Ep 124: From Bottleneck to Business Leader
How Creative Entrepreneurs Can Fire Themselves from Daily Operations with Madi Waggoner of Building Remote Co
SUMMARY
Are you drowning in the day-to-day operations of what was supposed to be your dream business? If you can't take a vacation, delegate meaningful work, or step away without everything falling apart, you've become the biggest obstacle to your own growth.
In this episode, I sit down with Madi Waggoner, founder of Building Remote, to explore how creative professionals can transition from being stuck in daily operations to leading with vision. Madi has helped over 50 entrepreneurs fire themselves from their businesses, and her insights will transform how you think about delegation, team building, and sustainable growth.
The Reality Check Every Creative Entrepreneur Needs
Most creative professionals start their businesses to have freedom and do what they love. But somewhere along the way, they become trapped. They're answering every email, jumping on every project, and saying "I'll handle that" to everything that comes up.
Sound familiar? You're not alone.
Madi shared a powerful observation from her work with tech startups: "When I sit in on client team meetings, I often hear the founder say, 'Oh, I'll handle that, I'll handle that, I'll handle that.' We have to change that mindset of you are not the one who is actively always taking things on."
The LIFT Framework: Your Path to Freedom
Madi's proven LIFT framework addresses four critical areas every growing business needs:
L - Leader
This isn't just about management skills—it's about fundamentally shifting your mindset from doer to delegator. The solopreneur-to-CEO shift requires changing how you think about yourself and your role in the business.
I - Infrastructure
You need systems that work without you. This includes clear mission, vision, and values that serve as decision-making tools for your team, plus the operational systems that keep everything running smoothly.
F - Fuel
This encompasses everything that drives your business forward—marketing, sales, client delivery, and the experience you create for your customers.
T - Team
Building a team that can execute your vision requires intentional hiring, onboarding, and ongoing development processes.
KEY TAKEAWAYS
⚡️Stop Being the Default Solution: Every time you say "I'll handle that," you're reinforcing your role as the bottleneck. Instead, ask "Who on my team can take this on?"
⚡️ Delegate with Structure: Effective delegation isn't just handing off tasks. Get buy-in, provide context, set checkpoints, and coach through the process to ensure quality results.
⚡️ Involve Your Team in Creating Systems: Don't write all your SOPs yourself. Record a quick Loom video explaining the process and have your team member create the written documentation. They'll be more invested in using something they helped create.
NOTABLE QUOTES
💬 "If you want to have strong team members, you have to start the hiring process off well. Don't just say, 'Oh, I need help. I need an assistant.' You need to be more strategic in how you're actually breaking out what you need to hand off to this person."
💬 "When you're working in a remote environment, we have to be intentional. You can't build culture remotely the same as you can in the office—you have to be intentional about it."
💬 "Building a business that can run without you isn't about working less. It's about working on the right things."
EPISODE RESOURCES
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TRANSCRIPT
Okay, real talk. How many of you have amazing systems for your creative work, but your finances are still a hot mess, right? That used to be me too, until I found the Core Group. They're accountants who actually get creatives and they help you build financial systems that create breathing room instead of panic attacks. Using their profit first methodology means that you pay yourself first. Crazy, right? Go check them out at coregroupus.com.
Creative professionals often become the biggest obstacle to their own business growth. Trapped in daily operations when they should be leading with vision. And today we're exploring how to fire yourself from the day to day with systems expert, Madi Waggoner. Let's get into it.
Taking creatives from chaos to clarity. Welcome to Creativity Made Easy, the podcast for professional creatives who want to scale their business with efficiency. I'm your host, creative process coach and consultant, Dustin Pead, and I'm here to help you go from chaos to clarity in your creative business. Whether you're a solo creative, just starting to build systems or you're leading a creative team that's ready to scale, this show will give you the frameworks, tools and strategies you need to create your best work while building a sustainable business. So let's dive in.
A few weeks ago, I had one of those networking calls that reminded me why I love what I do. I was talking with Madi Waggoner from buildingremote.co. Within a few minutes, we both realized that we were solving the same core problem from different angles. And so she helps entrepreneurs fire themselves from their daily operations so that they can focus on what they love and actually take time off. Man, it's awesome. I help creators build systems that eliminate chaos and create sustainable growth.
So the light bulb moment was this, the most creative professionals that I work with have become the bottleneck in their own business. They can't take a vacation, they can't delegate meaningful work, and they're drowning in the day-to-day operations of what was supposed to be their dream business. So if that sounds familiar, today's conversation is gonna change that. So let's get to the interview right now that I had with Madi Waggoner.
