When to Sell into Secondaries

How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest.

Highlights:

• How 20 years in venture reshaped Mark’s thinking on risk, liquidity, and exit timing.
• Why early VCs get caught in the “TechCrunch punch” and over-index on hope.
• Power laws vs. portfolio consistency — why vintages swing and how Mark mitigates volatility.
• How secondaries, tenders, and mid-market PE can drive liquidity for the “middle 80%” of winners.
• The “tweener rule”: why Interplay often sells ~50% when outcomes are unclear.
• Incentive alignment between GPs and LPs — and why building a long-term institution changes behavior.
• Avoiding narrative traps: why founder behavior and fund construction matter more than storytelling.
• Brokerage-model VC vs. operational-institutional VC — and why the difference is huge.
• How soft commits, goodwill, and reference strength drive proprietary access.
• Entrepreneurship patterns: the “500 problems” every startup faces.
• Why you can’t learn entrepreneurship in a classroom — only through reps.
• The compounding effect of grit and staying in the game long enough.

Guest Bio:

Mark Peter Davis is a venture capitalist, serial entrepreneur, author, and startup community organizer.

MPD is the Managing Partner of Interplay, a startup ecosystem based in NYC that supports founders and innovation at every stage. The ecosystem comprises a top-performing venture capital fund, an accelerator, a studio, a services platform, and a multi-family office. With over 100 companies funded, incubated, or founded, he ranks among the most active startup founders and investors in New York City.

MPD is also an active podcaster, the author of The Fundraising Rules, and the founder of both the Columbia Venture Community and the Blue (Duke) Venture Community.

Prior to his current ventures, MPD was a venture capitalist at DFJ Gotham Ventures and Primary Ventures. Before entering VC, he was a M&A advisor to Fortune 1000 acquirers at KPMG and a strategy and operations consultant at Bain & Company.

MPD earned his BA from Duke University and his MBA from Columbia Business School.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#venturecapital #vc #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Mark Peter Davis:

LinkedIn: https://www.linkedin.com/in/markpeterdavis/ X/Twitter: https://x.com/mpd Interplay: http://interplay.vc/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com.

(0:00) Introduction (0:31) Evolution and counterintuitive lessons in venture investing (3:25) Reconciling investment worldviews and managing liquidity (7:35) Decision-making and aligning VC incentives with LP interests (12:03) Building an enduring institution and measuring success (18:07) Achieving access to competitive deals and proprietary deal flow (24:24) Competitive tension's impact on investment support (27:19) Integrity and resources in VC partnerships (30:02) Entrepreneurial experience's value in venture capital (32:24) Startups' challenges and the role of pattern recognition (35:24) Unlearning and cognitive restructuring in entrepreneurship (37:23) Mastering the complexities of long-term entrepreneurship (38:11) Timeless advice for aspiring entrepreneurs and enduring success (41:51) Closing remarks