Now & Center: Entrepreneurial Voices from the Margin

Spite, Inclusive Workplaces, and Personal Branding with Jessi Burg, Founder of Outgrow Your Garage

October 11, 2022 Karen Bartlett Episode 25
Now & Center: Entrepreneurial Voices from the Margin
Spite, Inclusive Workplaces, and Personal Branding with Jessi Burg, Founder of Outgrow Your Garage
Show Notes Transcript

Episode Description:  

Karen talks with Jessi Burg, Founder of Outgrow Your Garage, about doing things out of spite, using what we’re good at to solve problems, and the harms of the “just work harder” narrative.  They discuss Jessi’s mission to create truly inclusive workplaces, including all stakeholders and moving beyond demographic considerations, and the impacts of intersectional identities on her business experience.  Karen and Jessi have a coaching conversation around personal branding versus business branding and not getting caught in the either/or paradigm.


Schedule an Exploratory Call with Karen:

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Learn more about Outgrow Your Garage:

Connect with Jessi Burg:

Connect with Carin Huebner at Public Good Media:

Original music credit goes to DJ Ishe:



Hello everyone and welcome to this week's session of the Now & Center podcast. I am here today with Jessi Burg. She's the founder of Outgrow Your Garage and it's kind of funny we were just talking, like we actually have met post covid shutdown and so we have never actually met in person and we were just talking about, you know, how interesting this world is. It's interesting because even though we met quite some time ago, we only had our first one on one conversation very recently. So it's been super fun getting to know you better and I'm really excited to have you here today. So, welcome.


Jessi Burg

I am excited to be here and it is really nice to have a little bit of one on one conversation. I feel like there's a lot of people that I've met kind of in passing in these networking groups and online things or in passing somewhere else and I feel like I’m still catching up with those one on one conversations.



Yeah, yeah, yeah, it's really fun. I can't even remember where we were and how it happened but anyway I'm really glad that we did it. So, very fun and I think everybody will be in for a real treat today. I think that there's some really aligned and interesting things that I know you're wondering about and musing on and working out like how to put these things into place in business and that are really similar to what I'm doing, what we're doing over here at Kite and Dart. So this should be a great conversation. With that, would you please share with us about Outgrow Your Garage, what your business does, the difference you're making and anything else you'd like to share with us?


Jessi Burg

I founded Outgrow Your Garage in the same way that I do a lot of things in my life, which is largely out of spite that no one is meeting my needs. And that's a very common motivating factor for me as a person who grew up with not a lot of money in my household, as a person who grew up in a place that didn't have a ton of resources. It was really common for some to be like “oh no, you can't do that” or “no, we don't have access to that” or “no, you know this sort of thing” and that has really largely carried on into my adulthood where I got shut out of opportunities a lot because I don't have the hypothetical rich, white, uncle to open doors for me.

So getting told I don't have access or I can't do things is a really good way for me to go “you just watch me.” So what happened with Outgrow Your Garage is I had started a landscaping company (also largely out of spite) where I had been working in environmental education and urban farming. I had spent years working in these seasonal industries which I loved but the downside to teaching children skills outdoors is that it does not pay you a livable wage and it's really hard to make a living in that.

So I really wanted something that would let me keep that seasonal lifestyle and also make enough money to have a savings account and I got a lot of “yeah, you can't do that you have to choose one or the other” and I was like “well that's dumb”. So I started a landscaping company that gave me a savings account and a nice seasonal lifestyle. 

So then fast forward a couple of years, I wanted to grow that landscaping company and I went “great, I would like to know what resources are available for my seasonal business that hasn't existed for a ton. We don't really have any assets or anything we can leverage against. How do I hire staff? How do I set up all these backend business pieces for this business that is starting to gain some traction, starting to gain some money?” Everybody went “well, you can come to this webinar”. And I was like “great well that webinar is happening at exactly the same times that my clients are free for estimates so that's not going to work” and they would say “great here's this hiring resource” and I'd go “great how does that apply to seasonal workers?” and they'd go “uhhh”. And everything was kind of like that. 

I ran into that with service-based business- “how do I price my services?” and people would go “well it really depends… because we don't know” and I'd be like “awesome, that's not helpful. I also don't know so this is why I'm asking you”. I kept running into this in every area of my business. How do I grow a service business in a way that meshes with my values? I started to find those answers and as I found those answers, (I am a fairly natural, we’ll politely call it “opinionated” person), I started talking about it in public. “Here are the struggles I'm having here's how I'm solving it.” 

So I set up a staff training method and hiring process that meant my landscaping company didn't have any turnover. I started getting some attention for that. I started talking about how I priced my services and started networking with other entrepreneurs to show those secrets of “how you price services in a way that allows for enough money to be able to pay your staff a living wage?” All these pieces and then, some of us might remember in March of 2020 the whole world went really bonkers but we had this pandemic and what happened as a result of that is I had to do some really hard thinking about how did I want to handle my staff? How did I want to handle my future? How did I want to handle the rising cost of living in the Denver metro area where I was at that time?  And I spent all of 2020 thinking about that and in 2021 I decided “you know what? I've been doing this side coaching and I've been doing these conversations about how do you run an ethical service-based business? How do you build an inclusive work environment when you have shift work? How do you handle this need for remote work at a job that doesn't really allow for remote workers because you can't shovel rocks remotely. How do you do this?” 

So I spent this whole year thinking about these and I went “you know what? I'm gonna launch Outgrow Your Garage and I'm gonna launch a business that specifically does business development and learning for service-based businesses that just don't have access in other places/” That is where Outgrow Your Garage started and now we have online courses in a bunch of subjects, they are all downloadable, you can listen to them as audio files, you can watch them as videos with or without captions, you can read them as transcripts. So whatever your learning style and free time is, you have access to this learning.

Also everything is broken down into these little short learning modules. So on our pricing course (because, of course, I wrote a course on pricing) pricing and basic financial literacy for business owners is approximately an hour and a half worth of content, but not a single no single piece of information takes more than 10 minutes to get through right? So we've got ten ten minute videos or less than 10 minutes that comprise several different modules and then every module has an activity so you can listen to it, watch it, read it, whatever works for you and then do the activity. So you're able to apply that immediately to your business. 

