Regular appearances on Cheddar TV from the floor of the New York Stock Exchange, covering technology M&A, IPOs, startup ecosystems, and what makes companies endure.

Lylan Masterman discussing WeWork's acquisition of SpaceIQ on Cheddar TV
Cheddar TV · NYSE

WeWork Acquires SpaceIQ

Commentary on WeWork's acquisition strategy and the broader co-working and office space technology landscape.

Lylan Masterman discussing the Peloton IPO on Cheddar TV
Cheddar TV · NYSE

Peloton Going Public

Analysis of Peloton's IPO and what the $4.15B valuation signaled for the DTC fitness and consumer hardware market.

Lylan Masterman discussing the 2019 IPO landscape including Beyond Meat and Zoom
Cheddar TV · NYSE

The IPO Landscape

Beyond Meat, Zoom, and Lyft — the wave of 2019 tech IPOs and what their public market debuts revealed about venture-backed exits.

Lylan Masterman discussing pandemic-era grocery transformation on Cheddar TV
Cheddar TV · Remote

Transforming Grocery Stores

How the pandemic accelerated curbside pickup, grocery delivery, and the fundamental transformation of retail.

NYC's Growing VC & Startup Prowess

A 47-page report on the state of Venture Capital in NYC and the US East Coast, analyzing the region's rapid growth as a startup ecosystem.

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Inside the Mind of a New York VC

An in-depth interview on the NYC venture capital landscape, the operator-to-investor transition, and what makes White Star Capital's approach distinct.

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How People Mess Up One Crucial Slide in Their Pitch Deck

A breakdown of why founders manipulate the axes on their competitive analysis slide — and why investors see right through it.

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The Entrepreneur Playbook for Sourcing a Lead Investor in NYC

A practical guide for founders navigating the New York venture capital landscape and finding the right lead investor.

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For Women in Tech, Bias Runs Deeper Than Most Think

An examination of the systemic bias against women in the technology industry. Became my most widely shared piece of content.

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Women in the Boardroom: The Most Underrepresented CxO Role

Co-authored with Jay Rosenzweig. Examines the underrepresentation of women in CTO roles — the most underrepresented CxO-level position.

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The Future of Conversational AI

A prescient 2016 piece envisioning a world where bots could chat like Stephen Covey, Malcolm Gladwell, and The Dalai Lama — years before large language models made it real.

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3 Reasons That Blameless Retrospectives Build Trust

How blameless retrospectives create open, candid team environments and build lasting organizational trust.

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Venture Studio with Dave Lerner

Discussion on investment approach, portfolio companies, board responsibilities, and transatlantic venture capital.

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The Successful Pitch with John Livesay

On branding, investor passion, and what makes a pitch presentation resonate with VCs.

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Canadian VC & Startups with Kent Lindstrom

A deep dive into the Canadian venture ecosystem, startup culture, and cross-border investing.

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Kruze Consulting with Scott Orn

A 42-minute conversation on venture capital careers, the NYC startup ecosystem, board membership, and diversity in VC.

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