Life Profits

Geoff Roberts: This is a podcast about entrepreneurship, but rather than being yet another, how to get rich show, this podcast focuses on people who have used entrepreneurship to build interesting and enriched lives. This series will introduce you to people who will make you reconsider your own definition of entrepreneurial success because business profits are great, but life profits are even better.

Adii Pienaar: Cool. So Jeff, in this episode, one thing that I. Would love to chat to you about is this notion of like, what comes first, actual profits or, or life profits. So I want to read you a quote from something you wrote, and then I want you to take us back to that moment in time and just tell us what the other things were that were going on in life and going on in your mind.
When this played out, you wrote, I was lucky to work for a company earlier in my career that care more about Jeff, the person and Jeff, the marketer. I asked my boss to work remotely in [00:01:00] 2013. Clearly chasing life profits qualify. You say, I want to move to San Diego. I was ready to walk away from an amazing gig, but I was given the freedom to pursue what was best for my life.
Holy hell. That was empowering and reflecting on my own behavior. It made me work that much harder for the company. Like tell us more about that moment in time.

Geoff Roberts: Yeah. So I, I started my career in really 20, 2010. I had graduated from college in 2008, right as the economy was tanking, sort of didn't know what to do, frankly.
So I went back to school and got a graduate degree in business and things still weren't great in 2010 to be frank. And I went out looking for a job. I got offered a job at a software startup called Buildium. If I'm honest, it sounded horribly boring to me. I don't describe myself as like a particularly techie person, but without knowing it, I stumbled into a pretty incredible [00:02:00] situation.
I joined as employee seven or eight, something like that. It was a very engineering heavy company at that point in time, they'd found product market fit, and they basically said to me, Go figure out how to make this thing grow faster. And I recognized that I had fallen into a good situation relatively quickly.
But even prior to that, I had been interested in going to live somewhere else. And San Diego, California specifically was, was top of mind for me. I grew up on the East coast of the United States near Boston and had lived my whole life there. So it was really nothing more than I was, you know, fresh out of school, wanted a new life experience.

My now wife was on board, she wanted to go too, but suddenly I found myself in this great job and not wanting to kind of shoot myself in the foot. I, I worked in William's office in Boston for three years, but we still had this, this goal of doing something different with our lives in mind. And one day I decided, [00:03:00] you know, it was, it was time to do it.

It was sort of the first time in my life where I said. I've got this good work situation going on, but my life is more important than my work to me. And I recognize that this job is great, but I'm going to walk into my boss's office and, you know, politely issue an ultimatum, which I didn't, you know, come across as giving him an ultimatum whatsoever.

I just came across as saying, this is something I need to do with my personal life, and if that means I can't work here anymore, I completely understand it. But. I was very surprised. I thought the day that I walked into my boss, who's now my co founder at Outsetta, his name's Dimitri, I thought the day I had that conversation, you know, it was going to be pretty clear.

That was the end of my time at the company. And I was okay with that, but to my surprise, they like completely shrugged and were like, if that's, what's important to you, you've demonstrated enough here over three years that we want to give you the flexibility to do the things that you want to do. And. I remember kind of [00:04:00] skipping out of their office that day, genuinely shocked and surprised.
I mean, this was 2013 before remote work was the norm for almost anybody. And over the next couple of years that I continued to work at the company, I worked harder than ever. I already was working hard for them, but I just kind of looked back at my own behavior and said, wow, they, They did care about me as a person.

They did give me sort of abnormal levels of freedom. And because of that, I already felt a lot of sort of passion for this company and loyalty for this company, but that's just 10 X it. And that's something I've reflected on a lot as we've built outside. I've said, how do we get people to, to feel that way and sort of act like owners in the business because they want to, because they see sort of this.
Symbiotic relationship between the employer treats them really well. They want to sort of treat the employer really well in return. So that's been kind of paramount to all of my interests in company building at [00:05:00] this point.

Adii Pienaar: I am, I want to firstly, like, just underline something there. And then I, then I have a kind of a question that I'd love to kind of pose to you based on that.

But the thing I would just want to underline there was that I think it's easy to sometimes Life profits as being this very grandiose thing, like this, this massive thing that needs to be true for us to pursue it. And it sounds like in your case, this, this literally just was a case of, I just want to move east to west coast.
Right. And I understand like that, like there's logistics as well, like that in itself is not a tiny thing, but it's not grandiose. It's not, it's not flashy. It's not like it's, it's something highly achievable. Right. So, uh, and I think that's important. I think in pursuing life profitability, it's often those things that.
We consider a very normal kind of, and within reach that we should just prioritize. Right. But when I actually wanted to ask you there, Jeff was a bit of a kind of chicken egg situation. When you spoke to Dimitri, you demonstrated enough value to the company. So they said that, sure, like we can indulge you on this [00:06:00] front, right?

