Driving Alpha

What if the best way to win a deal isn't a faster term sheet, but a five-year head start on the relationship? That's the premise behind how Kyle Harrison and Contrary source and back founders.

Here's a glimpse of what you'll learn:

• 00:00 Welcome and Guest Intro

• 01:14 Contrary People Network

• 04:27 Research and Writing Flywheel

• 08:28 AI Tools and Thinking

• 11:58 Big Funds and Capital Cycles

• 20:01 Inside The Anduril Thesis

• 24:25 LPs and Defense Investing

• 27:49 Defense Bubble Psychology

• 33:52 Markets Kyle Excited About

• 38:14 Closing Thanks

Kyle, General Partner at Contrary, breaks down the firm's people-centric sourcing model, building relationships with future founders years before they raise capital, and how that approach put Contrary inside Ramp, Anduril, Basepower, and Hallow well before those bets were obvious. He also lays out his framework for today's fundraising environment: the "unholy trinity" of yield-seeking LPs, capital agglomerators, and capital-absorbing startups.

Kyle and Sam also get into the three-year research project behind his book, The Anduril Thesis, what a century of military-industrial history teaches about underwriting founders like Palmer Luckey, and how he uses Claude and Claude Code without letting AI replace his own thinking. They close on where Contrary is investing today, from software moats like Carta Health to physical-world bets like American Housing Corporation.

Episode Host: Alpha Partners

This episode is brought to you by Alpha Partners, an NYC-based growth equity firm managing $300 million. Alpha co-invests in top-tier growth equity companies led by the world's best investors. We focus on scaling and late-stage tech investment opportunities primarily in the essential technology sector, including e-commerce, enterprise software, fintech, edtech, and health IT. To learn how we can help you with your funding goals, visit https://www.alphapartners.com, or email us at [email protected].

What does it take to identify a multi-decade investment category before the rest of venture capital even considers it viable? Julian Counihan launched Schematic Ventures in 2017 to back Physical AI and supply chain technology when the space was widely considered uninvestable — and spent the years since building factory-floor relationships and writing first checks in companies like Altana, Flock Freight, Harbinger, and Platform Science.

Here's a glimpse of what you'll learn:

00:00 Welcome and Introductions

00:41 Origin of Schematic Thesis

02:03 Moving to San Francisco

03:40 First Checks in Supply Chain

05:13 Vibe Coding and AI Agents

09:58 Fund Three Edge in Physical AI

13:36 Hardware Software Investment Mix

14:31 Tourists and New Capital

16:24 Capex and Financing Reality

18:50 Valuations and Cycle Discipline

20:41 Humanoid Robots Reality Check

22:47 SpaceX and Liquidity Thoughts

24:18 Next Magic Moments in AI

27:47 Model Costs and Subsidies

28:59 Closing Thanks and Wrap

Brian and Julian trace the early conviction behind fund one — from Altana's supply chain data disruption to Harbinger's Class 6 electric truck. They discuss what separates fundable capital-intensive businesses from those that aren't, how Julian counsels founders through peak-cycle valuations, and the edge that two decades of factory visits and industry relationships buys you when generalist investors flood your category.

The episode also covers Julian's daily use of AI coding agents, why the magic comes from the harness around the model rather than the model itself, and a grounded take on where humanoid robotics actually stands today.

Episode Host: Alpha PartnersThis episode is brought to you by Alpha Partners, an NYC-based growth equity firm managing $300 million. Alpha co-invests in top-tier growth equity companies led by the world's best investors. We focus on scaling and late-stage tech investment opportunities primarily in the essential technology sector, including e-commerce, enterprise software, fintech, edtech, and health IT. To learn how we can help you with your funding goals, visit https://www.alphapartners.com, or email us at [email protected].

What does it take to generate consistent growth equity returns in one of the most regulated industries in the world? Ben Cukier, Partner and Co-Founder of Centana Growth Partners, has spent over 25 years doing exactly that, investing exclusively in the financial services ecosystem and backing the companies that are quietly transforming it.

Here's a glimpse of what you'll learn:

• 00:00 Welcome and Ben Intro

• 01:41 Regulation Over AI

• 02:24 Moats and Compliance

• 04:44 KYC and Sanctions Example

• 05:39 Portfolio Spotlight: Sayari Labs

• 06:20 ZestyAI InsurTech Pivot

• 07:40 Wildfire Model and 50-State Filings

• 10:07 Israel and the Fintech Ecosystem

• 10:56 Founder Pitch and Unit Economics

• 12:57 Growth Stage and Fund III

• 14:48 How Centana Makes Decisions

• 18:09 Career Lessons and Trusting People

• 21:05 Biggest Miss: Passing on PayPal

• 22:21 Fintech Market Size and the 2021 Vintage

• 23:35 Five-Year Outlook and AI Adoption

• 27:39 Closing and Next Steps

Steve Brotman speaks with Ben Cukier about why regulation in financial services is not a headwind but a durable competitive moat. Ben walks through how every company Centana backs must be regulation-aware, citing KYC, sanctions compliance, and beneficial ownership identification as examples of where fintech creates real enterprise value. He dives into portfolio companies Sayari Labs and ZestyAI, and explains how the latter pivoted from solar lead generation into one of the most sophisticated AI-powered property underwriting platforms in the insurance industry.

