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From Start-up Side Hustle to Main Gig

By Joanne Jacobs

This week’s Disrupt Podcast ‘From Start-up Side Hustle to Main Gig’ is a conversation with serial entrepreneur Jeremy LeBard.

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Jeremy LeBard

Serial Entrepreneur

Jeremy is an experienced Co-Founder with a demonstrated history of working in the retail industry. Skilled in Enterprise Software, E-commerce, Entrepreneurship, Enterprise Architecture, and Agile Methodologies. He is a strong entrepreneurship professional with a Bachelor’s degree focused in Information Technology from Charles Sturt University.

Gavin Heaton

Founder Disruptor's Handbook

Gavin is a marketing technologist, strategist and advisor. He is the founder of the Disruptor’s Handbook – a strategy and innovation firm that brings the best of startup approaches to the enterprise.


INTRO: [00:00:01] Welcome to disrupt the podcast for social, tech and corporate innovators.

GAVIN: [00:00:06] Hello and thanks for joining me on the Disrupt podcast. I’m Gavin Heaton the founder of Disruptor’s Handbook a strategy and innovation services firm that helps organizations shift mindsets, innovate products and respond to disruptive and uncertain futures. Today I’m joined by serial entrepreneur Jeremy LeBard. One of his start-ups, Read Cloud is doing amazing things in the world of education and he’ll be talking about that. But Jeremy also comes from a corporate background and he’ll be sharing some of the lessons he has learned about what it takes to make that leap from corporate to start-up and beyond. Now, speaking to people across the start-up ecosystem and also in corporates there’s a great deal of interest in the overlaps between the business, government and start-up worlds, but also a lot of misunderstanding and even fear. Well Jeremy has been living and breathing these multi-channel worlds for many years now and I’m sure you’ll get a great deal of insight from this interview today. Let me welcome Jeremy LeBard to the podcast.

GAVIN: [00:00:59] So Jeremy welcome. And maybe you could start by telling us a little bit about yourself.

JEREMY: [00:01:05] I think probably the best ways to explain it I’m an immigrant to Australia from 18 years ago from the U.S. although I did spend some time in Europe before that I started studying Technology Media degree in university in United States kind of wandered to Europe for a year and wound up in Australia and finished a bachelor of information technology degree and then moved into well actually I studied part time while I worked full time as a technical consultant and I guess I’ve been doing that pretty much since I’ve arrived in Australia and about eight years ago I started my first company which is still still running. Knock on wood. So all of this and yeah that’s that’s kind of a quick introduction to myself backwards. Being an infrastructure of technology.

JEREMY: [00:01:59] But I as you as you do over 18 years I’ve gathered some additional skill sets along the way.

GAVIN: [00:02:07] Well your story Jeremy is quite interesting because you don’t just come from a technology background you also come from a business background and now the world of start-ups. So your side hustle has become one of many side hustles.

JEREMY: [00:02:20] That’s right. Yeah it was a side hustle Yes. It was a side hustle for for a long long long time. Probably a good four five years of putting on the start up entrepreneur cake and jumping out the window at lunchtime for four meetings and working late into the morning and waking up in the morning and working and then doing a full time job.

JEREMY: [00:02:49] On the other side of it which which kind of grew into running a team of technical people and I was always very transparent I think about about what that I had a side hustle because I didn’t want there to be any problems and in terms of conflicts of interest. But I think for a good four or five years I was definitely putting in over 100 hours a week if not significantly more than that some weeks.

GAVIN: [00:03:13] So it’s amazing Jeremy because if we look at what happens with a lot of start-ups they only last 12 to 18 months before they fail been able to last for years before your side hustle became your main gig.

JEREMY: [00:03:27] Yeah yeah it was. I was too stubborn to give up.

GAVIN: [00:03:31] And so this first side hustle was called Red Cloud right. And it was about turning text books digital and making them available cross-platform into schools. And it took you four years you were committed to it.

JEREMY: [00:03:43] I couldn’t be persuaded that it that I wouldn’t be able to achieve it that my company a lot of people said Oh Amazon can do that and which they can’t. And they said well surely somebody else is going to do it but Nobody did. And as long as I kind of saw that end goal crossing the finish line was nobody running across it. I just kept doggedly pursuing that. And now the company has kind of grown up and run itself. I think the way I look at it it’s kind of like you don’t you don’t quit your job most of the time unless you’re a mom. Often but sometimes that happens. If you if you raise children and start ups our children say they don’t know how to feed themselves they don’t know how to walk and dress. And as the years go by. If you look after a start-up properly it learns to do all those things where eventually at some stage it’s telling you you know hey I got this. So that’s that’s the way I kind of look at side hustles now. It’s like having a child.

