Escape the Overwhelm: Build a Business That Thrives Without You with Special Guest, Madi Waggoner

Ever feel like your business can't run without you? In this episode, Madi Waggoner shares how to escape the daily grind, build a business that thrives in your absence, and finally take that well-earned break—without everything falling apart.

What’s Covered:

✅ The #1 mistake entrepreneurs make that keeps them stuck in the day-to-day
✅ How to build systems that allow your business to run without you
✅ Why delegation isn’t just about offloading tasks—it’s about creating real freedom
✅ The essential mindset shift to go from overwhelmed operator to strategic leader
✅ Real-life examples of business owners who successfully stepped away without losing momentum

Madi is a consultant who helps entrepreneurs fire themselves from the day-to-day so they can finally take vacation, parental leave, or a long desired sabbatical. She’s partnered with more than 40 businesses across tech startups, influencers, medical professionals, course creators, and online entrepreneurs to address the problems plaguing their businesses.

📚Book mentioned: Crucial Conversations: Tools For Talking When Stakes Are High by Joseph Grenny, Kerry Patterson et.al. 

Connect with Madi https://www.linkedin.com/in/madiwaggoner/

Learn more about Madi https://buildingremote.co/

Simple & strategic marketing solutions for the busy coach and consultant. Visit www.reinventingperspectives.com

Transcript

Madi Waggoner: [00:00:00] We want to have a retrospective or evaluate what went well and what doesn't. A lot of entrepreneurs don't take the time to do this. We need to Ask questions about how did an onboarding process go for a new hire? How am I feeling about my business? How am I feeling about the revenue? Do I even like what I'm doing right now? Especially if an entrepreneur is questioning their business. I've seen people who say, I just wanna sell it, or I just wanna shut it down 'cause I can't handle this anymore.

In some cases, it's more that they like the business, they just don't like their role, 

It.

Priscilla Shumba: welcome to the Lessons of Entrepreneurship, the Journey of Reinvention. Today, I have an amazing guest. Maddie Wagner Here with us, and Maddie helps entrepreneurs build the dream that they're going after when they say, I'm an entrepreneur. So I'm excited [00:01:00] to speak to you, Maddie.

Please let them know what's your mission. 

Madi Waggoner: I am on a mission to help entrepreneurs be able to actually fully embrace their business and grow it to the place that they want without having to be in the weeds, day in, day out, and suffering. The stress of everything, of having to manage all of that.

The way I typically phrase this as. Help them fire themselves from the day to day, because so often when they start their business, they have to do everything, but as their business grows, we need to be able to pull them back so they're not doing everything that they're actually leading their business. 

Priscilla Shumba: It's so important. I've met so many people who started businesses with a real passion for doing something, and that what you're talking about being in the day to day for too long. You lose your passion for the business and you lose your vision . So this is very exciting.

, how do you build a business with the intention of firing yourself from the 

Madi Waggoner: business

It comes down to some of the basic things that I recommend most people do in their businesses that even more established, more mature businesses don't have. For [00:02:00] example, one simple thing that you can do is use a password manager. So when you're starting to set up your accounts, don't use the simple Google login that a lot of tools have.

Super easy, but it makes it harder to delegate and share access to those tools in the future. So by setting those up , from day one, you won't have to go back and backtrack when you start bringing people onto your team. It's this delegation first mindset of how can I easily share access? How can I easily share my thinking and how I make decisions on certain things?

Another thing I recommend, especially if you're planning to start hiring in the near future, is to. Start recording Loom videos is one tool I recommend. A screen recording tool of whatever you're doing, just record. And as you're making decisions, don't just make 'em up in your head, but actually explain them.

And you can start to create a bank of resources of training, essentially for these new team members. So you can then take those links. Again, if you're using Loom, you can just grab the link rather than downloading the video and put it into a document. And that starts to become your training material for your next [00:03:00] hire.

You can organize it based on different sections or based on focuses. Say if you're bringing on a virtual assistant, all that would be admin responsibilities. Then maybe down the road you bring someone on who's doing sales, and by just doing that, as you work, you start to build again, delegation.

First, you start to build these resources just a little bit of extra time in your day to day. 

