A.J. Lawrence:
Thank you so much for coming on the show. I really appreciate having you here today.

Tyson Koska:
Very happy to be here.

A.J. Lawrence:
As an entrepreneur, I’ve had issues with my own finances left, right and center. And yes, the whole goal of doing this is to make money and, you know, to create the things we want. But I’ve seen so often in conversations with other entrepreneurs that our finances are usually really messed up to keep it, like, until we keep saying some imaginary point down the road will clean and make everything up. So, I mean, a tool like this, I think is really very cool. I was reading that you kind of started this because you couldn’t find the software you wanted for your own planning, you know, and then you went, and now you’ve been doing this. I also know you’re a professor and you do a lot of other very interesting things. Where do you see yourself on your own entrepreneurial journey these days?

Tyson Koska:
These days I’m at the point where, and I think any entrepreneur that’s grown a company of any particular size knows this problem. I’m at the point where I’m trying to make myself replaceable, where I can’t be the one to make every decision or know every nuance of the business. So I’m at that point where I’m literally as difficult as it is, you know, handing things off and giving things people to do and empowering them to make their own decisions. And the hardest thing is not questioning their decisions, going, okay, let’s just see how this all comes out. So I’m really at the point where I’m not trying to make myself more important. I’m trying to make myself as unimportant as possible in a lot of ways.

A.J. Lawrence:
Okay, so do you see yourself working more? You know that lovely phrase, was it, don’t work in the business, work on the business.

Tyson Koska:
I would say that’s definitely where I’m headed. Not quite there yet. I’m still very much in a lot of things, but businesses aren’t going to hit the kind of growth that we all sort of dream of as entrepreneurs unless the CEO does just what you said.

A.J. Lawrence:
I find it very often, having bounced many times off this kind of ceiling. You can do a lot of things if you’re smart and very energetic. Once you get that kind of initial luck spark, something happening, and then all of a sudden you find you get to this situation where you’re like, wow, this is a business, it’s working. But I can’t just force of will it anymore. I need to add things to it. So as you’re kind of looking at this, are there things you would like to, you would like your own efforts? You know, you said working more on it, but as an entrepreneur, are there things you see yourself, you know, working more on as you go into this transition?

Tyson Koska:
Again, this is a natural outgrowth that I’m sure every entrepreneur has felt. You have to stop engineering so much and start marketing more and start being the face. And you have to go out and do podcasts.

A.J. Lawrence:
You have to talk, right?

Tyson Koska:
You’ve got to like yeah, you’ve got to talk to people. You’ve got to. Because so much of it is people. It’s networking. I mean, we all know this. The relationships you make are absolutely key and foundational to any successful business.

A.J. Lawrence:
Really is. And especially when, like I said, I think software is so cool. Yes, for other people than entrepreneurs, but definitely for that. And being able to find ways to reach audiences and to communicate in a way that you’re not just, let’s buy this keyword, let’s put this ad up. It’s like, yes, you have to do that, but at the end of the day, this gets you deeper into that realm.

Tyson Koska:
Honestly, for us, what you just mentioned is almost not even an option because we’re competing with Fidelity and Vanguard and big tool makers that are in the personal finance space. It’s a very expensive space for a startup to be in. And you just have to do things differently. You can’t buy keywords. They cost way too much.

A.J. Lawrence:
Okay. If you’re going to bring it up, going to dive into a little bit. If you have to do things a little differently, what are some of the things you feel that you’re kind of doing to position yourselves against these fun competitors? We’ll leave it.

