess I’ve probably always been that way. Because I’ve always been that little overachiever kid who was just really into the schoolwork and getting A’s and all that. I like getting awards and stuff as a kid. I don’t know why, but yeah. So I kind of have always been like that. If it’s something I want to do, I’m like, okay, I’m going to figure it out. There’s some tutorial out there or something I can Google and look up, because I will say back then it was a terrible website. It didn’t look good at all, but it was a website. It was done. So I had my little blog and I got started at least, and I still have some of the screenshots of each year of how when I kept learning more and more, how I improved.

Keshia M. White:
Oh yeah, and then I did start taking some night classes in design, too. So in my free time, I took one at General Assembly. They’re this tech class place. And then I did a little web designer certificate to get a little bit of help, too. Because I did get a little bit where I wanted some, if I had questions about the tech stuff and the coding where I did want somebody to ask, so those helped out and they were pretty cheap compared to what I spent on college, of course, so yeah, so yup.

Josh Haynam:
Yeah. Was that always a thing? Why were you the high achiever? I think everybody has a different reason for it, but I’m curious what your why was?

Keshia M. White:
Let’s see. I don’t know, maybe it might’ve been a little bit of my parents because they’re kind of really extra with when they’re, even though to me, they were super career-driven that much, in my opinion, but I guess they were really pushing for me and my sister. Pushing us to make sure we were doing well and we were always on the right path and that kind of thing, and then I guess a little bit of just my personality anyway. I was just kind of naturally like that, because I used to like to read and for some reason I used to get sad when school ended. All the other kids would be happy, “Oh, it’s summer. I’m going home to play!” And I’ll be like, oh my God, what am I supposed to do? I need stuff to read. And my mom said I would cry when school was over, which is so weird, I know. So I don’t know, I guess my little internal drive was just always there from somewhere. Who knows?

Josh Haynam:
Yeah, and I’m curious how that affected when you decided to make the jump to work for yourself, did any of that stuff come up as a fear or a what if, what if I do this? How does that play into this other side of you that sounds like it wants to kind of stay on the right path, right? Somebody who really enjoys school and enjoys learning and following the path, now you’re diverging off of that, what came up for you in making that choice?

Keshia M. White:
So I will say, I guess honestly back when I got my first little internship at 19, I didn’t really want to be in the corporate world because I didn’t really like the environment. It just seemed kind of stiff and boring to me, even though I knew I was kind of the high achiever, nerdy kid, but at the same time I kind of liked to be challenged. And I felt in some of those jobs, you’re kind of just sitting there in the same repeat task every single day, so you’re not really challenged. So I knew I didn’t really want to be there anyway, I just couldn’t think of anything else to do going into my twenties after graduation. But I do feel it kind of, like you said, going off path compared to what my friends were doing, because still all of my friends are still in the corporate world. I don’t have any entrepreneurial friends unless they’re new people I met along the way. But I felt, I don’t know, sometimes I think I maybe used to feel maybe guilty that I didn’t like that path.

Keshia M. White:
I’m like, well, I’m in a good company. I’m this huge company, and everybody’s like, oh, you work at this someone so and so company. And they like, you put you on work trips. I guess other things that other people would look at as prestigious and I just was like, if I was just okay with it and happy with it, I guess I would be just okay, and I would maybe not have all this work to do as an entrepreneur in a way. So I sometimes used to just kind of feel guilty that I wasn’t happy with that and I wanted to do something else. And then even a little bit with my parents, too. They always are like, “Oh, good job. It’s the best way to go,” because they’re super old school. So I felt they maybe would have been more satisfied with it, even now, I think, even though I’ve been doing this almost two years full time, but I think they still think like, “Oh, she’ll just get a job someday.”

Keshia M. White:
So I guess it will be a easier conversation with them if I was on that straight and regular path, but I’ll just, deep down, I’m like, “I don’t need to be told what to do every day or to be just in this office every day.” I like my flexibility, and I’m pretty self-sufficient and independent and productive on my own, so yeah.

Josh Haynam:
Yeah, that really stands out to me because over the course of seven years, right, you slowly built this thing up on the side and seven years is significant to me because I feel with Interact, that was kind of around the time things started to really turn and I’m starting to notice this and maybe it’s just a thing where that’s really kind of the amount of time it takes to become really good at something. And I think what’s unique about your story is that you did that while keeping a job. So I want to hear more about that tension, both, what kept you in the jobs and what kept you motivated to continue building this thing on the side?

Keshia M. White:
So with a lot of with the job stuff, so I felt I was really insecure, I guess, on my entrepreneurial or business building ability or, and I kind of thought it was maybe almost impossible to do, to be honest. I was like, “Oh, I really want to do it,” but at the same time, didn’t fully believe I could do it. I do feel like my efforts were kind of off and on, which is why it sucks a lot. I feel I didn’t really have to take that long, but since I wasn’t fully committed and fully believe in that it was possible, it slowed me down a lot. So, that definitely kept me in the job, just not believing in it, and then the fear, and then maybe, I guess, a little bit of the tension stuff, it depended on which, I don’t know, which [inaudible 00:17:29] I was in.

