Why Failed Startup Founders Are Your New "What-Not-to-Do" Gurus (And Why That's Hilarious)
Move over unicorn founders and serial entrepreneurs; there’s a new headliner in the startup circus. Enter the failed founder-turned-advisor. A modern-day oracle who couldn’t quite figure out how to keep their own venture afloat but now wants to guide yours to success. It’s like hiring someone who flunked out of med school to give you health tips.
How did we get here? Well, it turns out failure is no longer just an unfortunate setback, it’s a golden ticket to credibility in the startup world. Lost millions in investor money? Stumbled into bankruptcy? Perfect! That’s your résumé now. These “what-not-to-do” experts are popping up everywhere, dispensing wisdom with the kind of confidence you’d expect from someone who’d never made a mistake in their life.
And while they sip their matcha lattes in glass-walled WeWork sanctuaries, one can’t help but wonder: Are we really supposed to take advice from the person who already drove their startup into a ditch? Sure, they might be great at pointing out potholes, but wouldn’t it be better to listen to someone who actually made it to the destination? Just a thought.
The Failed Founder’s Pitch: “I Know What Not to Do, So Trust Me!”
At first glance, the failed founder’s pitch sounds logical enough: “I’ve seen the dark side of entrepreneurship and returned to warn you.” They’re the Odysseus of the startup world... if Odysseus had sailed straight into the Cyclops’s cave, lost his entire crew, and still somehow landed a book deal about it. But let’s unpack this a little. Knowing what not to do is not the same as knowing what to do. It’s like hiring a chef whose signature dish is “charred everything” to run your kitchen. Sure, they might stop you from over-salting the soup, but don’t expect a souffle to rise under their guidance.
Many of the mistakes these failed founders harp on about are so obvious they’re practically clichés.
Overspending?
Misjudging market demand?
Hiring your college roommate to be your CTO?
These aren’t exactly pearls of wisdom; they’re more like the kind of basic advice your mom might give over Sunday dinner. “Don’t spend more than you make” and “hire people who actually know what they’re doing” are hardly groundbreaking revelations.
The irony is delightful. The same people who didn’t see the most obvious banana peels on the sidewalk are now posing as Sherpas to guide others up the entrepreneurial Everest. They might prevent you from tripping over the same peels they did, but who’s to say they won’t lead you straight into a crevasse? It’s easy to point out the pitfalls you’ve already fallen into. The question is whether they can steer anyone toward actual success, or if their advice ends at “avoid obvious mistakes” and fades into the startup equivalent of a shrug emoji.
Romanticizing Failure: Where Did We Go Wrong?
In the startup world, failure is practically a parade float, festooned with banners that say “Fail Fast, Fail Often!” and confetti made of shredded investor term sheets. It’s no longer just a mistake; it’s a badge of honor, as if losing millions of dollars and burning through goodwill were some kind of entrepreneurial bar mitzvah. But let’s slow down for a second. While failure can indeed teach lessons, there’s no universal rule that it transforms you into a wise sage. Sometimes, failure just means… you failed.
And yet, here we are, handing out credibility like party favors to anyone with a sob story about scaling too fast or forgetting to validate market demand. Imagine applying this same logic to other industries.
Would you book a flight with a pilot who proudly advertises, “I’ve crashed three planes, but boy, did I learn a lot!”?
Would you let a surgeon near your appendix after they declare, “Botched enough surgeries to finally get it right... maybe.”
But in the startup world, we elevate these characters to advisory roles, crowning them as the very people to guide others.
This romanticization creates a self-sustaining feedback loop where failure is accepted and fetishized. Those with actual, demonstrable success? Dismissed as anomalies, freaks of good fortune who “never really learned the hard way.” The message is clear: if you didn’t crash and burn, your wisdom doesn’t count. Meanwhile, the failed founder-turned-advisor marches forward, recycling their tale of woe for new audiences, while quietly glossing over the part where success remains just as elusive for them as it is for their protégés. The result? A culture that glorifies flops instead of focusing on what actually works.