Tyson Koska:
I think fun is a great word to bring into the conversation. So in my opinion, I know we haven’t talked a lot about what the tool actually does, but in vague terms, it’s a personal finance tool. It helps you create not a budget, but it helps you create a 50 year plan into your financial future. And it answers some really interesting questions. Well, stuff that traditionally only financial planners did for their customers. And there has been, of course, “retirement calculators” and that sort of software. But those things exist to get you to pick up the phone and call the brokerage because they scare you. They’re like, oh, you need this number to retire or else you’re screwed. And the fact of the matter is that that’s not true. And you can create a path that doesn’t necessarily follow a straight line. But so many tools out there are straight line tools. You know, that’s sort of what we’re doing. So we’re approaching the market from what do people really need? What do human beings, regular consumers, you know, even entrepreneurs are regular people. And we’re not all financial planners, we’re not all accountants. And so we’re approaching the problem from if a regular person needed to be able to solve a 50 year plan problem, what is the way to make it actually a doable. But. And I’m bringing that fun word back in, making it a kind of fun thing to do, like make it like it’s not sitting down and entering how much I spend on gas last month. This is not doing, you’re not, you’re not going to do that in my tool. And in fact, if you made me do it, I would walk away. I would never use it. I mean, because, because it’s just not fun. So we’ve had to, we’ve had to look at this in ways that are rewarding, are engaging, are ways that turn financial planning from I hate it so much. I’m willing to give up 1% of my portfolio per year, which is the assets under management model. Because that’s how much people hate it. They’re willing to give a lot of money on the table. Of course the financial industry hides it, right, because they’re just like, oh, you don’t pay me anything. They don’t write you a bill for $30,000. It just comes out of your gains. So how do you bring that fun into the tool and into the conversation.

A.J. Lawrence:
I think that is a huge thing because I’m in a relationship where we have different financial structures. Sadly, both of us are MBAs, but very differently, as I like to say. I did my MBA because I was offered a full ride. Well, actually I had an economics professor in undergrad who thought it’d be really hilarious if I applied for a fellowship that no one had ever applied for, pre-digital everything being online. There was a folder of all the things and was like, yeah, there’s one thing in the back of the thing that they’ve never told anyone. There’s a fellowship. So, yes, that’s why I have it.

Tyson Koska:
Oh, that’s too funny.

A.J. Lawrence:
He was like, yeah, it’d be really, really funny. And yeah, you would actually like business school. And I was like, okay.

Tyson Koska:
Well that’s great. That’s a great story.

A.J. Lawrence:
You know, except for the fact that like it was two years of not growing up instead of actually doing anything later on. The value of education has helped, but still it was two years of not growing up. But I love looking at the finances and looking at scenario planning, all that. My partner, I don’t want her getting too upset. She was very, you know, oh, I am in some private whatever. You know, elite private banking. Yeah, they call that. And it was like, I was looking, I’m like, wait, it’s 1% plus all of your funds are like huge. Yeah, it’s like, yeah, you have a lot. But guess what?

Tyson Koska:
They don’t want you to look at that.

A.J. Lawrence:
Oh, but I can talk to them anytime and they can do anything. It’s like, yeah, guess what? There’s a whole point of that. So yeah, I think that is really cool to kind of play into that and kind of incorporating that type of fun because. Yes, it is. It’s trying to get both parties in a relationship, you know, and this on board together. That would be definitely very fun.

Tyson Koska:
And I don’t, just before we move on to the next topic, I don’t want to denigrate what planners and advisors do because they’re critical. You can’t expect everyone to know everything. I just, I’m not a fan of the AUM 1% model.

A.J. Lawrence:
Yeah. I think there’s also a lot around the fee based for, you kow, when you talk about the human planning and different. It’s the fee based planner versus sort of the commission based. Lo and behold, one cost you a little bit more upfront. But then you statistically you get a better result long run. So it’s like, I wonder why. As you’ve been doing this, as you kind of creating this and you’re trying to position yourself against the larger players, what do you think has helped you the most in this process?

Tyson Koska:
I would say a little bit is that I started the company with no prior baggage. I’m not a financial, I’m a software engineer. Was a software engineer for 25 years. I never used any of the big financial tools that planners use: eMoney Advisor, MoneyGuidePro, Right Capital. I never used any of those tools. So I came at the problem from a completely novice perspective. I was like, if I wanted to make a 50 year projection, what do I need to know? Well, I need to know income streams, spouses income streams. I need to know that she’s pregnant right now, she’s going to be taking off work next year and there’s going to be a gap for two years. So how do I model a gap in? And how do I say, well, I’ve got one college savings plan now, but I’m going to need another one in three years or, you know, whenever. And I approached the problem from, well, how would a regular person go about doing it? Ironically, after put the software out there and I went and looked at how other tools are doing, I’m like, wow, that is so weird how they saw we all solved the same problem, but they solved it in a way that was rooted in history. I didn’t have that expectation. I wasn’t iterating on the way that other software approach the problem.

