Venture Anyway Builder Podcast
Venture Anyway Builder Podcast
4X Tech Founder on Enjoying the Journey with Josh Little
In this episode, I speak with Josh Little - serial entrepreneur. He started off as a high school teacher then had a successful career in corporate sales before he started his first company in 2007.
He is the founder of four tech companies — Maestro, an e-training company; Bloomfire, a closed social platform for companies; Qzzr, the world's simplest online quiz platform; and finally, the application where I’m hosting this interview, Volley, which he co-founded with Joe Wilson, tailored to be the one-stop-shop for businesses to have efficient and productive communications. His work has been featured in sites such as Forbes, Mashable, Tech Crunch, and Entrepreneur. Enjoy the episode!
In today's interview, I get to talk to Josh Little, who is the co founder of Volley with his partner, Joe Wilson. And I love I absolutely love this interview. And one of the things that I'm most impressed with with Josh is his level of competence. I am a part of several different groups with him. And I, I've been impressed multiple times about the just the, the, how broad his skill set is, whether it's playing the guitar, or all the reading he's done in health and fitness or his multiple successes and startups. It's really cool. And I felt just blessed to be able to have this conversation with him. And I love his level of candor. Especially I think one of my favorite parts of the interview is when he talks about his purpose and his why. And near the very end, he actually just drops, you know, some amazing truth bombs. And it really just kind of blew me away his perspective, and the kind of why he does what he does. So I'm really excited for you all to hear this interview with Josh Little. So without further ado, let's roll the interview.
VA Intro:Welcome to the venture anyway, builder podcast. Insights from the trenches by those who are busy building. When I finally embraced what I was really good at, it kind of felt like an adventure. Yeah, I really would have done a lot differently.
Dale Majors:Hello, hello, Dale Majors here and welcome to the Venture Anyway Builder Podcast. Today, we will be talking to Josh Little. And I say today lightly because this interview may happen over several days, Josh and I are using the app that he and his co founder Joe, Volley developed together. And I'm sure they have a great team behind him. But I have loved Volley. It's a - an app like Marco Polo, I call it the Marco Polo for business. And it's a really cool way to collaborate with other people. It's a great step between email and in person meetings and whatever. But I'm sure that we'll be getting into that. So anyways, without further ado, I would like to introduce you to Josh Little. And, Josh, if you could tell us a little bit about yourself. Give us a quick intro, and then we will dig in to the interview.
Josh Little:Hey, Dale, thanks for having me. I love this idea of podcasts that I can actually think about my response before I give it hopefully I'll put a better version of myself forward today. Well, I started my career as a teacher, high school social studies, quickly realized that wasn't my thing. And moved on into the corporate world trying to figure out what on earth could someone do with the skill set for the world. And it turns out sales, had a successful sales career three Fortune 500 companies that went into sales, training and marketing and eventually gave me the concept for starting my first company, I always had this entrepreneurial itch, and I started my first company in 2007. And since I've started 4 tech companies, that have been used by hundreds of millions people, Maestro, Bloomfire, Qzzr. And now my latest creation, Volley, which is, as you said, a better way to communicate, we built it for team collaboration, it makes a lot of sense that teams need a better way to communicate that increases connection and community and therefore video messaging is that vehicle however, what we're seeing right now, is other use cases take off even faster than team collaboration. Those are coaching community, and education. So we're really excited about that. We really just wanted to give the world a better way to communicate. And now we're seeing how the world wants to use it. And it's unfolding right before I so it's an exciting adventure.
Dale Majors:Josh, I absolutely love that. That's amazing. And this is awesome. Because I am recording a podcast while walking my dog at night. I love Volley. And I can consume it while walking and everything. It's just amazing. So you have quite an amazing story and kind of pedigree in startups. And I checked out some of your past companies. And you know, especially recently, as I've seen, just what you're doing on Volley, and how often I'm using Volley, and how often the people that I'm talking to about Volley are recommending Volley. It's pretty amazing. And I'm kind of jealous that and missing out that I haven't gotten in on any of the investment rounds, so you'll have to keep me posted. But the question, so you've, you've started several software companies, and I would love to know, maybe some of the key learnings that you've had, from your experience starting software companies, amazing, you know, going from teaching to sales and sales, training and marketing. But yeah, what's the maybe what are the core takeaways you've learned in the last few years doing what you do?
