Powerful Women Rising - A Business Podcast for Female Entrepreneurs

Beyond Google: The Power of Human Connection in Business w/Jenn Hartt and Jess Thompson

• Melissa Snow - Powerful Women Rising, LLC • Episode 100

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What’s the biggest difference between entrepreneurs who struggle and those who thrive? 

In the second episode of the Powerful Women Rising Impact Award winners series, 2024 Coach of the Year Jess Thompson and 2024 Business Support Person of the Year Jenn Hartt explain that success isn't just about having the right strategies - it’s about having the right support.

We discuss the power of human guidance in business and how coaching, strategy, and execution work together to turn big ideas into real success. 

Jess helps entrepreneurs cut through overwhelm and build thriving businesses while Jenn brings their visions to life through creative strategy. Together, they’re proof that no one builds a successful business alone.

Listen and Learn:

✅ Why AI tools can’t replace real human insight in business strategy
✅ Why community and mentorship are essential for overcoming challenges
✅ The surprising freedom that comes from asking for help
✅ The mindset shift that separates struggling entrepreneurs from thriving ones

These two incredible women remind us that to build a business and a life that truly works for you, having the right support system is essential.

This episode is part of the 2024 PWR Impact Awards Winner Series, featuring women entrepreneurs who are redefining success and impacting the lives of others. Want more inspiration and real-world strategies to make an impact with your business? Subscribe and don’t miss the next episode in this powerful series!


Links & References:

Learn more about Jenn Hartt:

Learn more about Jess Thompson:

Connect with Me, Your Host Melissa Snow!

Melissa Snow is a Business Relationship Strategist dedicated to empowering women in entrepreneurship. She founded the Powerful Women Rising Community, which provides female business owners with essential support and resources for business growth. Melissa's other mission is to revolutionize networking, promoting authenticity and genuine connections over sleazy sales tactics. She lives in Colorado Springs with her two dogs, three cats, and any number of foster kittens. She loves iced coffee, true crime, Taylor Swift, and buying books she’ll never read.

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Melissa Snow:

Hello friends, welcome to the Powerful Women Rising podcast. So excited to see you guys today. I'm excited to interview you. I was saying before we started recording that you guys actually do know each other. I think you nominated each other for these awards, but I didn't know that when you put you on an interview together. So this is super fun. So I am here with Jess Thompson and Jen Hart. Jess was the winner of the 2024 Powerful Women Rising Impact Award for Coach of the Year, so congratulations on that. That's so awesome. And Jen, of course, was the winner of the 2024 Support Person of the Year and I've heard so many great things about both of you. These awards were based on nominations by your peers and then the winners were chosen by a panel of judges. So lots of really good nominees and super excited to get to talk to you guys today as two of the winners. So before we dive in, let's start with Jess and just tell everybody a little bit about you and what you do.

Jess Thompson:

Yeah, so business coaching, hence why the award. But I focus specifically on working with small businesses, particularly women entrepreneurs, and just helping them take their big ideas and put that into action. You know an actual plan that you can follow and be held accountable for.

Melissa Snow:

I love that, and how long have you been a coach?

Jess Thompson:

The coaching is actually relatively new. It actually segued from leadership and sales training that I have been doing, but the coaching one-on-one is really just the last six months or so.

Melissa Snow:

Oh, that's awesome Congratulations, but it sounds like you have lots of background, lots of knowledge and experience with all sorts of things business related.

Jess Thompson:

Yeah, and a lot of unofficial ways, been doing this for a long time. Yeah, I was going to say Jess has been coaching her entire career. I feel like, yeah, that's awesome.

Melissa Snow:

Okay, just getting paid to do it within the last six months or so, yeah, well, that's even better. Getting paid to do it is even better. And Jen, tell us about you.

Jenn Wayboer Hart:

Yeah, I'm a creative strategist. I started off as a virtual assistant but I rebranded as a creative strategist I guess three years ago, now almost four. So I also help entrepreneurs take their big ideas and turn them into reality. But I do more task-based work. We do strategy sessions for the big ideas and then break it down and I help my clients execute those plans.

Melissa Snow:

And I love the two of you together because you are helping people with the same things but in very different ways.

Jenn Wayboer Hart:

Right, yes.

Melissa Snow:

And that's that's been very helpful. I have an assistant also. I don't call her a virtual assistant because I don't. I feel like she does so much more than that. She's like my, just my lifesaver. But I, when I hired her, that's been where I have been able to like, like, have all of these great big ideas that I'm like we should do this, we should do this, could you do this? What if there was a thing on the website where you could do blah, blah, blah and like I've had all of these great ideas for years and years. They just like never go anywhere. And so to have someone like Jess to help us come up with those ideas, streamline those ideas, think them through, think like is this really what you want to do? Is this really as good of an idea as you think that it is? And then to have somebody like Jen to actually like execute and help us make the thing happen, is you guys are like the dream team here.