A.J. Lawrence:
I remember very briefly how cool Mint was. And then all of a sudden it got bought and it was like, what just happened here?

Tyson Koska:
Yeah, it was so innovative and it was so fun. And what I really know what I was wanting was a Mint that would look out 50 years instead of looking out three months or whatever it does, six months.

A.J. Lawrence:
But you know, by not kind of knowing, you knew software, you had that background, how did you- once you kind of, you know, I always say it’s like you do something to scratch your own itch. But then there comes a point where you have to kind of transition from your itch to plural. What is plural of itch? Itches, others. All right, but how was that transition for you? Like what happened to kind of help you get into that from yours to a larger pool?

Tyson Koska:
Yeah, that’s a really good question. So it was really interesting. So my two partners, the way that I got started on the business was that I literally, my wife came in and said, honey, we’re having a second child. And I was like, that’s great. And then I thought, man, we’re going to need a bigger house, we’re going to need to, I want to move out to the burbs, we’re going to need a second car. Like all these financial implications started piling up. And I thought, you know what? I’m tired of waiting for someone to build the software that I want. I’m just going to start building it on my own. And I prototyped it out. I was at the time, I was going to New York every single week. So I was spending a lot of time on the train and I built this prototype and it gave me joy to play, like to pull little switches and levers and see how the projection would change based on small decisions, which I found really fascinating. And I went to two other programmer friends of mine. I was like, guys, we got to make this software because look, look how fun this is. Like, hey, if I just bump up my 401k x amount, look, in 30 years, I see this. But it also takes into account the fact that you’re going on vacation or taking a year off or you’re doing whatever, and it mixes it all together instantly in your hands and they’re like, Oh, Ty, that’s got to exist. And I said, well, if it exists, great, go find it for me because I’ve been looking for it. And they came back and then we decided to do this thing. So your question was, at what point was it no longer my ideas or what I wanted. When did we usually have to start listening to the community? It happened pretty quickly because again, I was not a financial planner. I was not really that deep into the whole personal finance space. I just thought, well, these are really rough numbers and I want to see what these changes do over the long term. Well, it attracted a lot of people that were just really nerdy. Have you heard of the FIRE community?

A.J. Lawrence:
Yeah. FatFIRE.

Tyson Koska:
Yeah, okay. So CoastFIRE, BaristaFIRE, LeanFIRE. So these folks were like, oh, this is great, but it would be even better if you did this and did that. And I quickly, personally, I was like, this is solving my problems. I’m good. But then the community was like, oh, you got to do this, you got to do that. And I was like, you know what, maybe we do. Maybe you do need to do that. Now, of course you don’t. You don’t want to respond to every single customer request. Sometimes the requests resonate, but sometimes they just reach a critical mass where you’re like, so many people are asking for this. So part of what happened was I personally ran out of ideas. We would do an annual survey. We’re like, hey, we’re setting our roadmap up for next year. What do you guys want? And they would all vote. We’d put five or six things on the list that we knew, we thought, we wanted to do, and they could either vote on those or enter other suggestions. And then we would tally them all up and say, okay, community, here’s our list for the next year. And that was what happened. That’s how we grew.

A.J. Lawrence:
And that is so cool. And I take it you got traction in the people voting and you were able to get something that you felt coherent enough to kind of keep going off of. That is cool.

Tyson Koska:
Yes. And those folks felt really invested when they saw the thing that they were asking for actually come to be. And then we started getting stories about how the software literally changed their lives. I mean, talk about from an entrepreneurial perspective, that fills your gas tank up for weeks and weeks.

