Getting your first paying customer (B2B/Enterprise)

June 6, 2023

Y/N: “I want to go create a b2b/enterprise startup where folks pay $2k/month or more. How do I get started?”

Me: I’ve helped dozens of founders get into YC, get funded, and land their first enterprise clients through my community

Here’s what I’ve learned in working with Christina, Sarah, Drodio, Ben, Rishi — all who’ve landed 5-6 figure paying customers for their B2B Enterprise, VC backed startups.

Do you value passion or market more?

First thing to get clear on is, what is your end goal.

🔷 Is your end goal to create a company with the biggest market? (eg: 1B ARR)

🔷 Is your end goal to create a company in a market you’re passionate about? (eg: 1M ARR)

If your end goal is to create a company with the biggest market,

  • What will happen when you find out your market is uninteresting/boring?
  • For example, you talk to 200 people and you find that people will pay $10k/month for this gnarly painpoint. The biggest painpoint they have is needing logging and security audits on a Crypto chain. 🤢
    • Would you pursue the idea? How would it make you feel?

If your end goal is to create a company in something you’re passionate,

  • What will happen if your market is not willing to pay that much money. What will you do then?
  • For example, you talk to 200 queer women college students and you find the biggest pain point is wanting to meet more queer people. But only a few people would be willing to pay $5/mo for a solution. 🤢
    • Would you pursue the idea? How would it make you feel?

Do you value money or passion more? Get clear on this before you move forwards

This guide is for those who values big markets over passion area 😀

This is for you if

  • You are industry agnostic
  • Are willing to talk to 50-200 people
  • You value building a profitable, large B2B enterprise over your ideas / passion area

This is not for you if

  • Prefer to ship your own idea instead of learning what the market actually wants
  • Won’t do the grind yourself - eg: talk to 50-200 people
  • Won’t face rejection yourself — eg: actually sell, actually market and put yourself out there

I’ve worked with tons of successful enterprise founders and everyone knows how important it is to talk to customers, sign contracts, and yet so many first time entrepreneurs don’t do that. The product people focus on product instead of doing sales/marketing. The technical people jump into coding their MVP instead of doing sales/marketing. The business people make pitch decks and talk to VCs instead of doing sales/marketing. Everyone’s trying to protect their baby from reality.

The result is, these founders don’t know if they are building something people will pay $2,000+/month for — until it’s too late.

Let’s get started.

GOAL 1: Need-find the most profitable idea

  • The goal is to collect a bunch of Paintpoints/Willingness to pay and pursue the one that is most profitable.
  • Drodio (2x YC) used this method to create his series D startup, Armory
  • Like this:

Your goal is to fill this table with 10-30 conversations

Then pick the one with the most $$$$ to pursue

Step 1. Ask to do need finding interview

“Hey Sarah, I wanted to do a needfinding interview with you. My startup died. I'm pivoting and I need your help, would take max 30m. No worries if you are busy.”

Reach out to 30-50 founders, engineers, sales, sales, designers, etc. Kudos if they are in enterprise (willing to pay more!) 🙂

Step 2. Extract Painpoint, Cost, and WTP

Get these rows filled out during the interview

Step 3. Profit off people’s pain.

Hey Bob, I was wondering if we can chat for 15. I was thinking about your sales problem, and was wondering if i can get your feedback on something. I wonder if this would help. No worries if you are busy

Sarah Nagy (7.5M Raised, Founders cafe member)

GOAL 2: Test if people will actually pay for the profitable idea

Now that you have a profitable idea you want to pursue, your goal is to find out if people were lying or are actually down to pay 🙂

Step 1. Present your sexy offer — Go back to the person you interview, and present the offer. See if they bite.

Step 2. Convert them on the call, or have them champion you to the buyer.

Step 3. PROFIT!!

Now you have achieved Goal 1 and Goal 2

  • You have a profitable idea
  • You have paying customer
  • What's next? Talk to more of the same kind of customer, see if they have the same painpoint, and convert them!

Biggest mistakes


Mistake #2: When you have an offer, don’t pitch it immediately.

Make sure you understand their specific problem.

Which looks like “I am trying to do X but I can’t because Y”

“I am trying to train my sales rep but I cannot because I have to spend 60 hours doing that”

Then you can say, “I can save you 60 hours, by training them ourselves :D”

Biggest tip

If you actively listen to others, they will…

  • Listen to you
  • Trust you more
  • Pay you more
  • Spill more tea

My therapist actively listens to me and I spill ALL THE TEA

How to you actively listen?

  • Active listen = Paraphrase + Ask open question


  • THEM: “I prepped for my VC meeting until 4am last night”
  • YOU:Sounds like fundraising has been stressful. What has the process been like?

LMK what you think!

I’m Maddie. I help founders get their first paying customers at

Maddie Wang founders of founders cafe solo founder
Maddie Wang
Gay / Solo-Founder / Stanford Dropout

I'm building Founders Cafe because as a solo founder, it can be very isolating. Last year, I lost 4 co-founders and a best friend on a previous startup.

Previously built a Minecraft Server ($61k), Amazon Store ($120k), and Queer Chart, where I met my girlfriend & close friends.

If you're interested in joining the Founders Cafe, let's talk and if it's a good fit, down to invite you!

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