What I Wish I’d Told My 18-Year-Old “CEO” Self

Over a decade ago, I started my first company. And so in today’s article, I want to share with you what I wish I had told my 18-year old “CEO” self at that time. These are just some general entrepreneurial lessons that hopefully another person can find potentially useful in the case where you’re younger and you’re thinking about potentially becoming an entrepreneur.

The inspiration for this article is that one of my helpers for my company today is a 16 year old, who has been sort of a mentee of mine and I’ve really enjoyed working with him because it’s given me an opportunity to share some lessons that I wish I’d somebody else had told me when I was around that age as well.

Lesson #1: Title means nothing

So the first thing I tell my 18 year old CEO self is that really, that title means nothing at that point in time. I think that part of the reason why I started a company at that point in time was just because I felt like you need to do something in the world. That I needed to change the world in some sort of way.

And really, it didn’t really matter at the end of the day. Like ultimately, I was way too young at that time to really understand what the title of being a CEO meant. And I think we’re in this sort of cultural time period where everybody’s kind of a CEO, you see every single week on shark tank, some sort of seven year old, that’s the CEO of their business.

And it really is creating this sort of impression that you have to do something really fast and really young. And that’s something that I wish that I had been told earlier on, which is just that you don’t have to go change the world when you are 18 years old or younger.

Oftentimes, at that point in time, what you can do though, is you can just learn the ins and outs of how to run a business. But at that time, I think that I tried to take on this sort of title without even really fully understanding what it meant to be a CEO. What does it mean to operate an effective business? What is required in terms of making your team happy in terms of creating documentation that’s effective, or even just creating a value or service that other people are willing to pay money for?

At that point in time, I was just too young to understand that, and I think it only came from working with other entrepreneurs that were older than me, or later on in their journeys that I started to understand those sorts of inner working.

Lesson #2: Your first product is not likely to be your lasts nothing

The second thing I would tell my 18 year CEO itself at that time is that ultimately your first product is not likely to be your last. At that point in time, it was my entire life for about a year and a half or so when I started my first company. All of my waking hours are spent trying to build this thing from the ground. And we achieved some sort of form of success in which we did go viral for the thing that we did. Now, that being said, at the end of the day, everything kind of comes and goes, especially when you’re in that sort of phase.

It is typically going to be rare to find something that you are willing to stick with, from the time in which you are in either early high school or early college, all the way through your adult life. It just doesn’t typically happen statistically.

In many situations, you’re going to run from different projects to other projects, and so what I wish I had told myself at that time is it’s obviously important for you to take things seriously since you want to be successful in this thing that you’re building at the same time, don’t take yourself all that seriously, too. It’s good to get some foundational experience. But from there, what you can do is you can use that experience to then go to your next opportunity.

And then from there, you can think of to yourself, how you can transfer some of the learning experiences you had from the early experience into the new opportunity that you might have in front of you.

At that particular point in time in my life, I wish I had been a little bit more diversified in terms of the different interests that I had in place. I spent all my time obsessing about building this thing up. And I was with my co-founder at that time, but I didn’t feel like he was really doing as much of the heavy lifting as I was. And so it just led me to not really be all that happy about running my own company, which was kind of the whole shtick in the first place as to why I wanted to do that was because I wanted to feel that freedom of owning my own sort of business.

Lesson #3: You really don’t know what you don’t know

The third thing I wish I had told myself back then is that you really don’t know what you don’t know. And what I mean by that is oftentimes you can spend a ton of time coming up with some sort of offer or service to sell, but until you actually get in front of potential customers and talk to prospects about the sort of pain points that they’re facing, you don’t actually know how they want to be sold.

And the best way I can explain this is at that point in time with my company, we were selling these sorts of credit packages that people could use for our professional services that we were offering. And nobody was really buying them. And it wasn’t until I started actually talking to my prospects at that time that I actually learned that the reason why they didn’t want those sorts of credits was because it was confusing and they didn’t really know exactly how these sort of credits could be used for our services.

So instead I just repackaged the offer a few different times. And from there settled on a set number of hours of services and things like that. And it became much easier to sell our services. So the other thing that I tell myself at that time is don’t be afraid to test different offers, especially when you’re in the early stages of building, whatever it is that you’re trying to sell. The reason why is because if you don’t test what’s resonating with your prospects and what isn’t, then you’re just going to get stuck in a dead-end.

