ABOUT THIS EPISODE
Dexter Caffey grew up in Youngstown, Ohio, studied business finance at Youngstown State, and spent more than two decades in Atlanta running his own futures and options firm, managing over $100 million and hedging for Dow-level clients. Then, sitting next to a stranger at a cybersecurity event in Israel, he realized he could read everything on the man's screen. The idea that followed got called the dumbest he'd ever heard. Dexter took that personally and built Smart Eye Technology, which uses continuous biometric authentication so only the right person can see what's on the screen.
This conversation is about what it takes to become a beginner again after you've already climbed a mountain. Dexter's answer starts at 16, when he paid his own private school tuition with busboy wages, and runs through enterprise sales cycles that take years to close. Along the way, Jaime and Jonathan dig into risk, rejection, and why the people who keep showing up are usually the ones who end up looking lucky.
In this episode
- The "dumbest idea" that launched Smart Eye Technology, and the $50,000 lunch that funded the research
- Paying his own way through private school at 16, and the grit it built
- Why being uncomfortable is where success lives
- Living with risk every second in futures and options, and admitting you're a risk taker at heart
- Treating no as information, and pulling the useful part out of a harsh review
- Water in the desert: selling to the problem instead of the feature list
- The bank president who told Dexter to put his technology on the things banks already use
- Why your emotions are liars, and what an angry golf swing teaches about it
- The event you didn't feel like going to, and why it's usually the one that matters
- Two- to three-year enterprise sales cycles, and staying in the game long enough for luck to find you
- Courage versus confidence, and the Barry Goldberg school of self-belief
- When your baby becomes everybody's baby: guarding the core against feature requests
- Being the person people say you need to meet, and why givers find each other
Worth repeating
> "So you want me to be the first sucker?" "No, I want you to be the first investor." – Dexter, recounting his first pitch
> "Your emotions are liars. So if you're relying on your emotions, you're relying on a liar." – Dexter
> "Success is what you say no to. It's not what you say yes to." – Dexter
> "Sometimes it looks like luck, but that's because I just swung the bat a thousand times in a row and I finally hit a home run." – Jonathan
> "At some point, you're going to have to place a courage bet somewhere." – Jaime
Chapters
- 00:00 Cold open and introducing Dexter
- 02:03 Youngstown, Atlanta, and 23 years in futures and options
- 02:56 The idea that hit at a cybersecurity event in Israel
- 05:25 The $50,000 lunch
- 08:04 Paying his own way at 16
- 11:41 Success lives where you're uncomfortable
- 13:08 A worldview shaped by risk
- 16:28 The fear of hearing no
- 20:37 Success is what you say no to
- 21:33 The market as a listening device
- 23:16 Water in the desert
- 24:56 Put it on the things we already use
- 28:51 When the nos pile up
- 30:12 Your emotions are liars
- 36:55 Keeping your energy topped up
- 38:14 The event you didn't feel like going to
- 40:02 A fraud that proved the point
- 41:47 The slow burn
- 43:44 Two to three years to land an enterprise account
- 44:53 Swinging the bat a thousand times
- 48:09 Protecting your mindset
- 50:30 Knowing you belong in the room
- 52:43 Courage versus confidence
- 55:34 Taking risks once the thing is running
- 57:48 When your baby becomes everybody's baby
- 01:00:08 A different flavor of hard
- 01:02:01 Overnight successes that took a decade
- 01:03:38 Be the person people say you need to meet
- 01:08:39 Givers find each other
- 01:13:26 Zig Ziglar and the traveling salesman
- 01:16:59 Where to find Dexter
Connect with Dexter
- Dexter Caffey on LinkedIn
- Smart Eye Technology
And yes, Google "Dexter Caffey Pharaoh."
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Red Threads is an email with one idea a week that changes how you see your work, written by Jaime Solis as part of Tandem Studio.
Straight to your inbox. Always free.
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The Slackers Podcast is produced by Jaime Solis and Jonathan Sasse.
Audio production by Stephen Kallao.
Cover art by Jonathan Sasse
Connect with Jonathan & Jaime
🎙️ Jonathan Sasse — Co-Founder Tandem Studio and executive advisor.
🔗 LinkedIn · Forbes Communication Council
🎙️ Jaime Solis — Music executive, Content & Media advisor, founder Red Threads newsletter.
🔗 LinkedIn · Threads · Instagram
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