The Art of Pitching
10 guiding principles to help you create contagious conviction on pitch calls
As a founder, you know your product inside and out – but equally important is understanding yourself and why you're in the game in the first place. From my experience working with and coaching founders, I have found that the latter is where people struggle the most. In early stage venture, this is often the main reason why founders might miss out on a check from an investor they have been dying to work with—not because of doubts about the product, which investors expect to evolve—but because of a lack of conviction in the team behind it. You want to do the opposite: create contagious conviction that leaves the investor on the call wanting more, rushing to their computer to write a memo to pitch at their next Investment Committee.
During a pitch call, investors closely observe your non-verbal signals even more so than what you’re saying. They’ve probably seen the deck and are aware of what you’re trying to solve. So, what’s the purpose of the call? Vibes. How effectively are you communicating your passion and conviction? Are you demonstrating why you're the best person to solve the problem at hand? Building trust depends not only on your words but also on your genuine belief in what you're saying. Authenticity is key—it's about being yourself rather than adopting a sales persona.
During a pitch call, you're not just presenting a product; you're showcasing your best work and revealing your character. Drawing from experiences I’ve had with impactful founders, here are ten principles to guide your pitching toward more zeroes after that dollar sign:
10 Principles for Pitching
The Conversation Approach: Remember, investors are people too. They take many pitches every day, and the ones they remember are almost always a dynamic conversation as opposed to a lengthy presentation. If you go into every call with this mindset, you will start to break the founder-investor barrier sooner rather than later.
Read the Room: Pay attention to cues from listeners on the call. If you sense you're losing them, pause and ask if they want to continue or if they have any questions on the topic. It is a great way to temperature-check the investors’ interest and attention. Is your presentation getting too technical? Is your introduction too long? Channel your intuition in these situations and adapt to the energy in the room.
Create Healthy FOMO: Creating excitement is pivotal to running a successful round. An approach I have seen work well is to start by capturing the likes of angels and small funds you want to work with before approaching bigger players. This can help create a sense of exclusivity. Having solid commitments in place can signal to others that there is bite on the reel.
Timing is Everything: Avoid fundraising during industry downtime, such as after Thanksgiving or during the Summer. You want to create urgency by aligning your fundraising efforts with market opportunities. So, time this well!
Flip the Power Dynamic: Empower investors by inviting questions and engagement during your conversation. For example, ask them if they have questions about the materials you sent before the call (and yes, definitely send materials in advance). This allows for the chat to start as a back-and-forth discussion as opposed to a one-sided presentation.
Practice Crisp Communication: A clear problem-solution narrative is very effective. One mistake I see founders make is starting with a solution-product narrative. This can lead to losing sight of the problem and target customer(s) not only during the pitch but also into the build process. Simplicity wins. Remember to consciously practice delivering information in that manner.
Embrace Vulnerability: Be honest about your strengths and weaknesses. Demonstrating self-awareness builds trust and opens the doors to potential value add conversations on the investor side. It also shows incredible maturity to be able to identify and articulate what gaps you have and how to fill them. If you share that with the investor, it will signal a high EQ — a favorable characteristic for a founder to have, coming from an investor who is trusting you with their reputation and their capital.
Personalize Your Approach: Tailor your outreach and communication to each investor and/or fund, and emphasize why you want them on your cap table. Show genuine interest and commitment to nurturing the relationship. There is a lot of capital available in the world, and being selective about who you take it from signals thoughtfulness and intention.
Educate Mindfully: Work the call. Identify in real time where your investor is “not getting it” because you WANT your investor to “get it.” You don’t want them leaving the call with questions they won’t have answers to during investment committee — otherwise, you’re risking confusion, and confusion doesn’t lead to green. Start with the basics and gradually delve deeper into your solution. Avoid overwhelming investors with technical details unless prompted.
Find Your “Knowing”: Know yourself, who you are, and what you believe in. Investors are attracted to people with a perspective on the world and how they want to change it. They like founders with strong opinions and a willingness to fight for them. An investment in this type of person is that much sweeter in the end.
You won’t go wrong by following these principles. Remember: sometimes it takes a couple of swings before you hit a home run. The journey seldom gets easier, but it will get more familiar over time. My hope is that these guiding principles become second nature. 1-9 can be easily practiced today. As for 10? Well, that one can take a lifetime to master. You’ll know when you’ve found it.
If you’re on your company-building journey and want to work together, I’d love to meet. Schedule some time on my calendar here so we can dive in and get you closer to a win.