Matchstick Ventures

Matchstick Ventures: Founder-First Early-Stage Investing in North America Investment Thesis Matchstick Ventures is predicated on a powerful belief: world-changing companies can be built anywhere, not just in traditional tech hubs. Founded in 2015 by Natty Zola and Ryan Broshar—both serial entrepreneurs who exited their own companies—Matchstick invests in ambitious, underdog, and diverse founders in underserved startup ecosystems, primarily in the Rockies (Colorado) and the North (Minnesota). Their thesis centers on "founder-first" relationships: they believe they work for their founders, not the other way around. Having started and scaled companies themselves, they understand the founder journey intimately and commit to being the first call when things get tough—providing not just capital but camaraderie, connections, and community. Core Values and Operating Philosophy Matchstick's operating philosophy is encoded in their values system: Work hard, play hard, give back - Life is short; do big things with joy and give without expecting return Do the right thing - Reputation is paramount; always be proud to look yourself in the mirror 4H - Happy, honest, hungry, humble Play the long game - Think beyond momentary optimization to long-term relationship implications This philosophy manifests in their approach: they flip the traditional VC script by believing they serve the entrepreneur, not vice versa. They provide four core pillars: Capital : Pre-seed and seed investments of $500K-$1.5M Camaraderie : Hands-on support, trustworthy relationships, always in your corner Connections : 400+ "Matchstick Strikers" (entrepreneurs, operators, corporate partners) available for mentorship and introductions Community : Building fellowship around their companies to combat startup isolation Investment Focus Geographic Scope Primary : Colorado Rockies region and Minnesota North region Secondary : Broader Techstars network ecosystems across North America Physically based : Boulder, CO and Minneapolis, MN with multi-location team Stage Preferences Pre-seed : $500K-$1M for teams with ideas or early prototypes Seed : $1M-$1.5M for teams with product-market validation Reserve fund participation : 50% reserves for follow-on investment in later rounds Matchstick leads or co-leads most investments, demonstrating high conviction and hands-on involvement. Sector and Model Diversity Matchstick's 140+ company portfolio reflects remarkable diversity across sectors: Enterprise & B2B Software (developer tools, B2B procurement, AI/LLM infrastructure, healthcare tech, workforce technology); Consumer & SMB (e-commerce solutions, real estate tech, travel & hospitality); Marketplace & Services; and Emerging Tech (AI agents, security, blockchain, climate). Team & Expertise The Matchstick team combines founder experience, accelerator leadership, and deep ecosystem knowledge: Natty Zola (Partner, Boulder, CO) - Founder of everlater.com (sold to AOL 2012), former MD of Techstars Boulder, advisor to 200+ founders Ryan Broshar (Partner, Minneapolis, MN) - 3x founder with 2 exits, former MD of Techstars Retail Accelerator, founder of Beta.MN and Twin Cities Startup Week Nicole Glaros (Venture Partner, Boulder, CO) - "Employee #1" at Techstars, helped scale to 50+ programs and $77B market cap, multi-unicorn backer (joined May 2025) Shannon Shroyer (Head of Network, Minneapolis, MN) - Manages 200+ network relationships, brings atypical VC background Additional resources: 100+ top-tier co-investors, 100+ fellow founders, subject matter experts across industries. Fund History & Capital Deployment Fund II : $30M closed ~2019-2020 Fund III : $55M closed ~2021 Fund IV : Currently deploying actively Deployment pace shows 3 new investments in last 12 months (Dec 2025). Recent Investment Activity (2024-2025) Matchstick invests across diverse verticals: Oct 2025: Automate.Clinic (AI healthcare) Jul 2025: Paperstack (fintech working capital) Jun 2025: Locate.ai (CRE tech) Jun 2025: Juno (travel & expense) May 2025: Cast Finance (AI accounting) Mar 2025: Pageport (AI-native CRM) Dec 2024: LaunchBay (onboarding) Notable portfolio milestones: Zed raised $42M+ with Sequoia Series B, Reema Health $19M Series B, Branch partnership with Union Square Hospitality. Decision Process Structure : Partnership model (collaborative decisions) Timeline : 2-4 weeks typical Warm intros : Preferred but not required Due diligence : Deep founder/team focus, product evaluation, market sizing Portfolio & Exits Current portfolio exceeds 100+ active companies. Notable exits: everlater.com (AOL), Branch (payment enablement), Kipsu (hotel tech). Scale achievements: Zed ($42M+ Series B), Warmly ($17M+), Intelligems ($9M+). Lead Tendency and Involvement Leads or co-leads most investments Board seats, advisor roles, deep operational involvement 50% reserves for follow-ons Deep bench of top-tier co-investors Values & Community Impact Beyond investing, Matchstick demonstrates diversity commitment, community building (Twin Cities Startup Week, Beta.MN), transparency, and Pledge 1% membership. Differentiated by local ecosystem embeddedness, founder-first culture, operational depth, long-term relationships, and network density. Fund Status Current status : Actively deploying Fund IV Check sizes : Maintained $500K-$1.5M range Thesis shift : Increasing focus on AI adoption (Freeplay, Freedev.ai, Cast Finance, Locate.ai) Founder focus : Repeat founder backing and operator networks