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Ep: 195: How this passionate entrepreneur help businesses scale up with Todd O’Brien

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In this episode, I speak with Todd who is a passionate entrepreneurial sales and marketing leader with over 25 years of experience. 

Todd has worked in very large organizations but also launched multiple businesses with some successful exits to Flipcart/Home Depot. 

Listen on to find out out how Todd has been able to help businesses scale. 

Listen Below:


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My Offbeat Journey: 2020 Recap



Hey everyone. Thank you so much for being here. I am really excited to speak with my guest today, Todd.

Hey Todd, how are you?


Hey, I’m doing great. It’s great to hear from you.


Can you tell us about you and why you live an offbeat life? 


Yeah, I love the idea of an offbeat life. I think I’ve always been a little bit of a nomad in my life in a way, wanting to do things a little bit differently. Living an offbeat life to me has always been about freedom.

I’m a big believer in the freedom of your schedule: you own your schedule, it doesn’t own you. Take life by the horns and just be out there and enjoy that freedom because it’s a huge value for me. Then, it made me really want to choose to live this sort of offbeat remote digital nomad kind of life 

And even the jobs that I’ve chosen, even though I was running a large company. We did this version of a free work style where you just get the work done. It doesn’t matter whether you’re doing it at 2 a.m. on a Saturday – it’s up to you. You work your life around your job instead of your job rules your life. 

So this is why I’m always chosen to do it for myself, it’s this value of freedom.


It’s so interesting how for most of the jobs at 9 to 5, most people are really unproductive, right? Because it’s not really working for when they’re at their most productive, it’s when you’re told you should be productive. 

So for someone like you, Todd, who did a workaround and you ran a company that was doing this, that is pretty incredible. And that’s pretty unorthodox for a lot of companies. 

How did you manage to do this and realize this was more productive? 


It’s all about the people that you hire as well. One of my really good friends, her name is Christina, she’s from Slovakia and I met her when I lived in London. That in itself, that phrase that I just said shows you that she is this nomad and I am as well.

We met in London randomly, we started to work together. Just hiring people like her and other great people to work within the company who just had the same value of it’s about the work we’re doing, it’s about the momentum, or wanting to create. It’s not about the number of hours we punch in and sit behind the desk. 

I mean, I’ve done so much of my work from coffee shops, from hotel rooms, from outside in a park. It’s crazy. Here in Austin, they have scooters everywhere, electronic scooters?




And so there are times where I’m just like, “I need a bubble tea,  I need to get on a scooter.” And I need to just ride around the Capitol and clear my head. I’ll stop at the Capitol and set an alarm to take phone calls. 

It just makes more sense to have that freedom and give yourself spaciousness. And the way we were able to do it is by hiring like-minded people. 


I can agree on the bubble tea and working from anywhere.


There’s nothing better than bubble tea outside -that’s my philosophy.


I can agree with that. Check on that.

So, Todd, let’s start from the beginning because a lot of people who are listening to this are asking, “Okay Todd, that’s really great that you’re able to do this. You can ride around in your scooter getting as much bubble tea as you want. But how did you start? How did you become a remote worker? How did you not end up in a 9 to 5 hating it and you do being miserable right now? 


Yeah, it’s a great question and I definitely lived in the 9 to 5 world and hated it. It’s a lot of the driver behind why I choose not to do that anymore. I think it started early when I got out of University. 

I spent about nine years traveling and working. I’m a musician so I was traveling early with a band but I was working with teenagers who have a lot of trouble in their life. We were putting together bands and using music as a sort of therapy a little bit.

That did not pay the bills but it was a lot of fun and I really enjoyed it. I kind of always had this notion of just like really being free. So when my kids were little I needed to put diapers on them, I needed to feed them. I decided it’s time for me to get a real job and I went to work for this company – Dell.

I still have a huge passion in my heart for Dell because Dell really focuses and appreciates work-life balance. They always have, even from the day that I started. I think everybody has different experiences with the same company, but that was my experience. 

