Drew Hart moved back to Wisconsin after stints at startup companies in San Francisco. Drew has since launched Milwaukee-based Snow Day Group, a web development company that works with startups. Drew is a great guy to know and we’re proud to name him as this week’s Startup Milwaukeean of the week!
At what point did you become interested in Entrepreneurship?
I first became interested in entrepreneurship during my teenage years. Although in my early years, I didn’t think of myself in terms of an “entrepreneur.” Frankly, I didn’t really know what that term meant until a few years ago. Still, I’ve always been a creative person who is able to weave together abstract ideas and create solutions.
I went straight into a corporate environment after graduating from college. I benefited greatly from that experience. It wasn’t until I had the opportunity to build a sales team from scratch that I recognized the notion of being an entrepreneur. That project was akin to building a mini startup inside of a large organization. It included building out a project plan, kneading out the business processes, marketing, training, rinsing and repeating. That experience did two things for me. First, it confirmed my skills, knowledge and experience. Second, it provided me a great degree of confidence and the notion that I could be successful working for a company that needed creative solutions regularly—so I quit!
What has been the largest difficulty you have faced as an entrepreneur?
Transitioning from a well defined work style to one that’s totally ambiguous. For example, in a corporate business, a lot of risk is removed (including product development, marketing to customers, etc.). It’s easy to plug in, since so much of the business is already defined. There’s a large number of people working in each of the respective departments who have those things covered.
With a startup, however, nothing like that exists and there aren’t departments of people to complete the tasks. You have an idea. Everything else you have to create on your own. That includes developing your product or service, outlining a marketing plan, putting business processes in place, creating contracts, finding talent and selling to customers. All of it (and there’s a lot I’m leaving out). A lot of romanticism surrounds the concept of startups—but once you decide to cut your own path, it’s yours. I love that. It gets me up in the morning and [my team] builds amazing things.
What piece of advice do you have for new startups?
Get connected with other startups and be transparent about both your failures and wins. Being open inspires others to be open. Doing that really helps; you’re sharing information that benefits everyone. Most of us don’t know what we’re doing when we kickstart things, since it’s all brand new. I’d also suggest following entrepreneurs online through blogs, twitter, LinkedIn, whatever. There are a lot of people out there who share their stories, both good and bad, and they are tremendously insightful.
What makes Milwaukee a unique place to start a company?
I wouldn’t say it’s unique. I see Milwaukee having a lot of the traits of other cities across the US and worldwide. The history and culture of Milwaukee gives the city a unique character. Just take a look at all of the independent business owners of restaurants and bars. I guess one thing that makes Milwaukee unique is the proximity of Lake Michigan and its positive impact on the weather. All said, from Bayview to Shorewood, the Milwaukee area has so much to offer.
If you were stranded on a desert island, what item would you want to bring with you? Why?
A boat, so I could leave.
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