
E136: Navigating Startup and Venture Capital Legal Risks w/Constantine Karides
02/07/25 • 22 min
Highlights: Choosing a Lawyer as a Strategic Partner: Beyond paperwork, founders should seek legal advisors who bring investor connections, industry expertise, and pricing flexibility.
The Importance of Internal Influence: How a lawyer’s standing within a firm impacts their ability to secure favorable terms and resources for clients.
VCs & Legal Counsel: What venture capital funds should prioritize when selecting legal partners and how these relationships can create long-term value.
Law Firm Profit Models: Understanding the leverage model law firms use to maximize profits and how clients can navigate these dynamics.
AI & The Future of Law: How artificial intelligence is transforming the legal industry, from document review to litigation strategy.
Building Long-Term Client Relationships: Constantine’s philosophy on blending business with personal relationships to drive success.
Lessons from Experience: Mistakes Constantine made early in his career and how they shaped his approach to law and business.
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Guest Bio: Constantine Karides is a Lead Partner at Reed Smith, a global law firm known for its expertise in venture capital, private equity, and corporate transactions. With over 30 years of experience, Constantine has built a reputation as a trusted advisor to startups, funds, and investors, offering not just legal counsel but also strategic business insights. Recognized as a "rainmaker" at Reed Smith, he emphasizes client relationships, networking, and long-term value creation.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
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SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.
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Stay Connected: Twitter: David Weisburd: @dweisburd
LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/
Constantine Karides: https://www.linkedin.com/in/constantine-karides/
Links Reed Smith: www.reedsmith.com
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview (2:08) Law firms' internal credibility and Venture Capital specific needs (5:29) Evaluating Startups and the leverage model in law firms (9:57) Trust-building and client relationship philosophy (14:41) Early career lessons and the impact of AI on the legal field (19:00) Client views on AI adoption in law firms (21:03) Closing remarksHighlights: Choosing a Lawyer as a Strategic Partner: Beyond paperwork, founders should seek legal advisors who bring investor connections, industry expertise, and pricing flexibility.
The Importance of Internal Influence: How a lawyer’s standing within a firm impacts their ability to secure favorable terms and resources for clients.
VCs & Legal Counsel: What venture capital funds should prioritize when selecting legal partners and how these relationships can create long-term value.
Law Firm Profit Models: Understanding the leverage model law firms use to maximize profits and how clients can navigate these dynamics.
AI & The Future of Law: How artificial intelligence is transforming the legal industry, from document review to litigation strategy.
Building Long-Term Client Relationships: Constantine’s philosophy on blending business with personal relationships to drive success.
Lessons from Experience: Mistakes Constantine made early in his career and how they shaped his approach to law and business.
--
Guest Bio: Constantine Karides is a Lead Partner at Reed Smith, a global law firm known for its expertise in venture capital, private equity, and corporate transactions. With over 30 years of experience, Constantine has built a reputation as a trusted advisor to startups, funds, and investors, offering not just legal counsel but also strategic business insights. Recognized as a "rainmaker" at Reed Smith, he emphasizes client relationships, networking, and long-term value creation.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
--
SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.
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Stay Connected: Twitter: David Weisburd: @dweisburd
LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/
Constantine Karides: https://www.linkedin.com/in/constantine-karides/
Links Reed Smith: www.reedsmith.com
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview (2:08) Law firms' internal credibility and Venture Capital specific needs (5:29) Evaluating Startups and the leverage model in law firms (9:57) Trust-building and client relationship philosophy (14:41) Early career lessons and the impact of AI on the legal field (19:00) Client views on AI adoption in law firms (21:03) Closing remarksPrevious Episode

EP135: How to Access Top Quartile Venture Capital Funds w/Mel Williams
In this episode of How I Invest, I have a conversation with Mel Williams, Co-Founder and General Partner at TrueBridge Capital Partners. We dive into TrueBridge’s pivotal role as Forbes' data partner for the prestigious Midas List, its strategic approach to venture capital fund-of-funds investing, and how the firm consistently identifies and backs the top-performing fund managers. Mel provides a masterclass on portfolio construction, risk management, and scaling a successful venture investment platform. Whether you’re an institutional investor, a fund manager, or simply intrigued by the inner workings of venture capital, this episode is packed with essential takeaways.
Highlights: The Midas List Partnership: How TrueBridge collaborates with Forbes to curate the definitive VC ranking and what it means for the industry.
Fund of Funds Strategy: The five key investment strategies that shape TrueBridge’s unique venture approach—core venture, seed, direct, secondary, and blockchain investments.
The Power of Forced Ranking: A disciplined framework for ranking fund managers and how it enhances returns.
Gaining a Competitive Edge: How TrueBridge’s relationships with elite GPs provide them unparalleled access and insight.
