This Week in Startups

Portfolio construction, Sequoia's transition & Fast with Acquired.FM + The Dropout: This Week in Streaming with Lon Harris | E1429

Apr 8, 2022

Ben Gilbert, Managing Director at Pioneer Square Labs, and David Rosenthal, Co-founder of Kindergarten Ventures, delve into effective portfolio construction and the recent transition at Sequoia Capital. They discuss the downfall of Fast.co and what it means for the venture capital landscape. Lon Harris, a streaming media expert, analyzes the gripping finale of 'The Dropout,' sharing insights into its narrative and the broader implications for future seasons. This rich conversation blends venture capital strategies with engaging media analysis.

01:37:48

Creator website

Episode guests

Lon Harris

David Rosenthal

Ben Gilbert

AI Chapters

Episode notes

Intro

4min

Venture Capital Insights and Automotive Reflections

8min

High-Stakes Ventures: Balancing Passion and Portfolio Strategies

4min

Venture Capital Resilience in Changing Markets

5min

Investing in Resilient Businesses and Emerging Opportunities

3min

Strategic Investing in Tech Stocks

5min

Evolving Investment Strategies and Leadership Changes in Venture Capital

4min

Leadership Transitions and Cultural Crossroads

25min

The Perils of Rapid Growth in Fintech

5min

10.

Navigating Governance and Growth in High-Performance Teams

12min

11.

Innovations in Travel and Investment

6min

12.

Embracing Dialogue and Narrative Complexity

10min

13.

Ethics and Accountability in the Shadow of Fraud

7min

First, Ben Gilbert and David Rosenthal from Acquired join Jason to talk portfolio construction (13:41), Roelof Botha succeeding Doug Leone at Sequoia (30:58), and to debate the takeaway from Fast's demise (52:22). Then Lon Harris from Inside Streaming joins to discuss the final two episodes of The Dropout (1:24:16)!

(00:00) Jason intros today’s show
(1:31) Catching up w/ the http://acquired.fm guys: David Rosenthal and Ben Gilbert
(12:25) Fiverr - Sign up for https://Fiverr.com/Business free for the first year and save 10% on your purchase with promo code JASON
(13:41) Ben on investing in tech
(21:39) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist
(22:46) How David thinks about his capital allocation
(29:41) Notion - Get started for free at https://notion.com/thisweekinstartups
(30:58) Talking about Doug Leone’s retirement
(52:22) Talking about the elephant in the room: Fast.co shutdown
(1:24:16) Talking with Lon Harris about the finale of “The Dropout”

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