Trent Anderson: Meandering his way to Marketing

Issue 05

Welcome to “Procrastineur”, a newsletter about struggles and successes in modern entrepreneurship.

It’s Thursday, May 27, 2021, and this week’s founder is Trent Anderson:

  • Baseball’s saving grace

  • He’s a Law School drop-out

  • Shocker! He’s a procrastinator too

  • Prewrite’s Story

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Saved by Division III Baseball

Trent wasn't always a marketer. In fact, he wasn't even always headed in the “right direction”, as each of our parents hope for us. No, he took a more leisurely route immediately following high school.

Trent happily recalls “partying with the best of the Big 10”, an athletic conference at the highest level of American collegiate athletics. His coursework at Indiana University took a back seat for those 6 months of glory, but of course Trent came around, if only because his parents weren't going to pay for him to fail out of school.

Trent transferred to North Central College in Chicago for the spring semester and was able to walk on to the baseball team, where his greater journey began. Trent's penchant for procrastinating was tempered by 4:30am practices, followed by a day full of school and a 5pm practice after that. There was no longer any wiggle room in the schedule. He had to figure out how to be a student athlete, with all the pressures and commitment that came with it.

A Winding Road

Trent went to Law School after earning his undergraduate degree.

Unfortunately, he hated it.

What Trent didn't hate, though, was building out alumni marketing programs. He developed relationships with previous graduates and brought so many back to campus. Everything was great!

Except Trent didn't study enough.

Luckily, Trent was able to pivot into a better career path. He enrolled into the Notre Dame MBA program.

Following that, Trent got a job in TV ad sales, but he quickly realized that the field wasn't growing any more.

So he started interviewing. Trent wanted to showcase and grow his marketing skill set, and interview after interview led to the same result: everyone kept pointing him to the same guy, a small business owner building out his own firm.

Trent got the job.

Procrastinating his own journey

Over the next six years, he helped grow the company from $200,000 to $8 million in annual revenue.

Then he got married. He had his first son. Trent was doing great!

He had an “itch”, though – Trent wanted to start his own business.

Just before he was going to get started, Trent got an offer to work in a different agency. He accepted and did that for about 6 months, but soon realized he was just delaying the dream of working on his own projects.

Trent joined up with a friend of his and founded Leadlio. You'll enjoy his video announcement: Trent's New Startup - Introducing leadlio - YouTube

They learned, as all entrepreneurs do, on the fly. Trent and his buddy built up the company's recurring revenue and were doing very well. In fact, Leadlio is still doing well.

Trent wanted to try his hand at software though, so he took an opportunity to go work at Prewrite. They have had their struggles, as expected, but he's loving the journey.

Prewrite's Story

Story is pervasive. Prewrite exists to help people tell those stories.

It started out as a software designed for screenwriters, by a screenwriter. He wanted to build a product that helped writers structure their scripts well.

The problem came when they were searching for funding. Globally, there are only about 6 million screenwriters. Venture Capitalists need to see potential to make a 100x return on their investment, and that market just isn't large enough. What's a startup to do?

Trent realized that the opportunity to tell stories exists everywhere. YouTubers, Podcasters, and other creators are constantly putting together information for their audiences. Prewrite could help them do it better, faster, and more consistently.

All they had to do is build it.

And build it they have. Prewrite has software for screenwriters, marketers, and creators, with more on the way. Check it out at (you can write your first project for free).

Prewrite has grown by utilizing a social media strategy. They used TweetDeck ( connect with writers and have grown now to over 5,000 users.

Trent has one piece of advice for builders and creators though: connect with an audience first! When you know them, you can build for them and with them. It's a lot easier than the Field of Dreams method. “If you build it, they will come” isn't always true.

You can find Trent on Twitter as @TrentAnders0n.


Procrastineur” is a newsletter about new business, modern founders, and other entrepreneur-adjacent topics, written by Will Whittenton. You can connect with me through my website, Twitter, LinkedIn, or send me an email at If you enjoy the newsletter, I’d really appreciate it if you would share or forward it to others.