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Venture Guides is an early-stage venture capital firm founded in 2023 and based in Boston, Massachusetts. The firm focuses on investing in and actively guiding companies in the infrastructure software sector, including cloud, security, AI, and data companies. With a fund size of $263 million, Venture Guides is positioned to support a concentrated portfolio of 15-20 companies, allowing for focused operational assistance and strategic guidance.
The firm has quickly established itself in the venture capital landscape, leveraging a team of approximately 20 experienced professionals, many of whom are former operators in various sectors. This operator-led approach enables Venture Guides to provide hands-on support to its portfolio companies, enhancing their chances of success in competitive markets. The firm has also created a collaborative environment by co-locating portfolio companies in its Boston headquarters, fostering knowledge sharing and growth.
Venture Guides invests primarily in early-stage companies, particularly in the infrastructure software sector. The firm targets sectors such as AI, SaaS, fintech, cybersecurity, healthcare, biotech, consumer, commerce, logistics, and energy. Their investment strategy is characterized by a team-based approach that emphasizes collaboration and operational expertise. The firm typically invests at the Pre-seed, Seed, Seed+ (Extension), and Series A stages, with check sizes ranging from $500,000 to $5 million.
Venture Guides maintains a concentrated portfolio of 15-20 companies, allowing for focused support and guidance. The firm actively seeks founders who demonstrate a strong vision and a commitment to building innovative solutions in their respective fields. Their investment thesis centers on providing hands-on operational support, leveraging their expertise to drive growth and success for portfolio companies.
Venture Guides' portfolio includes a diverse range of companies specializing in infrastructure software and related sectors. Notable companies in their portfolio include:
Venture Guides has invested in 17 companies to date, showcasing a commitment to supporting innovative startups in the infrastructure software space.
Ben Nye: Managing Partner. Former Co-Managing Partner at Bain Capital Ventures, Ben is a central figure behind Venture Guides, bringing extensive experience in venture capital and operational leadership.
Anton Simunovic: Partner. Anton has a background in technology investments and operational roles, contributing to the firm's strategic direction.
Ava Simunovic: Partner. Ava specializes in early-stage investments and has a strong track record in supporting startups through their growth phases.
Bear Brofft: Partner. Bear brings expertise in cybersecurity and infrastructure software, enhancing the firm's focus in these sectors.
Ben Holzman: Partner. Ben has a background in finance and technology, providing valuable insights into investment opportunities.
Chuby Uche: Partner. Chuby focuses on operational support and strategic guidance for portfolio companies.
Daniel Bronsoiler: Partner. Daniel has experience in scaling startups and offers mentorship to founders.
Ian Penny: Partner. Ian specializes in data-driven investment strategies and operational excellence.
Jenny Pyle: Partner. Jenny has a strong background in product development and market strategy.
Josh Valentine: Partner. Josh focuses on business development and growth strategies for portfolio companies.
Mike Shanahan: Partner. Mike brings expertise in financial management and operational efficiency.
Mo Garad: Partner. Mo specializes in technology investments and startup growth.
Newt Davis: Partner. Newt has a background in venture capital and operational leadership.
Nico Herden: Partner. Nico focuses on market analysis and investment strategy.
Nishkam Prabodh: Partner. Nishkam has experience in scaling technology companies and offers mentorship to founders.
Raz Casarjian: Partner. Raz specializes in cybersecurity and infrastructure software investments.
Roslyn McLean: Partner. Roslyn focuses on operational support and strategic guidance for portfolio companies.
Sage Nye: Partner. Sage has a background in finance and technology, contributing to the firm's investment strategy.
Steve Wood: Partner. Steve specializes in business development and growth strategies for startups.
Will Schnoor: Partner. Will has experience in venture capital and operational leadership, enhancing the firm's capabilities.
To pitch Venture Guides, founders should submit their proposals via email to leigh@ventureguides.com. A well-structured pitch deck should include information about the team, market opportunity, product details, and financial projections. The firm prefers concise and clear presentations that highlight the startup's unique value proposition.
Response times can vary, but founders can generally expect to hear back within a few weeks. Warm introductions are encouraged, as they can facilitate a more favorable review process.
Venture Guides operates the VG Sales Academy, a 6-week paid sales training program aimed at recent college graduates. This program focuses on developing essential sales skills and preparing participants for roles in tech startups. The academy enhances the sales capabilities of portfolio companies by providing them with trained talent ready to contribute to their growth.
On April 22, 2026, Venture Guides announced the closing of Fund II at $262.5 million, oversubscribed within eight weeks. This fund represents a 21% increase from Fund I, which was $216.5 million. The firm has successfully re-engaged 100% of its Fund I family office investors while adding new institutional backers.
On October 30, 2025, Venture Guides made a notable investment in hoop.dev, participating in their Seed round alongside Y Combinator. Additionally, the firm led a $12 million Series A investment in Compyl, further solidifying its commitment to supporting innovative startups in the infrastructure software sector.
What are Venture Guides' investment criteria?
Venture Guides primarily invests in early-stage companies within the infrastructure software sector, including AI, cybersecurity, and cloud solutions. They focus on companies at the Pre-seed, Seed, Seed+, and Series A stages.
How can I pitch to Venture Guides?
Founders can pitch to Venture Guides by visiting their website at ventureguides.com and submitting their pitch via the provided email: leigh@ventureguides.com. A well-prepared deck should include details about the team, market opportunity, and product.
What makes Venture Guides different from other VC firms?
Venture Guides emphasizes a hands-on approach, providing operational support and strategic guidance to its portfolio companies. They also co-locate companies in their Boston headquarters to foster collaboration and knowledge sharing.
What is the typical check size for investments?
Venture Guides typically invests between $500,000 and $5 million in early-stage companies, depending on the stage and needs of the startup.
What is the firm's geographic focus?
Venture Guides primarily focuses on investments in North America, particularly in the United States.
What kind of support can portfolio companies expect?
Portfolio companies receive operational support, strategic guidance, and access to the VG Sales Academy, a training program designed to enhance sales skills and capabilities.
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