Priscilla Shumba: You have all these thoughts when you've never hired someone before. Should I give them access to my email? But my email connects to this and it connects to that. We use Google to access everything our whole lives.

And I can also see that if you do it that way because as the business picks up, you get so busy and probably by the time you hire, you're like up to your neck. You just wanna throw it at someone and just move on, which is not the way. I'm interested to know, like what are the common problems that you think entrepreneurs face that they think are not solvable .

Madi Waggoner: You actually just mentioned, one of them is, I can't think about giving access or can't think about giving whatever it is to someone else. And the reality of it is that we've built this thing from the ground up often, or maybe [00:04:00] we've acquired it and then grown it to its current state, but we have to understand that other people can be really good or even better than us at.

Certain things and we have to learn how to trust and how to build that relationship so that we can pass things off to other people. That by far is one of the most common issues that I see when I work with clients is they have this mentality, and that's what we have to talk about first. And so I use this phrase where we have to move from this solopreneur mindset to a CEO mindset of.

Doing everything ourselves. Because that's how we had to do it at the beginning and turning into a leader and starting to think that way. CEOs don't do everything the same job of everybody in their company. They allow those other people to do that work and do it the way that they see fit based on their experience.

And we have to start shifting that way first. 

Priscilla Shumba: If you take what you're doing and you look at someone who's got a team doing exactly what you're doing, I mean it's night and day. 

May be doing your best, but you can see where there's a team because you can see that one person really [00:05:00]focused on this thing, and that's why this newsletter 

you can't stop reading it because someone, that's their job to make it that way. Whereas when you stretch yourself in so many ways, I like to think of it like you end up being c average at everything. And to compete, you wanna have those A pluses in your business. And if you keep doing everything yourself, no matter how good you are you stretch yourself thin and over time you get tired.

And over time, you know the passion and that shows in the work when you're doing it yourself as well too.

Madi Waggoner: Exactly. 

Priscilla Shumba: A lot of entrepreneurs think to themselves, okay, at what point am I looking for someone, I get the delegation first mindset.

Following what you're saying. I'm creating these videos to someday hand this over to someone. At what point am I saying this is time to hand over to someone? 

Madi Waggoner: One quick check is if you're feeling burnt out or you feel like you're approaching to it, it's probably time or past time. There are a number of other things that you can evaluate, though. One, if your revenue allows for [00:06:00] it, and even if you're not stressed out or you're not feeling burnt out, if your revenue allows for it, you might wanna start exploring it because.

What we want to do when we're building our businesses is we wanna operate in the places that only we can, and also the places that we want to. Because energy is a finite resource, we can't just always feel energetic about the work we're doing. We will feel more excited and more able to engage in that flow state where things just come for us in.

Only certain tasks and we can't do that and everything. And for most of us, it's not the administrative task. So a virtual assistant is normally what I recommend first. And normally I see where people have really busy schedules. They are unable to take on more clients because they have too much work to do, too much of that supporting administrative work.

And then they have the revenue. So if they have all of those things, then. Definitely start looking. Another thing I'd say around the hiring process is make sure you allocate enough time for it, because I see a lot of people who want to just post on Upwork and they'll take whoever responds or [00:07:00] whoever seems great, but I.

We have to be really intentional. We have to create a job description that's custom for our business and be able to attract the right people, not only to the work itself, but to our mission. Because even though I do more operations consulting work, I have a larger vision of helping to support more remote first businesses because there's so much opportunity there, we can elevate other people and by talking about that vision, in my job description, I attract people who have similar values and similar.

Ideals about how we should treat other people. And so we have to attract in that way as well. We can't just throw something out there and hire whoever's in front of us or just hire someone without a job description and not get clear on what we need. 'cause then we'll end up bringing someone in who actually isn't a fit.

So we have to be really intentional when we start that hiring process as well. 

Priscilla Shumba: I'm so excited you touched on remote work 'cause I think this is something that a lot of entrepreneurs, you're seeing it happening in this space, but you're not sure exactly how to get your feet in there. You're not sure how to navigate this. But Maddie, I've done your [00:08:00] disservice because I haven't let people know how you got to this and what you've created here.

