How one rejected pitch became a yes ninety days later
Jordan had spent three weeks preparing for the meeting, and it lasted twenty-two minutes. The investor was polite, even encouraging, but the answer was a version of the one Alejandro Cremades warns founders will hear constantly: you're too early, not enough traction. Jordan left the building already composing the mental obituary for that relationship, the way most people do when someone tells them no.
Cremades's argument is that this reaction, understandable as it is, throws away most of the value in the interaction. A no from an investor, he writes, doesn't always have to stay a no. Sometimes it really is timing. Sometimes the investor isn't hearing the pitch quite right, and the fix is to connect the dots better, not to disappear. He borrows the sales-training wisdom used in mortgage and real estate, where new agents are taught that nine noes lead to one yes: every rejection, in that framing, is one step closer to the yes, not evidence that there isn't one.
So instead of writing the investor off, Cremades suggests something closer to a slow, generous follow-up. Jordan, taking that advice, sent a short thank-you note that evening. The investor had mentioned, in passing, a real interest in health-care startups; Jordan's note included links to three health-care companies operating out of the same coworking space, no strings attached. Ninety days later came a second note, this time with real news: a development milestone hit, a new batch of users onboarded, an invitation to try the next version early. A few weeks after that, a third message, short and specific: two weeks from a major milestone, here's an updated deck in case you know anyone else who might be interested.
None of this was designed to manufacture urgency or fake a relationship. It was designed to keep Jordan present in that investor's mind as someone delivering on what they said they would, quietly, over months, without asking for anything in return each time. Cremades sums up the logic in a line worth remembering: ask for money, get advice; ask for advice, get money twice. The capital, in his telling, is almost always downstream of the relationship, not the other way around.
The next time you get a no, resist the urge to file it away as final, and instead write down exactly what the investor said, since it usually holds real information about timing or fit. Send a thank-you note within a day or two that references something they specifically care about and offers them something useful for free, with no ask attached. Every couple of months after that, send a short, concrete update, a milestone hit, a new batch of users, real progress, not just a check-in. And keep including them in things that cost you nothing to share, a beta invite, a launch ticket, so the relationship stays warm long enough for the next real opportunity to say yes.
What You'll Achieve
The founder stops treating rejection as a closed door and starts treating it as the beginning of a longer relationship. Visibly, they build a habit of low-cost, value-first follow-up instead of disappearing after a no.
Turn a no into a slow yes
*Record what the no actually said*
When you get a rejection, write down exactly what the investor said, since it usually holds real information about timing or fit rather than a final verdict.
*Send a thank-you with no ask attached*
Within a day or two, send a note referencing something they specifically care about, and offer them something useful for free.
*Keep sending real updates*
Every couple of months, share one concrete piece of progress, a milestone, new users, real movement, not just a check-in.
*Include them at no cost*
Invite them to things that cost you nothing to share, a beta test, a launch ticket, so the door stays warm for the next real opportunity.
Reflection Questions
- What did this no actually tell me about timing, fit, or my pitch?
- Have I burned this bridge, or kept it warm?
- What value could I offer this person even if they never invest?
- Am I confusing a not now with a never?
Personalization Tips
- A freelancer turned down for a project stays in touch by sharing relevant articles, eventually landing a bigger contract months later.
- A job seeker rejected for a role keeps the hiring manager updated on new skills and gets called back for a different opening.
The Art of Startup Fundraising
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