Cheerleaders vs. Boxing Coaches: Why the People Who Love You Are Killing Your Startup
Everyone loves a cheerleader.
They tell you they love you, your product rocks, and the world is going to beat a path to your door to buy it.
They do this because they want to support you and tangibly show they care.
Many of them are our friends and family, teachers and counsellors, and even the public in the form of likes and shares via social media.
These people are empathetic and genuinely want you to do well. They’re happy when you’re happy. But have you ever thought about it? They are dangerous. It is dangerous to be surrounded by people who care because they love you too much and overlook blind spots.
Knowingly or unknowingly, it usually doesn't end well.
The Problem with Cheerleaders
The problem with cheerleaders isn't their heart; it's their mechanics. Their lack of familiarity, expertise or understanding of market nuances (that insiders do) often mean the difference between life and death for your business. On top of that, they don't have the time—they're busy with their own lives. You aren't a priority. Instead of hard data, they smile and tell you to follow your dreams and your heart. But what if you're heading in the wrong direction? You'll just get to failure faster. It’s like a monkey encouraging a fish to climb a tree: “Just focus and work hard! One day you'll succeed. If I can do it, you can do it too.”
Maybe this is why more than 60,000 businesses folded in 2025. I wonder how many of them are 'backed' by cheerleaders.
So why are so many people so encouraging? Because it’s easier. Why should anyone risk offending you for nothing? It is far simpler to smile and say, "Just follow your heart," than to point out the fatal flaws in your business model. If you do make it, great! If you don't, not their problem.
The Empathy Trap: Where Does Cashflow Fit In?
These days, everyone stresses the desperate need for empathy, largely due to rising mental stress. The Cambridge Dictionary defines 'empathy' as: the ability to share someone else's feelings or experiences by imagining what it would be like to be in that person's situation
I have to wonder: How much does this apply in business, where cashflow is everything?
Cashflow is the fuel to a plane, oxygen to your lungs, and blood in your body. Without cashflow, nothing is real. Sales cures all.
Of course, one should have empathy—yes, toward your customers and your shareholders. These are your true benefactors who are keeping your company alive. But what happens when the lines blur?
Anecdotally, I’ve had the unfortunate experience of dealing with two startups that crumbled and became completely unaccountable. Both times, the CEO claimed he or she was feeling "depressed" and hence was unable to account to us. One went onto Facebook live to whine about how hard it is to deal with venture capital funds. Both had completely failed in their KPIs to the shareholders.
The question is: How much empathy should shareholders and customers provide to such CEOs?
To me, nothing is more important than health. Sort it out first. Business is just a tool. But next time, let the customer or investor know about your mental health issues BEFORE taking their money.
It’s like being a pilot and passengers on a commercial flight. The pilot has one job: to bring us home safely and on time. If you're depressed or "not feeling it," no issues—mental health is real, and we must respect that. But let me know before we are already 30,000 feet in the air! Thank you very much! Dropping the yoke because things got tough isn't a mental health strategy; it's a breach of fiduciary duty.
The Beauty of a Boxing Coach
This is why we need a boxing coach, not another cheerleader.
A real boxing coach doesn't give a damn about your excuses. They are laser-focused on prepping you for the ring.
They know that softness and delusion will get you bloodied. If you're not ready, they will push and scream at you to toughen you out.
Want to cry? Go ahead and cry, you crybaby. If you fold under pressure, you're not fit for the ring anyway. There are no participation trophies in business If you win the belt, it's because you earned it and you're worthy. If you're unfit, take your losses, go back to your cheerleader, and get her to make you a sandwich.
What is a Real Boxing Coach in Business?
A real boxing coach isn't a random critic shouting from the sidelines. They are someone:
who has been there and done that. Someone with a documented track record of success
who can connect you to the right networks, and most importantly—
who have skin in the game, often investing their own capital into your company.
Having a thick skin is a superpower in the startup trenches, and you need to start thickening yours immediately with a boxing coach. Cheerleaders make you soft. A boxing coach forces you to face reality.
If you want to survive the market, stop looking for applause. Find someone willing to tell you the unvarnished truth, step into the ring, and build a business that actually deserves to win. At the meantime, let me get my sandwich. ----------
Media contact: ian.gan@smaths.com
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