Josh Little:Yeah, well, I guess the beauty is we can have a conversation that spans over months, you know, because it was like a month ago, when we hit the last volley, and that's okay. Right. It's whatever the conversation needs. So to thank you, and to answer your questions, it's, it's hard to, like give broadly applicable advice, but I to and there's thousands of things, that's the thing, but let me, let me try to distill a few things that I usually share, like when I speaking classes, in colleges or whatever. So one of those things would be, don't be afraid to move the boat. And this is a fishing analogy. Because oftentimes, trying different bait in the same spot is less productive than just moving the boat to where the fish are biting or finding that starving crowd. And you could call that a pivot, but it's like a pivot with purpose. And it's not just like, you know, running running at the same audience. We found this with Qzzr, when we built a quiz tool for teachers and trainers, and then publishers started embedding quizzes in their website, we're like, oh, that will do that. You know, and, and we're finding it with Volley. We build Volley for teams. And now we've got coaches and YouTube creators are running with it. I've asked her and we're like, okay, what are you doing with it? Okay, cool. Well, we'll see that. So don't be afraid to move the boat. Because you're probably going to be more successful. And I know, it feels like a lot of work. Because you got to pull up the anchor, and you got to start the engine, you got to get everyone to put the chips away and whatever. But the reality is, takes like five minutes, and you're moving. And it feels scary. Because what if there are no fish in that spot? So that's, that's the first one I would say. Another one I often refer to is just relentlessly pursue the most impactful thing. Which is so so so, so hard to do, even if you're trying to do it, because you just kind of have to dig and you kind of have to really look at your to do list and what's what's, what are your OKRs? And, and does that even matter tomorrow, if you Yeah, you can do your OKRs or whatever your goals are. But in a startup, they just constantly change and you constantly have to be willing to relentlessly pursue the most impactful thing. So my, one of my favorite questions to ask myself is, what would insert the name of your favorite entrepreneur? Do? So let's use Richard Branson. What would Richard Branson do? If he were CEO of Volley? Look at your to do list. What were you going to do today? Would Richard Branson do those things? Why or why not? And the answers to those questions probably reveal something like are you thinking big enough? Are you doing the right things? Is this really going to make impact? Are you doing this just because you said you would. Those are all valuable questions that help you continue to relentlessly pursue the most impactful thing. We're guilty of it here at Volley even though I'm trying to do that, you know, we kind of get this core set, okay, we're going to build these things. But then we kind of discover more important things. And then more important things will should we upset what we're currently doing. And we told our users that we're going to build threading or whatnot. So those are, those are two learnings that seemed to pay dividends over time. So I'll turn it back to you.
Dale Majors:Josh, I love it. That's awesome. Okay, so in follow up to that, I love that idea of not being afraid to move it to move the boat. And it's interesting, as you were talking through that I'm thinking okay, Adventure Anyway. How can I do that differently. So anyways, that's really thought provoking. Thank you for that don't have to keep thinking about it. And then relentlessly pursuing the most important thing, I love that. And I've also had this idea of, or have found value in, in thinking about different, you know, how different people would act in my shoes. So that's really cool to hear you talk about that. And, and a good reminder for me that I struggle with that a lot. Am I doing the most important thing? Or sometimes maybe looking back, I think, oh, you know, I probably could have spent my time better. And a lot of it a lot of those answers, I think are that, man, I'm just not thinking big enough. Right? So that's really cool. A question for that or a question in to follow up is how, what kind of cadence to operate on do you say, today, what am I going to do the most important thing is that is it a daily cadence? Is it a weekly cadence? Monthly quarterly? I know that and I think we all are built differently. So we may you know, that may be different for all of us. But I'd love to get your just for you personally. When do you go back and ask those questions? Do you create enough clarity each week to do that? Or every few days? Or is it? Is it less constrained by time in that way? So we'd love to hear that. And then for the for the next question. You've you've built several businesses. And you know, I guess most have been in tech. But what is surprisingly difficult about building Volley? Maybe you had this idea a few years ago, and now that you're in it, what has been surprisingly, more hard than you thought it would be?
