Every founder goes into the woods. We hike into a psychological space where the rules of the ordinary world stop applying, where the things you believed about yourself and your market get tested by forces you didn’t anticipate, and where coming home means becoming someone you can’t fully explain to the people who watched you leave. Stephen Sondheim wrote a musical about this in 1988 and called it Into the Woods. You might have seen the movie. Most people think it’s about fairy tales; it’s about you.
I had the joy of watching a stage production, years ago, and found myself doing what I always do: watching a story unfold and realizing it had nothing to do with fairy tales and everything to do startups (I’m a dork like that). The kid playing Red Riding Hood was bouncing around the stage, grabbing pastries from the Baker, completely oblivious to the Wolf’s real intentions. The audience knows what she doesn’t. The Wolf’s song of seduction makes it obvious that what’s coming isn’t charming; it’s predatory. And yet Red skips right into it because the Wolf is, as she later observes, “nice.” She goes willingly. She gets consumed. She comes out the other side and delivers the most founder-relevant line in the entire show: “He showed me things that I never had seen.”
Experience brings wonder. It also brings scars. And if you’ve started a company, you know these aren’t different things.
Article Highlights
The Woods Are Not Optional
Sondheim’s woods are not just a setting, they’re an obvious psychological symbol of the unconscious, and I’d argue they’re also the most accurate representation of what pre-revenue startup life actually feels like. Dark. Unfamiliar. Full of things that might eat you. Maurice Sendak would call it “where the wild things are,” and those wild things (your doubts, your ignorance about unit economics, the co-founder disagreements you’re pretending don’t exist) must be befriended and integrated into the psyche before you can build anything durable. The Baker’s Wife, in Into the Woods, says it perfectly when she tells her husband, deep in their quest, “You’re different in the woods.” He’s surer, more daring, and much more open-hearted. The defamiliarization of the woods creates a space for growth that the ordinary world never provides.
Sound familiar? Every founder I’ve worked with has had a version of this moment. You leave your comfortable job, your predictable income, your understood identity, and you walk into the woods of entrepreneurship, where nobody knows your title, nobody cares about your resume, and the only thing that matters is whether you can survive long enough to learn what the woods are teaching you. As I’ve written about the habits of highly successful entrepreneurs, entrepreneurship demands the discipline to turn questions into numbers, tradeoffs, and constraints. The woods demand the same thing while being wary of more wolves.
Joseph Campbell documented this pattern decades before Sondheim staged it. In The Hero with a Thousand Faces (1949), Campbell described what he called the monomyth: a hero ventures forth from the world of common day into a region of supernatural wonder, fabulous forces are encountered, a decisive victory is won, and the hero comes back with the power to bestow boons on his fellow man. I love exploring how a generation of entrepreneurs was inspired by this thanks to Star Wars. Separation, initiation, return, and accomplish, every culture tells this story. Every founder lives it, whether they recognize it or not. The call to adventure is the problem you can’t stop thinking about. The threshold is the day you file your articles of incorporation. The ordeal is every pitch that goes sideways, every customer who ghosts you, every board meeting where someone asks why your burn rate looks like the wood on fire.
But Sondheim does something Campbell’s framework misses, and it’s the part that matters most for founders: he focuses on the aftermath. Not the quest itself but what happens when the quest succeeds and you’re standing there holding exactly what you wished for, wondering why it doesn’t feel the way you thought it would.
Nice Is Different Than Good
One of the most wonderful lines in Into the Woods belongs to Red Riding Hood after her encounter with the Wolf. She tells the Baker, simply, “Nice is different than good.” The Wolf was nice; charming, even. He made promises, he paid attention, he seemed interested in her well-being. And then he ate her. The word nice in Sondheim’s vocabulary is the veneer that conceals either disregard or danger, and if you’ve spent more than a few months raising capital, you’ve met plenty of wolves wearing nice.
