Which Wolf Do You Feed?

A quiet crisis grips today’s brightest student founders—a tug-of-war between public achievement and private authenticity.  

I recognize it because I’ve lived it.  

At nineteen I signed with McKinsey, Goldman soon after, then private-equity out of undergrad—each move choreographed to climb the ladder.  

My highlight reel was a delusion. I built my résumé with precision while starving my sense of purpose. 

In a battle between two wolves, I chose which wolf to feed. The one driven by fear and status-seeking grew stronger, while the one capable of authentic creation faded. 

Recognizing this pattern in myself first has lent me the conviction to address it in the founders I work with today.  

This hidden battle is between one wolf that seeks authenticity, and another, who serves only ego. This battle, and its outcome, defines our path.  

Feeding the authenticity wolf demands shedding illusions: choosing mastery over recognition, value over vanity, process over outcome.  

It’s Just Theater 

Feeding the wrong wolf is what led me here.  

 I was the first in my family to attend college, so achievement—particularly professional success—meant survival.  

 Each nod from a prestigious brand felt like proof I’d earned my place at Stanford. 

 But these milestones were built on insecurity. Late at night, I’d scroll LinkedIn, each classmate’s fundraising round or like-laden job announcement triggered the same loop: Am I falling behind?  

 It was a quiet optimization for optics, measuring myself against external markers at the cost of internal progress.  

 Each credential became another brick—not laid upward toward meaningful contribution, but inward—sealing my insecurities within a fortress built on sand. 

 Eventually, that fortress became a prison, isolating me from the very world I sought to influence. 

 The cost was the gradual erosion of my agency; unconscious forces directed my path. In blindness, I mistook their invisible hand for fate. 

A Tale of Two Wolves 

In my quest to silence this inner critic, I chased a false prophet: startup prestige.  

I convinced myself I was “too good” for a degree, mesmerized by founders like Evan Spiegel—stories I naïvely attributed to raw ambition alone, dismissing timing, luck, and circumstance. 

The specific form of validation came as a summer startup accelerator: $15k stipend per founder, the promise of building your idea—indistinguishable from countless elite invitations tempting founders today.  

But this wasn’t genuine entrepreneurship; it was theater.  

It offered the optics of being a founder without the bearing the full risk of failure or a leave of absence. I could hedge my bets, dabble in startup life during summer break, and still return to the comfortable certainty of Stanford in the fall.  

The real gift surfaced when an investor paused programming during an information‑session to share a Cherokee parable: 

Hearing this, I saw myself clearly. Not as the ambitious founder persona I projected, but as someone caught in an endless cycle, feeding a wolf whose appetite could never be satiated.  

The parable became a mirror, reflecting not who I had been, but who I still could become—if only I chose to feed the other wolf. 

This drama isn’t mine alone; it plays out in dining halls and dorm rooms, echoed at Coupa and CoHo.  

Courage of Authenticity 

Brilliance is abundant at Stanford. 

What’s rare is courage: the courage to discard polished plans for something messier, riskier, yet infinitely more rewarding—the courage to dismantle your fortress before it becomes your prison. 

True achievement emerges not from certainty, but from audacity. It grows from taking one imperfect step, then another—relentlessly iterating, fueled by what must be earned, never gifted.  

The wolf you feed today shapes your character, defines your legacy, and ultimately determines not just what you build, but who—at your very core—you become. 

But, this path demands patience.  

Recognition comes later, if at all, because the real work happens quietly, behind closed doors, while others seek shortcuts. What emerges from this path isn’t another flashy demo or ratioed response on X, but a vision made tangible through authenticity.  

Feed the right wolf, and the walls fall away; feed the wrong one, and you become them. 

Facing the Wolf Within 

Think back over the past month.  

Did you submit that fellowship application because the idea sparked something authentic in you—or because you worried you’d be forgotten if not recognized? 

Did you scroll through X, stomach tightening with each viral video and RT, each peer’s massive seed round announcement, triggering that familiar worry: Am I falling behind? 

Did seeing an open-source browser agent raise a $10M seed on an uncapped SAFE from a Tier 1 firm make your own ambitions feel inadequate, raising your perceived stakes before you even started?  

Recall that startup idea—the one buried beneath unanswered follow‑ups with CEOs, polite conversations with “friendly” investors, and quiet hesitation in asking your best friend to be your co‑founder—an accumulation of motion that keeps you busy but leaves you unproductive. 

This descent follows a predictable rhythm. Initial excitement fades into caution. The curated image cannot be tarnished. Fear of ridicule—of being the one whose startup is mocked across halls—keeps you from taking the leap. 

And so you play it safe.  

Perhaps you join a “winning pick”—a startup with tier 1 investors and media momentum.

Comfortable. Validating. Safe.  

You tell yourself you’re “learning the ropes” from founders just two or three steps ahead, ignoring that the real difference isn’t talent, but their willingness to risk public failure while you optimize for safety. 

Peers who once admired your clarity begin to wonder what happened to the bold builder.  

Ambition dims into hesitation, softens into compromise, until the promise that earned you a seat at the table becomes just a memory of shelved potential.  

So—which wolf will you feed? 

Thanks to Andy Barkin, Joseph Casey, Zane Sabbagh and David Salib for their comments and thoughts on this piece.