And so really working on setting things up for “how do we hit a bunch of different learning styles for a set of people who just don't run businesses in a way that business development typically talks about?” People who tend to start these businesses also tend to do so because service-based businesses don't require a lot of capital to set up. You can start a landscaping business or a house cleaning business or a graphic designer business with yourself and a car or a computer right? So that capital need is really low. So people who don't have money tend to start service-based businesses as a method of getting it. So how do we help these businesses grow which then in turn allows them to hire more people and generate stronger communities that don't have access to huge sums of capital for any number of reasons. So that's what I do. That's how Outgrow Your Garage happened, but a lot of it is because I'm mad about the state of the world and I just need things to do with that.



Yeah, isn't that like necessity is the mother of invention right? And it's like when you're in a system that isn't meant to set you up for success, isn't meant to help you get ahead, doesn't honor who you are, which we'll get to that conversation later I know, but it's like yeah, that makes perfect sense. I love the opinions and the defiance and the spite and all of that because you know I do think that, you know I know that you're as interested in creating a world that works in a lot of different ways than what we have right now you're as interested in that as I am and it's going to take all of us being willing to do that to stand up and and be defiant and all of those things. So yes, I love it.


Jessi Burg

Yeah I always think some people can be the Dalai Lama and they can sit there and they can be very calm and they can meditate their way… I'm not that person and so somebody has to be the calm and create change in spaces where calm is required and some people have to be like “I'm mad and I'm going to do action, I'm going to give you a channel for that anger” and so I think it really does take all of us you're right.



Yeah, yeah, well and I also just want to call it that I really appreciate just who you're serving right? And it's so funny because like what you do and what I do at Kite & Dart is very similar with a bit of a different focus right? This isn't about competition right? Like who cares, there's plenty of folks out there who are trying to start and run businesses who can you support but the whole you know we kind of call them nontraditional business owners which is kind of a weird misnomer because I think they're actually a lot of folks with identities who really very commonly do start businesses but they're not the ones who are like the ones with the capital, the ones who have access to those resources, the ones who are quote unquote supposed to be in business. 

You know we work with those folks too and it's interesting because you know I work with service-based businesses too but most of my clients are consultants right? And a lot of your clients are in the trades, and what your clients need and what my clients need, there might be some overlap but there's also a lot of differences and really working to create your content to create your support to work for the folks that you're trying to reach like you know so much from having run that landscaping business that's going to make you so much more helpful and supportive to folks who are trying to run similar businesses. So I just really appreciate it and it’s like we're all coming at it from these different angles and we're gonna get there. But yeah, yeah.


Jessi Burg

Yeah, what I think it's important to know what you're good at too. I don't ever want to do coaching right? I don't love working one on one with people. I don't love doing those kinds of visioning pieces or really figuring out how your values show up in your business like I don't love those individual business pieces. What I do love are operations and logistics. And that's great, it works out really well for me, it works great for my desire to create courses that can help people. I can kind of always move on to the next thing or chase down the next rabbit hole.



Yeah, got it.


Jessi Burg

I think that's a really important distinction to make too is that there are lots of different ways to solve the same problem and lots of different facets to come at it and I think that's what's so beautiful about the number of people who are working in this space right now where even if we have clients that are comparable, you're doing a lot more of that 1 on 1 guidance and so somebody needs to do that when you have questions. So I really dream of this world of where Outgrow Your Garage has this beautiful array of people that we just send people out to regardless of what you're looking for. 

If you're looking for a bookkeeper, you're looking for a graphic design, or you're looking for a coach, whatever you're looking for you take the appropriate Outgrow Your Garage course to help you figure out what the right questions are to ask? What are the questions I need to ask? What are the logistical pieces I need to have in place? Where am I at now? And then you take this set of information to a person who can help you figure out what to do with it and help you find answers to the questions that you now know you have. You can figure out how to implement those on an operation scale and so really work on those pieces. And then also it's nice for the DIYers of the world- some people really want somebody to come in and help with that and some people just want to watch an online course and then be able to implement it on their own and so having all those different pieces I think its a huge part of creating a more inclusive entrepreneur space in general



Yeah, yeah, totally. Like we do that so much too at Kite & Dart like there's a lot of things that we do for our clients, but then there's always things where we're like “Nope that's not in our wheelhouse” and so the coming from that strengths based approach is really important. And even the organic way that it came about that you started Outgrow Your Garage I really love because I think that um, really aligning your business to those strengths, those passions you know and when it happens in this organic way, it's like that's because alignment, right? You know you're infusing your values and you're using your skills and talents and gifts to help people and that that's the biggest contribution you can be and while having a landscaping business is a contribution and it's great and it's aligned, I love how you sort of organically through starting that business ended up being like “there's this bigger way I can help people and I'm going to go do that because that's actually more of a contribution to other people.” So I love that about your story, your journey. 

So I'd love to bring in what you talked a few minutes ago about kind of like inclusive workspaces right? And even how when you were branding the landscaping business how you were trying to have an inclusive workspace, have it you know, paying people fair wages. I mean there's so much it's more than just inclusive but it's like having inclusive workspaces honoring who people are making sure they get a living wage like there's so much juicy stuff there. So um, will you just kind of share with us about yeah, whatever you want to share with us about that topic I'd love to hear your thoughts and what you've what you've been chewing on.


Jessi Burg

Ah, yeah, yeah, so I think this is something I think about a lot . And I think about it particularly because I spend a lot of my time with blue collar tradespeople. And I live out in western Colorado in a farmtown and so the people I interact with a lot are, in the place that I live, farmers. We live in a rural area and so I have this really wildly different set of people that I interact with a lot and then I have another set of people over here that I interact with who are largely college educated, they're really interested in sustainability on the academic side, they're really interested in things like corporate social responsibility and these things that are really foreign to your average plumber. 

