Generous by Design: Mike MacCombie on Loss, Community, & Venture Building | Alone Together

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Alone Together: The Story of Solo Venture Capitalists

Sidecut Ventures

12 episodes

6 hours ago

Alone Together reveals the personal journeys of today’s solo General Partners—investors who dare to go it alone. Hosted by Mike Ma, founder of Sidecut Ventures, each episode dives into the triumphs, challenges, and camaraderie that shape these emerging one-person firms. Far from lone wolves, solo GPs are forging a dynamic community—driving innovation for founders, limited partners, and other venture investors. Tune in to discover how these independent fund managers are reshaping the venture ecosystem—and why going solo doesn’t mean going it alone.

Investing

Business

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Investing

Business

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Generous by Design: Mike MacCombie on Loss, Community, & Venture Building | Alone Together | S1E8

Alone Together: The Story of Solo Venture Capitalists

49 minutes 24 seconds

7 months ago

Generous by Design: Mike MacCombie on Loss, Community, & Venture Building | Alone Together | S1E8

“When people are around, things will be more okay.”

In this heartfelt episode of Alone Together, I sit down with my good friend Mike MacCombie, founder and GP of Generous Ventures (disclosure: I am a very small LP in his fund).

Mike opens up about the profound impact of losing his mom at age eight and how that formative experience shaped his unwavering commitment to building communities that ensure no one feels alone. From aluminum foil casseroles in Ohio to building vibrant WhatsApp networks in New York, Mike connects the dots between personal loss, behavioral science, and his distinct approach to venture capital.

Beyond his powerful personal story, we discuss Mike's innovative strategies for running Generous Ventures, including his pre-seed deal-sharing calls, disciplined community management, and thoughtful LP relationships—strategies that have resulted in an astonishingly high close rate among investors. Mike candidly shares both the challenges and breakthroughs he's experienced as a solo GP and the lessons he's learned along the way.

Mike's journey illustrates how personal adversity can deeply inform one's professional approach and investment philosophy, emphasizing the importance of community as both an emotional anchor and practical asset. Effective community building is rooted in clearly defined purpose and disciplined management, underscoring that meaningful connections must be intentionally cultivated rather than passively formed.

This conversation is a testament to the power of generosity, vulnerability, and intentional community building in venture capital and life.

Chapters

00:00 Introduction and Background

03:06 Generous Ventures: Fund Overview

05:13 Personal Journey and Influences

09:35 The Role of Community in Venture Capital

16:02 Building WhatsApp Groups for Investors

21:43 Organizational Strategies and Tools

24:21 Pre-Seed Deal Sharing Calls: Concept and Evolution

27:54 The Power of Generosity in Deal Flow

29:41 Lessons in Community Building

32:26 Artisan vs. Algo Funds

37:17 Advice for Aspiring GPs

43:29 Reflections on Highs and Lows