Ben also shares how Centana evaluates unit economics and what growth-stage really means to them, the firm's inclusive investment committee process, and why he believes the big banks and insurers will remain dominant while their service providers undergo radical transformation. He reflects on passing on PayPal, the 2021 valuation bubble, and why he still believes the SaaS apocalypse narrative is both real and overblown at the same time.

What does it take to consistently generate venture capital returns in one of the most complex industries in the world? Garheng Kong, founder and managing partner of HealthQuest Capital, has spent more than two decades answering that question, backing transformative healthcare companies that improve patient outcomes while bending the healthcare cost curve. A physician, scientist, and engineer by training, Garheng has led investments resulting in more than 40 IPO and M&A exits across medical devices, diagnostics, biopharma, and healthcare services.

Here's a glimpse of what you'll learn:

• 00:10 Meet Garheng Kong

• 01:51 Athletics and Teamwork

• 03:08 From Medicine to Investing

• 05:29 Why Start HealthQuest

• 08:17 Modality Agnostic Edge

• 09:42 Measuring Outcomes and Value

• 12:35 Evaluating Founders Fast

• 15:35 Hidden Systemic Problems

• 17:55 AI in Healthcare

• 25:40 Lessons and Mentorship

• 29:08 Succession and Alpha Edge

• 32:07 Lightning Round and Wrap

In this episode,

Garheng shares the investment philosophy behind HealthQuest Capital and explains why the firm takes a modality-agnostic approach to healthcare investing. Instead of focusing on a single sector like software or medical devices, HealthQuest evaluates opportunities across the entire healthcare ecosystem, searching for companies that deliver measurable improvements in both patient outcomes and healthcare economics. Garheng also discusses how today's payer-driven healthcare environment has fundamentally changed innovation, requiring startups to prove both clinical value and financial impact from day one.

Additionally, Steve Brotman and Garheng dive into the structural inefficiencies that create massive opportunities for healthcare innovation, from administrative bloat to the disconnect between patients, providers, and payers. They explore how venture investors evaluate founders in the first minutes of a meeting, why resilience and domain expertise matter more than perfect business plans, and how AI is beginning to transform healthcare by saving both time and lives. Garheng also shares his perspective on the technologies shaping the next decade of healthcare, from robotic surgery and AI diagnostics to why gene editing may be overhyped today while genetic sequencing is quietly becoming one of the most powerful tools in modern medicine.

A cancer diagnosis rarely leads to a venture fund, but for Ben Freeberg, it became the catalyst for building one. As Founder and Managing Partner of Oncology Ventures, Ben transformed a firsthand experience with broken cancer care into a focused investment strategy aimed at fixing the system from the inside out.

Here's a glimpse of what you'll learn:

• 00:12 Introduction and Welcome

• 01:17 The Origin Story of Oncology Ventures

• 04:56 Challenges and Surprises in Fundraising

• 07:07 Superpowers of Oncology Ventures

• 10:02 Fund Performance and Future Plans

• 17:28 Impact on Patient Lives

• 21:39 The Role of Stand-Up Comedy in Venture Capital

• 24:38 Life in Austin and Closing Remarks

In this episode,

Host Brian Smiga speaks with Ben Freeberg about the moment his professional trajectory changed forever. After surviving cancer, and navigating delayed diagnoses, fragmented care, and costly inefficiencies, Ben recognized that the biggest opportunities in oncology weren't just in new drugs, but in the infrastructure, data, and care delivery systems surrounding them. That realization became the foundation for Oncology Ventures.

Also, Ben explains how a specialist venture model can outperform in complex healthcare markets. He breaks down why Oncology Ventures avoids drug development risk, how its strategic LP base of cancer centers and healthcare operators creates a powerful sourcing and commercialization advantage, and what it takes to underwrite early-stage oncology companies before the market fully validates them. The conversation also covers fund construction, co-investment discipline, and the real-world patient impact already generated, demonstrating how strong business models and meaningful outcomes can scale together.

What happens when a venture capitalist brings a deep understanding of government into the startup world? Yanev Suissa, Founder and Managing General Partner of SineWave Ventures, has done just that, carving out a powerful niche by helping commercial-first startups break into government markets. His journey from NEA to the Bush and Obama administrations gives him a perspective few investors can match.

