PEAK6's Jenny Just and Matt Hulsizer on 28+ years without a losing year, the Apex FinTech turnaround, and their new startup incubator

Summary

Jenny Just and Matt Hulsizer built PEAK6 into a proprietary options trading firm with no losing years in 28.5 years. They credit this not to superior algorithms but to a deliberate business model choice. Rather than taking directional bets against customers, they positioned the firm as a service provider analogous to Wendy's or Walmart, carrying inventory and delivering it instead.

Both trained at O'Connor Associates on the Chicago and New York options floors before the firm merged with UBS. When UBS wanted to move operations east, they stayed in the Midwest and started their own self-funded trading business. An initial plan to partner with a bank on over-the-counter derivatives never materialized, but the trading operation became their anchor, allowing them to invest across fintech, education technology, and insurance technology.

Apex FinTech Turnaround

Their most consequential operating company acquisition came in 2012 through regulatory pressure. PEAK6 owned Options House, a retail brokerage that predated Wealthfront, Betterment, and Robinhood. Its back-end clearing firm, Pensson, called on a Friday to borrow money. By Monday, the SEC announced fraud at the clearing house and demanded PEAK6 inject $70 million within five days or face liquidation of all customers. Thirteen days later, they acquired what became Apex FinTech Solutions.

Apex now powers 40 million customers through relationships with retail brokerages and fintech platforms. The turnaround required financial stabilization and cultural transformation. Just notes that integrating acquired companies into PEAK6 means balancing preservation of the core 28-year-old trading operation's culture against allowing new businesses to develop their own. Portfolio company CEOs depend heavily on PEAK6's infrastructure in finance, HR, and compliance, but can operate independently at the cost of losing leverage and acceleration benefits.

Culture and Risk Tolerance

Both emphasize that their culture, rooted in trading, requires comfort with daily risk-taking that does not suit everyone. New traders are educated in-house and tend to absorb the collective approach so deeply that few can replicate it elsewhere. The firm runs on urgency, work ethic, and engagement, particularly during volatile market conditions that energize rather than drain participants.

Just brings poker into this framework. She and Hulsizer teach women to play poker specifically to build comfort with risk in male-dominated finance. When Hulsizer began playing poker in 2019, he realized he had been playing options trading for decades. The decision-making under uncertainty maps cleanly between the two domains.

Portfolio and Losses

PEAK6's venture investing arm has grown rapidly as AI became central to their thesis. They describe losing money in more ways than most investors. Their 2009 electric vehicle investment illustrates their willingness to back founders with conviction despite limited due diligence support. They interviewed two candidates: a former PayPal executive pitching electromagnetic trains alongside cars, and a German automotive engineer from BMW with traditional expertise. They chose the engineer's cleaner pitch, only to discover nine months later that the vehicles caught fire and exploded in rain.

Their newer venture arm, PEAK6 Trials, operates as an incubator with built-in advantages. Capital is already deployed, legal and compliance infrastructure exists, and Apex FinTech provides access to 40 million end customers. The model focuses on fintech and insurtech founders who can build directly on top of PEAK6's existing infrastructure.

CEO Selection

Across thousands of employees and hundreds of invested companies, Just and Hulsizer identify self-awareness as the most critical CEO trait. They distinguish this from raw intelligence or confidence. Overconfidence creates catastrophic blind spots. Self-aware leaders control what they can control: effort and attitude. They continuously question their position and remain humble about their competitive advantage rather than assuming superiority over peers. The screening process for this trait remains deliberate but not formulaic; there is no single prescriptive model.