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Conversations, thoughts, and insights

Chicago’s Top Entrepreneurs Give Their Best Advice For Growth And Innovation

By Team PF Apr 20, 2017


Chicago Innovation has been supporting and recognizing Chicago’s entrepreneurs long before the city became known as a hub for high-growth technology startups. The vision of Chicago Innovation is to make Chicago a recognized hub of innovation by igniting a new narrative for our region, strengthening its economic future and building the spirit of innovation throughout the community. The future of Chicago innovation was the focus of the 2017 Past Winners Showcase. The event was hosted at Google, and Mayor Rahm Emanuel spoke as well as a panel of past winners who fuel collaboration and innovation within the Chicago entrepreneurial community.

IMG_4660.jpgThe speakers are all passionate about the opportunity the Chicago community has to collaborate and innovate collectively as a whole, to pave new paths for the young bright minds of the future. Chicago has the most diverse economy in the nation, but the city still strives to see more diversity in the workforce and more inclusive cultures in organizations. Companies should invest in sponsoring students who do not currently have access to the resources that would enable them to bring positive change to the lower income neighborhoods of Chicago. This is just one piece of the conversation the panel of entrepreneurs and Mayor Emanuel gave insight on to shed light onto how to positively invest in the future of Chicago now.

Kristi Ross, Co-CEO and President of tastytrade, led the discussion as the panel moderator. When she asked each speaker to give one piece of entrepreneurial advice for growing and innovating in early stage companies, the importance of knowing these two pieces of your business became clear. Know your purpose and know how to sell. 

“What is one piece of advice you have for the Chicago entrepreneurs who are growing and innovating small businesses?”                                         -Kristi Ross, Co-CEO and President, tastytrade, 2014 & 2013 Innovation Award Winner

 “Focus on selling. That’s it. If you nail that down, everything else will work itself out. To provide more granularity on that, what I mean is get to that point as soon as possible. Understand your customer needs and get to that point when selling. Earlier in my career, I worked for a type of manufacturing company. We would have focus groups come and provide feedback three weeks before the set release date. The customer feedback was super valuable, but the mold was literally already cast. So, when I founded Cleversafe, I made sure we would bring in focus groups right away. Before we even ran anything. And we got a lot of customer feedback that we could actually use.”                                                               -Chris Gladwin, Founder, Cleversafe, CEO & Co-founder, Ocient, 2008 Chicago Innovation Award Winner

“Focus on customer clarity and innovative processes. Really have an environment and organization that is open and truly willing to accept feedback. An environment like this has a humility about it. The more open you are, the more opinions and feedback you will get. Which shows investment in your vision. And you can see the people who really care and want to dedicate themselves to your vision. As a leader, do not just sit there and delegate projects. You should delegate decision making. And empower everyone in the organization to always be innovating. It’s important to have a purpose as your clear North Star, but there is so much opportunity for innovation in every business."                                           -Shradha Agarwal, President and Co-founder, Outcome Health (formerly ContextMedia), 2015 & 2016 Chicago Innovation Award Winner

“My son is graduating college this spring and has a job in enterprise sales. It is an entry level job working as an inside sales rep. Maybe it’s not his dream job, but he will learn to sell. And in order to be successful, you need to know how to sell. If you can learn how to sell, not only will you do well for your company, but you will keep a job. Knowing how to sell is a key skill. As an entrepreneur, each deal won is a big achievement and the only way your small business is generating any revenue.”                                                                                                                                                                   -Matt McCall, Partner, Pritzker Group Venture Capital, Chicago Innovation Awards Board Member

“One of the things I think is critical, and especially being in a mission driven space, is clarity of purpose. Knowing your purpose and not only having clarity of purpose, but also thinking about how you can instill this clear purpose in your culture and make sure your culture and people are aligned. Know that your company is only as strong as the people that represent that vision and purpose.”                                                                     -Brian Bannon, Commissioner & CEO, Chicago Public Library, 2013 Chicago Innovation Award Winner

Thank you, Chicago Innovation, for putting on an incredible event and bringing the brightest minds in the Chicago tech community together to shed light on how, through community building and collaboration, we can be successful entrepreneurs and positively impact the future of Chicago.

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