The Memo

Dhruv Basu on the Big Bets Reshaping Chicago Real Estate

Ricardo Chamorro — Fri, 09 Oct 2026 08:00:00 -0700

A credit trained investor is making a $3.8 billion district pencil on 48 acres of Chicago lakefront, and he is doing it inside a 20 person shop that leans on AI harder than most institutions ever will. Dhruv Basu, Director, Investments at Farpoint Development, came to development through fixed income at Goldman Sachs, a stint on Mayor Ben McAdams' housing council in Salt Lake County, and Chicago Booth. He talks with Ricardo Chamorro about opportunity cost, the Michael Reese site, repositioning on the Magnificent Mile, and where he draws the line on what AI touches.

Chapters:

00:00 Lean into it before the bear catches you

00:35 What The Memo is

01:09 Meet Dhruv Basu and the Farpoint 48 acre district

01:52 From accounting to Goldman to development

02:40 Salt Lake housing council and buying a shopping center

04:59 What a credit brain sees that developers miss

06:34 The five eggs and opportunity cost

07:24 What Booth taught about the time value of time

08:07 Inside the 48 acre Bronzeville site

09:42 Managing city, community, and equity stakeholders

10:23 How a 20 person team splits the work

12:40 Repositioning on the Magnificent Mile

15:53 What outsiders get wrong about Chicago

17:21 Technology then versus now in development

19:20 Is AI a bigger wave than everything else

21:00 Where AI unlocks hours in a lean shop

23:22 Why lean shops move faster than institutions

25:43 Running alongside the beast, not fighting it

26:53 A foundation settlement example

28:20 Why a beast and not a rocket ship

29:59 Will AI ever replace judgment

31:42 What Dhruv hands over and what he won't

34:10 The risk of the gap getting wider

35:43 Would he take the same path again

37:23 Chicago, no regrets

38:09 Advice for someone starting out in 2026

40:17 The one AI move to make this year

41:58 Rapid fire

You can follow Dhruv Basu here:

LinkedIn - https://linkedin.com/in/dhruv-basu-48479562

Learn more about Farpoint Development:

Website - https://farpointdev.com

Making Housing Affordable with Michael Behot

Ricardo Chamorro — Fri, 25 Sep 2026 08:00:00 -0700

Affordable housing operators work the expense side of the statement because their income is capped, while market rate teams fight for every tenant on the income side. Michael Behot has run both books. As VP of Asset Management at RPM Development Group in Montclair, New Jersey, he moved from institutional market rate work at Heritage Capital Group and Castle Lanterra into regulated affordable housing, so he can say where AI already earns its keep in accounting and billing, where it fails on compliance, and why the local data that never got built by hand in 2012 is now within reach.

Chapters:

00:00 Two sides of the same business

01:00 From DC development to affordable housing in New Jersey

02:44 What an asset manager does all day

04:36 Moving from good to excellent at the job

05:18 Why equilibrium matters more in affordable housing

06:35 What each side gets wrong about the other

08:41 RPM's in-house model and its tradeoffs

10:34 Specialized knowledge of subsidy programs

11:17 Old buildings given a second life

13:20 LIHTC versus Section 8, explained

16:40 What separates a building that runs well from one that doesn't

17:56 Finding and keeping great site staff

18:33 What RPM has tried with AI so far

21:21 The gap between AI ideas and implementation

22:42 Will AI widen the gap between big and small firms

24:00 Why AI usage clusters in leasing and resident communications

26:42 The compliance problem AI has to get perfect

28:34 The data side and building a property income database

34:08 What would actually unlock more affordable housing

36:53 AI, faster approvals, and cutting red tape

40:17 Reaching residents and one-off affordable units

41:00 Rapid fire: strange buildings and career advice

You can follow Michael Behot here:

LinkedIn - https://linkedin.com/in/michael-behot-6aa28017

Learn more about RPM Development Group:

Website - https://rpmdev.com

Smelling the Gunpowder with Mark Conroe

Ricardo Chamorro — Fri, 11 Sep 2026 08:00:00 -0700

AI can translate a 90 page Spanish contract in three minutes, then tell you to hire a lawyer anyway. Mark Conroe, Managing Partner and Founder of Presidio Development Partners, has spent 40 years developing apartments, hotels, office, and retail across the Bay Area, building Cisco's and Adobe's first campuses and running two national companies before starting his own firm. He tells Ricardo Chamorro where AI gets him fast, where it sends him down dry holes, and why the last mile still runs on wisdom, experience, and knowing how to read a room.

Chapters:

00:00 The next lifetime: gratitude and coming back to the start

01:20 Meet Mark Conroe: 40 years of Bay Area development

02:10 From Stanford engineering to real estate, and Silicon Valley before the name

03:44 Why real estate is slow to adopt new technology

04:35 Building Cisco's and Adobe's first campuses

05:51 Comparing development in Boise and San Francisco

06:46 The technology waves that changed the work: calculators, cell phones, email

08:20 Recorded meetings, litigation, and letting AI into everything

09:57 Handwritten spreadsheets and hidden errors

10:43 The Baja land deal: 90 pages of Spanish and the lawyer he still hired

12:19 The last mile problem: getting to 8 out of 10

13:03 Backcasting a dock approval to test how AI thinks

14:54 Average answers versus the exception, and smelling opportunity

16:10 Can the next generation earn wisdom AI can't give them?

17:10 Who gets supercharged and which jobs stay human

18:52 Where Mark finds the most time savings day to day

20:12 The chainsaw joke: integration and implementation

21:52 Going paperless first, and cutting off hundreds of vendors

23:19 San Francisco's boom and bust economy

25:02 Living through the downturns since 1985

28:04 Why the last San Francisco crash was self induced

29:45 Starting Presidio Development Partners and the entrepreneurial itch

33:09 The cultural shift toward entrepreneurship

35:16 What Mark would tell a 25 year old starting today

39:28 Catching the apple before it hits the ground

41:21 Data centers, taking a position, and playing the long game

43:41 A contrarian AI take for firms that want to go paperless again

45:58 Smelling the roses versus smelling the gunpowder

47:22 The balancing act: check the work or fall behind your peers

49:10 The fastest way to get fired: handing off raw AI output

51:44 The next lifetime and what still brings Mark back to the table

Learn more about Presidio Development Partners:

Website - https://presidiodp.com