Josh Little:Well, good question. Volley is my first product lead growth company. All three of my previous companies were either marketing or sales, lead growth, and really, out of the gate where price products like, you know, monetized so we're playing a different game with Volley. It's, it's one that is more honest. Because you can't just like pump steroids into an app and and have it catch traction. There's there's true retention numbers and activation numbers that count when you're talking about network products like Volley. So that has been a whole learning opportunity in itself, which has been fun, not so much a challenge, I guess, but just a challenge to, like, catch up to speed with with what's going on. And what makes a product lead growth network product, like Volley take off and work. And so that's, that's been a lot of fun. But I would say the hard part of that is waiting for growth. If, you know, I'm pretty used to being able to push the push the growth button, like, here we go. Okay, we got it. And admittedly, I've pushed that growth button too early in past ventures, like, we had semblance of product market fit, but not true mock product market fit, we kind of ignored the churn, and there were just enough users coming in to, you know, each month to you know, give us the vanity metrics that made us look good. So, so we're trying to be very honest about true retention. And you know, making sure that people don't just want to take the medicine, but the medicine actually cures the disease, which is hard. It's really hard, especially when we're talking about communication app, like, who wants another app letter, not another communication app, there's a lot of friction. So in order to overcome that friction, the product has to be mind blowingly good. And even if it is, people don't believe it. And so it's, it's just running through all the cycles to kind of perfect the product, work with it over and over. I mean, we've we've changed a number of things, I'm sure, as you've seen, been using Volley, just kind of a number of things. This as we get feedback, as we're learning from users, as we're seeing patterns in our data, we're like, oh, that didn't work. Wow, I can't believe that. And so it's just kind of this, you know, hacking growth and running another experiment, another experiment to see what does it take what's it take to, to get this thing to turn into a runaway train of organic growth, which is the, you know, the burden I have, or not the proof I have to bear for Series A, which we hope to raise this fall, and glad to say that we do have a nice little curve and a lot of the charts that matter of all the not not our vanity metrics, but the charts that actually matter, like retention and engagement and usage. So feels like we're getting there, but it's hard to wait for it. Like I said, when I know I can pay, you know, $100,000 and out of the wash, I get $180,000 or$500,000 or whatever, my you know, CAC to LTV is then it's, it's a different game. But hopefully, we'll we'll be able to play that game much easily, much more easily when we have this runaway train of growth, that we then build beautiful features on top of that people will no doubt want to pay for it, because they're just that good. So we're getting there.
Dale Majors:Thanks for that. I love it. And one of this the sense that I get from you as you share that is an I like how you caught yourself you said well, it's not a challenge or hard. It's just a new thing that you get to do. And I think because this is your, whatever fourth, fifth rodeo whatever number that is that you're realizing more and more that it is just about the building. One thing that I like to and I'm still not overly experienced, but I've had a couple different businesses and the thing that I've realized is I just love to build and I've had to become comfortable working day in day out having not arrived. Because I've arrived I arrived in one big way once and I realized it just wasn't all that enjoyable. So, but that I really craved something to be working on. So I appreciate your you sharing that. And also just, you had the patience of waiting because you have to have a true market fit. That's really interesting. I'm super encouraged for you, because I looked at my screentime metrics last week. And it was actually well, pretty surprising. But on my phone, I was on volley for six hours, it was actually the app that I had used the most on my phone. But what I also love about that is I consumed your last response, while just after working out while laying on the ground doing some emails, and I posted one of these videos while on a walk with my dog, it just really enables my lifestyle a lot more my active lifestyle. So I can be out and about I can consume at two times speed, and I can move work along listen well. Out and About. It's amazing. So I'm super hopeful for you guys. And that's really exciting. Thank you so much for the for those responses. And as far as you know, let me give you two questions now, actually. So, two things. I would love to hear more about your Why? Why is this exciting to you? And what kind of drives you day in day out to give your to give so much energy to volley? And then the second question would be, what would you consider your superpower? Something that that Josh does so well, that you've taken to your different ventures? And yeah, maybe that superpower and how you have leveraged it in building Volley?
