The show’s guest in this episode is Josh Little. He is the founder of four tech companies–Maestro, Bloomfire, Quizzer, and Volley–that have collectively been used by hundreds of millions of people and featured in TechCrunch, Mashable, Entrepreneur, Inc, and Forbes. With two successful exits and a third anticipated, he’s currently on a mission to help remote team communication suck less with his fourth creation, Volley–a video messaging app.  Tune in, and be transformed!

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Helping Remote Communication Suck Less with Josh Little

Hey, everybody, it’s super great to be here with you live today. I’m really excited about our show today. And I just kind of wanted to tell you, I’m in my childhood bedroom, because I have, I have migrated to New Mexico until May. And I’m super excited to be here. And one of my son’s is swimming and enrolling in school here because of the COVID shutdowns in Ontario. And so I’m a little off kilter. But I had this conversation with my husband, when we were trying to decide whether or not I could go away for five months. I said, are we going to be okay? And he said, Melanie, we are fine. And it’s, it’s had me just his attitude about it. Like, he was so solid in his sort of assertion that we’re okay, it’s okay to go do what our kids need. And it has me thinking about like, When should we just allow ourselves to be okay as leaders? When do we need to settle in and not be stirring up trouble and looking for problems and trying to process the next thing? When is the most powerful thing we can do as we lead our own lives? Just to be okay to be okay that you don’t have your your things to be okay. That you don’t get everything that you want to be okay that the food comes out different than how you ordered it. So my challenge to you this week is how can you just be more okay with what is today.

I am so excited to welcome Josh Little and he’s the founder of 4 tech companies, Maestro, Bloomfire, Quizzer, and Volley. And they’ve been collectively used by hundreds of millions of people and featured in text TechCrunch, Mashable, entrepreneur, Inc, and Forbes. And he’s had two successful exits, and a third is anticipated. And he’s currently on a mission to help remote team communication suck less with his fourth creation. Volley. I am so excited to get to have this conversation. I love talking to serial entrepreneurs.

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Welcome to the show, Josh

Well, thank you. It’s my pleasure. And I’m trying to just take your advice being okay with with what is. That’s, that’s sage advice. So I’ll run with that.

Yeah, what what has your interest about that? What’s what’s interesting, too, I mean, you’re, you know, we’re talking about how to help remote communication suck less. So, you know, we’re there already. And yeah, what what caught your attention in the idea of just being okay with what is?

Well, in the stage of growth that we are at volley, we’re a young company, just trying to gain traction and find product market fit. Sometimes you do need to be patient, and you kind of need to wait for growth to happen and wait for that moment. And if you synthesize things, or try to try too hard, you can, you can ignore very important and delicate data that point you in the right direction. So it just feels like the right advice for me today is the the leader of this company and, and flying by the gauges that we’re looking at.

That’s really nice. And I think startups or maybe have a little more of that, like you, you know, in a startup, you don’t have all of the structures that you can lean on. So sometimes it’s okay to wait to create those structures sometimes. You know, sometimes it’s worth the the rush and the heartache to do things quickly. But sometimes it’s okay to let things be and to enjoy them. Enjoy where you are, because each step has strengths and weaknesses, I think in a company.

Absolutely. And it’s hard to smartly separate those two. And when are you moving too, too fast and too hastily? And when are you moving too slow and need to step it up?

Yeah. And I’m curious like about that leadership piece. You leading a company and you’ve you’ve led successful companies before. What are you experimenting with in your own leadership right now? What are you thinking about in 2022?