But that proposes the same thing, right? Like, which is like, I need to build up enough capital or profits. And only then I can do the life profit thing. Right. Like, do you think that is the case, right? Or is there some other equation in which we can think about in terms of pursuing life profits?

Geoff Roberts: I think in the case of the specific story I told, Buildium was a company that prioritized life profits without putting specific language to it, without putting maybe specific practices in place to support it in a lot of ways.

And because I was asking to do this remote work thing, which was abnormal and not something really other people in the company were doing. I think it certainly helped that I had spent a few years at the company. I had built those relationships. I had done good work. I think they felt more comfortable giving me that sort of [00:07:00] opportunity to chase those life profits as a result.

Do I think this needs to be like a permission based system? No, I don't think so whatsoever. I don't want to create a workplace myself where people feel the need to have to like prove themselves in order to Be able to prioritize the things that are important in their life. Part of the feeling that I have is prioritizing the things that are important in your life is what you should be doing.

No matter what, if you're, if you're not a good employee, you're just not a good employee.

Adii Pienaar: Yeah. And what actually, and I'm totally just riffing off of what you said there, Jeff, I, I think like the way that I maybe implicitly did that in my businesses is like, I probably kind of looked. To hire the team members where the individuals already had some clarity or some ability to communicate what, you know, what is unique about them and how they think about life, right?

So, and then it becomes a [00:08:00] bit of a self fulfilling prophecy. Then you kind of avoid that. That chicken egg situation somewhat, then it's not permission based and it's inherently baked into the process who

Geoff Roberts: they are and your understanding of them as an employee. Yeah, that makes sense.

Adii Pienaar: Exactly. So we spoke about that first big sheet of life profits, right?
Well, she were. You're working on, on building, I know that Buildium was a big influence on how you've gone out and built outside that, like, just take me through that transition and progression. Like what are those things that specifically, then you experienced yourself within Buildium as a team member and employee that you've replicated and then evolved with an outside essence?
Yeah.

Geoff Roberts: So Buildium was more, Traditional tech company in terms of how it was organized, in terms of how it operated, the company was bootstrapped to several million dollars a year in revenue, raised several rounds of funding, had typically organized departments that you would see in a normal tech company.

But there [00:09:00] were certainly elements of the culture and also how they granted equity to employees that were sort of ahead of their time. They were an LLC and they granted what's called like a incentive membership unit, which basically acts like equity in a business, but it's structured for an LLC specifically.
They were definitely taking a very long term approach to business, even though they were raising funding. So there were bits and pieces that we pulled out in terms of the ownership structure and how the business was set up and those sorts of things. But really it was looking back at that experience and saying, okay, if we can start with a perfectly clean slate, what would we want this to look like on our next rodeo?
And the main thing honestly was wanting to stay small. We just kind of said. When we were a team of 20, it was more fun than when we were a team of 200. And it wasn't about external financial investors being involved or anything like that. It's just the dynamics of working in a small team [00:10:00] versus a large team.

There's more bureaucracy, more admin stuff, just more headaches aside from the actual building and doing of the work. And we said, okay, let's start with this sort of self imposed constraint of Let's say we can only grow to 20 people, but we still want to build a big successful business. How do we go ahead and do so?
What needs to be true? And the things that fell out of that pretty quickly were we need to hire really senior people. We needed to hire excellent, experienced people. We weren't going to have management layers. We were going to have Excellent individual contributors. So we kind of started there and said, okay, how do we attract those types of people and get them to act like owners?

So we came up with this standardized salary that we offered out set up as well as issuing equity to everybody in the business on the same terms as the founders. So today outset is this flat organization. Everybody earns the [00:11:00] same salary. Everybody's working for equity on exactly the same term. So it's almost like everybody is a co founder.

We use the word co founder to refer to the three of us that started the business. But. Everybody is essentially on level footing and that's, that's been kind of the magic of the company and in so many ways, people always look at how we're structured and how we work and they say, oh, that's not going to scale.
And my immediate response is it doesn't need to scale. We want to keep this team sort of artificially small. And our objective today is really looking at the business through the lens of. If we're only going to grow to 20 people, how far can we push this business within that constraint? So just the desire to stay small has been the most influential thing on us.

Adii Pienaar: That's fascinating, by the way. And I know that many of those individual components you've shared about in detail. I'll set a blog and we're going to jump into some of those things a little later in the conversation. I'm most curious though, [00:12:00] you speak about using the initial heuristic and saying, if we start off, what does it need to look like?
Right. What needs to be true at the start so that we can essentially aim for the kind of the outcome or the environment that we hope to achieve? Like how much of what you just described. Was present in kind of your day one or in year one versus what came kind of also words, right? Is it just like you just had this perfect clarity and you've just executed perfectly on that plan or like there is the road to today?
Like somewhat more entangled

Geoff Roberts: Yeah, honestly, it was very prescriptive ahead of time. If you actually go back on our blog and read the first two blog posts we ever published, we talk about this stuff in eerily similar language to exactly how it's played out. And a lot of people early on, even rightfully so questioned us and brought that up.

