2486 - Practical Strategies for Building Businesses You Love with Jennie Blackwood

Scaling Past the Messy Middle: Seven-Figure Business Blueprints, AI Workflows, and Human-Centric Coaching with Jennie Blackwood Coaching's Jennie Blackwood In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Jennie Blackwood, CEO of Jennie Blackwood Coaching https://www.jennieblackwood.com, to unpack the operational mechanics required to transition a early-stage venture into a seven-figure enterprise. Jennie, a seasoned business builder, podcast host, and growth coach, shares her strategic journey from launching a mobile charcuterie business to building a multi-stream coaching organization. This conversation delivers an actionable operational guide for founders, agency leaders, and emerging entrepreneurs who want to navigate early growth bottlenecks, integrate artificial intelligence into daily workflows, validate market demand, and deploy high-converting marketing systems. The Scaling Infrastructure: Integrating AI Workflows, Real-World Validation, and Human MentorshipThe primary operational hurdle stalling early-stage founders during rapid scaling is navigating the friction of the "messy middle"—the phase where initial enthusiasm gives way to complex operational demands, marketing volatility, and burnout. Jennie Blackwood explains that building a resilient enterprise requires replacing perfectionism with rapid execution, launching minimum viable products, and gathering direct feedback from paying customers rather than relying on vanity metrics or social media likes. While AI software engines can accelerate content creation, manage Meta advertising campaigns, and build landing pages, early-stage founders must distinguish between tactical automation and strategic direction. Relying solely on automated tools without human mentorship often leads to misaligned marketing; experienced coaches provide the necessary accountability, contextual feedback, and strategic course correction to keep businesses moving forward. Maximizing operational efficiency in a scaling company requires treating advanced artificial intelligence not as a passive tool, but as an integrated member of the core team. Incorporating specialized AI platforms across daily workflows—such as automating digital ad campaigns, streamlining social content scheduling, and managing graphic assets—allows founders to cut thousand of dollars in administrative overhead while maintaining continuous output. Integrating these AI systems directly into primary communication channels like Slack enables real-time task reporting and performance updates without pulling leadership away from high-stakes decision-making. By delegating repetitive backend logistics to automated software, business owners clear the cognitive bandwidth required to focus on offer positioning, client retention, and long-term enterprise growth. Furthermore, sustaining a profitable growth trajectory demands that corporate leadership view strategic marketing as the non-negotiable driver of overall business viability. A superior product or service yields zero enterprise value if it lacks a consistent, scalable system for acquiring new customers. Business owners must move past relying on informal networks of friends and family, investing instead in modern customer acquisition channels, social proof documentation, and automated sales pipelines. Systematizing lead generation early ensures that the business generates predictable cash flow while remaining aligned with the founder's personal lifestyle and financial goals. When clear market validation, integrated AI workflows, disciplined marketing execution, and experienced human coaching are synthesized into a single business architecture, founders eliminate operational bottlenecks, protect profit margins, and predictably scale enterprise valuation. About Jennie BlackwoodJennie Blackwood is the Chief Executive Officer of Jennie Blackwood Coaching, host of the Girl, Why Not You? podcast, and an expert business growth strategist. Drawing from a personal journey scaling multiple successful ventures—including a high-margin mobile charcuterie brand and a seven-figure coaching enterprise—Jennie specializes in helping entrepreneurs navigate the operational complexities of business growth. She is a recognized mentor focused on empowering founders to leverage AI automation, build scalable marketing engines, and design profitable businesses aligned with their personal values. About Jennie Blackwood CoachingJennie Blackwood Coaching https://www.jennieblackwood.com is an elite business advisory firm and coaching practice engineered to help emerging entrepreneurs and business owners scale past operational bottlenecks. The firm specializes in delivering comprehensive business validation frameworks, AI workflow integration, high-converting marketing playbooks, and structured coaching through the signature "Why Not You" methodology. Through practical execution blueprints and community mentorship, Jennie Blackwood Coaching enables founders to eliminate administrative debt, build high-performing systems, and maximize enterprise equity. Links Mentioned in This EpisodeJennie Blackwood Coaching Official Website: jennieblackwood.com https://www.jennieblackwood.comJennie Blackwood on LinkedIn: linkedin.com/in/jennie-blackwood https://www.linkedin.com/in/jennie-blackwood-10017b298/ Key Episode HighlightsNavigating the Messy Middle of Scaling: Embracing imperfect action and grit to push past early operational friction and build a resilient business. Human Mentorship vs. Automated Software: Combining AI efficiency with human coaching to receive accountability and high-level strategic direction. Integrating AI as an Operational Team Member: Utilizing specialized AI engines inside Slack to manage web assets, ad campaigns, and content scheduling. Real-World Offer Validation: Moving past vanity social metrics to test market demand with real-world pilot programs and paying clients. Building Scalable Marketing Engines: Systematizing client acquisition to move beyond personal networks and build predictable revenue pipelines. ConclusionThe conversation with Jennie Blackwood reinforces that transforming an early-stage venture into a seven-figure enterprise requires a balance of modern technology, strategic marketing, and experienced guidance. By standardizing internal business systems, deploying AI for administrative execution, and maintaining a relentless focus on customer acquisition, business leaders can build a highly profitable, self-sustaining growth engine. More from The Thoughtful Entrepreneur🎙️ Want to be featured on The Thoughtful Entrepreneur? Get your voice in front of 50K+ listeners. 👉 Schedule your guest spot here » https://go.upmyinfluence.com/podcast-guest 🤝 Consultant doing 6+ figures? Let’s introduce you to your next big client, partner, or referral source. 👉 See how here » https://upmyinfluence.com 📡 Thinking of launching your own podcast? We’ve built over 250 shows for leaders who land dream guests weekly. 👉 See the system here » https://upmyinfluence.com 🚨 What’s Your PodVerified Score? 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• 0:03Speaker 00

