The Pursuit of Scrappyness

We arrived at the trade show without a booth. In fact, my co-founder and I hadn’t even purchased a badge for the event. We simply showed up, attended social events, and lined up meetings at a coffee shop within the convention center. At night, we crashed on a beer-stained sectional at my buddy’s Vanderbilt apartment.

We were seniors in college with a prototype of a software product that we were hoping to get feedback on. With no revenue or funding, we kept our expenses limited to flights, Lyfts, and FedEx print-outs.

Despite our scrappiness, our attendance paid off. Connections from the convention would lead to several of our initial customers and a write-up in USA Today.

Fast forward two years and we were back at the same trade show…this time with our own booth. The creator of our backdrop had designed trade show booths for Disney. And a professional team designed the layout of our space, ordered everything we needed (from carpeting to TV monitors), and took care of the set-up and tear-down processes.

In between those two trade shows, Zcruit had been acquired by the largest company in our industry. We continued to operate as an independent entity. But with the acquisition, we now had a piggy bank (okay, more like a trust fund) that we could pull from.

My first act with our newfound resources was to spend $3,500 on zcruit.com (an upgrade from our lowly .co) from one of those ‘domains for sale’ websites. We then hired a four-person in-house tech team. We paid an agency for a full-scale product re-design. And when the graphic designer I sought out said her rate was thirty times what I was accustomed to paying on Fiverr, I didn’t bat an eye.

The investment paid off. The product improved significantly – enabling us to triple our price-point and quickly grow our customer base. After three years in the red, Zcruit became a profitable business with momentum and a solid technical moat.

But it also re-wired my entrepreneurial brain. I got really good at spending money in a manner that was detached from revenue. Instead of doing things myself or hiring for cheap, I now had experience working with world-class professionals and my quality standards increased accordingly. Doing things for cheap now felt…well…cheap in a way it never had before.

Since leaving Zcruit, I’m now working on getting new projects off the ground. And that means either continuing my previous spending patterns, this time with my own money at stake, or getting back to my scrappy roots.

But there’s something daunting about spending my own money on business expenses with unpredictable outcomes. I have a set amount of time before I run out of money, and spending on business pursuits zaps that time away. Despite viewing my post-acquisition Zcruit spending as an investment, it’s hard to know which parts really paid off. I can’t tie dollar amounts to “this one feature” or “this trade show booth” or “our .com URL”. There wasn’t a linear relationship between each expense and a financial outcome. And my acquirer knew that. They were prepared to give us the money and time to figure it out.

But I now have consequences to my spending. I can’t freely spend on things that may or may not provide financial benefit. I have to be thoughtful and strategic about every expense I make.

Yet relearning how to be scrappy is difficult. I got used to there not being trade-offs between price, ease, speed, and quality. Regardless of cost, I could choose the highest-quality, easiest, and fastest option every time.

Being scrappy means actively deciding to move slower and produce lower quality work. I might know that this designer I’ve worked with in the past would design a beautiful product – way better than anything that I could dream up. I might know that this developer could build the product way faster and better than what could be done by me or my lower cost alternatives. It’s uncomfortable to choose the scrappier option and consequently know I’m putting out substandard work.

But deep down, I know that the scrappy, substandard work is actually better for me than the high-quality yet costly alternative. Because ultimately, in a trade-off between time and quality, time wins. I can still validate my ideas through substandard work. Yet if I cut down my time by spending money on quality, well, I might just wind up with a high-quality product that people don’t need (see: Quibi). It’ll be okay to spend lavishly on great designers, engineers, or marketers when the product’s been figured out. But I’ll need to have the self-control not to spend lavishly in order TO figure it out.

When starting something new, the scrappy way is a longer road to success. Yet it’s also the best guarantor of success. So as tough as it’s going to be to break my bad habits and change my ways, I know what I need to do.

It’s time to get scrappy.