They were like, you're thinking a lot about this organizational design stuff and this compensation stuff and how [00:13:00] you work. Before you even have a company. And the truth is that that was the truth. I'd like to say, you know, that drove our success in some way, but I don't think that's true at all. I think that was really useful to our founding team in making sure we were all aligned in terms of what we were building, why, what we wanted to get out of the experience.
And I would say in the early days, there was little value to this whole model. I mean, when you're a three person company that we started with it, there's not much organization that goes into any of that, but I think it was paramount. And we were saying we were going to build something for 15 plus years.
And we were making a 15 plus year commitment to one another as co founders. And having that level of alignment early on was massively, massively, massively helpful. We can get into all the specifics, but. Outsetta has grown slowly and steadily since it started. It's never been a rocket ship, [00:14:00] but especially our first three, four years were pretty darn lean.

We had some, some tough times without question, but we've never had any sort of significant co founder conflict in any way. And I think it comes from making sure we had that level of alignment early on. Yeah,
Adii Pienaar: the part that firstly resonates there, Jeff, is that, I mean, I shared in the previous episode that, you know, a lot that I experienced in Woo was that we were learning and building on the fly, right?
And one of those things, for example, was things around, you know, culture. This is a great, you know, Jason Cohen, now of WPNJD, first found the code via him. He says that you have a culture, whether you do something about it or not, right? Like, so, and that was the first idea, like, as I started building on Convergio, which was like, I need to be very clear from day one about what I want to at least try and achieve here, because if you don't have that kind of clarity early on, it becomes so much harder later.
And I was [00:15:00] solo founder on Convergio because I acknowledge the challenges we had with, we were in terms of that co founder alignment, right? I think the way I now think of it is. It is much, much easier to proactively align or kind of gain clarity on the type of business you want to build, especially if we start thinking about like how this extends into your life.

In the good and calm times versus trying to figure this out when your house is already on fire, right? Would you say the same is true, right? Or has been true? I mean, even if it's now in hindsight, and it's maybe a bit of a self fulfilling prophecy for you, but do you agree with that sentiment? Like, is that the value of doing that kind of work that you described there up front versus just letting it evolve over time?

Geoff Roberts: 100%. And I think whenever I talk about all this stuff publicly, people push back on specific ideas and, you know, Oh, I wouldn't pay everyone the same or I wouldn't issue equity that way. Or I don't like this component of what you're doing. And my response is always the [00:16:00] same. It's I don't want you to replicate that.

I don't care if that's the thing that you think is the best approach or not. There's so much value in just putting these stakes in the ground and saying, um, This is what we believe. This is how we operate. This is what we value. Whatever those things are, because it gives people a mechanism to select in or select out.
And I know for a fact, there's tons of people that see how we work it out set up and they want to puke. They're like, that is not for us. We want something totally different than that. And then there's people that see it and they're like, this is this. Beautiful environment. That speaks to me in the way that I want to work.
Like I want to work with you on this problem because you've structured your business this way and care about these things. So whatever it is, I think there's so much value in publishing this stuff early on and letting people make those decisions for themselves.

Adii Pienaar: Totally, totally. So I wonder another little kind of coincidental common denominator that we share here is just how kind of relationships influence the businesses that we [00:17:00] went through.
You had Dimitri alongside you, right? You learned from him and worked with him and build him and then co founded Artsetto with him. Like, what is the value of having that person? Mm hmm. That's you have some history and some context with at the very start of a, of an e journey.

Geoff Roberts: I think it's huge. If you're choosing a co founder specifically to have it be somebody that you have worked with before, you know, there's so much written about how you find a co founder and their sites for co founder matching and all that kind of stuff.

I think it's very, very hard. To really know what a working relationship like that will look and feel like, unless you've spent time working with that person before, and to be fair, even with me and Dimitri, I worked with him very intimately for, for 5 years. I saw sort of his, his rise, if you will, when I started working with him, he, you know, did not have, he was not hugely successful himself by any means [00:18:00] that changed over the time that we worked together.

In our cases, there's also a dynamic too, of if you have a. Co founder that was your boss previously, is that person going to hold more weight than you do in the relationship? And what does that look like? And even today, I'm working with Dimitri. Dimitri is, he's older than me. He's 10, maybe 10 years older than me.
He is financially set. He doesn't need Outsetted to be a success the way that I do. We have these aspects that are very, very different. But I. I knew what Dimitri valued. I knew that we had a huge amount of alignment in terms of what we wanted to get out of starting this company. And those things have remained very, very true.

