Rejected 100 Times? Why Resilient Founders Still Win

Dear Founder,

All of us love the headlines about term sheets, oversubscribed rounds, and investor hype.

But what rarely gets the spotlight? The silence. The polite “no.” The 99th pitch that ends in “we’re not sure there’s a market here, please keep in touch.”

Here’s the hard truth- every founder worth remembering has a long rejection arc; often 50, 100, or more before something breaks through. It rarely works straight out the gate and that’s okay. No first idea makes it big untouched. Every breakout success in the world’s history has been shaped by the market, questioned by investors, and pressure-tested before it really hits.

So friends, rejection isn’t failure. It’s fuel. It strips ego and sharpens vision. And sometimes, it’s exactly what founders need to build something unshakable.

Resilience isn’t optional. People invest in your company’s’ traction last, your tenacity first. There are founders whose products we today use extensively and whom we read about in the media. But it wasn’t always smooth sailing, they stayed put and turned a wall of “no” into billion-dollar resilience.

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Case Study 1: Tope Awotona – Calendly

When Tope Awotona set out to build Calendly, he heard "no" on loop. Investors just didn’t see the vision. A scheduling tool wasn’t “sexy.”

Tope was a Nigerian-born founder in Atlanta, pitching to a Silicon Valley crowd that didn’t quite get him or his product. His background didn’t fit the stereotypical pattern investors loved. So, the capital didn’t come.

Instead of folding, he bet on himself:

• He emptied his savings and maxed out credit cards to fund Calendly’s early development.
• He focused on one thing only: user pain—solving the back-and-forth of scheduling with elegance and simplicity.
• He built slow, smart, and lean—with zero venture capital.

By the time investors came knocking, Calendly was profitable and scaling fast through pure product-led growth. In 2021, he raised $350M, valuing the company at $3B+.

What happened here? Rejection didn’t delay success. It kept the company focused and customer-driven. The “no” brought him clarity, not just cash.

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Case Study 2: Shan-Lyn Ma – Zola

Shan-Lyn Ma, co-founder of Zola, didn’t have it easy either.

She entered one of the least exciting categories in tech, creating wedding registries. Investors weren’t lining up to fund innovation in a space dominated by legacy players like Bed Bath & Beyond or The Knot. Ma’s idea was to reimagine wedding planning for a modern generation, integrating registry, planning tools, and ecommerce into one sleek experience.

Investors? Unconvinced.

She pitched over 70 times. The rejections weren’t brutal—they were worse: polite and indifferent. “Not a big enough market.” “Is this really a tech company?” “E-commerce and weddings are hard.”

These hiccups in her journey didn’t deter her and she kept refining her product and proposition for her customers:

• She built an MVP anyway, pulling in early users with a simple, beautiful experience.
• She listened to couples, not investors. What they wanted was clear and no one else was delivering it.
• She bootstrapped until momentum was undeniable, then raised from investors who truly got the vision.

Zola is now used by over 2 MN+ couples, with revenue in the hundreds of millions and a reputation as one of the best modern consumer brand builds of the last decade. And Ma did it by ignoring early indifference and trusting the market instead.

What happened here? Rejection is often a misunderstanding of vision. So, don’t change the idea but change how you perceive yourself & your idea and how you communicate this with conviction to the world. Also, it’s important to prove your idea’s worth with kickass execution aka traction. Simply put, there’s strength in rejection if you’re willing to extract it.

To summarize, what 100 “no’s” give you, one easy “yes” never will:

• Sharper storytelling: If your pitch doesn’t land, you’re forced to refine it. Again and again. Until it does.
• Customer-first mindset: When capital is tight, you focus on real users and real revenue. That’s where the magic happens.
• Internal conviction: You stop chasing investor excitement and build from deep belief instead.

Start-ups that survive rejection tend to scale better later. They’re leaner, clearer;  often more in control of their future and 100x better prepared for the moment the right "yes" shows up.

Let’s build. Not because success is guaranteed but because you believe in what you’re building. We’re rooting for you!

Love,
Team Hygriv

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P.S. Warm hug to the Founders Still in the Trenches

If you’re getting polite declines or ghosted altogether, welcome to the club. We hear it every day. You’re in good company. Some of the most enduring companies of the last decade were pitched into silence, told no, or outright dismissed. That didn’t stop them. It made them. So keep going.

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