Finding the North Star: The Balance Between Strategy and Returns

Jul 23, 2025

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This week on Swimming with Allocators, Earnest and Alexa welcome Jon Wolkin, Managing Director of Deloitte Ventures. Jon shares his journey from investment banking to corporate venture, highlighting Deloitte's $150 million fund strategy that balances direct and fund investments across key technology verticals like AI, future of work, and health tech. The discussion reveals critical insights into corporate venture capital, emphasizing the importance of having a clear "North Star" strategy, understanding long-term value creation, and navigating the complex ecosystem of innovation. Key takeaways include the need for corporations to move quickly, provide strategic value beyond capital, and remain adaptable in a rapidly changing technological landscape. Jon also provides unique perspectives on the Canadian venture ecosystem, noting its potential in emerging technologies and the relatively low corporate venture participation compared to the US market. Don’t miss this in-depth discussion.

Highlights from this week’s conversation include:

Jon’s Career Journey (1:18)
Transition to Corporate Venture and Deloitte (3:19)
Strategic vs. Financial Objectives in CVC (4:39)
Long-term vs. Short-term Goals in Venture (7:15)
Challenges of Launching a Venture Arm in a Partnership (9:11)
Direct vs. Fund Investing Strategy (11:53)
Fund Selection and Ecosystem Engagement (13:20)
Alignment of Direct and Fund Investment Verticals (17:29)
Corporate VC Activity in Downturns (22:56)
Misconceptions About Corporate Venture Groups (25:21)
Advice for Emerging Managers Working with Corporates (27:59)
Key Learnings and Reflections at Deloitte Ventures (30:11)
Final Thoughts and Takeaways (32:20)

Deloitte Ventures Canada is a $150M corporate venture capital fund investing in Series A and B companies across fintech, cyber, climate, data/AI, and work tech. With a dual mandate of direct investments and fund investments, Deloitte Ventures is strategically positioned to support innovation while delivering financial and strategic value. Learn more at www.deloitte.ca.

Silicon Valley Bank (SVB), a division of First Citizens Bank, is the bank of the world’s most innovative companies and investors. SVB provides commercial and private banking to individuals and companies in the technology, life science and healthcare, private equity, venture capital and premium wine industries. SVB operates in centers of innovation throughout the United States, serving the unique needs of its dynamic clients with deep sector expertise, insights and connections. SVB’s parent company, First Citizens BancShares, Inc. (NASDAQ: FCNCA), is a top 20 U.S. financial institution with more than $200 billion in assets. First Citizens Bank, Member FDIC. Learn more at svb.com.

Swimming with Allocators is a podcast that dives into the intriguing world of Venture Capital from an LP (Limited Partner) perspective. Hosts Alexa Binns and Earnest Sweat are seasoned professionals who have donned various hats in the VC ecosystem. Each episode, we explore where the future opportunities lie in the VC landscape with insights from top LPs on their investment strategies and industry experts shedding light on emerging trends and technologies.

The information provided on this podcast does not, and is not intended to, constitute legal advice; instead, all information, content, and materials available on this podcast are for general informational purposes only.