Cinderella, in the show, discovers the same thing from a different angle. She wishes to go to the festival, she meets Prince Charming, and then she does something most fairy tale heroines don’t: she runs away. Why? Because as she tries to describe him to others, all she can muster is, “He’s a very nice prince.” Nice. Not good. Not real. Not someone who understands what she actually needs. She marries him anyway, which sets up every disillusionment in Act II, and if that isn’t the most accurate description of a founder taking the wrong investor’s money, I don’t know what is.
I’ve watched this script play out in real time. A founder meets an investor who says all the right things: “We love your vision,” “We want to be partners,” “We’re founder friendly.” Nice. And then the term sheet arrives, and it’s a different story. Perhaps you’ve joined an accelerator that took equity while pretending it was a better deal, and then you sit in the coworking space expecting help, only find events and office hours. Or you close a round and the board seat gets filled, and suddenly the “partner” is asking why you haven’t hit revenue targets that were never realistic in the first place. There is a distinction between investors who buy proof versus those who invest in belief; some investors want to see revenue traction, defensible margins, and a path to predictable multiples, and in many contexts, that’s appropriate. But when they dress it up as partnership while pricing your desperation, that’s the Wolf in a nice suit.
Sondheim’s Witch calls this out with the kind of bluntness that every founder needs to hear: “You’re so nice. You’re not good, you’re not bad, you’re just nice. I’m not good, I’m not nice, I’m just right.” The Witch is the advisor who tells you what you don’t want to hear. She resonates with me. She’s the market that doesn’t care about your feelings. She’s the data that contradicts your pitch deck and she’s not trying to be liked; she’s trying to be accurate. And most founders, like most fairy tale characters, would rather listen to the nice Wolf than the right Witch.
You Know Things Now That You Never Knew Before
Each of the main characters in Into the Woods follows the arc from innocence to experience. Red learns about predation. Cinderella learns about the emptiness of getting what you wished for. Jack, the boy who traded the family cow for beans, has the most mystical experience of the three. He climbs the beanstalk, encounters giants, and comes back fundamentally altered. His song “Giants in the Sky” is the best reflection of a founder’s post-funding psychological state I’ve ever encountered in any medium: you think of all the things you’ve seen, you wish that you could live in-between, and you’re back again, only different than before. After the sky.
That “different than before” is the part that the startup industry refuses to talk about. The Kauffman Foundation has shown that entrepreneurial persistence, not initial funding, is the strongest predictor of eventual startup survival, passion and perseverance for long-term goals. But what startup frameworks never address are the costs of the transformation itself. Jack doesn’t just come home with gold. He comes home as someone who has seen giants, who has been to a place no one around him can understand, and who now has to live in a world that looks the same but feels completely different. As Jack himself says, “You know things now that you never knew before.”
Here’s one thing most don’t know that you probably didn’t know before
Investor Jerry Neumann just wrote about this in Colossus. Co-Author of Founder vs. Investor (with Elizabeth Joy Zalman), Neumann touches on something I’ve been asking for decades. Why do we celebrate that 90% of startups fail, as encouragement to founders that it’s difficult, without appreciating that we’ve been saying “90% of startups fail” since the 90s? At what point does all the work make a difference? This is the underlying premise of the Startup Ecosystems book; that despite accelerators, methodologies, research finding correlations with founder success, and studies exposing why startup fail, shouldn’t more startups survive?? And then ecosystem builder Eric Harry asks, “is the work actually working?” No! We’re not applying what we know.
I wrote about this big idea in The Startup of You: companies pivot, markets change, capital moves, but a human being carries their history, their losses, their love, their resilience into every room they enter. That is the real startup and our economy doesn’t lean in on who we are. The research from Oxford, University of Technology Sydney, and the University of Melbourne that I covered when examining founder personality traits found that about 8% of people worldwide possess personality traits conducive to being successful founders. Eight percent. The rest aren’t deficient; they just aren’t wired for the woods. And the ones who go into the woods anyway, without the wiring, without the preparation, without the self-awareness? Those are the ones who get eaten.
Careful the Things You Say
Sondheim saves his knife for the finale when the Witch, who has spent the entire show trying to protect her daughter Rapunzel from the wolves in the woods (literally and figuratively), delivers the show’s thesis in “Children Will Listen.” And if you’re a founder who mentors other founders, who runs an accelerator, who advises startups, who shapes economic development policy for a city, you need to sit down and actually absorb what Sondheim is saying in this song.