A.J. Lawrence:
I’ve done services firms throughout my history, but like, the first time you hear someone talking about you and without realizing that you’re listening and they’re saying good stuff, and it’s like, oh, my God, that’s amazing. And to hear someone talk about your software must be like, wait, they download it, they signed up, they what? They jumped through those hoops, all that amazing thing, and they did it and they’re talking positively about it. That must have been cool.

Tyson Koska:
Of course, the flip side is also true, right? You see a rude comment on the Internet and you’re like, can’t sleep for three nights. Like, how could they say that about my software?

A.J. Lawrence:
Yes, but to a certain degree, I feel like. And I don’t know yours but I know with mine, I had already thought, except for some of the really stupid negative comments that I’ve heard about, things that my team or, you know, we’ve done. But like 99 of the time, if it’s anything about the actual structure, work, whatever, I’d already like, oh, my God, this isn’t as good enough. Instead of this and that, you know, I’ve already beaten myself up because it’s like, you know, the typical entrepreneur trying to be higher, but yeah, listening to it. So now, now that you have kind of gone, that you did reference sort of a Reddit, are you still using this type of guidance in this annual sort of vote for your future. How’s the community kind of going around this now? I’m an LP in a couple of what I call baby SaaS, angel funds, and I’m an advisor to a couple. And that’s been a huge theme even on the B2B. I know you are B2C, but it’s like simplifying the onboarding and simplifying the user experience. There’s been this keeping it simple and then pulling things back for later. You increase your lifetime value. This consistent. Literally just had this conversation yesterday with a security workflow SaaS that works with huge enterprises. And it was like, yes, we gotta simplify. It is amazing how you know, that works because you want to create the features your customers ask for but too much, too little, the simpler you get as long as it’s not too simple. That is the magic you go through.

Tyson Koska:
Yeah. And no one should ever underestimate how hard it is to be simple.

A.J. Lawrence:
I always reference the Mark Twain telegram. 5,000 words easy, 500 hard. It’s like, you want a 500 word article, no, sorry. 5,000 words, can do tomorrow for you, but 500 words, yeah, no, no, not going to happen.

Tyson Koska:
I actually hadn’t heard that one. I feel that.

A.J. Lawrence:
There’s a story where his editor asked for something and he’s like, I can give you 5,000 words. 500 is too much work.

Tyson Koska:
Well, there’s a story about James Joyce that his, I don’t know if agent is the right word, but publisher or someone. And they said, you know, how did the writing go today? He’s like, I wrote eight words. And the publisher said, well, that’s really good for you. Eight words, great. And Joy said, yeah, but I don’t know what order they go in.

A.J. Lawrence:
But okay, to kind of jump back into this. How should someone who’s looking to kind of have a more enjoyable, more engaged way of thinking about their finances and planning out, how should someone, an entrepreneur coming on from the show, what’s the best way to kind of engage and what should they expect? Because I know sometimes I go in and I have to connect all my accounts and oh, my God, Citibank has some insane business thing that will never connect with anyone ever on the planet. This plaid connection doesn’t work. Oh, I have crypto. Sorry, one over. You know you can’t come talk to us. What should someone expect the flow to be like? To engage with OnTrajectory.

Tyson Koska:
So you heard me say a moment ago that we’re really happy and wanting to have people that don’t necessarily have all the maturity. So in our tool, if you want to connect an account, you can. But if you have a crypto account that has no connections, we have space for that. We have space for things that are other. So there’s always an other. And what I always tell people is, I’m sure you’ve heard this in lots of different flavors, is start broad, use broad strokes, get the big pieces down. Understand, I’ve got basically this much. And we don’t even ask you your expenses. For example, we ask you, how much income do you have? And we ask you, what have you managed to save so far? This is how you onboard. It’s really simple onboarding. A lot of these tools ask you a million questions. How much do you make? How much have you saved so far? And then instead of asking about your spending, we ask you one simple question. How much on average do you manage to save in a month? Now, people know what they make. They know about how much they have in the bank. And if they’re actually putting something away each month, they know what that number is. I’m contributing my 401k or I’m socking away. Well, guess what? Now I know your expenses because you’re spending everything else, right? So I know your expenses. I can fill that in for you. I can make some future assumptions about when you get older, how your expenses might change. We try to make it as easy as possible because we want people to see the big picture. And then when they go, oh, you know what? Now I want to add this account in because I want to break it off from the hole, and I want to concentrate on it because I want to put some employer match in there or something like that, or I want to break this income stream off because maybe I want to take off a year. And so it’s I need a gap. I need to put a gap in there. So it’s all about iterating and refining, iterating and refining. And I mean, that’s true, in my opinion, about a lot of things in life. You know, start broad and then, you know, don’t try to solve every problem upfront because you’re going to get exhausted and you’re maybe going to give up.