  Welcome to The Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15 minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free pod verified score, free pod verified guest training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests

• 0:44Speaker 00

  thrive and grow in podcasting. Visit pod verified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it.

• 0:55Speaker 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.

• 1:09Speaker 01

  Oh, it is my pleasure. Thanks for having me, Josh.

• 1:11Speaker 00

  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.

• 1:25Speaker 01

  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, that's my happy place.

• 1:41Speaker 00

  It is, it is. Have you ever thought about it psychologically? Like what's going on? Like, why is it so satisfying? Cause I know exactly what you're talking about, because we did the same thing.

• 1:52Speaker 01

  I feel like it's just, you know, you, you can invest in other people's problems.

• 1:57Speaker 00

  Yes.

• 1:57Speaker 01

  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, that's why I'm dialing it.

• 2:07Speaker 00

  Any, any particular shows this year that are memorable? They were like, that was a fun journey. And oh yeah, did that scratch that itch?

• 2:17Speaker 01

  Well, how much, 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.

• 2:29Speaker 00

  What's the ultimatum?

• 2:31Speaker 01

  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.

• 2:54Speaker 00

  Oh my gosh. Okay. So my wife is a marriage and family therapist. And I cannot tell you, 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, 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 like, eh, that maybe wasn't the best move, right? It's always that day, you know, grass is greener on the other side of the fence kind of thing. That is fascinating. So it's called the ultimatum.

• 3:33Speaker 01

  You gotta tell your wife about it.

• 3:34Speaker 00

  Yes, yes, yes.

• 3:35Speaker 01

  She's gonna be all in. Oh, hands on.

• 3:36Speaker 00

  I think that's our night. 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.

• 3:45Speaker 01

  Yeah. So here's the thing. I, 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 nine to five, 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

• 4:27Speaker 01

  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 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 going to start this cart. That has now turned into a seven 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

• 5:11Speaker 01

  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 love what they do. And I coach people through that.

• 5:27Speaker 00

  Yeah. Well, um, so it sounds great. It's almost interesting. It's, 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, it's like entrepreneurialism is, it is, it is not for the weak of heart. Like, you know, take, take that concept if you couldn't kind of run with it.

• 6:13Speaker 01

  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, 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.

