Ep 27 | The $9 Billion Bet on Vermont | How Rob Lair Is Building the Anti-Silicon Valley

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We've been talking about what makes a quantum city for a while now. Rob is in the middle of building one.

Rob Lair, co-founder of Hula Lakeside Investments, joined us this week and the conversation took on a life of its own. 

Eight years ago, Rob and his partner Russ Scully converted a vacant oven factory in Burlington, Vermont into what is now 150,000 square feet of coworking infrastructure — and layered on top of it a venture fund, a 100-investor network, and a thesis that private capital deployed by people who love their community is the most powerful force in economic development. Their portfolio grew from a combined $400 million in market cap to over $9 billion. One of their companies, Beta Technologies, just IPO'd at $7.5 billion. Their founder was Rob's neighbor.

The thread that ran through the entire conversation was leadership — specifically, the idea that GDP growth and business formation don't come from government or institutions. They come from private capital with a long time horizon and a genuine connection to place. Everything else, including housing, childcare, the zoning reform, follows from that.

In this episode:

• The Hula model: How bricks-and-mortar infrastructure that cash-flows at a 7% cap, combined with a community investment arm, produces something WeWork never figured out
• Place-based investing as a real edge: Why knowing your founders as neighbors — not as deal flow — is a structural advantage no coastal fund can replicate
• Why housing has to come first: Hula is breaking ground on 1,400 residential units in July because economic development without housing is, in Rob's words, a waste of time
• The CRE opportunity in tier 2 cities: Rob's practical framework for how a developer should be mapping capital formation and startup momentum as forward demand signals — not looking at comp supply
• Venture math and the right time horizon: Why failure is part of the economic development, why the PayPal Mafia effect is the whole point, and why a 10-year minimum clock is non-negotiable
• Appraisals are two decades behind: Banks are underwriting major projects with backwards-looking market studies while the data to do it properly already exists. Rob makes the case for what this should look like in an AI era
• State of venture in 2025: The post-pandemic recovery, IPO windows opening and closing, and why Rob won't accept that place-based investing means lower returns
• The next cities to watch: Portland, Maine is Rob's top pick. Boulder, Colorado is second. And none of this, he argues, is a zero-sum game with the tier one markets

Rob, thank you for joining us. This was one of those conversations we'll be thinking about for a while.

TIMESTAMPS:

01:19 Rob’s Origin Story

04:19 Building Hula’s Engine

07:36 Can Burlington Scale

13:37 What Cities Need

17:02 Winning Over Government

19:23 Venture Time Horizons

28:15 Place Based Capital

30:59 CRE Future Challenge

32:04 Capital Flows Forecasting

33:15 Hula Model Spreading

34:22 Placemaking Beats Backward Data

36:22 AI Underwriting Heatmaps

39:31 Designing For Company Lifecycle

42:32 State Of Venture Today

47:43 Alts And Capital Allocation

49:56 Smart City Data Vision

54:12 Rapid Fire City Metrics

56:14 AI Prompting Workflow

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