Jessi Burg

Founder/CEO at Outgrow Your Garage, PBC


Education: St. Lawrence University - Naropa University
Delta, CO, USA


Jessi graduated college in 2007, during the Great Recession. After unsuccessfully looking for work in her hometown of Philadelphia, she finally found a job teaching ecology to middle schoolers at a camp in Connecticut. The pay wasn’t great, but room and board was included. For the next ten years, she juggled low wage seasonal jobs in education and summer camps, and at one point worked 7 part time jobs to make ends meet. By 2017, something had to give. While she loved working outside and taking jobs that felt meaningful, she also wanted a savings account. The solution? Start a landscaping company. She joined organizations such as Good Business Colorado and discovered that being an owner amplified her voice. She talked about the challenges facing seasonal and gig workers and policymakers listened. Her 2nd company, Outgrow Your Garage, builds on that advocacy work by connecting community resources to entrepreneurs, with a focus on supporting sustainable economies in rural and urban areas.


My absolute favorite thing in life to do is finding the right angle from which to tackle a complex program. I often say that I can’t change the world, but I’m doing my best in my little corner. In practice, this ranges from helping an entrepreneur plan for a new revenue stream to talking to policy makers about specific bureaucratic barriers to entry for small business owners. As a woman who has spent most her life in male-dominated fields, I can’t fix the sexism and misogyny many of us face. But I can work with hiring managers to create a more equitable process. (The first starting point is making sure the hiring manager and the position supervisor agree on what the role is.)

When I’m not focusing on small business growth, I also love working with communities to create opportunities for youth. As a rural resident, one of our biggest challenges is ensuring there are job opportunities for recent graduates, both high school and college. One of my favorite current projects is working with career services departments to find new ways to connect students with job opportunities and potential employers, especially students who want to move to or stay in rural areas.

I am willing to travel

More than 100 miles

When it comes to payments

Everything is negotiable


small businesses small business ownership women entrepreneurship women in small business being the only woman in the room woman owned business woman and innovation woman ceo woman entrepreneur skilled trades business development business strategy organizational development people first people first leadership online learning online learning methodologies leading remote distributed teams staff retention seasonal businesses neurodiversity learning and development virtual learning accessibility female founders small business growth solopreneurship small business operations

Best Story

This year, my oldest niece will be a senior in high school. Everyone is asking her what she’ll do in the fall, and like so many other kids her age, she has no idea. It’s kind of a weird idea, that someone should know what they want at 18, when they’ve often never lived outside of their family home or explored professions that don’t exist in their family or friend’s network. In her case, it’s especially tough because she lives in a town with one key industry, and not a lot of other opportunity. Her goal is more “how do I learn what I like in life?” as opposed to “what do I want to do with my career?”

So when she came to visit over the summer, we took her to the local university for her first college tour. I live in rural Colorado, so our local university is 45 minutes away and has 10,000 students. It’s the biggest school within a 4 hour radius, and a much different environment than the satellite state school campus in her hometown. This school is a medium school with small classes, where most people live on campus or nearby, and it has a thriving connection to the local community. She had no idea such a thing even existed.

A lot of people disparage “kids these days” for a lot of reasons. I think those people have never spent time with a kid who’s trying to find their place in the world. Watching my niece as she envisioned an entirely new possible future for herself was an awe inspiring experience. She lit up in a way I’ve never seen her do before - suddenly, the possibility of leaving a place that felt stifling was a real option. It became a tangible reality, not a distant, unachievable pipe dream.

As an adult, it was a good reminder for me too - dreaming big isn’t enough. You have to find those first baby steps that take your idea from a dream to a walkable path - and a community that supports you along the way.

Origin Story

I started my journey as an entrepreneur after years of toxic work environments. I kept changing jobs, working within education, summer camps, seasonal trades, non-profits etc, and nothing ever stuck. Either I liked the job, but wasn’t paid enough to live, or the work environment was awful, or both the pay and the work were awful. I knew there had to be a way to stay passionate about my career, while valuing employees and paying a livable wage.
The answer ended up being to start my own company and be my own boss. I started a landscaping business, and almost immediately discovered a plethora of resources to help me start up and almost nothing to help me grow. But grow I did - from a company of just me in year one to a 12 person staff with near zero staff turnover by year 4.

I found that being a business owner amplified my voice, and gave me a platform to advocate for the lack of business development in the trades and service industry. Eventually, this led me to create Outgrow Your Garage, a business learning community focused on trades and home services. Outgrow Your Garage provides the tools and resources I wish I had when starting out, plus everything I’ve learned along the way.

It’s a running joke that I started it accidentally 6 months into the pandemic, when a friend of a friend asked for advice on how to start a landscaping company. It was winter, my off-season, and my spouse and I were hiding out in rural New Mexico at an AirBnB for the month. I had time, so I said yes and we set up a weekly coaching meeting for the next 8 weeks to get her started. That was how I discovered I don’t like coaching.

However, I loved building the curricula, thinking about what mattered, and how to build your business for growth from the beginning. My previous background teaching ecology to middle schools turned out to be extremely helpful - teaching busy entrepreneurs how to create systems in their business wasn’t that different from working with distracted teenagers. At the end of 2021, I made the leap from landscaping to full time focus on teaching business development, and Outgrow Your Garage was born.

Through our on-the-go course work, we provide guidance and problem solving for operations such as hiring your first employee, automating client communication, setting pricing in a service based business, managing a schedule when you have more locations than staff, and more. Each course is tailored to different learning styles, and ensures that we help you understand how to apply the course content to your business while setting realistic goals for the future. It’s everything I needed when I grew my first company, with the added bonus of building a community of entrepreneurs who support each other across industries.