High Trail Capital
High Trail Capital is a private investment management firm founded in 2019 that provides structured capital solutions—primarily senior secured convertible notes and equity investments—to small cap and early-stage public companies across multiple sectors via direct, relationship-based transactions.
- Company typePrivate
- Founded2019
- Headquarters—
- Headcount—
- GTM typeB2B
- OfferingServices
What High Trail Capital does
High Trail Capital is a privately held U.S. investment management firm, organized as High Trail Capital LP, that was founded in 2019 by Eric Helenek after a 20-plus-year career in middle-market investment banking. The firm pursues a flexible mandate and provides creative, structured capital solutions to small cap and early-stage public companies operating across a broad spectrum of sectors. Its core instruments are senior secured convertible notes, share purchase agreements, and direct equity investments, which it tailors to the specific financing objectives of each issuer.
The firm sources and executes transactions through direct, relationship-based engagement with management teams and boards of public companies, positioning itself as a non-traditional alternative to bank debt and primary equity issuance. Documented transactions include a $74 million convertible note participation in a $100 million Surf Air Mobility strategic financing (November 2025), a $43 million senior secured convertible note issuance to MicroVision tied to acquisition integration (February 2026), and a $27.5 million convertible note to Veraxa Biotech AG supporting a NASDAQ listing via a SPAC merger (May 2026). The team is led by Founder Eric Helenek and Partner Matt Goldberg, with Robert Glaubke contributing to content and market commentary on the firm's website.
Revenue mechanics are characteristic of a private investment partnership: returns are generated through interest on debt instruments, equity appreciation on conversion or direct stakes, and any transaction or structuring fees associated with capital deployment. The firm does not publicly disclose AUM, fund vintage, management fee rate, limited partner composition, or its own revenue, and it does not disclose a broad portfolio list beyond the named relationships, leaving the operating footprint concentrated among a small set of disclosed positions across Lidar technology, regional aviation, biotechnology, and oil and gas.
High Trail Capital firmographics
Firmographics- Name
- High Trail Capital
- Legal name
- High Trail Capital LP
- Website
- https://hightrailcapital.com
- Company type
- Private
- Founded year
- 2019
- Operating status
- Operating
- Short description
- High Trail Capital is a private investment management firm founded in 2019 that provides structured capital solutions—primarily senior secured convertible notes and equity investments—to small cap and early-stage public companies across multiple sectors via direct, relationship-based transactions.
- Ownership category
- akta.pro rank
High Trail Capital industry classification
Industry- Product category
- Investment Management
- NAICS
- Portfolio Management and Investment Advice (523940), Other Financial Investment Activities (5239)
- SIC
- Investment Advice (6282)
- akta.pro primary industry
- Large-Cap / Sponsor Finance Direct Lending (FSANADAJ)
- akta.pro secondary industry
- Capital Raising Advisory (Equity & Equity-Linked) (FSAEAGAC)
Keywords
High Trail Capital business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Technology or R&D, Marketing or Sales
Revenue model
- Investment Management & Capital Solutions: High Trail Capital generates revenue through providing structured capital solutions to small cap and early-stage public companies, including senior secured convertible notes, share purchase agreements, and equity investments. The firm likely earns returns through interest income on convertible notes, equity appreciation, and transaction fees associated with capital deployment.
Go-to-market motion1 record
Distribution channels1 record
Marketing channels2 records
High Trail Capital product offering
Product offeringCore offering
High Trail Capital is an investment management firm that provides structured capital solutions—including senior secured convertible notes, share purchase agreements, and equity investments—to small cap and early-stage public companies across a broad spectrum of sectors. The firm applies fundamental research and credit analysis to tailor creative financing arrangements that meet the specific financing objectives of portfolio companies.
Product overview
High Trail Capital is an investment management firm founded in 2019 that provides creative capital solutions to small cap and early-stage public companies across various sectors. The firm utilizes fundamental research, credit analysis, and structuring expertise with a flexible mandate to tailor financing to specific objectives. As an investment firm, it does not offer technology products or services; rather it provides financial instruments including senior secured convertible notes, share purchase agreements, and strategic financing arrangements to portfolio companies.
