Jackson Osborn

Predictive Macro Strategist · Founder, Daedalus Intelligence Group
Emailjackson.osborn@daedalusadvisorygroup.com
Phone708-593-1960
LocationChicago, IL
LinkedIn
Global Competition Rank
#1
dYdX Top Performer 2023
750,000+ traders worldwide
Annual Return · Digital Assets
0%
Client portfolio performance
2024 fiscal year
Cumulative P&L · All-Time Record
0%
Highest in dYdX exchange history
Surpassed prior record by 82%
Selected Trade Performance01

Selected
Returns

Discretionary
2025
IREN
Equity · Bitcoin Mining
+1223%
AMD
Equity · Semiconductor
+415%
Silver
Commodity · Futures
+178%
Tesla
Equity · Consumer
+110%
Gold
Commodity · Macro
+103%
S&P 500
Index · Benchmark
+42%
Annual Returns vs S&P 500 · 2021–2025
Jackson Osborn
S&P 500
Professional Experience02

Career
History

8+ Years
Markets
Apr 2026 — PresentChicago, IL
CEO & Managing Principal
Daedalus Intelligence Group LLC
  • Founded Daedalus Intelligence Group LLC to advise corporate treasury teams on when and where to deploy capital in hard asset and commodity markets, using a predictive framework built over 9 years of live market research.
  • Work with CFOs and boards to identify asymmetric entry points in gold, silver, the S&P 500, and commodity markets before moves develop, sizing positions to capture upside while limiting downside exposure.
  • In active NDA-covered discussions with a top-5 global multi-strategy fund regarding macro research and commodity timing advisory.
Mar 2017 — PresentChicago, IL
Professional Trader
Independent
  • Awarded Top-Performing Trader of 2023 on one of the world's largest DEXs out of 750,000+ users, achieving a 17,763% cumulative P&L, an all-time exchange record.
  • Surpassed the exchange's previous all-time high performance record by 82%.
  • Developed a thesis on parabolic movement of speculative assets that became a repeatable 17-12:1 risk-reward strategy.
  • Leveraged proprietary tools to consistently rank top 0.05% in multiple global competitions.
Mar 2021 — Oct 2025Austin, TX
Portfolio Manager & Multi-Asset Research Analyst
Daedalus Management
  • Generated a 400%+ annual return for digital asset clients in 2024.
  • Built a multi-layered quantitative framework that accurately identified 92% of every major S&P 500 bottom over 16 years in real time.
  • Delivered monthly performance reports detailing exposure, portfolio weighting, and return projections, beating the S&P 500 every year since 2021.
  • 2025 discretionary trades: SPX (+42%), Gold (+103%), Silver (+178%), AMD (+415%), Tesla (+110%).
Jan 2019 — Mar 2020Chicago, IL
Startup Founder
RiseHigher
  • Built a concierge training app for high-rise buildings that increased renter acquisition and retention by 15%.
  • Negotiated contracts with vendors, suppliers, and partners while maintaining cost-effectiveness objectives.
Aug 2018 — Feb 2019Chicago, IL
Account Executive
Yelp
  • Top 1% in sales nationally. Built an upsell approach adopted by the entire Chicago office.
  • Highest client retention on the floor for multiple months. Named #1 New Account Executive 2019.
Career Achievements03

Key
Achievements

7 Years
Active
Cumulative P&L — All-Time High
0%
The highest cumulative P&L in dYdX exchange history, from a pool of 750,000+ global traders. Surpassed the previous record by 82%.
Annual Return — vs S&P 500 · 2024
400% VS S&P 23%
2024 RETURNS
Jackson +400%
S&P 500 +23%
Outperformed the S&P 500 by 17× in 2024 through systematic digital asset management.
S&P 500 Bottom Detection Accuracy
92%
Proprietary quantitative framework, validated across every major S&P 500 bottom since 2011.
S&P 500 · 10-Year Price History
Competition Rank — Global
#1of 750,000+
Top Performer 2023 on dYdX. Top 0.05% across multiple global competitions. Beat the S&P 500 every year since 2021.
Bitcoin Track Record03.5

Every Recommendation
on Bitcoin

2017
2026
Bitcoin price · Linear scale · 2017–2026
Entry recommendation
Exit recommendation
Investment Philosophy & Methodology04

The
Approach

3 Core
Strategies
01
Parabolic Movement Thesis
A proprietary framework for identifying parabolic moves in speculative assets before they develop. Refined over eight years into a repeatable 17-12:1 risk-reward strategy, deployable across commodity and equity markets with consistent conviction.
17-12:1 Risk-Reward · Repeatable
02
Quantitative Bottom Detection
A multi-layered quantitative framework that identified 92% of every major S&P 500 bottom over 16 years, in real time. Combines systematic signals with macro discretion for asymmetric entry timing at high-conviction inflection points.
92% Accuracy · 16-Year Validation
03
Multi-Asset Macro Allocation
Cross-asset portfolio management spanning equities, commodities, derivatives, and digital assets. Monthly performance reports detail exposure, weighting, and return projections. Beat the S&P 500 benchmark every year since 2021 across varying macro regimes.
S&P 500 Beat · 2021–2025
Skills & Expertise05

Edge &
Toolkit

Hard & Soft
Skills
01 · Quantitative
Quantitative Systems Design
Built multi-layered quantitative frameworks validated across 16 years of market history. Translates complex pattern recognition into systematic rules that execute without emotion, repeatable, back-tested, and auditable.
TradingViewBacktestingSignal DesignSystematic Rules
02 · Markets
Multi-Asset Market Fluency
Active across equities, commodities, derivatives, and macro instruments. Deep understanding of cross-asset correlation, sector rotation, and regime detection, identifying opportunity wherever it surfaces.
EquitiesDerivativesCommoditiesMacro
03 · Risk
Position Sizing & Risk Architecture
Engineered a 17-12:1 risk-reward framework with strict entry/exit discipline. Manages drawdown as rigorously as upside. Consistent profitability comes from knowing when not to trade as much as when to enter.
17-12:1 R/RStop ArchitectureDrawdown Control
04 · Research
On-Chain & Fundamental Analysis
Reads on-chain data flows, wallet activity, and protocol metrics as primary signals. Layers this with traditional fundamental analysis to build high-conviction theses before price action confirms them.
On-Chain DataDeFi ProtocolsFundamental Analysis
05 · Reporting
Client Reporting & Portfolio Communication
Delivered institutional-grade monthly performance reports covering exposure, weighting, attribution, and forward projections. Translates complex market dynamics into clear, confident client-facing narratives that build trust.
Performance AttributionClient ReportingPortfolio Construction
06 · Psychology
Conviction & Execution Under Pressure
Eight years of live trading with real capital sharpens one skill above all: acting on a thesis with size and discipline when others cannot. Consistent top-0.05% performance across global competitions is not luck. It is process.
Trade DisciplineHigh-Conviction EntryConsistency
07 · Adaptability
Cross-Regime Market Experience
Has generated positive returns through rate hike cycles, post-COVID expansion, commodity supercycles, and volatile digital asset markets. Adapts strategy to the environment rather than forcing one playbook onto all conditions.
Macro RegimesRate CyclesAdaptive StrategyMulti-Environment
Contact06
Open to Opportunities

Seven Years.
Every Market.
Consistent Results.

View LinkedIn
Emailjackson.osborn@daedalusadvisorygroup.com
Phone708-593-1960
LocationChicago, IL