Desperation has a specific smell.
In the early days when my dad was building his security business, he walked into many a such meetings radiating it. He needed the cash flow. He needed the logo on my deck. He needed the validation. The client always smelled it. And because they smelled it, they owned him before he even opened my mouth.
When you are bootstrapping, sales isn’t about persuasion; it is about physics. If you lean too hard (Need), you lose your center of gravity (Leverage).
I recently dissected the sales philosophy of David Ogilvy. While most read him for copywriting, his real value was understanding the mechanics of agency warfare. He built a protocol that applies perfectly to anyone looking to build their business from the scratch
Here is how I have translated Mad Men theory into a bootstrapper’s blade.
The Sport of Detachment
When you treat a deal as “Life or Death,” your cortisol spikes. You talk too much. You promise features you haven’t built. You act like a lackey, not a partner.
The Fix:You must manufacture detachment.
Ogilvy advised regarding the hunt for a new client “as a sport.” If you win, you eat. If you lose, you learn the gap in your armor. But you do not bleed.
When I stopped trying to “close” and started trying to “diagnose,” my sales calls started improving. Clients trust a doctor; they ignore a beggar.
The Suicide Pact (The 30% Rule)
If one client makes up 50% of your revenue, you do not own a business. You are an undeclared employee with no benefits and high liability. When you cannot afford to say “No,” you cannot give honest advice. You become a “Yes Man.” And in the operations grind, “Yes Men” get crushed by scope creep.
The Metric: If a single client represents >30% of your revenue, you are in a danger zone.
Caveat: Early survival contracts are sometimes unavoidable. If you are at ₹2L MRR, a whale client keeps the lights on. The danger is pretending these contracts are strategy instead of temporary shelter. Treat them as a bridge, not a foundation. My current business was built on such contracts sourced in the start by my father. Currently I have exited most of such contracts as the customer keep asking for more at the same cost, assuming you are in the same situation
The Velvet Rope Strategy
When we start a new business, we consider selectivity is arrogance. “I’ll take anyone who pays!”
This is the fastest way to kill your operations. A bad client doesn’t just pay you money; they tax your attention. They are entropy. They demand 80% of your support tickets while paying 20% of your margins.
Ogilvy took “immense pain” in selecting clients because he knew that bad clients clog the machinery. Over the past 5 years, I
The Filter:
I use simple filters that are part of my operating principles
- Revenue Quality > Revenue Size
- Do they respect the system?
- Is the problem solvable with my specific skillets?
If the answer is No, I simple quote a exorbitant rate with limited credit period for payment, encouraging them to reach out to a competitor
The Purge (Fire to Survive)
Fire clients five times more than they fire you.
This is the hardest pill for a any new founder or small business owner to swallow. We are programmed to hoard revenue. But a toxic client is an infection. They demoralize your staff and force you to create “special processes” that break your standard operating procedure.
The Calculus:
I once fired a client paying ₹1.5L/month because their “emergency” calls were burning out my site supervisor.
- Short term:I lost revenue.
- Long term: I kept my employee, stabilized operations, and managed to find customers, who we could service with far better efficiency.
The Physics of Trust
In a market of “Game-Changers” and “AI-Powered Solutions,” honesty is the only disruption left. Ogilvy’s rule was simple: “State your flaws honestly.”
Don’t sell perfection. Sell the scar. Tell them:
- How much you charge
- Explain them how your service system work
- Explain them your payment terms
The wrong clients will run. Good.
The right clients—the ones who actually value you will sign up.
The Audit
Sovereignty is never given; it needs to be engineered.
Look at your client roster today. Identify the “Whale” that owns you and the “Vampire” draining your time. Draft the plan to replace them before they force the decision on you.