Navigating Blockchain Volatility: TrueBridge’s philosophy on investing in blockchain and adjusting for its extreme market cycles.
Scaling Venture Funds Effectively: Best practices for fund managers to grow while maintaining their competitive advantage.
International vs. Domestic Venture Investing: How TrueBridge evaluates and ranks global venture funds against U.S.-based managers.
Lessons from Building TrueBridge: The realities of raising early funds and scaling a top-tier fund-of-funds platform.
Debunking the Fund-of-Funds Fee Myth: How TrueBridge offsets the double-fee structure through strategic overcommitment and capital recycling.
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Guest Bio: Mel Williams is the Co-Founder and General Partner at TrueBridge Capital Partners, a premier venture capital fund-of-funds specializing in backing top-tier venture firms and startups. With a background in institutional investing at the University of North Carolina Endowment and the Rockefeller Foundation, Mel brings unparalleled expertise in fund selection, portfolio construction, and venture capital strategy. Under his leadership, TrueBridge has cultivated one of the most coveted LP portfolios in the industry, leveraging deep networks and a research-driven investment approach.
Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
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Stay Connected: Twitter: David Weisburd: @dweisburd
LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mel Williams: https://www.linkedin.com/in/mel-williams-00584a5/
Links TrueBridge Capital Partners: https://www.truebridgecapital.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview (4:38) Investing in blockchain and managing volatility in venture funds (5:51) Building relationships and the forced ranking system in portfolio management (10:21) Criteria for adding or removing venture fund managers (14:43) Best practices for scaling and international venture investments (20:23) Challenges in raising funds and the venture industry evolution (2012-2021) (24:17) Comparing fund of funds to direct venture capital investments (26:51) Efficiency and key aspects of TruBridge's fund of funds model (29:05) Closing remarksNext Episode

E137: Lessons from Managing $300 Billion Dollars w/ John Skjervem (CIO of URS)
In this episode of How I Invest, I dive deep into a discussion with John Skjervem, Chief Investment Officer at Utah Retirement Systems (URS), to uncover the unique governance and investment strategies behind one of the most innovative public pension funds in the United States. John shares his insights on governance structures, private equity allocations, the benefits of a "fishbowl-free" decision-making process, and his approach to alternative energy investments. Whether you're curious about pension fund management or the future of disruptive energy investments like nuclear fusion, this episode is a masterclass in strategic thinking and long-term investing.
Highlights: Governance Matters: Why URS’s closed-door investment meetings create better outcomes compared to traditional public pension governance.
Transparency vs. Returns: How excessive transparency can lead to political grandstanding and ultimately harm long-term investment performance.
Asset Allocation Strategy: A deep dive into URS’s allocation, including a 14% allocation to private equity with significant exposure to venture capital.
Direct Real Estate Investments: How URS has built a successful real estate portfolio, reducing fees and maintaining long-term control over assets.
Energy and Infrastructure Investments: The role of direct investments in oil, gas, and alternative energy as an inflation hedge.
The Case for Venture Capital: Why URS prioritizes venture capital investments over private credit to maximize returns.
Betting on Nuclear Fusion: The potential for a 100x return on URS’s investments in fusion energy and the long-term implications for the energy sector.
Size vs. Agility: Why smaller funds like URS have an advantage in private markets despite their scale limitations.
Lessons from the Global Financial Crisis: How John’s approach to risk management and asset allocation was shaped by 2008.
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Guest Bio: John Skjervem serves as the Chief Investment Officer at Utah Retirement Systems, where he oversees over $50 billion in assets. With prior experience managing larger funds like the Oregon Public Employees Retirement Fund and Northern Trust's wealth business, John brings a wealth of expertise to his current role. Known for his innovative governance approach and deep knowledge of alternative investments, John is passionate about achieving long-term success for URS beneficiaries.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
We’d like to thank @JuniperSquare @ReedSmith for sponsoring this episode!
#VentureCapital #VC #Startups #OpenLP #AssetManagement
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SPONSOR: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.
SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.
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Stay Connected: Twitter: David Weisburd: https://x.com/DWeisburd
LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Skjervem: https://www.linkedin.com/in/john-d-skjervem-cfa-4698794/
Links
Utah Retirement Systems: https://www.urs.org/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Episode preview (1:00) Asset allocation and governance at Utah Retirement Systems (4:07) Governance structure at Utah Retirement Systems (9:25) Long-term investment challenges (10:57) Sponsor: Juniper Square (11:30) Private equity and real estate in asset allocation (15:44) Managing a $50 billion fund (16:25) Sponsor: Reed Smith (17:30) Investment check sizes and advisory roles (20:31) Comparing Utah Retirement Systems with Alaska Permanent Fund (22:11) Lesso...If you like this episode you’ll love
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