Building deliberately. Acting decisively. A holding company where ideas compound.
What We Do
Bolewood Group is a holding company and AI-native innovation lab.
We build, ship, and operate independent software products from idea to operation.
We incubate ideas patiently, but we move fast when the moment is right.
We use AI as a force multiplier to prototype faster and learn sooner across everything we build.
We do advisory and board work only where our experience and judgment materially change outcomes.
We are not a fund.
We are not an agency.
We don’t chase growth for its own sake.
We care about ownership, durability, and doing real work that holds up over time.
How We Think
We care deeply about what happens after something ships.
AI has compressed the technical barriers to entry, making taste and judgment the final frontiers of value. We optimize for those.
Time is the primary ingredient in anything worthwhile, including products, relationships, trust, and learning.
We would rather create value than extract it. When value spreads outward to users, partners, teams, and communities, durability follows.
We believe patience is a competitive advantage and that most meaningful things are grown deliberately, but acted on decisively.
Anthony Showalter | Founder
Bolewood Group was founded by Anthony Showalter, a software entrepreneur with two decades of experience building, scaling, and exiting technology companies.
Anthony has founded multiple venture-backed software businesses, most notably as co-founder of Pear Deck, where he led the company from its first prototype in 2014 to serving over 20 million students through its acquisition by GoGuardian in 2020. His work spans the full lifecycle of software companies—from product conception and engineering scale-up to go-to-market and the complex, often overlooked work of post-exit stewardship.
Today, Anthony focuses on building and operating a selective portfolio of AI-native software products under the Bolewood Group umbrella. He collaborates with a network of domain experts across product, security, and infrastructure to design software that blends human judgment with AI systems.
In parallel, Anthony provides selective advisory and board leadership to founders where long-term pattern recognition and strategic access materially change outcomes. He frequently invests alongside operators he knows well, prioritizing businesses where he can contribute unique insights.
Portfolio
Bolewood Group operates a small portfolio of independently branded products. Each product has its own mission, roadmap, and user base.
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Advisory
Bolewood Group engages in select advisory and board work where our operating experience is directly relevant. This work is intentionally selective and capacity-constrained.
Contact
For general inquiries, privacy questions, or existential musings.