Okay, so the popcorn is back in the pantry and I've managed to grab some mint chocolate chip cookies from Insomnia Cookies. On this one, let's unpack my first investor pitch.
The Scene:
Picture this: I had a polished pitch deck, conservative financial projections, and a prototype ready to go. A broker had set up a meeting with an angel group, and thanks to my extensive Shark Tank viewing experience, I thought I was prepared for anything.
My venture? An AI-powered platform designed to mitigate risk and revolutionize the shared workspace industry. With bootstrapped funding and a growing buzz among coworking insiders, I felt unstoppable as I logged into the Zoom meeting.

My potential investor, let's call him Andrew, joined the call from what looked like a WeWork office. As a 14-year industry veteran, I immediately felt at ease. I was in my element.
The Train Wreck:
Twenty minutes on the clock. I pitched my heart out, made my ask, and braced for questions. But it turned out this angel group knew next to nothing about coworking. Their questions missed the mark, focusing on growth details instead of the venture deal and the return on their investment.
I tried to cram 14 years of industry knowledge into a 10-minute Q&A. Let's just say I "nerded out."
The Turning Point:
Midway through my jargon-filled ramble, I realized I'd lost them. In a desperate attempt to regain their attention, I bombarded them with industry stats and SuddenlySpaces market projections. I even cracked a few jokes (which fell flat). Nonetheless, that Zoom call ended, and so did my confidence.
Did I close the deal? Nope. Did I feel like a complete failure? Absolutely. But here's what I learned:
- Humanize Your Investor: Ask how they are doing and acknowledge that their time is valuable.
- Ask Questions: Starting a call by getting background on who is sitting across from you and what deals they typically invest in, will help you tailor your pitch and what to focus on.
- Simplify, Simplify, Simplify: Complex ideas need to be broken down into digestible chunks.
- Embrace the Unexpected: Things will go wrong. Laugh it off and keep going.
- Failure is Fuel: Every setback is a chance to learn and grow. Just don't change who you are or your venture for each investor.
Since that fateful pitch, I've evaluated over $3 million in term sheet offers, securing $625,000 in funding. I have an incredible team of advisors who keep me grounded and focused. And most importantly, my pitch now clearly communicates the disruptive potential of SuddenlySpaces.
So, if you're an investor who appreciates a passionate, resilient, and slightly quirky founder with a game-changing idea, reach out! We're not just looking for investors; we're looking for strategic partners who can help us transform the PropTech space.
Popcorn on the next one and I'll share lessons and the tale of pitch to friendship from my first VC pitch.