Gutsy Lessons from Humble Investor Karen Howland

March 16, 2022

(highlights from Episode #2 of the Gutsiest Brands podcast)

Karen Howland’s mom might have no idea what she does, but Karen breaks it down for us in our latest Gutsy Brands podcast. From how to ignore naysayers to the benefits of having irrational expectations, Karen gives us all her best advice. 

Karen is the Managing Director of CircleUp Growth Partners, an equity venture business within CircleUp that spots high-potential brands before they make it big. She sat down with our Chief Revenue Officer, Jess Gaedeke to discuss the importance of data, how amazing brands come from anywhere and anyone, and why empathy is the key to being a gutsy brand. 

Takeaway #1 Data Is Key

The revolutionary Helio technology used by CircleUp is designed to seek out millions of consumer brands and distill them down to the top brands which are innovating faster and better than others. “Data is certainly a big piece of it,” Karen agrees. “If you take a data driven approach and you take a category like cosmetics for people of color, you can actually do a deep dive into the category and see where people are excelling as far as distribution, social engagement, and price positioning. And you can put the map together and then look at it and say ‘okay, this [brand] is extraordinary. 

Takeaway #2 Amazing Brands Come from Anyone and Anywhere

Karen points out that women and people of color are vastly underrepresented in venture capital investments. Although it was not their direct intent, the visionary technology of Helio allowed CircleUp in their very first fund to support 50% female founders and 30% people of color. Karen says the idea is “going out and really trying to shake up the category and shake up private marketing and trying to find amazing investments regardless of where the company is located.” 

Takeaway #3 Empathy for Understanding

Empathy to me is understanding your consumer. It’s really getting what people need and what they want,” Karen says. To illustrate this, Karen brings up the brand Yeti. Yeti came onto the scene trying to create premium outdoor products, something the investment world would have laughed at. But by understanding their niche market and what their customers wanted, they were able to build a loyal brand following that spread and are now a $7B market cap company. Jess (a Yeti user herself) agrees, saying, “it just feels like they really did their research to understand the true experience people wanted to have with their product.” That is the power of empathy.

Takeaway #4 – Have Irrational Expectations 

“[In] the context of irrational expectations, I think founders have to have that to be successful,” Karen tells us. But what exactly does that mean? “You have to have those expectations that [you will] persevere. Have these irrational expectations that ‘I know this is going to work.’” She rightfully points out that gutsy brands are those which disrupt their category, giving the example of The Flex Company who, under the pioneering leadership of Lauren Wang (an upcoming guest on the Gutsiest Brands podcast!), have taken on the behemoths in the period products category with a highly innovative offering and are seeing incredible growth, encountering obstacles at every stage but being willing to plough through them. However, she also warns not to stick too rigidly to your ideas. “You’ve got to make tweaks along the way as you learn and as you continue to improve,” she says. 

Karen’s Best Advice?

“Don’t listen to the naysayers,” Karen says immediately when asked what is the one thing that can make a brand gutsy. If it was easy, it would’ve been done before. People will tell you it can’t be done. People [might] say, no, this doesn’t make sense. I’m sure every great innovator and great entrepreneur heard that fifty times before they ultimately had success. 

Keep Learning 

To catch Karen’s full interview with Jess, along with fascinating conversations with other entrepreneurially minded leaders, head over to our Gutsiest Brands podcast.   

Written By



Want to stay up to date latest GutCheck blog posts?

Follow us on

Check Out Our Most Recent Blog Posts