GAVIN: [00:04:47] I love that. So you are teaching it to walk.

JEREMY: [00:04:51] Because what happens is if it’s you get other people that start to help your sales come in because of other people. It’s a it’s a momentum building thing and you build up a body of knowledge and as it goes along that becomes a stronger body of knowledge where it becomes easier to get things done by reputation or by the IP that you’re building. You know that builds up over the years. All the people that join you.

GAVIN: [00:05:20] So you really are living and breathing the whole concept of disruption right. You’re creating a new industry you’re destroying old industries or old old habits. Disruption is something we should be worried about. Or is it something we should be looking forward to seeking out?

JEREMY: [00:05:34] I think it’s something we have to embrace I think and I think it is a good disruption was it was something that.

[00:05:44] Was only kind of pedalled in back you know like bootleg stores by people going let’s disrupt an industry but let’s you know bootleg some alcohol it was adopted by like the whole of the industry and it’s it’s really I think encouraging to see now companies like recently ANZ Bank has made a statement that they’re going to break up all their teams and small teams and run them each like start-ups. It’s too soon to figure out whether that’s going to be successful them or not for them or not. But it’s excellent to see large organizations you know in Australia adopting in a starter type methodology which is really for me it’s about learning and adapting to what’s new what you learn and that in that case creates a disruption.

GAVIN: [00:06:34] I think that’s a really great way of looking at disruption a way of learning, or accelerating learning.

JEREMY: [00:06:39] I don’t know who ever used to be that way but the way like in generations past from stories that I’ve heard it was like you’ve got a desk job and you did the same thing every day for 30 years. The world doesn’t work that way. You know it definitely doesn’t work that way now. And you know as computers are eating jobs and you know machinery is eating jobs and and new ways of doing things is eating jobs. It means that all of us have somewhat of an impetus or pressure I think to look at what we can do differently. And I think it’s leading towards a future where maybe everybody’s a creator everybody’s creating something and that creation whatever these adds back to the community and that’s really I guess a startup in a way.

GAVIN: [00:07:26] That’s really interesting point. So if we come from the world of corporate and we go into the world of start ups how well does the world of corporates prepare us for the world of start-ups?

JEREMY: [00:07:38] I mean because you’ve done this look I mean there’s an old saying it’s like you know do one thing do another thing because you don’t know which one’s going to succeed. You know it’s like you you know put out a few lines try a few different you know fishing lines try a few different areas try a few different things because you don’t know which one is going to succeed and whichever one succeeds then you know that you can you can go with that. I mean I think it goes back to I mean Steve Blank said entrepreneurs are born not made. I mean that’s quite a strong statement. He’s the grandfather of the lean start-up methodology. He started quite a few billion dollar companies so he’s a lot more qualified to say something like that than me.

JEREMY: [00:08:18] But I think the more that you embrace change and if you’re born into an environment that’s changing a lot then I think you’re more adapt to doing now and I do believe though that you can learn how to change and learn to embrace change. And so whether you’re born into having that type of personality or or or because you are forced to do situation all that you later on life decide to embrace it. I think that is the first thing is to have that type of mentality but also not like a get rich quick scheme I guess. Like I’ve seen my mother just join all of these multi-level marketing schemes when I was a kid. I’ve learned enough that you have to put the hard work in you know by watching other people. There’s no there’s no shortcuts for it because I’ve seen you know my mother telling me there’s no shortcut here there’s no shortcut for hard work you know. So I think everything builds on it. Like for me I went to school but also worked part time and then when I you know as a as a teenager and then when I went to uni I did the same. So it was always kind of like there was a continuous side hustle you know. And then I finished university and and I learned a lot of good things in university I learned a lot of good things working as a as a kid. I learned a lot reading and I learned a lot.

JEREMY: [00:09:43] You know I worked in a corporate environment and all of that I think builds you know builds on it then gives you the freedom to go and do what you want. And then there are all various different skill sets. And I think they all do facilitate each other but as obviously seen by like you know Mike Ken and Brooke said at lousier he’s created his own corporate beast. You don’t necessarily have to go work in corporate to do that.

GAVIN: [00:10:08] So you have a side hustle that’s turned into your main gig. But you also have another side hustle. You’re a serial entrepreneur you can’t help yourself.

JEREMY: [00:10:17] No. And I guess it’s the second side hustle is about facilitating you know my partner’s business and so it’s taking the things that I’ve learned and the struggles I guess that I’ve gone through personally. And then being able to do things for her what I would have been nice to have somebody do for me which is like I’ve been there before. I know this is like it’s hard. But if you stick with it you’ll get through it you know. And and so and I also enjoyed disruption as well.

