You took my unusual advice around pitch decks, tackling risk, and facing rejection head-on. I’ve got more for you.

Today, we’re getting into polishing your pitch and preparing your fundraise the right way. Let’s get you prepped and primed to make the most out of every meeting…

Pitch Smart, Not Staged

Stop staging your approach to investors you talk to. I know everyone says to do this, but I hate it. 

The common suggestion is to pitch third tier investors first. Then, after refining your pitch based on their feedback, you move on to tier 2, and finally, tier 1 investors once you’ve got your pitch honed. Here’s why I’m not a fan of this approach…

To start, what makes a firm tier 1, tier 2, or tier 3? There might be some league tables that rank A16z, Greylock, and Benchmark as top-tier, but there are also great investors who might not be on those lists. You might discover that an investor you thought was a tier-three is actually a perfect fit for you. You only find that out by talking to them and understanding their interest in your space.

More importantly, breaking it down into tiers can dilute the energy in your process. By doing a few pitches now, then waiting, and then doing more later, you lose momentum. Instead of wasting potentially high quality meetings to “get feedback”, I recommend you get all your practice, feedback, and iterations done before you even start pitching. You can get that stuff without burning pitches. 

Talk to other founders, get feedback from friends, or even pitch VCs who might not be the best fit for your stage to refine your story. Then get the idea of “staging” out of your mind and instead aim for calendar density. That means go fill up your schedule with as many meetings as you can in a densely packed area of your calendar. Skip the tiering system and focus on making each pitch count.

You Can’t Wing It And Win It

This one’s more of a controversy in founders’ minds.  Founders think they can wing it, fake it till they make it, and be successful without wasting the time to prep.  You might think you can catch lightning in a bottle—talk to one investor, and boom, they invest, but it’s just not true. Some of you probably disagree with this… but you HAVE to prepare to win. Preparation is the key to success. 

The best fundraisers, the ones that really nail it, are the ones who put in a ton of effort before they even step into the room. And I’m not talking about founders who had to hustle extra hard because they didn’t have a network or connections. I’m talking about founders from pristine backgrounds, with killer networks and experience that would make you think they’ve got it in the bag. These founders know that by preparing ahead of time, they are optimizing their opportunity and advancing their chance of success.

I interviewed Bobby Pinero, the founder and CEO of Equals, for my podcast Funded. Bobby went to Stanford, was an early employee at Intercom, and knew some of the top founders and investors out there. But when he prepped for his Series A, he didn’t just wing it. He spent months getting ready, far ahead of when he actually needed the cash. He dedicated serious time to making sure he was fully prepared, and that’s what drove his success.

Remember, preparation is key. Don’t fool yourself into thinking overnight success is something you can plan for. It's the consistent work behind the scenes that truly makes a difference.

So, those are my “controversial” fundraising ideas. Yeah, we might be using the word controversial to add a bit of clickbait, but honestly, these are five concepts that should really get you thinking about how you approach your fundraising. If you take them to heart, they’ll push you to become a stronger, more effective fundraiser overall… 💪 

Be chased,
Jason