So I think it's actually a kind of abnormal co founding scenario in the sense that we do have very different circumstances, but those values and ideas have continued to keep us working together very much in alignment.

Adii Pienaar: I think like, and that's like, I, I, I probably think the same way [00:19:00] about a greater team as well, right?

Like if one is very, very clear about values or shared values, at least within a company and team, it's not about being homogenous, right? In fact, it's not about disregarding the uniqueness of all the individuals. We're also just saying, here's a kind of a collection of values that we share and we believe in.
And they will always be kind of our North star or North star ish in the way we make decisions. So we'll optimize for them. We're ready about them, but we don't have to be the same to do so. Right? In fact, we actually encourage diversity because. That's what makes those values even more interesting. It's like having it, you know, being pulled into various, you know, diverse perspectives and, and directions as a result of the unique individuals involved in, in the journey.

Geoff Roberts: Agreed. A hundred percent. I'm

Adii Pienaar: very curious. So I would get into a few more of the tactical things, and then I want to jump to some of the hardships or some of the kind of your non obvious, you know, kind of your challenges alongside this, because you know, all of this sounds very idealistic, I think [00:20:00] when I've chatted to, to other entrepreneurs, The notion of life profitability is I get some pushback on, well, you know, 80, that sounds really ideal, but reality is much, much harder than that.

Right. So I'm first curious, like beyond the, you're really kind of, you shared your kind of your compensation model. Everyone earns equally within, um, I'll say that everyone is a kind of owner in the business. What are some of the other unique things? That you do this, maybe not kind of your financially orientated or kind of ownership, whether it's, you know, salary profit kind of equity, is there anything else that you can have add to the mix to really double down on the individuals in the team that you think is different to, to other teams and companies?

Geoff Roberts: Yeah. The first thing I just want to respond to is the pushback that you've gotten of people saying, Oh, that sounds idealistic. And when people have said that to me in the past, I've said exactly, shouldn't it be idealistic? Like if we're going to spend 40 plus hours a week working on whatever project or company, [00:21:00] don't you want it to be something that has an idealistic component to it?
Um, I would, I would hope so. I think the people that work at Outsetta are. Attracted to that idealistic nature, to an extent, because there are things that feel idealistic to them. And I think a reality is when you start working in this way and part of what we're getting at and with the equity component is we expect our team to help us bring this to life and make this idealism sort of blossom and come true.
It's not handed to you on a silver platter outside. So that has all of the. Challenges of any other business. And then just an example, before I, I get to the non compensation stuff, everyone sees in our model, a full time salary outside us, 210, 000 a year. And they immediately say, Oh, that's idealistic. Like you have a successful business.

You can afford to pay people that level of salary. Not everybody does. That's not, that's not true. Everybody [00:22:00] outside of does not make 210, 000 per year today. That is the full time salary for people that work full time for cash compensation. But we started using this model long ago. And we stepped into it.
So as we made more money as a business, we were able to start paying somebody one day a week and then two days a week and then three days a week. So a lot of times people just react and have this negative reaction to sort of the idealism. There's often a practical way to sort of grow into it, which is very much what our model was designed to do in terms of just kind of other things.

I would say that have been paramount in our case. 2 things come to mind. 1 is just we really want you to view your personal life is more important than our business. And again, that sounds idealistic, but the mindset is if there's something that you want to do because it's important to you. You can just go do it.
You don't need to come to us. You don't need to ask for [00:23:00] permission. You don't like we expect you to prioritize that. That is the most important thing. But the flip side of that is we expect that you'll still work hard for the company and contribute and do good work and all those, all those sorts of things.
And the example I give people all the time is, Let's say you have a musician on your team and they have the ability to, to perform at some great venue that they've always wanted to. And it conflicts with a work meeting. Are you not going to let that person go have that opportunity because there's an important work meeting?

That would be absolutely ridiculous. And that person would end up resenting you, the employer for not allowing that. And I just think that mindset is, is twisted. It's like, if you give them the freedom to go do this, they shouldn't even have to ask. This is the. Thing that lights a fire up in them. And when people look at an employer who thinks that way, they become more loyal to that employer and they want to work harder for that employer.

So I think it's just that [00:24:00] mindset. There's not really like a magic practice at Outsetta, but in our operating agreement, it says like, your life is more important than our business. And then I think the line under it is something akin to we value flexibility, but honor our commitments to each other. So it's like, we want to give you all the flexibility in the world, but yes, there's still a business here.
And we still expect you to participate and in good faith. Show up as often as you can. And we do things like we have one team meeting a week. We really try to get everybody to that meeting that we can, because it is the one commitment. But just small things in practice like that, the other one would be, we're really trying to empower autonomous decision making.

