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Ep. 204 – Josh Little founded four tech companies. With two successful exits and third pending, he’s currently trying to save the world from “death by meetings.”

Josh Little Headshot

Josh Little is the founder of four tech companies–Maestro, Bloomfire, Qzzr, and Volley–that have collectively been used by hundreds of millions of people. With two successful exits and third pending, he’s currently on a mission to save the working world from death-by-meetings with his fourth creation, Volley.


Most passionate about

  • I am trying to save the world from “death by meetings,” as we all have gone remote with the recent pandemic and realized that we still need to talk to move work forward.
  • We are aiming to fill the gap between Slack and Zoom. Most people would say, “Well, I don’t see a gap there. I’m either Slacking my team or I’m Zooming with my team back to back all day.”
  • There’s this whole spectrum in between that Volley is aiming to solve. With Volley, you share asynchronous video messages. Imagine video texting. If you could text someone with a video, that’s kind of what Volley is like.
  • Volley allows teams to move work forward faster by replacing their meetings with asynchronous video conversations. The ultimate goal is to have productive conversations that don’t interrupt each other’s productivity because meetings are quite interrupted.

Josh’s career and story

  • I started as a teacher. I was a preschool teacher, a social studies teacher. I actually was four years into a music education degree. The only reason I wanted to be a teacher was to be a music teacher, but I did realize that the same skills that made me a good teacher also made me good at sales.
  • I left teaching to go into sales. I went to three Fortune 500 companies and did really well at each of them. I’d usually become the number one rep in the division the first year I was there. They would invite me to be the sales trainer and show everyone what I was doing.
  • I left Stryker, which was my last corporate job, and started my first company, which was Maestro.
  • From Maestro, we built Bloomfire. Then, after Bloomfire, I built QZZr. After kind of a long break and pondering what I wanted to build, the next idea, Volley, came.

Best advice for entrepreneurs

  • Be remarkable because the definition of the word “remarkable” is “worthy of remark.”
  • To truly be remarkable is to have people talk about the way that you engage with customers, the way that you show up in a conversation.
  • I aim for every interaction with a customer to be in some way remarkable, where they walk away from that conversation and say, “Wow, he really cared,” or “He really understood my problem,” or “I love how he was vulnerable there at that moment,” or “That was really funny what he did.”

The biggest, most critical failure with customers

  • With customers, my biggest failure has been withholding truth or withholding reality from a customer because you want to make customers happy and you don’t want to initiate conflict.

Biggest success with customers

  • I believe that I’m doing the best work of my life right now. I’ve had great success.
  • With two of my companies, I’ve had successful exits. I really think what we’re doing for teams and communication right now with Volley is extremely important work.
  • The reason I say that what we’re doing is a success—and this is very recent feedback we’ve been receiving from users—is that Volley has helped increase team connectedness and brought back the fun and the spontaneity that we once had as a team but that we then lost when we went remote. I think that’s really powerful.

Josh’s recommendation of a tool

  • Volley: That’s a tool that I’m using right now for reaching out to my customers. We’re using our product as our support tool.
  • LinkedIn and Zoom: LinkedIn is a great way to connect, but then, when you want to have a deeper, more meaningful conversation, text is just a very thin medium. So, you need to move to either Volley or Zoom.

Josh’s one key success factor

  • I think it’s changing. It used to be “Do what you say you’re going to do.” That’s kind of a personal mantra. Having no gap between your words and your actions is really important.
  • Small changes each day really do add up over time.


Josh’s Mountain

Since we believe that the best way for entrepreneurs to get fast, big, and sustainable success is by leading your (new) market category, and the entire entrepreneurial journey reminds me of mountaineering, I want to ask you: Is there a mountain you dream of climbing or a mountain you have already climbed?

  • I’m climbing several mountains simultaneously in my life right now and will continue to do so. The interesting thing about peaks is that what you thought was the peak when you started climbing the mountain often isn’t actually the peak because when you get there, as you said, you realize, “Oh no, the peak’s over there and it’s much higher than where I am right now.”
  • We need to keep climbing. For other mountains that I’ve climbed, like learning to code and learning to program, I spent time doing that and realized that I could climb this mountain. It is quite a journey, but I also realize that the peak moves every day. It moves somewhere else. So, even if you achieve what you think is the peak, you can’t stop climbing.
  • You also need to think about, if you’re starting this journey, is it something that you really want to continue for the rest of your life? Like learning to be a software programmer? Because some mountain peaks do stay fixed, while others move.
Metaphorical Mountain

Metaphorical Mountain


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