Matchstick Ventures

Matchstick Ventures is a Boulder and Minneapolis-based venture fund that backs ambitious founders in the North and Rockies regions — the parts of the US that sit between the coasts. Founded in 2015 by Ryan Broshar, a former Techstars Minneapolis Managing Director, the firm has grown from its roots as a regional early-stage investor into a significant regional player with over 100 portfolio companies and $90M+ total capital raised across three funds. Natty Zola, former Managing Director of Techstars Boulder and founder of Everlater (sold to AOL in 2012), joined as a partner in 2019.

This guide covers Matchstick Ventures's investment thesis, check sizes, portfolio highlights, and practical advice for founders considering pitching the firm. Whether you're building in Minneapolis, Denver, or another non-coastal market, understanding Matchstick's specific approach will dramatically improve your chances of getting a meeting.

Matchstick's founding team brings something unusual to VC: both partners have been in the arena. They've been startup founders, run accelerator programs, and invested across multiple market cycles. That operational background shapes how they work with portfolio companies — it's not passive支票 writing. If you're raising from Matchstick, you're getting investors who have coached founders through exactly the challenges you're facing.

The firm is currently deploying Fund IV, with a $500K–$1.5M check-writing range for pre-seed and seed-stage companies. Their thesis has broadened over time to include AI-native applications and infrastructure, while maintaining core conviction around B2B software, fintech, and vertical SaaS.

If you're building between the coasts and want a lead investor with Midwest roots and genuine operator experience, Matchstick Ventures belongs on your target list. Here's how to approach them effectively.

Matchstick Ventures invests in ambitious founders building scalable technology companies in the North and Rockies — meaning the Midwest, Mountain West, and Canadian markets that coastal VCs often overlook. Their core thesis centers on the non-coastal US having a deep pool of world-class founders building in large markets, but suffering from a relative lack of institutional capital willing to lead rounds.

The firm is sector-agnostic but has identifiable weightings. B2B SaaS has historically dominated the portfolio, along with fintech and marketplace businesses. More recently, Matchstick has been building conviction around AI-native companies, with recent investments including Cast Finance (AI accounting automation), Pageport (AI-native CRM), and Freeplay (AI infrastructure). The common thread across all sectors is software that solves real operational problems for businesses.

What distinguishes Matchstick's thesis is the geographic angle. The firm argues that non-coastal companies face less competition for talent, can achieve meaningful traction on smaller budgets, and often develop durable competitive moats by being closer to their customers in industries like agriculture, manufacturing, logistics, and healthcare that are concentrated outside major coastal metros. The fund thesis has evolved to include AI adoption plays, but the geography-first framing remains.

Matchstick typically leads or co-leads rounds, and prefers to write checks between $500K and $1.5M. Their sweet spot is companies that have found initial product-market fit and are ready to use a significant capital injection to scale — not pre-revenue ideas still being validated. They do invest at pre-seed, but the bar for pre-seed deals is high and typically involves a warm intro from a trusted ecosystem participant.

Matchstick Ventures has raised four funds, each meaningfully larger than the last. Fund I in 2015 was a $5M vehicle, allowing the firm to write $100K–$250K checks and establish early credibility in the Minneapolis ecosystem. Fund II closed at $30M around 2018–2019, expanding check sizes to $500K–$1M and broadening the portfolio's sector and geography scope. Fund III, a $55M fund raised in September 2021, gave Matchstick the flexibility to write up to $1.5M checks and compete for seed-stage deal leadership in the region.

Fund IV is currently active, maintaining the $500K–$1.5M range while increasing deployment speed in AI and infrastructure-adjacent companies. The September 2021 timing of Fund III meant the firm was deploying capital through the 2021 boom and has been more selective through the 2022–2024 correction, though they remain active and have made multiple investments in 2024 and 2025.

Matchstick's fund progression reflects both the success of early portfolio companies (which generated follow-on interest and awareness) and the broader maturation of the Midwest venture ecosystem. When Matchstick started, a $5M fund for Midwest early-stage was considered unusual. Now, regional funds of that size are common, and Matchstick is recognized as one of the anchors of the Colorado-Minnesota axis.

