Break Trail Ventures
Anywhere with Wifi, Boulder, CO, United States
Overview
Break Trail Ventures is an early stage venture fund based in Columbus, OH and Boulder, CO.
- Total investments
- 11
- Lead investments
- 1
- Investments · 12mo
- 1
- Active investors
- 1
Sector focus
- Finance
- Financial Services
- Venture Capital
Investment portfolio
- Orion
Participated · Seed · Nov 2025
Orion offers a smart mattress cover that continuously tracks a sleeper’s biometrics and automatically heats or cools specific zones to maintain an optimal temperature cycle throughout the night, aiming to improve both deep sleep and REM quality. The product combines embedded sensors with an AI engine that personalizes temperature adjustments for each individual. Seed funding proceeds will be directed toward expanding operations and widening the company’s market reach. Orion was founded by Harry Gestetner and Daniel Gestetner—entrepreneurs behind Fanfix and Byte—and joined by Blake Johnson and Scott Cohen, also from Byte. While the company has not yet disclosed revenue or user metrics, its founding team’s prior ventures recorded sizeable exits, indicating seasoned execution capability. Los Angeles, CA serves as Orion’s headquarters, giving the company access to both the region’s hardware talent and consumer-tech ecosystem.
- Thesis
Participated · Series A · May 2023
Thesis formulates customized nootropic supplements that target specific cognitive states using blends such as Energy, Clarity and Motivation. Its products use clinically studied active ingredients with high bioavailability and are manufactured to FDA cGMP standards. The brand emphasizes a digital-first, education-focused model and positions customization as its core differentiator in the wellness category. Founder and CEO Dan Freed developed the approach to help people optimize cognitive performance. Thesis has raised over $13.5M to date, including a recent $8.4M Series A and a prior $5.1M seed. The new capital will be used for key executive hires, product expansion and clinical trials.
- After.com
Participated · Seed · Jan 2023
After.com offers an internet-focused experience that enables families to pre-plan or arrange cremation and funeral services in minutes with simple, affordable, and transparent pricing. The company’s mission is to shift power to families experiencing loss while saving them time, money, and energy. After.com currently serves customers in Arizona, Southern California, Colorado, Oregon, Utah, and Washington. The business cites the U.S. death care market as a growing opportunity, with Spherical Insights valuing it at $27 billion in 2022 and projecting growth to $41 billion by 2032. After.com plans to use its recent financing to enter new markets, add talent across the organization, and further enhance marketing to support both pre-need and at-need business segments. After.com provides an internet-first experience for pre-planning and arranging affordable direct cremation and funeral services, allowing families to complete arrangements online in minutes. The company also offers funeral insurance and a tech-enabled approach to cremation, with a founding team that includes a fourth-generation funeral director alongside seasoned tech entrepreneurs. After.com expanded from a pilot in Phoenix to fully staffed operations in three states and four markets and says it has helped thousands of families. The business reported over 400% year-over-year growth in 2022. The company plans to use new funding to expand into additional states and markets nationwide and to build new products and services to help families navigate end-of-life. As of the close of the seed round, After.com has raised $5M in total capital.
- Expectful
Participated · Seed · Feb 2021
Expectful began as a guided-meditation and sleep app and positions itself as a go-to wellness resource for hopeful, expecting and new parents. Its core product remains a library of guided meditations and sleep content tailored to pregnancy and postpartum. The company grew to profitability and reports over 13,000 paid users with a free-to-paid conversion rate the company says is five times industry standards. Expectful’s revenue has grown 100% since March 2020. Under new CEO Nathalie Walton the company is pivoting in three phases—content, marketplace and community—to organize pregnancy information, digitize service providers (therapists, doulas, nannies) and build peer-reviewed listings with reviews. It has launched community offerings such as Mother Circles (six weekly video calls, a group chat and on-demand doula support) and is explicitly investing in Black maternal health outcomes while expanding content for non-gestational parents.
- Repeat
Participated · Seed · Aug 2020
Repeat analyzes customers’ à la carte purchase behavior to identify ideal reorder windows, then sends email or text nudges that link to a personalized, pre-filled "replenishment cart" customers can adjust and quickly checkout. The service is used by 67 CPG brands, including By Humankind, Jot, Vegamour, Youth to the People, Osea, Hydrant, Twice and Lemon Perfect. Repeat says its cart converts around 25% on average (some brands see 40–45%) and often yields checkouts in under 15 seconds. The company charges a monthly SaaS fee plus 5% of revenue driven by its cart, with tiered pricing (e.g., $99/month +5% for brands under 2,000 a la carte orders per month; $499/month +5% for brands over 10,000). Repeat is L.A.-based, was founded by Kim Stiefel and Sarah Wissel following their UNDR apparel experiment, and has not disclosed its own revenue figures. The startup plans to use new capital to hire across engineering, product, sales, marketing and growth, scale the business, and expand features such as QR-code entry points and a future universal/dynamic subscription experience. Repeat, formerly PRZM, offers a replenishment platform that analyzes customers' consumption patterns and sends personalized email nudges prompting repurchases. The reminders place suggested items back in shoppers' carts to remove friction from the replenish experience. The company pivoted from building a subscription brand to focusing on retention for other consumer packaged goods companies. Co‑founders Kim Stiefel and Sarah Wissel lead product and revenue strategy respectively. Repeat says demand has surged during the pandemic as ecommerce adoption accelerated; one client toilet‑paper brand saw a roughly 3,000x increase in conversions. The company recently raised seed funding to scale its product and go‑to‑market efforts.
Team
Jay Hirsh
Managing Partner
LinkedIn