Here's a glimpse of what you'll learn:

• 00:42 Introduction and Guest Overview

• 01:24 Yanev Suissa's Background and Career Path

• 02:19 The SineWave Ventures Model

• 03:33 Navigating the Government Tech Space

• 05:42 Competing with Mega Funds

• 07:50 Investment Decision-Making Process

• 10:24 Evaluating Founders and Teams

• 16:14 Impact of AI and Investment Landscape

• 18:23 The Importance of Vision in Entrepreneurship

• 19:16 AI and Business: Making Money and Saving Money

• 19:38 Challenges and Realities of AI Implementation

• 20:20 Future Proofing and Investment Strategies in AI

• 21:16 The Role of VCs in Supporting Startups

• 22:21 Debate: The Future Landscape of AI Companies

• 25:32 VCs and Founders: Building Productive Relationships

• 29:55 The Rewards and Challenges of Being a VC

• 31:42 Timeless Advice for Entrepreneurs and Investors

In this episode,

Yanev unpacks how his background in federal investment shaped the founding of SineWave Ventures, a VC firm built to help commercial technology companies win in both the public and private sectors. He explains why many venture-backed startups overlook government as a growth engine, and how SineWave uniquely helps founders access these massive, often hidden, revenue streams. With past investments in Databricks, SentinelOne, and Evolv, Yanev shares what makes a venture truly scalable across sectors.

The conversation dives deep into the challenges of competing with mega-funds, the critical role of team dynamics in startup success, and how Yanev's firm makes concentrated bets in a crowded market. He also offers a candid perspective on the current AI supercycle; including what's hype, what's real, and how to think about sustainable ROI in enterprise AI adoption. Whether you're a founder, investor, or LP, Yanev's insights offer a playbook for navigating venture capital with both conviction and clarity.

Sponsor Host: Affinity

Affinity is a relationship intelligence platform that empowers dealmakers in relationship-driven industries to find, manage, and close more deals. With the most automated relationship intelligence insights and technology, Affinity enables leaders to drive deals and ensure their teams can take action with confidence, knowing the context and history of every relationship.

The Affinity platform, including Affinity CRM, is used by over 3,000 relationship-driven organizations worldwide. Founded in 2014, Affinity is headquartered in San Francisco and backed by leading investors, including Menlo Ventures, Advance Venture Partners, 8VC, and MassMutual Ventures.

Learn more at https://affinity.co

What if your venture capital firm could plug you directly into the world's most influential corporations; unlocking growth, customers, and global scale overnight? That's exactly what Simon Wu does as a Partner at Cathay Innovation. Leading U.S. investments at the $2.5B global VC, Simon's work sits at the intersection of innovation, industrial strength, and strategic capital.

Here's a glimpse of what you'll learn:

• 00:41 Introduction to Alpha Partners and Guest Simon Wu

• 01:33 The Origin Story of Cafe Innovation

• 03:06 Growth and Expansion of Cafe Innovation

• 05:59 Unique Corporate Connections and Investment Strategy

• 11:04 Navigating the Competitive Venture Capital Landscape

• 15:23 AI and Wealth Tech: Current Trends and Future Predictions

• 23:28 Closing Thoughts and Future Collaborations

In this episode,

Simon Wu shares how Cathay Innovation bridges the gap between fast-moving startups and industry giants, turning traditional corporate LPs into game-changing partners for growth-stage companies. From automotive and energy to digital health and fintech, Simon explains how their global corporate network unlocks distribution, contracts, and strategic edge for portfolio founders. With nearly 20 core corporate LPs and hundreds of partners worldwide, Cathay's model delivers far more than capital.

Simon also reveals what separates the good from the great in today's AI-fueled startup landscape. He walks through Cathay's investment in companies like Skan and Range, outlines how their ecosystem teams help navigate enterprise sales, and breaks down what it really takes to win Series A and B rounds in a bifurcating VC market. For VCs, founders, and operators alike, this conversation is a masterclass in strategic venture capital at scale.

Sponsor Host: Affinity

Affinity is a relationship intelligence platform that empowers dealmakers in relationship-driven industries to find, manage, and close more deals. With the most automated relationship intelligence insights and technology, Affinity enables leaders to drive deals and ensure their teams can take action with confidence, knowing the context and history of every relationship.

The Affinity platform, including Affinity CRM, is used by over 3,000 relationship-driven organizations worldwide. Founded in 2014, Affinity is headquartered in San Francisco and backed by leading investors, including Menlo Ventures, Advance Venture Partners, 8VC, and MassMutual Ventures.

Learn more at https://affinity.co

In venture capital, power isn't just about capital, it's about who gets to decide where it flows.

