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InsurTech Trails 2026

InsurTech Trails 2026

Founders + Investors Wilderness Forum — Lake Tahoe

June 23–24, 2026
South Lake Tahoe, CA
Invite-Only · Founders & Investors
Get Your Ticket — $895

Space is limited. Participation is curated.

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.

Lake Tahoe alpine scenery
Lake Tahoe — South Lake Tahoe, California

🎤 Curated Programming

Afternoon sessions on the decisions that define startup growth — from building a finance function to structuring deals to managing a board. Practical, peer-driven, and off the record.

🍽️ Private Dinner

An intimate evening at a curated Tahoe venue. The best conversations happen away from the agenda — this is where the real connections form.

🏔️ ATV Adventure

A full day on the trails. No specialized skills required — just a sense of adventure and a willingness to build relationships outside a ballroom.

Agenda

Two days of programming, dinner, and outdoor adventure

Day 1 — Tuesday, June 23
1:00 PM
Welcome + Founder & Investor Introductions
1:30 PM
Building a Finance Function: Seed to IPO Workshop
2:30 PM
Scaling a Sales Team from Founder to 10 Presentation
3:00 PM
Break & Networking
3:20 PM
Fireside Chat: Creating a Board That Works for 10 Years Fireside
4:00 PM
From One Business Model to Two: Software + MGA Presentation
4:30 PM
Fireside Chat: Day in the Life of a VC Fireside
5:00 PM
Table Topics
5:30 PM
Day 1 Wrap-Up
6:30 PM
Private Group Dinner Evening
Day 2 — Wednesday, June 24
10:00 AM
Departure from Margaritaville Lake Tahoe Resort
10:30 AM
Sign Waivers, Gear Up, and Head to the Trails
11:00 AM
ATV Experience Outdoors
12:30 PM
Group Lunch
2:30 PM
Return to Resort — Afternoon at Leisure
Wide shot of Lake Tahoe

What You’ll Get Out of It

Peer-Driven Insights

Sessions are designed for candid exchange — not polished keynotes. Expect real answers to the operational and strategic questions founders and investors are actually wrestling with.

Curated Connections

A small, intentional attendee list means every conversation is worth having. Pre-event coordination ensures you know who’s coming before you arrive.

Relationships That Last

Shared outdoor experiences accelerate trust in ways that conference halls don’t. After four years of these forums, the deals and partnerships made on the trails speak for themselves.

Time Away from the Noise

No sponsor booths. No keynote theater. Two days in one of the most spectacular natural settings in the country, focused on what actually matters.

What’s Included

Included in Program Fee ($895)

  • Day 1 afternoon programming
  • Private group dinner (Day 1 evening)
  • Day 2 ATV experience and transportation
  • Group lunch on Day 2
  • Curated attendee list and pre-event coordination

Not Included

  • Flights (RNO – Reno-Tahoe International, ~1 hr drive)
  • Hotel ($199/night at Margaritaville Resort — details sent upon registration)
  • Pre-arrival meals and activities
  • Incidentals and additional excursions

Who Should Attend

🚀
InsurTech Founders

Building and scaling startups

💼
InsurTech Investors

Active in the sector

⚙️
Operators & Executives

Leading growth-stage companies

🤝
Industry Leaders

Carriers, MGAs, and ecosystem partners

Past Investor Attendees

  • Allstate Strategic Ventures
  • AmFam Ventures
  • Anthemis
  • AXIS Capital
  • Cameron Ventures
  • ff Venture Capital
  • HSCM Ventures
  • IA Capital Group
  • Manchester Story
  • MunichRe Venture Partners
  • NFP Ventures (Distributed VC)
  • QBE Ventures
  • SiriusPoint Ventures

Venue & Getting There

Margaritaville Resort Lake Tahoe — 4130 Lake Tahoe Blvd, South Lake Tahoe, CA 96150. An all-suite resort on the Nevada border, steps from the lake and walking distance to entertainment and dining. Room rate is $199/night. Booking details are shared upon registration.

Recommended airport: Reno-Tahoe International (RNO) — approximately a 1-hour drive. All major rental car companies are available on-site. Rideshare is also available.

Margaritaville Resort Lake Tahoe — meeting room

Space Is Limited

To preserve the quality of interaction, participation is limited to a small, curated group. There are only so many ATVs on site — this is not a conference. It’s a community experience for InsurTech investors and founders. Apply early.

Register Now — $895

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