Yeah, so we’ve, my co founder, and I’ve kind of coined this phrase called continuous leadership. And it’s really what’s happening is a by product of the product that we’re building volley, which is a it’s a video messaging app that allows you to have asynchronous video conversation. So what does that even mean? Well, we take turns just like any other conversation, except we record corridor turn with video you and I’ve taken a few turns already in this conversation and you know synchronicity, being in the same time that’s in place is good for some things, but not not everything. And there’s a lot of communication that can happen asynchronously. This is why we have chat tools and email and text and, and all of those things. So volley very much marries the richness of talking face to face with the flexibility of texting. And that’s the idea of the video messaging app. And so that what that enables as a leader is me to continuously sync up check in unblock inspire, in a way that is outside of time or place, I can say what I need to say move on with my day, I can answer that question, ask to check in with one of our engineers, you know, do my stand up and all, you know, simultaneously help three of our users in the first 12 minutes of my day, because I’m in these flexible conversations that I can just pop in, show up face to face and then pop out of and the the people on the other side of that conversation can pick up that that volley in you know, whenever it’s convenient for them, they can listen to me on to x, and they can have total recall the conversation and, and go back. And when they asked me a question back, I can take whatever, you know, a few seconds or a few minutes, whatever it takes for me to feel like I’ve composed a thoughtful answer and come back with with hopefully something that’s much better than if we were even sitting face to face. So that’s beauty and that what that’s enabled in me as a leader is this. What you know, what we’re feeling is this, this idea of continuous leadership. And we’ve seen that with many of our, whether users in the teams that are using it, or the coaches who are using it is like just in time coaching where you know, you know, someone who’s had an executive coach for a number of years. Suzanne’s great, but Thursday at 3:30. is sometimes I have content sometimes I don’t sometimes are ready to talk sometimes I’m not. And really I need her Tuesday at seven and Monday at three, rather than Thursday at 3:30. Right. So that’s what volleys enabling in that conversation as well as many of our users which is exciting kind of a new way to lead, which is on demand.

Yeah, it’s a really interesting concept. And I’ve used a different sort of text, like a voice program for a while with my clients. And it’s interesting to think of video and what that offers. And what do you find? Who do you find is like, totally gung-ho about volley? And who do you think is reluctant?

Well, it’s, uh, you know, talking about experiments, we thought who would be totally gung-ho, at least on paper would be remote teams, because I mean, communication is at an all time low. Loneliness is at an all time high. Connection, collaboration is just strained. When you’re remote, it’s harder to move things forward, it’s harder to communicate. So we thought, oh, this would be the perfect tool. And while we’ve had 1000s of teams adopt volley, and that’s really exciting. And there’s a bunch of teams that are tearing it up, the reproducibility was just hard for us to find there. And at the same time, we saw all of these coaches and YouTube creators and consultants who are doing client work or coaching or have courses or building communities, pick a value is like a flexible face to face way to engage their audience, or to have a little VIP super fans club or to have this discussion around their course, or to do their one on one coaching in an on demand way. And so when we looked at teams, our deliberate strategy, you know, our experiment, like why we, why we built volume, what our, you know, cents was, versus all of these other use cases, which are just impossible to ignore. They’re, they’re just exploding, they’re tearing the product up, they’re finding reasons to build new features or needing, you know, threaded replies because the space is just too busy. We’re like, okay, I guess we’re building it for them. Okay, let’s, let’s pay more attention to them. And this, you know, has happened just in the last couple of months for us, which is exciting. I mean, we’re just looking for a starving crowd and a great killer use case to take this product and run with it. We’re just trying to build a better way for the world to communicate. And we’re happy for whoever is happy with that solution. And so we’re excited to be working with the solopreneurs and the coaches and the craters of the world.

I’m curious whether or not as you use this tool, because I’m guessing you’re one of the biggest users in you know, of this tool. Do you find it speeds up where you’re just on on all the time, because you’re communicating so much more frequently with so many more people?

