Want to Get Into Product Management? Start a Company

How running your own tech company can help you bridge any skill deficiencies you might have in product management.

I am often asked for advice on how to “get into” product management or how to “get better” at product management. I always feel like such a fraud when people ask me questions like this because I don’t think I ever “got into” product management. Instead, product management was the culmination of progression from customer obsession to product development to entrepreneurship.

You can trace this all the way back to high school when I started working at a grocery store in Tucson, Arizona. At a grocery store, the product isn’t the items on the shelf. The product is the service that you get and the experience you have while navigating the store. The product is the design of the end caps on each aisle, the level of engagement you have with each customer, the stock levels of various items in the store. The product is the number of shopping carts available at the front entrance and the number of cashiers available when it’s time to check out. The product is the way the groceries are packed into bags for each shopper and the offer to take those groceries out to the car.

I don’t know if I would have followed the same path had I worked at a large chain grocery store. As it so happened, I started work in high school at a store that was part of an Arizona-local, family-owned chain called Bashas’. Perhaps because it was not a large chain, perhaps because it was family-owned, and perhaps because it was exclusive to Arizona, the way these stores conducted business was different. They were the Amazon of grocery stores. Customer obsessed.

I carried this customer obsession into future jobs. I worked in auto insurance, which is a decidedly unfriendly place for customers. And yet, I found ways to focus on the customer experience. I found ways to make people feel important. This obsession with customers and their experience allowed me to make the leap from call center to tech. I joined the Geico.com team in Washington, DC building our customer journey maps, helping with user experience interviews, and working along side the engineering team to constantly improve the online experience.

It was during this time that I started my first (real) company. I had started businesses before, but those had been the pipe dreams of a high school kid who didn’t know what he was doing. Now, though, now I was an adult who didn’t know what he was doing. Which meant it was an official company.

The business was simple. Write about sports, build an audience, place ads, and get paid. But even here, I was focused on the product. I was focused on the experience—and what is the product if not the experience? Reading articles, especially in the sports world, with intrusive pre-roll video ads, pop ups, and more was annoying. So, I designed a layout that would better accommodate ads while allowing for a clean reading experience. This cost the company in extra ad revenue, but it helped make the site sticky with readers. They spent a lot of time on the site and they kept coming back. Even more important, they shared it with their friends.

But it wasn’t perfect. My perfect world was a world where there would not be any ads on the site and people would pay for access. But I was too early. That world did not yet exist and people didn’t pay for content online, save for a few newspapers that had transferred their physical business model to the digital world wholesale. When it became clear that I could not improve the product any further while maintaining a revenue stream, I decided it was time to move on. I entered into negotiations with a fantasy sports company, and that company eventually bought the site.

This led me further down the rabbit hole of tech. I joined a startup in Dallas building EdTech software for colleges to accept digital media portfolios. This was a small, bootstrapped company, so I got a chance to do…everything. I did product demos, ran QA tests, worked on the product backlog, spoke with customers, did customer support, and maintained the sales process. By the end, I even started coding. The bar for high-quality products was suddenly lifted even higher for me. This company was started by an art student turned art professor who had an eye for design. The experience of using the software was unlike anything I’d seen in EdTech.

My time there laid the groundwork for me starting my next two companies. It was at these next two startups where I developed the customer interview chops. Talk to people, get on phone calls, meet them in person. I learned that coding was the last thing I should be doing. I learned that market research was one thing, but customer research was a whole other thing. I learned all this through trial and error. I learned by failing. I made mistakes that I could only make as the founder of a startup. And these mistakes led to improvement. They led to a stronger sense of how to build products. It led to the intangibles that can often be so frustratingly hard to define.

After shutting down my last company, I came into my current role at Pinata. I was the first employee and helped shape the company’s product direction. As we raised a seed round and started hiring, I led product. As we hired more, I led a product team. After we raised our Series A, I became VP of Product. And through each step, I was able to learn while also applying past lessons from my work as a founder.

So, when people ask me for advice about how to get into product, I feel like an impostor. No, you don’t have to start a company to get into product management, but I’ll tell you what. It makes it a whole hell of a lot easier. I encourage people early in their careers to consider starting a company if they have an idea and have the means to support themselves while trying it. I believe that you can learn product management skills through a variety of different avenues, but to me, the fastest way to pick up the skills necessary to be a strong product leader is to throw yourself into the fire and manage the product you started.