Josh Little:Well, thank you for the Volley commercial there. My why I am lucky to have received my why or understand my why I didn't understand for a lot of years or what drove me and it's probably also the answer of why I'm still doing this cause I don't financially have to do this. You know, I read the book, Rich Dad, Poor Dad years ago, like 20 years ago. And I was like that, and from a kid coming from rural Michigan who didn't even know what an entrepreneur was or didn't understand that you could have your own business or you could be wealthy if you want to a like, I know that sounds crazy. But that's, that's where I came from. That's, that was my mindset. So I still haven't done it. I still haven't gotten out of the rat race, Robert helped me. But my why is to make beautiful things. And I say received because I was looking for my why, and I kind of went off on some people call it a vision quest, it was kind of a trip like that just a solo trip out in the wilderness. And and that was delivered to me in like the last 20 minutes before I had to get back on the road. And it was to make beautiful things. That's that's my purpose in life. And it just summed everything up. Like why do I make pickles? Why do I build four by fours in my garage? Why do I play the guitar? Why do I sing? Why do I - is to make beautiful things. And I can fulfill that why with a jar pickles, or a piece of furniture or a software startup. And it just happens to be that creating a company building something from nothing is the most taxing creative endeavor, it is the thing that challenges me the most as a creative to make beautiful things. And so that's my why, that's and, I, you know, I pride myself on being pretty consistent and doing what I say and you know, my first two companies were successes, both successful exits. And then my third is still a question mark. And that's a long story that that's like a whole other interview in a book someday but but it didn't work out. And I don't I couldn't walk off the stage with that being the last song I played so I got to get back up on stage and I got to rock this audience and and just like play an encore and it's going to be my best work ever. I'll start another Volley with my with with the answer your second question. Superpowers - Well, I'll tell you what other people say that they are. And I'll tell you what, I think they are what I pride myself on at least other people would say Josh is good at casting an infectious vision and recruiting an unbelievable team and evidence would say that's true. And I am able to get people that I shouldn't be able to get to come work with me because I'm, I can get them so stoked about what we're doing, and why that's going to change the world. People like Clayton Christensen, my second company, Bloomfire, was an advisor, or Robert Hookman, jumped into a company who's like a huge design thought leader. And, you know, Joe, Joe Wilson, or Spencer Smith, or Grue DeBry, who I'm working with, in this company in Volley, I shouldn't be able to work with these people. But I do so evidence would say that, that that is a superpower. But what I pride myself on and what I believe my true superpower, as a founder, as a CEO, as a founder CEO, is just being a generalist, I'm pretty good at all the things, not great. I'm great at a couple things, but I'm pretty good at the rest of the things, from sales, to marketing, to finance, to trademark law to whatever we're in, it's taken over a decade to get there. But I've got pretty good hands. And right now in Volley, I'm putting forward more work than I ever had. I feel like I'm doing the best work of my life. And because of that, we have a super super lean team. So the team, volley is me,myou know, our head of product designer, Joe, and then nine engineers, and we have a part time chief of staff who does finances and, and whatnot. But the rest of it is, you know, is is me. And so I think that's what's needed in the early days is someone who can, who is good at turning the crank. Now you would say, oh, that's inefficient, you shouldn't be doing those things. I don't know, I actually think I am the right person to be supporting users right now. And I need to be face to face with as many users as I can. And understanding their problem and hearing the same things over and over and watching for patterns. Like I need to be deep in the trenches. Yes, once we figure this out, once we've nailed the product, once we now product market fit, I don't need to be doing these things. And it's not the best use of Volley. But right now, that's what Volley needs me to do. So I do feel like I'm good at those early days, just doing all the things that the company needs me to be casting that vision, getting the team on, and like making it work for users, and doing all of the other things that you need from getting a trademark to make sure that your cap table is set up, right to raising money to whatever, whatever, whatever, it's a big job. And so I feel like that's my superpower. Because that like that is, that's an immense set of skills, that you have to mask that I really, I don't know how any 20 year old, could do it. Like it's such a daunting task, but they do write exceptional people, which is why they're remarkable stories and what which is why they're told.
