What Entrepreneurs Can Learn from To Sell Is Human
Founders spend most of their waking hours trying to move someone toward a yes — an investor, a first customer, a skeptical hire, a landlord. The trap is treating every conversation as a chance to deliver the pitch you've already perfected in your head, instead of finding out what the person across the table is actually weighing. When an idea has consumed your last six months, it's easy to assume everyone else stands where you stand. They almost never do.
The whole book, compressed
This edition works through 4 core lessons — take them one at a time, not all at once.
What's different for your conditions
Tap whichever ones sound like you. Nothing here is sent or saved — it's just for your own noticing.
0 of 5 selected
The core lessons, applied to you
Whose Decision Is This, Really
Before a pitch or a sales call, write down in one sentence what the other person is actually deciding — not what you want to tell them. An investor eyeing your roadmap slide may really be deciding whether your team survives a bad quarter. A customer nodding along to your feature list may really be deciding whether switching tools makes them look foolish to their boss. Your job isn't the best pitch; it's correctly guessing the actual question in the room.
A founder walks a seed investor through eighteen months of roadmap, proud of the ambition. The investor keeps steering back to burn rate and team depth; the founder keeps steering back to vision, reading the questions as market skepticism instead of a different, unaddressed decision. The meeting ends warmly and goes nowhere.
Before each significant call, write one line — "the other person is deciding whether ___" — and check your opening three minutes actually speak to that sentence, not to your own excitement.
Turning a No Into a Debrief
Founders collect nos the way other jobs collect emails — constantly, without ceremony. The instinct is to let each one settle as evidence about your worth. A steadier habit asks a narrower question: what does this specific no tell me, and what doesn't it tell me? A no from an investor outside your stage says almost nothing about your product. A no from three design partners citing the same missing feature says plenty.
After forty investor passes, a founder quietly starts believing the company is fundamentally broken, when the notes show most passes cited "too early for our fund" — a portfolio-fit reason unrelated to the product. The founder nearly kills a feature customers loved, chasing a signal that was never about them.
After every no, write one line naming the specific, stated reason, separate from any story you're tempted to tell about what it means about you.
Showing Them the Gap They Hadn't Priced In
The strongest pitches don't out-argue the prospect; they help the prospect notice something true they hadn't fully added up — a cost they're absorbing quietly, a risk they've stopped seeing because it's become routine. That's different from manufacturing urgency with a countdown clock or a "this offer expires tonight." Genuine help points at something real and lets them draw their own conclusion; pressure invents a deadline to short-circuit their thinking.
A founder, worried a demo is going flat, tells the prospect the discounted price "goes away tomorrow," even though nothing is actually changing. The prospect senses the manufactured urgency, disengages, and mentions it to a peer considering the same tool.
Before a sales conversation, identify one true, specific cost of the prospect's current approach that they likely haven't calculated, and lead with that observation instead of a feature list.
The Ask as Something You're Offering, Not Extracting
Every fundraising ask and sales pitch lands better once you can honestly describe it as solving a problem the other person already has, rather than only funding your dream. That reframing isn't a script trick — it only works if it's true, which means confirming the fit actually exists before you ask.
Understanding the other side properly takes time you may not have on a shrinking runway. Resolve the tension by time-boxing discovery deliberately — three sharp questions before you pitch, not thirty — so genuine curiosity doesn't quietly become an excuse to stall.
Name one thing, honestly
Think of the ask you most need someone to say yes to this month — what do you actually know about what they're deciding, versus what you're assuming?
Good. Now look back at the "Try this" line under whichever lesson feels most connected to what you just wrote, and treat that as this week's actual assignment — not all 4 at once.
The practices from this edition
0 of 3 selected
Run this for seven days
Before a sales conversation, identify one true, specific cost of the prospect's current approach that they likely haven't calculated, and lead with that observation instead of a feature list.