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Josh Little started his career as a teacher, and evolved into the founder of four tech companies: Brinemaster, Volley, Qzzr, and Bloomfire, collected and used by hundreds of millions of people.

His work has been featured in TechCrunch, Mashable, Entrepreneur Inc., and Forbes. He's currently on a mission to save the working world from “death by meetings.”

In his hometown, Josh saw three options:

• Work at the large state prison in the town
• Work at the power company where his father worked
• Become a teacher 

By the time he started student teaching he knew it wasn't his thing. He saw that in his father - he would never leave his work for any reason - but recognized that passion wasn’t in his life. He taught for about a year and, although he loved the art and the craft of teaching, he just didn't love it as a career.

He was very successful in sales - the same skills that made him a good teacher made him good at sales, and that started his career in the corporate world. Two or three days a week, Josh worked sales at night as his side hustle. During the day, he was a full-time teacher. He learned very quickly that he could make more in those two or three days than he could make his entire week at school. 

More than that, Josh discovered that sales was fun, and he could accomplish things faster and get rewarded for them. After selling over the phone, working for internet providers, he fell into healthcare-oriented products. 

In his words, it turns out if you can motivate 11th graders to not burn down a school (a real event that happened a year before Josh started teaching at the same school), you can also motivate people to buy something. 

What Comes First When Choosing a Business

When choosing a business, there are many factors involved. In Josh’s career, his first real business started when he was 11.

It was a profitable lawn mowing business, a clear sign of an entrepreneur at an early age. His mom was an entrepreneur, though she didn't know it. She just did odd jobs: cleaned houses, painted walls, wallpapered. He thinks it’s funny that he grew up in and around that, but didn't understand what that was or how to do that.

Then he went off to college, got a degree, and thought that was the end-all, be-all. Until he read Rich Dad, Poor Dad by Robert Kiyosaki, a book that has changed the direction and perspective of a lot of people.

It was like a revelation: You can own a business, and if you want to, you can be wealthy.

From there, it took five years of thinking, talking and having lots of lunches with coworkers and friends about choosing a business they could possibly build, and planning and validating before he officially stepped out and got started. 

In the end, he knew he had made other companies millions of dollars selling their “stupid products”, and if he could sell their “stupid products”, he knew he could sell his own stupid products. 

During his time as a salesman, Josh spent a lot of time traveling, and filled journals with product ideas on years of flights, from water flavoring packets to car air fresheners.

He knew he needed to choose an idea that wouldn't require an insane amount of capital, so he could become profitable as soon as possible.

Josh realized very quickly that companies continued to seek him out for training their teams, and he found he was keeping the circus together by himself. It had basically already become a full-time job just to coordinate all of it, and he thought that there should be a company that does the job for them.

Since Josh couldn’t seem to find that company, he left and created it, which is now Maestro. Nearly every other training manager in medical device and pharma felt the same way. They were able to build a network of the “who's who” of clients in the field pretty quickly, and today Maestro builds content for Netflix, Microsoft and a range of other cool companies.

Since leaving his job cold turkey to start his own company, Josh has learned all of the ins and outs that were so difficult for him at first. He learned and grew with Maestro until 2010.

The Next Problem to Solve

Twitter was on the rise, and Josh decided to make his next move. They took the profitability of Maestro and invested that in a software platform called Bloomfire, and it worked. 

The world was just getting used to Twitter, and then they launched their idea: why not be social at work? Now in 2021, of course, we're sharing videos and messages with our coworkers and chatting, but back then it was a wild idea. Luckily, there were many forward thinking companies that adopted it. Eighteen months later, the company was acquired, and was recently acquired again by a private equity firm.

It turned out that their predictions were right, and popular, but just really, really early.

Bloomfire’s goal is to capture tribal knowledge - to connect like-minded thinkers and professionals to collaborate and create. As quickly as the idea was built, loved, and bought, Josh was ready with his next idea.

Evolving the Answer

At this point, Josh had been essentially working on the same problem for over a decade: how to get the right information, to the right people, at the right time, at work?

In essence, both Maestro and Bloomfire were addressing this, but he knew there was more, especially as working at home and remote team management grew in popularity.

This new idea took the richness of Zoom and the flexibility of text, and combined them.

Volley was born.

Their goal is to enable deeper work for remote teams. The word volley is used in tennis, in volleyball, and even ping pong, and it simply means to send something over to the other side.

The “comeback part” is called a rally, and they thought about naming the company “rally” for that reason, but rally didn't seem to connect as well as volley. A volley is a back and forth motion that leads to victory.

Especially coming from a complex, technical medical-sales background, trying to get across a simple message about a complex product requires distillation. 

Communication is our culture: without communication, we have nothing. The way we communicate is the way we relate, the way that we trust, the way we work as a team. Volley hopes to be a big part of that. 

Relationships aren’t new, but now we’re trying to establish them in a remote environment, and that means that every interaction counts. Communication matters most for them.

For this reason they are choosing to use Volley, because you can speak seven times faster than you can type, and time is of the essence.

Startups, side hustles, and small e-commerce companies are using it, as well as coaches, influencers, and individuals who want to connect with their audience. 

Josh hasn’t stopped yet - in fact, he’s still taking these same principles and growing them into better, more useful tools.

To try out Volley, you can download the app for iPhone, Android, Mac and PC and invite your team. While Josh’s LinkedIn is included in the intro, you can also find him through his family’s traditional pickle business.

For more content like this, check out The Jeff Bullas Show.