Start it Up!

Written by Joshua Steely on May 1-2, 2026

This is a post about naive creativity: I now know why my ideas never won any of STARTedUP's competitions. I'm writing this directly following the 2026 STARTedUP Regional finals, which I attended all 7 of, "[clocking] 1,500 miles" according to Kevin Schamel, their Director of Programming who thanked me and Mariah Wright for our dedication to the bit (because for me it was partially a bit, proving that sure, why wouldn't I go to all 7? I've got nothing better to do. *shrug*). At the last two events, I even got to sit, like a fly on the wall, in the judges room during their deliberation. So now I know where I went wrong… or blissfully right.

Naivette

When someone is naive, they don't know any better. It's a state of blissful ignorance that once passed is longed for but never regained. I had it when I pitched "cardboard.com" in 2022 and The Crate of Curious Things in the years following. 

Naivette partially disappointed judges twofold: first, it meant the business idea wasn't practically considered, often in terms of financial feasibility (we'll get to that); but second, because they had forgotten what it was like. At least one of the judges commented something along the lines of "man, I miss it," thinking about the hope in the students' eyes as the student said confidently "if I make an amazing product, the money will come!" That comment gave the student points for charisma, but lost them any chance of advancing to the next round. 

"He's Going Places"

Those points for charisma are valuable. They elicit comments from the judges like "that guy is the right guy, but that's just the wrong business," and "that kid is extremely hirable," and other raving praises, but again, praise of character doesn't win you an advance to the next round of an elite business pitch competition. Charisma alone doesn't win, but it does make the judges love you. It's like your favorite teacher that sucks at teaching: they're an amazing human being, but you don't actually learn what you're supposed to in their class; you would hang out with them, but not hire them to tutor your kids. 

I'm confident that I got every single point possible for charisma. I've made the judges and audience laugh, I was extremely rehearsed, I showed that I cared about my ideas, and I smiled. I had a genuinely wholesome and welcoming stage presence, and handled questions eloquently. But the business part just wasn't there. The biggest part I lacked was financial feasibility.

Money as a Mindset

If only your income reflected your optimism or ambition, so many kids would be rich, and I would be one of them. Finances are hard for many young adults to grasp, not to mention the teens competing in STARTedUP (Kerry Ao, a STARTedUP alumni is trying to fix that with his financial literacy education business, Intertwined, but I was too early for it to make it to my school). I am no exception. Money has seemed to be fake, for lack of a better word, until more recently. My parents have always been extremely generous with their funding for my ideas, and I catered my wants to affordability. But businesspeople don't clip coupons. They push the price up until people won't buy it, not down until they can't produce it. Supply and demand is their golden rule, not generosity. That makes me sad. That makes innocence look like idiocy. That makes a 16 year old's suit look like a metaphorical garbage bag of stupidity.

If I want to go into business, then I have to be willing to charge people for my product or service. I can't just "do it for free" and spend my life savings on materials to improve their experience. If my money runs out, I can't do much. Sure, I can say I hate how money controls people all I want, but that doesn't mean it will let me go. I need to make money.

In high school, that's not exactly the case. The highschoolers are alright to be thinking "I can hand-sew all 300 sweatshirts and charge 80 bucks each" because their parents are paying for the roof over their head and the food in their bellies. It makes sense that they are naive in regards to money. But that can't last in the world of business.

The STARTedUP pitch competition is the first step for a lot of kids (in Indiana) to realize the realities of entrepreneurship. I'm grateful for all that I've learned through participating in and attending pitches over the years, and hope to continue to be involved in the growing network for a very long time. As Don said at each competition, he hopes to know us for the next 20 years, (which would make him 74 and me 39) and I agree with the sentiment, though not with the likely graying and balding that comes with it. What will I do in those 20 years? Perhaps finally start my own official business.

Revisiting the Crate

Once again, I have motivation to revisit The Crate of Curious Things. This time with a deadline and a goal. The deadline is four months: May through August, 2026 (yes, that started yesterday). And the goal is to teach workshops at 30 Retirement Communities and 10 Corporate Offices.

To do so, I've taken steps in finally forming "The Crate of Curious Things LLC," creating a Google Workspace account with Bookings pages, retaining the domain "crateofcuriousthings.org" and learning more about invoicing and taxes. I've also brainstormed the following two initiatives to fit each of my target markets for this summer:

The Lemonade Stand

This is the one I'm really excited about attempting. It's professional development for corporate offices using "lemonade stand" based challenges and scenarios. By using upcycled materials like manilla folders, scrapped printer paper, and cardboard boxes, employees will undergo a series of interpersonal communication challenges designed to test their teamwork and management skills. I am SO excited to see grown men in suits try to bargain with crayons or balance marbles–things they may do with their kids but never their coworkers. The workshops will, of course, maintain the five core principles of the Crate: Collaboration, Recreation, Artistic, Thrifting, and Experience. The environment will just be extremely different from a public library or a church. I'm excited to see which companies bite.

Project Orange 

This is what Don Wettrick has been pestering me about trying: programming with Retirement Homes and Communities. "Project Orange" gets its name from the orange hue of pill bottles, which will function as the foundation of several upcycling-based projects with the retirees. I will be in the Indianapolis area for the four months mentioned above, so I will have access to nearly 200 retirement homes/communities (according to Don) and hope to host workshops at at least 30 of those. It'll be a challenge! but I have a great support network with experience in retirement community programming (eg. the NMPL Staff) that will help me find my groove faster than I could find it alone.

To avoid naivette, I'm learning more about invoicing, taxes, forming an official LLC, and charging clients appropriately for my time and efforts. I've set a challenging, but realistic goal, and have constructed a plan to achieve it. I look forward to succeeding,

since now I'm (hopefully) not naive enough to fail.