So maybe you can talk to us about that.

Madi Waggoner: Sure. My company is called Building Remote because I've built my career based on remote work, and over the years I've had this opportunity to get to know people who have been in some really tough situations. For me personally, I wasn't struggling in the same way that these people were, but I didn't have the opportunities.

I didn't live in a tech hub. I didn't have all of these really elite schools around me. I didn't go to an elite school. I didn't have the connections that might come from those, and so I had to make my own way, and I , did that through remote work. There wasn't a lot of opportunity for me where I lived, and as I went through the years and went through my career, I came across other people who had similar circumstances or they had things like.

A wife who was expecting a baby and suddenly her husband passes away and she's having to figure out how to build up a stronger income stream in order to support her [00:09:00] coming baby. Or other people who have had dealt with domestic violence. There are things like that where I wanna support these people and we can do this through remote work and by training people up.

That's where the long-term vision of what I wanna do. I'd love to have some. Maybe not a nonprofit arm of the company, but something along those lines. Because remote work just offers so much benefit, but it has to be done right. And I've seen so many people say, oh, remote work is easier. It actually takes a lot more intention because you can't fall to the default of just walking over to someone's desk.

You have to write things down. You have to be organized. You have to communicate in a consistent way so that everyone is on the same page and we're all rowing in the right direction.

Priscilla Shumba: I love that mission and I think I understand because I've always lived in places where there was nothing. 

So my starting the podcast was like I've gotta create a network out there because there's nothing really that I can create here. And, find work out there without actually having to move.

There's so much of the world where there is no opportunity for work, where [00:10:00] you have smart, bright, eager, young people and it's this, huge opportunity that's waiting for people to tap into it. And people who are waiting to say, we wanna work 

we don't want to cross oceans to go and look for work and leave families and leave everyone behind. We just want to work. That's really exciting what you're doing there, Maddie. And I know that you've worked with a lot of entrepreneurs. I'm interested to know what has been your favorite or something quite memorable to you in working with entrepreneurs?

Madi Waggoner: I'll go back to one of my earliest clients who was a a personal finance blog at the time, and now they've turned into, for lack of a better term, I almost wanna say more of an empire because they've done so much. They have courses, they're educating people, they are. Doing somewhat similarly to what I wanna do, where they're enabling people to start their careers in this remote capacity.

And it's been so fun to see where they've gotten to now. 'cause we first started working together, I. Five years ago. And just seeing that growth has been so exciting because I [00:11:00] started out working with them on just starting to build out systems so that the business owner could step out. So I came in and started managing things for him and started streamlining it.

And then I hired people into takeover for me. And that was definitely one of the most enjoyable, probably because I can see the entire history. But I also have another example of when I worked in-house with a tech startup. So I was one of their internal team members, not a consultant at the time.

And we started from a very small team, just three of us. I was the third employee and we were able to increase the revenue over two years by six times. And a lot of this happened through different changes that we made operationally so that we could scale. And being able to see that kind of, system building and team enablement so that they can make decisions on their own.

I love doing that kind of work and that's exactly what I do with my clients these days too. 

Priscilla Shumba: when you're a new entrepreneur you hear those words, systems and scaling and you're just thinking to yourself, okay, let me just focus on what I'm doing right now. And then I'll learn those words and what that means when I get to a certain [00:12:00] stage.

You prioritize helping entrepreneurs step out of their work being able to have a business that runs without you being in it. And a huge part of that is being able to build a phenomenal team. And when you look at like the first hires, you've talked about the VA and putting aside the things that stop you from being in your flow.

For the entrepreneur that's thinking, what makes for that phenomenal team? Because people may have hired people and didn't work out. You know how recruiting goes. Sometimes it's not the right fit. Sometimes you gotta move on, but you're thinking to yourself.

How do I create that culture of a phenomenal team? . 

Madi Waggoner: When I'm doing hiring, I look for a number of different factors, but one of the key ones is that they are growth oriented. They need to show me that they have an innate desire that is within them, not from anyone else. Where they're going to try to continue to move forward because when they are motivated to do that for themselves, they're motivated to do that for their work.

