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February 6, 2020

7 Startup CEOs and Founders Share Their Biggest Surprises

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Founders don’t build a startup because they crave routine and job security. They understand their path will be carved out from every decision made along the way, and will often involve challenging twists and turns they couldn’t have anticipated. 

To help future founders get a birds-eye-view of just what those twists and turns can look like, we asked seven founders to share some of the biggest surprises they’ve had on the job as they’ve built their company. Here’s what they shared.

Every Day is An Adventure

“The most surprising thing is that every day is an adventure,” says Amy Errett, CEO and Founder, Madison Reed. “The things that you thought a month ago were the hardest things that you’re ever going to tackle…three days later there’s something harder. Even in the midst of that hard stuff, I get totally energized every day by my job in spite of the hard curveballs that get thrown at you. Many of them aren’t fair but it doesn’t matter, that’s just the way it goes.”

The Importance of Determination 

“The advice I would give to an entrepreneur who is just starting out is that determination is vital,” says Philip Krim, CEO and Co-Founder, Casper. “With any startup, the odds are what you want to create doesn’t exist yet.”

“By definition, that means you’re charting a new course and creating your own path. Often times, there are difficulties along that journey. To get through those challenges, you need to have determination and conviction that what you want to create needs to and must exist. It’s a crucial ingredient to long term success.”

The Power of Community

“The thing that’s most surprising to me is just how amazing our community is,” says Stu Landesberg, Founder and CEO, Grove Collaborative. “Grove speaks to people from every state in the country, from rural to urban, from young to old, who really want to make better decisions about the products that they’re buying for their families, their pets, their friends, their roommates, and also for the planet.”

“I think the depth of connection that we’re able to make with our community because of our mission and because of the incredible people that are out there, continues to surprise, amaze me, and delight me every day.”

It Takes a Village

“I think everything has been somewhat surprising,—you’re creating something out of nothing every day,” says Bianca Gates, CEO and Co-Founder, Birdies.”Every day there are surprises, but I would say the biggest surprise on this journey for me has been raising money. As female founders, we’ve heard stories of women trying to raise money from venture capitalists. And in my mind, I had this impression of venture capitalists not understanding what we’re trying to do.”

“We really extended the life of our initial investment of $100,000 as long as humanly possible so that we could avoid raising money,” says Gates. “But it turns out, once we really felt ready to raise money, it has just been the biggest surprise and delight of this journey. The family at Norwest has been an incredible team of people who have not only invested capital in us but a tremendous amount of resources. They are lifting us up as we build this company, and almost creating a road map for us that has been incredibly helpful as we have grown in the last few months of this partnership, and in the last couple of years since raising money.”

“I would even expand that more broadly,” says Marisa Sharkey, President and Co-Founder, Birdies. “I absolutely agree with Bianca, but even beyond that, just the number of people that I’ve met and had interactions with over the course of my life who have been helpful in building Birdies has really surprised me. Of course, I find that it’s useful to ask very specifically for the help you’re looking for, but people have come out of the woodwork to really support us both and really support the building of our brand.”

“People that I worked with ten years ago, or that I went to school with—people are really inspired that we’re doing something new, and they want to help,” says Sharkey. “I’ve just been surprised and really delighted to see that. And it’s been so fun to collaborate with other people, and see their unique ideas.”

It’s as Satisfying as it is Hard

“The biggest surprise for me, one, just how hard it’s been,” says Jennifer Fitzgerald, CEO and Founder, Policygenius. “The advice I give to other founders is, ‘However hard you think it is, it’s probably a hundred times harder.’ Everything is harder when you don’t have a brand, when every day counts, because you are not yet profitable or a big household name.”

“Everything from recruiting talent to attracting customers—it’s just that much harder,” says Fitzgerald. “You’ve got, basically, one hand tied behind your back when you are a new, emerging company that not a lot of people have yet heard of. Just how hard it has been a very humbling experience. On the surprisingly positive side is just how great it feels when things actually work and you’re able to get really great people working for you, and you’re able to deliver on a promise to customers. It’s easy to get lost in the weeds and not think about that, but it is deeply satisfying.”

Finding Mission-Driven Partners in Surprising Places

“A lot of the developers we partner with are really just looking to build more housing,” says Brad Hargreaves, CEO and Founder, Common. “They’re looking to create more and better places where people live. Common works with them to help make sure that they are building the right way: that they’re using smart design, that they’re utilizing technology to make their products more affordable, and that it’s accessible to a wide number of Americans.”

“Really understanding the needs of the real estate owners and developers we work with on a day-to-day basis, understanding the challenges they’re facing, has been one of our biggest surprises,” says Hargreaves. “They are almost always aligned with Common in creating a high quality, affordable housing product.”

What’s been your biggest surprise as a founder and CEO? Let us know on Twitter @NorwestVP