Taylor Nieman: Flying high with Toucan

Issue 09

Hi friends! Welcome to Procrastineur, a newsletter about founder’s struggles and successes.

Welcome to the 1 new subscriber who joined us since last Thursday! Join 33 procrastineurs by subscribing here:

It’s Thursday, June 24, 2021, and this week’s founder is Taylor Nieman.

Taylor’s Story


Taylor Nieman, entrepreneur. With over 85,000 active users on her product, Toucan, it’s hard to imagine a time when she wasn’t sure how to build, or raise, or bring an idea to market.

All entrepreneurs have to start somewhere, though. Taylor began at Cornell University, earning a degree in Business and Communication in 2010. From there, she operated in business development for a few different companies, all while trying to get her first ideas off the ground.

Along the way, Taylor would quit her job to focus on the project she was building at the time. 

Those jobs she quit? They were high-profile roles in companies such as Headspace, where she was an early employee. She saw them through their Series A and Series B funding rounds. She also worked at Science, which spawned Dollar Shave Club and other successful companies, Pop Inc., a successful app creator, and Fair.com as they went through their $385 million Series B raise.

Taylor learned a ton from these companies. They were exciting to work at and help grow. But they weren’t hers.

Her first three tries

Taylor’s first company was a talent and recruiting company that she started during college. It was built to help her friends, but didn’t make it after graduation.

Second was an app called Simba. Taylor’s dog, Simba, was very good at making friends at the dog park. Unfortunately, dog owners don’t always feel comfortable sharing their information just to set up playdates for their animals. She worked to fix that by enabling people to mark their locations so others could join (or avoid) them and their furry friends. Simba lasted a few years, but ultimately puttered out.

The third attempt was Lancer, meant to be Glassdoor (a salary + benefits sharing website) for freelancers. Shedding light on the marketplace would benefit so many people. Unfortunately, that information is very hard to come by. People don’t always want to share what they earn, even anonymously. On top of that, she and her cofounder Brandon - now a cofounder at Toucan - pitched over 200 investors, all of whom shot holes in the idea.

Taylor learned, as so many founders do, that the right idea is hard to find.


After her time with Fair, Taylor again left to create something of her own. This time though, she had an idea that would stick.

The biggest proof of concept is always going to be the customer, and Taylor had one who really sticks out. Ryan Hudson, who built Honey, the world’s greatest money-saving browser extension, was a mentor to her for years. Toucan was the first idea Taylor had that he was willing to go all-in on. As a king in the browser extension space, this was a fantastic green light for her.

Taylor started Toucan in July 2019 with two co-founders, Shaun and Brandon, which she met at Headspace and Fair. The team has now grown to 16, with plenty of room to continue. 

Toucan has rolled out support to learn 11 languages as a native English speaker, including German, Spanish, Chinese and Arabic. They also support learning English as a native Spanish speaker. 

With $4.5 million raised so far, Taylor, Shaun, and Brandon are off and flying. In January, they were nominated as Product of the Year on ProductHunt. Before long, we’ll all be singing their praises in more languages than we can count.

You might even say they’ve had soaring success. Go anywhere with Toucan.

Taylor’s Advice

  • Start as soon as possible. Terms of service don’t have to be perfect, your landing page isn’t the key part of the project, etc. 

  • It’s never going to be perfect. Get it in front of people early - they’ll let you know if it’s good

  • Ask strangers to review. Friends and family are often too kind

  • Gather data on how your projects are improving

  • Don’t look at competitors! The moment you start looking at competitors you stop listening to your users.

You can connect with Taylor on Twitter as @Taylor_Nieman or on LinkedIn. Find her cofounders on Twitter as @ShaunMerritt_ and @BrandonDietz_.


Procrastineur” is a newsletter about modern founders’ successes and struggles, written by Will Whittenton. You can connect with me through my website, Twitter, LinkedIn, or send me an email at willwhittenton@gmail.com. If you enjoy the newsletter, please share!

Want to show your undying devotion to this newsletter? Buy Me a ☕!