They aren't gonna be satisfied with the status [00:13:00] quo. They will want to take whatever they have and make it better and continue to make it better even as they continue to improve it. Another piece that I recommend when you're trying to build culture is I like to create this visual of think about you as the founder, the entrepreneur as a single dot, and then when you add in someone else, there are another dot and there's a line between the two.

As you add more people, there are more dots and more lines going to that founder. What ends up happening is then we start to get this bottleneck and this burnout for the founder because everyone is communicating and collaborating with that person, and no decisions are being made without that person involved.

It becomes very overwhelming. What we want to do is when we start having more of these dots on the outside of the circle, so the team members and the founders in the middle, we wanna start drawing these lines between the team members. So when people come into the business, we wanna be very intentional with their onboarding process.

One way we do that is we could give them. We could call it an onboarding buddy, where we wanna introduce them purposefully to other people on the team. Now, I like to use this analogy of when we think [00:14:00] about kids, they make friends very easily. They'll go up and say, hi, , this is my name. Let's play together.

We as adults, we generally aren't that intentional with trying to build relationships, and this happens in the workplace too. So when someone comes onto the team, we want to introduce them to everybody else. We want to give. Prompting questions from the people who are part of the team. 'cause they're more comfortable, they're not new.

To ask the new person about themselves their work and explaining how the culture works. We start doing this because we wanna build these relationships. So we have these lines between the dots on the outside of the circle, and then what we start to see is decisions happen all the time without the founder involved. 

This culture that is everyone working together towards this overall mission, allows that founder to have dotted lines to them where they're just finding information out after the fact. They're more looped in on this is what we did, FYI, it's not, we need your opinion. And that frees them up so that they can actually lead the business.

But those are some of the things we have to do in order to build that team and build that culture. 

Priscilla Shumba: I think about when you [00:15:00] actually work, a regular job and. You get hired by one person and maybe you never see that person again on the first day. You know, Nobody, you're just like a person walking through the place, and it's that dread of new jobs that you're talking about.

But when you're intentional about it, and I get that you say when with remote work, you must be that much more intentional. 

Madi Waggoner: It has to start with onboarding. This is a subject I'm very passionate about. If you can't tell, because when someone comes in, we spend all this time, we spend all this money. When you think about someone's time to bring someone else on, and we're hiring them, we're investing money into them to pay them so that they.

Show up for their job. We want to make sure that we enable them from the start. The founder, whoever the manager is, needs to invest time too. I recommend that they do a check-in and intro call their very first day, and then they check in throughout the week. I love tools like Slack because it allows people to stay in touch throughout the day so their manager can ask them questions around, how are you doing?

[00:16:00] How am I being a bottleneck for you if you're trying to get some work done? Asking these very open-ended questions helps to build this sense of openness and communication and collaboration. From the start. So that's what they get used to from their very first day. And then at the end of the first week, I like to encourage doing some kind of check-in call with that person because again, we're trying to build trust.

We're trying to do this from the start. you can Do this with clients or customers as well. The things that you do at the very beginning, that's how you set expectations. And they've signed on, you've sold them on something, whether they're an employee or a customer. They're expecting you to follow through on the promises you made leading up to that point.

And if you fall short, that hits them negatively, which then impacts their perception of you and how long they might stay with you. So onboarding , whether it's for internal team members or for customers really important.

Priscilla Shumba: Let's say you feel that it's something that you wouldn't be strong at doing, how do you access the services of someone like yourself, and what is it that you are looking for [00:17:00] to work with someone so that it's a good fit?

Madi Waggoner: Yeah. Most people who are not strong in operations work like I am, are a great fit for working with me because , my strengths will compliment their weaknesses or just the gaps that they have in their team. And I often would say also that entrepreneurs shouldn't necessarily feel the need to be really strong in these tools.

They need to allow someone to come in or someone on their team to build it up, and then they just use them. I wanna make sure that's clear. If there's a lot of chaos in their business, it's oftentimes that they don't have these strong systems. They don't have these tools set up to best support what needs to be done in the business.

So if there's ever anything like that, someone like me or another operations person is a perfect fit to help them address those issues and create some structure and really strong foundations in their business so they can reach the goals that they want to in their business. 

