The Mindset You Need to Start and Scale an Entrepreneurial Career

I didn’t know it then, but my entrepreneurial career began when I was eight years old.

My family had some blueberry bushes on our property in Connecticut, and my brother and I decided to harvest the fruit and sell it for $1.25 per pint at our homemade roadside stand. After picking our inventory, though, I saw my brother’s makeshift stand and small paper sign, and I immediately knew they weren’t going to cut it.

So we got creative.

We transformed a big, old piece of wood into a fresh, dynamic advertisement, and I ran up and down the busy street, jumping and flailing the sign around to catch our high-speed customers.

It wasn’t the $60ish dollars we made that day that piqued my passion for entrepreneurial work. It was the commitment to the hustle and to learning new ways to market our product. It was the creativity we needed to stop cars flying by at 45 miles an hour. Most importantly, it was the connections I strengthened that day with my brother and our streetside customers. 

It’s these qualities that would later become the bedrock values for Carbon6, an ecommerce organization I founded to help entrepreneurs thrive at every stage of their selling journey. And it’s these qualities that I believe form the foundation for starting and scaling an entrepreneurial career.

Failure as a Means of Redirection

The road from selling blueberries streetside to founding a thriving, growing business poised to change the ecommerce landscape wasn’t paved with victory alone, though.

Throughout the first few chapters of my professional life, I held around 55 jobs — with the longest stint only lasting about three and a half weeks. Working in restaurants or doing manual labor, as well as pursuing a degree in psychology, wasn’t fulfilling, and I couldn’t quite get my feet underneath me.

I wanted to play music. I wanted to be creative. I wanted freedom.

What I quickly realized is that working for someone else just didn’t work for me. What helped me come to this realization? Landing a job as a door-to-door coupon salesperson, of all things.

Selling coupon booklets for $20, making $9 commission a pop in the tough Boston winters to the even tougher Bostonian customers was no easy feat. But it quickly showed me how rewarding working for yourself could be. After I saved up my first $2,000 from coupon sales, I fully tapped into my entrepreneurial spirit, realizing that by putting my newfound professional ambition and perseverance toward entrepreneurial work, I could do something great, make money, and help others.

Selling coupons lit a spark in me, and we quickly transformed from a business selling coupons door-to-door to a company representing the largest telecom and energy companies throughout Europe and North America. I was training people on how to run their own direct marketing companies in countries throughout the world. Today, that translates to hundreds of people running their own businesses with thousands of sales reps. With my partners, I used this step as a vehicle to raise several billion dollars for charities through face-to-face fundraising. Working for myself was great, but teaching others to pursue their passions was even more rewarding.

When I entered into the ecommerce space after hearing about it from several colleagues, I felt the same freedom and passion I did when playing guitar or helping first-time entrepreneurs succeed. I knew almost immediately that online selling was the future of commerce, so I followed my interests and built a set of tools to help sellers scale their revenue, optimize their listings, and manage their inventory — among many other things.

The lessons I learned selling blueberries and coupon booklets — as well as failing at dozens of other jobs — have stayed with me throughout my career, helping me build both my company and myself.

Taking the Reins

Embracing my entrepreneurial spirit meant tapping into a mindset for success. It meant immersing myself in a community of founders, learning and growing along the way. It meant giving as much as taking, and listening as much as talking.

Here are four steps you can take to develop the entrepreneurial mindset you need to start, scale, and succeed in your business.

1. Educate Yourself

Despite the skills and knowledge you’ve likely gained on your journey to becoming an entrepreneur, one thing will always be clear: You can’t know everything. 

That’s why it’s so important to ask critical questions to better understand your industry or space. 

• What’s the current state of the space? 
• How is it poised to evolve in the future? 
• What factors will drive that evolution? 
• What’s the best way for you to become an integral part of the space?

Talk to the experts within the space that are at the forefront of growth, regardless of whether they’re mentors, competitors, or both. Keeping up with the competition can be equally as valuable as building relationships with possible funders or advisors. With an abundance mindset — rather than a scarcity mindset — learning from competitors can help everyone involved grow and innovate.

There are two main reasons why education is a great starting point for entrepreneurs: It’s good for business, and it’s good for people.

Without knowing what the space looks like, you won’t know how to create the tool or craft the service that will drive change within it. Similarly, you can only grow your business if you build partnerships, listen to criticism, hire the right talent, and honor your employees. 

2. Champion Successful Teams

The single most rewarding thing I’ve been able to do in my entrepreneurial career is give others the control over their lives that they otherwise didn’t know they had.

The key to that reward? Accepting that people are the backbone of any organization.

As of August 2022, Carbon6 has completed 14 acquisitions. Twelve of the founders of those 14 organizations are still with the Carbon6 team. By joining forces with these leaders, rather than pushing them out the door, we’ve honored the skills and expertise they bring to the table. We’ve made partnerships — both big and small — that will continue to drive our company’s success onward and upward.

As you embark on your entrepreneurial journey, develop your team as much as you develop yourself. When you create a true community of leaders and employees, everyone sees the business as their business. They care, so they rally around the vision and work together to build something bigger.

Allowing others to help you build your company doesn’t mean giving any part of it away. It means solidifying the foundation of your business and adding to the power that fuels it.

3. Care About Getting It Right — Not Being Right

Being a CEO requires being adept at interpersonal interaction. After all, you hired experts to provide their expertise — now you have to listen to it.

To set your employees up for success, you have to listen to the feedback and expertise they provide. They don’t just sell the tools, but they also use them in the trenches of their business every day. That means that they have critical, invaluable insight into what’s working, what can be improved, and where the business should go next.

Opening up clear lines of communication can help you not only learn from your people, but also build community in the process. It can enable you to integrate smoothly into a space that existed before you, and it can help you change that space for the better.

When you hired your employees, you made them a promise that the business would thrive and evolve, and that they would be key players in that evolution. Listening to them, valuing their thoughts, and acting on their ideas helps you deliver on that promise.

One caveat: Don’t let listening slow you down. Your people want to be heard, but they also want to be part of your business’ forward progress. Keep your ears open and your feet on the ground.

4. Think Big

Listening to your people, your mentors, and your competition has another added benefit: It keeps the space as large as possible.

At Carbon6, we take the “big tent approach” by continuing to expand at a fast but steady clip, bringing new experts in along the way. We’ve added significant value to the ecommerce space, we’ve opened a training academy for new sellers, and we’ve expanded into various international markets.

What made this growth possible? Thinking big, and constantly leveling up.

If you continue to think bigger and bigger, you’ll never even see — or reach — the horizon. The opportunity for growth is only as big as your imagination. With the big tent approach, it’s seemingly endless. 

Regularly invite others into this big thinking exercise. Tap into your network of employees and colleagues to engage their ideas and compound the growth of your space.

When you make room for everyone, everyone wins.  When you think big, everything is possible.