For founders, the fund size context matters: Matchstick is not a micro-VC writing $50K checks. They are structured to lead rounds and provide meaningful capital, but their check is not sufficient to run a full Series A. If you're raising a $3M round, Matchstick might be your lead — if you're raising $15M, you likely need a combination of investors or a different lead.

Matchstick Ventures has remained actively deployed through 2024 and 2025 despite a tougher venture market. Recent investments include Juno (travel and expense management, June 2025), Cast Finance (AI-powered accounting automation, May 2025), Pageport (AI-native CRM, March 2025), and LaunchBay (developer onboarding platform, December 2024). These investments show a clear shift toward AI-native applications, with Matchstick explicitly building thesis around artificial intelligence adoption in the enterprise.

The firm has also continued to back existing portfolio companies. Inspectorio, a supply chain visibility and quality management platform, raised a $50M Series B — a significant milestone for a Matchstick Fund I portfolio company. Warmly, an AI-powered revenue intelligence platform, secured a $6M Series A+ led by RTP Global, showing Matchstick's ability to help portfolio companies attract outside lead investors for growth rounds.

Other notable recent investments include Fiveable (edtech community platform), which has built a substantial audience of high school students preparing for AP exams and college, and Tilt (HR and benefits infrastructure), which reflects Matchstick's continued interest in infrastructure tooling for small and medium businesses.

The overall cadence suggests Matchstick is investing 8–12 new companies per year, with a bias toward companies that have crossed an early traction threshold — meaningful revenue, clear retention metrics, or product-market fit indicators — rather than pure pre-revenue concept-stage deals.

Matchstick's portfolio spans more than 100 companies across multiple sectors. The most well-known portfolio companies illustrate the breadth of the firm's thesis and the operational maturity of its investments.

Inspectorio, founded in Minneapolis, has grown into a global supply chain visibility platform with a $50M Series B. The company addresses quality management and compliance for manufacturers and brands — a deeply unsexy but massive market that required deep operational expertise to navigate. Matchstick backed Inspectorio at Fund I, and the relationship illustrates how early conviction on a founder in a non-obvious sector can generate outsized returns.

Spekit, based in Denver, is a digital adoption platform that helps enterprises onboard and train employees on software tools. The company raised significant growth capital and has built a blue-chip customer base. Spekit's trajectory reflects Matchstick's thesis that B2B software solving real operational problems in non-coastal markets can scale efficiently.

Upsie, a Minneapolis-based smartphone and electronics warranty platform, has disrupted the traditional warranty model by selling directly to consumers at a fraction of traditional retail warranty prices. The company's growth and SaaS unit economics demonstrate strong product-market fit in a category that coastal VCs largely ignored at formation.

StackHawk, a Denver-based API security testing platform, raised multiple rounds including a Series B and represents Matchstick's conviction in developer tooling and cybersecurity. Fiveable, an online learning community for high school students, built a devoted audience of over 1 million students and raised significant growth capital. Branch provides infrastructure-as-a-service for internet businesses, and Base (acquired by @Properties) demonstrates Matchstick's willingness to back vertical SaaS in real estate.

Notable exits include AddStructure (acquired by Bazaarvoice), Adhawk (acquired by Fleetcor), and several other trade sales that have returned capital to early Matchstick funds. Notion, Ramp, and Veho appear as companies that came through the Matchstick or Techstars network — the firm's alumni network is extensive given the partners' time as Managing Directors of flagship accelerator programs.

Matchstick's founder criteria starts with a simple question: is this person going to be able to execute at a world-class level when things get hard? Both partners have worked with hundreds of founders through Techstars, and they've seen the patterns that separate founders who can navigate hypergrowth from those who can't.

The firm looks for founders with domain expertise in whatever sector they're operating in — not necessarily a previous founder exit, but deep operational knowledge of the problem they're solving. A fintech founder should have worked in financial services. A vertical SaaS founder should understand the specific industry workflows intimately. The days of 'rockstar coder can learn any domain' being a sufficient pitch are long gone for Matchstick.

Beyond domain expertise, Matchstick evaluates founder coachability and self-awareness. The firm's operational model means they'll be involved in your company, often as a board member or observer. They want to work with founders who can hear hard feedback, integrate it quickly, and still maintain the conviction to push through noisy data. Natty and Ryan have both been in the chair — they know the difference between a founder who is genuinely listening versus one who is performing receptiveness.