“How do you say to your child in the night, nothing’s all black, but then nothing’s all white? How do you say it will all be alright, when you know that it mightn’t be true? What do you do?”
What do you do? What do you tell the first-time founder sitting across from you at office hours? Do you tell them the truth, that 90% of startups fail is misleading but the actual odds are still brutal? Do you tell them that the average age of successful founders is 44, which means if they’re 23, they’re statistically playing against the house? Or do you tell them what’s nice? Do you nod and smile and say, “Great idea!” because being encouraging is easier than being honest?
“Careful the things you say, children will listen. Careful the things you do, children will see and learn.”
The ecosystem builders, the accelerator directors, the government officials allocating innovation budgets, the VCs writing Medium posts about product market fit when they don’t even know how to find it; these are the adults in Sondheim’s metaphor. The founders are the children. Not because founders are childish but because they are, by definition, entering the woods for the first time. They will listen to what you tell them. They will model what you show them. They will internalize the stories you tell about success and failure, and those stories will shape whether they survive. Sondheim lyrics warn: “What do you leave to your child when you’re dead? Only whatever you put in his head. Things that your father and mother had said, which were right for they, too.”
Some of us have been explicit about this problem for years: governments keep insisting they’re “supporting entrepreneurship,” yet the tools they fund are usually the bureaucratic equivalent of a pep rally. Innovation hubs with free Wi-Fi, pitch competitions, and motivational speakers who read the same three startup books as everyone else. These things create the appearance of activity but deliver outcomes only for the handful of founders who already know how to navigate. The rest? They listened. They heard “build it and they will come.” They heard, “quit your job and be an entrepreneur.” They heard “you need to be in an accelerator,” without any context of which one, if it’s any good, and how it will help them. And they acted on it, because children will listen.
“Children may not obey, but children will listen. Children will look to you for which way to turn, to learn what to be.”
The Witch distinguishes between listening and obedience. The best founders don’t obey their mentors; they shouldn’t (adherence in entrepreneurship is death by committee), but they do listen, absorb, and internalize the perspective they’re given. They question! When the advice is garbage (pitch competitions as validation, vanity metrics as traction, disregarding marketing because you’re not ready), the founders who listened build companies that reflect the garbage they were taught. As I’ve explored in why startups (and startup ecosystems) fail to gain traction, most of fail because your narrative doesn’t build trust, urgency, or credibility. And that’s because no one taught you how narrative actually works; they taught you a pitch template, and they taught that because it’s all they know.
Wishes Are Children
The most haunting of the finale comes not from the Witch’s solo but from the ensemble: “Wishes are children.” A wish, like a child, like a startup, is a living force that you set loose in the world, and it will take its own path whether you like it or not. A wish, Sondheim tells us, will “come true; not free.” Spells, tales, even casual words may linger past what you can see and turn against you. By equating storytelling with spellcasting, Sondheim shares the thesis I’ve been arguing for years: narratives shape reality. Media is capital. Your story is the spell you’re casting, and if you’re careless with it, it will turn against you.
This is why the comparison between Into the Woods and the founder’s journey isn’t cute or literary; it’s structural. The Baker and his wife undergo trials analogous to modern-day startup development in their quest to have a child (the startup equivalent of product-market fit: something alive that you made, that needs you, that will eventually outgrow you). Jack goes on a mundane errand to sell the cow (pivot the business model) and ends up meeting a pair of giants (the market opportunity is bigger than you thought) and stealing their gold (first revenue, validation, proof of concept). How can any of them not be profoundly altered by the experience?
And then Act II happens. Dreams fulfilled.
In Act II of Into the Woods, every character has gotten what they wished for. Cinderella married the prince. Jack has gold. The Baker and his wife have their child.
And everything falls apart.
