Hey founders,
Welcome to another edition of My Unicorn Club - The Startup Newsletter - It’s a biweekly FREE newsletter written by those on this side of the table (VCs & Investors) for those on that side (Founders & Startup Enthusiasts).
From scaling a diet-based meal delivery startup to leading a robotics accelerator across India and Southeast Asia, I've seen firsthand what it takes to turn ideas into execution.
I understand how frustrating it can be to be raising funds for the first time. Keeping the ray of hope alive amidst the inbox full of rejection.
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The $100 Million Question Nobody Can Answer
Picture this: You're sitting across from a VC who thinks your pre-revenue startup is overvalued at $5 million. But your competitor down the street, with a similar idea and no customers either, just raised at a $15 million valuation.
Welcome to the wild world of startup valuation—where traditional rules don't apply, and everyone's making “educated guesses” with million-dollar consequences.
Here's the uncomfortable truth: Most evaluators are using shortcuts, gut feelings, and flawed math to decide your company's worth. And as a founder, understanding this gap isn't just helpful—it's essential for your survival.
Why Traditional Valuation Breaks Down for Startups?
When Professor Aswath Damodaran—widely regarded as the "Dean of Valuation" at NYU Stern—tackles startup valuation, you listen. This is the man who's valued everything from Apple to Uber, and his insights into early-stage companies reveal why most investors get it wrong.
Traditional companies are easy to value. They have revenues, profits, and comparable public companies. Startups? They have dreams, assumptions, and a PowerPoint deck.
Consider these sobering statistics:
90% of startups fail within their first five years
Only 1% of startups become unicorns (valued at $ 1 B+)
Less than 40% of startups ever achieve profitability
Yet somehow, we're supposed to put precise valuations on companies that statistically won't exist in five years.
First, we will talk about the problem.
5 Fundamental Flaws in How VCs Value Startups
1. The DCF Delusion: "It's Impossible, So We Won't Try"
The Problem: Most VCs claim you can't use Discounted Cash Flow (DCF) models for startups because there are no cash flows to discount.
The Reality: DCF is not only possible—it's essential when adapted correctly.
Damodaran argues you can forecast cash flows using two approaches:
Top-Down Approach: Start with TAM
Let's say you're building a food delivery app:
Don't say: "Food delivery is a $150B market, we'll get 1%"
Instead, say: "In our city, people spend $50M annually on takeout. We can realistically capture 2% in Year 1, growing to 8% by Year 3 as we expand to 3 neighboring cities.
Bottom-Up Approach: Build from operational capacity
Be honest about what you can actually handle:
"With our current 5-person team, we can onboard 50 restaurants per month."
"Each restaurant averages 100 orders monthly, at $3 commission per order.r"
"That's $15,000 monthly revenue with our current capacity."
"With $500K funding, we hire 10 more people and triple our capacity."
2. The 60% Discount Rate Deception
The Flaw: VCs often discount projected 3-year revenues at 60-70% annually to arrive at current valuations.
Here's how this typically works:
Startup projects $20M revenue in Year 3
VC applies a 60% discount rate
Voilà! Current valuation of $3.2M
Why This Is Dangerous: This isn't valuation—it's negotiation disguised as math.
A 60% discount rate implies:
Ignores the upside potential that makes startups attractive
No consideration for different risk profiles across industries
The Better Approach: Risk-adjust your assumptions, not your discount rate.
Use market-appropriate discount rates (12-20% for most startups)
Model multiple scenarios: pessimistic, realistic, optimistic
Weight these scenarios by probability
3. The Terminal Value Trap: Where 90% of Your Value Lives
Fact: For most early-stage startups, 90 %+ of their valuation comes from terminal value—what the company will be worth years from now (typically 5 or 7 years)
This makes your assumptions about long-term survival and success absolutely critical.
Example Breakdown for a Typical Series A Startup:
Years 1-5 cash flows: 8% of total value
Terminal value (Year 6+): 92% of total value
This means the difference between a $10M and $50M valuation often comes down to assumptions about:
Market size in 5-7 years
Your competitive position at maturity
Exit multiples in your industry
Implication? Spend more time modeling your long-term competitive advantages and market evolution, not just your next 18 months of expenses.