Jess Thompson:

Yeah, and there's definitely a lot of overlap, but I think Jen and I are very similar in our approach, so it makes sense that we're doing, you know, similar things.

Melissa Snow:

Yeah, for sure, awesome. So, Jen, what do you?

Jenn Wayboer Hart:

love about supporting other entrepreneurs in their endeavors, so I actually really honed in on this last year at a retreat that Jess and I were at together actually it was the uplift retreat last year and we had a speaker talk about how dopamine is actually what happens before the thing happens, and I realized my why is when my clients experience that dopamine hit before their idea comes to life, so right as I'm sending them their link to their new website or their strategy for social media or whatever it is, it's the excitement that I know they have that creates the excitement for me too.

Melissa Snow:

I love that. That's cool. And Jess, how about for you as a coach? What do you think makes a great coach?

Jess Thompson:

I think it's really listening. So my value really just comes in in being able to bring out the best in my clients. So being able to bring out the best in my clients, so being able to help facilitate that brainstorming and idea creation and figuring out like you said, melissa, is this really what I want? Is this really long-term, going to plug into not only the goals I have for my business but the type of life that I want to live, and seeing that your business and your life, personal life do not have to be two completely separate entities. There's a ton of crossover and they can live harmoniously within each other. I think coming to that realization with my clients is always like this really, it's a really fulfilling moment for them to see that this can be everything I want it to be and I don't have to sacrifice in order to make this happen.

Melissa Snow:

Yeah, and I can do it the way that I want to do it, and I don't have to sacrifice in order to make this happen. Yeah, and I can do it the way that I want to do it, even though there's, like all these experts and gurus and people who say, like this is how you do it and this is what a successful business looks like, and this is what a successful woman looks like. You can have your own idea of that and still make that successful.

Jess Thompson:

That's the part? Yeah, absolutely, those are guidelines, not rules.

Melissa Snow:

Yeah. So I'm going to ask you both a question that I didn't prepare either of you for. So I'm going to start with Jess and give Jen some time to think about her answer, although I suspect you both know the answer right off the bat. So I'm thinking as I'm talking to you two and about what Jess does as a business coach and what Jen does supporting people in their business endeavors. And I'm thinking about, like, if I was just getting started in business or maybe I was a year into business but hadn't quite found that traction that I wanted, couldn't I just Google, like how to do the thing, what should I do next in my business? How should I run my business? And then couldn't I just go to like chat, gpt and be like help me figure out my content strategy, or like, help me map out the steps that I need to take to make this big idea happen? What is the benefit to me in hiring a business coach instead of doing that?

Jess Thompson:

Yeah, so first off I will say that I'm a huge fan of AI. I use AI a ton to be able to brainstorm and ask those questions. But for me that is a launching off point. That is not like the answer that then I base everything off of. So it helps me just be able to critically think a little bit better and kind of get the juices flowing, which is ultimately what a coach does, except for a coach knows you a little bit better than AI does. Hopefully, maybe not in a few years.

Jess Thompson:

Ai is getting pretty great, but as of right now, a coach can know you sort of on that more personal level, pick up on things that you don't even know about yourself. So AI is modeled off of all of the things that you tell it to know about you. But if you don't know to give AI that information, it can't give you the full picture of what you're really wanting and ask those really critical questions. It's really just a mirror of yourself. So a coach or even a support person like Jen is going to broaden your perspective beyond what you already think you know and the questions you already think to ask. So it's really just broadening that perspective. But I do say that AI is an excellent launching off point. If you are not at the point yet to hire somebody, that's a great way to just kind of start thinking outside the box.

Melissa Snow:

Yeah, absolutely. I always think of it as like it's one of many tools, but it's not like the end all be all of the things right. It's kind of like with if we want to, like, lose weight or be healthier. It's like, yes, exercise is part of that, but we can't just exercise and also eat whatever we want, like we have to do a number a number of different things. Yeah, yeah. What about you, jen? What's your thoughts on that?

Jenn Wayboer Hart:

It's the human piece, which is largely what Jess was saying too, is AI is theoretically never going to be human. I mean, I had a client that actually let me go because she decided she was going to use AI to do her whole social media plan and within six months she had rehired me again because AI just couldn't know what she wanted her business to look like online. She wanted her business to look like online, and we can dig a little bit deeper through our experience, our education, to really exactly what Jess was saying. Pull up those pieces that you're not feeding into AI. I use ChatGPT nearly daily, but it's never going to replace the human conversations, which is where most of the gold comes from, just sitting and talking with people. Even if I'm posting on social building a website, everything I get is from community and conversation. But ChatGPT is a great place to start to get things rolling, and then you hire the professionals to help you take it to the next level.