And so I spent a lot of time thinking about how to balance those worlds and how to bring those things together. When I think about inclusivity I think about “how do you create a workspace that works within your community and for the population of people that you're trying to serve and also for the people who come and work for you?”  And I think one of the things that gets rolled into inclusivity a lot is we think it's only about race or we think it's only about gender, we think it's only about age, or it's kind of about these demographic pieces. But really, it's about how do you find the best person for the job? But also how do you make sure your applicant pool is going to get you to the best person for the job?

 And there's a couple of things that I think are really important to do that from the business side and 1 is to make sure that your job description matches the thing that you're hiring for. I think that's a huge piece of inclusivity that kind of gets missed where we have a lot of staff turnover in places or we have a lot of people who come to the interview and then don't take the position, in a lot of industries, not just trades industries but across the board. And it's because what you're hiring for and what you're actually looking for are not necessarily the same thing. And so really making sure that the job description, the person who will actually be supervising that employee, and the person who's doing the hiring all agree on what that job is, what the key responsibilities are, what it pays, and having a conversation on what reasonable accommodations for that position are. Right? 

So, can it be done remotely some of the time? Can you offset a start time so somebody can drop off their kids? Can you end work early some days so they can pick up their kids? Can you set it up in a way that works for somebody who is dyslexic? Can you set it up in such a way that somebody who is in a wheelchair could do this job? Can you set it up in a way that will work for whatever else comes up right? So have some conversations about that and you can pick some really easy things of “okay, could a person in a wheelchair do this job? What are the things that we think would cause problems with that, right? What if somebody was deaf? What if somebody was blind? And so you can kind of run through some of these pieces and that can really help identify some of the ways that you are lacking in inclusivity, even if you think you're generally an inclusive environment. 

And the other thing that I think is true is that if you have the option where you have two people of reasonably close qualified backgrounds for the same position and one of those is of a historically excluded population, always take the one that is of the historically excluded population. Because, particularly if you don't have very many people who aren't white, or who aren't male, or who aren't whatever, on your team and the reason for that is because the more diversity you have when somebody looks up your company on their website, on Linkedin, sees them out and about, the more diversity you're going to get in your hiring applicants. A lot of people don't want to be the first. I don't want to be the only woman on that team, I don't want to be the only person of color on that team, I don't know if this space is safe for queer people, so any of those kinds of different pieces think about what it looks like.

There are lots of resources for that and if you really want to do DEI consulting, there's plenty of people around who will help with that and give you really specific things on what will work within your organization. But really thinking about what are the things that people want and one of the best resources companies have in creating an inclusive work environment is your existing staff.

What are things that they wish you had to make their work life balance easier? Because I think the biggest thing we forget when we talk about how staffing works and how we create these inclusive work environments is that a) you can ask your existing staff, you have this great pool of resources of people who know your company, have a good idea of what's reasonable, what's not, what would be able to happen within a given department. But also they have a life, and that life is more important than your business to those employees. 

So if you say to them “how can we honor your outside life even when you're at work and make this easier on you? What do you need in order to be a happy, fulfilled person and how can we contribute to that?” Some places are going to be like “yeah, that's a lot of hippie stuff I just want to clock in and clock out, do my thing.” But some people aren't, and some people are going to say “oh yeah, it would be really great if I could do my emails from home on Thursday afternoons because that's the day that my mom has her doctor's appointments and it'd be really great if I could take 2 hours off in the middle of the day to take my mom to her doctor's appointments, come home make sure that she is settled, all the things are good, and then I can check my emails after that.” Whatever, like everybody has those things. I think finding good ways for people to caretake for the other humans in their life is one of the highest impact ways to make your staff feel valued whether that's spouses, whether that's children, whether that's family members, whatever. Everybody has people that they care about and sometimes need to spend time with.



Yeah, yeah, I love so much how you know you're talking about that inclusivity goes so far beyond demographics and I think that that's just so important I want to call that out like again because yeah, there is inclusivity around demographics and there's so much more, right? We live in this society that's very dehumanizing and so even just putting people into categories there are different experiences based on certain identities, but even within that every individual is different. So you know there's this level of like all humans need to just be this way and then there's like okay people in these different groups and then there's just like the individual level right? and all of those levels are important. I think that's the level at which we really need to get this conversation. 

And I also like what you were sharing about those ideas which, just yes for all of that, I was thinking about because we've been conditioned to be in this system where there's one right way, where there's an ideal that we're all supposed to be reaching towards. I think it's super interesting and this has just been the thing that I feel like I've learned through what we're doing at Kite & Dart because we're trying to do that for ourselves internally and we try to support our clients as well with “what does that mean for them?” Because of the conditioning that we have towards this 1 right way, it can take a lot of time and reflection and processing and self-awareness building for people to even figure out what they need or how they work best or you know what I mean. 

Like for example I work with quite a few clients who are neuro divergent and I can't tell you how many times I've heard folks who are neuro divergent talk about a lack of motivation or procrastination. And I don't want to discount the impacts that different ways of being neuro divergent impact you but like I will find folks who are doing things in their business that they're not good at and they don't want to do. And the narrative that they're telling themselves is that they're procrastinating. They're not motivated like there's something wrong with them and that's not it. 

They shouldn't be doing that thing because they're not good at it and they don't want to do it anyway but we've been given a narrative around “this is how business is supposed to be done. This is what a business owner needs to do.” If you're not doing it you need to change yourself, you need to work harder, you need to overcome and change something about you. When I think the opposite is true, that it's not changing the human, it's changing the structure of the work environment to work for each individual human. That's so much of what I'm hearing, but I do think that it's such an uncovering process because of how we've been conditioned to try to stick us into the mold, you know.


Jessi Burg

Yeah, and one of the things that I think is really true and I love that you bring up this idea of like “here's what we're supposed to do, we're supposed to work harder” because there's that running joke about “start a small business, work more hours, and get paid less” which is my least favorite thing that anybody says about small businesses across the board.





