Business Bites Podcast Episode 100: My Entrepreneurial Journey

My Entrepreneurial Journey

Episode 100 on the Business Bites Podcast

The Gist Of This Episode: This episode is a celebration of 100 episodes and a full view into Rachel’s entrepreneurial journey from waitress, to unpaid intern to headlining conferences and topping podcast charts. While that sounds impressive, this episode is actually more about the real life stuff that happens and how you can fit your entrepreneurial “success” into it.


What you will learn:

  • How Rachel’s brands weren’t built in a day but rather over 15 years of hard work
  • Advice for when you are feeling burned out
  • How she was able to build a business with very little money and then turn that into multiple brands
  • What her biggest lesson learned during her entrepreneurial journey is
  • and more!

Expand To Read Episode Transcripts

I cannot believe that we have reached episode 100 of the Business Bites Podcast. In fact, maybe now it’s time we can start calling myself a podcaster. I’ve kind of shied away from that not because I don’t like podcasting. I’m obsessed with podcasts, mostly true crime, but I just really see podcasting in the Business Bites as more of a tool in the toolbox of what I offer to all of you, but man, things are starting to get serious and we’re at episode 100.

I want to share in this episode about my journey. I get asked a lot about my entrepreneurship journey and I’ve done tons of interviews, gone on other people’s podcasts, webinars, speaking stuff, but I never really boiled it down to one place. So this may be a little less educational, but more about the trajectory of my business. I will still throw out some quick business tips as always and let’s just … I don’t even know where to start. I guess we’ll start at the beginning.

Hey guys, welcome to the Business Bites Podcast. I am your host, Rachel Brenke, and this is episode 100. As always, you guys can find all show notes at We are here. We’ve done 100 episodes of myself and with guests for quick bites of content for you guys, busy entrepreneurs who are just trying to make a go at it. Many of you are killing it. I love hearing from you. I see this stuff in the Business Bites Facebook group. I get PMs from you guys all the time, PMs, DMs, whatevs, on Instagram, and one of the top questions y’all have asked me over the years of doing this is, how did I get here?
Well, first, let’s preface this episode to say here is not the edge. Here is not the pinnacle of where I want to be. As you figured out, I’m multi-passionate, ever-evolving, ever-growing, like many of you are, and I’m just going to keep doing this thing. I love it. I love being able to … even though I’m talking to myself, sitting in the office now to talk to you guys here, I feel like I am reaching out and touching and making a difference, and that has been my primary goal of this entire journey, and it’s really fun. Some days it can be very frustrating thinking that I’m getting lost in the noise. There’s so much out there, as you’re going to see as I share in chronological order of how I got to where I’m at and where I plan to go.
But the noise has kicked up so much in the last few years and it can be very disheartening, and I share that. As you guys know, I like to share my heart. I’m very transparent. And don’t look at somebody who’s at a 100 episodes, top podcasts on Apple and think, “Oh, they made it. They don’t have struggles.” Yeah, maybe a little easier than it was in the beginning, some days. Some days it’s not. There are some things that are much more difficult, especially when you do put yourself out there to the world, which we’ll get to that in the episode now.

