Get your first customers

Should I offer a free trial, a paid pilot, or a discount to close my first customers?

The short answer

Free trials attract tire-kickers, so early on a short paid pilot is usually better, even a small fee proves they have real budget and intent. Use a pilot with a clear success metric and an agreed date to decide, so it converts to a real contract instead of drifting forever. Save discounts for a genuine reason (a case study, a reference, a multi-year commitment), because a discount given for nothing just teaches the buyer your price is fiction.

Go deeper, your way

18 hand-picked resources, 16 link-checked. Pick how you want to dig in.

▶️ Video
✓ Link checked Free Beginner

Why we picked it This is the canonical short talk on winning your first users when you have no audience and no sales team. Alstromer (YC partner, former head of growth at Airbnb) makes the case that early on you do things that do not scale: you go where your users already gather, reach out directly, and talk to them one at a time. For a solo technical founder that is a relief, because it is closer to helping people in a community than to cold-call selling.

How to Get Your First Customers (Startup School)

On Y Combinator (YouTube) by Gustaf Alstromer About 25 minutes

How to Get Your First Customers (Startup School)
  • Do things that do not scale at the start: hand-find your first users in the communities and forums where they already hang out.
  • The founder should be the one doing early sales, because nobody understands the product and the problem better than you.
  • Charge early and watch who actually says yes; a real customer is a much stronger signal than a free sign-up.
Watch on YouTube youtube.com →
▶️ Video
✓ Link checked Free Beginner

Why we picked it Kevin Hale's YC lecture is the clearest introduction to pricing first principles and the mistakes founders repeat. The pricing-thermometer framework (cost, price, value) is worth the watch alone.

Startup Pricing 101

On ycombinator.com by Kevin Hale (Y Combinator) ~35 min video + transcript

  • The most common pricing mistake is charging far too little
  • Price sits between your cost and the value delivered, anchor to value
  • Small price increases often have an outsized impact on your ability to grow
Open ycombinator.com →
▶️ Video
✓ Link checked Free Intermediate

Why we picked it Tom Blomfield's practical framework for pricing when you sell to businesses, including why to charge from the start and how to talk about money without flinching. Direct and tactical for founders selling to companies rather than consumers. It pairs well with the Kevin Hale talk.

How to Price for B2B (Tom Blomfield, Y Combinator)

On Y Combinator Startup Library by Tom Blomfield

  • Business customers expect to pay, so charge them from the start.
  • Anchor your price to the value you create or the cost you save.
  • Do not let your own discomfort with money set the price.
Open ycombinator.com →
🎧 Podcast
✓ Link checked Free Intermediate

Why we picked it Jen Abel has coached over 300 early-stage founders through their first sales, so this is grounded in what actually happens when an operator turns founder and has to open the first conversations. The core move here reframes your worry: treat those first outreaches as research, not pitches, which is precisely how you tap your old network without it feeling like you are cashing in on the relationship. Audio, video, and a full transcript are all on the page, so pick whichever way you learn.

The ultimate guide to founder-led sales | Jen Abel (JJELLYFISH)

On Lenny's Podcast by Lenny Rachitsky with Jen Abel About 1 hour 16 minutes

  • Treat early sales conversations as customer discovery: you are learning whether the problem is real, which lets a former colleague engage without feeling sold to.
  • There is a repeatable structure to first calls, demos, and follow-ups, so warmth from your network is the opener, not the whole plan.
  • Founder-led selling is expected at this stage; your industry context is an asset when you lead with the problem instead of the product.
Open lennysnewsletter.com →
🎧 Podcast
India Free Beginner

Why we picked it Long-form, candid interviews with Indian founders and investors on how they actually grew, distributed and built brand, one of the best Indian sources for founder-led growth stories.

