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The Path to Operational Success with Chris Gladwin and Mike Evans

The Path to Operational Success with Chris Gladwin and Mike Evans


Chuck Templeton is joined by fellow Chicago entrepreneurs and old pals Chris Gladwin and Mike Evans for a captivating conversation about scaling their respective companies for exit. Chris is the founder of CleverSafe and is currently the CEO of Ocient, a data analytics platform for the largest data sets. Mike is the founder of Grubhub and the current CEO of Fixer, a home maintenance membership company. Chris and Mike compare their customer acquisition experiences, discuss their hiring approaches, consider why they all happen to be endurance athletes and dig into their “just start” and “stay in business” philosophies. Not only did Chris and Mike each have one successful exit but they’re trying to “bottle lightning” again. It’s a conversation any entrepreneur is sure to find valuable insights in. 

Key Takeaways:

  • Customer acquisition for enterprise companies and small businesses: Mike shares how he thought about building a brand and providing customers with value early on. Chris speaks to his approach to customer discovery and the importance of understanding the buyer’s motivations.

  • The “just start” and “stay in business” mentalities: According to Mike, the only way to know if customers will buy your product is to get out there and sell it. According to Chris, the number one reason businesses fail is because they don’t last long enough.

  • What endurance sports can offer entrepreneurs: A learning mindset and a lot of pain.

  • Hiring for scale: Chris and Mike both share how they approached hiring and maintaining talent through different stages of growth.

  • Building companies for exit: Chris and Mike discuss their philosophies on designing a company for exit from creating a template based on similar companies and taking measures to improve the probability of an exit


The Path to Operational Success with Chris Gladwin and Mike Evans
00:00 / 01:04


Josie Lane

Art Director


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This content is for informational purposes only, should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security, and is not directed at any investor or potential investor in any investment vehicle sponsored by S2G Investments, LLC or its affiliates (“S2G Ventures”). Investing involves risk, including the risk of loss. The opinions expressed do not necessarily represent the views of S2G Ventures. Specific companies are mentioned herein solely for educational purposes and should not be construed as an endorsement of any particular company or investment. Please note that S2G Ventures may maintain investments in the companies mentioned herein.

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