Jessi Burg

And I really do exclusively work pretty closely with small businesses. I know nothing about startups and I think this is a really important distinction to make that we forget a lot when we talk about business. When we say business in a broad category a lot of times what we think of is tech companies and corporations. And we don't think about small businesses which are these kind of main street businesses that are really vital to the communities that they exist in, but there's a limit on how big they can get. There's a limit to the amount of funding that they have. There's a limit to the growth that they can do either because it's just this little family run business that kind of bops along and does its thing or because they don't want to franchise, or they don't want to get bigger than where they’re at, or because it's the kind of business where in order to scale, you have to hire and that's hard. 

It's hard to find capital and finances on it. But I think this distinction between a startup, an infinitely scalable business that you can grow to whatever size, that goes after things like venture capital funding and large grants and all these different pieces, and a startup which is typically going to be a small business with less than 5 employees is going to be location specific, is going to have a different set of pieces and it's not going to grow in the same way, it's not going to have that hockey stick growth that we really associate with startups. That small business narrative around “I just have to work harder and I'll be successful” I think is really harmful and damaging because if you set your operations up well, you set your pricing well, you understand the business side of it, it doesn't have to be this giant struggle. The first year or two is definitely going to be hard. 


Jessi Burg

I lost friends while starting my first business absolutely because they were like “I haven't seen you in two years. Why don't you have time for me?” And I'm like “because I'm running a business and I don't have time” and I think that happens a lot. But after that at some point you hire other people, you outsource the things that you're not good at and you don't want to do, and it's okay to outsource those things that you're not good at and you don't want to do. Somewhere during the pandemic I read a quote, I'm also pretty neuro divergent. I am both dyslexic and I have pretty wicked ADHD, I'm very very prone to the stereotypical type of ADHD where I'm like “oh squirrel” I can't look at the thing, I can't focus, I can't stay on topic. Some days I'm pretty solid and I've worked out my own coping mechanisms but part of that is that I have really had to think about what can I do and what can't I do and how do I outsource those things off my plate because “you can't try harder at trying harder”. That's not how it works, like you have to at some point figure out how to alleviate that pressure on yourself. So for anybody, but particularly within your neuro divergent community, we're not existing in a world that was built for us.





Jessi Burg

And that's true for a whole lot of people so when you're thinking about that, what are the things that would make it easier for you? For me, I have a person in Outgrow Your Garage who goes through and handles a lot of that detail oriented stuff, right? She drafts emails for me and then leaves them in my draft folder so I don't forget to send a follow up email. She checks and reads through my newsletters to make sure that there's stuff going on, she kind of handles a lot of these backend things. She builds presentations for me so I don't start on the morning of the presentation and go “oh shoot I forgot I was doing this thing until today I don't have my powerpoint ready” and so she builds all that at the backend so she takes care of all those pieces so they're done.





Jessi Burg

And she loves that she does not have to do a lot of the overarching visioning and direction and all the networking and all that public facing piece, and I love that I don't have to do a lot of these detail oriented tedious things that are really really hard for me. And so having those pieces I'm a firm believer that every business, service based or not, your first hire is always going to be one of two things: You're either going to hire somebody who does whatever your business does- something who is creating product, somebody who is working billable hours, somebody who was doing the thing that your business does, or you're going to hire somebody to do office manager stuff, right? Help answer the phone, answer emails, update your social media, kind of keep track of some of these like logistical pieces. Every business is going to hire one or the other for their first hire because you're going to either need more time to do billable hours and actual product building work, or you're going to need somebody who's helping you take care of those backend logistical details.



Yeah, yeah, and with that narrative too around like different cultures, there's corporate, there's startups, there's small business, right? And we work with small businesses as well at Kite & Dart and I think that it's so true the rugged individualism is a thing and so I think people do feel like they have to do it themselves and it can be really scary to look at hiring others, right? When you don't have the same resources, when you don't have the same privileges to be able to go pay other people to do things, that's a really daunting thing to take on and so we're always really even looking at how can folks get really creative in the ways you're talking about right? 

Whether it's hiring someone to serve clients, or hiring someone on the backend kind of things, there will be times where I'll even be working with one of my clients and it's like maybe it's more a matter of hiring someone to clean your house or to do your yard work or whatever so that you get that time freed up to really be in the business and that if we look very holistically at their lives which goes back to what you were talking about with an inclusive work environment right? But as business owners how do we wrap not only our business, like how do we wrap our business around our lives, around who we are, around making the whole picture work? And knowing that yes it can be scary to hire things out, but that sort of the sooner you can kind of wrap your brain around that it gives you that opportunity to make a bigger difference for people and to make more money. And you don't have to hire employees either right? 

We have clients who hire people and have teams, but we also have a lot of people who just hire contract workers, and that's like this entry point to being able to do that. So yeah, it's kind of annoying because like a lot of times people will be like “work smarter, not harder” you know and I feel like that's just such a thing people say but it's like what does that really mean? I don't think it's smarter, I think it's more aligned, you know and how to uncover what all those things are like getting that support is really smart support to get as soon as you can. Yeah.


Jessi Burg

And how to ask for help is such a vital business skill that I think is really hard in this mentality of the rugged individualist and something that Jenn Uhen, who I know has also been a guest on this podcast, says that she's not a self-made man. She's a community made woman. And that's one of my favorite things I've heard her say, and I think it's really true that we're not self-made, no one's self-made. Everybody has help from you know any area of even just somebody has helped clean your house, somebody has come over and brought you a meal when you're hungry, somebody has been your first client even though they don't know you, they took that chance on you and on your business and figuring all those pieces out, so everybody catches their breaks in different ways, and everybody is part of a community. 

So asking that community for help is I think a huge way to help scale your business and then also figuring out how to not be afraid of money. I think that's true for a lot of people who start businesses as they know that they want to start it so that they have more freedom, but they're really afraid to ask for the sale because they don't want to be rejected or they're really afraid to charge more money because they're afraid to be rejected, or they're afraid that their clients will say “no I don't want to pay that much for your service” or however those pieces work. I think really doing some hard thought on how much money do you need to make in order to run the kind of business that you want to run, and have enough leftover for the type of life you want to lead? And then use that visioning as your starting point. “How do you set up your operations to support that goal?” is a really important way to learn to think about it.