The Real Game: Playing Startup Ecosystem Bingo
The failed founder-turned-advisor isn’t here because they’re brimming with untapped wisdom. They’re here because the startup ecosystem thrives on optics, and nothing screams “empathetic and relatable” quite like hiring someone who’s belly-flopped off the entrepreneurial high dive. For venture capitalists, it’s a brilliant PR move. “Look,” they say, pointing proudly to their new advisor, “we hired someone who gets it because they’ve suffered too.” Apparently, losing millions in someone else’s money is the new MBA.
But what about the failed founder themselves? It’s a win-win. Instead of disappearing into the LinkedIn void of irrelevant titles, they’ve figured out how to repackage failure as a feature, not a bug. The playbook?
Sell cautionary tales of hubris and heartbreak.
Brand yourself as a maverick, a contrarian who knows the road because they’ve been flattened by it.
Quietly sidestep any real accountability for your own mistakes.
It’s the entrepreneurial equivalent of playing startup bingo: pivot, cash out, spin a redemption arc, repeat.
And where does this leave the first-time founder? Stuck in an echo chamber of “don’t do this” advice, with no real roadmap for what should be done. Sure, their new advisor might keep them from overspending on office beanbag chairs, but what about managing complex market dynamics, scaling responsibly, or turning a profit? That’s when the cracks begin to show. The failed founder’s expertise doesn’t extend to problems they never encountered, leaving the next wave of startups to fail in excitingly novel ways.
In the end, it’s a perfect hustle. The failed founder stays relevant, the VC firm looks progressive, and the new founder? Well, they’ll have a cautionary tale of their own soon enough.
Success Is the Best Advisor, So Why Aren’t They Doing It Themselves?
If failed founders have truly unlocked the secrets of startup survival through their “transformative” failures, why aren’t they putting that hard-earned wisdom to work in their own profitable, sustainable ventures? Shouldn’t they be out there raising Series C rounds, not dishing out “lessons learned” PowerPoints to early stage founders?
The cynical answer is as obvious as it is uncomfortable: critiquing is infinitely easier than creating. Being an advisor is the ultimate no-risk gig. There’s no messy product development, no late-night fire drills, no investors breathing down your neck about “hockey-stick projections.” It’s all parachute in, nod wisely, sprinkle in some “don’t-do-this” anecdotes, and exit stage left before any real results are due. Accountability? Never heard of it. It’s consulting without the deliverables, therapy without the empathy.
If someone truly had the magic formula for building a sustainable, profit-generating business, they’d be applying it to their own venture, not serving it lukewarm on a platter of generalized advice. This isn’t to dismiss the role of advisors altogether; many provide crucial guidance. But when your only credential is failure, the gap between “I know what not to do” and “I know how to succeed” becomes glaringly obvious.
Startups need advisors who can chart the course, not just point out the icebergs they personally rammed into. The failed founder-turned-advisor is often more lifeguard than captain, shouting “Watch out!” from the shore while you’re left swimming in uncharted waters. If they really knew how to sail, wouldn’t they already be steering their own ship?
The startup ecosystem’s love affair with failed founders as advisors feels less like an inspired strategy and more like a collective coping mechanism for an industry that’s addicted to hype. It’s as if the mantra “Fail fast, fail often” has morphed into “Fail spectacularly, and we’ll make you an advisor.” Sure, failure can be a teacher, but it’s not an MBA. The real qualification is knowing how to build, adapt, and thrive in complex markets; not just knowing how to write a Medium post titled “What My Failure Taught Me About Resilience.”
Next time a failed founder strolls into the room pitching themselves as a startup whisperer, ask the real questions.
Where’s the proof they’ve learned anything from their mistakes beyond how to monetize a redemption arc?
Can they actually guide you toward success, or just help you sidestep the same banana peels they slipped on?
If they’re so wise, why aren’t they busy building the sustainable, profitable business they claim to know how to create?
It’s time to stop romanticizing failure and start rewarding competence. Until then, we’ll keep hiring advisors who are experts at spotting potholes but utterly clueless at laying asphalt. Hindsight is 20/20, but apparently, it also pays six figures.