Today's episode explores three ideas that caught my attention:
① Collectibles are built on story: Vasu explains why a game-worn jersey, a rare watch, a ticket stub, or a trading card is not valuable because of raw materials. It is valuable because of the story attached to it.
② The hunt is the utility: For serious collectors, the joy is not only in owning the item. It is in the search, the community, the chase, and the feeling of finding something rare that almost no one else can access.
③ Collectibles need infrastructure: Watches, cards, memorabilia, sneakers, handbags, and art become more valuable, the market needs better marketplaces, insurance, financing, shipping, authentication, vaulting, and liquidity.
Vasu has spent his career at the intersection of sports, startups, venture capital, and collecting. In this conversation, he shares the bull case for collectibles as an asset class, why physical collectibles may have staying power in an AI-driven world, and what angel investors should look for when evaluating companies in this market.
During our conversation, Vasu shares:
Why collectors form such strong communities.
How COVID accelerated interest across collectible categories.
Why the hunt matters more than the object itself.
How utility objects become hobbies, then asset classes.
Why story drives value in watches, art, jerseys, ticket stubs, and trading cards.
Why scarcity and supply discipline matter so much.
How the internet changed global liquidity for niche collectibles.
Where Courtside Ventures sees opportunity in collectibles infrastructure.
Why insurance, financing, shipping, and logistics are becoming more important.
What angel investors should ask when collectible deals hit their desk.
0:00 The story is the asset
0:26 Introduction
1:26 Vasu Kulkarni joins the conversation
1:37 Why Vasu is excited about collectibles
2:55 How collecting became a global social graph
4:17 Why COVID accelerated collectibles
6:20 How collectors fall deeper into the hobby
7:38 Vasu’s top collecting categories
8:54 Collectibles as entertainment
9:58 The hunt is 99% of the fun
11:28 From utility to luxury to asset class
12:58 Why COVID accelerated the asset-class thesis
14:53 Collectibles as hobby, community, and hedge
16:20 Why story creates collectible value
17:52 The 100 greatest sports moments
19:13 What becomes collectible next?
20:11 Why almost anything can become collectible
21:31 Independent watchmaking and scarcity
23:39 How the internet changed collecting
25:20 Why community keeps collectors coming back
26:34 The “kidult” market
29:00 The Courtside Ventures origin story
30:07 Why sports looked non-venture-backable
31:52 Sports as a broader entertainment market
33:04 The Athletic and StockX
34:30 Vertical marketplaces for collectibles
35:24 Gamified collecting and pack ripping
37:10 Infrastructure around collectibles
38:12 Insurance, financing, and lending against collectibles
39:53 Shipping and logistics problems
40:47 Regulation and gambling-adjacent mechanics
41:13 Questions investors should ask about collectible startups
42:05 Average order value, LTV, and CAC
44:11 Supply discipline and overproduction risk
46:18 Why physical collectibles may hedge against AI
47:03 What NFTs missed
48:14 Collectibles as a hedge against digitization and inflation
49:50 Final advice: buy what you love
50:54 Closing
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