Des W. Woodruff
Founder & CEO — AI, Quantitative Finance & Automation
Des W. Woodruff builds companies at the intersection of AI, quantitative finance, and automation. Across every venture, the pattern is the same: see an opportunity before it's obvious, determine whether it's real, then build a system that scales without requiring him at the center of it.
He's been early enough times to treat pattern recognition as a discipline — and wrong enough times to stay humble about it.
What he builds
Track record
For the record
Competitive chess player, two-time state racquetball champion, and — according to 23andMe — a paternal-line relative of King Louis XVI. Make of that what you will.
Where it starts
Faith sits at the top of how Des makes decisions — the fixed point everything else gets measured against. It isn't branding, and it isn't a variable to optimize. It's the order of operations: the foundation the rest is built on, and the standard it's held to.
More than two decades in, the throughline hasn't changed: build for what's next, execute on what's real, and stay grounded in what doesn't move.
Let's connect
Des speaks on entrepreneurship, AI, quantitative markets, and crypto, and partners with builders, investors, and operators working on what's next. If you're building something ambitious, backing something unconventional, or just want to compare notes with someone who builds for a living, reach out.
des.woodruff at gmail
He's been early enough times to treat pattern recognition as a discipline — and wrong enough times to stay humble about it.
What he builds
- Grok Management, LLC — quantitative investment management focused on systematic and quantitative trading.
- Grok Trade — trading education, founded in 2007 as FreeTradingVideos.com and now serving students in 160+ countries.
- GrokCor AI — custom AI solutions, business automation, and customer engagement that does the unglamorous work businesses actually run on.
- Dezz, Inc. — a personal AI companion built around persistent memory and deep personalization, so the relationship compounds instead of resetting. Beta soon.
Track record
- Featured on NASDAQ for entrepreneurship, Forbes for combat-sports business, and TradingView for technical analysis
- Early Bitcoin adopter, with a first entry under $1,000, and moderator of a major cryptocurrency community
- Founded one of the first online automotive-sales platforms (AutoIndiana.com) and one of the earliest online mortgage-processing companies (HomeProcessing.com)
- Co-founded a sanctioned U.S. bare-knuckle fighting promotion (ValorBK.com) and helped develop its Bout Circle competition format
- Applied an AI agent to a sales funnel, producing a 153% conversion lift
- Developed proprietary technical-analysis setups and systematic trading algorithms
For the record
Competitive chess player, two-time state racquetball champion, and — according to 23andMe — a paternal-line relative of King Louis XVI. Make of that what you will.
Where it starts
Faith sits at the top of how Des makes decisions — the fixed point everything else gets measured against. It isn't branding, and it isn't a variable to optimize. It's the order of operations: the foundation the rest is built on, and the standard it's held to.
More than two decades in, the throughline hasn't changed: build for what's next, execute on what's real, and stay grounded in what doesn't move.
Let's connect
Des speaks on entrepreneurship, AI, quantitative markets, and crypto, and partners with builders, investors, and operators working on what's next. If you're building something ambitious, backing something unconventional, or just want to compare notes with someone who builds for a living, reach out.
des.woodruff at gmail
Stunt double unnecessary.
— Des
— Des