Where do I start? I guess at the very beginning. The very beginning is a good place to start. Bonus points if you know what that is from. Sound of Music, by the way. All right, so way back in the day before internet … well, not necessarily but pretty close. In fact, I was the tender age of actually middle school, elementary. This is where it starts. I promise it won’t be so long-winded, but I remember I never really fit into the box. And in fact my second child … I have five … My second child right now is my daughter. She’s very much like me and we’re struggling with some of the same issues that I had when I was younger and it was being super analytical, and I remember telling my teachers ways that they could change their filing system and their grading system and how they could organize, how to hand out homework and that wasn’t well-received in school, but I knew then that I never really was going to fit into the box and I always wanted to seek to improve things.
And so fast forward to the tender age of 19, 20, met my husband. I was in college at University of Texas. My husband was active duty Army, had already completed one tour to Iraq, and met him and it was a whirlwind romance. We got married very quickly, very young as you probably have heard a lot of military couples do, and spoiler, it’s been 15 years now. We’re still together, five more kids later, three more dogs. But at that time, I was still in college and I already knew that I wanted to go into business of some sort. Wasn’t sure what. Was still kind of dabbling with this idea of, I love crime stuff. I’m obsessed with crime podcasts, like Sinisterhood is one of my absolute favorite.
So I was going to school for criminology and criminal justice and I hadn’t really truly matured. One of the benefits, and I do admittedly put this out there, is that I had the resources to go to college, and school did kind of come easy to me and still kind of does, too. I think that’s just someone that’s super analytical. I can read something, I scrutinize and I’m able to develop a good argument. Now, throw math and science at me, that’s not happening, pull out my calculator, that kind of thing. But when it came to history, English and all of that, did very well.
A really good time, fairly average, I guess, in undergrad, and we got married and had our son, our oldest. And then I was like, “You know what? I really don’t know what I want to do. I’m obviously going to try to finish undergrad and I need to work.” So I was waiting tables and I also did a brief stint at a bank. Really wasn’t my thing, sitting at the counter trying to sell bank accounts to soldiers, and so I ended up going back to waiting tables, which I had done in high school. And what’s funny, I’ve probably mentioned it on a couple of episodes, I definitely found that waiting tables has immensely taught me a lot about running a business, immensely a lot about customer service, client psychology, all of that, because you run into a variety of people.
The more efficient that you work, the more money you can make. You get people in, you get people out, but not make them rush. And so I was waiting tables, but about that time was also when I was diagnosed with cancer, thyroid cancer. And I remember sitting there. I got the phone call. They didn’t bring me in, actually, the Army. That’s the way they roll. They just called me and the scheduler was like, “Hey, we’re going to take your tumor out.” And I was like, “Say what?”

But I remember distinctly sitting there, and this was before iPhone, so mind you when I say it was before the internet, Facebook was not even around. Maybe it was on the cusp. I think Zuckerberg may have had the idea, was hammering it out, but it was nothing compared to what we know now. MySpace was kind of a thing, and this is where I learned to code, so I do all my own websites, and this is where I learned to do some coding stuff with the glittery backgrounds and the auto-play music. Super fun. But I remember sitting there and looking at my son who was a year and a half, if that, two, and thinking, “If I make it through this, I don’t want to work for someone else’s dreams and goals. I want to work for mine and I want to be as present for my kid slash kids.” I didn’t know if I’d have any more, didn’t really intend on having a big family. Spoiler, we have five.
I just distinctly remember that feeling. And so all those feelings, it kind of came back from when I was criticizing my teachers of how to change things. And that’s when I really dug into learning about business. Remember, this was during the time when this freemium model where you can log onto blogs and get business insights, podcasts, all that, they were not super prevalent. They’re not nearly what it is now. I dug into learning about business. At the same time, I was also starting up my own online apparel shop. I did a little dabbling in graphic design on Gimp. Oh, awful. But I did it and I was making money and I was putting all the money … and when I say making money, we’re talking like two nickels to rub together.
So a lot, what I was doing in order to save money, school, online as much as I could during the day to be with our son, worked on the business while he napped, and then in the evenings I was waiting tables, and my husband was enlisted. We did not have a lot of funds. We were bankrolling everything ourselves, which is the story of many people. And thankfully, we had healthcare through the Army so we didn’t have to worry about that too much, but we were putting all the money that we could … of course, not taking away from my family, but any extra money that I had, picked up extra shifts waiting tables, longer hours … I put that all into the business, into this apparel and learning of business.
Fast forwarding a bit through this, people started asking me questions about business. They saw that I was doing decently well with the side hustle, this apparel shop, and they wanted to know how they could get in to do this. And again, there was not the freemium model, so you couldn’t just log online really and get the info. And this is really where I started doing a lot of my blogging. I also decided to go to school and get my MBA. During this time, husband was in and out, deployed to Iraq and was working full-time.
I did some time as a government contractor to kind of help pay for the MBA thinking that a business degree had to be the way, because that’s the old school way, right? Had to be the way that I was going to become a successful business owner. I’ll tell you guys what. Now things kind of make sense, but at the same time, honestly, if you don’t have a business degree that’s a-okay. You don’t need to go to business school in order to learn how to run a business. Just doing it and getting to know other people, listening to podcasts like this are definitely the way that you can go about it.
So fast forwarding a few years, I’m trucking along, I’m doing a lot of the blogging, getting to know other people, I’m sharing about how to run a business, and this kind of included the setting up and legal aspect of stuff. And I realized, “There’s something here. So let me see about law school.” And law school also came about because we had dealt with secondary infertility as a result of my radiation treatments and surgeries from cancer. That’s why there’s a four and a half year age difference between my first and second, son and daughter.
And it’s funny because we had just decided we weren’t going to do any more treatments, weren’t getting pregnant. I had been accepted to law school since I was really interested in business and I also still had that criminology degree, so I like criminal stuff, so maybe entertain that thought a little bit. And literally the day after I paid my deposit for law school, we found out we were pregnant with our daughter without any treatment. And so that was incredible.
I still went to law school. I had her the first year. Husband was deployed or gone to training and then was deployed my second year. And then third year actually, we got pregnant for the third year, so that was number three. And this entire time, I’m still trying to help people run their businesses. I’m learning how to run business on my own. I’m doing blogging, and I set up one of my most prominent brands, The Law Tog, because I had also started offering photography services to some of my business consulting, and admittedly … I’ve never shied away from this … admittedly was using photography A, as a way to be creative and balance my brain from law school, but also so that I could make money because we had gone during this time from being a two income to one household to two household because he was away at training and had to pay there and did geo bacheloring for military spouses for a while.
So anyways, finances were tight, and you’re not supposed to work during law school, especially your first year, but I was continuing the business consulting and stuff. And so yeah, I kept trucking along, started getting the blogging going. The Law Tog got going and it took off. It is the legal resource for photographers. A lot of the info like you guys get here is over there as well. It’s thriving. It’s amazing.
And I decided, hey, when I exited law school, passed the Texas bar, I also had the Virginia bar, I was like, “You know what? There’s something here. Even though we’re starting to spin up in the online sphere of all this freemium information, there’s not a lot of people sharing about legalities from the context of being an entrepreneur and doing it yourself,” because I was running my own apparel business doing photography, I was doing consulting.
And so as an entrepreneur myself, I understood what a lot of entrepreneurs were going through, but I was also able, with the education, the licensing and the experience, to combine it all together, and that’s where a lot of the brands that you see now, The Law Tog for photographers … Fit Legally comes a little later once I started getting active and fit and stuff, and then The Business Bites under Rachel Brenke, which is me, and ended up adding a couple more kids as a total of five to the family, and I’ve just continued to grow and done multiple income streams.
We’ve owned a coworking space, the apparel online store, some investing in some other companies, silent investors, and it’s just been a really good way and trajectory. But I’ll tell you what.

