Practical Strategies for Building Businesses You Love with Jennie Blackwood

Josh Elledge (00:00): With us right now, it's Jennie Blackwood. Jennie, you are the CEO of Jennie Blackwood Coaching. You help women go from stuck to self-employed. And you're a business coach. It is great to have you, Jennie. Thank you for joining us.

Jennie Blackwood (00:13): Oh, it is my pleasure. Thanks for having me, Josh.

Josh Elledge (00:16): And so before we talk about your superpowers and the work that you do, you always love hearing what people do for fun when they're not at work. Tell me what you do for fun when you're looking to decompress.

Jennie Blackwood (00:26): I literally look forward to this probably multiple days a week, pouring myself an amazing glass of wine, sitting down after my kids go to sleep, and turning on whatever the latest and greatest trash reality TV is, and I just zone, baby. That's my happy place.

Josh Elledge (00:43): It is. They're real. Have you ever thought about it psychologically? Like what's going on? Like why is it so satisfying? Because I know exactly what you're talking about because we do the same thing.

Jennie Blackwood (00:53): I feel like it's just, you know, you can invest in other people's problems as opposed to focusing on your own. And it gives you like a rush to like get to know these characters and follow along and just be along for the crazy train. So that's why I'm dialing in.

Josh Elledge (01:08): Any particular shows this year that are memorable? They were like, that was a fun journey, and oh yeah. Yeah, did that scratch that itch? Anything come to mind?

Jennie Blackwood (01:20): How much time do you have, Josh? I love Love Island, Love Is Blind, Married at First Sight, and then my current guilty pleasure is The Ultimatum because it is really something.

Josh Elledge (01:29): What's The Ultimatum?

Jennie Blackwood (01:30): Oh, The Ultimatum is when these couples come on the show, one of the people in the couple has issued the ultimatum to the other that if you're not ready to get married now... but the thing is, is that they then go on with all these other people who have ultimatums and they start going into trial marriages with other people's partners and then decide at the end if they want to stay in their partnership or perhaps they have found a new love.

Josh Elledge (01:56): Oh my gosh. Okay, so my wife is a marriage and family therapist, and I cannot tell you that, you know, I don't know the who's or anything like that, but I hear generally about some of the, what's going on. But yeah, and the number of people who have potentially like blown up their primary relationship because of that, you know, that thing that they're after. And of course they go on the other side of the fence and they think it's going to be all great. And then reality sets in and they're like, that, maybe it wasn't the best move, right? It's always that, you know, grass is greener on the other side of the fence kind of thing. That is fascinating.

Jennie Blackwood (02:35): So it's called The Ultimatum. You got to tell your wife about it.

Josh Elledge (02:38): Okay. Yes. I think that's our next binge. Thank you, Jennie Blackwood. So Jennie, tell me about the work you do. Your website is jennieblackwood.com.

Jennie Blackwood (02:47): Yeah, so here's the thing. I got into this honestly completely by happenstance. I was at this point a stay-at-home mom. I was living off my husband's income, living the dream. I've been an entrepreneur for 11 years, but I had finally stepped out and decided that was my time to chill. So, unfortunately, he's an amazing real estate broker, but as the real estate industry crashed, so did our entire income. And so I was really put in this position where I was like, okay, I'm either going to have to get a new 9 to 5, which was for me like, put me in prison. I'd rather do that. I didn't want to go back to a cubicle life. So I decided to find something that could fuel our family, help contribute as he was starting to try and rebuild, but also where I could continue to be a mom first. So I started a charcuterie cart, a truck. Travel mobile charcuterie cart. And I thought, okay, this will get me out of the house. I'll get to go to fun events and I'll be contributing financially. But the crazy thing, Josh, is that that one moment, that decision that I made to push through... I was also, by the way, I had a toddler at home and pregnant at the time. Craziest time of my life. I was like, okay, I'm gonna start this cart. That has now turned into a 7-figure empire that instead of just being about events, I had all these women globally that were like, help me, how do I do this too? People craving transition, people wanting to get out of something that they didn't love, have more flexibility. And I now teach people how to start this same, what has evolved into a full-blown snack cart business, not just charcuterie, but how to transition, make crazy money with it, have the ultimate flexibility, and level what they do. And I coach people through that.