My experience was they support it, they really wanted you to have a work-life balance and I chose that. I had a job that yes, it could have been nine-to-five but I worked East Coast hours and I was in Central Time. So I went to work at 7 and I left at 3:59.

I just worked really, really hard during those times. And what I think that taught me is that when I was doing a job later on where I had more freedom and more space, it’s not about when you put the hours in, it’s about how you put the hours in and how effective those hours actually are.

And I started really thinking about this but what really shifted my mindset is when I read Tim Ferriss’s book The 4-Hour Workweek. and I started going, “This is the philosophy that I felt and had, just didn’t know how to put the context and words around it.” 

So what I would say to people, to your question, who are out there going like, “Yeah, how do I do this for myself?” is – it doesn’t happen overnight. You have to start slowly, you have to really find out what values you have. And if that doesn’t fit in the company that you’re in, get out and do something different.

Work for a company that supports your values and move your way into this life and the life that you actually want where you can do work-life balance. 


I think this has happened to me and a lot of people that I’ve spoken to: you see other people living out their dream like you and think, “Oh, well, for me that’s not going to happen. Maybe I’m not a nine-to-five that just doesn’t translate to remote working. Todd works for Dell – I don’t do that. I’m not a technical person.” 

And there’s always a barrier not even that other people put towards you but you put to yourself because they can easily be remedied. I’m pretty sure you have skills that can be transferred into remote skills, or you can actually learn them online. 

There are so many freebies. Like there are so many free courses out there right now that you can learn. If you really want to do it, you’re going to do it. So I think for the most part it’s just mental blocks that are really stopping us and saying, “Okay. Yeah, whatever. That’s not going to happen to me.”


Yeah. I want to add to this as well too. I like what you’re saying. and what I want to add is it’s very much a mindset thing. It’s very much how you approach it.

I had a really high-level job at Dell 10 years ago. I had a team of people and I hired, I thought, a really stellar team that was able to really do the work and do the job well. They did so well, they always made me look good and I also empowered them to actually take on things for themselves and do it the way that they wanted to do it. 

I gave them a lot of space and freedom to do it. And during that time, that 2 years, I spent very little time at the office. Most of my time was spent with either the team being remote or we would have certain times where we came in and met in the office – kind of get that office feel. But we did a lot of our work that could be done from home. It could be done from coffee shops. 

And there are times where I did one-on-ones over a trip to Sonic. I know it sounds crazy but like, “Let’s get out of these four walls. Let’s walk across the street and set outdoors, grab a Sonic, have a drink, and just sit there and have our one-on-one there.”

It just created more spaciousness. So it is a mental thing that you sort of have to mentally decide you’re going to create space in your work.


When you work from home, Todd, because this is what a lot of people who are just starting out, one of the setbacks that you go through is staying motivated, being productive, especially when you don’t have co-workers to push you through or a boss, how do you do that for yourself and also the people that you work with? 


It’s an awesome question and it’s all about being aware of where you are at that current state. So what I mean by that is I may be sitting at my desk and I’m just not feeling it. Like, I can’t think, I can’t even write anything on a whiteboard, I can’t type an email – I just can’t do it right now. And it happens to all of us, especially when you’re working from home, just not feeling it. 

The best thing you can do for yourself is get up and go ride your exercise bike for 30 minutes or go down and have yourself a Topo Chico. Just take a little break and just refresh. Work from home, I think, a lot of times means work always like you’ve got to always be working 24/7 around the clock. And that’s actually really hindering working from home. 

So it’s kind of about managing your energy, managing yourself, but more than anything, being aware of when you’re pushing yourself beyond your limit. Because then you start becoming reckless or reactive rather than being creative.


Creating a pattern for yourself and also having a schedule is definitely something that we all need. I think when I first started doing this for working from home or not even starting, before that I thought, “Oh, I’m going to have so much freedom which is going to be all great.” 