Keshia M. White:
I was pretty good. When I would be taking those classes at night, I would just kind of have all my stuff ready to go in the laptop and in the trunk and ready to drive off to class and go straight to class, when I was taking those design classes. And then even after that, if I wanted to work on my business on the side after work, I would, I did notice some nights if I would just come straight home and do it, I would be pretty tired and it would be hard to stay awake and get the work done. So what I started doing was taking my laptop to work and keeping it in the trunk at work, that way, instead of jumping into rush hour traffic to go home, I could just go to a coffee shop. It’s five or 10 minutes away from my office at work and just stay there to like eight o’clock.

Keshia M. White:
So I did that a lot. I would just be at some coffee shop downtown where I worked downtown and just stay there until like nighttime and then come home and eat dinner, chill, go to sleep. So by doing that, that may force me to be more productive until I got to the Infusionsoft job. When I was had that really aggressive quota and the commission was uncapped. I was like, I got to get this commission up. I went into full salesperson mode. They’re worried about my commission checks. So I did pretty much stop working on my business when I was there, but most of the time I was pretty consistent in the other jobs I had, so.

Josh Haynam:
Two things jump out at me from those two stories. One is the piece you mentioned about feeling insecure or afraid to make the jump. So I’m interested to hear more about what points along the way helped to assuage that fear or that insecurity to get you to the point where when the circumstances were right, you were ready to make the leap. And then the other thing that jumps out from talking about the Infusionsoft job is it sounds like there was always this untapped potential in your other jobs or this untapped side of you that wants to be a high achiever, but isn’t given the opportunity in the structures that you’re in, and so you always had this outlet where you could apply that energy, which was your side business, and then it’s interesting because when you got the opportunity to do that in work, it kind of, it sounds like it filled that potential, it filled that want or that need.

Josh Haynam:
So two separate things that I want to hear more about. One is the fear or the insecurity and how that slowly broke down, and then the other thing is what are your thoughts on that untapped potential idea?

Keshia M. White:
Yeah, well the fear piece first, so I feel I was still pretty much [inaudible 00:20:19] all the way up into my, I guess by the time I got to Infusionsoft, I was probably about 29 or 30 or so, and then I got the whole business idea maybe in my mid-twenties. So I pretty much had it that whole time because I feel a little bit of it too was, I was the only person that I even knew that wanted to work on a side business at the time, or maybe that bore with work where they cared to work on something else. Always felt I was the only one even cared about stuff like that. And it wasn’t until I got, so that environment at Infusionsoft that helped, because even some of the people there kind of had side businesses or some of the other employees did.

Keshia M. White:
And then we’ll maybe talk about stuff we had worked on before. So I didn’t feel I was the only person, the weird one. And then also just talking to those entrepreneurs every day, and a lot of times the way they would be talking, I felt I almost knew more about online marketing than they did, but somehow they were out doing it successfully. And I was like, “Whoa, you’re doing this with this level,” not to think I was better or anything, but just kind of hearing people’s level of knowledge because a lot of the job was educating people on online marketing strategies that they could be using to grow. And I knew a lot of it that they didn’t know, but they were still able to run businesses and do it well. And I was like, “Huh, I think I can do this, too.”

Keshia M. White:
So they kind of help pump up my confidence, but still, when I quit, I still was really, really fearful though. Oh, but then one more thing that kind of help break down the fear was that trip to Bali. So I had never been on an international trip before that and I didn’t have any friends go with me. I just met the people at the yoga because the girl who hosted it is she went to the college I went to, so I still follow her on Instagram, follow her yoga teacher journey, and I just met people when I went there. So basically I was flying across to Bali, my first international trip by myself, and I was kind of scared about that, but just successfully doing that though, and then tried doing little things there, getting on the Bali swing and being terrified and I’m scared of heights.

Keshia M. White:
So just little physical things that were scary kind of helped take away a lot of the mental fear that I had about quitting a job. I was like, “Well, you have money saved. So it’s not that big of a deal.” If I can fly across the world and fly across the jungle in a swing, I’m fine. I think I can do it. So I know that doesn’t have anything to do with business, but just conquering little fears that even our business fears kind of helps boost your confidence a little bit too, to push you out of your comfort zone a bit. But I was still scared though, when I quit, I definitely was. I was like, I’m just going to have to force myself to do it and just do it despite the fear. And then now things that seem scary back then aren’t even scary anymore. So you will have to at some point, just force yourself to do it even though you are scared, if you know you have the state, because you don’t want people to be reckless, but since I had the savings, I was okay.

Keshia M. White:
And then the other piece, the untapped potential. So, that was big, I forgot to mention that. So a lot of those, like I said, I really didn’t necessarily want to be in sales jobs, especially in that consumer product sales job, because we were literally talking about paper and hand soap. And so we would have these intense week long training just talking about the different types of the paper towels and the pencils and the toilet paper, and I’m like, “Is it that serious?” For us to talk about this stuff for an entire week. So, and then I had kind of had a little bit of a tech background. So the way my brain works, my brain can process stuff really fast, especially consumer products. That stuff is not that hard to think about. So I definitely felt too advanced in a way for that job, so like you said, after work, I would be looking at it as now I can use my brain. Once I leave work today and I can actually do some stuff that’ll challenge me mentally a little bit.

