Sidecut Ventures

Sidecut Ventures Research Investment Thesis Sidecut Ventures is a pre-seed micro-venture capital firm founded by Mike Ma that invests in what it calls "coachable superheroes" — founders who are tackling systemic challenges in economic mobility, digital health, climate, and education, with FinTech as the central pillar. The firm's philosophy is distinctly operator-led: "coach first, capital second." Before writing a check, Mike Ma engages in a 30-day co-operating consulting role with the founding team, providing strategic, marketing, product, and storytelling coaching. This approach serves as both diligence and differentiation — Sidecut only backs founders who are genuinely coachable and open to ongoing feedback. The firm explicitly targets founders tackling "forgotten ugly problems" — high-impact challenges that are often overlooked by traditional venture capital because they serve underserved communities or address systemic inequities. Sidecut has a strong diversity thesis, with a track record of backing women-led and underrepresented founders, particularly in FinTech and digital health. Stage Focus Sidecut Ventures invests primarily at the pre-seed stage, with selective participation at seed and seed-plus extension rounds. The firm has led rounds as the sole institutional investor (e.g., Lily, Superfluent) as well as participated alongside other early-stage funds (e.g., Grifin, Health In Her HUE). Follow-on investments in existing portfolio companies are also part of the strategy, as evidenced by the oversubscribed extension seed in Simply Bail. Check Size Typical check sizes range from $5,000 to $375,000, firmly in micro-VC / angel territory. Post-money valuations at investment typically land around $3-5 million, consistent with pre-seed pricing for seed-stage companies tackling social impact areas. The range reflects the firm's ability to make conviction bets at varying scales, from small exploratory checks to meaningful lead positions. Lead Tendency Sidecut Ventures actively leads rounds, particularly at the pre-seed stage where the firm often serves as the sole institutional investor. Mike Ma has led the pre-seed rounds in Lily (AI voice hiring for frontline workers) and Superfluent (edtech), and made a $375K lead investment in STAG (EV tech) through The Pitch. The firm also participates as a co-investor alongside other angels and micro-funds. Recent Activity Sidecut Ventures formally launched Fund I, L.P. (incorporated in New York) with a first close announcement in early 2025 (SEC Form D filed December 2024). The fund is actively deploying capital: December 2025 : Investment in SoLo (SoLo Funds) — AI-powered community banking platform, first Black-owned fintech to reach 1 million users September 2025 : Follow-on in Simply Bail — bail bond management legal tech platform, oversubscribed extension seed round 2025 : Investment in Maro — mental health startup 2024 : Lead investment in Lily — AI voice hiring platform for blue-collar and frontline workers (UK) October 2024 : Investment in MoneyStack — behavioral health/financial counseling platform for sports betting addiction (pre-seed) 2024 : Investment in Elastic Energy — climate tech/clean energy startup 2024 : Lead of pre-seed in Superfluent — educational software startup 2024 : Investment in STAG — EV tech ($375K check via The Pitch) Prior : Investment in Grifin — micro-investing fintech app ($11M raised total) Prior : Investment in Health In Her HUE — digital health platform for women of color ($7.5M raised total) Portfolio Highlights SoLo Funds (solofunds.com): AI-powered community banking platform founded by Travis Holoway and Rodney Williams. The first Black-owned fintech to reach 1 million registered users; a certified B Corp. Members borrow, lend, and bank with no mandatory fees. MoneyStack (moneystack.com): First-of-its-kind HIPAA-compliant platform addressing financial distress from gambling addiction. Integrates financial counseling into behavioral health care treatment. Pittsburgh-based, Techstars Economic Mobility Accelerator 2023 alum. Lily (teamlily.ai): AI-powered voice hiring platform for blue-collar and frontline workers in care, hospitality, and healthcare sectors. Founded by Philip and Tom Mundy (multi-exited entrepreneurs). Transitioned from product launch to significant revenue within 30 days; traction in UK with expansion to US and Latin America. Sidecut was sole institutional investor at pre-seed. Grifin (grifin.com): Micro-investing app that automatically invests $1 in retailer stock each time a user shops there. ~500,000 registered users; raised $11M total including Series A (Nava Ventures lead). Health In Her HUE (healthinherhue.com): Digital health platform connecting Black women and women of color to culturally competent healthcare providers. Founded by Ashlee Wisdom; raised $7.5M total; partners include Johnson & Johnson Impact Ventures. Simply Bail (simplybail.com): Bail bond management software for agencies — GPS check-ins, court reminders, payments. Legal tech applying technology to the justice system. Follow-on from Sidecut in oversubscribed extension seed. Team Mike Ma — Founder & Managing Partner Mike Ma is a Harvard-educated operator-investor who has built his career at the intersection of FinTech, marketing, and venture. Prior to founding Sidecut Ventures, he served as: CMO at Betterment — one of the largest robo-advisory platforms; helped scale a category-defining fintech CMO at Own Up — digital mortgage marketplace Managing Director at Nex Cubed — launched the inaugural FinTech accelerator and the HBCU Founders Fund, expanding access to capital for Black founders Operating Partner at Sway Ventures — overseeing FinTech investment activity Co-founder of ShredBetter — outdoor sports startup, acquired Strategy/marketing roles at kasina and Coeio (both acquired) Digital innovation at Bank of America and $60M brand campaign leadership at Vanguard Mike resides in New York and Vermont. He is a panelist at FinovateFall 2026 discussing open banking and AI in financial services. Geographic Focus Primarily United States, with exposure to UK (Lily) and Canada. The firm has invested in companies based in Pittsburgh, Los Angeles, New York, and the UK, reflecting a geography-agnostic approach within the English-speaking world, with US domestic focus. Decision Process Sidecut operates as a solo GP fund with Mike Ma as the primary decision-maker. The firm's unique diligence process — the 30-day co-operating consulting engagement — means that the decision to invest is organic and relationship-driven rather than committee-driven. Founders pitch at sidecut.vc/pitch-us. Founder Preferences Sidecut backs founders who are: Coachable : Open to feedback, willing to iterate on their narrative and strategy Mission-driven : Tackling systemic problems in health equity, economic mobility, climate, or education Operator-like : Demonstrate strong execution instincts and customer focus From underrepresented backgrounds : The firm has a proven track record with women-led and HBCU-connected founders Sidecut explicitly avoids founders who are not open to coaching or who are focused on high-competition, well-capitalized spaces. The fund targets the overlooked — the "forgotten ugly problems" with large addressable markets and low VC competition. Fund Details Sidecut Ventures Fund I, L.P. — incorporated in New York, first close announced in early 2025 with SEC Form D filed December 2024. Fund size is undisclosed, consistent with a micro-VC strategy. The fund has made approximately 22-31 investments to date.