And this comes back to we're hiring senior people. We don't have any hierarchy. So there's no boss assigning you work. There's no person. Approving budgetary expenditures, those sorts of things. So in order to empower ton of decision making, everybody [00:25:00] needs all of the information, frankly. So our company is 100 percent transparent with everything.

You can log in and see our bank account if you want all, all that kind of stuff. So there's just things like that in terms of. If you want to operate this way, these conditions need to be true. And those two things come to mind.

Adii Pienaar: Have there ever been any abuse or misuse of all of those opportunities, I would say, due to the fact that it's very open, it's very flexible, it's very kind of individual centric, or have you?
Managed to avoid that.

Geoff Roberts: Yeah, we, we avoid that by a, we're a small team and, and B we, we hire slowly. So pretty much everybody that joins the team we've worked with in some capacity prior in a contract gig or a past relationship or something like that. So everybody that joins the team is something of a known commodity.
The other thing I would say is just in a. Environment like this, there's nowhere to hide. [00:26:00] We're a small team that is trying to do big things. And that means everybody needs to kind of punch a little bit above their weight. And if you're not, it's very apparent to everybody. And there's nothing that says we can, you know, fire somebody just like you can in any other business.
But we've been really fortunate to not have anybody abuse the structure really at all to date.

Adii Pienaar: What I really resonate with there, Jeff, as like you earlier, you mentioned this idea of like being idealistic and giving team members ownership. It means you're somewhat kind of inviting and making them responsible.

For making this idealism manifest, right? One of the components involved in that idealism is some of the hardship that you mentioned. I think you've mentioned that Outsider hasn't always been a rocket ship or ever been a rocket ship, right? There's definitely been financial stresses, et cetera, right? To, to what extent do you find that this kind of, this open, transparent kind of your sharing model, almost elicits that?
[00:27:00] That kind of involvement of those individuals to then also operate like owners, right? Like, do you think that they stress about the business in those times as much as you do?

Geoff Roberts: In general, co founders of any business will always care sort of at an extra level over anybody else, regardless of equity structure.

I think there's just something inherent in, I started this thing. This thing was my vision. And I was there on day one that there's always. Some degree of greater depth of feeling of ownership towards the thing. I think what we're trying to do with the model is dramatically shrink that. And I think one of the challenges with sort of that idealism and the realities of, of running a business is you could create a scenario where an employee comes in and they see this rosy picture that we're working towards.

And then if the business doesn't perform, it's not as rosy as they may be expected. And how do they sort of bridge that gap [00:28:00] or rectify that and what we're trying to do with the ownership. And I do think it is effective is saying, yes, these are the realities of our business. This is this rosy picture that we're working towards or the way that we want to operate the business, not doing as good as you want it to.
We expect you to be part of the solution. We expect you to get us through this and help us grow faster and fix our issues or fix our bugs or whatever it is. And I think there's an aspect of a lot of people think they want to play startup and then they're confronted with the opportunity of, they have to play startup and it's not exactly what they think.

And we need to be very, Clear with people when we bring them on board again, it goes back to the transparency. This is where we're at as a business. These are our challenges today. I am sort of the, uh, Anti salesman. That's always been my, my selling approach. There's somebody right now that we're trying to recruit to the team and he knows all the [00:29:00] rosy stuff and how we operate and all of that, but I've spent most of my time basically showing him the warts in the business and saying, do you still want to come into this, this environment, this scenario, and I think that's really.
Paramount, and you need to build that level of trust to operate this way.
Adii Pienaar: Tony. So we've chatted about the team there and you said co founders in a business maybe feels at least somewhat differently. So I want to shift to at least some of the, you know, some of your personal experiences and building outside on how that.

How Alceta, as a unit, as a collective, as a company, as a business, kind of your influences or touches on that. And I want to read a line that you shared in some of your writing where you say, There were and still are times where Alceta has made me a lot closer to miserable than happy. Tell me more about that.

Geoff Roberts: Yeah, I'll give you, um, an extreme example and then I'll give you just kind of the, the day to day. So the extreme example is [00:30:00] outside. It was basically started January 1st, 2017. So three years into building the company. The first two years we basically spent building an MVP. The third year we struggled to sell that MVP mightily.

So three years in, we were sitting at close to zero. We had some MRR, but it was not substantial in any way. And at that time, my wife and I were trying to have a kid. We were planning to have one. We found out we were having twin boys. And then three months later, a pandemic started and my wife lost her primary source of income.