And then you realize that if you don’t set a schedule for yourself it just goes downhill from there and you have to be even more diligent than when you were in your 9-to-5. Otherwise, you’re just going to be like Netflix and eating, that’s all you’re doing. 


Yeah, I agree that having some form of a schedule is important to some people but I also want to highlight that other people probably thrive in a less scheduled, more broad view. So for instance, maybe Mondays are the day that you do XY, and Tuesdays you do this.

I’ve always been more motivated by the task of what I need to do rather than the amount of time or the time that I need to sit down. I would literally die if I said, “Okay, from 8 to 4 or 8 to 5, I’m going to be in my office and that’s my work time.” 

That wouldn’t work for me because to me that’s like being handcuffed to the chair. It would be better to say, “These days I’m going to get these things done. I’m much more motivated that way.” 

However, there are people who are very motivated by a very tight schedule: from 8:30 to 9:00 I need to do these emails. Okay, great. So I would say the personality type probably has to set whether the schedule is tighter or looser. 


I love that and also one of the things that a lot of remote workers and location-independent entrepreneurs really love about this lifestyle is the freedom to choose how you schedule your days. And this is one of the best things about this lifestyle, right? 

Because you can’t do this, you can’t take a break in the middle of the day and just start bicycling and getting a mochaccino and bubble tea somewhere. So I love the fact that we become more productive when we have more freedom to do what we want. 


Yeah, I fully agree with that. It’s empowering when you can give yourself the freedom too. 

Because there are times where we get into this I should mindset: I should be doing any work right now. I shouldn’t be doing this. I should be doing that. As opposed to what’s possible: What’s possible for me today? What would I like to see done today? What are they going to require of me? What energy am I going to have to put into this to actually get this done? 

This is a much better, more productive way of thinking than I should really be doing this ‘Cause then it’s just easier to put things off. It’s easier to procrastinate and trust me, I’m kind of a huge procrastinator but I’ve learned how to manage my energy in a way where I know what gives me life and I know what doesn’t. 

And I’m going to spend as much time on the things that give me life because then it helps me do the things that don’t give me the life that you just have to do. 


It definitely makes you learn so much about yourself, right? 


Yeah, it does.


It’s a good thing though. You learn the good and the bad things about you and you learn to change that too. Otherwise, you’re just not going to thrive.


Yeah, for sure.


So right now, Todd, as an entrepreneur what has been the biggest setback that you are encountering and how do you handle them? 


As an entrepreneur right now there’s a huge setback with what’s going on in the world, with the pandemic. Recently I had some funding, I was working for a company and I was setting up something here in the US and that funding got pulled because of covid. 

So I found myself with really nothing to do and I need to start thinking about what I was going to do next. And I have the initial approach of, “Oh my gosh, I got to go get the contract with somebody. I got to figure something out.” 

And I finally was having this conversation with my wife and I was just like, “I wanted to take some time off.” Like 8, 9, or 10 weeks straight off and I’ve never done that in my life and I wanted to take this sabbatical next year in 2021, and I was actually planning it. I said, “You know what? I’m going to look at this as a gift that maybe this is the time that I do it.” 

So I actually just came off of an 8-week sabbatical. For the last eight weeks, I have literally done no work, nothing, which is the first time I’ve ever done that since I was 15 probably. 

And so I think, as an entrepreneur, you ask a question: What’s really impacting me right now? What’s impacting me is how do I now take what I’ve learned over the last eight weeks and re-engage into doing something else that I know requires a lot of energy. Starting something, putting something together, working for somebody – whatever requires energy. 

So, how do I take what I’ve learned from the slow, this pause that I’ve had in my life this positive had in my life to actually bring that into what’s next for me so that I can bring some of the joy, some of the freedom, some of the ways that I’ve been living and experiencing the last eight weeks into the work that I’m about to approach. 


Being grateful right now is really hard because there are so many losses and I think what you ended up learning is this is what you needed. It’s kind of crazy how even in moments like this we can find something to see as a positive because it can really easily be depressing and you can go down a really big hole of darkness when things like this happen.

