One of the most valuable lessons I've learned when it comes to fundraising or selling is to always ask for permission to make your pitch upfront. This approach not only respects the other person's time and decision-making process but also increases your chances of finding the right match and achieving your goals.

I used to think the right approach was to convert cold contacts into warm ones gradually over time, winning them over so thoroughly that investing in or buying from you became an obvious choice.

I encountered this issue while fundraising for a project last winter. I was introduced to an operator and investor with deep experience in my domain. We had lunches and coffees regularly over several weeks. I gave regular updates on my project, my team's progress, and all of our needs (primarily financial support). After our fifth or sixth meeting, I came out and asked if she thought she could be helpful financially or in terms of her expertise in her network — I felt that the needs of my team were clear. She shrugged off my request, stating that I wasn't being specific enough and that the lack of directness would waste my time. Our relationship trailed off after that.

When I realized my error, I adopted a new approach of asking for permission to pitch. From that point forward, I became more direct when going into my conversations, stating the context upfront ("Here's what I'm working on and excited to talk about"), and making sure to ask them explicitly if they were comfortable with me making a pitch later on ("If you're comfortable with it, I would love to later ask if you're interested in contributing or collaborating on what we're working on. Does that sound good to you?").

Explicitly asking for permission to make your pitch makes the process much easier for everyone involved. It saves the person you're pitching time by allowing them to think immediately about whether they can help you or not, and if not, it's an easy pass. In the meetings after that, my meeting times shrunk from 35-minute catch-up coffees to 15-minute streamlined operating calls; the people I spoke with were able to make quick decisions about whether it made sense for us to collaborate or not.

A few meetings later, I had a call with the head of a media company. I explained what we were working on and asked if I could pitch him later in the conversation. He said yes, and throughout the discussion of my project, I could see the wheels turning in his head as to how he could be immediately helpful. At the end of the call, he told me that while he couldn't give money, he would provide us with equipment, cameras, and any other tools our team needed free of charge. He also provided introductions to other industry experts, some of whom became the investors we needed. The call took less than 15 minutes. Articulating clearly what help my team needed and framing the conversation around this question of collaboration made things move so much smoother.

The reason it took me so long to internalize this lesson was because I was always under the false impression that sales were all about relationships, handshakes, charm, and charisma. I thought you made someone like you, and only then, once you had secured your place, asked them for a favor. The element of relationship building is absolutely critical, but I also think that the most ideal form of fundraising is informative, not persuasive. When you meet with someone, the idea should be communicating your mission and needs transparently. There needs to be a mindset shift away from "I need you to make this happen" towards "This is happening with or without you, hop on if you'd like." Asking for permission to pitch aligns with this informative, non-persuasive approach.

When fundraising or selling, it's crucial to ask for permission to make your pitch upfront. By being transparent about your intentions from the start, you respect the other person's time and decision-making process. This approach also saves you from wasting energy on those unlikely to commit. When your pitch resonates, you'll find eager collaborators — it only takes one "yes" to get things going. Asking for permission to ask increases the chances of finding that right match.