A.J. Lawrence:
When it comes to entrepreneurism, it’s just like, you know, utilizing deliberate practice. It’s sort of like, okay, what are you trying to do, what are the goals? And then iterate, you know, incremental progress, directionally correct. Like, okay, today was really bad, but guess what? I was able to save a penny on something.

Tyson Koska:
Yeah. And what you just said is also important. That’s that flex, that notion of flexibility, which is why I’m personally not a huge fan of budgeting apps. And some of them actually do the flexible part pretty well. But you know what? I don’t. I actually don’t want to know how much I spend eating out or how much I spend each month. I’d rather just say, all right, here. I want to stay under this umbrella. Let me figure out how to stay under that umbrella over time.

A.J. Lawrence:
That’s a good thing. As someone who’s moved from New York City to like southern Spain, I do have to say it’s like, oh, yeah, it was probably a really good thing for me. It’s amazing how much my savings increased after that move in that experience. Okay, so someone comes in, they kind of get into it. So let’s maybe jump to like your super users. Like the customers you guys think are like rocking it. When does that happen? And you know, what type of experience or what have they put in to get to that experience do you think for using OnTrajectory?

Tyson Koska:
I think it comes down to having a notion of, oh, they get me, they understand me. They understand the problems that I’m trying to solve. Just the other day, I said a moment ago, not everybody’s a CPA, but this was a CPA from California who wrote me and goes. She said, I was so thrilled to find you. I finally found software that operates like I think it as a person I think it should operate. And I think that there’s some click that happens with some people and the software. It meets expectations and I think it’s even better. What good software should do is actually meet your expectations, but also lead you someplace new into new possibilities and new ways to visualize your future. Which they’re all hard because guess what? We’re all different people. But in the end, we’re all visual creatures. So we depend a lot on that visualizing how all these numbers, how do we draw a complete picture of your life? Which once you try out the software, you’re going to realize, oh, my gosh, more than almost half of the screen is just taken up with this gigantic visualization.

A.J. Lawrence:
What I’m really enjoying is you have referenced that you came from a developer background and all this, but yet what’s nice is you haven’t really hit on it yet. It’s obvious. As someone who’s been in the business for a while, you know what you’re talking about in the development cycle, because you’re not talking about the development stuff. You’re talking about what happens after good code. It’s like, it’s kind of fun seeing that in this. What’s something you think, though, that either grit you’ve had in growing or maybe a mistake you made in kind of this growth here that you think other entrepreneurs could take a lesson from?

Tyson Koska:
I would say we’ve all heard this phrase, that an entrepreneur cannot depend on the phrase “If you build it, they will come”. We all know that that’s not true. You can build something great, but unless word gets out, unless you’ve got some way to show yourself off in the marketplace, you’re not going to have success. And I just was so obstinate. I just kept my head down. My partners and I coding, iterating, making a better product, making a better product. And we did marketing, but we did it reluctantly. We didn’t really spend money on it. We should have. We would dip our toe into it and then it wouldn’t immediately work. So we’d say, okay, it doesn’t work. We’re just going to keep adding features. And now we find ourselves, and maybe this is good, maybe this is bad, but we now find ourselves in a situation where we’re actually removing features and functions so that we can bring people on that journey. So it probably would have been a better idea to probably should have just hired someone to do the marketing and gotten out there, but we were a little bit conservative in that way. But here’s what I will say to those entrepreneurs that are out there that really have an engineering bent and really are working hard to solve a problem that either they perceive or that they have personally. For us, it worked out. It just took a little longer than it probably needed to.