It’s not always easy. And I’m not saying this from a place of like, “Oh, woe is me. It’s always hard.” Anytime you start a new brand, you may have some leverage because you already kind of workflows and processes and I kind of copied and pasted over workflows, processes and approaches from one to another. But definitely, when you start new, you’re starting new.
And I still look fondly back at when I was really spinning up my core businesses that are still my core businesses now, but I really do kind of miss that baptism by fire. I mean, I remember sitting in my office during law school. I was tired, school all day. I was pregnant, had Joshua that first year, and I had all this studying to do and I still had to respond to all my clients and everything. And I remember I was just so burned out. I was so tired. Husband was deployed. So there was that stress, and it forced me to get my ish together. It forced me to find workflows and processes that work better.
And I encourage all of you, especially if you’re feeling overwhelmed and burnt out … and I still use this today. If I start feeling stressed out and burned out, I often always look and ask myself, “What are you doing that’s inefficient here? Could you offload some of this? Do you need to be doing all of this?” That’s another question, too, that I think as entrepreneurs we definitely are all out. We’re all in. We got to do it all, and you just have to ask yourself, is the client really going to care if you answer it at 11:52 PM or if you answered at 6:30 AM when you wake up? The reality, are they going to care about the seven hour difference?
And it’s little things like that … excuse me … that I learned through all of this. And when I got into my 30s, I was having baby number five about that time. After the cancer, I had struggled with a lot of weight. I had struggled with some postpartum depression. It did impact my businesses, and it was just kind of an alignment of success trajectory for some of the brands was going high. It went quicker than I realized and I couldn’t keep up along with self-esteem. It’s the same story that many of you guys approached it.
Getting through that, I entered into a triathlon, and many of you have probably seen where that’s transpired. I’ve now gone into running in triathlon. I’m on Team USA for two seasons, and then I also did Ironman World Championships the year before last, and so it’s been an incredible journey, not just professionally. I think that’s one of the things that we miss a lot when we hear interviews is where people have come from. It’s so easy to look at the chapter right then or the last few years, but not really understanding where the seeds of the ideas … I remember it in elementary school thinking, “I just want to fix and make things better,” right?
And that’s impacting other people, which actually, this is a good time for me to bring in that I struggled for a long time with this idea of, “Am I going to go into the for profit sector and is that selfish?” because one of the things that I always thought in the back of my mind of improving, I always wanted to help impact others. That’s why I even got into doing the business consulting and stuff at first it’s because I was thinking, “I’m at home with my son. I would love for other moms or parents to be able to do the same.”

