Caution blind corner ahead

This summer, I attended the InsurTech Trails event held in Snowmass/Aspen, Colorado and organized by David Gritz and Stacey Brown. This was the second event like this that I've attended. On my way, I had a feeling that it was going to be fantastic, but I also thought it would be hard to measure up to the InsurTech Slopes event I attended in January of 2021.

These events are far different than any other industry event for several reasons, but the most notable are:

1. They are limited to a small group of founders and investors.
2. An entire day is spent on an excursion or two where you really get to know your fellow attendees—you see their micro fears and bravery—those interactions that are the ingredients to creating a very, very unforgettable and special bond.
3. The conference leaders make great effort creating valuable new connections and ensuring your challenges are brough to light when you want them to be, so you get the benefit of the group to help you solve them.

The stories and experiences I had the privilege of hearing about are remarkable and exactly the inspiration I need to keep pushing forward. I want to share all I gained from this experience with you.

Where else would I have had the chance to sit next to David Gritz and learn about how incredibly gifted he is at debating and the expertise he gained being part of a debate team in high school and college.

Where else would I get to see the gravity of an investor's responsibility monitoring and supporting their portfolio companies and being able to draw a correlation from that same investor's day-to-day responsibility with the natural leadership he demonstrated as he guided our entire group, twice?

Where else would I get the chance to sit next to a 32-year-old founder who asked me what I thought about the terms of a fractional executive agreement or the $30M offer he received after only starting his company six months prior?

Where else would I get to ask several founders about the qualities they look for in a co-founder and the terms of their arrangement to prevent anyone from getting burned—many, myself included, have a story of being burned.

David Gritz taught me to look at arguments and opposing views as a chance to be strategic and use techniques to ensure clarity and persuasion when it's the right thing to do. There is no ego in debating, and often, you're winning when your opponent believes they are.

Wait, what?!

My time spent learning from him and seeing him debate with another attendee the next day was priceless to me. The other attendee indeed thought he had won and I couldn't stop grinning all day.

Adrian Jones led the tour of Aspen and our hike. While we were walking downtown, he gave a good background of Aspen, but he also made it aspirational by talking about what it means to live there today. I'm so grateful I decided to go on that walk.

The next day, before our hike began, Adrian gathered us all around and ensured we knew what to expect and what to look out for. One of them being blind corners.

In that moment, he got me thinking about blind corners in life.

And the importance of surrounding yourself with people who can help you navigate life. No one asked Adrian to give us pointers and no one asked him to give us a tour of downtown Aspen.

He just did it.

To me, I believe that natural inclination to guide and to give everyone the most solid footing on their journey is what makes him one of the greatest and most trustworthy investors.

When we give from the heart, the value we receive in return is overwhelming.

I wanted to go on the entire hike that day, but I knew I couldn't. I had a lot to get done, but I didn't want to miss out on the little time I could spend hiking, so I went anyway with the understanding I might be taking an Uber back to the resort on my own.

Turns out, there was no solo ride back for me.

Stacey Brown and a couple of others had to leave early to finish up a few things for the event. It was the best 30-minute hike of my life. There was no FOMO for not finishing, I was simply on a different, equally as valuable, but shorter journey, and in the very best company. Our little crew was also very patient with my inability to stop taking pictures of flowers.

My time in Aspen ended beautifully, too, and with another moment of reflection. Here was this sweet couple enjoying the view and it reminded me of a very dear friend who's been looking out for me and insisting I take the time to enjoy the view. I am listening to his advice. I always listen to his advice. I hope you do the same.

ITC is the world's largest insurance gathering and there's so much value to gain from this event, but critically as important, is to attend smaller niche events to nurture those connections and build even deeper relationships.

At your next event, make it a point to stop and watch other people. Listen more than before. Draw the parallels to life lessons. They are there waiting for you to uncover them.

Life doesn't always give you an Adrian to point out that there are blind corners ahead, or a David to show you that what might seem like a tough conversation is actually an exciting time to strategize, or a Stacey who consistently demonstrates that he works just as hard as me and the path less traveled is actually sometimes my perfect path.

It's having experienced this once, seeing their incredible support and the support from our beautiful industry, that I've learned to never be afraid of a blind corner.

To you, great industry people, keep inspiring others and driving us forward. You are my inspiration and you make me proud of the sacrifices I've made. I hope to see you at InsurTech Slopes, January 30th-February 1st in Big Sky, Montana.

Or maybe you'll be even bolder and attend their event in Switzerland. Snowplowing down the mountain in Switzerland...what a dream for me.