The Giant’s Wife comes down the beanstalk seeking revenge, the princes turn out to be unfaithful (of course they do; they were “nice,” remember, not good), and the characters have to reckon with the consequences of the very wishes that drove them into the woods in the first place. From another song, American Pie and the Moment Every Founder Loses the Music: startups do not die from lack of effort, talent, or capital, they die because the conditions that made the music play in the first place were systematically dismantled by the very success the founders pursued.
“Careful the wish you make; wishes are children. Careful the path they take; wishes come true, not free.”
Every founder who has closed a funding round and then immediately felt the weight of dilution, board expectations, and the realization that the money comes with strings knows this feeling. Every founder who shipped a product, got initial traction, and then discovered that scaling requires an entirely different skill set than building knows this. Why do you think the conventional wisdom that investors want to replace founders was born? The wish came true, it was not free, and now you’re in Act II, where the Giant’s Wife is stomping around your formerly idyllic kingdom, and you have to deal with it without the Narrator (who gets sacrificed to the Giant early in Act II, because in the real world, the person who tells you the story is never the one who has to live with the consequences).
Tamper with What Is True
“Guide them, but step away. Children will glisten. Tamper with what is true, and children will turn, if just to be free.”
The instruction is paradoxical and meaningful to everyone in the startup ecosystem – advisors, investors, and founders, we don’t have the right answers! Guide but step away. Don’t hover. Don’t control. Don’t pretend you can manage the outcome. But also, critically, don’t lie. I like to advise but constantly saying to founders, “I have no idea what you should do, but I know what doesn’t work.”
“Tamper with what is true and children will turn, if just to be free.” The moment you sell founders a false narrative (that the Accelerator is right, that MVP-first is always right, that bootstrapping is romantic instead of the baseline it always was), they will eventually discover you lied, and they will turn. Not out of malice, but out of the basic human need for self-determination that psychologists Edward Deci and Richard Ryan identified in Self-Determination Theory: autonomy, competence, and relatedness drive sustained motivation. Tampering with truth undermines all three.
William Blake understood this two centuries before Sondheim staged it (yes, let me add another history lesson). Blake’s Songs of Innocence and of Experience, published in 1789 and 1794, challenged the dominant educational literature of his time, which emphasized moral lessons and cautionary tales. Blake asserted that children’s impulses were naturally good, but that the admonishment to “be good” often meant squelching those impulses in the name of conformity. Cinderella asks the same question in the show’s opening number: “What’s the good of being good if everyone is blind?” The startup equivalent is the entrepreneurial personality, the 8% who can’t not do what they do, being told to write a business plan, find a co-founder, validate the market, apply to an accelerator, follow the template.
What’s the good of following the template if the template was never designed for how you think? What good is it if it doesn’t work?
Blake’s Witch equivalent, the Nurse in “Nurse’s Song” from Songs of Experience, watches children at play and projects her own disillusionment onto them: “Your sun and your day are wasted in play, / And your winter and night in disguise.” That’s the VC who’s been stung too many times and now only funds safe bets. That’s the ecosystem leader who insists on “proven models” because they’ve confused risk aversion with wisdom. The Witch in Into the Woods has the same impulse; she wants to protect Rapunzel from the wolves. “Stay a child while you can be a child.” But the song knows better: children will listen, and if what they hear is fear, they’ll either obey it (and never go into the woods at all) or rebel against it (and go in completely unprepared).
Blake’s most relevant poem for founders is “A Poison Tree.”
“I was angry with my friend; I told my wrath; my wrath did end. I was angry with my foe: I told it not; my wrath did grow.” The poison plant grows, fed by false smiles and crocodile tears. Every founding team that avoids hard conversations about equity, roles, vision, and values, is growing a poison tree. Every accelerator that gives positive feedback to avoid uncomfortable truths is growing a poison tree. Every ecosystem that celebrates starts without measuring outcomes is growing a poison tree. Blake never used the word “nice,” but he would have recognized its toxicity immediately.
Careful Before You Say “Listen to Me”
Sondheim’s final instruction: “Careful before you say, ‘Listen to me.’ Children will listen.”
