Overview of Masters in Business with Lawrence Calcano
Bloomberg’s Masters in Business features an in-depth conversation with Lawrence Calcano, CEO and chairman of iCapital, about how he helped build the firm into a leading technology platform for alternative investments. Calcano traces his career from Holy Cross and Dartmouth to Morgan Stanley and Goldman Sachs, then explains how iCapital became an “alternative investment marketplace” for advisors, wealth managers, and banks. The discussion covers the growing role of private markets, the operational complexity of alts, how AI and tokenization may reshape asset management, and why advisor-led distribution remains central.
Calcano’s Career Path: From Hockey Player to Wall Street Executive
Early influences and education
- Calcano says he didn’t have a clear career plan early on.
- His father’s unconventional upbringing taught him independence and self-reliance.
- He attended Holy Cross on a hockey recruitment and studied economics, with a theater minor.
First move into finance
- He chose Morgan Stanley over a potential acting career after weighing it against student loans and financial stability.
- At Morgan Stanley, he worked in mortgage finance, helping S&Ls raise capital and structure products like:
- Ginnie Mae securities
- Fannie Mae securities
- REMICs
- CMOs
Goldman Sachs and the tech boom
- After business school at Tuck, he joined Goldman Sachs.
- Over time, he moved into technology banking and eventually helped lead Goldman’s Global Technology Banking Group.
- He describes the late 1990s internet boom as a formative period that taught him how quickly markets and business models can change.
Lessons From the Dot-Com Era and Market Cycles
What the internet boom taught him
- Markets often struggle to value emerging technologies at first.
- Adoption can outpace expectations even when valuations later correct.
- His takeaway: technology waves are disruptive, and firms must adapt or risk being displaced.
Relevance to AI today
- Calcano sees parallels between the dot-com era and current AI adoption.
- He believes the hype often runs ahead of reality, but the underlying technology still matters enormously.
- His core message: companies should embrace new technology rather than hope it goes away.
Why He Built iCapital
The market gap he saw
- After leaving Goldman in 2007 and later observing the rise of independent RIAs, he saw a problem:
- Advisors leaving wirehouses lost access to the infrastructure needed to offer alternatives.
- Alternative investing was still highly manual, fragmented, and operationally cumbersome.
iCapital’s mission
- iCapital was built to provide an end-to-end platform for alternatives:
- product access
- education
- due diligence
- subscription workflow
- post-trade administration
- reporting and analytics
Expanded focus
- iCapital initially aimed to serve independent advisors, but Calcano says the firm realized even wirehouses lacked the technology needed to support alternatives effectively.
- The company now serves:
- wirehouses
- RIAs
- independent broker-dealers
- banks and asset managers
How iCapital Works for Advisors and Investors
Advisor-first, not direct-to-consumer
- iCapital is a B2B2C business, not a B2C platform.
- The firm’s clients are primarily financial advisors and general partners (GPs) seeking to reach those advisors.
What the platform provides
- For large advisors: a white-labeled operating system for alternatives, structured products, and annuities.
- For smaller advisors: a marketplace with access to hundreds of funds.
- The goal is to make alts easier to:
- evaluate
- subscribe to
- monitor
- report on
- integrate into client portfolios
The Operational Complexity of Alternatives
Why alternatives are hard to scale
Calcano notes that every private investment tends to be a different “widget,” with unique operational demands:
- onboarding
- subscription documents
- capital calls
- custodian coordination
- performance reporting
- analytics
iCapital’s solution
- The firm uses technology to manage the entire lifecycle:
- pre-investment education
- portfolio construction
- fund research
- subscription automation
- post-investment administration
- The intent is to give advisors time back so they can focus on clients rather than paperwork.
Illiquidity, Investor Expectations, and Education
Why investors misunderstand liquidity
- Calcano argues that many investors hear what they want to hear when it comes to “semi-liquid” or evergreen structures.
- He stresses that underlying private assets are still illiquid, even if the wrapper has limited redemption features.