JEREMY: [00:10:52] She’s changing perceptions about a specific type of product set in home decor and it’s a whole different field for me. My back is technology. She’s in marketing and had started this vision about three or four years ago. So I see a lot of parallels though in the struggle in the start up since I guess problems that you’d run into. Starting a new idea and pushing against what other people’s perceptions are. It’s pretty much the same. I guess it’s addicting. The adrenaline rush of doing something new. Probably for me but it is a lot of hard work.

GAVIN: [00:11:29] Well that’s been fantastic Jeremy and I really appreciate your insight because I think a lot of people will agree and be nodding their heads as they listen to these. So tell me has there been a particular piece of feedback insight that you’ve been given during your time that made a difference to you.

JEREMY: [00:11:50] One is to embrace mistakes. Mistakes will happen. Many many many mistakes and take them as an opportunity to become an expert you know the more mistakes you make the more of an expert you are because you know how to not do right. Better than anybody else you know. So for me that’s probably that’s that’s probably the biggest and that is really just about embracing change and being able to set feedback and you know and then evolve. I think it’s very important not to lose your ego because you have to go wrong. You know this isn’t working and let’s change you know the strategy the tactic Let’s learn from this what did we learn from this. You know so that’s kind of it for me the other others like build build a team around you. Like I said in another piece of advice I heard. But after I started my company but thankfully I kind of intuitively embraces it surround yourself with people you know the the right number of startup people you know running and starting a start-up is never one that’s another quote from Steve Blank with Redcloud. I had two fellow founders alongside me and thankfully they’re good people as well because I’ve also heard of stories where people have partnered with the wrong people so partner with the right people and try and make it more than one. I’d say even more than two. You can’t because it is a hard road. Somebody is going to drop the ball and somebody else is going to need to pick it up.

JEREMY: [00:13:22] And that’s why I think a lot of start-ups don’t surpass 12 months is because they don’t have somebody to pass the ball to when they’re exhausted and they’re down and they need they need somebody help pick them up.

GAVIN: [00:13:35] I think we’ll have an entire podcast devoted to that topic.

JEREMY: [00:13:38] Yeah. Yeah. Yeah I think I think it’s one of the most important things you know teamwork. And actually it’s kind of like the you know in the Army the Marines and the Navy SEALs and it’s all very much a core part of how they run is that they run as a unit in a tight knit unit and they are in a changing environment.

GAVIN: [00:13:59] So Jeremy I would like to be respectful of your time. So perhaps we could wrap up now and I just want to know from your perspective is the one secret fact something that you know about yourself that a lot of other people would not.

JEREMY: [00:14:14] Secret fact!

JEREMY: [00:14:19] I think I try and run my my life by being a sharer or being an oversharer. That has its own drawbacks. I don’t know. I mean it’s probably maybe something to talk about but I guess it came from like a very poor family. And and even though I guess when I was in corporate world and start ups and so on. It’s not something that you know you talk about. But I guess it’s something that shapes the way that you view when something bad goes wrong you’re like well I’ve seen way worse than this you know. So maybe that’s something secret that we always try to go around. Tell everybody all the good things that we’ve done and where the good places we’ve come from. But I think it’s important to be able to also acknowledge you know where you’ve come from and envy that so maybe you like somebody actually compared it wants to like a lotus like you’re a Lotus’s comes from the mud but it lives in the sky you know and you can embrace both sides which I think is a very it’s a beautiful analogy.

GAVIN: [00:15:21] So whereabouts on the Web can we find you Jeremy. Whereabouts can we find your oversharing profiles.

JEREMY: [00:15:31] Not very good at self marketing it’s not my thing. I like to focus I guess and growing companies but I do have an Instagram page LeBard. LEBARD. it’s very normal personal and I’m on I’m on Linked-In. I do occasionally meet up with people on Linked-In and talk about start-up stuff and see how if there’s any collaborative advice that would be mutually beneficial. That type of stuff.

GAVIN: [00:16:00] Brilliant. Thanks again for your time Jeremy.

GAVIN: [00:16:02] I’ll be sure to pop those profiles into the show. It’s. Jeremy has a great view on innovation and start ups and the power of persistence and hard work. But he also talked about the importance of learning for those of you who have an interest in corporate innovation and how the tools and techniques used in the world of start-ups can be applied in the corporate world.

GAVIN: [00:16:20] Be sure to head over to our Web site to view and download our libraries of books for disruptors at disruptors handbook dot com. I look forward to speaking with you again next week.

The Disrupt Podcast is for innovators who work in business, government, technology or social impact. We believe that with the right tools, approaches and inspiration you can get scale your impact and our guests have the experience and expertise to help you do just that. You can listen online or subscribe via iTunes.

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