Differentiator
Problem solved
Functional benefit
Products and services
- Senior Secured Convertible Notes
- Share Purchase Agreements
- Equity Investments
Quantifiable outcome
- Successfully structured $43M convertible note financing for MicroVision to support acquisition integration
- +2 more outcomes
Companies that use High Trail Capital
Customer profileNamed customers4 records
Segments2 records
Ideal customer profiles1 record
High Trail Capital technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
High Trail Capital partnerships and signals
Strategic signalScale indicators1 record
Recent moves4 records
Expansion highlights4 records
High Trail Capital competitors and assessment
Company assessmentDirect peers
- Trinity Capital: Trinity Capital is a specialty lender providing senior secured loans, equipment financings, and structured debt to growth-stage and venture-backed companies. It is directly comparable to High Trail in providing bespoke debt solutions to underserved, non-investment-grade borrowers, with similar ticket sizes and structuring flexibility.
- Portman Ridge Finance: Portman Ridge Finance is a BDC that originates senior secured loans and invests in special situation opportunities in the lower middle market. Its willingness to underwrite complex credits and structured solutions aligns closely with High Trail's mandate.
- Runway Growth Finance: Runway Growth Finance is a business development company that provides senior secured loans to growth-stage companies. It shares High Trail's focus on flexible, relationship-based structured capital for companies that fall outside traditional bank lending parameters.
- WhiteHorse Finance: WhiteHorse Finance is a BDC focused on senior secured loans to lower-middle-market companies. Its emphasis on credit-quality borrowers and relationship-based lending parallels High Trail's approach to small-cap and special-situation credits.
- Stellus Capital Investment Corp: Stellus Capital is a BDC focused on direct lending to private middle-market companies. While its deal sizes are typically larger than High Trail's, the lower-middle-market private credit orientation and structured-deal approach make it a relevant comparable.
- Lincoln Park Capital Fund: Lincoln Park Capital provides equity capital and share purchase commitments to small-cap public companies — directly comparable to High Trail's share purchase agreement component and was co-invested in the Veraxa Biotech transaction alongside High Trail.
Broad incumbents
- BlackRock Capital Investment Corp: BlackRock Capital Investment Corp is a middle-market direct lending platform within BlackRock. While part of a much broader asset manager, its senior secured, sponsor-backed lending model is structurally similar to High Trail's senior secured convertible-note approach to small-cap credits.
- Marathon Asset Management: Marathon is a credit-focused alternative asset manager spanning direct lending, asset-based lending, and opportunistic credit. Its flexible mandate and structured-credit origination are conceptually comparable to High Trail's flexible small-cap credit strategy at a much larger scale.
- Oaktree Capital Management: Oaktree is a major global credit and private equity firm with strategies spanning performing credit, distressed debt, and special situations. While much larger and more diversified, Oaktree's special-situations strategy overlaps with High Trail's convertible-note and special-situations mandate at the small-cap end.
Emerging players
- Murchinson Ltd. Murchinson is a specialized alternative asset manager focused on small-cap and special-situations investments, including convertible securities. Its targeted small-cap mandate and use of structured credit instruments make it a close conceptual peer to High Trail, though at a different lifecycle stage.
Market position
Strengths4 records
Weaknesses4 records
Competitive moat4 records
Key risks6 records
Key highlights5 records
Customer concentration
High Trail Capital financial estimates
Financial estimateRevenue estimate
Valuation estimate
High Trail Capital leadership team
Management profileNumber of profiles
Profiles3 records
High Trail Capital funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
High Trail Capital M&A and investment
M&A and investmentM&A
Investments3 records
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about High Trail Capital
What does High Trail Capital do?
High Trail Capital is an investment management firm that provides structured capital solutions—including senior secured convertible notes, share purchase agreements, and equity investments—to small cap and early-stage public companies across a broad spectrum of sectors. The firm applies fundamental research and credit analysis to tailor creative financing arrangements that meet the specific financing objectives of portfolio companies.
Is High Trail Capital a public or private company?
High Trail Capital is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was High Trail Capital founded?
High Trail Capital was founded in 2019.
How does High Trail Capital make money?
One revenue line is on record: investment Management & Capital Solutions.
Who are High Trail Capital's main competitors?
Direct peers on record are Trinity Capital, Portman Ridge Finance, Runway Growth Finance, WhiteHorse Finance, Stellus Capital Investment Corp and Lincoln Park Capital Fund. Broad incumbents are BlackRock Capital Investment Corp, Marathon Asset Management and Oaktree Capital Management. Murchinson Ltd. is listed as an emerging player.
Does High Trail Capital have an API?
No public API is recorded for High Trail Capital.
What industry is High Trail Capital in?
High Trail Capital's product category is Investment Management. Its primary akta.pro industry code is FSANADAJ, Large-Cap / Sponsor Finance Direct Lending, with a secondary code of FSAEAGAC, Capital Raising Advisory (Equity & Equity-Linked). Its NAICS code is 523940 and its SIC code is 6282.