Yeah, yeah, kind of on the money piece of things… It's very easy to get your self-worth wrapped up in what you charge in your business when they literally have nothing to do with each other like we all have worth, we all are valuable as humans, and it has nothing to do with what we charge and how much money we ask people to give us right? And that's hard to separate. Yeah.


Jessi Burg

It's so hard and I think that's really important and it's really hard to get around some of the things we talked a little bit about demographics earlier. And one of the things that's true about me is my family's Mexican and so in a lot of ways I was yet another broke Mexican starting a landscaping company. So you kind of have to work through some of those stereotypes that build out on yourself and how do you work through those? I pass white very neatly, particularly early in the summer where I've lost a lot of my tan, so it was always kind of this odd thing where somehow I'm always like too brown to be white but too white to be brown. And and you have to work through all those whatever your weird demographic things are, everybody has weird demographic things. 

Knowing that you're not alone even in trying to figure out those different pieces and so it's okay to be a woman asking a man to pay you more money and that's a thing we have to work through. It's okay to be a person of color asking a white person to pay us more money -that's a thing you have to work through. So you have to integrate the ways that you think about how you exist in the world, and how those power structures exist in the world, and how you want your business to interact with them. Particularly as a founder and that might mean recognizing how those power structures play out in your workplace. 

One of the things we did in my landscaping company was in order to prevent, well there's a common toxic culture that happens at a lot of trades companies where you have a lot of men and very few women. And what happens is the woman shows up on site and they say “yep I'm ready to do some hard manual labor” and all the men on site go “yeah, we're going to give you the easiest job with the least amount of work because we don't think you're physically capable of doing this job”. And that's something every tradeswoman I know regardless, whether you're in roofing, whether you're in HVAC, whether you're in landscaping, we all run into the same issues. I never wanted to have that in my landscaping company, and so one of the ways that I prevented even creating that kind of culture or risking creating that culture is I always had a woman do the first round interview, and we certainly had male supervisors and we had female supervisors but if somebody was blowing off the woman doing the interview and they were ignoring the questions and they were talking over and they weren't being respectful in the interview process, I could be pretty sure that that person was not going to respect my female staff. 

And it was just a really easy way to build that into that inclusive work environment and start to subvert some of those traditional power dynamics that are very common in the trades. How that works in a different company might be setting up a different system, right? Maybe you do a second interview that has the team fit that a lot of people do. Maybe you do paid interviews right? Which is a thing I really love as a part of an interview process but really thinking about how do you build a culture that's inclusive? How do you build power dynamics in your company that aren't as set up along the traditional demographic lines so that you give people more power within your company to have opinions? How do you as a leader listen in a way that really works for the rest of your staff so you can bring in different pieces? 

Because if you have a company that does that, then it becomes a lot easier to ask for more money from your clients, to handle those types of issues when they crop up outside of the world, right? So I certainly in my landscaping company and in my current company have been told that as a woman I can't possibly know what I'm talking about… Okay sure, but I do, so have a nice day. You know.



Yeah, yeah.


Jessi Burg

But I was able to tell those people I didn't want their business because I had this other set of people over here who did want my business. So building out those places where you can succeed is really important.



Yeah, and I think that's really important and I think that can be really scary right? Like for people starting a business, I feel like so often I see where they feel like they have to wash over those things, they have to tamp that down, right? And it's like because they don't want to lose out on business and you're doing yourself a real disservice, not to mention the world, and like really kind of leaning into that can be a better way to find employees, clients, whatever it is who are a better fit for you and who you can make a bigger difference with. But I think that can be a really scary thing. 


Jessi Burg

Yeah, and I think how you go about it matters too. So one of the things I thought about a lot when I started Outgrow Your Garage is how did I want to structure this business? And I decided that I wanted to be a for profit company that had complete control over all of the programming and the way that I did I was going to be the solo owner, I wasn't going to take outside investment, I wanted to execute the vision that I had for my company, and be able to solve the problems I wanted to in a way that I wanted to solve them. 

I'm also working with a demographic that is very commonly left behind, is very commonly strapped for resources, both time and money, and often does not trust institutions that say they're here to help you. So that's a really hard thing to navigate and I would have access to more resources if I were a nonprofit because I would be able to go after grants, I would be able to go after different sources of funding, but I didn't want to do that because I hate this idea that help is charity and that's the only way to go about it. I think there are certainly, absolutely some really spectacular nonprofits out there that are doing amazing, amazing work and I also think they aren't capable of helping everybody because like any nonprofit, their resources are limited. 

So how do you find a way to meet those things and so Outgrow Your Garage can really get folded into other businesses in a way that works. We can become an operational resource for coaches who are really great at visioning but need help with helping their clients on the accountability side of their operations. Banks who are constantly talking to small business owners and going “I need two years of financial history to give you a loan” and you have a box of receipts. And that is not two years of financial history of your business. Now those banks can say Outgrow Your Garage has these pricing courses and these budgeting courses and these financial courses, you can run through those and you end with all of the information you need to have a bank loan, how to set that up, how to get all those pieces together, so we can start rolling into other pieces in a way that would be a lot harder if I had to answer to a board because I can fit into all the little cracks.



Yeah, yeah, yeah.


Jessi Burg

And so that's a really important piece to support what other organizations are doing, but that was a choice I had to make and a lot of people have gone “you know this would be easier if you made a different choice” like “okay sure, but I didn't, and I didn't on purpose. So, if you're not going to help me, have a nice day.”



I so appreciate all of that. I'm curious if you'd share with me a little bit more kind of thinking you know you were sharing a little bit of some of the struggles that you've had in your business based on identity. You talked clearly a lot about your gender identity within the trades world. What other impacts have you had on your business because of identities that you may hold? And again knowing that it's not the demographics it’s the individual right? But you know again, this is about because so many people don't get to hear the voices of those who share their identities right? So that's why I like to call that out and hear about that.