At that time I was consulting as my primary source of income. I also lost that. So we were sitting on a mortgage, two newborns, basically no, no income and a startup we'd put three years of effort into and had nothing to show for it. Um, You better believe there was a point of reckoning and a lot of soul searching on my end in particular about do we continue to [00:31:00] go on with this?
And frankly, there wasn't a very compelling argument to make. Like, the responsible thing would have been to say, I've got these two little kids at home, I need to Go get a nine to five job and benefits and whatnot. That was not the decision that I made. I stuck it out. And at this point, I'm very happy that I decided to make that decision, but I can't tell you it was a good decision.
It was made out of stubbornness more than anything else. I sort of couldn't stomach the fact that I'd put three years of effort into something and didn't have much to show for it. And COVID did kind of give us the kick in the butt too. A lot of people started. Digital businesses at that point in time.
And that was one of the things that kind of kicked the company's initial growth into gear. So it all worked out, but at that time, yeah, work was not fun and was a huge source of stress. Even today, there are. Things that still make me miserable to an extent, one of them is we are a mission critical software product.
Our own [00:32:00] business and all of our customers businesses run completely on our product. And that just comes with a enormous amount of responsibility in terms of things like uptime and all that kind of stuff. You know, if outside it goes down. Thousands of businesses go down with it. So that is stressful. I'm luckily the non technical founder.

So I feel all of that, but I'm not the person tasked with bringing systems up if they do go down and that kind of thing. But even beyond that, we are a very engineering focused team. Uh, we had to be, to build something of this size. So. We have four engineers, a designer, and then myself on our team today.
And that basically means I'm the utility, bad analogy for South Africa. And I was going to say the utility infielder, which is a baseball term, but I'm the Swiss army knife. I do everything business oriented at our company. And. There's only one of me. So I sort of constantly feel overextended. We all do support at the [00:33:00] company, but I try to shoulder as much of the support as I possibly can so that our engineers can keep pushing the product forward.

So the reality is co founder title might, might sound glamorous, but I've been like a glorified customer support agent for the last five years. In addition to all the other things I have to do and marketing and team building and all of that. And just the way that we want to operate to your point, it sounds very idealistic, but when you're trying to build a big company in the context of a purposely small team, there's less people to distribute the work between, like we do all have to punch above our weight and there's just not people to hand the work off to.

So it has been harder to take vacations and get away and all those sorts of things. It's much better now at six than it was initially at three. It's part of the reason I'm, I would love to even get to eight or ten employees just because you can distribute all the responsibilities a little [00:34:00] bit more and everyone can have a little bit more breathing room as we get there.

Adii Pienaar: So given that status quo, right, and the challenges that are present, either kind of you still You know, in this kind of ongoing basis, or in such a cute kind of your manner, like three years into the business, don't yet have frog market fits, don't yet have revenue, et cetera. How do you think about life profitability relative to those challenges?

Right? Because you're still picking to take on the challenges because you could walk away, right? I mean, anytime you could say like, I'm done with this and I'll, I'll just walk away, but you're not doing that. So how are you thinking about life profitability relative to also having those challenges?

Geoff Roberts: Yeah, this was where your book was exactly what I needed, just sort of forcing me to reflect on exactly this question in greater depth.

There's a few things that have really anchored me and helped me choose deliberately to take some of the downsides that continue to be here to work on this business. The big [00:35:00] one far and away is just for me. Freedom of my time and my schedule and all that kind of stuff. I'm the first one to tell you, I, in some ways don't have total freedom because I answer to customers now as opposed to a boss or whatnot.
But the best version of my life, I am in control of my time and when I work and when I don't, and when I take time off and all that kind of stuff. And even in the lean times, that has always been true. And I'm one of these people that I sort of feel like I'm unemployable to an extent at this point, just because I've gotten so accustomed to that, that has probably been the single most guiding, most North star for me.
There's definitely an aspect of financial upside. I recognize I could go out and, you know, get a nine to five job that pays me double what I'm paying myself. Tomorrow, and there's an opportunity cost in not doing that, but I also [00:36:00] recognize I have the financial upside that comes with the amount of equity that I own an outsider.

And that's appealing to me. I'm pretty good at delaying gratification. I've been doing that for a while now, but that's a big component to it. And the other 1, and I would say, really, the 1 that. Kept me working through the really hard times was feeling like I have the right co founders. I tell people all the time, I actually don't think Outsetta is a great idea for a business.

There's a lot of challenges in the particular business that we're building. And the second blog posts we ever wrote on our blog, it's called my reservations with our startup idea. I was right on a lot of them in many ways, not a great idea for a SAS product, but I knew we had the team, right? In the sense that we had complimentary skills.

We were aligned as we've talked about, and that has proven very true. So I, I think it's like the co founding team. The financial upside and the freedom are all things I aspire to, or that I think we sort of [00:37:00] got right that have made some of that, that pain worth it.

Adii Pienaar: You spoke very eloquently and you added some, some new perspective and language to, you know, to my thinking as well.

