Coby Lefkowitz calls himself "not normal". Not because he's special, he's quick to clarify, but because he's willing to do something that barely makes financial sense: try to create beautiful buildings in New York and California, two of the hardest places to build in the US.

He's an urbanist, real estate developer, lecturer at NYU and author of Building Optimism: Why Our World Looks the Way It Does, and How to Make It Better. He also writes the Building Optimism Substack: https://buildingoptimism.substack.com

I reached out to Coby while researching an essay on how inflation leaves its mark on our buildings. He may not share my monetary thesis, but few people are as vocal or as thoughtful about why so much new development feels the same.

As Coby puts it: "We all intuitively feel something has been lost, but it's difficult to give language to that."

It's essential viewing for anyone working in real estate, planning or architecture, or anyone who's walked down a new street and wondered why it feels the way it does.

Coby is an old romantic in a world of yields, and IRR, and price per sq ft. But he's also a commercially savvy operator: clear-eyed about why building this way barely works, and doing it anyway.

The line I keep coming back to:

"As I work through my career to build enough of my own capital to create structures that will reinvest and compound back on themselves, such that in two to five to eight to ten generations… the efforts that I plant today may be enjoyed by posterity."

— Coby Lefkowitz, Orientation, Episode 3

I also write a short reflection after speaking with each guest, published on my Substack. Here's the one from this episode: https://orientationfrom.com/p/one-lesson-from-coby-lefkowitz

Timestamps:

(00:00) Introduction

(02:17) Students, wealth, and doing well by doing good

(04:59) The Great Wave, and why buildings look the same

(07:16) Zoning codes and the first wave of homogenisation

(11:10) The American dream, and the cookie-cutter box

(15:48) Milton Keynes, and schemes that wouldn't be viable today

(17:51) What have we lost along the way?

(23:46) Pension funds, rational actors, and the catch-22

(26:53) Does it have to be this way?

(28:51) Social reformers, critics, and the fear of beauty

(34:27) Why it's so hard to be a small developer

(42:12) Inflation, bond yields, and the race around viability

(43:39) Our homes, our high streets, and the Jewellery Quarter

(47:26) Culture or cost? Why historic buildings could afford ornament

(51:05) Permanence, and buildings that don't last

(53:52) Fund cycles, IRR, and the reward for selling early

(58:36) Battersea, patient capital, and purchasing power

(1:00:02) The great estates, Santa Barbara, and building for posterity

(1:08:45) The world as a series of decisions

(1:12:07) Poundbury, and learning from the new towns

(1:14:25) What shaped Coby's worldview

(1:18:02) Closing thoughts, and where to find Coby

Jor showed up every day for his first 100 livestreams with just three people in the chat. He’s now 579 shows in, with no sponsors - a tight-knit community funds it - and enough separate income streams that no single one can sink him.He left a career in accountancy to do this. He broadcasts his ‪88 SATS‬ show daily from the Canadian bush, surrounded by trees, four years after deciding he'd had enough of where he was. The show is completely unscripted. Some days it runs an hour, some days three.Jor has played a vital role in my education around the case for Bitcoin. More than that, though, he taught me that we can choose how to live: we don’t just have to accept the version of life we’re currently living, but instead have the agency to change it. That idea is the spine of this conversation: the pursuit of a more sovereign life, one that feels more aligned with your values and what you actually want.There’s a lot of practical guidance in our discussion. We cover relocation and physical sovereignty, digital privacy and security in the AI era, cultivating income streams as a solo operator, and navigating the tension of creating content and building a community versus relying on centralised platforms like X or YouTube.It’s educational viewing, especially for anyone considering moving out of traditional employment and starting to work for themselves. For me, it gets deeper from (45:00) onwards.Jor is a raw nerve, fiercely independent and unfiltered. What I admire most is that none of it comes at the expense of his belief in people.The line I keep coming back to:“It’s all proof of work. There’s no shortcuts. Everything has to be earned. And the only way that you can earn that is through time and effort and energy.”— Jor, Orientation, Episode 2I also write a short reflection after speaking with each guest, published on my Substack, Here's the one from this episode: https://orientationfrom.com/p/one-les...Timestamps:

(00:00) Introduction(02:33) Physical sovereignty: why Jor left the city(07:00) Fear, agency, and what we're taught to accept(09:51) Leaving the country, and why there's no perfect place(13:30) Your life is what you think about(15:45) Responsibility, and what sovereignty asks of you(18:38) Digital real estate: Rumble, Nostr, and renting your platform(23:00) The wheel of income, and the streams that feed the ocean(25:06) AI, memory, and what happens when nothing is forgotten(31:59) A more private future: your own server, your own data(36:39) Public Wi-Fi, VPNs, and paying without a trail(39:30) Passwords, and the era most people haven't caught up to(42:30) Owning your media, and your browsing(45:30) Going out on your own: you're not competing with anyone(49:30) Blocks in your chain, and the only person you're competing with(52:49) Financial sovereignty, and why Jor won't hold an ETF(54:02) Three things that make Bitcoin different(59:56) A peaceful revolution, and The Sovereign Individual(1:05:05) Sovereignty without the bunker(1:09:37) 579 shows, and the first 100 with three people watching(1:14:35) Where to find 88 SATS

Joining the show is Ricky Zhang, who was previously a successful travel creator, racking up 19 million views on YouTube sharing his experiences jet-setting around the world.

He also built Prince of Travel, a business helping people maximise credit card points and miles: unlocking travel, including first class flights, that most would otherwise think unattainable.

We speak about Ricky’s transition from CEO and travel creator - and the hedonistic influencer lifestyle that accompanied it - to hosting a daily live show Age of Abundance‬ that while simple in its design, sees him think aloud, attempting to find clarity in the financial and technological shifts we’re living through.

The crux of the discussion is Ricky’s newfound faith in Bitcoin and how he sees it as a solution to the current woes in our financial system, where the ability to expand the money supply drives inflation, a higher cost of living and inequality he thinks has become grotesque.

The line I keep coming back to:

“We don’t see the counterfactual, right? We just see the current state and we don’t see what the cities could look like if we did in fact have sound money, if we did in fact have incentives that pointed in the direction of low time preference and a longer time horizon.”

— Ricky Zhang, Orientation, Episode 1

Timestamps:

(00:00) Introduction

(01:18) Leaving Prince of Travel, and the stillness after

(05:40) Seeing the earlier self in hindsight

(09:33) Activation thresholds: how a transition starts

(12:45) Agency, disagreeableness, and who moves first

(15:25) What the debt-based system actually is

(21:10) The visible signs of a fraying system

(28:48) Why Bitcoin, and why not something else

(36:23) Neutrality, nodes, and Satoshi's anonymity

(42:34) The hard questions: crime, bubbles and Ponzis

(48:52) AI, work, and the vanishing junior job

(54:06) Polarisation, young people, and the third path

(59:00) Where we find meaning

(1:07:26) Closing thoughts, and where to find the show