Keshia M. White:
And then, like I said, I’ve kind of tried to see if I could move into another department there and it didn’t end up working out. So maybe if that would have worked out, maybe I could have felt more challenged at work, but definitely when I got to the Infusionsoft job and we were kind of talking about a subject matter that I was interested in, which was online marketing and then I felt a little more challenged. Yeah, I was kind of more all in at that point with the job, so. Yup.

Josh Haynam:
Yeah, I think the piece on fear is interesting to me because it sounds like part of that process was building the muscle of being afraid and having examples where you try something that’s scary and nothing bad happens.

Keshia M. White:
Exactly. It’s like I didn’t die. Nobody died.

Josh Haynam:
Right. Right. And it kind of builds up this place to launch off from where you could reference those things and see, “Okay. Yeah, I tried this thing that was scary, it was okay. I tried this thing that was scary, it was okay.” Build up slowly, and then you’re able to make that big jump that was scary, and I think, the other thing that you said that really jumped out was seeing other people do it and that’s kind of, to get a little meta, that’s part of the idea of this podcast is hearing, and I think you and I can agree or maybe you can’t, we’ll see, but for me, I’m like, there’s nothing special about me.

Keshia M. White:
Yeah. Exactly.

Josh Haynam:
Anybody could do these things. I think the big part of the fear is just the mystery surrounding it.

Keshia M. White:
Exactly. It’s just so unknown.

Josh Haynam:
Right. And until you hear this is how it really happened, it just seems the people that do these things, somebody could look at you now, you’re making a full salary again, but you don’t have to exist within those structures that weren’t beneficial to you, which something that is very desirable. And I think to hear, “Well, this is how it actually happened.” Takes a lot of the fear out of it. And that’s amazing.

Keshia M. White:
Yeah. Yeah. Because I feel people can tend to put people that have already done it on this pedestal, “Oh wow. They must be so advanced.” And I’m like, I mean, I’m just figuring it out as I go and knowledge gaps, you fill those as you go because you’re never going to learn everything, so.

Josh Haynam:
Yeah! And I think the other thing that jumps out at me is it’s so common for the mentality amongst those who have quote-unquote made it to, and I’ve been guilty of this myself too, you can almost relish in like, “Yeah. It is basically impossible. I did it. So look how great I am.” But then I think you reach a point where you look at that and you realize, no, and it’s not a zero sum game either. There can be a thousand brand strategists, there can be a thousand startup founders and it doesn’t take away from your success and your achievements, and if anything, giving back is good for everyone.

Keshia M. White:
It is. Exactly. That’s why I try to be positive. I try to maybe sometimes mention in the hard work, but at sometimes I see some entrepreneurs who are so negative, “Oh, everybody isn’t made for this. Stay away. Keep your job.” I’m like, “Why are you?” Because even a girl told me that when I first quit my job. She was my photographer. When I first hired her, when I quit, and she was like, “Oh wow.” She was a full time photographer who I thought I would get inspired by once I got her to take my pictures, and she was just kind of so negative. “I tell people to keep their jobs. It’s so hard.” And I’m like, that’s a negative outlook, but I try not to be that person. I try to encourage and cheer people on instead.

Josh Haynam:
Ready. Yeah. I think, I mean, there’s probably so many reasons why you could be in that mind state and in reflecting on my own experiences, it’s probably at times where things don’t feel so good, but you almost have to make the leap in that sense, too. And the leap, the second leap, and there’s actually this book called The Second Mountain that literally talks about this where the second leap is actually deciding, okay, things have gone well for me. Now I’m going to decide that I want to give back, and I’m going to make the rest of my life about empowering other people, bringing other people up because I have climbed the mountain, now I want to go back down and be a Sherpa to guide other people up the mountain.

Keshia M. White:
Exactly. Yup.

Josh Haynam:
Well, thank you for sharing with us. This is really great to kind of hear, this is a unique perspective that we haven’t heard before on the show of somebody who stayed in it for seven years and use that energy on the side to build something up and then built up that resiliency to fear and then jumped off. So, that’s awesome. Appreciate you being open about that. If anybody wants to check out where you’re at now, follow your journey from this point forward, where can they go to kind of see where you’re at and follow you?

Keshia M. White:
Yeah. So you can find me everywhere on social media. It’s just my name, Keshia M. White. So I’ll spell it because there’s a lot of ways to spell my name, but it’s K-E-S-H-I-A and then M as in Michelle and then White W-H-I-T-E, so Keshia M. White on Instagram. My main place is Instagram. I do some LinkedIn too, and even a little Facebook. And then my website is also keshiamwhite.com, so.

Josh Haynam:
Awesome. Well, thank you so much, Keisha. We really appreciate you coming on.

Keshia M. White:
All right, thank you for having me.

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Josh Haynam

Josh Haynam is the co-founder of Interact, a place for creating beautiful and engaging quizzes that generate email leads. Outside of Interact Josh is an outdoor enthusiast, is very into health/fitness, and enjoys spending time with his community in San Francisco.

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