Paige Hendrix Buckner, CEO of All Raise, is redefining who sits at the decision-making table. With a background spanning public policy, education, and founder support, she's leading a movement to shift both the culture and the calculus of VC, proving that diverse check-writers create better outcomes.

Here's a glimpse of what you'll learn:

• 00:42 Welcome to the Driving Alpha Podcast

• 00:52 Meet Paige Hendrix Buckner: CEO of All Raise

• 01:38 Paige's Journey: From Education to Entrepreneurship

• 04:34 All Raise's Mission and Impact

• 06:09 Transformations in Venture Capital

• 09:12 Empowering Women and Non-Binary Investors

• 13:10 Building Competitive Advantage

• 21:41 The Importance of Sponsorship and Mentorship

• 29:43 All Raise's Networking and Community Initiatives

• 33:34 The Power of Storytelling in Venture Capital

• 38:15 The Business Case for Diversity

• 41:37 Final Thoughts and Call to Action

In this episode,

Paige joins Driving Alpha host Zoe van den Bol to explore how shifting power toward women and non-binary investors can unlock smarter investing and stronger returns. Backed by compelling data, Paige shares how All Raise has doubled the number of women in Partner+ roles and is now laser-focused on helping them build measurable influence, from leading deals to securing board seats.

They dive into tactical strategies for junior investors looking to grow their credibility and capital access, the importance of mentorship and sponsorship in a relationship-driven industry, and how to build a personal brand that earns deal flow. Paige also speaks candidly about the need to normalize being "transactional", and how that mindset shift helps communities, and careers, thrive.

This is a masterclass in rethinking power, performance, and the future of venture capital.

What if your investor could also be your first customer, biggest champion, and gateway into a massive market? David Horowitz, Partner at Cerity Partners Ventures and a corporate VC pioneer, has spent over 20 years proving that venture capital can do more than write checks, it can open doors.

Here's a glimpse of what you'll learn:

• 00:43 Introduction and guest welcome

• 01:21 David Horowitz's early career and venture capital journey

• 04:49 founding Touchdown Ventures

• 06:38 The evolution and success of Touchdown Ventures

• 08:16 Cerity Partners merger and wealth management

• 13:16 Corporate venture capital insights

• 25:28 Future of corporate venture and AI

• 30:19 Closing remarks and future plans

In this episode,

David takes us behind the scenes of his remarkable career, from launching Comcast Ventures to building Touchdown Ventures into the gold standard of corporate VC. Now leading Cerity Partners Ventures, David reveals how his team manages over 20 corporate venture funds, helping Fortune 500s invest in and support startups with precision and purpose.

You'll learn why corporate VC isn't just capital, it's a strategic lever for growth. David explains how his model brings startups deep industry access, faster validation, and critical early feedback that de-risks innovation. He also shares how vertical AI is becoming a central theme across sectors like legal tech, healthcare, manufacturing, and insurance, and how Cerity is helping founders unlock these opportunities globally.

Can AI truly transform the enterprise, not just improve it?

Eric Benhamou, legendary tech CEO and founder of Benhamou Global Ventures, believes it already is. He reveals how his firm is leading the charge with "Enterprise 5.0", a new era defined by full-stack, AI-native solutions.

Here's a glimpse of what you'll learn:

• 00:43 Intro to Alpha Partners

• 01:00 Meet Eric enhamou: A Pioneer in Tech

• 02:09 Understanding Enterprise 5.0

• 04:26 Case Study: Events and AI Accessibility

• 07:37 Selling to Enterprises: Insights from a Fortune 500 CEO

• 09:42 The Global Edge: Investing Beyond Silicon Valley

• 15:44 Spotlight on Paris and Japan

• 20:32 Building a Network of Advisors

• 25:45 Conclusion and Final Thoughts

In this episode,

Eric Benhamou joins host Brian Smiga for a powerful conversation on what it means to build and invest in AI-driven companies that go beyond hype to deliver tangible results. Eric introduces the concept of "Enterprise 5.0," where AI is not just an enhancement but the core ingredient of transformative enterprise platforms. He shares the story of Evinced, an accessibility startup solving compliance at scale using AI, not just to detect issues, but to fix them automatically.

Eric also reveals why some of the world's most resilient and high-performing startups are being built far from Silicon Valley. With deep roots in Israel, France, India, and soon Japan, BGV's global model taps into the best AI talent worldwide, often at a fraction of the cost. He discusses how grit, ambition, and cross-border structuring create companies with global potential from day one.

The conversation rounds out with Eric's insights from the frontlines of enterprise sales, where his CEO playbook helps founders sell strategically, not just tactically. He also shares BGV's secret weapon: an elite advisory network of CTOs, CISOs, and AI experts who shape product strategy and accelerate go-to-market. If you want a front-row seat to how AI is truly redefining enterprise, this episode is a must-listen.