Imagine if every casual conversation with a stranger turned into a sale of your product, or a headline in tomorrow’s news, or an $100,000 investment in your deal!

I learned this lesson in the most lucrative 10 minutes of my life, and it forever changed how I think about having a pitch ready at any time. In today's issue, I share my 100G story as well as:

Enjoy this uber cool ride…LG

In the early days of my first startup, we had managed to raise a quarter of a million dollars within the first 12 months to build our foundation. However, we were far from having a finished product or a sustainable business. We still needed more capital to keep the company afloat, and we were pitching our deal to anyone who would take a meeting. 

As we navigated the choppy waters of entrepreneurship, we began hitting roadblocks in raising additional funds.

One weekend, my business partner and a friend invited me to a "leadership conference" in San Antonio.

They thought it might be a good idea for us to step away from the office, hoping it would bring fresh perspectives on our business challenges.

Upon arrival, it became clear that this was not the typical business leadership gathering; it was a spiritual self-development event that talked about allowing the universe to happen for you. `

At the time, this type of conference was completely foreign to me. Hence, I gravitated to the back of the room, half paying attention but still hoping to glean something useful. At the very least, it would be a break from the fundraising grind.

I noticed another man with a similar demeanor sitting nearby. During breaks, we bonded over our shared experience of being brought there under false pretenses. We laughed at finding common ground in our unexpected situation, but also admitted what we actually liked about the event.

During one of the later breaks, we started talking about the Spurs NBA game happening that night in San Antonio. He and his companion were planning to go, and since we had already decided to try and scalp some tickets, he suggested we share a cab to the game to avoid the hassle of parking. I happily agreed.

At the end of the conference, we met outside and introduced each other to our respective parties before hailing a cab together. During the 10-minute ride to the arena, we chatted about the day's events and life in general. It wasn't until we were in the cab that he asked me what I did for a living.

In that moment, I was completely at ease, unaware of who this person was, and instead of launching into a pitch, I simply shared our story.

I spoke about our vision for the company and the experiences that inspired us to start it. I talked about the massive challenges we had faced, but also how each one taught us invaluable lessons. 

I mentioned how we had managed to get some big names involved with our company, including a few prominent Austin technology and business leaders. Their support didn't just lend us credibility; it helped us grow as individuals and as founders.

As we arrived at the arena, my new acquaintance handed me his card and suggested we meet up the next time he was in Austin. He said flippantly,

I laughed it off, not taking him seriously because we didn’t even really know each other. We went our separate ways to enjoy the game, and I forgot about the encounter after a few days.

A week later, I received an unexpected call from him. He was coming to Austin and wanted to take me to dinner. As an entrepreneur always open to a free meal, I happily accepted and met him at a local restaurant.

We talked for a while, and then he surprised me by saying he was serious about investing in my company. My jaw just about dropped, we REALLY needed the money at the time.

As I held that check from someone who had been a stranger just a week earlier and was now an equity holder in my company, I couldn’t stop smiling. Sometimes the universe really does surprise you in the best way.

The $100,000 cab ride taught me 3 crucial lessons when it come to always being open to opportunities (and ready for them):

#1. Treat Every Person as a Potential Stakeholder

Life has a funny way of presenting opportunities when you least expect them. That person sitting next to you on a plane, standing in line at a coffee shop, or sharing a cab ride could be your next investor, customer, or business partner. 

Shift your mindset: every conversation is an opportunity. Don’t wait for formal meetings; be open, curious, and willing to share your story in everyday interactions. That stranger could become a stakeholder.

#2. Have a Compelling Short Story Ready

I didn’t deliver a polished pitch. I simply relaxed and told a short story that was heartfelt and infused with my optimism about what was possible. That was enough to spark interest and build trust.

Even if you don’t have a story prepared, have a spiel ready to go that describes what you do, why it matters, and why you are so crazy committed to making it happen. Practice telling it until it feels natural and you don’t have to think about it. It just comes out. 

#3. Highlight Key Elements in Your Story

In your brief spiel (narrative), make sure to touch on elements that build credibility and showcase your potential:

By incorporating these elements, you create a story that not only informs but also inspires confidence in your listener. 

Remember, your story has the potential to open doors, create connections, and even secure investments. It’s great to be lucky as I was that day, but always remember this quote when you wonder how folks get so lucky:

In a 2024 national survey by Storyraise, over 250 nonprofit donors were asked what most influenced their decision to give. The result? Donors were 70% more likely to give when a compelling story accompanied the ask. Storytelling taps into emotion and makes abstract problems feel personal and urgent.

That’s why even a simple cab ride conversation, told with clarity and passion, led to a $100K investment. Stories don't just inform, they inspire action.

If you want to see what it looks like to be ready with a story/pitch, watch Willy Green bring the house down with his high-energy, conviction-packed pitch at the Startupfest: Winner "Best Pitch" Competition - Willy Green (Party on Demand).

In just minutes, he turns Party on Demand into a no-brainer. This is the level of passion and clarity every founder should aim for, whether on stage, in a meeting, or even in a cab ride.