Melissa Snow:

Yeah, I love what you guys are saying about, like the ability to communicate and the ability to feel and the ability to use your intuition even to help people. It's like this is why we don't network exclusively in emails, right? Because, like, if I were to ask you, you said, oh, I have this new idea that I'm really excited about and I'm going to do this, this and this. And then I would say, like, so, when you think about doing that, does that really like light you up? Do you feel like super, like jazzed inside? And your answer is yeah, right, like that's going to take me in a very different line of questioning than if your answer is yeah, and, but I can't tell the difference. No idea which one it was.

Jess Thompson:

Yeah, absolutely, and that's huge and even those feeling questions exactly what you said, melissa like. Does this make you, does this light you up? Does this make you feel excited? Does this make you feel happy? Ai is not, at this point, asking those types of questions and looking for those types of responses.

Melissa Snow:

Yeah, and those. I think you realize as time goes on in business how important your answers to those questions are. In the beginning it's like I don't care if it makes me happy or brings me joy, I just need to make some money. And then you realize joy, I just need to make some money. And then you realize okay, maybe there's a little bit more to it. Yeah, definitely. Did you want to add anything to that, jen?

Jenn Wayboer Hart:

Yeah, I think that's why, like my podcast and community is absolutely everything, and networking like mostly your networking platform to allow people to get that feedback from other humans that can see your facial reactions, that can see how you respond online to other people, can help influence how you want to show up for your business and your brand as both a human and a business.

Melissa Snow:

Yeah, agreed. So let's talk a little bit about your inspiration, not necessarily like why you do what you do, because we've talked a little bit about that and what you both love, about what you do and why it makes you so great at what you do. But business is hard and whether you've been in it for six months or 16 years, there's still moments that you're like why am I doing this? I have no idea what I'm doing. This is never going to work. So I would love to hear from you guys, when you get in those spaces of like everything is going wrong, I'm not making money, I'm not bringing in new clients, whatever it is, how do you get yourself to keep going?

Jenn Wayboer Hart:

For me it's community, and I moved across the country almost going on seven years ago and that was the hardest part for me was losing my community that I could turn to when things went wrong, cause I've been an entrepreneur at some level for the last 14 years. I just realized, as I was saying, that and it's never going to be perfect and you have to have the people you can lean on when you have the nightmare client or, even bigger, when you make a mistake, because I think, especially as female entrepreneurs, we can be really hard on ourselves when we mess up and it's going to happen no matter what.

Jenn Wayboer Hart:

So having that support system and mine started with friends, fellow entrepreneurs, because they get it, and now I'm lucky enough to also have my husband in my corner for when things get hard too.

Jess Thompson:

Obviously, I resonate so much with what Jen said, but I think for me it's really about building the life that I want, and a lot of that revolves around freedom. So I think, especially around the pandemic, we all saw how fragile our society and our systems can be just depending on outside influences, whether it's the economy or it's lockdowns, or even it's just your kid is sick and has to stay home from school. And so I wanted to build a life that I had control over and that I could say, yes, I'm pouring into work right now or no, I need to take my foot off the gas pedal for a little bit and really just kind of create the schedule that I want, create the flexibility that I want and be able to pour into where I think is valuable. My husband and I even joke about sometimes being able to do a lot of things that I don't want to do, and I think that's a really selling everything and buying an RV and just kind of touring around the country, and it's kind of liberating to think if we really wanted to do that.

Jess Thompson:

Obviously there's a lot of considerations, but I could right, I'm building those blocks in place to be able to say, yes, we could pick up and move if we wanted to, and obviously we'd be giving up some community. But we can make our life whatever we want it to be. And so coaching I happen to love it and I'm very passionate about it, but really it is kind of that tool in my tool belt to be able to say this is how I get to build the life that I want to live and surround myself with people that I like. So it's purely selfish.

Melissa Snow:

Melissa, that's your new tagline H Melissa, purely selfish.

Jess Thompson:

That's your new tagline Hire me, I'm selfish, I'm very selfish. Jen is all about community, I'm all about me.

Melissa Snow:

No, those are really good points, though, because I think I mean we do. We do have to be honest about the balance between we want to help people, we want to impact people's lives, we want to change the world. Like I don't really know any entrepreneur who became an entrepreneur because they were like I don't give a shit about people, I just want to be rich, right. But we also don't want to go too far over on that end of like I just want to help people and save the world because also, like we're humans with bills to pay, so and with joy that we want in our life and families and pets, and like there's a way that we wanna live and something that we want for our life, and this is what allows us to do that. So it's awesome to be able to do both of those things at the same time. So we touched on this a little bit.

