How Wilson Raised $60M—And Why Money Alone Isn’t Enough

Hector Santiesteban talks with Wilson Zehr, CEO of Cendix and Zairmail, about his career as a serial entrepreneur. Wilson shares his journey from software engineer to entrepreneur, driven by a desire for more control over the direction of his career. He discusses how he navigated challenges like the triple whammy of the dot-com meltdown, 9/11, and the anthrax scare. Wilson explains how his company's responsible financial management during these contractions allowed them to acquire their largest competitor. He also offers his perspective on AI, calling it an enabling technology rather than a single disruptive application. Finally, he reveals his secret to scaling a business: being passionate about using it to change the world rather than focusing solely on money.

Chapters:

• 00:00:00 – Introduction
• 00:01:13 – Experience at Sequin Computer Corporation and first startup, Fusion
• 00:01:38 – Launching and selling Zairmail
• 00:02:10 – The “triple whammy”: dot-com meltdown, 9/11, and anthrax scare
• 00:02:32 – Starting Cendix and reacquiring Zairmail
• 00:02:51 – Raising capital and teaching career
• 00:03:17 – Comparing current economic uncertainty to 2001
• 00:04:15 – High failure rates and the role of good fortune
• 00:04:41 – Managing funds responsibly and acquiring a competitor
• 00:06:05 – Strategy and business cycles
• 00:07:29 – Opportunities during downturns: acquisitions and growth
• 00:08:31 – Economic downturns as trailing indicators
• 00:09:33 – Disappearing industries: paper checks and Yellow Pages
• 00:10:24 – Are cycles accelerating?
• 00:11:16 – Pace of innovation and rapid change
• 00:11:54 – Technology compared to building road systems
• 00:12:58 – Timeless advice for business owners
• 00:13:32 – Downturns as a time to reset and prepare
• 00:15:34 – How businesses secure funding
• 00:16:16 – Venture capital as portfolio investing
• 00:18:28 – How to connect with Wilson
• 00:19:14 – The secret to scaling a business
• 00:19:23 – Running out of capital as the #1 failure point
• 00:19:42 – Why money should never be the sole motivator

Links And Resources:

• Zairmail
• Cendix
• Wilson on LinkedIn
• Amplafy Media
• Hector Santiesteban on LinkedIn
• Hector Santiesteban on Twitter

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