Sales sucks. Here’s what to do about it

I got home Friday night after a long week and a day trip. I was sad. My wife looked confused… "I haven't seen you like this since the Ampush days."

I haven't shared yet the BIG thing I'm working on but I'll tease it now. This year, I've started doing something I've rarely done: I've been out fundraising.

"FOR WHAT, JESSE?" I will share soon.

But let's just say: I've learned why I was never drawn to it. It’s a type of sales which I usually like, but there's something more personal, more existential about it.

Like all sales, there's a lot of meeting new people, storytelling and even ideating about the future. Those parts I like. 

However, it also comes with the challenges of getting people on the phone, difficult personalities and, the worst thing, rejection.

There's no question it’s a grind, BUT it’s also necessary for any business venture whether you're fundraising or bootstrapping. You gotta pound the pavement! So if that's true, and it sucks, what is one to do? 

Here's a letter mostly reminding myself of a few things:

My sadness last week mostly came from expectations. I told myself the person would say yes. That led to a bunch of problems.

First, I probably under prepared. 

Second, when the meeting started going sideways, I started freaking out. Not in an obvious way, but inside, I became less dynamic, more rigid.

I felt my brain get foggy and my body tense up. I was losing the deal!

That made me less effective as a problem-solver and less curious as a question-asker (both important things for sales).

And last, I felt like shit afterwards.

Instead, I think it’s best to walk into every meeting with a "curious about the possibilities" mindset and be open to however it unfolds. 

Statistically, by the way, you will hear 4 NOs for every YES, so maybe just assume everyone will say no. Although I prefer the “open to whatever comes” stance.

Pro tip: oftentimes, expectations aren't conscious. Try to notice your thoughts ahead of a meeting. 

Are you banking on that one being good because others have been bad? 

Are you saying things like, "We gotta get this one and then the whole thing will turn." If so, you may be attached.

One thing that helps avoid number one is simply scale. People often say, “It’s just a numbers game.” They are right.

If you are doing one meeting a week, each one feels like the Super Bowl. If you’re doing ten, they are just practices.

Fundraising in particular has somewhat of an infinite funnel because lots of different kinds of people have money and, in theory, anyone can invest in anything.

The related point here is volume and density of meetings matter. It’s not just “take a lot of meetings” but “take a lot in a short period of time.” It really helps you understand the market and what you’re selling.

Sales, especially fundraising, become amazing classrooms. But only if you reflect after every conversation, or at least daily.

What went well? What could have gone better? What common themes are you hearing across conversations?

A quick debrief will lead to adjustments and will keep improving your pitch.

I also like to leave room for experimentation. If you have enough volume of meetings, try a different "intro" or emphasize different points during the pitch. 

See what comes back. Over time, you'll learn what works best!

This is true in any sales context. If you're everything to everyone, sales will be absolutely brutal.

It will be too high volume, way lower conversion and, even worse, if you get a yes, the person will probably not be aligned.

Instead, figure out who is the ideal customer, investor, etc. And TELL them why! To start, a great ICP list has hundreds of people. No more than a thousand. 

Make sure you know why someone is a good fit, which includes why what you're doing is valuable to them and why they are valuable to you. 

All business relationships are ultimately two-way relationships.

Once you find your ICP, don't go to your most valuable prospect first.

I like to start with either “friendlies “(low-risk, high-trust relationships) or "tier 3” type conversations. 

This gives me a chance to hone in the pitch and get honest feedback. Then, midway through I want to hit the tier 1s!

It's the end of the meeting. Everyone's smiling and nodding. Vibing. And time is coming to an end. 

It’s SO scary to try and "close.” I teach this all the time, but even find myself being like, "I don't want to ruin the vibe!"

But then what happens? Everyone says, “Really cool, let’s follow up.”

Then they disappear. They get busy. And you start to look desperate. Even worse, you don't really get the data you want.

It’s easy and tempting to lie to ourselves but instead, at the end of any sales meeting, you must ask, "How interested are you?" 

A version I heard for fundraising is, “Are you more excited or less excited about this than when we first started?"

And, from there, "So, how much do you want to invest?"

You have to put people on the spot because truth is critical to success in sales. 

Beyond closing, it’s also important to own the time: set the agenda, be clear what you're asking for (feedback, intros, $) and pivot as necessary. It’s your show.

Well! This isn't the email I was planning to write, but here we are. What other questions do you have? What did I miss? Thanks!

Have a great week.

jesse