Size Matters: How Fast to Grow your Business

Last night I had the pleasure of joining Jennifer Key from Chief and Heather Cox from Mighty Little Web Shop at the DC Web Women Speaker Series on growing your business. We all came at it from a different perspective, highlighting our unique experiences. I spoke about my experience at different startups and how their growth decisions shaped their conclusions as well as my decisions. Jennifer talked about her personal journey grounded in intention, culture and risk.  Heather spoke about the flows and ebbs of business, which ultimately led her to focus on a very specific niche.


I consider myself an entrepreneur, but Digital Ambit is really my first business. I guess I’ve been closer to a entrepreneur groupie, or maybe just entrepreneurial employee. I’ve had several opportunities to come into businesses early on and help them grow. Some took VC funding, and other self-funded. Some suffered their demise by way of the exuberant spending of the dotcom bubble. While others sold for a hefty profit or pivoted and continued on as a smaller, boutique offering.

Jennifer opened her talk by mentioning that she can’t tell others how to grow their businesses as she doesn’t know them or their businesses. However, she can outline the drivers of her growth, which contributed to the growth of the businesses she’s been involved with. There are 3 critical components she comes back to when evaluating opportunities: intention, culture and risk. Every day, Jennifer starts her day by setting her intention. While these days these are focused on gratitude and kindness, they do fluctuate. By setting your intention, you ground your decisions. Business culture is what drives employees and founders to do what they do every day. Businesses need to decide what their culture will be, and as they grow will need to figure out how to sustain that culture. Sometimes the culture isn’t sustainable, and that’s ok. Although a loss or change in culture may shift employees away. Lastly, business (or personal) growth is about risk. Jennifer herself is risk adverse, but she surrounds herself with mentors and friends who encourage her to take calculated risks.

Heather wants to be a rockstar when she grows up, singing her songs and playing the guitar. In the meantime, she’s focused her business on a niche market and learning what she needs to in order to grow her business. For a long time, Heather didn’t have to market her business. The leads just flowed in. She started this business to engage her dream of building websites and developing marketing strategy for her customers. She opted for packaged pricing so she’d never have to write another proposal. She also participated in some extensive marketing and accelerator programs to learn what she needed to know. Heather is quick to admit she sticks to the basics of understanding her numbers, but has clear size, revenue and margin goals she focuses on every day.

Overall, i saw some clear themes in our stories.

  1. Optimism – Although I wouldn’t consider myself very optimistic, I do have confidence that I can learn and conquer anything I want. “They aren’t problems, they’re possibilities” and “there are no obstacles, but rather opportunities” were a few of the catch phrases of the evening. They definitely highlight the optimistic nature of being an entrepreneur. Some days are scary, but you need to fundamentally believe you can reach your goals.
  2. Mentorship -We all talked about people we worked with that gave us their time and expertise when you need it. Jennifer reminded us to that we need to value our mentors time and make sure to set an agenda so you can work on what you need. There are formal and non-formal mentoring programs, but any opportunity for networking is an opportunity to find one.
  3. Culture – Heather has really molded her business around the things she likes to do, removing or outsourcing the things she doesn’t. That will make for a very deliberate culture. Chief is known for community engagement and built that into their office space. They have a space dedicated for entertaining and host numerous meetup and other groups on a regular basis. I’m building this business with my husband to drive the culture and lifestyle we want. The choices we make in our business will all come back to why we started it and what we want.
  4. Know your numbers – It’s imperative to understand what’s going on in your business. Without that how do you know if or when you can hire? How do know what’s success? or slow down? You don’t need to be the accountant, but you do need to keep an eye on your critical metrics. Identify a few critical ones that tie to your goals and watch them closely.