That line should be tattooed on the forearm of every person in the startup ecosystem who presumes to advise, invest in, or build policy around entrepreneurs. You have no idea how much weight your words carry to someone in the woods for the first time. You think you’re having a casual office hours conversation; they think you’re the oracle. You think you’re offering one perspective among many; they think you’re telling them the truth about whether their startup will work. And if you’re wrong, if your framework is outdated, if your experience is from a different era or sector or geography, they will build on the foundation you gave them, and it will crack, and they will not blame you. They’ll blame themselves because children will listen.
I am guilty of this. Every advisor is. The number of times I’ve held office hours with founders who push back with certainty on my feedback, is astounding. But the ones who don’t push back worry me more, because they took what I said and treated it as gospel, and I’m not gospel. I’m one voice. The most dangerous thing in the startup ecosystem isn’t bad advice; it’s advice delivered without the caveat that it’s just one person’s perspective. “Careful the tale you tell; that is the spell,” Sondheim equates storytelling with spellcasting because both have the power to bind. The narrative you give a founder becomes the architecture of their company.
If the story is wrong, the building is wrong.
Blake’s The Tyger asks the question that every founder eventually faces: who made this? Who is responsible for the ferocity and beauty of what you’ve created? “Tyger Tyger, burning bright, In the forests of the night, What immortal hand or eye, Could frame thy fearful symmetry?” In interrogating the Tyger about its origins, Blake asks what might never arise outside the woods. The theater, stories, are one frame for that. So is a startup. So is a city’s startup ecosystem. So is a founder sitting in a garage trying to make something out of nothing. It’s only explored in the woods where lives intertwine, stories come together, and children learn about wolves and dreams coming true.
Into the Woods, but Mind the Past
The great genius of Into the Woods is that it allows us to be at once inside and outside the woods, to give ourselves for a time within while returning home braver and wiser. Blake’s Book of Thel follows a young girl permitted to visit the underworld “to enter and to return,” in this tradition of classical heroes. She shrieks and retreats. A debate continues whether her retreat represents wisdom (refusing to enter a cycle that will consume her) or immaturity (refusing to take the risk of living in the real world). Every would-be founder who attends a startup weekend, reads a few books, talks to a couple of VCs, and then goes back to their corporate job has had a Thel moment. Maybe that’s wisdom. Maybe it’s fear.
The thing is that the woods don’t judge.
For those who stay in the woods, who keep going after Act I’s wishes have been granted and Act II’s consequences have arrived, Sondheim offers the Baker.
The Baker loses his wife. He loses the Narrator, most of the community’s infrastructure, and he’s left holding a child (the startup, the mission, the thing he wished for) with no instructions. What does he do? He tells a story. He sits down and begins: “Once upon a time…” Because stories are the only infrastructure that persists after everything else collapses.
Founders aren’t just solving problems; they’re reframing reality. They’re worldbuilders. And the ones who fail are usually the ones who build a product without ever building belief.
“Into the woods, then out of the woods, and home before dark.”
That’s the wish but reality is messier; you go into the woods and the woods change you. Home doesn’t look the same when you return because you’re not the same. You know things now that you never knew before. And the people who stayed home, who watched you go and worried and waited, they won’t understand what you saw. They can’t. They weren’t there.
But if you’re lucky, if you’re honest, if you’ve survived the Giant and the Wolf and the princes who turned out to be charming but not good, you get to do something the fairy tales never cover: you get to tell the story to the next person heading into the woods. And when you do, for the love of everything you’ve learned, be careful. Careful the things you say and careful the things you do because children will listen. They will look to you for which way to turn, to learn what to be. And the spell you cast with your tale, whether it’s a pitch deck template, an accelerator curriculum, a government innovation policy, or a quiet word at office hours, the spells don’t expire when you leave the room.
Sondheim and Blake knew, the question that struck me hearing the song Children Will Listen again, is whether we do.
Wondering whether to go into the woods or stay where it’s safe? I can’t answer that for you. Nobody can. But I can tell you this: the woods are where you find out what you’re made of. They’re where nice gets separated from good. They’re where wishes come true but not free. And they’re where you discover, maybe for the first time, that the most dangerous thing in the forest was never the Wolf or the Giant. It was the story someone told you about who you were supposed to be.
