Growing and scaling a business is hard and we wanted to hear from business owners who have successfully scaled a business. Below, you’ll find our conversations on scaling with some very talented and insightful folks.

Naysha Clark

I scaled up by staying committed to growth, leveraging strategic relationships, and consistently reinvesting in myself and my business. When I first started in real estate, I was balancing a full-time job while working part-time in the industry. My relentless drive and faith pushed me to take that leap of faith, and once I did, I made sure I never looked back. Scaling up required discipline, consistency, and a willingness to step outside my comfort zone. Read more>>

Jennifer Hoffman

What an inspiring topic this is that a lot of people don’t talk about these days. The work that goes into building a business especially in the beginning stages and all the nitty gritty behind the scenes is often disguised and I think it is important to share our stories with others. I worked in the corporate world for 10 years before branching off on my own. I worked for some incredible event planning & hotel/resort companies where I learned so much that helped push me to eventually branch off on my own. It was not an easy or safe choice as a steady paycheck and benefits is very attractive. However, I always knew I wanted to build and create things my own way in order to be ultimately fulfilled and satisfied in my professional journey. I will say… it wasn’t easy at first and still there are sacrifices I make to achieve my goals and be successful. Read more>>

Nathan Miller

Since Rentec Direct’s founding almost two decades ago, we’ve experienced substantial growth. In the beginning, revenue wasn’t a priority or concern of mine—I started Rentec Direct as a side project and a way to give back to the landlord community I was a part of. For the first two years, the platform was free and we generated no revenue, even though nearly 500 landlords and property managers were using our software. My measure of success in those early days was how many people I could help. Read more>>

Andrea Faulkner Williams

Over the past 10 years, we have been so lucky to bring people onto our team who have helped us grow Tubby Todd. To encourage growth, the best thing you can offer your team members is a clear understanding of what the goals for the brand are, where you are headed, and how they can contribute to scaling up the business. Three years into running Tubby Todd, we decided to bring on a minority investment with operating experience to aid with scaling up the brand and eventually, we decided to sell a majority share to a Private Equity partner that we still work closely with today.  Read more>>

Jason Collin

I was able to scale up over time by first getting a foundation client that had repeat work for me that set a baseline through the first two main years of the success of my business. In those two years I was very visible in person in the business community and joined the chamber of commerce so as many people knew I was a photographer and could be referred to for work. Each new client I got I provided more than I said I would, in a way then exceeding the client’s expectations. Then I added the client to my weekly photo newsletter that I did not sell in, but just featured my work and thanked clients for their business. In this way I was able to begin to establish repeat clients, a key for a sustainable photography business, as finding a whole new set of clients every single month is a tall task. Read more>>

Elaine Stageberg

People love to talk about overnight success, but in my experience, true success is built brick by brick, through years of intentional effort, strategic risk-taking, and a relentless focus on delivering value. Black Swan Real Estate is no exception. Today, we manage a portfolio of over 1,350 doors and $330 million in assets under management, but the journey from our first rental property to a vertically integrated, institutional-grade real estate firm was anything but instant. Read more>>

Caeli Richter

Three years ago, I left a corporate job that I loved to pour all my time and energy into launching my photography business full-time. I am naturally cautious, far from a risk-taker, and I tend to overanalyze everything. But I knew that building a business from the ground up would take time, and I prepared myself for that reality. Instead of focusing on overnight success, I focused on what was within my control and what I could do that would ultimately set myself up for success. Read more>>

Kymberly Robinson

The story of building my legal practice has been both organic and strategic. In law school and upon graduation, I was dedicated to litigation. This was primarily my focus for 15 years in New York and Florida.

However, in 2021 that changed. That’s when my childhood friend came to me with a new venture: she wanted to start a health coaching practice and asked me to be her attorney. I helped her form her limited liability company, advising her on various business structures, and in the course of that, I realized something—I enjoyed this. Shortly after, a social media post led to another referral, and before I knew it, my practice shifted. Word of mouth was powerful and fueled my practice. Read more>>