For the company, Matchstick looks for evidence of product-market fit — not necessarily large revenue, but clear engagement signals, retention data, and ideally some NPS or referral metric that shows customers value the product. They prefer companies that have found a wedge use case and can articulate exactly who uses the product, what job they're hiring it for, and what the alternative is.

Geographic patience is a feature of Matchstick's approach. They won't penalize you for being in Minneapolis or Boulder versus San Francisco, and they actually view non-coastal markets as an advantage in terms of talent cost, customer proximity, and competitive intensity. If you're building in a non-coastal market with a strong regional story, that is a positive in Matchstick's eyes, not a negative.

The highest-signal path to Matchstick is a warm introduction from a portfolio founder, a Colorado or Minnesota investor who knows the firm, or a Techstars alumni network member. Ryan and Natty are deeply embedded in both ecosystems, and their investment decisions reflect the credibility signals that come from trusted referrals within those communities.

If you don't have a direct connection, the second-best path is a referral from another investor who has a relationship with Matchstick. The firm tracks inbound deal flow carefully, and deals that come with a recognized investor name attached get priority review. This isn't unique to Matchstick — it's how most early-stage funds operate — but it's especially pronounced at a firm with a strong regional identity.

Cold outreach through the Matchstick website is less effective but not a dead end. If you're going to cold outreach, the email should be short (under 200 words), reference why Matchstick specifically, and lead with the problem and traction rather than the solution. The team has seen thousands of pitches and can spot a mass-email template instantly. Make it specific.

When you get a meeting, come prepared with detailed financial models, clear answers about your SaaS unit economics, and a realistic assessment of your competitive landscape. Ryan and Natty will both dig into the financials and challenge your assumptions — not to intimidate you, but because they've both built and sold companies and know which questions reveal whether a founder truly understands their business.

Follow-up discipline matters. Matchstick typically takes 2–4 weeks from initial meeting to decision, and the firm's deal flow means they're often juggling multiple processes simultaneously. A polite follow-up at the two-week mark is appropriate; being a pest is not. If you have a competing term sheet or an urgent timeline, communicate it clearly — the firm respects founders who know their position in the market.

Matchstick Ventures invests in early-stage companies, but they expect founders to have a firm handle on their financials. This means knowing your burn rate, runway, SaaS unit economics, and path to profitability or the next milestone that justifies a higher valuation. The firm has seen enough pitch decks to know when a founder is papering over gaps in understanding with vague growth projections.

For pre-seed and seed companies, investors want to see that you understand your customer acquisition cost (CAC) and lifetime value (LTV/CAC ratios), and that you have a realistic plan to improve LTV:CAC ratios over time. If you're SaaS, show net revenue retention. If you're marketplace, show take rate and liquidity metrics. If you're fintech, show the revenue per user and cost to serve. Each business model has specific financial mechanics — mastery of yours is the baseline expectation.

Working with a fractional CFO is particularly valuable for pre-revenue or early-revenue companies preparing for a Matchstick raise. A fractional CFO can build investor-ready financial models that contextualize your current traction within a credible growth trajectory, help you stress-test your assumptions before an investor does, and ensure your data room is organized for due diligence. If your numbers are unclear or inconsistent, investors will assume the company has bigger problems.

Financial projections should be grounded in historical data, even at the earliest stages. If you have three months of revenue, show three months. If you have ten enterprise pilots, show conversion rates from pilot to paid. Matchstick will challenge your projections aggressively — being able to explain the basis for your forecasts with data (even small datasets) is far more compelling than a hockey-stick projection with no grounding.

Whether you're preparing to pitch Matchstick Ventures or any other early-stage investor, having investor-ready financials and a coherent growth narrative can be the difference between a first meeting and a term sheet. Our team has helped numerous companies in the pre-seed to Series A stage raise capital with confidence.

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Finding the right investor for your startup is one of the most consequential decisions you'll make as a founder. Take the time to research potential investors, understand their portfolio thesis, and build relationships before you need capital.

Our guides cover regional anchor funds like Matchstick Ventures as well as major national investors, with detailed analysis of firm-specific preferences and deal criteria.