• 6:55Speaker 01

  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 three 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, 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,

• 7:38Speaker 01

  I've only gotten growth and it has only pushed me and made me better.

• 7:44Speaker 00

  Well, Jennie, here we are in the middle of 2020, 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?

• 8:11Speaker 01

  Totally. Well, the, I've had many affairs with AI. I've started with chat GPT. I've moved on to Claude and now my new main squeeze is Victor. If anybody has the opportunity to use Victor in a Slack, if you use Slack, he is by far the best. But I'm going to 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 Victor AI. So it's saving me time. It's saving me money. I've had him create, I called him, I've had him create websites for me. I've had him create all kinds of different social media posts.

• 8:52Speaker 01

  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 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.

• 9:35Speaker 00

  Interesting. And so Victor kind of made that, well, by the way, this segment is not sponsored by Victor, but Victor, if you want to reach out, I think we're owed something here. Well, at least you are, Jenny.

• 9:47Speaker 01

  You're welcome.

• 9:48Speaker 00

  Yes, no kidding. And so I, one more quick follow up on that. So, but, but it, so it integrates. So Claude has gotten really, really good at MCPs and APIs and that sort of thing. But then Victor is just a little bit more. Tactical, kind of doing things or more agentic?

• 10:08Speaker 01

  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 lax 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 lot, right? So I feel like Victor, 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

• 10:53Speaker 01

  just like a task function, if that makes sense. So it's, 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. And as opposed to like contractors trying to fulfill a whole bunch of different facets of my business, it's all in one. Love it.

• 11:10Speaker 00

  Great. All right. Victor, 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, no,

• 11:55Speaker 00

  no one's gonna buy that. And dear God, if I wasn't as, 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.

• 12:23Speaker 01

  Yeah.

• 12:24Speaker 00

  So how do we figure out what we should be doing? Cause you came up with a great idea with that charcuterie cart, but not everyone can do that.

• 12:33Speaker 01

  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

• 13:14Speaker 01

  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.

• 13:31Speaker 00

  Yeah. So that's going to help. 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 nose punched in. You know, because again, it's, it's, 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, the 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

• 14:14Speaker 00

  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 part out?

• 14:32Speaker 01

  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 breadth 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

• 15:17Speaker 01

  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.

• 15:37Speaker 00

  Yeah. Jennie, your website is jennieblackwood.com. And by the way, that's Jennie with an I E, very important in the pronunciation. I nearly do Jennie with a Y, so.

• 15:48Speaker 01

  You get it.

• 15:49Speaker 00

  Yes, yes. Yep. Yep. And not a Jennifer.

• 15:52Speaker 01

  No, I am not either. 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 I E.

• 16:01Speaker 00

  So when, when folks go to your website, what would you recommend that they do? What are their next steps here?

• 16:06Speaker 01

  Yeah. So I got a couple of 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 six-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 seven-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.

• 16:49Speaker 00

  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. 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, so if you want to see the snack cards 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. I can see that. So, yeah, yeah. But yeah, that's, you have a hundred, nearly 150,000 followers there. But you're, you have great, some, some great posts that I think are quite inspiring. So Jennie Blackwood, thank you so

• 17:32Speaker 00

  much for joining us. Again, your podcast, Girl, Why Not You? Every time I see it, I like, 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, and sharing these thoughts with us.

• 17:50Speaker 01

  Thank you. I loved being here and I hope that I helped even just one person listening today.

• 17:59Speaker 00

  Thanks for listening to The Thoughtful Entrepreneur. If your goal is to grow your business, increase revenue and build authority without gimmicks, this show is designed for you. Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15-minute episodes focused on growth that actually compounds. And if you're interested in being a guest or you want to turn podcast appearances into measurable business growth, visit podverified.com. You can start for free with your Pod Verified score along with free podcast guest training and a free media kit

• 18:41Speaker 00

  builder. These tools are built to help you get booked on better shows, deliver stronger interviews and convert audience trust into revenue. No more desperate sales. You truly can enjoy all the business you like by generously sharing your wisdom. Everything we offer is built by podcasters for guests with a focus on trust, organic growth and long-term business success. Thanks again for spending your time with us. I'll see you next time.