The Neon Show (100x Entrepreneur Podcast)

On The Neon Show / Neon Fund by Siddhartha Ahluwalia 200+ episodes

  • Real Indian growth playbooks straight from founders who executed them.
  • Covers 150+ Indian founders, VCs and operators across sectors.
  • The podcast itself is a case study in building audience and distribution.
Listen on Spotify open.spotify.com →
📖 Book
✓ Link checked Paid Beginner

Why we picked it The single best thing ever written on customer conversations. It teaches you to ask about the customer's life and past behaviour, not your idea, so you can't be lied to. If a founder reads one thing before talking to a single customer, it's this.

The Mom Test

From momtestbook.com by Rob Fitzpatrick ~130 pages

  • Talk about their life, not your idea.
  • Ask about specifics in the past, not opinions about the future.
  • 'That's so cool, I'd totally buy it' is a compliment, not data, dig for commitment and evidence.
Open momtestbook.com →
📖 Book
✓ Link checked Freemium Intermediate

Why we picked it The authoritative handbook on founder-led sales, written for technical/first-time sellers building B2B SaaS. Readable free online via membership, and covers the whole motion end to end.

Founding Sales: The Early Stage Go-to-Market Handbook

From foundingsales.com by Peter Kazanjy book (~400 pages)

  • Do ~50 demos and hit a ~20%+ win rate before hiring your first sales rep.
  • Discovery before demo, understand the problem before you pitch.
  • Dedicated chapters on prospect outreach and demo appointment setting.
  • Turn founder selling into a documented, repeatable, transferable process.
Open foundingsales.com →
📄 Article
✓ Link checked Free Intermediate

Why we picked it Patrick Campbell built ProfitWell on pricing data from thousands of companies, and this is the single best free deep-dive on SaaS pricing strategy. It's the canonical starting point for value metrics, segments, and packaging.

Pricing Your SaaS Product

From lennysnewsletter.com by Patrick Campbell (ProfitWell), via Lenny's Newsletter long-form guide

  • Get your value metric right and you can afford to get other things wrong
  • Pricing is built on quantified buyer personas and willingness to pay
  • Optimize pricing quarterly, it's an ongoing process, not a one-time decision
Open lennysnewsletter.com →
📄 Article
✓ Link checked Freemium Intermediate

Why we picked it The most concrete guide to actually measuring what customers will pay, including survey methods and tier design. It turns pricing from guesswork into a research-driven process.

The Ultimate Guide to Willingness to Pay

From lennysnewsletter.com by Lenny Rachitsky & Patrick Campbell long-form guide

  • Measure willingness to pay directly through structured customer research
  • Design tiers around distinct customer segments, not arbitrary feature bundles
  • Localize pricing by market and currency to capture willingness to pay everywhere
Open lennysnewsletter.com →
📄 Article
✓ Link checked Freemium Intermediate

Why we picked it A tactical follow-on covering the channels and motions top B2B startups scale after the first ten. Grounds distribution strategy in real company examples.

How to win your first 10 B2B customers

From Lenny's Newsletter by Lenny Rachitsky ~15 min read

  • Content/SEO is a surprisingly dominant B2B channel (Vanta, Amplitude, Figma, HubSpot).
  • The core B2B channels: self-serve inbound, sales-assist inbound, outbound, content, paid, partnerships.
  • Pick and systematize the one channel that compounds for you.
  • Distribution strategy should follow evidence, not fashion.
Open lennysnewsletter.com →
📄 Article
✓ Link checked Freemium Intermediate

Why we picked it A data-backed teardown of how companies like Figma, Gusto, and Vanta actually sourced their earliest customers. Replaces guesswork with real patterns.

How today's fastest-growing B2B startups found their first ten customers

From Lenny's Newsletter by Lenny Rachitsky ~15 min read

  • Only three sourcing strategies power nearly all very-early B2B growth.
  • Tap your personal network first (Gusto's first 10 were friends/YC batchmates).
  • Reach influential users via direct outreach (Figma cold-emailed top designers).
  • Start with the highest-trust channels and work outward.
Open lennysnewsletter.com →
📄 Article
✓ Link checked Free Intermediate

Why we picked it A direct answer to the exact question in the title: yes, charge for pilots, and here's roughly how much. Jason Lemkin argues that an unpaid pilot is really just an extended demo, and that even a modest fee changes how much attention and honesty you get back from the customer. Read this if you need a straight answer, not a framework.