Jessi Burg

Yeah, and identity is so funny because we're always so comprised of so many of them right? Nobody's just 1 thing, I'm not just 1 thing, you're not just 1 thing, lots of people aren't just 1 thing, and there are a lot of us who are a lot of things right?



Yes, yeah.


Jessi Burg

So I am mixed race, I'm queer, I'm Neuro divergent, I grew up poor, I have all these different things that really play into how I move through the world and they all show up at different times. One of the things about being mixed for me that's really hard is, as we move towards this world where diversity, equity, inclusion is a common topic, we tend to completely forget that mixed race people exist at all and that's really hard too especially if you are a lighter skinned mixed race person right? So if you can pass white the BIPOC community is like “well you can pass so your life isn't as hard” and the white community is like “well you're still BIPOC so you're not included with us either” and you're like “awesome, now I don't get to fit anywhere”. 

That's a thing that I run up against a lot in working with the communities that I do work with and Good Business Colorado, who is an organization I absolutely adore and I'm involved with, did a series of inclusivity workshops a while back and they split it into BIPOC community and white, and I was like “Great. So where do I fit guys?” Culturally I'm white, my mom is white, and so I went in with the white group especially because I also pass white for a lot of the year. I went there but the experiences they were having where they had to alleviate this white guilt and kind of manage all these things, wasn't my experience. Because I've had the experience of being both the brownest person in the room and being the whitest person in the room and that just gets awkward.



Um, yeah.


Jessi Burg

Kind of across the board I used to get mistaken for the neighbor’s kids sometimes at family reunions because I look like my irish mom and the rest of my family looks exactly the same. They all have the same same face, and they're all Mexican, and so you know awkward stuff has happened in my life.


Jessi Burg

So I find it really interesting, but right now what comes up a lot is I live in a rural place and I interact with a lot of people on policy that happens in urban spaces. So one of the ways that I advocate a lot for right now is how do you balance the needs of rural areas and urban areas? Because more people live in urban areas but the infrastructure is lacking to a much greater degree for really anything you're talking about at all in a rural area. So like right now we talk a lot about how the world is moving digitally. Everything's digital now and digital literacy is a huge thing. And here where I live, we don't have internet everywhere, we don't have cell reception, and so our ability to meet those needs of a changing digital society is really hard because we straight up don't have the infrastructure. And if we don't have the infrastructure, we definitely can't do the learning. 

And so navigating all those different pieces so that's kind of where things come up for me a lot. Of the many things I am, which one is most pressing today and do I want to acknowledge that or not? Sometimes I will and sometimes I won't. And that's a choice I make a lot too is how out do I want to be? How vocal do I want to be about being neurodivergent? How do I want to disclose that I'm not as white as I look in a space? What are all those different pieces? Do I want to talk about the fact that I grew up poor and then have now started two successful businesses and running through that is like a great, beautiful American success story that everybody loves. 

But also like I got married at the beginning of when I started my landscaping company and my husband paid all our bills for a couple years while I got that up and running. So it wasn't like I did this by myself and I magically built this successful business and I don't know what that would have looked like if I hadn't had all of my living expenses paid by somebody else while I was getting that business up and running. So really thinking about which of those things is relevant at any given time. But I definitely think a lot of why I work with people who don't have any resources is because that is the thing a lot of us have in common if you’re not at the top of the power structure.



Yeah, yes, yes, yes, yes, and so much of what I just hear underlying that like again, it goes back to it isn't just about demographics, intersectionality exists everywhere, where do you hold privilege? Where do you have an oppressed identity? How does that impact? How is that relevant here and now? But ultimately if we're really working towards equity it's “yes, there is this macro identity context” right? Being a black person in America versus being a white person in America is not the same experience even remotely. So there's the macro part of it I guess but then there's also just the individual part of it and again, how do we work to humanize the way we do business, the way we run companies, the way we you know, really everything I mean got my background in education like how do we humanize all of the systems that we have and try to create equity and inclusivity and belonging for everybody?


Jessi Burg

And yeah, it's such a hard question and it shows up in all kinds of different ways right? I have Facebook groups where somebody posts about whatever sexism they encountered on the jobsite that day and a hundred women are all like “yep, that's happened to me too” and it's both depressing in that it's so common but also nice to have this community of people that says “yep I've been there, you're not alone.” And the same thing is true of the small business community or anywhere else you're talking about is saying “Yeah, it's not the same” and I think there's power in that acknowledgement. 

One of the things that is definitely true is to say I know black women who have had an objectively harder time moving through their business world than I have based entirely on the color of their skin right? Like that is true. And that can be true and I can also say you should hire this woman to do this thing because she's good at it, she's amazing and never ever bring up the fact that she is of color or is queer or is neurodivergent or whatever. So like really getting used to talking to people you can acknowledge and also promote the businesses that you think are great and make sure you make connections with people outside of your circle. 

I think a lot of it is just you if I didn't maintain really specific connections with the friends that I had made on the front range, I live in a county that's like 98% white, you know, so I'm not going to make new friends of color out here. So I'd have to really work hard on some of those pieces. And actually I don't even know, we're not really 98% white there's a lot of agricultural migrant farmworkers that move through this community. But they're very hidden and it's very segregated and so like those are all things that we have to work around and manage. 

But it starts with how do I promote the voices that I know? How do you promote the voices that can be promoted in easy ways? Find the easy wins and then as you build up these easy wins more things become easy wins. I think about how I have blue hair and a visible tattoo which are two things I could not have had when I first entered the professional workplace twenty years ago.



Yeah, yeah, so interesting. Okay, so with that I would love to move into a coaching conversation and if you still want to talk about what I think you want to talk about it also I think relates here. So what are you currently grappling with that we can dig in on?


Jessi Burg

Yeah, so Outgrow Your Garage is a growing company and one of the things that we're really working on right now is how do we split my brand of a tiny angry woman, who does things out of spite, from my company which is really focused on how do we create practical solutions for small business owners who are struggling? And that's a really interesting split, but is just starting to become kind of relevant because as the founder of a business we choose to be public figures to a certain extent, right? And my staff can hide behind the business and be like “oh yeah I worked for this company that does these things” but I founded a company that does these things and I founded it because I believe in it and that's what I want to do and I have all the vision and the guidance around how we're going to get there. 

