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Unpacking Your Life
Unpacking Your Life

Exploring the crossroads of life, security, and self.

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Unpacking Your Life

Exploring the crossroads of life, security, and self.

My Experience at #CypherCon – Stories, Locks, and Ciphers

Posted on April 5, 2025April 5, 2025 By UPL Admin

I just finished up an incredible time at CypherCon in Milwaukee, and I’m still buzzing from the energy, the people, and the conversations. This con wasn’t just about tech and tools – it was about community, curiosity, and connection.

First off, I’m incredibly grateful for the opportunity to speak and share my story. Getting to talk about my journey – and the story behind my book Undermined – was both surreal and humbling. I wrote Undermined with the hope that it would spark thought, dialogue, and maybe even a little disruption where it’s needed. Being able to discuss it face-to-face with folks who get it was more powerful than I expected. (Also – if you’re curious, Undermined is available on Amazon!) https://a.co/d/9nUYw7j

CypherCon is unlike any other conference. There’s a certain magic in how it blends the technical with the human – how it respects the roots of hacking while still pushing boundaries. I found myself wandering through the various “wards” – each one a rabbit hole of its own.

The IoT Ward was buzzing with people taking apart smart devices, analyzing firmware, and exploring the vulnerabilities that sit just below the surface. It was equal parts terrifying and fascinating. The Lockpicking Ward was a hands-on playground for physical security enthusiasts – and yeah, watching people open complex locks like it was second nature? Wild. I even gave it a shot (with mixed results!).

Then there were the Cypher and Bitcoin Village hacking wards – where brains were firing on all cylinders trying to solve puzzles, break codes, and decipher challenges. It reminded me just how deep the rabbit hole goes, and how much creativity lives in this space.

But more than the tech, what stuck with me were the conversations – hallway chats, random pairings at a soldering table, deep talks over coffee. CypherCon is a place where people see each other – not just for what they do, but for how they think, what they’ve been through, and what they’re trying to build.

To everyone who stopped to talk, to share, to listen – thank you. It meant more than you know.

Until next time.

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ex-Microsoft. There is life on the other side...

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ex-Microsoft. There is life on the other side...

Live your best life every day 😎

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Live your best life every day 😎

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This weekend was a quick trip to our place in Arkansas. I needed to replace some shingles on the roof. I burned my butt through the jeans. Brandi arranged it so I had enough time to replace the exhaust on my 996 on Monday night.

For some reason this trip she took lots of pictures of me. Weird.

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This weekend was a quick trip to our place in Arkansas. I needed to replace some shingles on the roof. I burned my butt through the jeans. Brandi arranged it so I had enough time to replace the exhaust on my 996 on Monday night. 

For some reason this trip she took lots of pictures of me. Weird.

To end our trip last Saturday we had drinks at the Golden Gai, then dinner at The Mayfair Supper Club. A fitting end to a very special weekend with my very special lady. Happy Birthday Brandi.

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To end our trip last Saturday we had drinks at the Golden Gai, then dinner at The Mayfair Supper Club. A fitting end to a very special weekend with my very special lady. Happy Birthday Brandi.

Happy Birthday to my lovely wife @brandioakes. Fun fact we have been married for 26 years and together for 30. Thanks for being my person, and thank you for always being supportive regardless of how crazy the idea ends up being. Love you 😎

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Happy Birthday to my lovely wife @brandioakes. Fun fact we have been married for 26 years and together for 30. Thanks for being my person, and thank you for always being supportive regardless of how crazy the idea ends up being. Love you 😎

Saturday morning at the track. New personal best. Arte Mesuem. Spending time with @brandioakes priceless.

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Saturday morning at the track. New personal best. Arte Mesuem. Spending time with @brandioakes priceless.

Friday evening dinner at Giada... Excellent food and service. White people in a driving shopping cart. Absinthe. Great show. Not for everyone.

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Friday evening dinner at Giada... Excellent food and service. White people in a driving shopping cart. Absinthe. Great show. Not for everyone.
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If you never think you’d be a target, you’re a target.

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— Brian Oakes (@chopperbrian) September 21, 2024
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