Dale Majors:I love that idea of creating beautiful things. And, and how you relate that to make a you know, a great jar of pickles, or four by fours in your garage, or guitar or whatever. That's amazing. And I can relate a lot to that, or I just I love that sentiment of, of really enjoying all different elements. And I love that you're taking that, that it's a holistic approach of just how you approach life of creating beautiful things and, and that you're a creator in that way and making beautiful things. That's awesome. Thank you for sharing. And then as far as your superpowers, that's, that's super cool, too. I'm so jealous that you got to work with Clayton Christensen as an advisor. And I would love to hear more about that at some point. His book, how will you measure life is on my list of top five books. And every time I listen to it, I feel that it's kind of like a soundtrack for a good life. And I get different ideas as to how I should live differently. So I should probably listen to it again, because right now I am volleying and my children are downstairs. So I'll listen to that, again, I'm not perfect, but I love his book. And every time I listen to it, I feel like I'm a better person. So thank you for that as far as your superpower to engage amazing people. That's cool. And the generalist thing. I can relate a bit to that. And I'm seeing more and more in my business that I'm really good at kind of setting the table and getting some of the initial things going. So I'd love to chat more about that at some point because I think it seems like you're doing a really great job at it. And yes, I've been really impressed with you and Joe and my interactions with him as well. So congrats. And I think that's also really good point of you being face to face with all the problems, and completely in the know of what's happening with the users and Volley and everything else, and your ability to tie and synthesize all of those things together, that you can move a whole lot more quickly than, than building a lot of organization around you. That's awesome. That was, I think, very much my skill at my first company Bike Wagon. There's just so much stuff going on. And the fact that I could tie it all together, and that we could move more quickly. I think that's a huge asset. So yeah, maybe from the outside in, it might seem inefficient. But I love how you kind of clarified that and shared that. Thank you so much. Last question. Well, second to the last question. What do you like, as you look forward, you know, over the next year, what is your most important like, next key hire, in building the business? In building volley, I'd love to kind of hear where your mind is going. And what that next key hire is?
Josh Little:Well, the next hire that is key, we'll definitely be engineers at this point, Joe. And I still feel like we've got headroom to continue to run and run even faster than we are now. However, the next true key hire will be in this is really dependent upon where we truly find traction, nail product, market fit, killer use case for volley, something we're planning to monetize around will will be either head of growth or CMO to kind of build out that front of the house team. If we do it right, with Volley, which is a product lead growth company. We shouldn't have to have a very large team, they're just enough to kind of keep keep things moving forward. I mean, but you know, eventually, you know, Slack has a big sales team or whatever. Like, eventually we'll get there. But I just don't think that's going to be a heavy team, like I've built, you know, look at my last two companies where, where we had, you know, as many marketers as we had engineers, because we set up the whole circus because we had to, to generate leads, right? But Volley is running on its own power at this point. In fact, we can't even pay, like, we can't even outrun our organic growth with paid - maybe I've already said that. I feel like I already said it today, maybe earlier. But But yeah, give it given that, you know, I think we'll be able to have a pretty lean team, if we nail this thing. So yeah, CMO, head of growth.
