Aaron Vaccaro is the Managing Director of WestRiver Group, where he runs portfolio companies Singularity University and Liquor Lab.
Raising capital is a rite of passage for most entrepreneurs, but it’s also where many brilliant founders stumble. As an investor, I’ve sat through hundreds of pitches—some inspiring, others forgettable. What separates the memorable from the mediocre isn’t just a killer product or the size of the market. It’s how founders tell their story, build trust and navigate the delicate dance of asking someone to bet on their vision.
Yet, time and again, founders make the same mistakes. Here are the five biggest missteps I see in pitch meetings and how to avoid them.
Mistake #1: Pitching A Product, Not A Business
A great product is critical. But a great company is more than just a product—it has a purpose and a business model.
Investors want to hear:
• How will you consistently and profitably acquire customers?
• What does the road map look like if the first product is successful?
• What is the big vision that, if achieved, will drive a massive return?
Your investors are buying into a business, not just an invention.
Mistake #2: Ignoring The Competitive Landscape
One of the quickest ways to lose credibility in a pitch is by saying, “We have no competitors.” Savvy founders:
• Know their direct and indirect competition
• Understand their competitors’ weaknesses
• Articulate their unique moat, aka business advantage, with clarity
Investors don’t expect a competition-free market. They expect you to have a strategy to win market share.
Mistake #3: Overhyping Market Size Without A Clear Wedge
Yes, investors love a large total addressable market (TAM), but what they love even more is a founder who knows where to start.
Claiming you have a $50B TAM is meaningless if you can’t explain:
• Who your early adopters are
• How you’ll expand from a niche into a broader market
• What percentage of the market you need to be successful
Start small, show how you’ll win your initial niche, and then paint the vision for scale. That’s a much more believable growth story.
Mistake #4: Being Too Polished Instead Of Personable
It’s good to be prepared, but I’ve seen pitches that feel over-rehearsed, like a corporate sales deck. Investors want to invest in people, not presentations.
Be human. Share:
• Why this problem matters to you
• What drove you to build this company
• The lessons you’ve learned from early failures
Vulnerability builds trust. Investors don’t expect perfection; they want to bet on founders who are self-aware, coachable and relentless.
Mistake #5: Failing To Answer ‘Why Now?’
One of the most critical questions in any pitch: Why now?
• What market shifts or emerging trends make this the perfect time for your solution?
• Is there a technological inflection point?
• A behavioral change in consumers?
• Regulatory changes opening up the market?
Founders who can’t clearly articulate why their startup is urgent often lose momentum with investors. Being too early or too late is the same as being wrong.
The Bottom Line
Investors are not looking for the flashiest deck or the loudest hype. They are looking for founders who deeply understand their business, their market and their moment.
As a founder, your job isn’t to sell an investor. It’s to invite them into a shared vision and give them the confidence that you’re the right one to build it. Get this right, and you’ll find the right investors leaning in, not tuning out.
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