A.J. Lawrence:
It’s funny because in talking with other SaaS owners, it is very much that. Especially from the product-led side, product-led founders, it is a common thing. Because as a marketer, it makes logical sense but then when you kind of take that step back, you’re like, yeah, but we use different vocabulary and we do something a little bit different. And it’s like, oh, yeah, it doesn’t make inherent sets. Product is about utilization and flow and all those, you know, really nice juicy things. While marketing is engagement, push, pull. It becomes slightly different. And it’s common thing for a lot of product-led to delay on marketing or not find that right marketing mix at first. So I’m glad you did get there.

Tyson Koska:
Again, another iterative process.

A.J. Lawrence:
Well, okay. Have you given much thought to what success will be for you as an entrepreneur compared to what success is for OnTrajectory? Like how does that differ and where do you see it going?

Tyson Koska:
I approached the problem that OnTrajectory solves and you mentioned it earlier. It was because it was a thorn in my side. I wanted, I personally wanted software to answer a particular question for me. And that question was at what date, on what date can I quit my day job and move to Malaga? Show me that date. Show me on the screen. Because once I see it on the screen, then everything else becomes kind of easier. It’s a peace of mind thing. It’s always been a peace of mind thing. I wanted to get the numbers out of my head. I wanted to get them down. I wanted to see where I was going. And once I saw that path, then when I go and I want to have a four dollar latte, I can have it. It’s not a big deal because I know, I know what’s going on. It’s that peace of mind thing. So for me, success is a continuation of that. Knowing that I don’t need to be the biggest entrepreneur. I don’t need to have headlines at all. But what I do need is peace of mind for me and my family. And as long as I’m enjoying myself, I mean, it sounds so cliche, I almost hate to say it. But as long as I’m enjoying myself and I’m solving real problems for me and for other people, that is a win. That is a huge win for me because I can’t imagine anything better than creating peace of mind in a community of people. I mean, how awesome is that?

A.J. Lawrence:
I have to say as someone who I remember struggling when I was younger and like losing sleep over money and all this stuff, anything that would facilitate the reduction of that stress of living paycheck to paycheck and understanding what this means in the long run, that is huge. That is, that’s so much benefit you’re giving back into that. I mean it’s peace of mind or at least reducing of stress is huge. Without a doubt.

Tyson Koska:
It’s interesting because even if the news is bad, even if you’re telling someone you are on a bad path, well, okay, I didn’t know that. Now I’m going to get over and I got to get right the five different phases right now. I’m going to emotionally get over the fact. But then they can start doing something about it. Because up until then, they were going to be in a worse situation until they realized something was amiss. And you can’t fix something you don’t know is broke. So, you know, even when I am the bearer of bad news, I still don’t feel that bad about it.

A.J. Lawrence:
You give people the opportunity to change their ways. That’s always a hard thing because most people, I don’t want to know. And then it’s like, oh, okay, it actually is good I knew. Other than going to OnTrajectory.com, what other ways can people come check out the software, engage with you? How should they come?

Tyson Koska:
Right. So I’m easy to engage with. I mean, my name, Tyson Koska is pretty rare. So if you look me up on LinkedIn, we can hook up immediately. If you want to email me directly, it’s ty@ontrajectory.com. If you want to try out the software, it’s ontrajectory.com. No credit card or anything, you just sign up. And we have a very active help desk. So if you’re like, I’m confused how to do this, we have a little tool inside and you can even say, hey, I want to talk to Ty. And then I’ll reach out to you that way as well. So pretty accessible guy.

A.J. Lawrence:
We’ll make sure we put this all in the show notes, in the newsletter when the episode comes out, and we’ll put it on our socials. So now, Tyson, thank you so much for coming on the show. I really, really enjoyed it and I’m looking forward to playing with this later on because I have some crazy spreadsheets that it would be nice to simplify my 20 Google Sheets trying to track everything or at least get a better direction. So thank you.

Tyson Koska:
I hope we can help you with that.

A.J. Lawrence:
This will be fun to explore.