When to Quit Your Startup

Matt McGinnis believes that extraordinary results require extraordinary efforts, and that comfort is the enemy of excellence. As COO turned CPO at Rippling, he's developed a leadership philosophy centered on relentless intensity and deliberate understaffing to drive exceptional outcomes.

The core of McGinnis' leadership perspective is that if you want to be in the 99th percentile of outcomes, you must embrace discomfort. "If they ever find themselves in the comfort zone at work, they are definitely making a mistake," he explains. "It's supposed to be really freaking exhausting." This intensity isn't just about working hard—it's about recognizing that in competitive markets, any relaxation creates an opportunity for hungrier competitors.

McGinnis deliberately understaffs projects, believing that overstaffing creates politics and leads people to work on lower-priority items. "It is really important to me that we feel that we've deliberately understaffed every project at the company," he says. This creates productive tension where teams focus only on what truly matters.

He frames this through an "alpha-beta" lens borrowed from finance: high-alpha represents outperformance, while beta represents volatility. Different situations require different approaches—some need high-alpha creativity with tolerance for volatility, while others need low-beta reliability with minimal variance. This framework helps him design systems, processes, and teams appropriate to each context.

McGinnis believes in direct, public feedback and escalation. "Fundamentally the most selfish thing you can do is withhold feedback from someone," he argues. He views customer escalations as gifts that reveal opportunities for improvement, not inconveniences. This transparency extends to his own leadership style—he models intensity by publicly addressing issues, reviewing product flows, and providing feedback in open channels.

For leaders, McGinnis' perspective means you must maintain the founder's intensity at every level of the organization. "Every next concentric circle of management beyond the founder CEO has the potential to be an order of magnitude drop off in intensity. That is fucking dangerous." Your job isn't to buffer people from intensity but to mirror and preserve it.

For ICs, this means embracing discomfort as a sign of growth. When you're tired is precisely when great teams separate from good ones. The practical implication is to escalate issues immediately, give direct feedback, and recognize that extraordinary outcomes require extraordinary effort—but also to maintain perspective that "none of this matters" in the cosmic sense, making the intensity sustainable through appreciation of the opportunity to participate.

Frameworks for Decision Making

McGinnis employs several practical frameworks that leaders and ICs can apply:

• Alpha-Beta Framework: Determine whether a situation needs high-alpha creativity (with tolerance for volatility) or low-beta reliability (with minimal variance).
• SPOTAC: Evaluate people based on whether they're Smart, Passionate, Optimistic, Tenacious, Adaptable, and Kind.
• The Pickle (PQL): Create lightweight checklists that define quality standards, then iterate on them as you learn.
• Power Law + Entropy: Recognize that small improvements at the top end yield disproportionate results, while systems naturally decay without constant energy input.

These frameworks help make decisions about staffing, hiring, process design, and prioritization in a way that maintains intensity without creating bureaucracy.

McGinnis concludes with an important counterbalance: "Play the sport, play it with everything you've got, but never forget that it's just a sport and that none of it matters." This perspective allows the intensity to be sustainable rather than crushing—we work intensely because we have the privilege to participate in something extraordinary, not because we're trapped.