John Sterling enjoyed a $200 million-dollar exit - now he helps others reach success! episode artwork

EPISODE · Mar 11, 2026 · 1H 7M

John Sterling enjoyed a $200 million-dollar exit - now he helps others reach success!

from Build Better Business Podcast with Chuck Crumpton · host Chuck Crumpton

John Sterling is a Citadel University graduate (BA in Political Science, 1983) who led Datastream to a $200 million exit. He currently serves as CEO of Sterling Ventures Group, which "buys and grows B2B SaaS companies quietly and intentionally". His portfolio includes Sterling Sales (sales coaching and training). John's sales training approach addresses multiple components beyond just training salespeople, including lead generation, pricing correction, and most importantly, developing the right "avatar" or ideal salesperson profile. Sterling openly discussed his journey with alcohol addiction, describing how he initially justified his drinking because he was successful professionally. With the help of a therapist he's been seeing for six years, he eventually stopped drinking and found life "10 times better without it".   John advocates talking to advisors quarterly and working on business value even if an exit is 10 years away. He recommends maintaining realistic optimism, expecting good things while accepting that "out of 10 great things, one of them going to go sideways".If you like the content on this podcast, you may want to look into our 6-month Leadership Lab (virtual mastermind) Sales Track course that can definitely help you grow the sales arm of your business. Call me and let's discuss it. Enjoy the conversation!Chuck Crumpton   864.915.0066

John Sterling is a Citadel University graduate (BA in Political Science, 1983) who led Datastream to a $200 million exit. He currently serves as CEO of Sterling Ventures Group, which "buys and grows B2B SaaS companies quietly and intentionally". His portfolio includes Sterling Sales (sales coaching and training). John's sales training approach addresses multiple components beyond just training salespeople, including lead generation, pricing correction, and most importantly, developing the right "avatar" or ideal salesperson profile. Sterling openly discussed his journey with alcohol addiction, describing how he initially justified his drinking because he was successful professionally. With the help of a therapist he's been seeing for six years, he eventually stopped drinking and found life "10 times better without it".   John advocates talking to advisors quarterly and working on business value even if an exit is 10 years away. He recommends maintaining realistic optimism, expecting good things while accepting that "out of 10 great things, one of them going to go sideways".If you like the content on this podcast, you may want to look into our 6-month Leadership Lab (virtual mastermind) Sales Track course that can definitely help you grow the sales arm of your business. Call me and let's discuss it. Enjoy the conversation!Chuck Crumpton   864.915.0066

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John Sterling enjoyed a $200 million-dollar exit - now he helps others reach success!

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This episode is 1 hour and 7 minutes long.

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This episode was published on March 11, 2026.

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John Sterling is a Citadel University graduate (BA in Political Science, 1983) who led Datastream to a $200 million exit. He currently serves as CEO of Sterling Ventures Group, which "buys and grows B2B SaaS companies quietly and intentionally". His...

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