So it’s always good to look at and obviously, it’s not always sunshine and rainbows, but that’s not the only thing we can think about, hopefully.


Yeah. And I think one of the things that it taught me is as an entrepreneur, you kind of work for the moment and you work for the pot-at-the-end-of-the-rainbow. Usually, that’s what you’re working for and you don’t spend a lot of time planning for something like this happening in the world.

And I think that it’s going to make me rethink how I’m positioning myself financially, how I’m preparing myself in the future so that if there is a loss or a cut or something like that, it’s not such a big hit. It’s not such a drastic hit.

I know a lot of my entrepreneur friends are really struggling right now. They’re trying to get funding. So I think it’s important to prepare and plan in your life even as an entrepreneur and we don’t always do that. 


So, what would you say something that you learned with this pandemic, this crisis that has happened that you would be changing in your business model that will help you just in case anything happens again in the future? 


I think that there is a little bit more conservative approach that probably needs to happen from an entrepreneur standpoint and being an entrepreneur is risky anyway. But there are ways to sort of hedge your bets a little bit too. 

And so I think for me it’s probably more just looking at what is sort of the path forward. How do you take that with the riskiness of being an entrepreneur but still a little bit hedging your bets too. Meaning maybe you’re not going to go out so far on the limb before you start sawing it. 

There’s this idea of an entrepreneur jumping off the mountain and built wings on the way down. Let’s maybe have at least one wing built or have something prepared so that when we jumped off that cliff there is some fallback ‘cause it’s really uncertain right now. 

I think it’s uncertain probably for the next couple of years in this environment. So how do we, as entrepreneurs, as founders, as people who are doing things on our own, approach this a little bit differently?


Again, so much learning from all of this that we can really take into the future into our business that in some ways is a blessing in disguise because now we’re more prepared and unfortunately it had to go to this. So hopefully we’ll just become better and in the future.

So, Todd, before any of this happened did you and your family travel while you worked? And if you did, what were some of the best places that you have found that you were able to balance both works and play at the same time? 


Yeah, it touches on something because I so miss traveling and we have traveled the world. We’ve traveled all over the place. We lived in Dubai a couple of years ago and then we lived in London before that a couple of times. And then we just spent a lot of time traveling. 

Like I said, I used to work on the roads like crazy. I might be in Taiwan doing some work for the US or I might be in Australia doing something. I really miss that freedom and that experience of being able to sort of work anywhere.

And I think it’s important to kind of highlight that it’s not necessarily about a place and when you say what are the best places. I mean, obviously, there are incredible places like Singapore, London, Berlin and different places around the world. South Africa where it’s just an amazing place to work.

I think the world is your remote right? It’s not necessarily a specific place. It’s how you show up in that place and it’s how you step into different cultures, learn from them, and not expect them to be a western culture if you’re somewhere that it’s not. And just really being open to the people and the environment. It’s such a learning to be able to travel and do this sort of stuff.

Yeah, I really miss that. 


It’s definitely a privilege for all of us to be able to travel and see all these different cultures and I do agree with you that you can’t expect a place to be similar or the same as where you come from. Otherwise, you shouldn’t travel if that’s what you want, right?

It’s kind of crazy to me when I see people complaining about certain things and I’m like, “Well then why did you come here? It’s going to be different.” 


Yeah, I think we expect a lot of times that when we go it should just be like our way and it used to frustrate me a lot. When I lived in London, I would see so many Americans who came to London and be like, “Oh no…” I see why the Brits kind of rolled their eyes at us when we come because they’ll be saying things. doing things, and just expecting things to be a certain way.

Step into a country, look, and appreciate what’s different about it. When I went to Dubai. I mean, wow, it’s like a different world – way different world. But I have literally met some of my best friends in this world in Dubai.

And I think it’s just being open to a culture, being open to learning, and not expecting something’s going to be a certain way. I intentionally did not look for groups of people that were like me.

