Christ. 3:17AM again. The glow of the laptop screen feels like it\’s burning holes straight through my retinas. Outside, the city’s finally quiet, or maybe my brain’s just too fried to register the usual sirens. Found another cold-brew coffee stain on my notebook – third one this week. This startup thing, man. They sell it like a revolution, like changing the world. Feels more like trying to assemble IKEA furniture in the dark while someone’s randomly shaking the box. And you lost the damn instructions years ago. Yeah, I’m Leo. The ‘Square Peg’. Got the nickname ’cause I kept trying to jam my weird-ass vision into rounds holes investors kept presenting. Still here. Still jammin’. Barely.

Remember pitching to that VC syndicate in that absurdly white, minimalist office? Felt like performing surgery on myself. Polished deck, practiced the damn ‘traction story’ until my jaw ached. One guy, slicked-back hair, expensive-looking watch that probably told the time on Mars, kept glancing at his phone. When I got to the unit economics slide – the messy, honest part showing how we might crawl towards profitability in 18 months if the stars aligned and a meteor didn’t hit – he actually sighed. Audibly. Like I’d farted in church. His feedback? \”Interesting vision, Leo. But the monetization pathway feels… unconventional. We look for cleaner narratives.\” Clean. Right. Translation: paint over the cracks, pretend the engine isn’t held together with duct tape and hope, and maybe we’ll toss you some crumbs. Felt like selling a piece of my soul just got a quote, and it was insultingly low. Walked out feeling smaller, dirtier. Questioned everything for days. Was I the delusional one? Maybe. Probably. Who gives a shit anyway.

Then there was Anya. Brilliant engineer. Could code her way out of a black hole. Hired her early, paid her mostly in ramen and promises. When we finally scraped together enough for real salaries, I offered her equity. Generously, I thought. Felt like a king bestowing a favour. She looked… disappointed. Not angry, just weary. Like she’d expected this stinginess. Took the offer, signed the papers. Found out six months later she’d been headhunted by a FAANG giant offering triple the salary, quadruple the stability, and actual health insurance that didn’t require sacrificing a goat. She stayed. Out of loyalty? Guilt? Or maybe just pity for the sinking ship captained by a fool. My ‘generosity’ was an insult. That one stung for weeks. Still does, sometimes, when I see her late-night commit messages. Taught me the hard way: loyalty isn\’t bought with table scraps disguised as treasure. People see through that. They deserve real skin in the game, or they\’ll find someone who gives it. My cheapness nearly cost me the only person holding the damn engine together.

And the product! Oh god, the product. Spent nine months building this feature. My baby. Convinced it was the ‘killer app’, the thing that would make users weep with joy. Complex backend, elegant UI, genuinely clever solution to a problem… that maybe twelve people on the planet actually had. Launched it with fanfare (well, a blog post and three tweets). Crickets. Then the support tickets started. \”Why is this so complicated?\” \”Where’s the simple thing I actually need?\” \”This broke my workflow.\” Felt like showing up to a potluck with a meticulously crafted, five-tier soufflé… only to find everyone just wanted chips and guac. Sat staring at the analytics dashboard, watching the flatline. The ‘product-market fit’ bullshit they preach felt like a cruel joke. We’d built a monument to our own cleverness, not to what anyone actually needed. Had to kill it. My beautiful, useless soufflé. Took a week off. Mostly stared at the wall. Ate cereal straight from the box. Felt like a failure. Still do, a bit. Now? Every feature idea gets screamed at by at least five potential users before a single line of code gets written. It’s messy, loud, and bruises the ego. But it beats building another damn soufflé for an empty room.

The loneliness is the weirdest part. Surrounded by people – employees, advisors, other founders at those awful networking drinks – and you feel utterly isolated. Can’t show the full panic to the team. Can’t admit the crippling doubt to investors. Can’t tell your partner you’re not sure you can make payroll next month again. You just… hold it. The weight settles on your shoulders like wet concrete. You smile, crack a joke about the ‘hustle’, and die a little inside. Saw a therapist for a while. Expensive luxury. She kept asking, \”Who’s supporting you, Leo?\” I’d just shrug. Maybe the ghost of Steve Jobs? My own stubbornness? The dwindling balance in the company account? It’s a solo hike through a damn blizzard most days. You just put one foot in front of the other because stopping means freezing solid.

