In a landscape where traditional venture capital is under scrutiny, Oliver Libby is proving that there’s a better way forward. As the Co-Founding Managing Partner of H/L Ventures and City Rock Venture Partners, and Chair of the Resolution Project, Libby is building a new kind of VC model—one that marries deep operational involvement with a relentless commitment to impact.
In our latest Ignite Podcast episode, we dive into Oliver’s unique journey from military history and national security to leading one of the most innovative, mission-aligned firms in the venture world. Whether or not you tune into the episode, here’s what you need to know about his model, his vision, and the future he’s working to build.
From National Security to Venture Capital
Oliver didn’t take a typical path into VC. After studying military history and working in national security post-9/11, he pivoted into consulting, where he first encountered the startup world. That experience eventually led to the founding of H/L Ventures—launched at the height of the global financial crisis—and the Resolution Project, a nonprofit that empowers young social entrepreneurs globally.
His North Star from the beginning? Values. “Whatever you go into, you better be helping people,” he recalls from family dinner-table lessons.
The Daily Active Engagement Model
What makes H/L Ventures different? Libby calls it “daily active engagement.” Unlike most VC firms that drop in a few times a quarter, H/L puts a full platform team—nearly 80 people—at the disposal of every startup they back.
They help with everything from talent and marketing to governance and crisis management. This isn't just passive capital—it’s embedded partnership. “We’re not just picking great ingredients,” Libby says. “We’re cooking the meal, too.”
Studio Meets Fund: A Hybrid Approach
Through HL Studio and City Rock Venture Partners, the firm engages startups at every stage:
HL Studio supports pre-Series A startups with operational help and equity-based alignment.
City Rock writes traditional checks ($500K–$1.5M) at Series A and beyond, while still delivering deep engagement.
They also operate with a blend of common and preferred stock, an unusual structure that gives them flexibility and aligns incentives for founders.
Investing at the Intersection of Purpose and Profit
H/L Ventures doesn’t believe in a tradeoff between mission and returns. Libby argues that the best opportunities lie in the overlap of growth, values, and impact. The firm’s portfolio spans:
Clean energy and sustainability
Cybersecurity and law enforcement tech
Creator economy infrastructure
Diverse founding teams and underrepresented markets
“We don’t invest to make political statements. We invest to help people and generate strong returns.”
The Resolution Project: $3K Grants to Unicorns
The Resolution Project, a nonprofit Libby co-founded, has backed nearly 1,000 social ventures with micro-grants. Some of these have scaled to valuations over $1B (like Esusu), proving the massive leverage small early investments in young, purpose-driven leaders can have.
And here’s the kicker: Resolution doesn’t take equity. “We’re just there to help,” Libby explains. “We’re the mentor they call at 3 AM.”
On AI, Economic Disruption, and the American Dream
Libby doesn’t shy away from hard questions. What happens when AI displaces millions of jobs? How do we redistribute the gains of technological progress fairly? What does a fulfilling life look like in a post-work world?
“We need policies, private capital, and technology to work together. Venture capital has a civic responsibility too,” he says.
He’s also deeply concerned about the fading belief in the American Dream. His response? Build a society with a strong floor and no ceiling—where everyone has basic security, but unlimited opportunity.
Leadership, Longevity, and What Comes Next
Libby’s perspective on leadership is grounded in resilience. “Most people confuse check with checkmate,” he says. “You need to know the difference—and lead others through it.”
Looking ahead, he believes the future of VC will be more hands-on, more collaborative, and far less generic. He envisions ecosystems of firms that specialize, partner, and support founders more holistically.
Final Takeaway
Oliver Libby is not just questioning the old rules of venture capital—he’s actively rewriting them. His model proves that you can be both profitable and principled, operational and mission-driven. Whether you’re a founder, investor, or just someone curious about where business is headed, his approach offers a blueprint for aligning values with velocity.
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Chapters:
00:01 – From Military History to Mission-Driven VC
02:45 – Family Values and a Lifelong Commitment to Impact
05:00 – The H/L Ventures Model: Daily Engagement, Real Value
09:30 – Why Traditional VC Is Broken
14:00 – Profit Meets Purpose: The New Investment Thesis
17:00 – “Controversial” Impact Bets: Defense, Cybersecurity, Law Enforcement
19:10 – AI, Automation, and the Future of Jobs
21:50 – The Rise of the Creator Economy & Entrepreneurial Resilience
26:25 – Sci-Fi, Star Trek, and the Ethics of Abundance
31:57 – Rebuilding the American Dream: Floor and No Ceiling
39:00 – Should VCs Solve Global Problems?
44:00 – Sustainability Through Innovation, Not Austerity
46:42 – Reinventing VC: Specialization, Collaboration, and Platforms
48:30 – The Resolution Project: 1,000 Ventures, $3K at a Time
54:00 – Billion-Dollar Outcomes from Micro Grants
56:13 – Leadership Lessons from the Frontlines of Impact
59:35 – Why Networking Is the Last Unautomated Skill
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