What I Learned from Building a Company with a High School Student

Jeff Osborn
The Gimkit Blog
Published in
8 min readJun 20, 2019

My boss just graduated from high school! 🤯

I’m somehow simultaneously in awe of and super proud of my boss and co-founder, Josh.

It was amazing to be included in everything surrounding Josh’s graduation, especially meeting his extended family and getting to know his parents and siblings better. But my favorite part was sitting there during his graduation ceremony thinking about what an awesome person he is and how much of his journey is still ahead of him.

Graduation day!

It sounds a little outlandish that a high school student created a successful, rapidly growing learning tool used by millions while he was still in school. But if you know Josh, it isn’t outlandish at all. If you know Josh, you know this is just the beginning. Although what he’s done with Gimkit is incredible, it’s small compared to what I know he’s capable of.

Now that I’ve had a week to think on the whole experience and reflect on our time building Gimkit together, I have a few notes I’d like to share on working for and with a high school student:

Genius

When I tell other adults about the creator of Gimkit they always ask the same thing: “So, is he a genius or something?”

I really don’t know what I’m supposed to say to that. At first, I didn’t have a good answer. I’m not even sure if my current response is that great. For now, I say, “I don’t know many 18 year-olds, but he’s pretty remarkable.”

Josh doesn’t like it when I call him things like “remarkable” but the fact that I’m explaining a truly sensational product with an incredible growth arc and all they want to talk about is Josh, makes him, by definition, remarkable.

Here’s the thing: So so many of our young people are remarkable. Like, SO many.

I’d argue that each young person is remarkable, in their own way, but we simply don’t remark on them.

Maybe it’s because they haven’t yet found “their thing” the way Josh has. Or maybe we can’t see their genius for some other reason. Whatever the case, we should find more time to discover the amazing attributes each young person possesses and take the time to remark on them.

At Josh’s graduation, his advisors (his school’s word for “teachers”) talked about each student in his graduating class. Each one was remarkable in some way and the adults that had worked so closely with them took the time to make sure each was celebrated appropriately.

One young man had developed a class about flight at The Museum Of Flight here in Seattle for school-age kids. Another created his own cryptocurrency (two, actually) and had them listed on a few exchanges. Yet another did humanitarian work in another country. The list went on.

One thing I love about the high school Josh attended was how they approach their students. It’s a Project Based Learning school, which provides outstanding opportunities for personal learning and growth, but only if the students feel challenged. One difficult task for advisors is to treat their students totally as individuals while challenging them to do big, incredible things. They don’t let the students get away with letting themselves down.

Importantly, they don’t compare Josh and his classmates to each other. Rather, they help each student compare their present self to their past self. The standard of learning is what it should be for each of us regardless of age: tangible personal growth.

Too often we set the bar far too low for young people. Given the opportunity and support, every young person can be as remarkable as Josh seems. He’s brilliant and incredibly focused and a terrific problem solver. But so much of what he is has come as a result of the external support he’s received and the space he’s been given to be himself. Josh would still be remarkable without that support, but we probably wouldn’t be able to see it.

Each of us is a genius on some level. My experience working with Josh on Gimkit has reinforced this idea and strengthened my resolve to support others, especially young people, in finding their genius, whatever it may be.

Expectations

I entered into my relationship with Josh in the mindset of me as the teacher/mentor and Josh as the student. It wasn’t so much of an age thing — I’ve honestly never really thought much about his age in terms of our work together — as much as it was an expertise/experience thing.

When Josh posted Gimkit (then called Gimlet, which is a whole other post 😃) on Product Hunt I reached out with hopes of helping him refine his vision and product. I loved the concept of Gimkit and saw ways I could use my experience to help.

In my intro email I offered to help with growth, the name issue, and with anything else he might need. At the time I was consulting full-time and I made sure to explicitly offer to help for free. I really wanted to be involved and help any way I could.

When Josh responded and we met up for the first time I remember being super excited because I’d been getting increasingly interested in and passionate about education. I felt useful and super optimistic about my long-term goal of getting my career shifted all the way over into the Education arena. It was really great to be able to help a high school student work on an amazing product.

I expected to mentor, advise, and teach Josh as he built Gimkit. And I did that, to be sure. But something else happened as well. Josh became a hugely transformative presence in my life, professional and otherwise.

