And Why Your Next CEO Shouldn’t Be a Fortune 500 Star
There’s a persistent fantasy in the start-up world: the belief that bringing in a “seasoned” executive from a major corporation will instantly transform a fledgling business into a well-oiled machine. After all, they’ve run billion-dollar divisions, sat in polished boardrooms, and managed global teams. What could possibly go wrong?
Plenty.
While there are exceptions—executives who truly get it—more often than not, this move leads to friction, disappointment, and premature exits. Here’s why:
1. They Confuse Budget with Bootstrapping
In a corporate environment, problems are often solved by throwing money at them. Need a new product? Hire a consultant. Need talent? Poach with a big salary. Need traction? Spend on marketing.
In a real start-up—especially one that’s bootstrapped—there is no cushion. You need to solve problems with ingenuity, grit, and speed. That budget mindset? It’s a liability.
2. They’ve Never Truly Started Anything
Many of these “start-up savvy” execs claim they’ve built something from scratch—usually a new business unit or product line within a massive organisation. Let’s be honest: that’s not a start-up. That’s building with a safety net, inside a well-oiled infrastructure, with legal, HR, IT, and brand credibility already in place.
Try doing it when no one knows your name, you can’t afford a lawyer, your prototype fails, and your credit card’s maxed out. That’s the real game.
3. They Lack Staying Power
Start-ups aren’t sprints—they’re punishing ultra-marathons. The hours are brutal, the stakes are personal, and success often comes slower than expected.
Corporate high-flyers are used to defined KPIs, quarterly bonuses, and resource-heavy teams. When things get murky—or messy—they often lose interest. You’ll hear a lot of “this isn’t what I signed up for.” Spoiler: it is.
4. They Confuse Management with Leadership
Managing a team of 500 with a playbook and a chain of command isn’t the same as leading 5 people through chaos, ambiguity, and existential risk. Start-ups need leaders who can sell the vision, build culture from scratch, and inspire belief when there’s nothing tangible to point to yet.
5. They Often Undervalue the Founding Team
Big-company execs can be dismissive. They may assume their way is better—because it’s been tested at scale. But what works at IBM or Google often breaks a start-up. Worse, they can demotivate founders, undermine the early culture, or ignore the instincts that birthed the company in the first place.
So, What Should You Look For Instead?
You want someone with scars. Someone who’s raised money, missed payroll, slept in the office, pitched with a half-baked deck, and kept going anyway.
You want someone who isn’t too proud to scrub the office toilet at 11pm before the investor walk-through.
You want someone with vision, humility, and fire. Not just a CV that looks good on LinkedIn.
Final Thought:
There’s nothing wrong with hiring experience—but make sure it’s the right kind. The wrong corporate exec can sink your start-up faster than a funding drought. The right founder-operator? They’ll walk through fire to get you to the next round.
Choose wisely.
The Tipping Point 