Let me share a little insider secret: even the founders of multimillion-dollar enterprises are winging it sometimes. Coming into my role as an executive assistant, I had certain expectations—okay, let's be real, I had sky-high expectations about the kind of superhumans I'd be working with. I imagined these founders as these otherworldly beings, privy to the covert knowledge that kept them leagues ahead of us mere mortals.
Spoiler alert: that's not exactly the case.
Having a backstage pass to the inner workings of leadership has been eye-opening, to say the least. I've sifted through the correspondence of the top brass, been a fly on the wall at their meetings, and there have been plenty of "Holy Shit" moments when revelations struck about what they didn't know.
This behind-the-scenes view has been nothing short of a revelation. It's peeled back the curtain and revealed that these business demigods I put on pedestals are just regular folks. Folks who might bring a bit more grit and endurance to the table, reaching heights of success that I've admired from afar.
At times, it felt as though I was regarding them like royalty—distant, enigmatic, chosen by some divine right. Nothing could be further from the truth. The candid insights I've gained from these founders have only cemented the understanding that, at our core, we're all navigating the choppy waters of the human experience together.
The nagging question that’s been eating at me—and yes, this definitely stems from my own limiting beliefs—boils down to this: 'How have they made it this far and made so much money?' ( Full disclosure: When I hear "multimillions in revenue," my brain goes straight to, "Damn, you've officially made it.")
Here are a few choice snippets from what I've seen up close. But before I dive in, let me lay down this important caveat: I’m not here to discredit anyone, nor am I exposing any real names or businesses. The truth is, I’m more annoyed with myself for harboring these assumptions and doubting my own abilities for so long.
When Founders Get Tripped Up by Metrics
Take *Sabrina—she's the brains behind a booming business, yet there’s a gap in her armor: a firm grasp of the hard numbers.
"You'd laugh if you saw my spreadsheets," she jokes, "No clue if I'm even reading them right."
She's wading through daily operations with a 'figure-it-out-later' attitude towards the metrics. Whenever the topic of a target cost or a booked call comes up, it’s a shrug and a quick "I got nothing."
"It's like this constant background noise," *Sabrina confesses.
She's in meetings nodding at numbers, her internal monologue jokingly asking:
"Is that number a high-five or a cry for help?"
Her experience isn't unique. She represents many founders who can strategize and innovate but get lost in the sea of analytics.
"People say 'identify the problem,’ and I’m here like, 'How can I fix what I barely comprehend?' Marketing metrics feel like they're in another language."
*Sabrina's story is that of a visionary who'd rather stick to the bigger picture than get bogged down by details she's sure others can handle.
"Why deep-dive into the weeds if I’ve got people for that?" she says, half-questioning, half-stating her preference for delegation over digging into the data herself.
The Downside of Detachment: When Outsourcing Backfires
Setting the Scene: Envision a high-rolling business, raking in millions decides, "Hey, let's outsource our heart and soul," aka marketing and sales, to two different external agencies. To add another layer, their sales force is made up largely of part-timers.
There's a glaring issue here that's as big as a billboard: these folks have zero skin in the game. The founders, bless their hearts, have unintentionally cultivated a culture that screams 'commitment issues.'
Then came the day everything imploded. Here's the tea from *Gina and *John:
“They walked out with all of their collateral. They just packed up their things and left, taking every bit of their work with them."
"Next thing we know, we're locked out of our own systems. So here we are, back to the drawing board, trying to rebuild our systems from scratch."
"We're huddled around a call, trying to piece together the scripts, and they’re like, 'Oh, we did those at the Bootcamp.' And we're thinking, 'What about all the new stuff we needed?'"
"And the guy who's helping us out with our processes says, 'That's actually the most crucial part.'
We nodded along, knowing full well with everything collapsing on so many fronts, we're left guessing what hill to die on without them."
*Gina and *John's tale serves as a real wake-up call for any business playing fast and loose with outsourcing. They watched their company's lifeline walk right out the door, leaving chaos in their wake. It's a stark reminder that while hiring part-time pros might seem like a savvy move, it can quickly backfire if they're holding all the cards. Invest in folks who stick around, because they're the ones who keep the whole ship steady.
Ineffective Sales Tactics and Poor Product Understanding
Diving into the sales tactics of three distinct clients, it's a head-scratcher how they're hitting the million-dollar revenue mark. They're practically tripping over themselves—downselling premium options, bailing on calls due to prejudged lead quality, and the icing on the cake? A muddled understanding of their own product offerings.
Client A: Prioritizing Low-Value Products Over Premium Options
Client A is in a perplexing situation of converting potential $12K sales into mere $2K ones. It's baffling to see founders obliviously steering high-value leads towards the bargain shelf. These prospects are ready and able to spring for the top-tier products, which not only suit them better but also rake in triple the profit compared to the budget options being peddled.
Client B: Empowering Sales Reps to Dismiss Quality Leads
The phenomenon of sales reps dropping calls like they're hot potatoes is absurd. They're sidestepping opportunities for big-ticket sales worth 25K in favor of pushing 3K offers. Why? This misstep stems from a misplaced empowerment by the founder, who allows sales staff to judge and dismiss leads based only on preliminary online applications—without a real conversation. This leads to a swath of missed opportunities, even as the company astonishingly pulls in $1M per month.
Client C: The Product? A Mystery Even to the Sales Squad
They've got two sales reps in the ring, closing deals without laying down a proper pitch. Decision time for buyers can drag out from weeks to years since both the individuals closing deals and those tasked with initial contact lack a fundamental understanding of what they're selling. This not only hinders the sales process but dramatically impacts the potential for converting inquiries into actual sales.
A Humble Google Doc Piloting a $12M Business
Venturing into the realm of a multimillion-dollar entrepreneur, I encounter *Chet, a prodigy who made a fortune just shy of his 21st birthday, and oversees a business of around 20 people —all with zero clues about traditional bookkeeping.
A snippet of real chatter:
C: What do they actually do, bro? (yes, he calls me bro.)
E: They do bookkeeping. Lol
E: They get your numbers straight, shoot over profit and loss statements, get you ready for tax season, break down your spending... the whole nine.
E: Wait a minute...Are you telling me you've been operating without any bookkeeping? Just running a $12M/yr empire off a damn Google doc?
*Chet's candid confession: "Never done bookkeeping ever before. It’s different in *my country.”
This is the true definition of learning as you go. Makes you wonder, doesn't it? What the hell is holding you back?
Final Thoughts
I used to think founders and CEOs had all the answers, possessing a secret blend of innate wisdom or accumulated savvy. Yet, the deeper I delve, the more it becomes apparent that the secret sauce isn't knowing everything—it’s knowing your one true strength and owning it completely.
As for the rest? Well, they're content to acknowledge it as out of their depth, a language they don't speak fluently. Their magic trick? They recruit aces in those unknown fields to fill in the gaps, creating a well-oiled machine that thrives on collective expertise.
Between my successes and my failures, I find the real narrative of human experience: we're all just figuring it out as we go.
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