Yeah, it just gets to the point like meetings in synchronicity has so much bad behavior surrounding it us getting together I call it they just soak up whatever time to give them. So, you know, this is Parkinson’s Law. Like, if you give a meeting an hour, magically, it’ll take an hour. The magically what you needed to talk about was one hour long or a half an hour long. And really the the reason we’re getting together is we just need to talk and that doesn’t change when we’re remote that, you know, we still need to talk to move work forward. And, you know, getting in a room or on a zoom is the only way we’ve been able to historically do it. But now we have a new way, which is to volley. And what we find is a lot of things that would have been meetings, really were just a couple of volleys, like I just needed to talk through my problem, I needed to verbalize that out loud in a way that I’m not going to write a book of an email, but I can say it in like two or three minutes, I can explain the problem, I needed to show you something, you needed to think about it, you need to give me feedback, I need to come back maybe one or two times, and then it’s done. And so what would have been 30 minutes to 60 minutes is really just three or four volleys. And that happened in like five or six minutes. And because I can listen to you on to x, you can listen to me on to x, and we can we can catch up with a conversation when we have time, which is outside of our deep work, we’re not only more productive, we’re not only sped up. But I can also take time to think before I respond to you which educational research shows anytime we can take three seconds to think about a question once it’s asked, we’re gonna come up with a fundamentally better response. So volley kind of speeds up both sides, as well as hopefully enables more thoughtful responses. And so yeah, that’s kind of what we’re seeing is it just kind of erases this magic time box that we tend to put around things.

And I’m a huge fan of the 15 minute meeting for exactly that reason. Like, if you need another 15 minutes schedule, another 15 minutes, but probably if you schedule 15, you might actually accomplish it in 15. Right. So I’m curious, just, I want to just shift gears a little bit. You’ve been the you founded a bunch of companies, and you’ve exited some. And I’d love to know kind of when you think Oh, I I want to start a company. What’s that dream cycle? Like? What like, what are you dreaming up as you at the beginning in the big really beginning stages of a company? How does that how does that happen for you?

Well, I’ll go back to my first company Maestro. The dream was for me, it wasn’t really about the type of company or problem, it was more I knew I was being called to be an entrepreneur, I knew that was inevitable. My wife knew it. I was going to spontaneously combust into an entrepreneur one day. And so, this is like a five year process of like finding the right vehicle, like what, what could potentially, you know, keep our family fed, while enabling us to, you know, create a business something, no one in my family or, in my circles, really had ever done anything like that. So there was a lot of risk it felt so in the beginning, it was just kind of more practical, like trying to mitigate risk, what could potentially provide a living, something that I could do that we could own, which could be a vehicle to create wealth and create opportunities for others and those things. So that that was the dream in the beginning is what could possibly do that. And so the dream has evolved for me as an entrepreneur because it’s doable. Okay, yeah, we’ve established we can start companies. Okay. And then with bloom fire my second company, okay, we’ve established that Josh can build both service and product companies and tech companies and, okay, check. Now what kind of tech companies matter. And I’ve shifted to thinking more about the problem, and more about what change do I want to create in the world and the opportunity to build volley came Honestly, after over a dozen experiments over a couple of years of finding the right vehicle. And it was really just kind of, you know, a combination of the pandemic, my love for asynchronous video communication and having thought about this problem for over a decade, that kind of came together is like in the technology was finally right to create a new and a better way to communicate face to face but flexibly. And so, you know, just those sorts of ideas and opportunities come along every so often. And just had to take the opportunity. But for me still, I view myself as an entrepreneur, much like a painter views themselves. I care really, I really care less about what exactly I’m painting, whether this is a street scene, or a landscape or a portrait, and more about the craft of painting more about the craft of entrepreneurship and building this beautiful thing and how to do that efficiently with, you know, this capital faster than we’ve done before with in helping serve more people in the process. And what does that even look like? So those are the things that really excited me. And in, you know, commies are the dream, you know, but back to your question,

How do you think about legacy for yourself?