All right, Madi, welcome to the Creativity Made Easy podcast. I'm so happy to have you here.
Thanks, Dustin, for having me on. I'm so excited for our conversation today.
Yeah, as we already said in the intro, Madi owns her own business, Building Remote. And we met a couple of months ago and now have some similar circles. But Madi, why don't you start by sharing with our viewers and listeners, tell us about Building Remote and what led you to focus on helping entrepreneurs fire themselves from their daily operations.
I love it. Yeah. So I work with founders and their teams primarily, and it started out by when I worked in tech startups, I worked directly with these founders and noticed how difficult it was for them to be able to take time off. And by working with them directly, I was able to help streamline operations, including with customers and internal team members and creating things like SOPs, standard operating procedures, to help them be able to get things out of their head and pass the work off to other people so that they could actually take time off.
And the first startup I worked in, actually, I was there for a few years. And we did so well with this process that that founder was actually able to take a full month fully disconnected with maybe two check-ins during that entire time, which is kind of unheard of in tech startups, especially at that stage. And I loved getting to make that work possible. And especially as I've become a parent, and had other things happen in my personal life and seen how things have happened in my clients' personal lives. I've loved being able to give them that time back to not just spend in their business, but also on the personal parts of their lives as well.
Yeah. We talk a lot on this podcast about margin and I love that you're talking about giving them back their time. And when you do that, you work through these four pillars with your clients. Can you kind of walk us through what those four pillars are and why is that structure so important for professionals in general?
Yeah, so it's my LIFT framework, L-I-F-T. It's leader, infrastructure, fuel and team. And the leader one is first there because we have to first work on mindset and how the leader acts in terms of how they delegate, in terms of how they communicate, in terms of even how they think about themselves. Infrastructure is more about the systems, the tools, the meeting cadences, the communication that we have in place.
Fuel is actually fairly detailed in the number of pieces that it encompasses. Some of it is marketing, some of it is sales, other things around customer and client delivery and the experience that we deliver. I don't actually solve for marketing and sales, but I want to call that out when I work with clients. And I have referral partners who I can connect them to in the case that they're really glaring issues that need someone's specific help. And then the last one, T is team.
And team is all about, we have the right people in place? What's our hiring process, our off-boarding process, which most people don't think about, and how are we working together as a team? And there's a lot of other things within that as well that a lot of people honestly don't consider when they start hiring and building up the number of people that are working with them. And so covering all of these different pieces, the reason why I have it structured this way is it's LIFT. A rising tide lifts all boats in the same way we have to address all of these issues if we're going to have a successful business.
Yeah, I love it. Let's walk through a couple of those for a second. Let's focus in on leadership for a second, cause my clients and the people that I talk to in the creative industry, a lot of them are moving from what I call from maker to manager. Right. And so they're going from being the doer to the leader. So what does that look like when you're working with these leaders of organizations? How do you get them to transition to make that transition from maker to manager or from doer to leader?
Yeah, I call it the solopreneur to CEO shift. And it's really about when you're starting your business, like you said, you are the doer. You're the one who's literally doing everything. You're responding to emails. You're the one doing the work you're delivering. You're the one getting on calls. And when we start making the shift, we have to stop just jumping into everything. One of the things that I like to call out in, I'll sit in on client team meetings, for example, this is one of the core things I like to do. And when the team is talking about something, I often hear the founder say, oh, I'll handle that, I'll handle that, I'll handle that. I say, we have to change that mindset of you are not the one who is actively always taking things on. It is looking for someone on your team who can take it. So instead of saying it like that, I work with the founder and their team to help normalize the shift of the founder is not the one who should be taking everything on. Either you should be volunteering or the founder should be saying, who can take this on? And that's one of the first shifts that we have to make in how are we actively taking work off of our plates and also not adding it to our plate.
So when they're going through that transition of changing, not, you know, how can I take this on? But, but who can I not how, but who, right? When they're doing that transition, I imagine there's a lot of anxiety in them about losing a little bit of quality control. How do you help kind of guide them through that and see that differently?
Yeah, I was actually just working with a client on this recently and walking them through the process I recommend. So a lot of times when people think about delegation, it's I'm just going to write a message to someone on my team and they're going to handle it. But the problem is that they're likely going to handle it differently than you would, especially if they're new to your team. So what I recommend is that when you delegate, you start off with a very specific process.