For instance, when I lived in Dubai, I had a lot of people like, “Oh there’s an American group.” I’m in Dubai, I don’t really want to be around a bunch of Americans. I’m an American but that doesn’t mean that I have to take my bubble around the world with me, right?

I did the same in England. Our kids went to British schools when we were there and I think it’s important just to not become that culture but embrace it and appreciate it. 


I love that type of traveling when you’re really going out of your comfort zone because that can be very hard especially in the beginning when you’re trying to find your footing in a different country, especially if you don’t know the language and how people behave and act. It’s also a form of respect, right?

It’s really how we should think about this. When you’re traveling to a certain place you have to respect it like you expect people to respect you when they come to see you. It’s like being in somebody’s home. You don’t start nagging or complaining about things – that’s just plain rude. 


Yeah. Also, there’s a couple of practices I did when I traveled all over the world. I would do research at a time. I try to find somebody who maybe was in similar work that I was or had a similar hobby or passion as mine. And I would Google really fast. From LinkedIn, Facebook, whatever. And I would connect with these people ahead of time. 

For instance, I connected with this guy who had a really interesting background in Russia and he had been ousted because of some of the things he had said. He was a journalist and had been ousted from his job because he had said some really derogatory, in their mind, to the Orthodox church and it kicked him out of being a journalist.

And I was like, “Wow what an interesting dude. He’s really into the art of discussing something.” So I just sent him a note and connected with him. I said, “Hey, listen. I’m going to be in Moscow. I would love to meet you for coffee.” And he did, he met me. 

And then I asked those people like, “Hey, what are the things I should see and what food should I eat?” I did this a lot traveling around the world and I really encourage nomads and people who are traveling around. 

They kind of probably know this naturally but for people who are wanting to do this, just reach out to people with who you might share a passion or share an interest and connect with them before you go to that country. And you just never know.

I’ve had people take me to crazy places that I never probably could have got into if I didn’t know a local.


It’s really true. You already have a built-in friendship once you step foot in that country, which is incredible, right? And with social media now, with Facebook groups, with Instagram, there are so many available spots for you to find these people. It’s not like 30 or 40 years ago. You really have to dig into it.


Now it’s easy. 


Yeah. It’s so easy.

That’s a really good tip, Todd. And yeah, definitely do that once we can start traveling again.  We’re waiting for that to happen. Hopefully, it’s not going to take too long but who knows. We’ll see what happens. 

So, Todd, Let’s fast-forward to 30 to 40 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


Well, first of all, I hope I’m still alive in 40 years. I’ll be 90 years old so that would be amazing. It’s an interesting question because I’m not huge like, “legacy I have to be remembered for something” kind of person. I know that may sound a little weird but I’m more about “what am I doing today with the people around me”. 

The important part to me is that I have had a really good life, that I have been able to influence, impact, and inspire the people around me who are in my family, who have worked with and for me, and the folks that I worked for. 

I think what I would want to be remembered for is the person that was fun and inspiring and gave people some creative thinking around how they can live their lives. 


That’s an incredible legacy especially if it’s directly within your family and your children, that really, for you, at least, makes a huge impact because it’ll be taken down to generation to generation and how your children will also be living their life, which is really beautiful. 




Thank you so much, Todd, for being here with us today. If our listeners want to know more about you, where can they find you? 


They can connect with me on LinkedIn, it’s probably the best place and I would love for anybody to connect with me. You can just check out my LinkedIn and we could share some conversations or network and that would be awesome. 


Perfect. Thank you so much, Todd. We really appreciate you for being here and sharing with us your incredible story. 


Great. Thanks so much for having me.

Listen to Todd’s extended interview where he shares how to build, leverage, and share your network as a remote worker.

What you’ll find:

In this episode, Todd talks about taking your network to another level as a remote worker. Learn the strategies in building and sharing your network straight from Todd’s arsenal of experience.

Follow Todd:

Show Credits:

Audio Engineer: Ben Smith

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