Episode summary
"Venture is a Who Business, Not a What Business" | JD Montgomery
Superclusters The Emerging Lp Podcast
· · 1 hr 17 min · Hosts: David Zhou · Guests: JD Montgomery
Summary
JD Montgomery’s core message is that investing, parenting, and personal growth all hinge on intentionality and pattern recognition. He describes a twice-yearly “someday” planning day, usually on his birthday, spent offline reviewing decades of notes, setting 12-month goals, and asking what he wants the next phase of life to become. He uses that same long-horizon mindset to think about his own life curve, emphasizing continuous improvement, compounding, and choosing harder competition as he moved from high school to Stanford to his career.
That same framework carries into how he evaluates venture and private equity managers. Montgomery says he is in a “who business, not a what business,” and looks for people with a pattern of success, resilience, authenticity, and evidence they have endured adversity. He prefers net returns over gross, dislikes vague claims of proprietary deal flow, and thinks DPI matters when judging whether a manager can actually return capital. On early distributions and recycling, he argues for nuance: if capital can be recycled into strong opportunities, the GP should do it; if not, he wants money back in LP hands.
The conversation also turns personal. Montgomery says growing up without a father taught him what not to do, and he has built his life around being present, especially with his four children. He closes by saying the “good old days” are deep relationships, shared meals, and giving people real attention rather than digital distraction.
Key takeaways
- Montgomery’s investing filter starts with the person: he wants a GP with resilience, authenticity, and a real pattern of success, not a one-hit wonder.
- He says he cares about net performance and DPI, and he is wary of managers who show only gross returns or talk up proprietary access without proof.
- On early distributions, he favors recycling capital only when it improves the fund’s long-term opportunity set; otherwise, he prefers capital returned to LPs.
- His “someday” ritual is a twice-yearly, full-day planning session that turns old notes and questions into 12-month objectives and accountability.
- Montgomery says fatherhood is one of his most important jobs, and he built his family life around presence, routine, and intentional time with his kids.
Notable quotes
“I am not in a what business. I am in a who business”
“what you look for is demonstrate how you have been successful over many many periods of time in many different areas”
“one thing that is unique to private equity venture capital is you know persistence is a little easier because of brand”
How the episode opens
We probably all know somebody that was uh captain of the football team and like that's what they're talking about still. And so what you look for is demonstrate how you have been successful over many many periods of time in many different areas so that I know that you were just not lucky and rode the right course. Superclusters is where we demystify the secrets, stories, and tactics behind the money that moves the venture capital world.
There are some people in this world that are so wellknown among insiders that giving them an introduction is silly. And if you've been in the family office world since the 1990s, our guest today needs no introduction. JDM Montgomery is one of the foremost thought leaders on family offices, generational transition dynamics, as well as investing in emerging managers, having invested in 50 fund ones himself, not 15, 50.
JD Montgomery is the managing director of Canterbury that oversees more than $64 billion on behalf of endowments, foundations, and families. We'll get into JD's life story pretty quickly. So, I'll let you hear about his origin story from the man himself.
But I want to give a first shout out to the person who first put us in touch and urged me to get JD on the podcast, Talal at Steel Atlas. Without you, this episode, this friendship would not have been possible. So, finally getting off my soap box here, JD Montgomery.
We had last met, well, we would first met in person and then we had subsequent calls after, but when I met you in person, you were telling me all your stories and uh you being a Coxwin and and uh you cooking, I knew outside of all those things as well as how you think about relationships, I had to have you on.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- venture capital persistence
- family office strategy
- gp relationship building
- capital deployment and recycling
- venture fund performance metrics
Companies and tickers mentioned
- AMZN
- SHOP
- Canterbury Consulting
- Amazon
- Shopify
- Founders Fund
- Picnik
Watch the episode
Watch “"Venture is a Who Business, Not a What Business" | JD Montgomery” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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Superclusters The Emerging Lp Podcast, this episode and its artwork belong to Superclusters by David Zhou. Octagon is not affiliated with the show; this page is an independent summary.