So it is inherently tied to my brand but also I'm kind of working on separating it a little bit because I also want to continue regardless of at this point I've started 2 businesses, it's not outside of possibility that I become a third or I join a board somewhere or I do all these other things so thinking about what that split looks like of how do I operate as a person? and then how do I operate as a business owner? and what things go on what Linkedin some days? is the question. 



Yeah, so I love this question. I think it's a really great question and I mean my biggest wondering for you is… how is it different?


Jessi Burg

My business is detail oriented and extremely methodical and I am none of those things. So that's one of it, but also the business I think there's a different focus right? So the business is really focused specifically on making life easier on an operations level for service based businesses right? That's the focus. And as a person I'm really focused on how do we use business as a catalyst to advocate for and generate more voices who are able to be vocal, have the free time, have the ability to talk about the things that matter to their community so that while the businesses focus is operations and how do you get your business in order. My personal focus is how do we create more business owners who are able to generate change in the world? Much like I feel like I'm paraphrasing Kite & Darts mission statement on that one but it's true.



Hey I'm glad we're in this together. We need to be because we can't do it all and so we need all of us doing it but I'm going to argue that so to me this feels like there's an either or being put in this base where it can be a both and. Because I really feel like there's the values, the commitment to what you want to create in the world that you're saying is your personal thing. The business is just the vehicle for how you approach the problem based on your strengths and the strengths of your team right? So just like you said before I think your mission and our mission are very closely aligned. How you go about solving the problem and how I go about solving the problem are different but we're still going about solving the same problem. So even if your business, if Outgrow Your Garage is very much about the operational logistics, all of those things you're trying to support business owners with that, so that they can have more money, have more time, have more efficiency, higher, better, move forward their agenda right? like all of those things so to me, it's not separate. It's just about the vehicle for how you get there.


Jessi Burg

Yeah, and that is a fair point because one of the things I think about a lot and I think that a lot of us say as founders is, I'm not interested in being an Elon Musk or a Jeff Bezos, where we have all this money and we run these companies that everybody hates and they have this huge monopoly and they're terrible humans right? That's not why most of us go into business, like I don't know anybody who really wants to be like a billionaire who just walks all over people and is terrible right? That's not where most of us set out as a goal and their companies certainly reflect those values right? Their companies are terrible places to work because they have terrible humans as business owners. If anybody is surprised that I hold those opinions about Elon Musk and Jeff Bezos, sorry you must not have been listening to the rest of this podcast but there it is.



Right? They're probably not here I'm going to argue because they do have their own set of values and their own set of values is money above all, greed, power. You know what I mean? It's all for me, it's just a completely different set of values and none of those folks are listening to anything I have to say because they don't give a shit.


Jessi Burg

Right? And so I think that certainly some of it is fighting those niches and in that sense, I really like how you put that as “both and” because it is the idea of one of the things I'm very skilled at as a person is articulating the space between groups right? and being able to say to policymakers “here is how this policy will impact service based and gig economy workers and seasonal employees” I have questions specifically about that. I can have that conversation articulately with policymakers, but I can also say to the other people I know who work in this seasonal world “hey I have these questions about this bill. Here's how I understand it. What do you think?” Having those same pieces and being able to flow between those two spaces is a great skill of mine and Outgrow Your Garage is really designed to do that.

 A venture capitalist who I was speaking to a few weeks ago (who I will leave unnamed), said a little while ago “well, a lot of small businesses just don't present themselves well.” And I was like “you mean they're not white, college educated, dudes.” If you really want to help small businesses get more capital into their pockets, you have to forgive typos in business plans, like you just have to. But if I weren't able to code switch in that way between my different worlds as well as I can, he wouldn't have heard that. I wouldn't have been able to give such a specific example because I have to understand how both of those things work because I know business owners who don't speak English as their first language, and I know business owners that don't have college educations, and I know business owners who got their GED while in prison. 

So they just were out of the world for a while and have all these skills to learn because the amount the world has changed in 15 years has been dramatic to say the least and so none of those people are going to write a business plan that a venture capitalist is going to be really into because there's too big of a culture gap. So Outgrow Your Garage is really designed to fill in some of those logistics gaps and then I guess my personal brand is the yelling about it, pointing out that there's a problem.



Yeah, exactly.



Yeah, and here's what I'm gonna say is that we label that as source commitments over here right? So it's like values right? It's “what are you deeply committed to creating in this world?” And the more you talk about those things, the more the right people will be attracted to Outgrow Your Garage as clients, and the bigger help you're going to be to those people because they're the ones who may identify in these different ways and they need this kind of support. So you being out there and being very vocal about these things as your personal brand, I'm always like still bring in the business to that, constantly bring that in just like this conversation today. 

And the other thing that I'd call out though because I feel like there's another piece that I hear in there which is “I may outgrow Outgrow Your Garage and I may leave it to go do something else or just change whatever” and you're building this organization that can continue without you and so there could be new people who come in. So to me, we're like back to the power conversation. How are you giving power to the other people in Outgrow Your Garage to also bring in their own voice. To bring in their own commitments and values and ability to be vocal and that can be a hard thing to do right? but that it's not just like Outgrow Your Garage is this because and I think this happens all the time where companies will be like “here are our values” but the people running the company don't actually share those values. They may talk about them, but the way they behave is different. 

So if you have the alignment between your own person and what you're doing in your business and the people that you're collaborating with, everybody can go out and have their own personal brand, but it still makes sense that you're coming together to further Outgrow Your Garage because you care about the same things right? and I speak partly about this because of my experience with Kite and Dart right? Nate started this company and I came over here and I, being a multiracial woman, felt like I had to try to be mini me with me and that didn't work at all. We're so different right? We care about the same things but we're so different and it took me a while to find my voice and step into my power to you know, I wouldn't have this podcast without being able to do that right? and I'm doing this, Nate's doing his own thing but it all makes sense because we're still working towards the same vision of a different world. 