Josh Elledge (04:29): Yeah. Well, so it sounds great. It's almost interesting. It's kind of like the premise of a lot of reality TV shows, where you see someone that has just this amazing outside veneer, right, of what their life is like. But you know, and I know that as a business owner, yes, there are so many great aspects to it, and also there are a lot of realities, particularly I'd say in the early days, when you're just trying to navigate that, and it's very scary. So how do you? And I, you know, I tell people, you know, it's like entrepreneurs. Entrepreneurialism is... it is not for the weak of heart. Like, it, you know, take that concept if you couldn't kind of run with it and

Jennie Blackwood (05:16): Totally. It is something where, you know, like you said, people see the outside looking in and they just assume that everything came easily. It was handed over. It was just... it must have handed over on a silver platter. But that is so not the case. There are so many different things that you experience, the ups and the downs. I really feel like the people who end up winning the long game of entrepreneurship are those who are just as okay weathering the downs as they are okay to celebrate the wins. Not everybody can do that though, right? So for me, it was like, I was doing something brand new. I had never done this before, and so I had to do all the things under the sun to decide: Is this working? Is this not working? I had a billion iterations, and I had a lot of low moments, but I kept pushing through even when it was hard. Even when, by the way, when I started the snack cart myself, I worked my first event after like really a long trying to figure out how to start it up. And I had a baby 3 days later. So timing and things were not perfect, right? I had to start super messy, but I was just in my head of like, I can't give up on this because if I give on this, I'm giving up on my ultimate dream, which is starting something I can do that's my own, and again, where I can still be a mom first. But to your point, it can get ugly. It's not pretty all the time, and it's hard. But I feel like every time I've had those rough moments in building my business, I've only gotten growth, and it has only pushed me and made me better.

Josh Elledge (06:46): Well, Jennie, here we are in the middle of 2022, you know, kind of now in the second half of 2026. And so there are a lot of great resources that we have today that we didn't have in years past, one of them being AI-enabled tools. How are you incorporating AI into your work with your clients and your audience? And I think maybe a great way to say this is to my audience. What would you say to them?

Jennie Blackwood (07:13): Totally. Well, I've had many affairs with AI. I've started with ChatGPT, I've moved on to Claude, and now my new main squeeze is Viktor. If anybody has the opportunity to use Viktor in a Slack, if you use Slack, he is by far the best. But I'm gonna tell you something. For me, AI has become something where I used to say, hey, you know, why am I having this health symptom, to now I have fulfilled like an entire employee role with Viktor AI. So it's saving me time, it's saving me money. I've had him create... I call him him... I've had him create websites for me. I've had him create all kinds of different social media posts. He is actually now single-handedly running my entire Meta ads platform where all I do is send in the creative, quick publish, and I say, I need you to run this to this audience. I need to make sure that you're running it to this funnel. Please make sure the caption embraces all of these different things. And it literally goes into my Meta platform and completes it. Completely runs it all. Then it reports to me daily, here's what ads are working, here's what's not. I recommend pausing this. So it's almost like I've been able to take this machine, have it know my business and me like the inside out. And it is, again, it is performing employee roles, not just like mundane tasks at this point when it comes to my business.

Josh Elledge (08:36): Interesting. And so Viktor kind of made that... well, by the way, this segment is not sponsored by Viktor, but Viktor, if you want to reach out, I think we'd love to have you on the podcast. We're owed something here. Well, at least you are, Jennie.

Jennie Blackwood (08:48): You're welcome. Yes, no kidding.

Josh Elledge (08:51): And so, one more quick follow-up on that. So, but it integrates, so it integrates. So Claude has gotten really, really good at MCPs and APIs and that sort of thing. But then Viktor is just a little bit more tactical, kind of doing things, or more agentic?

Jennie Blackwood (09:09): So for me, when I think of Claude and the things I've dabbled in, I've liked graphic design and things that Claude's able to do there. But I also feel like memory lacks with Claude unless you're somebody who's like very good at adding all the different facets to Claude, which I'm not trying to waste my time becoming an AI programmer within my own pod, right? So I feel like Viktor, it's funny, he's not as instantaneous as maybe the others, but the production is unbelievably next level. So yeah, I mean, it's... I'll even have it create full-blown documents. I can send it to other teammates and say, hey, send this to Brandy, who's my assistant, make sure she's following up on this, make sure she's integrating this. And I just feel like I... again, I keep saying this, but it feels more like an employee than just like a task function, if that makes sense. So it's completely changed the game for me. I am saving thousands because of it, and it's just, it's more of what I want, as opposed to like contractors trying to fulfill a whole bunch of different facets of my business. It's all in one.

Josh Elledge (10:10): Love it. Great. All right, Viktor, you're welcome. So moving on. So, you're... when you are working with someone, and they have a business idea, validation is just so critical. I think that often when we post on social media, it's really easy to get a lot of social support, because people don't want to make you feel bad or look bad in front of your friends or whatever. And then similarly, I think AI does a terrible job of validating every single stupid idea that you might think to... and I've seen some real stinkers. I'm like, you know, and it's told me, oh yeah, you should totally turn that into business. I'm like, are you high? Like, there's no... no one's gonna buy that. And dear God, if I wasn't as ex... you know, if I didn't have the decades of doing this, I could have easily been led on a wild goose chase that would have wasted so much time, effort, and money. And I feel badly that people are pursuing bad business ideas because AI or social media friends who also don't have experience in this are saying, yeah, you should totally do that. How do we figure out what we should be doing? Because you came up with a great idea with that charcuterie cart, but not everyone can do that.