Melissa Snow:

My last question was gonna be just about any advice that you would give to other female entrepreneurs specifically who are either considering getting started in business. Maybe they are just getting started, maybe they've been going a couple of years, but they're just not getting the traction that they want. You talked a little bit about having a community, people to rely on and go back to and a support system that are like no, you got this, we've all been there. We talked a little bit about remembering, like your, your bigger picture, like, why are you doing this when things get hard? What other advice do you have for anybody who might be listening to this podcast who's in that situation?

Jess Thompson:

Say it's that every entrepreneur comes to a fork in the road and realistically, many over the course of your career where you have to ask for help, and that can look like a lot of different ways.

Jess Thompson:

It can look like community that Jen's talking about.

Jess Thompson:

It can look like hiring somebody that's a support person, hiring more staff or just investing in something that feels scary investing in a tool or software or education for yourself, and for a lot of people, that fork in the road feels scary investing in a tool or software or education for yourself, and for a lot of people, that fork in the road feels like failure.

Jess Thompson:

It feels like I wasn't able to do it by myself. So this is a result of me not being good enough or not being smart enough or not working hard enough, but really, in my mind, that fork in the road is a measure of success. It means you've grown to the point where you have outgrown what you can do yourself and now you need a team and a village and whatever that looks like, and so my advice would be to not shy away from that. That that's an opportunity, that is a measure of growth and success, and to embrace that, even though it feels really scary and you are taking a huge risk when it comes to, you know, bringing in somebody else or paying for something. But nine times out of 10, it's worth it because, even if it wasn't the right decision, you're still learning. You are still moving forward, not backwards.

Melissa Snow:

Yeah, absolutely. I often say that there's no such thing as a solopreneur, because and there's no award that you get at the end of this, that's like congratulations, you did all of it yourself. Yeah, we never ask people when they're celebrating, like big milestones or I got a new client or something like you'd never hear somebody be like well, did anybody help you?

Jess Thompson:

Yeah, it only counts if it was just you, yeah exactly.

Jenn Wayboer Hart:

What about you, jen? Yeah, I mean the first piece would be to get involved in some sort of coaching and whether there are group programs that are a little bit less expensive barrier to entry. But I think the biggest thing I would say is keep your business in alignment with who you are. And at the beginning of my business I was a VA.

Jenn Wayboer Hart:

I started my business because I was at rock bottom in every part of my life, so I was taking any and all business. If someone was willing to pay me 10 bucks to do something, I was going to do it, and it took years before I realized that saying no to business that didn't align with who I am as a human is okay, and I had more space and more clients that do align showed up for me. So I think keeping your why which I think that phrase can be a little overused but whatever your passion is, keeping that at the forefront and making your decisions and knowing that you can say no to the business that doesn't align with whatever that purpose is and a coach can really help you figure that out. In the meantime I'm coaching changed my business.

Melissa Snow:

Yeah, I love that. Such good advice and so inspiring to talk to you guys and all of the women that have won these awards, just to hear from people who are succeeding, they're doing things the way that they want to do it, they're staying true to who they really are and their integrity, and they're able to do it and be successful at it. I think it's just. It's something that we all need to hear. So thank you both so much for sharing your stories and your wisdom. I know we could go on for hours and hours because you're both so knowledgeable and awesome, but if people want to connect with you further, what is the best way for them to do that? Jen, I know you have a podcast. What else you got going on?

Jenn Wayboer Hart:

Yeah, so my podcast is your Next Business Bestie and it is all about connecting entrepreneurs to each other and sharing our stories, because I believe there is so much power in storytelling. But you can find me on Instagram at LifeJensWei. My email is Jen at JensWei. My website is JensWewaycom. There's two N's on Jen always.

Melissa Snow:

As long as you remember Jen's Way with two N's, we will find you somewhere.

Jenn Wayboer Hart:

Exactly Everywhere.

Melissa Snow:

Awesome, I will put those links in the show notes. And what about you, jess?

Jess Thompson:

So, similarly on Instagram, my Instagram is Complete small biz Academy. My website is complete small biz Academycom Either of those you know, just connecting and, like Jen said, building that community. I would love to hear from people and, even if it's not to actually hire me for anything, I just love knowing more especially women entrepreneurs, because I just love seeing all the different ways that that can manifest. So you can send me a message on Instagram or a chat in my website.

Melissa Snow:

Awesome, yeah, and it's always really fun when someone reaches out and is like hey, I just followed you, I heard you on such and such podcast Cause. Sometimes it's like we do these podcast interviews and then they go off into the void and we're like did anyone hear it? I don't know, maybe.

Jess Thompson:

Yeah, I agree, it's always fun to know where, where you heard my name.

Melissa Snow:

Yeah Well, thank you both so much for this interview. Congratulations again on your awards and, uh, we look forward to connecting with you more in the future.

Jenn Wayboer Hart:

Thank you so much.

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