Dear SaaStr: Should We Charge for Pilots and How Much?

From SaaStr by Jason Lemkin

  • An unpaid pilot is an extended demo, not a real test
  • Charge something meaningful enough that the customer feels it
  • A paying pilot customer gives you more honest feedback than a free one
Open saastr.com →
📄 Article
✓ Link checked Free Intermediate

Why we picked it Picks up right where the previous piece leaves off: once you've decided to charge for the pilot, how do you actually structure it so it converts. It's specific about setting a success metric and a decision date up front, which is the exact mechanism this question's answer points to. Short and practical.

Dear SaaStr: We're Starting a Big Paid Pilot. How Do We Maximize the Chances of Success?

From SaaStr by Jason Lemkin

  • Agree on what success means before the pilot starts, in writing
  • Set a hard end date so the pilot doesn't drift indefinitely
  • Involve the economic buyer in the pilot, not just the end user
Open saastr.com →
📄 Article
✓ Link checked Paid Advanced

Why we picked it A pricing consultant's argument that most companies discount reflexively instead of strategically, with a framework for deciding when a discount actually earns you something back. Useful once you're past the first pilot and start seeing discount requests as a pattern, not a one-off. Helps you turn the genuine reason test into an actual policy.

The Art of Discounting

From Harvard Business Review by Rafi Mohammed

  • Most discounting is a reflex, not a strategy
  • Tie every discount to something you get in return, not just goodwill
  • An unearned discount trains the buyer to expect one every time
Open hbr.org →
✍️ Essay
✓ Link checked Free Beginner

Why we picked it A short, sharp reminder that your price tells a story, and that cutting it to close a deal usually just tells the buyer the original story wasn't true. Read it in two minutes right before you're tempted to discount out of nerves on your first sales call. It's the plainest version of why an unearned discount backfires.

On pricing

From Seth's Blog by Seth Godin

  • Your price is part of the story you're telling, not just a number
  • A discount without a reason undermines the price you'll ask for next
  • Competing on lowest price is a race you can win and still lose
Open seths.blog →
📄 Article
✓ Link checked Free Intermediate

Why we picked it The other side of the discount question: sometimes a genuinely low price is the right strategy, not a concession. Jason Lemkin lays out the narrow set of conditions where that's true, which helps you tell the difference between a deliberate low-price strategy and just caving to the first customer who pushes back. Read it so your discount decisions are a choice, not a habit.

Dear SaaStr: When Does It Make Sense to Price Low in the Market?

From SaaStr by Jason Lemkin

  • Pricing low is sometimes a real strategy, but only in specific conditions
  • Know which condition you're actually in before you cut your price
  • A deliberate low price is different from an improvised discount
Open saastr.com →
✍️ Essay
Free Beginner

Why we picked it The permission slip to recruit users by hand, do things manually, and deliver 'insanely great' experiences to your first few customers. The cheapest, most honest way to validate demand is to go get it one person at a time.

Do Things That Don't Scale

From paulgraham.com by Paul Graham ~15 min read

  • Recruit your first users manually, don't wait for them to come.
  • A tiny group of users who love you beats a big group who like you.
  • Manual, unscalable effort early is a feature, not a failure.
Open paulgraham.com →
📋 Template
✓ Link checked Free Beginner

Why we picked it A free, plain-language contract template built specifically for running a paid pilot, with the scope, fee, and success criteria already structured for you. Saves you from either skipping the paperwork, letting the pilot drift forever, or over-lawyering a deal that should close in weeks. Use it as the starting draft for your first paid pilot.

Pilot Agreement

From Common Paper

  • A written pilot agreement turns a vague trial into a real deal with a deadline
  • Put the success metric and conversion terms in the document itself
  • Starting from a template is faster than drafting a pilot contract from scratch
Open commonpaper.com →

People also ask

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