I struggled for a long time, especially because there was a hot bit going into law school in the first year, I really thought, “You know what? Let me use my criminology degree.” I really had a heart for prosecuting child sex crimes and I struggled for quite a while of admitting that I “followed the money” and it wasn’t because I followed money because I was greedy. My family needed it at the time. Husband was still active duty, and I was going to spend the same amount of money for daycare that I was going to be making as a prosecutor, and so I turned down the prosecutor position, and that was really hard and I never really publicly shared that. I’ve really never fleshed that out in an interview before.
Now, I share all that to say you can make an impact and it’s okay if it’s in a for-profit type sector like this, because for me, I’m putting out a lot of free information that yeah, the end result and the end goal kind of is to get people to buy into who I am, get to know me and potentially pay me money, but guess what? The benefits are in there. I’m still impacting. Even on this episode, I hope that it impacts just one person. It’d be great if it was a lot more because we have a lot of great listeners, but I definitely want to impact at least one person.
And it took me a while to realize that you can make good in the world, you can make an impact in the world, and it doesn’t have to be being the stellar prosecutor or locking up … I was going to say perverts, but it’s true … people that commit child sex crimes. I could still make an impact, and I feel like I’m helping make a ground floor impact by allowing for families to have more financial freedom, be more present for each other as partners, as for their kids, and you don’t even have to be in that kind of familial structure. It could be anybody who at all that wants to have a quality of life.
That was one of the big things that my dad has always taught me is he would rather take a cut in pay for better quality of life. And I took the route of, “Well, rationally, does it make sense to go only make 40,000 a year and pay 40,000 in childcare and make zero? Then what’s the point in me missing my kids?” to taking the risk of being an entrepreneur. And many of you have taken that. If you’re listening to this, you have taken that step, and kudos to you because there definitely is … Even though I may be making more now than I’d ever have made as a prosecutor, there was a lot of risk and there was a lot of long hours I wouldn’t necessarily have had. You see the trade off with this, right? You can get a quality of life. You just may be trading off different things.
So with all of that, where I’m situated now is I’m still active in triathlons. I’m actually currently pursuing all the major marathons. I have London coming up. That’s just my personal side, and continuing to do speaking engagements. I have done international, some of the biggest in America. I absolutely love it. I used to be terrified of public speaking, so this job has kind of forced me to be able to get better at that. And I also own a law firm. That sprung up.
I’d always been doing, since I graduated law school, I was continuing my regular businesses that I’ve outlined, but I was also doing legal work. It just wasn’t probably one of the primaries. It was just a fringe benefit, a peripheral thing to everything else. And then once it really started spinning up, I was able to shift a lot more time away from more of the … because now on these brands have gotten to more of a passive income even though they still require you to keep the ball rolling. The big boulder has already been rolling and it’s easier just to do little taps since I can focus on legal stuff. And so I did it all for a while by myself, and that was fun. And then I got a partner and we’ve been doing partner style work for officially two years, but basically three years, and he is now going to be teaching full-time at the law school and I’m going back out on my own, and the entire staff is going with me and I’m thrilled with that.

