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.

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.

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.

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.

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.

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.

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.

3 Reasons That Blameless Retrospectives Build Trust

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

Venture Studio with Dave Lerner

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

The Successful Pitch with John Livesay

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

Canadian VC & Startups with Kent Lindstrom

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

Kruze Consulting with Scott Orn

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