Startup War Stories: A Field Guide to Surviving Entrepreneurship
By Samson Williams
Every would-be entrepreneur is like an 18-year-old headed to war. If they skip boot camp, they die almost immediately upon deployment. The battlefield doesn’t care about your idea—it cares whether you’re prepared to survive. Below is a brief description of who and types of Founders / Entrepreneuers and ecoystem players that will be encountered when starting a business. Much like G.I. Joe said, "Knowing is half the battle." So the question becomes, how are you training to become a Founder? And then, "Will that training help you survive the 97% mortality rate that is entrepreneurship?
Bootstrappers
They’re the resistance. Living off rationed ramen and YouTube tutorials. Building bombs out of code, prayer, and time. Their currency is sacrifice. Their reward? Survival.
Black Founders
Black Founders are the infantry. Deployed to the front lines with no gun, no armor, no ammunition—just the grit of our life-learned survival skills. We're told to “pull ourselves up by the bootstraps” while dodging bullets with no cover. Winning isn’t just building a business—it’s surviving the war.
Trust Fund Babies
They’re the West Point grads. Fresh uniforms, no field experience, reading books about war as they lead troops into ambushes. They burn VC money the way green recruits burn through ammo—recklessly. They’ll bankrupt one startup after another and call it "learning."
Venture Capitalists
VCs are the arms dealers. They don’t fight—they fund. They sell weapons, back both sides, and declare victory based on who gets acquired. When a startup dies, it’s the founder’s fault—not the faulty map they were given.
Angel Investors
They’re the rogue special ops. Veterans of past wars who drop in alone, with just enough cash, experience, and firepower to turn the tide of a losing battle. They choose missions based on instinct. Sometimes, they save the day. Other times, they disappear into the fog.
Accelerator Programs
Two-week guerrilla boot camps. You're taught how to stab a tank with a pencil, handed a pitch deck, and pushed out of a helicopter. Good luck. Hope your team survives the landing.
Pitch Competitions
Beauty pageants in a war zone. Founders are judged on their smiles, stories, and soundbites. Cry on stage and maybe someone hands you a grant instead of a grenade.
Tech Bros from Stanford
They’re drone pilots. Dropping “disruption” from 10,000 feet via code. They've never seen the carnage on the ground. They build apps, not trenches.
Black Women Founders
The true multi-role commandos. Medics, strategists, captains—all in one. Expected to heal, lead, fund, and endure, all while being told they’re “too aggressive” for asking for air support.
Crowdfunding & Crowdfunding Investors
Crowdfunding is the village under siege passing a helmet around. Every dollar counts. Crowdfunding investors? They're the militia. Civilians with $50 and a dream, throwing in what they can because they believe. Not in the exit, but in you.
Private Equity Firms
The occupying force. They roll in after the smoke clears. They don’t innovate. They consolidate. They don’t care how many died, only what’s left standing. They’ll gut the buildings, sell the weapons, and lease the battlefield back to the next batch of founders.
Hedge Funds
They’re the warlords. Watching from mountaintops with binoculars and betting on which side will lose the most men. They profit from the carnage. They short your dreams and buy your ashes. They don’t need you to win—they just need to know when you'll fail.
Final Orders
Entrepreneurship isn’t a tech trend. It’s a war of attrition. And if you’re a Black or Brown founder, you’re not just fighting a market—you’re surviving a minefield. You’re the soldier, the medic, the cook, and the general.
Train accordingly.
Build your army.
Win your war.
Samson