It was another day of meeting aspiring founders and hearing out their fundraising journey. The story that I am about to share today is an especially memorable one as we spoke right before his planned “sparring” sessions (as he puts it) with some out of town investors. What inspires me the most with this founder was that he embraces the rejections in fundraising and knows that every rejection will eventually lead to a yes.
The Pitch
Let’s call the founder, Brad (pseudonym). Brad was planning a trip up north to meet several potential investors with hopes to get some preliminary feedback and in the same time improving his existing pitch deck. He runs an asset light startup that puts SMEs on the digital map to connect clients to businesses. Brad was enthusiastic and possess the technical knowledge to bringing the idea to life. MVP was ready and having done his homework on pitch decks, Brad showed me his 10 slides pitch deck. The flow was Problem-Solution-Business Model- Team layout and showed that he was well rehearse with FAQs and addressing some questions that may arise during the pitching session.
Here’s what I loved about Brad’s approach. He embraces potential rejections to prepare for bigger and more sophisticated question and pitching. I love the fact that these preliminary pitching rounds were treated as sparring sessions. In my earlier days as an investment adviser, we had mock presentations in office with more seasoned advisers to improving our presentation, objection handling and thinking on our feet with questions that caught us off guard. In those “sparring sessions”, we were slowly being introduced to difficult clients and taught how to handle “curve ball” like questions during presentations. What Brad is currently doing reminded me of that journey.
Here’s the downside to it, while we had a long list of investors (retail and sophisticated) to meet and get referrals from, Brad’s list of investors interested in startup investing may be significantly shorter. This was later revealed when I asked how long was his list of investors. While it is good to keep a positive and always keen to learn attitude to pitching, it would be better if he aimed to close instead of aiming to fail and be rejected. So here’s how I broke it down: 1) Aim to close during the pitching session; 2) Be prepared to be rejected or face tough questions.
You fall to your highest preparations. - Chris Voss

What I Suggested
During Brad’s pitching, he was introducing several potentials that were good but weren’t in the deck. When asked, he and his cofounder had a sudden realisation that the potentials were left out unintentionally. In order to make it short (in no. of slides) they made a decision to cramp information that was relevant into the deck. It was a common practice (and mistake) that I have made as well. Instead of paraphrasing or rewording the captions/title/text to be concise, information were cramped into the slides and made it look cluttered.
The Founding Team
Like I explained earlier in this newsletter, Brad had the technical knowledge and even work experience to bring this project to life. He held technical position for a local startup that tackles a different sector, with that knowledge he knew what it takes technically to make the system work. It was unintentionally left out as he felt at this point it was too lengthy. I explained that from my interviews with several VCs, that information is actually crucial.
What’s Important To Note
From the encounter, it is important to note that when you’re trying to make your deck concise, it isn’t just a matter of pasting existing information from two slides into one, sometimes rewording it will help with the information flow. More importantly, don’t aim to fail, aim to persuade but prepare for the worst.
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