4 Entrepreneurs Who Braved Stepping Into Uncharted Territory

4 Entrepreneurs Who Braved Stepping Into Uncharted Territory

For those with a true entrepreneurial spirit and mindset, barriers are something to leap over, not stop you dead in your tracks. That applies even to those for whom the barrier is creating a business in and industry and market for which they have no experience or knowledge. For this type of entrepreneur, knowing and demonstrating smart hustle is an essential. And while the challenges are vast, it can be done and the four entrepreneurs in this story are proof that by marrying determination with smart hustle, all barriers can be overcome.

Imagine starting a business and not only dealing with the traditional challenges a start-up faces, but adding an extensive learning curve by entering an entirely new industry and marketplace. Those successful in doing so understand that there are some key strategies that can help them through the process. Here are a few of those:

  1. Know Your Strengths. Like most smart entrepreneurs, knowing your strengths is a key to making the path to success a little less bumpy. Because most business skills transcend across many industries, knowing your strengths and how to apply them can be a huge benefit in breaking into a new industry.
  2. Use Naivety To Your Advantage. A great advantage to those breaking into a new industry is what most would feel would be the greatest weakness: naivety. But in fact, coming into a new industry without a preconceived notion of the ‘rules and regulations’ allows you to leverage a fresh perspective, which could lead to creating much needed solutions that are outside the ‘norm’.
  3. Find and Use All Available Resources.  When starting in a new industry, it’s going to be essential that you learn as much as you can, so find all the available resources you can. Take classes or become certified in the industry. Attend trade shows to become familiar with competitors and lateral products. Find a mentor. Those determined to be successful going down this path find whatever resources they can…and they take advantage by utilizing them to the fullest.
jessic mah


Jessica Mah, CEO and co-Founder of inDinero, started her company with no cash and no previous experience. Through adversity and failure she was still able to turn her start up into a successful venture. Jessica opens up in a Q&A session to discuss some of the challenges, obstacles, and successes she's faced in building up inDinero.

Smart Hustle: What does inDinero actually do? What problems are you solving?

Jessica: At first we weren't really solving many problems, we were trying to help businesses visualize their finances online so they could make better business decisions. Now we do software and service. We pair you up with an accountant and take care of the software as well.

Smart Hustle: Do you have a tax background or an accounting background?

Jessica: No. I have a computer science background, and I hadn't done any accounting before starting this company. To combat this I studied to get my IRS license so now I can legally represent in tax court. When I decided to do this pivot to customized solutions, that was a big question, "what makes you qualified"? That sounds so obvious, so I took the test to gain credibility which then allowed me to hire better accountants because I actually look better, and I have the C.S. background which lets me say I know what to look for.

iDropped Charles HibbleCharles Hibble, Founder

“My decade’s worth of experience in real estate has prepared me to be the entrepreneur and businessman I am today. The everyday business challenges I faced in real estate – like marketing, accounting and selling –  required me to excel in multiple areas of business. The skills and knowledge I acquired through that experience have transitioned with me to the tech world and have helped in the development of iDropped.”



Mizzen+Main Kevin Lavelle Pic 2.jpg2Kevin Lavalle, Founder
Mizzen + Main

“The idea for Mizzen+Main hit me more than ten years ago - bringing performance fabrics to traditional menswear. I had seen what happened with performance polos: initially dismissed but then universally adopted; why couldn't the same thing happen to the rest of menswear? For years I told myself ‘if it was such a good idea, someone else would be doing it by now’ and eventually decided I had to give it a shot. All game changing ideas started out skeptically viewed, why couldn't I be the one to do it? Though of course I knew I would face limitations coming into the industry as an outsider - and challenging the status quo of the industry at that - I firmly believe that initial naiveté  has been one of my biggest advantages. I’m not limited by preconceived notions that stopped everyone else before me. Building a new product category has been tremendously exciting and of course incredibly challenging. I’m thrilled with our progress so far and can’t wait to see what’s next”



Suitey - David WalkerDavid Walker, Co-Founder

"The best thing my co-founder and I did when starting Suitey was to become real estate agents ourselves.  Diving headfirst into the industry we wanted to disrupt was the key to our success and the knowledge we gained is still pivotal in running the company to this day."


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