Earlier, Jeff, when you said that, you know, this pursuit is supposed to be idealistic, right? And I think like in hearing you describe, um, how you think about, Like life from stability alongside the current challenges, like there is again, that there are these other things, right? Whether it's connection to kind of your people, whether it's pursuing this very idealistic, ambitious, what kind of your goal, like those things could also be part of how one describes life profitability, right?

You know, which then mitigates against some of those hardships. You mentioned the, Delayed gratification there. And I want to kind of, before getting into some rough fire questions here, you know, something you've spoken and written about quite a bit is around just kind of lifestyle design, right. And how to think about a full lifetime ultimately.

And I, I have a specific quote for you where you say, I've really lived the life so [00:38:00] much richer than 99 percent of people I know. I see so many people working towards a retirement where they want to do things I've already done. When was the first time that you made the decision to not defer? Otherwise kind of post retirement activities to that stage in life.
And instead try and incorporate them in this new stage and season of life.

Geoff Roberts: Yeah, I think in my early twenties, when I first started working at, at Bildium, I mentioned, I already had this idea of moving across the country in mind and whatnot, but I did what most people at that stage in life do. And I sort of threw myself into my career a bit and that was appropriate and probably the right thing to do at that stage in my life.

But I think after three, four years in the workplace, something that sort of dawned on Your youth is precious. Like your, your twenties and your thirties, you know, you, you have so much youth and so much vigor and so [00:39:00] much ability to go do what you want because you probably have fewer responsibilities than you will have later in life.

And I think I recognize that at a pretty early age and I'm not sitting here telling you, like, I think everyone should take their twenties and their thirties off and work later into life. I don't think that's necessarily true either. But I started saying to myself, you know, I see so many people, particularly in my parents generation, who worked their butts off for 40 or 50 years to have the, you know, traditional retirement and finally go do these things that they wanted to do.

And they sort of sacrificed the, the prime of their life in order to, to get there. And while there's some nobility in that, that did not appeal to me. I said, like, if I want to go to Paris, let's go. In six months or next month or whenever I can save up the money to afford to do it. And I definitely adopted that mindset very [00:40:00] early on and just started saying, like, what are the things that are most important to me to do in my life?
And how can I make them happen now? Just one final bit. I think what so many people get wrong too, is there's this. Assumption that in order to do those things, you need tons of money and tons of resources and all of that. I think you can make a great version of your life come to fruition much earlier and much more modestly than you might expect.

If you're willing to make sacrifices in other areas of your life. You know, I don't drive fancy cars. You know, I've never personally been one that has a lot of material possessions. And That's enabled me to do some of these things, whatever that looks like. I want to encourage more people to start living with life profitability earlier, rather than just saying, I'm going to obsessively work.
And then that comes at a later stage.

Adii Pienaar: Just to add to that, Jeff, [00:41:00] in my own journey, what I realized was I became. Very fearful for not doing some of those things that I really wanted to do in life. And then something happens to me and my lifespan is shorter than I expected or plan for. Right. Which means that unexpectedly, like I keel over tomorrow and I never did those things.
And that, like, that thought was kind of scary. Right. I don't, unfortunately control that where I do control is the thing that I do this week. Right. Or maybe next month. Right. I'm not proposing like, it's not all YOLO. I don't think that's how life works. But. I should also not defer this for 20, 30, 40 years, all right, and wait until that point in time to do some of these things that are coming at the top of my list.

Geoff Roberts: Carpe diem, you only go around once. It's super unfortunate that the people that change how they live fall in one of two camps. They have some massive financial windfall, and then they're able to do so, or they have some near death experience that makes them rethink everything. It's like, if we see [00:42:00] all these examples of both, and they come to the same conclusion.
Why are we forcing ourselves to go down one of those two paths in order to reach that conclusion ourselves? I know you sometimes need to make your own mistakes to learn your own lessons, but this one seems to me like One worth not messing around with

Adii Pienaar: totally. So talking about retirement, at least Jeff, one of the things you mentioned earlier as well, like you've got 10 or so more years of, you know, I'll say the left, and then you'll probably do something else.

And you mentioned you might write, you'll spend time with the kids and family. And then you said. You open up an Island restaurant and you'll cook meals for 12 people at a time, twice a week. I'm very curious, like what is the first meal you cook for your first 12 guests?

Geoff Roberts: Yeah. So that, that's an idea that's always appealed to me.
I like to cook. It's sort of been a hobby of mine. I'm not like the professionally trained cook or anything like that, but I like to eat. I like to cook. I'm obsessed with a particular Island in Greece where I've [00:43:00] spent a lot of time over the last few years. And there are these little tavernas, like right on the beach where you sit with your feet in the sands and the, the food is just amazing.
I love Greek food, but the vision is if I do have a financial success at Outsetta, I would love to spend more time on this island specifically, you know, if I don't need to work full time, I certainly don't want to, you know, open a restaurant and be working seven nights a week and all the stresses that come with it.
But I like this idea of. Two nights a week. It's like a preset menu and there's 10 or 12 guests and I cook for them all. And everyone sits around and chats to me. That would be a really nice version of retirement in some form where I still feel like I'm contributing and productive and doing something that I'm passionate about that isn't building a tech startup.