Priscilla Shumba: And what are you also looking for? 'cause I'm thinking of a situation where maybe the business is doing well, you're really busy, there's a lot of chaos, they need order, you don't have the time to create the order. So [00:18:00] you're looking to hire someone, come in and the commitment that you need on the side of the party that needs someone to come in.

Because I'm thinking you set up the systems and. At some point you hand them over or you need them to make sure the systems are running or to maintain them. . 

Madi Waggoner: Yeah, so when I work with clients, what I do is I actually set the expectation that I don't want to be here long term because I want to enable you and your team to do these things without me. Because if I don't do that, I'm not doing my job well. I need to help teach and help explain. I need to set things up well for them.

I. Yes, but I wanna teach them. So when I build out systems, or I also have someone that I work with who her team does Clickup build out. So it's a project management tool to keep track of tasks and things. Whenever they build out a system, they explain that you should have someone internally in your business, like an operations manager who is.

Responsible for those tools. So even if we build some of these systems, there should be someone on your team who is able to come in [00:19:00] and make sure that everyone uses it properly and stays on top of the work so that everything gets done quickly and on time. It should not be the entrepreneur's responsibility depending on the size of the company.

If it's just them and maybe one other person, maybe. But if they're a little bit larger than someone else should be in that seat. 

Priscilla Shumba: Thank you for that. I always think of situations where you pay to get everything that you need and then it ends there. That does happen because of that handing over and thinking forward of it's not like money's gonna solve the thing.

Someone actually has to take this up and follow through to make sure that you make use of these systems , one of the reasons that entrepreneurs start a business is to find freedom. And we end up doing the exact opposite of gaining freedom.

We get more busy all the time. We can't walk away, we're , more stressed than the regular job. What do you think is the missing thing that people don't get in that process? 

Madi Waggoner: There is a concept especially in software companies around this idea of what they call retros, where we want to [00:20:00] look at a project and ask questions. We want to have a retrospective or evaluate what went well and what doesn't. And I see a lot of entrepreneurs don't take the time to do this. We need to do this with large projects.

In some cases, small projects too. We need to ask questions about how did an onboarding process go for a new hire? How am I feeling about my business? How am I feeling about the revenue? Do I even like what I'm doing right now? And by asking these very introspective questions. Not only of ourselves, but of our teams.

It helps us to bring up some of these points that maybe we've just ignored or we haven't actually , fully thought through another way to do this. Especially if an entrepreneur is questioning their business. Or sometimes I've seen people who say, I just wanna sell it, or I just wanna shut it down 'cause I can't handle this anymore.

In some cases, it's more that they like the business, they just don't like their role, and again, we have to ask questions around what the role should be. That's something that I do at the very beginning of a lot of my engagements with clients of this is your role, what you're doing right now. [00:21:00] Half of this should not be yours, or more than that is really common as well. And so simply asking these questions and evaluating and asking, what am I happy with? What am I not happy with? Those very basic questions can sometimes pull out really helpful insights and if they need help with that's something that I often do with my clients as well. 

Priscilla Shumba: Just wanna make sure before we wrap up that I get this in there because I know that people who are listening might be thinking, okay, you talked about, sometimes you just look for someone on Upworks, which is what people typically think. You need someone who comes in to just take this task away and you think, okay, let me go to Upworks, let me go to Fiverr.

I'm interested to know where you would say. Are good places for someone to find remote talent or maybe good ways to think about getting remote talent. 

Madi Waggoner: Yeah, so I mentioned earlier creating a job description. And the reason why I lead with this is because I wanna make sure people do not, they should not put out their email address when they post a role. There's no organization to it. It will flood your inbox. Just [00:22:00] don't do it. And then when you're starting to post in different places, we have to think about.

Where are the right candidates going to be? There are a number of job boards, like We Work Remotely is a good one, but there's also a lot of really fantastic Facebook groups where these people hang out. And so if you can find out if these groups, sometimes they're Slack groups as well. Circle's another popular platform for some of these groups.

