0/ After evaluating 200+ startups this year, I've been in some awesome and not so awesome pitches.
Here are the top 10 mistakes I see Founders make that routinely derail fundraising

Here are the top 10 mistakes I see Founders make that routinely derail fundraising



1/ “If we just get 1% of the market we’ll be a billion dollar company”
Most software markets are winner take all, or at least winner take most. Dominant companies have a flywheel on talent, capital, product.
Explain why you'll be a major player, not a passive participant.
Most software markets are winner take all, or at least winner take most. Dominant companies have a flywheel on talent, capital, product.
Explain why you'll be a major player, not a passive participant.
2/ Mistaken X for Y analogies - “We’re Peloton for Education”
If you’re pitching yourself as X for Y, make sure you understand X and Y intimately. These analogies often don’t work in practice because of business model particularities of X and industry dynamics of Y.
If you’re pitching yourself as X for Y, make sure you understand X and Y intimately. These analogies often don’t work in practice because of business model particularities of X and industry dynamics of Y.
3/ Too many facts, not enough narrative.
The best pitches are immersive conversations. Storytelling and narrative brings your business alive. It creates a discussion arc that pulls Investors in and creates opportunities for engagement.
The best pitches are immersive conversations. Storytelling and narrative brings your business alive. It creates a discussion arc that pulls Investors in and creates opportunities for engagement.
4/ Overweighting advisors, underweighting team
Your advisors don’t build the company. You do. Period. Too many Founders focus on the “impressiveness” of their Advisors as a shield to their credentials.
Credentials don’t matter. Traction, vision and your clarity of thought do.
Your advisors don’t build the company. You do. Period. Too many Founders focus on the “impressiveness” of their Advisors as a shield to their credentials.
Credentials don’t matter. Traction, vision and your clarity of thought do.
5/ Too much industry jargon, not enough common language
Investors are not all knowing. Trust me. Don’t assume your investors know the nuances of your space - simplicity is best when establishing a baseline.
As the discussion evolves, you can always go deeper.
Investors are not all knowing. Trust me. Don’t assume your investors know the nuances of your space - simplicity is best when establishing a baseline.
As the discussion evolves, you can always go deeper.
6/ Introducing friction into the process
Non-standard practices (e.g. NDAs) stretch your fundraise cycle and make it more difficult to partner with you. Always focus on your north star - finding the right Investors as quickly as possible so you can get back to the business.
Non-standard practices (e.g. NDAs) stretch your fundraise cycle and make it more difficult to partner with you. Always focus on your north star - finding the right Investors as quickly as possible so you can get back to the business.
7/ A Flawed Competitive 2x2 Matrix
Your startup is in the upper right quadrant. But are your axes correct?
Helpful litmus test - If i asked your customer (and competitors) how they would draw up a 2x2 - what would they say, where would they put you and why?
Your startup is in the upper right quadrant. But are your axes correct?
Helpful litmus test - If i asked your customer (and competitors) how they would draw up a 2x2 - what would they say, where would they put you and why?
8/ Not enough focus on the business model
There are 4 components of a successful pitch:
Is this a big problem?
Do you have the right solution?
Is this a viable business?
Why are you the team to do it?
Investors are investing in a business - don’t forget that part.
There are 4 components of a successful pitch:




Investors are investing in a business - don’t forget that part.
9/ Not enough focus on the short term
Vision is necessary, not sufficient. Vision doesn't matter if you don’t survive the next 18 months.
Use the A-Z-B framework
A: This is where we are today
Z: This is where we want to be
B: $ will help us do BLANK to progress towards Z
Vision is necessary, not sufficient. Vision doesn't matter if you don’t survive the next 18 months.
Use the A-Z-B framework
A: This is where we are today
Z: This is where we want to be
B: $ will help us do BLANK to progress towards Z
10/ Setting expectations up front
The pitch is one piece of an overall process. Misaligned timelines and miscommunicated expectations lead to suboptimal outcomes.
In Meeting 1, understand - how much $ does this Investor typically invest? What does their process look like?
The pitch is one piece of an overall process. Misaligned timelines and miscommunicated expectations lead to suboptimal outcomes.
In Meeting 1, understand - how much $ does this Investor typically invest? What does their process look like?
11/ Bonus List
- Not knowing your metrics (and how you compare to other similar businesses)
- Underinvesting in your deck / memo (it’s a first impression)
- Leaving the energy at home
- Unclear roles between you / your co-founder
- Not being you! It's your time to shine.
- Not knowing your metrics (and how you compare to other similar businesses)
- Underinvesting in your deck / memo (it’s a first impression)
- Leaving the energy at home
- Unclear roles between you / your co-founder
- Not being you! It's your time to shine.