Josh has a gifted product mind. He inherently and effortlessly sees solutions where others don’t. He is more than a lightning-fast learner. In addition to being bright, he always wants to learn and, as a result, asks brilliant questions in all situations.

All of the above were clear to me after the first few times speaking with Josh. But in the year and a half plus that I’ve known him, I’ve noticed something else: Josh is one of the most humble and empathetic people I’ve ever met. He has, without trying, taught me more than I ever could’ve hoped to teach him about being a kind, thoughtful person.

Because of Josh I’ve become a better gift giver, a more thoughtful listener, a more persuasive debater (he’s stubborn in a good way!), a more effective and productive worker, more confident in myself, and a better communicator.

One of the best lessons I’ve gotten from Josh so far is to check my expectations of him and anyone (or anything) else at the door. I entered into our working relationship and friendship expecting that I would be the one giving Josh the gift of my experience and passing my knowledge on to him. I’m happy to say that I feel like he’s taught me more in 18+ months than I ever could’ve expected.

We can only grow if we keep our hearts and minds open. The first step toward that openness is silencing expectations. Being open to learning and accepting improvement from anywhere, regardless of their age or anything else, is not always easy but it’s essential.

Empathy

One of the most surprising things about Josh is the effortless way he solves other people’s problems.

My first week working with Josh after joining him to work on Gimkit full-time late January 2018, he identified and solved a problem I didn’t even know I had. And in the five months since then, I’ve seen him do it over and over for me and for others.

One thing I work on really hard is being empathetic. It’s something I want to get better at and something I want to model for my children. I never thought the person who would teach me the most about empathy would be almost half my age, but life is full of surprises.

Watching Josh care so deeply about teachers he hasn’t met who live 3,000 miles away has been incredible. If one person has a bad time on Gimkit and it could’ve been prevented, Josh feels bad about it. If a single student struggles with an element of the game, Josh immediately starts thinking about how he can ease that student’s pain.

Being near someone with such a big heart and selfless drive to create has been life-changing. Truly. I treat my family differently. I treat strangers differently. I answer questions from Gimkit educators and students differently. I look at people I pass as I walk to work differently.

There have been many amazing things about working with Josh on Gimkit, but seeing how Josh solves problems in such a meaningful, human way has been eye-opening in a way that’s hard to explain.

Humility

Thanks to Josh, I’ve gotten a taste of what real humility looks like.

I wouldn’t begrudge Josh if he developed a little swagger. He just graduated high school and already he’s hiring his 2nd, 3rd, and 4th employees. He’s making an impact in Education at a time when his own K-12 journey is just wrapping up.

Despite having reasons to be cocky and over-confident, Josh remains one of the most humble people I’ve ever met. The reason this is worth noting is that this trait, maybe even more than any of the others I’ve mentioned, is why I think he’ll be successful. His ability to do something amazing, soak it in, and go on to the next amazing thing, is, well, amazing.

The Journey

This ride would be a wild one with any co-founder, but I’m so glad I’m on it with Josh.

He’s a goofy nerd, just like me. He prefers shorts instead of pants, just like me. He isn’t a dad, but, like me, he has a proclivity for dad jokes. He also talks with his hands almost as much as I do, which is no easy feat.

We get along well, but we also make up for each other’s shortcomings nicely. Areas that I’m weak in, he’s strong in, and vice versa.

Josh is a kind, caring, focused business partner in a way that feels rare. He can be direct and effective without being curt or rude. He can levy criticism and disappointment without hurting my feelings. And he’s always open to receiving criticism and to having his mind changed.

Even though it feels like we’ve accomplished a lot, we have a long way to go with Gimkit. A really long way. The thought of the road ahead would be terrifying if I was embarking on it with anyone other than Josh.

For me, the journey with Josh has been working on Gimkit, but I still have no idea what it was like to be doing the job of at least two people to keep Gimkit going last winter while going to school and holding an internship at FiftyThree. I have no idea what it’s like to have people call me a genius when I’m still trying to be a kid or to have to watch my friends go off to college while I’m hiring adults and building a business. I can’t imagine the range of emotions.

But I can say this: If it ended tomorrow, it would still be one of the most incredible, rewarding, transformative experiences of my life. If you’ve never done it before, I highly recommend working for or closely with someone younger than you.

You never know what you might learn or where you might go.

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