So first of all, you try and get buy-in. Are they even interested in doing this? In some cases, if it's a growth area for them, if they haven't done this work before, if you have a conversation around, hey, I want to look for someone to take this on, I thought you'd be a great fit. But I want to understand, is this something that you even are interested in? Most of the time, they are. I rarely hear like, oh no, I don't want to touch that. But it's good for you to know upfront because if they're not interested at all, you might not get the best work out of them. So that's the first step.
And then when you're actively delegating, I actually recommend that you use a couple of different types of templates that I have. It's making sure that you share context with them around who is this for? Why are we doing this? What are the parameters that you expect for completing this work for it to be high quality? What's the timeline? And then any other context around, you know, I've had a conversation with this person, here's some more information that you should know, etc, etc, to make sure that whoever you're handing it off to has the information that you do. So have all of that organized in that way.
And then after you do that, I recommend that you have checkpoints. So the first time you hand work off to someone like this, you ask them to go do the first step. Maybe that's writing an outline. Maybe that's doing a wireframe, like if they're designing a website, for example. Anything that is the first step that you can check with them and meet with them and say, walk me through your thought process, because you want to first understand how they made their decisions to get them to where they are, and then coach them. And then if they made any kind of missteps or they're going along the wrong direction, you can then help shift them back onto the right path. And you just keep doing that through the process. And then by the time you get to the end, you're going to have a much higher quality result. And they're going to understand how you think about your process in this particular instance.
I love it. I love that you're thinking through the, we always talk to my clients about the focus funnel, right? Like, Hey, we're going to go through and we're going to automate, eliminate or delegate some things. And I think leaders need to understand that. Let's get into the infrastructure just a little bit. So we talked about, need to have this delegation system, this delegation process down pat. What are some other systems that need to be in place before a founder can successfully step back from those daily operations?
Yeah, one that is somewhat related still to leader is actually getting really clear on mission, vision and values. And I explicitly like to focus on values because it's a decision making tool. So for example, I used to work for one startup and they focused very heavily on this value of respect your audience. And it wasn't just thinking about like marketing material where you're sending it out to an audience, but it's thinking about the individual person who is going to be using or responding to whatever you send to them. And in some cases, that can be your future self. And so we want to respect who that is and make sure we're very, very clear. So it's things like that that help your team to be able to make decisions on your behalf. And you have to get that out of your head in order for that to happen.
So there are a number of different pieces that's more communication and information sharing. So SOPs can be a part of this. And one thing I recommend is that when you're starting to try and distance yourself from that day-to-day work and be able to take vacation, you want to involve your team in creating those resources. So I don't actually recommend that founders write out standard operating procedures. I recommend that they create something like a loom video or even a voice note, depending on what the task is and give that to the team member and ask them to create the written material because then you're delegating, you're moving that off from your plate so you don't have to do the work, but you're also creating buy-in for that person because it's something that they created. It's their resource.
So they're more interested in than using it and encouraging their team members to use it as well. Because what I've seen with some clients, I was consulting with someone recently on this, they were creating all the SOPs and having a hard time getting their team to use it. I said, well, they don't have to buy in. So we have to psychologically change it so that they're more interested in that.
So that's some of the informational infrastructure. Some of the other pieces that are more like team related are, are you doing team meetings? Are you doing one-on-ones with your team? Are you doing what a lot of like agile companies, like software companies use retrospectives. So that's after a task or a project or an event that you run, have questions, have a little meeting and have asked some questions that go through what went well, what didn't go well, and what should we do differently next time so that you're systematically capturing this information so that you can continue to iterate and make things better.
One-on-ones are really important because if you're not doing these one-on-one times with your team, especially if you're a remote organization, you're missing out on some really key information and connection points. And all this is really important towards this whole business of everybody rowing together in the same direction. And then some other more like tactical tool oriented systems kind of varies between different companies, but some basic ones are a project management tool. I personally really appreciate Asana as we've talked about. Others are like ClickUp. Another one that I've heard good things about is Motion, which actually puts tasks onto individuals calendars, which can be helpful. So that's one part of the infrastructure. Other communication tools like Slack. I'm a big believer in Slack. I do not like Microsoft Teams. It's not designed for strong remote communication.
And then the other thing that I won't dive too deeply into is automations and how you use your different tools to deliver information and material to clients. For example, a lot of people don't think about the experience that they're creating for their clients when they onboard them. I have signed into multiple communities and joined different programs and I'm always disappointed when they haven't put thought into that onboarding because it can make or break trust in that experience, especially if you're investing time or money into it. So all of that is infrastructure related.
