How I Sell (as a Bootstrapped Founder)

If you’re going to Bootstrap a B2B business, getting good at sales is absolutely critical.

I’d go so far as to say, if you don’t like or want to sell a lot, don’t choose a B2B company to bootstrap. Because in your first year (and maybe even your fifth), you’ll be selling a lot.

Here’s my cheat sheet for selling that I teach all my GX Founders.

How do I get meetings?

The simplest system here to start is use your network. I say this to most founders and they nod and then look blankly at me. Some ask: HOW?

Simple. Linkedin.

The way I start every business: identify 50+ target companies/people who I want to sell to (this is usually somewhat narrow but still broad enough to learn, over time I tighten the “ICP” or Ideal Client Profile).

Then, the key thing - I try to see how my network can get me in front of those targets.

Ideally, I have a mutual connection with 20-30% of people on my list. I’ll even use 3rd degree if I have to. A warm meeting is worth at least 10x more than a cold meeting. (In a future email, I’ll share my entire system with templates on how to do this.)

How do I run a meeting?

Now you have the meeting and you’re preparing. Start with a tight agenda.

“Well, thanks so much for hoping on the call. What I’d love is to hear your background and

why you took this call, then I can intro myself and tell you about [Company name] and then would love your questions.”

The agenda looks like:

  • 1-2 min pleasantries

  • 2-3 mins prospect shares about themselves + why they took the call

  • 5-7 mins you pitch (share a deck and demo if relevant)

  • 5-10 mins Q&A (in both directions, including discovery)

  • 3 minutes: next steps

A few things:

+ I like to ask why someone took the call to gauge their interest level. It’s important to know where you’re starting! In fact, one really important thing in sales is to constantly get a sense for reality/where you stand. We’ll come back to this.

+ I keep my pitches short. I ALWAYS pitch as a story. Founders have a unique credibility when selling that no one else has → They have chosen to spend their LIFE doing the thing they are doing. It’s not just a job, and everyone knows it. So make it personal.

+ Most of my pitches start with: “Here is who I am, here is why I’m doing this, here are my hopes/dreams.”

+ Then, I use sentence stems for framing. Example: "The problem we wanted to solve is...", "How this works is...", "What makes this unique/different/special is..." (I'll go deeper into these in my email on Thursday).

There’s a lot of talk about doing discovery but I don’t push it up front because most people are on the defense when joining a sales call so I find a short intro/story sharing really builds trust.

In preparing for the pitch, I use one of my favorite frameworks: Think, Feel, Do.

Before starting to work on a deck/pitch, ask yourself, what do you want the person to:

  1. THINK - this is specific thoughts about you or your offering

  2. FEEL - these are real emotions (happy, sad, excited, curious)

  3. DO - this is a specific set of actions

How do I end my meeting?

Once I complete my pitch, I pause and say: “So what do you think?” - this again, is another way to gauge reality of what the person thinks.

Most of the time, if the person seems disinterested, I DO NOT waste my time trying to convince them. (If they genuinely don’t get, that’s different.) I used to try and convince but realized you’re better off finding someone where there is a strong pull/fit than convincing someone who is lukewarm.

I field questions. I ask genuine questions (not sales ones). I’m authentic about what we know and don’t know (people can tell when you are BSing).

Then, I start talking next steps.

Specifically, I push to get another meeting. This is another way to see where the person stands. Ideal is they whip out their schedule and book another time. Also ideal is if they just say no (saves you time!), if they are interested but don’t book - I try to have as an immediate follow up for booking a meeting as possible.

The last tidbit: What will that person repeat internally? A lot of sales is really equipping the person you are speaking to to “re-sell” your offering internally.

So I always ask: Imagine that person’s CEO calls them right after the call and says “so what did that Jesse guy pitch you?” - how do you what them to respond?

Ideally, they have 2-3 CRISP takeaway sentences they can share up:

  1. What is the offer?

  2. What makes it different?

  3. Why they are excited?

For number 1, we’ll cover offer in a future email but the short version is: Make it short, easy to understand and easy to repeat.. e.g., “they will make us amazing influencer creative for $5k per month.”

That’s it - Happy selling!!

What did I miss, what questions do you have?