The First Customer - How To Avoid The Pain of Missed Opportunities with Founder Charles Sims

The First Customer

In this episode, I was lucky enough to interview Charles Sims, CEO and founder of Investimate.
Charles shares how he grew up around innovation and leadership inspired him to build and scale ventures, starting with a paintball supply company as a child. His ability to adapt and thrive in chaos earned him the moniker "Hurricane CTO" during his tenure with organizations like the LA Clippers and United Talent Agency, where he became known for troubleshooting crises and bringing stability to high-pressure situations. Now, with Investimate, he is channeling his expertise into a platform that helps founders refine their pitch decks, evaluate market opportunities, and secure investment with data-driven insights.
Reflecting on past challenges, Charles discusses a missed acquisition opportunity where he struggled to frame the value proposition, only to later see the deal double in value after another company acquired it. This failure pushed him to develop structured frameworks for assessing investments more effectively. He also emphasizes the importance of leadership, not just in taking accountability but in fostering growth by allowing others to take risks while providing a safety net.

Sit back and listen as Charles highlights the resilience and adaptability required to navigate the entrepreneurial world, making him a valuable voice in the startup ecosystem in this episode of The First Customer!

Guest Info:
Investimate
https://investimate.io
Charles Sims' LinkedIn
https://www.linkedin.com/in/charlessims/

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