4. The Equity Equality Myth: Not All Shares Are Created Equal
The Misconception: 10% equity is 10% equity, regardless of when you get it.
The Reality: Equity value depends on liquidation preferences, voting rights, and control terms.
Consider this cap table scenario:
Founder: 70% common stock
Series A: 20% preferred stock with 1x liquidation preference
Series B: 10% preferred stock with 1x liquidation preference
If the company sells for $10M:
Series B gets: $1M (their money back first)
Series A gets: $2M (their money back next)
Founder gets: $7M (what's left)
But if it sells for $100M:
Series B gets: $10M (10% of total)
Series A gets: $20M (20% of total)
Founder gets: $70M (70% of total)
The Lesson: Understand liquidation preferences, participation rights, and anti-dilution provisions. They can dramatically affect your actual ownership economics.
If not clear yet? You can read in detail here
5. The Relative Valuation: Comparing Apples to Rockets
The Mistake: Using P/E ratios or EV/Revenue multiples from public companies to value early-stage startups.
Why It Fails: Public companies have:
Proven business models
Predictable cash flows
Established market positions
Lower risk profiles
A Better Framework for Relative Valuation:
Compared to companies at similar stages, not similar industries
Look at revenue per employee, customer acquisition costs, and unit economics
Factor in market size and growth rates
Consider the quality of the founding team and early customers
How Smart Investors Actually Value Startups?
Based on Damodaran's methodology and real-world investor behavior, here's how sophisticated valuation works:
Step 1: Scenario Planning (Not Point Estimates)
Instead of saying "We'll hit $10M revenue in Year 3," model:
Bear Case (30% probability): $3M revenue, high churn, tough market
Base Case (50% probability): $8M revenue, steady growth, normal competition
Bull Case (20% probability): $25M revenue, viral growth, market leadership
Step 2: Risk-Adjusted Cash Flow Modeling
For each scenario:
Model actual cash flows (revenue minus all expenses)
Include working capital requirements and capex needs
Factor in different funding requirements and dilution
Step 3: Terminal Value with Multiple Exit Paths
Consider different exit scenarios:
Strategic acquisition (typical 3- 5x revenue multiples)
Financial acquisition (based on EBITDA multiples)
IPO path (public market comparables)
Failure/wind-down (asset recovery)
Step 4: Monte Carlo Simulation
Run thousands of scenarios with different:
Market growth rates
Competitive dynamics
Execution timelines
Funding requirements
This gives you a distribution of outcomes, not a single point estimate.
What This Means for You as a Founder
1. Build Your Own Model
Don't rely on investors to understand your business better than you do. Create detailed financial models that show:
Unit economics at scale
Path to profitability
Sensitivity to key assumptions
Multiple exit scenarios
2. Tell a Coherent Story
Your valuation should connect to:
Market opportunity size and growth
Your unique competitive advantages
Realistic timeline to profitability
Clear exit strategy
3. Understand Your Deal Terms
Valuation is just one component. Pay equal attention to:
Liquidation preferences
Anti-dilution protection
Board control
Drag-along and tag-along rights
4. Focus on Value Creation, Not Just Valuation
Remember: A higher valuation today means higher expectations tomorrow. Focus on building a business that can grow into and beyond its valuation.
The Bottom Line: Valuation Is an Art Built on Science
Startup valuation will never be as precise as valuing IBM or Coca-Cola. But it doesn't have to be random guesswork either.
By understanding these frameworks, you can:
Have more informed conversations with investors
Make better decisions about funding offers
Build financial models that actually help you run your business
Avoid the common pitfalls that kill promising startups
The next time a VC throws out a valuation, you'll know what questions to ask and what assumptions to challenge.
Remember: Your startup's value isn't what an investor says it's worth—it's what you can build it to become.
Want to dive deeper? Check out the Fundraising Kit.. Also, let me know what you would like me to add to the kit
Get the complete Fundraising Kit here
Until next time, signing off
Sayanee Bhowmik
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I really appreciate this kind of Information. Literally I've self funded every business, or reached out to just a small group of people I've known, because the schools don't teach this ind of stuff. and its a shame. Shark Tank just say, helped me along the years to understand certain terms, and my brain helps me learn more. But I'm all here fro this kind of information. I truly Appreciate this and look forward to reading, learning, and absorbing more.
Thanks