Natty Zola
Partner @ Matchstick Ventures
Boulder, United States
Natty Zola is a partner at Matchstick Ventures. Previously Natty was the Managing Director for Techstars Boulder and Head of Consumer Products for MapQuest, where he helped MapQuest return to profitability and year-over-year growth for the first time since 2007. Before MapQuest, he was a founder of Everlater.com, a travel blogging platform and CRMsystem for tour operators, that participated in Techstars in 2009 and was acquired by AOL in 2012. He also graduated from GE's Financial Management Program and worked with Jim Collins on the best selling books "Great by Choice" and "How the Mighty Fall." Natty is passionate about helping startups find product market fit, accelerate their growth, and develop company culture. His hobbies include mountain biking, reading business books, testing new apps, anything design related and gardening. He welcomed his first son into the world in May.
- Total investments:
- 29
- Last investment:
- Lead investor:
- 76%
Last updated:
For AI agents: llms.txt
Industries Natty Zola invests in
Stages Natty Zola invests in
Countries Natty Zola invests in
Investment Focus
Industry
- Software 6 (21%)
- Artificial Intelligence 5 (17%)
- SaaS 4 (14%)
- Health Care 3 (10%)
- B2B 2 (7%)
Stage
- Pre-Seed 12 (41%)
- Seed 9 (31%)
- Series A 2 (7%)
Country
- United States 19 (66%)
- Peru 1 (3%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
Freeplay
|
Freeplay builds AI features that do real work. | Seed / Jun 03, 2025 | |
Maggie's
|
re-imagining the refuel & recharge experience | $2M / Pre-Seed / Apr 23, 2025 | |
|
Freeplay
|
Freeplay builds AI features that do real work. | $5.6M / Seed / Sep 30, 2024 | |
|
Freeplay
|
Freeplay builds AI features that do real work. | $3.3M / Pre-Seed / Nov 01, 2023 | |
Modern Adventure
|
Modern Adventure is an immersive travel brand and experience agency built for the 21st century. We transfuse the beating heart of a brand into extraordinary travel experiences.Modern Adventure's worldwide network of local partners, and decades of travel experience, mean we can deliver the experience of a lifetime for your customers, creatingrich content, unprecedented brand engagement, and lasting loyalty. | $4.8M / Series A / Aug 29, 2023 | |
Fulfilld
|
Fulfilld is an AI-powered location-aware (digital twin) warehouse management software focused on driving higher warehousing productivity more efficiently. Our AI is essential in orchestrating how products, people, and automation flow and work from the movement products arrive in the warehouse to when they are loaded onto delivery trucks. Our AI isthe brains and engine optimizing warehousing operations enabling our customers’ warehouses to run faster, smoother, leaner, and with fewer errors.Get Fulfilld. | $3.2M / Seed / Nov 10, 2022 | |
Stylo
|
Stylo is a vertical AI platform purpose-built for customer support teams. From agent assist to full ticket automation, Stylo unifies AI capabilities in a single experience embedded directly into platforms like Zendesk. Over 200 support teams trust Stylo to deliver faster responses, reduce costs, and scale quality—without sacrificing control.Founded by Josh Horowitz and Austin Emser in 2021, the company welcomed Eric Nelson as a co-founder in 2023 as it pivoted to focus on the customer support space. | $3M / Seed / Oct 19, 2022 | |
Bean
|
Freedom for Financial Accountants and flexibility for businesses starts here. We're a Tech-driven Accounting marketplace and project administration platform that's bringing together driven, ambitious and inspired independent Financial Accounting talent and matching them with incredible organizations. From startups and nonprofits tocompanies changing the world, we’re committed to delivering value they can feel. Our end to end engagement management platform provides margin for clients and professionals to prioritize what's most important to them - creating their future and experiencing their freedom. | $1.7M / Pre-Seed / Jul 30, 2022 | |
Showplace
|
Showplace is an in-home retail platform featuring products in top Airbnb homes enabling amazing brand experiences. | $2M / Seed / Jun 07, 2022 | |
Onward
|
Onward develops a digital freight marketplace that connects retailers who struggle to ship heavy goods with underutilized trucks already on the road. | $4.7M / Seed / Dec 08, 2021 | |
| See all 29 investments → | |||
Co-Investors
About Matchstick Ventures
Matchstick Ventures supports the creation and growth of early-stage technology companies in rapidly growing yet underserved startup ecosystems. The firm prefers to invest in seed-stage, early-stage, and later-stage companies. The firm seeks to invest in the business products, business services, information technology, and TMT sectors.
Matchstick Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
David M Nichols
LP / Striker
|
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David Secunda
StrikerStriker
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Natty Zola
Partner
|
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Nicki Miller
Operations Lead
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Ryan Broshar
Founder & Partner
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FAQ
What does Natty Zola invest in?
Natty Zola invests primarily in Software, Artificial Intelligence and SaaS startups, most often at Pre-Seed and Seed stage. Most of the 29 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
When did Natty Zola last invest?
The most recent investment recorded for Natty Zola closed in Jun 2025. Shizune tracks 29 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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