InsurTech Trails 2026
InsurTech Trails 2026
The next InsurTech Trails experience heads west to the breathtaking shores of Lake Tahoe. Join an intimate group of founders, operators, investors, and industry leaders for two days of meaningful connection, curated conversations, and outdoor adventure—far from the noise of traditional conferences.
Set against the crystal-clear waters and alpine peaks of South Lake Tahoe, this is where real relationships are built. Step outside the ballroom and into an environment designed to foster authentic dialogue, fresh thinking, and lasting partnerships.
Pre-Arrival
Monday, June 22
Arriving early? An optional, self-organized evening in South Lake Tahoe for those in town the night before can be a great way to break into the event.
All registered attendees will be connected via a group chat prior to arrival to discuss restaurants, activities, and informal meetups.
Agenda Day 1
Tuesday, June 23
OFFICIAL PROGRAMMING (subject to change)
1:00 – Welcome + Founder & Investor Introductions
1:30 – Workshop: Building a Finance Function: Seed to IPO
2:30 – Presentation: Scaling a sales team from a founder to 10
3:00 – Break / Networking
3:20 – Fireside Chat: Creating a Board That Works for 10 Years
4:00 – Presentation: From one Business Model to Two (Software + MGA)
4:30 – Fireside Chat: Day in the Life of a VC
5:00 – Table Topics
5:30 – Wrap-up
Evening
6:30 – Private Group Dinner
An intimate dinner experience at a curated Tahoe venue—designed to deepen connections and continue conversations in a relaxed setting.
Agenda Day 2
Wednesday, June 24
A full day dedicated to relationship-building through shared experiences in the outdoors.
10:00 – Departure from Margaritaville Lake Tahoe Resort
10:30 – Sign waivers, get gear, and head to the trails
11:00 – ATV Experience
12:30 – Group Lunch
2:30 – Return to resort
Afternoon at leisure or optional small-group meetups before departures.
Venue
Margaritaville Lake Tahoe Resort offers a vibrant yet relaxed setting in the heart of South Lake Tahoe—just steps from the lake, trails, and outdoor activities that define the region.
Room rate is only $199/night. This all-suite resort offers incredible ammenities and is on the Nevada border, and is walking distance to various entertainment venues. Booking details will be shared upon registration
Additional Program Details
Included in the program fee:
Day 1 afternoon programming and private dinner
Day 2 activities, transportation, and lunch
Curated attendee list and pre-event coordination
Not included:
Flights (RNO – Reno-Tahoe International Airport is recommended, ~1 hour drive)
Hotel accommodations
Pre-arrival activities and meals
Incidentals and additional excursions
Space is Limited
To preserve the quality of interaction and experience, participation is limited to a small, curated group of attendees. In addition, there are only so many ATVs available at the experience location, so don't miss out!
This is not a conference—it’s a community experience for InsurTech investors and founders.
Apply early to secure your spot.