His framing
- Investors should buy these products with a medium- to long-term horizon.
- Liquidity features are flexibility tools, not a signal that the underlying asset is liquid.
Education is essential
- iCapital and its GP partners spend significant time educating advisors and clients.
- Transparency and realistic expectations are central to avoiding misunderstandings during periods of stress.
Growth in Private Markets and Advisor Demand
Why alts are gaining share
Calcano points to several drivers:
- the search for incremental returns
- portfolio diversification
- access to a much broader set of companies than public markets offer
- the decline in yield from traditional fixed income during the ZIRP era
Where private credit fits
- Private credit became especially attractive when rates were near zero.
- Even as rates rose, private credit remained compelling because many loans are floating-rate.
- He believes current portfolios are likely healthier than many people assume, even amid headlines about stress in parts of the market.
Key bottleneck: advisor education
- Many advisors still have not fully adopted alternatives.
- Scalable adoption will require more education and more model-based portfolio construction.
Models, Portfolio Construction, and International Expansion
Model portfolios are becoming more important
- Calcano believes models will play a bigger role in how advisors allocate to alternatives.
- These may include:
- models for alts only
- models combining liquid and illiquid assets
- packaged exposures across multiple private strategies
Global opportunity
- Demand outside the U.S. is rising, though adoption lags behind the domestic market.
- iCapital already has significant international reach:
- $65 billion+ in alternatives allocated by non-U.S. investors
- about half of its offices outside the U.S.
AI, Tokenization, and the Future of Asset Management
How iCapital is using AI
Calcano says AI is being tested across the platform in both:
- client-facing workflows
- internal operations
Examples include:
- generating fund sub-documents
- helping clients describe preferences in the marketplace
- aggregating and extracting held-away client data
- document processing and data reassembly
Broader industry impact
- He sees AI, tokenization, and blockchain as major enablers, but says the industry is still in the early stages.
- Better data connectivity across custodians, administrators, transfer agents, advisors, GPs, and platforms could produce major efficiency gains.
Strategy, M&A, and Culture at iCapital
Build, buy, and partner
- iCapital has completed 24 acquisitions and continues to pursue M&A.
- Calcano says the firm only buys what it can fully integrate.
- Integration matters for both:
- technology
- culture
Recent capital and expansion
- A 2025 capital raise valued the company at a multi-billion-dollar level.
- iCapital continues to use capital for acquisitions, including the planned purchase of Hexure, which strengthens its annuities platform.
Culture and “one iCapital”
- Calcano emphasizes a strong, unified culture.
- He views leadership as making sure people are in the right roles and working toward a shared mission.
- One of iCapital’s cultural principles: clients come first.
Public vs. Private Markets: Where iCapital Fits
Public company discipline
- Although iCapital remains private, Calcano says the firm tries to operate with public-company discipline:
- fast monthly reporting
- fast quarterly closes
- strong balance sheet management
Employee ownership
- All employees have stock in iCapital.
- Because equity is part of compensation, the firm has created limited liquidity opportunities for employees over time.
Key Advice and Personal Takeaways
Advice for young professionals
- The world owes you nothing.
- Success comes from work, flexibility, and a strong attitude.
- Calcano stresses the value of learning by being in the room with experienced people, rather than only working remotely.
Advice he wishes he’d known earlier
- Be patient.
- Don’t overreact to one bad point, one bad quarter, or one bad cycle.
- His favorite analogy: in golf, or in a long career, “it’s just a point.”
Core philosophy
- Adapt to change.
- Stay intellectually honest.
- Focus on clients.
- Treat technology as a tool for better outcomes, not as a replacement for human judgment.
Bottom Line
Lawrence Calcano frames iCapital as infrastructure for the modern private-markets era: a platform that helps advisors access, explain, and manage alternatives without losing sight of client needs or operational complexity. His broader thesis is that private markets, AI, and data-driven workflows will continue to reshape asset management—but the winning model will still be human advisors using technology well.