They talk about ‘grit’ like it’s some noble virtue. Feels more like stupidity most days. Like banging your head against a brick wall because you’re convinced, deep down, this particular wall might eventually crumble. Maybe it’s just the sunk cost fallacy whispering sweet nothings. Maybe I’m too proud (or too dumb) to admit defeat. Saw a founder friend shut down last month. Smart guy, good product. Market just… didn’t care. The relief on his face, mixed with the grief, was terrifying. Part of me envied him. The escape. The end of the relentless pressure cooker. Another part of me, the stubborn, probably-masochistic peg part, recoiled. \”Not yet,\” it whispers, even at 3:17AM, staring at the coffee stains. \”One more brick.\” It’s not inspirational. It’s pathological. But it’s what keeps this creaky ship pointed vaguely forward.

So yeah. Essential advice? Ha. I barely know what I’m doing Tuesday. But if you’re another peg staring at a round hole world… maybe this helps. Or maybe it just confirms you’re as screwed as I am. Either way. Pass the cold brew. Got walls to bang my head against.

FAQ

Q: Seriously, when do I know it\’s time to raise VC money? Everyone says \”as late as possible,\” but how late is too late?

A: Ugh, the timing dance. \”As late as possible\” usually means \”once you\’ve proven people will actually pay you money for your thing, and you kinda know how to find more of them.\” Don\’t be like me, walking in with just a slick deck and a prayer. It\’s humiliating and wastes everyone\’s time. Too late? When you\’re choosing between payroll and the office coffee beans. Desperation reeks, and VCs have bloodhound noses. Raise when you have leverage – actual customers, real revenue growth – not when the wolves are literally at the door chewing on the power cord.

Q: How the hell do you handle co-founder conflict without imploding the whole thing?

A: Badly, mostly. Look, if you\’re not arguing, one of you isn\’t paying attention. The real killer isn\’t conflict, it\’s resentment festering in silence because you\’re both too damn tired or scared to address it. Rip the band-aid. Have the screaming match in the parking lot at 1 AM (not in front of the team, for god\’s sake). Get it out. Then figure out if it\’s a fundamental values clash (run) or just stress talking (talk more, maybe get a cheap mediator). Signed paperwork upfront (vesting, roles, what happens if someone quits or dies) is the only thing preventing actual murder later. Trust me.

Q: Obsessing over the product vs. chasing sales… how do you not suck at both?

A: You will suck at both sometimes. The key is knowing which one needs sucking less right now. Early on? Talk to users until your ears bleed. Build the ugly, barely-functional thing that solves one painful problem really well. Sell that. Use the money (and the feedback) to make it less ugly. Later, when you have actual customers yelling, the balance shifts. Ignore product bugs to chase a vanity enterprise deal? You\’ll bleed users. Ignore sales to tweak a button color? You\’ll bleed cash. It\’s a constant, exhausting triage. There\’s no magic balance, just constant adjustment and accepting that some days, both sides feel neglected.

Q: How do you deal with the constant, crushing self-doubt? Fake it till you make it feels like a lie.

A: Oh, the doubt\’s real. Anyone who says they don\’t have it is either lying or a sociopath. \”Faking it\” isn\’t about pretending you know everything (you don\’t). It\’s about projecting enough confidence in the mission to keep the team moving, even when you feel lost. Admit you don\’t have all the answers (\”Good question, I need to figure that out\”), but show unwavering belief in the problem you\’re solving and the team\’s ability to find the answers. The doubt? Channel it into obsessive customer validation. Let data (good or bad) quiet the demons, at least temporarily. And find one person you can be brutally honest with. A therapist, a scarred mentor, a bartender who doesn\’t care. Bottling the full crazy is unsustainable.

Q: When do you actually call it quits? How do you know it\’s not just a dip?

A: The million-dollar (or zero-dollar) question. If the core problem you set out to solve turns out to be non-existent, or your solution is fundamentally flawed despite multiple pivots? That\’s a strong signal. If you\’ve genuinely given it your all (proper runway, multiple strategies, talked to hundreds of users), and no one is willing to pay enough to sustain the business? Another signal. If the stress is literally destroying your health or relationships beyond repair? Listen to that. Dips feel scary but temporary. Quitting territory feels like an inevitable, grinding erosion. It\’s less about hitting a single low point and more about the complete absence of any upward trajectory, despite exhausting every realistic option. Trust your gut, but verify it brutally with data and trusted, unemotional advisors. Don\’t quit on a Tuesday because Monday sucked.