Um, you know, that’s not something I think about very often I don’t, I don’t know why not that it’s not good. I found that my, my calling in life, or My why is to create beautiful things. And hopefully, I leave a legacy of beautiful things. And for me, a beautiful thing can be a piece of furniture, it can be a jar of pickles, it can be musical performance. I, I, I have a talent as a creator, as a musician, as an artist, to create beautiful things. And that’s what I feel compelled or called to do in the world. And so companies just happen to be the most challenging, creative endeavor that anyone can embark on building. A company is building something out of nothing that can create life and livelihood and great financial outcomes and, you know, touch the lives of millions of people. That’s a pretty beautiful thing. And that’s, that’s a really challenging creative endeavor. So that’s why I keep coming back to this even though I think I’m done. I thought I thought I was done a couple of times now as an entrepreneur, but then now the the need the need to create just keeps, keeps coming back. So maybe that’s my legacy to create beautiful things, but I really don’t think about it in terms of legacy. Should I? Is that something I should think about more?

I mean, I think I think that you’ve got like a true north, I love the beautiful things part. I think it’s really lovely. And, and it also gives you the freedom that I want to see and legacy, which is it’s not like, you want to make one thing. It’s not like it’s just pickles, it’s pickles, it’s art, it’s beauty. It’s like, so there’s so many possibilities in that as a sort of direction. So I, I think it’s I think you’re on track. I mean, I You seem happy. I mean, I don’t know.

I’m super happy. I don’t have to do this, but I choose to do this. And yeah, it’s it’s challenging every time. Every time I put on the CEO hat and the founder hat. I feel the weight. And I think, Oh, why did I do this? It’s so hard. It’s heavy, to be a leader. Right? So yeah, but it is also rewarding.

Um, where can people find you, Josh? And where can you find volley?

I’m hard not to find me if you find volley. Because every user is added to a conversation called Hello volley, which is a direct connection to the team. And I show up there from time to time. So just download volley and you know, invite some others, and you’ll find me for sure if you’re looking for me. But if you’re looking for a better way to communicate, you know, there’s there’s the bonus of that. Or you can find me on LinkedIn, I’m pretty active there as well.

That’s great. And it has been so fun to talk to you about all that you’re up to about how you’re thinking about communication. Thank you so much for being here. It’s been really fun to have you.

Well, thank you. I’m honored to be asked on the show and and glad to be here. Thank you.

Yeah, great, thanks.

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Well, that was really fun. And I love you know, this idea of volley as on demand communication. It fits in line with all of the lean Toyota kata stuff around just in time. And I love all of that. I think it’s really, you know, it’s really iterative. So you can have more iteration of exactly what you need to remove bottlenecks and to do it right at the last second, or, you know, to repeat the questions often enough to remove your bottlenecks one after the other, which is like speeding up productivity. So I love that. I want to really invite you to download a copy of my book at digital book dot experimental leader.com and I also want to tell you that offers an opportunity to buy a workbook where you can actually chart your own progress with that book I, I really wrote that book, it took me seven years to write it. And I really like when people get a chance to take their own learning, and to think about it, and to actually have a place to put that learning. And to keep that learning. There’s additional questions there. I want it to be, I always dreamed of having that book be like, dog eared and tired and the pages marked and highlighted. And the feedback I often get when people finish it is, oh, my gosh, I need to go back and read it again. It’s a pretty rich book and has lots of sort of helpful tips to help you lead a team. And so I’d love to hear from you. If you buy the book and you have feedback. I have so few feedback look about. I have so few feedback loops around how people experience the book live, and I’d love to hear that. Well. It’s been great being here with you today. I challenge you to think about how you change the way you communicate with your team in any way you can think of and go experiment!

Important Links: 

• Volley – Asynch video messaging
• Josh Little – LinkedIn

Josh Little

Josh Little is the founder of four tech companies–Maestro, Bloomfire, Quizzer, and Volley–that have collectively been used by hundreds of millions of people and featured in TechCrunch, Mashable, Entrepreneur, Inc, and Forbes.

With two successful exits and a third anticipated, he’s currently on a mission to help remote team communication suck less with his fourth creation, Volley–a video messaging app.

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