Now I’m really in a place that I feel like I can serve you guys even better. I really have an understanding of who I am as a person, who I am as an entrepreneur or the values that I want to inject to my clients, and so the path trajectory doesn’t have to be what everyone else says. You don’t have to work the nine to five. I waited tables. That was the grit and what I needed to do. We sold items that we were not using anymore and stuff around the house in garage sales to put money into build a business. You can make it happen. It doesn’t have to be a trajectory that everyone wants you to conform to. It’s going to be up and down. As long as you continue moving ahead, as cliche as that sounds, is what is most important.
So there’s a lot in there actually that I did not share, but that’s really been the general journey that I’ve taken. I think just as a recap on that, started out just wanting to help others and to improve things and work for myself. From a more tangible business standpoint, something that I’ve realized is you can think of it like Monopoly. This is all a board. I’ve got my Park Place or whatever. It’s the only thing I could think of, and I’ve built my hotel. Once I’ve built that hotel to where it’s pretty sustainable and I can develop a team to help maintain it and it doesn’t require 100% attention, take what you learn from that, copy and paste it over. I mentioned that earlier. And so that is what I’ve done.
I mean, if you look at the brands, it’s nothing novel. It’s nothing new. I’ve just taken a new spin. I identified something in the market that needed done. And then with each brand, it’s relatively the same structure. It’s all about the messaging and who I’m serving. And so think about that. Maybe you’re thinking, “Oh, there’s more people I want to serve.” You know what? You can serve people in multiple silos, multiple hotels, multiple industries.
You can build it up, and again, understand that if you’re coming in and just meeting me, you’re just seeing things on like year 15. You’re not seeing things from the very beginning. It’s not that easy. You have to really be intentional about creating what you’re doing, checking analytics, always evaluating … I talk about this formula a lot on this podcast … about who you’re trying to serve and what your unique selling proposition is for that and that really is, if there has to be a magic formula, that’s the formula.
Always keeping yourself in check is the most important thing of this entire journey that I have learned is that … It is so cliche, we can just post a little pin board here … but if you’re not staying true to you, if you’re becoming overloaded, if you become bombarded, you’re not happy with what you’re posting or what you’re doing and you dread doing it, make a daggone change because you’re losing time and money when you’re not making the change. I know it’s more of a risk. You think, “Man, well, I’m getting some income. I’m making a couple thousand a month. If I make a change, I’m going to lose that.” But guess what? You’re going to lose more over time.

Let’s say if you’re still sitting here a year from now and you hadn’t made the change, you’re going to lose all that potential money you could have made had you made the change because you’d be more effective in whatever it is that you like doing and what you are good at doing, because I was resistant for a long time, and adding on extra brands, I thought, “If I leave The Law Tog,” not leave it, but, “If I take my eyes off of it, it’s going to falter.” But you know what? It doesn’t. It gets to a point, and if you at least, you got that big boulder, in the beginning, it’s hard to get that big boulder rolling. But once it’s rolling, you have the processes and all the lessons in place, you can just keep tapping it along. I can then look over and start pushing another boulder, but keep one hand just tapping this one.
And I think that’s the biggest takeaway from my entire journey and what I kind of have learned personally and professionally is to keep myself in check, make sure that I’m within my limits, because I’m also one of those people that doesn’t like to be put in a box. I don’t like having limits, but we all have limits, recognizing and understanding that and knowing that it’s also different. The grit and the sweat and blood that you’re going to have to put in at the beginning is going to be different than the grit and the blood and the sweat that you’re going to put in later when you’re further along on the journey.
Now, I think I’ve thrown out enough of cliches for you guys, but that’s my journey into a nutshell. I’m more than happy to answer any questions or anything about this. This is very super high level. I could talk for hours about all the lessons I’ve learned about all the different jobs and that I had about working for free, because I do talk about that a couple of episodes, paying your dues, about putting yourself out there. If you have any questions, please feel free to reach out, and thank you to each of you for helping us get to episode 100.

Hi, I’m Rachel Brenke

Rachel Brenke

As a mom, team USA athlete and cancer-survivor, I want a real life while I have a real business.  This is why my resources don’t promote hustle-culture, rather tough-love and no-holds-barred tips to achieving both.  In addition to this website, I have a top-ranked business podcast, been featured in places like Forbes and work 1:1 with so many of you.

Enough about me though. I am proud of you for pursuing entrepreneurship. It is rewarding and amazing.  Keep at it!

Now enrolling: RealBiz Accelerator[GET INFO]
+ +