So to me part of it is like if you're expecting that your personal brand has to be separate from the Outgrow Your Garage brand that's also saying that the people you're partnering with inside of Outgrow Your Garage, they don't get their own personal brand or you know what I mean? That also has to be divorced and I just don't think that that's real. Right? Yeah, does that make sense?


Jessi Burg

Venn diagrams, not circles. It does make sense and I like it and it is one of those things like figuring out how all those pieces blend together is a really fun thought experiment in how those pieces work. Cause I do really like the people puzzle of how do you fit in all the places and how do you find people who are good at the things you're not, how do you find people who want to learn, how do you find people who are in different spaces, and one of the things I really like about how Outgrow Your Garage operates is we take a stance of curiosity right? Always always be curious. What are the problems that we're blind to, what are the problems that we know about, how do we solve these in ways that actually work for people? That tends to be something of how I operate in my personal life also.



Yeah, yeah, and I think that that's part of what's so important right? So many people start a business because it's just like “I need to make money I'm going to do this thing” right? And there's so many different reasons. But like when we can be super clear on what are we committed to creating in the world then that's where we can find our best collaborators because if you're all committed to creating something similar then you just know that piece you have in common and then it is a matter of how do you use my strengths and your strengths and their strengths and the other person's strengths to come together to lift up this thing. 

I mean this is literally foundational work we do with all of our clients right? Which is uncovering “What is it that you really want to create, what are you committed to in this world, and what are you great at and love to do?” and the overlap of those is how you can be the biggest contribution in the world. Right? And then who are the other folks who overlap with what you're committed to creating and how are you leveraging what they're great at versus trying to stick people into boxes and into needing to fit a certain thing. I hear this so often where people will talk about how things don't make sense, and I think it's because of this idea, you brought this up earlier. We contain multitudes, we're all multi hyphenates and why do we have to diminish one thing in order to hold space in another? We can contain all of those things, we don't have to let go of part of who we are to show up in a different space.


Jessi Burg

That is a really lovely way to put that. I like it.



Yeah, but I don't think that that's historically what's happened right? I feel historically as a teacher… No, there's no room for personal life and it's like well that's crazy like my personal life is always with me like I am who I am.


Jessi Burg

Yeah, and I think that's the thing that I firmly believe has been missing from a lot of the business conversation is the term “work life balance” has really gained a lot of popularity in the last several years but realistically your life is always going to be more important than the work that you do for everybody all the time. Whether you own a company, whether you're an employee, whether you're a contractor, whether you're a solopreneur or whatever. 

So the more we can really pull those into how we operate businesses, the better your business is going to be and the more resilient it's going to be, the less turnover you're going to have, the less drama you're going to have in your business. And you're going to be able to do things more efficiently, more quickly and have a better environment. We've all had toxic work environments and everybody hates them because they're terrible.



Yeah, yeah, well and to that point I think I talked about this with someone last week again was like this whole idea of work life balance like it is really saying “okay, you can have your personal life, and you can have your work life, and they are separate, and they don't cross over. When you're at work, you just need to do work.” There's no need for work life balance, there's just need for a life balance. There's a need for intentional life. I don't think about “I need exercise life balance” or I need “sleep life balance.” Work is a facet of life, we need to figure out all of the pieces together holistically, it’s not 2 separate things. It makes me crazy. 


Jessi Burg

Yeah, you're not wrong and like you do, we had a conversation right before this podcast started where I said my dog is feeling really needy today and she might start barking in the middle of this. But she wants to be right next to me, and that is just a part of my life and luckily for me, she's been sleeping behind me this whole time. That's just how it goes because that's what happens when you work from home.



Yeah, totally. So hopefully that helps and gives you maybe some perspective, I think really the overarching message is that it's not an “either or” like how can you embrace the “both and” and see that they really do fit together? It doesn't have to be nice and neat and pretty with a bow on it that this is my personal brand and this is my business brand.


Jessi Burg

And the business does get to espouse all the things that I believe in anyway, because I'm instilling them into, I'm teaching everybody on my staff that you should tell your boss that they're wrong if they are.



Yeah, as you should.


Jessi Burg

But if you're actually wrong, and that's the thing I expect them to carry into the world like that's a real part of working for me is I'm wrong all the time. So if you're not going to call me out on it, we're going to have a problem.



Yeah, right, right? And it's a great vehicle for creating this world that we want to live in because what's happening in business is the same thing as what's happening in our homes, is the same thing that's happening in schools, and happening in government, and it's all the same thing. So let's just embody it completely. And it doesn't mean everybody has to see it the same way as you, but it's more about the value of it and then how do we embody that and how do we still get to be our own individuals? Yeah, anyway. Two quick last questions for you. These are my rapid fire questions. Would you share what you think what entrepreneurial activism means to you?


Jessi Burg

In my case, it is starting companies out of spite that I think things should be better and they're not. I don't know how to be an entrepreneur without also being an activist and I was an activist for a long time before I was an entrepreneur. And so one of my favorite things about the world I live in now is I get to do both of those things. People always told me I'd be less angry and calmer as I got older and that is not true. I just get more targeted in how I make those changes.



Yeah, I love that. I hate that Paternalism. I got so much of that when I was in college like “isn't she cute? She’ll outgrow that someday.” 


Jessi Burg

Yeah I have not, I have not outgrown that, is what I haven't done.



Hallelujah. The last thing Jessi, would you please share how people can get in touch with you if they want to learn more or connect with you?


Jessi Burg

Yeah, if you're looking for information on Outrow Your Garage specifically, the easiest way to do that is to go to and you can find us there. There's lots of information on that. If you want to find me specifically, Linkedin is the best way to find me.



Fabulous. We'll have the links in the show notes. Jessi, thank you so much for your commitment to really you know taking these things on, creating inclusive workspaces, and supporting others in being able to do that for themselves and really have successful businesses and I just feel like both sides of what you're doing in your business and how you're doing business are really contributing to making the world a better space. So thank you for that. Thank you for sharing your story and for being here today.


Jessi Burg

Yeah, thanks for having me. I had an excellent time.