If you can find out if you can post into some of those groups, that can be a great way to find really talented people and then , you may or may not have to pay to be able to post 'cause some sites like we work remotely, I mentioned you do have to pay to post there and you don't wanna increase a whole lot of costs for yourself.

LinkedIn is another one. There's a lot of traffic on LinkedIn though, so you have to be really. Good with your job description to make sure you're attracting people in. You can't just throw something up. You have to be very intentional. But those are some of the sites that I would recommend, those groups in particular will be especially helpful.

But it takes a little bit of work to understand how to find them and where they might be. 

Priscilla Shumba: Thank you for that advice. I always [00:23:00] ask our guests to give us like a book that they would say, change the game for them in their business, or change the game for their clients . 

Madi Waggoner: Like I said earlier about this solopreneur to CEO mindset, we have to make that shift, and part of that is leading, which means having difficult conversations. There's a book that I love called Crucial Conversations that has helped me significantly in being able to have challenging conversations with.

My clients or with their team members or even people in my personal life. What it does is it walks you through a number of different steps you should take in order to create. This is silly, but they call it the pool of shared meaning, and all they mean by that is we need to understand what the other person's goal is and what my goal is so that we can find a.

Mutual goal because if we start from there, it's much easier for us to bridge the gap so that we can come to a really good resolution. And every leader, every entrepreneur, especially if they're starting to hire, needs to understand how to have those conversations.

Priscilla Shumba: I like that concept of shared meaning. 'cause you mentioned you listened to the previous podcast with Dave Kolbe, and one of the things that he was telling me [00:24:00] about was sometimes when you're really good at selling, entrepreneurs, you're good at selling and enrolling people into the thing that you want them to do.

But a lot of times if you don't do it with that sort of shared approach, people are left with buyer's remorse, whether that's your client or that's your employee or your contractor. They're so excited because you've talked them into things and you hype them up, and then without that hyping up, 

there's no shared thing for them, and eventually they discovered that. They were never a part of the thing. And so I'm really interested. Crucial Conversations. Do you know the author? 

Madi Waggoner: I don't have it off the top of my head, but I have it right here. 

Priscilla Shumba: Crucial Conversations.

Madi Waggoner: I dunno if it's backwards for you. Patterson is the main one. Yeah, Steven r Coy did the foreword, but Patterson Granny McMillan and Schweitzer, 

Priscilla Shumba: thank you for sharing that.

Madi Waggoner: yeah. 

Priscilla Shumba: Maddie, if you were gonna create a bootcamp for founders what would be the first challenge that you would say, you know what? Get through this, and then we'll, [00:25:00] let's get to the next thing. 

Madi Waggoner: What I always do when I'm working with my clients, this is actually a resource I'd love to share with your audience, I call the founder's focus assessment because what it does is it walks them through. How to evaluate the work that they're doing, because we have to get really clear on this first, because most of the time, what founders are doing is not what they should be doing.

We need to shift a lot of that off of their plate, whether that's through automation and systems, or by hiring someone, or in some cases simply not doing it in order to help them focus on the things that will move the business forward and help them to focus on the energy producing tasks of leading their business or doing the things that are their zone of genius.

So that is absolutely the first thing that I would focus on in a bootcamp. 

Priscilla Shumba: Thank you so much for that, Maddie, and I think that resource. We'll get the link and it'll be in the description. By the time the episode is out or keep checking, we'll keep updating that and letting you know what Maddie's doing. Maddie, is there somewhere people can follow you if they're interested in connecting and knowing more about what you do.

Madi Waggoner: Absolutely. [00:26:00] I'm very active on LinkedIn. Just look for Maddie Wagner, MADI, no double Ds in my first name. And if you just look for me, you'll see a founder at Building Remote. That one's me. I and we're also redoing our website@buildingremote.co. And so we're gonna be publishing a lot more content there as well. 

Priscilla Shumba: Yeah, that's exciting. I think this is an area that. It really could propel a lot of small businesses and a lot of new entrepreneurs. It's the time. It's ai, it's remote work. You've got to just move with the time. It's an exciting time to be alive. Thank you so much Maddie for joining us and thank you for sharing your expertise with us. 

Madi Waggoner: Thank you so much for having me, Priscilla.