Jennie Blackwood (11:34): You know, I think AI has a place. I think it can be inspiring. I think it can be all those things. But as far as myself as a business coach, there is a lot of things that a human can offer to people when they're trying to start a business or, you know, find a new path that AI cannot. And so I think we have to understand that while it can fill in gaps, it is not the end-all be-all. You still need human life within plans, purposes, trainings, because that's where you're getting real experience. And to your point, Josh, yeah, it's funny. You can actually tell AI that you don't want it to be so happy all the time, and it can be more tough love sounding and those things, but you have to have somebody who's going to give you a better lens when it comes to ideas and people. Go to the people that are experienced in whatever it is that you're hoping to start, get better at. Go to somebody who is like an idol for you in that realm. Go straight to the sauce, right? Get it from them.

Josh Elledge (12:33): Yeah, so that's going to help a lot. You know, obviously, again, talking with someone that's got some wisdom and experience, has, you know, a trail of, you know, blood from their bloody noses. They've got their punch, you know, nose punched in, you know, because again, it's a lot of ups and downs in that journey. And speaking of which, you know, I know this kind of like, you know, kind of once you get it going and maybe you kind of release it into the wild, you know, I hear about this, you know, concept of messy middle, right? Where it's now, you know, we get all excited about we're going to do this thing, then we launch it, and then crickets. So if someone is in that phase right now and they're like, I have a great idea, I'm really good at it. I think it's going to provide a lot of value for people, but I can't get any customers and I don't want to be low-key selling on social media to my high school, you know, people I went to high school with and stuff like that. That's kind of lame. Like, I don't want to be a spammer, but yet I want to be able to do what I do. How do you help them figure that out? That part out?

Jennie Blackwood (13:34): You know, I say to everybody that I work with, whether it's with the charcuterie business or with my higher entrepreneurial business coaching called the Why Not You Method, your business is nothing without great marketing, right? Marketing is the breath of your business, and you can check all the boxes, you can start it up, you can create the pages on social media, but if you don't know how to deploy the tactics that are actually going to get you seen, it is going to be crickets. And so understanding that there's going to be a learning curve and, you know, do you want to go sit on YouTube and try to figure it all out? Or do you want to go to a business coach that can say, hey, here's how I put myself at the top, right? These are the things that are working today, and then help you. It's like going to school. You know, you're starting a business. How nice would it be to get to go to school for something that you also want to become good at and successful at? So I think marketing is life when it comes to your business, so understanding how to find the right resources or the right people. Oops, did I lose you, Josh? Sorry, the right resources or the right people. That is going to be everything in helping you get your business off the ground.

Josh Elledge (14:38): Yeah, Jennie, your website is jennieblackwood.com, and by the way, that's Jennie with an IE, very important in the pronunciation. I'm married to a Jenny with a Y, so you get it.

Jennie Blackwood (14:49): Yes, yep.

Josh Elledge (14:51): And not a Jennifer or

Jennie Blackwood (14:53): No, I am neither. I've tried to rebrand as Jen a couple of times, just not working out. So here we are, Jennie with an IE.

Josh Elledge (15:03): [unclear] your website, what would you recommend that they do? What are their next steps here?

Jennie Blackwood (15:07): Yeah, so I got a couple different opportunities for you. If you're looking for something that you can start quickly, that's like a great side hustle or something that can turn into something that's a 6-figure business, I would talk to you about my snack cart options because it really is something that's so low cost to start. The margins are amazing. And it's like no overhead, seriously. But then there's also a way to find me where I was talking about the Why Not You Method, where this is for entrepreneurs that have something that's an idea outside of the snack cart system, where I can bring you in and teach you how I scaled a small idea into being a 7-figure business through systems, operations, and marketing. And I am here to give you that exact model because I have seen it work for myself. I can help you too.

Josh Elledge (15:51): Very cool. By the way, I want to give a shout out to Jennie, to your podcast, and that is called Girl, Why Not You?

Jennie Blackwood (15:58): Exactly.

Josh Elledge (15:59): Jennie Blackwood. So we have a link, direct link to your podcast as well, which I love. I also... your Insta is very cool. It's very [unclear]. So if you want to see the snack carts and see the great work, it's interesting seeing which of my friends are following you. And I'm like, yeah, I can see that. So yeah, you have nearly 150,000 followers there. But you have some great posts that I think are quite inspiring. So Jennie Blackwood, thank you so much for joining us again. Your podcast, Girl, Why Not You? I just... every time I see it, I want to pronounce, I want to say it in a kind of a sentence form. Your website, jennieblackwood.com. Jennie, thank you so much for all of your insights and sharing these thoughts with us.

Jennie Blackwood (16:52): Thank you. I loved being here and I hope that I helped even just one person listening today.