Adii Pienaar: Sounds incredible. Having me to Greece, like. I concur about the food, so I look forward to, to hopefully share your meal. [00:44:00] One of the other things Jeff that you chat about at least in terms of building out your own life profitability is the fact that for about kind of six months, every two years, your family is nomadic and traveling around.
What's the best tip you have for anyone that kind of wants to. Be somewhat nomadic and still get some work done, right? I mean, you also explained that the team is small and you're the generalist and those responsibilities don't go away whilst you're being nomadic. So like, how do you hack that together?

Geoff Roberts: You have to have some flexibility and it depends a lot on the time zone that you're in. So my experiences with that have looked quite different in terms of. Sort of tactically when I'm working and whatnot, I'll give you two examples. I spent three months in Hawaii, which is, you know, out in the middle of the Pacific and frankly, the, like the least convenient time zone anywhere.

But what that meant at the time that I was there, my kids were very little and they were waking up every morning at 5 a. m. anyways. So I [00:45:00] got up at about 5 a. m., you know, which overlapped pretty well with the workday. Here in the rest of the United States. Um, and I worked like 5 AM until one or two in the afternoon, and then I was done for the day.

Um, and you know, you have to kind of adjust to opening your eyes and like immediately sitting down at the computer with a cup of coffee, you know, you're Dealing with a upset customer, who's it's the afternoon for them. And they've been up frustrated with your software all day and a good morning to you.
But it comes with the benefit of you're done at one or two every day. And I take the kids off my wife's hands. She was largely watching them at that point in time. I'd give her the afternoon to go out for a run or do the things that she wanted to do. And we had the whole evening to enjoy together. So.
That was fine. I've spent most of my time traveling in generally Europe and that has been great. I love the European time zone. So we went to Greece 18 months ago and [00:46:00] Basically, I would similarly get up at a more reasonable time now. My kids are older so they're not up at 5 a. m But I would get up I would work.

Seven to 11 say I would basically take the whole day off after that, like 11 to five, 11 to six, I would be hanging out at the beach, swimming, having fun with my family, and then the kids would go to bed and I worked for three or four hours after they went to bed. So it was kind of a day bookended by work, but I got the benefit of really like taking the whole day off to enjoy myself back to your question about sort of that.
What is the juice worth the squeeze? And I, I said, uh, freedom is what I'm after. The, the freedom to sort of have that flexibility with my schedule is, is certainly something that's important to me.

Adii Pienaar: Yeah, perhaps the question that we'll ask all guests, right? Because much of life profitability comes, I think happens on a daily basis and happens in the routine stuff.[00:47:00]
So that quickly takes us to like, what is a, what is a perfect life or perfect life, perfect day in the life of Jeff kind of look like?

Geoff Roberts: Yeah. See, I, this is, this is only credit all, I don't have the, uh, huge entrepreneurial success yet to give myself credit for, but the one thing I would give myself credit for is I think I've.
Managed to optimize and have a lot of those days and abnormal amount of those days. And. Sort of back to our previous comment about you, you being a seeker. I'm a, I'm a little bit of a seeker too. It's not that I'm not happy in my, my day today, but I almost chase this idea of how good can my days be to an extent.
And my perfect day is on this little Island in Greece. We sort of keep going back there. It's been our favorite place that we found. And it's similar to what I just mentioned. So we get up relatively early, we stay in a little place overlooking the water. It's very beautiful. It's a little city of like 200 people.
So there's almost no one home. [00:48:00] I have coffee on the porch with my wife. She kind of takes the kids after that, while I get in three or four hours of work, head down to the beach. Splash around, swim around all day, have a few late afternoon beers, we eat dinner in this little taverna, bring the kids home, you know, we're all kind of sunburned and covered in salt and sands, take a shower, the kids go to bed, and.
I do a few more, more hours of work thereafter. That cadence, that lifestyle is very appealing to me. And I've been lucky to get a pretty good dose of that in my life so far.

Adii Pienaar: That's, that's awesome and inspirational. Thanks for sharing Jeff.

Geoff Roberts: And that's a wrap on episode two going forward. We're going to be bringing in guests to tell us more about their own version of life, profitability, and their own entrepreneurial paths.
But this week I want to leave by encouraging you to start thinking about life profitability sooner. You don't have to wait until [00:49:00] later in life to do the things that you want to do with your life. So my question for you is simple. What stories are you telling yourself that are holding you back? What's keeping you from doing the things that you want to do with your life now?

See you next time.