The Messiness of Entrepreneurship: Creating the Right Company and Understanding Your Value Proposition

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Entrepreneurship doesn’t happen in a straight line; there can be several instances where a founder needs to shift strategy in order to move to plan B (or plan C). Entrepreneurship is messy, and successful founders need to be both patient and flexible along the way.

During the Keynote Presentation at the Project Entrepreneur Summit: Chicago in 2017, Lori Feinsilver, Head of Community Affairs and Corporate Responsibility at UBS, interviewed Carley Roney, Co-Founder of The Knot/XO Group, about the pivotal moments in her entrepreneurship journey and how the ‘messiness’ of founding a business helped her find her value proposition and improve her pitch.

Being an entrepreneur is a “thrilling ride,” but also excruciatingly terrifying. For Carley Roney, “the ups and downs of the first 24 months of being an entrepreneur were an exhilarating time. I look back, and I kinda get hives.” But for entrepreneurs who are able to push through the downs and pivot when necessary, there are opportunities for gratifying success.

The Messiness Behind Creating the Right Company:

Roney’s first company was a digital production agency she started with her husband after graduating from film school. “After the disaster of running a digital production company for two years and looking at the prospect of having to do sales and marketing to get more projects, [I realized] this is not sustainable,” says Roney. She had to tell herself, “This is not a good business. You’ll never make any money [with this model], you’re always in a panic.”

Roney sat down with two of her former production clients, acquaintances from film school, and her husband, and began sketching out the initial plan for an internet-based business: the four eventually become co-founders of what would become The Knot/XO Group. In fact, one of Roney’s male co-workers suggested looking at the wedding industry, and the team moved ahead from there. For Roney, going it alone as an entrepreneur was not an option: “I really need someone to bounce things off of.  I think better with another person. The four of us [co-founders] work together really well.” Roney suggests bringing on a co-founder to help you sort through the messiness of entrepreneurship is key: “Make sure that your jobs are absolutely distinct.  What you don’t want when looking at teams is that these people are [all] the same person. You want people who are your complement, who challenge you, and who are different from you, and the four of us are different people [with] incredibly different skillsets. It was one of our secrets to success.”

The Messiness Behind Understanding Your Value Proposition: 

Roney learned something very valuable about her company’s actual value proposition the first time she pitched The Knot to a potential investor. Her first pitch deck had about 20 pages dedicated to telling the story of The Knot’s brand. “We were all storytellers. We all went to film school, my friend worked in an ad agency.” The story wasn’t going over well with the investor. “We were dying out there, [and] this was our only pitch.” After hearing from the investor that their business model was the worst he’d ever seen, Roney’s co-worker pitched a new idea in the middle of that meeting, proving the true value of the business and securing funding. “We had the story all wrong,” admits Roney. From that meeting, the team learned to lead with their true value: that The Knot was the best company for connecting the 2 million brides that get married each year (responsible for a $72 billion wedding industry) to the vendors that want to do business with those brides. “It became a totally different pitch.”


Learn more from Carley Roney on episode 45 of our podcast, #theTools, “The Messiness of Entrepreneurship.” and be sure to subscribe on iTunesGoogle Play or SoundCloud.