This Week in Startups

Peloton's new CEO + Cake Ventures' Monique Woodard Angel S6 E5 | E1383

Feb 11, 2022

Monique Woodard, Founder and Managing Partner at Cake Ventures, discusses her focus on investing in demographic change, emphasizing women's economics and the aging population. She shares insights on fundraising, comparing the challenges faced by founders to those of fund managers. Woodard explains her strategy behind multiple fund closes and why she caters to institutional LPs despite their longer timelines. The segment also highlights Peloton's new CEO, Barry McCarthy, his leadership style, and the evolving fitness subscription model.

01:27:13

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Episode guests

Monique Woodward

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Episode notes

Intro

2min

Peloton's Leadership Shift and Market Strategies

8min

Exploring Fitness Subscriptions and Customer Valuation

4min

Navigating Leadership Changes at Peloton

5min

Principles of Effective Leadership

7min

Navigating Morale Challenges Post-Layoffs

3min

Navigating Startup Investments and Essential Insurance Insights

4min

Navigating the Venture Capital Landscape

24min

Navigating Venture Capital Dynamics

29min

In the opening news segment, Molly and Jason break down the news around Peloton's new CEO, Barry McCarthy, including the open letter he sent to the company, his background and principles for success (2:05).

Then, Monique Woodard of Cake Ventures joins for Episode 5 of Season 6 of Angel (32:50). Monique was a founder, startup community leader, VC scout, and VC partner before raising her first fund.

In this episode you will learn:

Her thesis on investing in demographic change
What fundraising is like as a founder vs. fundraising as an aspiring fund manager
Why she chose to have multiple closes for her fund
Why Monique focused her efforts on institutional LPs, even though they take longer to close than individual LPs
What it takes to operate as a solo GP

(0:00) Jason and Molly tee up today’s topics: Breaking down Peloton’s new CEO background and leadership style and an amazing interview with Monique Woodard (Cake Ventures)

(2:05 ) Understanding Peloton’s new CEO and the value of its user base

(12:47) LinkedIn - Post your first job for free at https://linkedIn.com/angel

(14:15) Some more fun with numbers, plus breaking down Barry McCarthy’s introduction email to all Peloton employees

(21:43) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist

(22:54) Finalizing McCarthy’s “principles of success” list and reflecting on the difficulty of a turnaround

(31:32) Embroker - Get an extra 10% off insurance for your business at https://Embroker.com/twist

(32:50) Introducing Cake Ventures’ Founder & Partner Monique Woodard: Understanding Cake’s thesis on investing in demographic change

(42:20) Fundraising as a founder vs. fundraising as an aspiring fund manager, understanding how different types of LPs invest

(50:58) Check sizes differences from institutional LPs and individual LPs, understanding multiple fund closes

(1:07:18) Managing deal flow as a first-time fund manager, is the industry becoming more welcoming to underrepresented fund managers?

Check out Cake Ventures: https://cake.vc/

FOLLOW Monique: https://twitter.com/MoniqueWoodard

FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

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