Guide

Prospecting is building a list of ICP accounts and contacts, then earning conversations. Sources: your network, LinkedIn, conference lists, product signups, job postings that signal the pain, intentional warm intros.

Outbound email and LinkedIn work when they are short, specific, and aimed at a reply — not a novel. Tyler Bosmeny's YC talk pattern: who you are, one-line what you do, why them (personalization), clear ask for time. The goal of the first message is a meeting, not a close.

Volume math matters. If you need 10 customers and reply→close rates are typical cold outbound, you may need thousands of touches. Track rates weekly or you fly blind. See the worked funnel in GTM funnel metrics: 10 customers at those rates implied 20,000 emails.

Block founder calendar for outbound like you would for coding. "I'll sell when the product is ready" is how products stay forever almost-ready.

Concept

Founder-led sales means the people who can change the product are the ones hearing objections live. Every "we need SSO" and "your pricing is confusing" becomes roadmap input — not a CRM note nobody reads.

Common early objections

ObjectionWeak replyBetter reply
"We already built this in-house""Ours is better""What does maintenance cost you per year? Where does it break?"
"Send a deck"40-page PDF into the void"Happy to — after a 20-min call so I send the three slides that match your setup"
"Need to think""Okay, circling back next quarter""What specifically are you weighing? Security, price, or priority vs other projects?"
"Too expensive"Immediate 40% discount"Compared to what? If we hit metric X, what is ROI? What term/commit gets you to yes?"

Never invent roadmap promises to close. If you commit, write it down with a date.

Paul Graham's "do things that don't scale" applies: hand-onboard, sit in their Slack, write the migration script yourself. That labor discovers the scalable motion later.

Common mistakes

  • Writing a novel instead of asking for a meeting.
  • Waiting until the product is ready to start outbound.
  • Naked discounts instead of trading term (annual prepay, multi-year, reference rights).

Check yourself

  1. What is the first outbound email trying to win? A meeting, not a close.
  2. You need 10 customers and cold reply rates are ~5%. What must be true? Top-of-funnel volume is huge — thousands of touches, or you need inbound / a tighter ICP / a different motion.

Key takeaways

  • Prospecting builds an ICP list. Outbound earns a meeting.
  • Short, personalized, one ask.
  • Volume × conversion is the plan. Track rates weekly.
  • Founders block time for this the way they block time to code.

Further learning

Once you have the meeting: sales discovery.

How to Sell by Tyler BosmenyY Combinator