Yeah, I love it. You started to dive into a little bit of the, or a lot of it honestly, of the team aspect. Let's break into the team a little bit and how do we help owners build teams? So we talk about one-on-ones are super important, right? But good leaders are good team builders naturally. They should be anyway. So what can leaders or business owners or founders do to build a team that can really execute their vision without that constant oversight, especially in a remote environment?
Yeah. So I've hired over 50 roles for clients. And what I've found when they start working with me, when they've tried hiring before, is they're not starting out on the right foot. And if you want to have strong team members, you have to start the hiring process off well. And part of that is getting extremely clear on exactly what you need. Don't just say, Oh, I need help. I need an assistant. No, you need to be more strategic in how you're actually breaking out what you need to hand off to this person.
So a quick way that for you to do this is to just sit down and brain dump essentially, what do I like doing? What do I not like doing? What do I procrastinate on is a big one. And what am I not good at? Anything that isn't in your zone of genius, you should consider handing off to this person. Now, with that being said, not everything can go on that job description because you can't ask one person to do the jobs of 10 people. So you have to be realistic about that. But all of that clarity then feeds into a job description that you post. And that job description should not just be a replica of that list, but it should actually be designed in a way to help attract the right candidates.
So for me, I want driven people when I hire. So I structure the job description in a way to be attractive to that kind of person. For me personally, I also am big on like career development. So I list that in benefits when I'm hiring for roles for me of, we will have conversations with you about your growth plan and where you want to go. I do not care if this is a contract 1099 role. I still do this. That kind of thing can help show people who I am.
And something else that I'm starting to play around with is using voice and video on job descriptions as well. Because so often job descriptions are just written, but we live in a world, especially these days, where when you're working remotely, we do a lot of that through video and voice. So if we can bring in some of that personality, do you see the difference of how much more intentional this is just even at this point? We haven't even gotten to applications yet.
And so after that is applications that help to filter out the wrong applicants and bring in the right ones and keep them going through the process. Same with interviews. And when you're going through this entire process, you have to, again, think about the candidate experience, because if they don't have a good experience, if they're strong people, they have other options. They're not going to keep bothering spending time with you or prepping for interviews.
And so going through that whole process, that will help you to bring in the right people. And then once you have them on your team, a lot of it, again, is intentionality. When you're working in a remote environment, we have to be intentional. I've heard so many arguments about, you can't build culture remotely the same as you can in the office. My argument is you can't build it lazy like you can in the office. You have to be intentional.
So when we bring on new team members, I always encourage a really strong onboarding process. So that starts off with a kickoff call with their manager. You do check-in calls during the first week. You give them action items. So it's a win for them and a win for you in the first week. And then you keep going through that process, kind of backing off a little bit as you go over the next month, two months, depending on the role. And through all of that, we are building and establishing that this is how we do things. I want your opinion. I'm going to ask you questions through these conversations around, what are you seeing that is broken or is confusing? I want to know that from the get-go. So we're building that trust.
And also through all of that, if we're doing the onboarding process intentionally and the hiring process intentionally, they will have learned already about how we operate here because we will have shared that through the process, just kind of in the different things we do, but also actively proactively sharing the mission, vision, values, the examples, loom videos that we might want them to turn into SOPs at the beginning. They get all of that from the get-go.
And it creates this really solid foundation so that as we start adding in other pieces, like doing retrospectives on a project, when you ask at that point after doing all this work, what didn't go well with this, they feel more comfortable, like they can own up to mistakes they personally made and say, I did this, this is what happened. This is how we can adjust this going forward so it's stronger. And that all of those steps help to feed into a strong team that not only allow you to delegate to them, but will be more proactive in taking things off of your plate.
Yeah, that's a great four minute clip on how to build successful teams. I love it so much. So we cross paths originally and started having conversations because we solve similar problems from different angles and different clients. Can you talk to me about how like partnerships fit into scaling businesses as businesses and founders are trying to grow their business.
Yeah. It's funny because I've worked or had conversations with a number of different consultants who are clearly very good at the work they do, but we all are going to be experts in some areas and not able to touch others and referral partnerships and partnerships in general can be so beneficial for our credibility by saying, I don't do this, but I have this partner here who you can work with who's fantastic in this area. Here, I'll make an introduction to you. That can make the other person on the other end of the call or if you're in person meeting, understand that you have things together. You are their guide. You will walk them through what needs to happen. You will connect them to the right people. And the more that you can build strong networks like that, the easier it is for you to scale because it builds trust with your clients. And then you can have these referral partnerships between yourself and other people who can send you work. And that all of that feeds into being able to scale because you can't do everything yourself, whether it's lead generation, whether it's completing work and having the right people in your network, in your team that you know and build relationships with just helps you to be able to accelerate your results that much faster.