Dale Majors:I love it. Thanks for that, Josh. I'm still just really impressed. And I've been thoughtful actually, this evening, about your, your perspective. And you know, Joe, and I have headspace. And we can still do this. And just this idea of staying lean. And being so involved not in all the nuts and bolts and everything else, as you're establishing the clarity for the your clarity, you know, for the company and getting product market fit. That's a really cool. And I think that's something that I've, I've had to experience a little bit to realize, and I just love how you're seeing that so deliberately, and making that just a deliberate strategy. So thank you for sharing that. Final question, before we close up, and maybe you can answer this question and then just close up with any other final thoughts or parting advice that you may have. And also to let people know how to connect with you, which is volley I actually want to share a Volley tip to before you do that, is I created a shortcut in my iPhone. That where anytime I type "Volley one" that sends people my personalized volley link. And I think it's you know, volley something forward slash Dale. And it's so cool, because I can text that to people and everything else. So anyways, here's the last question. When will you have arrived? What is arriving look like? And it also you may not have a an arrival point, but maybe what does that feel like? What does that look like for you personally? And the reason I asked that is I think it's really an important question for a lot of entrepreneurs, especially as they're building their first company. So I'm curious to hear your answer as someone who's building, you know, who has already built several. So when will you have arrived? And yes, if you could give us any other parting thoughts and, and let people know how to connect with you.
Josh Little:Well, that that is a hard question, Dale. I've been sitting here pondering that and I think it depends on what level Are you looking at that? Like, what lens are you looking at through because the truth is, we've all already arrived in the world, according to Josh, like when I believe we're all children of God, divine beings have infinite worth. And there's nothing we could do on this earth to, to change that status. And also, therefore, we're on an eternal journey and this, this is just a stop. And our goal here is to learn and progress and grow. And therefore we, we have not yet arrived in that sense. So but I know that's meta, and that probably what you're, what you're after here, probably more in this life's journey. And as I sit and ponder I don't know if this is okay to say but I feel like we've already the littles have arrived, like, I've, I've done more than I even knew was possible as a c minus student who had no plans to go to college that, you know, was just interested in dirt bikes and show choir. Like, I hadn't no idea what was on the table, or what was potentially on the menu, I just thought you, you either work at the prison company, or prison or the power company, or you become a teacher, or you work at restaurants and that those were the options in front of me. So from like, stepping into this life, stepping on the main stage of life, man, I feel like we've already arrived. We're blessed beyond our wildest dreams. And we have everything we could need or want. So in that sense, we've already arrived. However, as I said earlier, the, my, my life's mission, the reason I've been put on this earth is to create beautiful things. And that's an impossible thing to ever fully achieve. So in that sense, I'm continuing creating beautiful things even though I don't I'm not economically need to, for don't have to prove anything to anyone. I love creating beautiful things. And now I am just going for style and impact points. It's it's how beautiful and how big of a dent can this beautiful thing make? In whatever way I feel impressive to find that at the moment so so I don't know if that's a satisfactory answer. I don't know saying the law have already arrived as a pompous idea to set- Did I just say idear. I don't say that - idea. But I don't mean it in that way. I mean, in- ah, man, we we have everything we need to be happy now. It's just maximizing the potential. That's it. Um in US, how to get ahold of me, Volley's the best way if you if you download volley, you probably you can't get out of being in a conversation with me because you're in a conversation called Hello Volley, which is with the Volley team, which is, I'm very active in so that's the best way right now. Or stock man, LinkedIn. I'm active. I'm pseudo active there.
Dale Majors:I love that I'm seeing I'm seeing this and responding to it. First thing that's really powerful Josh, and really makes me think. I love the overwhelming clarity you have around your just your vision and your purpose. And thank you for sharing that. I don't want to say anything more to take away the impact that was so powerful. And I you know, I feel blessed to have been able to have this conversation with you. So thank you so much. That's a wrap. Thanks, everybody for listening to the podcast and we will see you later.
