Starting your first fundraiser: what nobody tells you

When I started pitching to investors for the first time, the tech ecosystem gave me such a lot of sanitised advice like build the perfect deck, rehearse your vision, project absolute certainty.

What no one told me is that fundraising is less about corporate theatre and more about psychological boundaries.

When I launched Pioneering People, I knew I was addressing a fundamentally broken, traditional staffing model.

I had the data, the traction and the real-world proof that our platform solves an acute operational pain point. But the second you step onto the funding merry-go-round, you realise that an investor’s reaction to your pitch is not really a reflection of your business’s worth. I’ve had to learn – super quickly – how to navigate the boardroom without letting it rewrite my founder DNA.

If you are prepping for your first raise this summer, here is my take on what it actually takes to stay grounded:

• Separate business feedback from self-worth. When you’ve spent your twenties bleeding for your company, a VC challenging your unit economics feels like a personal interrogation. It triggers an immediate defensive reflex. I’ve learned to treat criticism as raw information, not an attack. If multiple investors raise the same technical concern, it’s not an insult – it’s a free diagnostic map of the leaks you need to plug.
• Investors are human (and humans get anxious). A “no” from an investor doesn’t automatically mean your strategy is flawed. Their decisions are governed by variables you can’t see from the outside: internal fund cycles, market timing, portfolio conflicts and raw emotion. Don’t let someone else’s investment mandate dictate your confidence.
• The best capital is close to the problem. Some of our earliest, most valuable angel investors didn’t wear the traditional VC badge. They were operators, executives and our actual customers. They backed us because they had experienced the friction of the staffing crisis firsthand and saw that Pioneering People actually fixed it. Look to the people who live the problem before you chase institutional capital.
• Funding is a tool, not validation. Startup culture has a tendency to treat raising capital as the finish line, but it isn’t. Investment is simply an administrative accelerator to help you build a sustainable machine. True validation doesn’t come from a term sheet; it comes from customers, revenue and solving a real problem.

My frontline data this month

• 📊 Pitches delivered: 8 
• 🚫 Structural rejections:  2 
• 🤝 Ongoing partner alignments: 4
• ☕ Lukewarm flat whites: Incalculable.

Every founder hears “no” more times than they expect (or want!) I’ve had to learn the trick of separating the noise from the constructive feedback and keep building my great business.

Rita Kastrati - Founder of Pioneering People

Rita Kastrati grew up in and around the hospitality industry, where she watched restaurants and bars struggle with employee shortages. Then, at university, she worked shifts for agencies, and saw a broken system that sold staff short. Now, Rita's reshaping the gig economy on her own terms as the trailblazing Founder and CEO of Pioneering People, a platform that connects businesses with verified workers instantly, while ensuring workers are paid fairly and on the same day.

Pioneering People

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