Starting a business is hard because it’s a fight with yourself, an internal battle – gaining the courage to get started, etc. Scaling a business is different – the challenges you face are mostly external to yourself. Each challenge has a million mini-challenges. We wanted to create a space for conversations and stories around growth and scaling. Below, you’ll find stories and insights from successful entrepreneurs across a variety of industries and markets.

Angel Nicolas

Scaling my real estate business was anything but an overnight success. It was a journey built on relentless effort, learning from failures, and continuously adapting to new challenges. When I first started, I laid the foundation through cold calling, knocking on doors, and leveraging every connection I had. It wasn’t glamorous work, but I knew that to grow, I needed to put in the hours and master the basics. One of the early lessons I learned was the importance of becoming a marketing specialist. I devoted a lot of time to understanding how to handle objections, ask the right questions at the right time, and for the right reasons. I recognized that real estate is a numbers game—the more calls I made, the better I got, and naturally, my closing rate started to increase. Read more>>

Rachel Bauman

In August 2018, we moved to Duluth to be closer to family and launched Purejoy House Cleaning, initially offering residential services. At the start, I was the only cleaner, and my husband Alex stepped in to help with tasks like marketing, accounting, and sales. Things changed dramatically when I became pregnant with our first son in 2020. I could no longer manage the volume of cleanings alone, and that’s when we decided it was time to grow the business. Hiring my first employee, Grace, was a major milestone, but it also marked the beginning of a steep learning curve. The experience of scaling up was a phase of constant trial and error. At first, we didn’t have any formal systems in place. How do we onboard and train employees? What should our expectations be for scheduling, gas compensation, or incentive structures? It was a balancing act of experimenting with new approaches while adapting to feedback from both employees and clients. Read more>>

Natassa Wachsman

When my husband Bryan and I started Rubber Ducky Isopods, we knew it was going to be a challenge. We were both leaving career paths and were venturing off into something new to both of us. Bryan’s background was in cannabis and mine was in science; so we took our knowledge and put it into our company. It was a huge risk, but we were ready for it. As any entrepreneur knows, the early days can be hard. Balancing work and family life was a huge challenge. It’s hard to ‘turn off’ when you are building something you believe in. We always joke that we work 24/7 so we don’t have to work a 9-to-5—and there’s a lot of truth to that! Early mornings, late nights and long weekends became the norm, but we keep going because it is all worth it to us. Read more>>

Pierce Kafka

Our growth has been bootstrapped, consistent and referral focused. If we do right by our clients, growth is inevitable. Our pursuit is in scaling the quality of our team, the strength of our relationships with the media, and the growth of our client connections. Only then, after building the proper foundation and defining a clear mission, does growth occur. To quote ‘Field of Dreams’: “If you build it, they will come.” Read more>>

Grace Ramirez

Scaling has been very challenging, especially as a Latina woman. Access to capital, choosing the right business partner, understanding a business model, and having a business plan were all things I wasn’t familiar with. I come from a family of artists and a grandfather in the military. My grandmother made clothes and bathing suits for a living, but it was a small, home-based operation. It took me a long time to understand how to scale. However, I was able to scale La Latina Cocina because I had a strong concept, brand, and a clear vision of what it needed to be. I also had extensive experience working with food at scale. Read more>>

Nichole Okeke

You know how people look at a successful AirBNB management business and think it just popped up overnight? Trust me, it’s way more like a wild rollercoaster ride than a fairy tale! When we kicked things off, we had just a handful of properties and a lot of enthusiasm. Our days were filled with hustling to make our listings shine and figuring out what guests really wanted. Spoiler alert: it wasn’t just about having cute pillows! The middle part of our journey? Oh boy, that’s where the real fun (and chaos) began. As we started to grow, we ran into some serious bumps in the road—think crazy market swings and juggling multiple properties like a circus performer! Each choice felt like a big deal, and we quickly learned that keeping everyone in the loop—guests, property owners, and our team—was a game changer. Communication became our secret sauce, helping us build trust and keep everyone happy. Read more>>

Rachel Burger

I decided to open my own Luxury Interior Design firm, Studio 1950, in 2024. When I started building my interior design brand, I thought a lot about who I was, what I didn’t enjoy about my previously jobs, and how I can implement those ideas into my brand. This is ultimately how I came up with the idea of building a “silver dollar” interior design business. I knew I didn’t want to be the interior designer for everyone, so I built my business to reflect that. I began by specifying my ideal clientele, projects, and style. By starting here, I was able to create a direct reflection of that on my social media platforms. I implemented verbiage like “luxury”, “custom construction and renovations” and “business professionals” into my captions. Implementing verbiage like this allows potential clients to know if I am the right Interior Design Firm for them. Read more>>

Jocelyn Grim

I originally started my dance fitness business with the intent to do a plethora of in-person events and classes but I realized the inconsistencies of teaching dance classes in person. There were a lot of conflicts with people’s schedules due to having to take care of kids, family matters or just having a busy schedule. I decided to transition to an online model specifically on YouTube with the hopes of being able to reach a couple hundred people. That quickly became a couple thousand per video. The pivot to the online world was important because we live in a digital age everyone is on their phone. I wanted to bring fitness to the living room, so no matter if you had a busy day or if you’re a stay-at-home mom looking for a quick way to debrief from errands, you would have online videos right at the tip of your hands for free. The consistency alone has driven “Fit and Fab Crew” to over 8,000 subscribers in just 6 months. So constancy is important but my heart for wanting to help women get fit and stay in shape is even bigger and that’s where the passion and consistency is derived from. Read more>>