Yeah. I've got two more questions for you. And this next one's personal. This is just for me. No one else is listening. If someone right now recognizes that they're the bottleneck in their business, who has two thumbs and is the bottleneck, right? What's the very first step they should take.
So I always say that you should first celebrate that you're self-aware enough in order to recognize that because I personally, right? Exactly. Celebrate it. I personally cannot work with founders unless they're at that point. I can try and have conversations with them, but they will not be ready to work with me until they recognize that they're part of the problem. And so once you see that, we can start addressing, where are the areas that this is breaking down? What are the small things we can start doing? And I do really start with small quick wins. Starting with team meetings, like I mentioned, that's just one shift. We bring the team in so they can call you out, especially if you've already developed some of that trust. Then it's easier for your team to be like, oh, hold on, you're not supposed to do that. Madi said so.
And I teach them how to do that. So if I start hearing you pick up, say, Oh, I'm gonna I'll take care of this. I say, Ah, we're not gonna do that. One of your team members needs to handle that. And then the other thing too, is that oftentimes, if you've developed yourself as the bottleneck, we have to start changing your team's perspective of how exactly they handle problems. So if they're used to coming to you and saying, Hey, I found this problem, what do we do? And you normally give them the answer.
One really quick, easy win to start changing this for all of you is to instead turn the question back on them and say, well, what would you do? How would you approach this? Go do a little bit of research or create an outline or whatever you want to do to address this, and then come back to me and then we can talk about it. That can throw people off guard at first, but if you just keep repeating it and you say, this is how we're trying to change things, I'm trying to enable you and I'm trying to get myself out from being a bottleneck, so this is what I'm going to start doing, it starts to change their behavior without you really having to do much except ask a question. And that can make a huge difference towards shifting that for all of you.
I love it so much. Well, where can people learn more about building remote and potentially working with you?
Yeah. So I'm active on LinkedIn. You can look for Madi Waggoner and I'll pop up and then otherwise buildingremote.co. There's no M at the end. Some people miss that. So buildingremote.co.
I love it. Madi, thanks so much for your time. I know this information is going to be invaluable to our audience and I'm gonna go back and listen to it and recommend everybody listen to this at least twice. Maybe half speak because there's a lot of really good information, but thank you so much for your time.
Thanks for having me on Dustin.
So here are a few things that you need to do to start freeing yourself up from being the bottleneck in your business. First, just like she had me do, celebrate the awareness, right? If you recognize the problem, you're already ahead of most founders.
Secondly, audit your delegation habits this week. Start paying attention to how often you say, I'll handle that in meetings or conversations. Madi's right when we do this unconsciously and every time you catch yourself volunteering to take something on pause and ask who on my team could handle this instead.
Third, implement the question flip immediately. I love this and can't wait to use it. The next time someone brings you a problem don't give them the answer ask them what would you do or how would you approach this. Yes it might feel uncomfortable at first but you're training both yourself and your team to think differently about problem solving.
Fourth, start small with your very own LIFT framework assessment. Look at Madi's four pillars, leader, infrastructure, fuel, and team. I love how simple that is. Pick one that feels like your biggest gap right now and identify just one small improvement that you can make this month. Don't try to fix everything at once.
And lastly, involve your team in creating your systems. Instead of writing all those SOPs yourself, just record a quick loom video. We talk about that tool on here all the time and explain the process and have your team member turn it into written documentation or visual representation, whatever it is that you may need. And they'll be more invested in using something that they actually helped create.
Remember, building a business that can run without you isn't about working less. It's about working on the right things. And you can find more resources for scaling your creative business at dustinpead.com slash free. I'll have links in the show description to where you can find Madi and her business and on LinkedIn as well.
But the truth is this, that your creative business will only scale as far as your systems allow it to. If you're still the bottleneck, you're not just limiting your business growth, you're limiting your ability to do your best creative work. Take Madi's advice seriously and start with one small step toward delegation. Document everything and remember that firing yourself from daily operations doesn't mean losing control. It means getting the freedom to focus on what only you can do.
If today's conversation resonated with you at all, head over to dustinpead.com, download free frameworks and follow us on at Dustin Pead on social media. Most importantly, pick one thing from today's action list and implement it this week. I would love to work with you as well. If you'd like to do that, you can follow me or find me at dustinpead.com. Click on the contact button and hop on my calendar for a free 30 minute strategy session. I cannot wait to be back with you next week on Creativity Made Easy. Have a great week.