What is your customer's painful problem?


Trail Run Capital is a generalist firm, with a focus on Fintech, Enterprise SaaS, Marketplaces, and diverse founders.

These are some characteristics we look for:

  • Founders: Self-motivated, curious builders who care deeply about solving Big Problems & are able to think "outside the box."

  • Product: Whether a prototype or a fully launched product, we're excited about companies with increasing user growth, velocity, and user engagement.

  • Market: Trail Run Capital cares more about the number of people experiencing the painful problem and the team's execution ability than the existing market size. Great companies will expand markets over time.


The simplest parking management and enforcement solution

Esusu is the leading financial technology company providing data solutions for the low-to-middle income consumer

High protein, sustainable, and planet friendly dog snacks

A virtual networking platform helping community managers  

Banking built for startups

No-code rules engine for customer risk

Automation-driven cybersecurity (Acquired)

Qwick is an on-demand staffing as a service platform that connects the service industry

A new platform for 

analyzing, collaborating, and building with data

Calixa makes it easy to manage all your customers in one place

Discover and trade slow fashion in a welcoming community space

For busy professionals in sales and post-sales who need a more efficient workflow

Where creators run their business

Digital services for small businesses in Indonesia

API-first tax automation

High quality equipment and training

Building a new education system that takes kids seriously

Ultra customizable landing pages for serious e-commerce teams

Your favorite local treats, delivered

One platform to power your entire dental practice

- Jonathon Barkl, AirGarage Co-founder & CEO 
“Allison is a rockstar operator and has given us invaluable advice on growing and scaling AirGarage.”