And that’s something I think where me and my co-founder wasted a couple of months at that time, trying to make that model work, as opposed to just getting in front of more prospects and pitching this model and getting that sort of feedback earlier on.

Lesson #4: It’s not at the end of the world to go work for somebody else

The fourth thing that I wish I told my younger self, when it comes to entrepreneurship here is that it’s not at the end of the world to go work for somebody else either. I think at that point in time, I’d gone through a summer in which I was reading all these different entrepreneurial books. I was reading, Delivering Happiness by Tony Hsieh. I was reading all these different $100 startup books and things like that, where that were very inspiring. But at that point in time as well, I didn’t have all that much business experience.

I had run a tutoring business and some web design businesses in high school, but none of them were super serious. And so the benefit of working for somebody else that is a little bit further along than you. At that point in time in your life is that you get to learn, what’s working and what’s not working for them.

And it’s from observing other people that are in later stages of the game than you that you’re then able to pick up on how you can potentially cut some corners as you yourself, start to play that section of the game. So what I mean by that is don’t compare where you are today with another person that is 10 or 20 years older than you and that’s been an entrepreneur for a while because they’ve seen way more worst stories than you have in terms of just life experiences.

And so I think that’s something I would’ve told myself at that point in time is go work for another entrepreneur that’s actually a little bit further along than where you are, just so you can understand what they’re thinking about in terms of how they’re facing the challenges of their business.

That’s actually something that I ended up doing a couple of years into my college experience in which I spent one summer actually working for a startup that was a couple million into their revenue journey. And it allowed me to get an inside look in terms of the sorts of business challenges that the co-founders of that business were facing and how they were tackling it.

Lesson #5: Maximize your learning experiences

The fifth thing that I tell my 18 year old self is to really maximize your learning experiences at that point in time in your entrepreneurial journey. It’s really easy to get caught up into the idea of wanting to make a lot of money. In fact, you know, I went through all my life without an allowance, and so I always wanted to find a way to make money.

That being said, though, what you have to understand is that it’s more important for you to understand how exactly can you create new value in the world or additive value in the world than just respinning something out. That’s something that actually came up in a conversation with that 16 year old that’s been working with me in which he has some friends that have been making some decent money, doing some sort of black hat stuff in terms of SEO.

And what I had to tell them is that ultimately your friends might be able to do that for a little while. But at the end of the day, they’re not really creating true value in the world. They’re not creating something that’s adding incremental value to somebody else’s life. And as a result, you know, while they might be able to do that for some time, ultimately the algorithm is going to catch up to them.

It just inevitably happens in which if you’re just to think about a 16 year old and their friends, yes, you might be an absolute genius in the world, but to think that your friends are actually going to be smarter than the entire engineering team at Google who are actively working on figuring out malicious activities like that is just something that is unlikely in terms of outcomes for your friends to win at.

And so this is something I had to kind of reframe him on and something I had to help him understand is that there’s always going to be a shortcut. Regardless of what you’re doing in life, there’s always going to be a shortcut that’s presented to you at a certain point in time. And the important thing for you to understand is that you have to make a choice as to whether or not that’s actually a meaningful shortcut that is legitimate, or it’s something in which you actually have to go on a much longer journey to get the experience that you need and really understand something at a bigger level.

And so in this particular situation, you know, this was something that I had to experience myself, but I went through that same stage too, in which when I was a teenager, I was actively on those get paid to sites where you’d complete surveys for a couple of bucks and things like that. But after a while of spending hours completing these surveys, what you realize is that you only get a dollar or two for submitting those surveys and that the actual winner in that situation is the person that created the survey site that is working with all the advertisers to line up the right demographics with the surveys that they are posting on their site.

That is where value creation is. And so if I were to tell my 18 year old self something else, I’d say, learn how to create value and learn that to take the journey to and appreciate the journey for what it is.

At the end of the day, I went through most of my early high school and college days broke. I had a couple of hundred dollars in my bank account, but it was through just experimenting and maximizing for learning opportunities and appreciating the journey along the way that I started to see more successes on all the different side projects and actual jobs that I ended up taking.

So that’s something that I definitely recommend, which is don’t be afraid to just take a step back and reflect on the journeys that you’ve taken and the learnings that you’ve had along the way. Oftentimes, the journey that it took to get you somewhere is so much more valuable than the actual outcomes that you experience.

If you want a great book recommendation for that checkout, Paolo Coelho, The Alchemist to read more about that.

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