Last Cast Letter #29: The Disappearing First Rung

Hi All - Happy Thursday. It’s the last day of the month, which means it’s time for the Last Cast Letter.

I missed the past two months. A couple of my buddies gave me some shit when we went to the Marlins game last week. I felt bad until one of them dropped a foul ball that made its way over to us while we were in the nosebleeds. It was hysterical. He definitely felt like less of a man after that.

Terrible mitts and two missed newsletters aside, it’s a nice reminder to surround yourself with people who hold you accountable. No excuses, but I was jamming on The Street Sheet. Check out the new website and tell me what you think. I’m biased, but I think it looks so fresh.

Before We Begin: A Quick Note

Earlier this week, as many of you already know, a tragedy unfolded at 345 Park Avenue, a building I used to work in. Wesley LePatner, the Global Head of Core+ Real Estate and the CEO of Blackstone Real Estate Income Trust (BREIT), was killed along with others.

I didn’t know Wesley personally, but I worked on the same floor with some of the people who helped build and launch BREIT. My thoughts and prayers are with Wesley’s family and the entire Blackstone community. It’s a devastating loss.

I also want to acknowledge and use this mini platform to pay tribute to NYPD Officer Didarul Islam, Aland Etienne, and Julia Hyman whose lives were also lost in the attack. May they rest in peace.

What Caught My Eye Over the Past Month

Now, over the past month, I’ve noticed a cluster of stories, tools, and trends that all seem to point in the same direction. I’m going to outline them below and try to tie them and my thoughts together, but I wanted to point out a few examples that stood out.

The first is Shortcut: a GPT-4-powered tool that builds financial models from scratch with a single prompt.

The second is Offdeal, which is positioning itself as an AI-native investment bank.

The third wasn’t a new company; rather, it was a prompt that one of my friends sent me, posted by CRE Analyst on LinkedIn. Go to Loopnet, grab a deal you like, and try this prompt, it’s actually pretty insane:

All three of the snippets above are examples of how fast the front-end work of investing is changing.

Then I saw a quote from Goldman Sachs CEO David Solomon that brought this all home. He shared that Goldman now uses AI to help draft public filings. An S1 filing, which might have once taken a six-person team two weeks to complete, can now be 95 percent done by AI in minutes. “The last 5 percent now matters because the rest is now a commodity,” he said.

That last line felt connected to something else I had just read.

The Disappearing First Rung

A recent Wall Street Journal article laid out how tough things are getting for new college graduates.

Fewer entry-level jobs are available, especially in white-collar fields like finance and real estate. Some companies are eliminating these roles entirely, choosing instead to automate much of the work.

In private equity real estate, this hits close to home. The typical analyst role, where a recent grad builds models, pulls comps, and preps early-stage deal materials, is slowly being replaced. Not because that work isn’t necessary, but because it can now be done faster by AI.

That’s a real shift. For decades, those jobs were how people broke into the industry. Lose those roles, and you lose the training pipeline that feeds the next generation of principals and partners.

Why This Matters Long Term

Some firms are trying to address the gap. Carlyle now runs an “AI University” to help analysts learn how to use these tools. A pipeline operator in Oklahoma added a new onboarding program that focuses on business fundamentals. But most companies are not doing this. And over time, that creates a hole in the talent development process.

We talk a lot in this business about judgment. But judgment isn’t something you hire for. It’s something you develop by doing the work. By building models, making mistakes, sitting in meetings, and learning how deals actually come together. You don’t get that kind of judgment if you skip the early reps.

What I’d Do If I Were a College Graduate

If I were entering the workforce right now, I wouldn’t let the changing job market discourage me. I’d adjust to it. Here’s how I’d approach it:

1. Still Learn the Hard Skills
   Even if you can’t land an analyst role right away, learn to underwrite investments and build financial models on your own. Get the reps in. When I was at J.P. Morgan in my first role out of school, I wasn’t building models every day. So I enrolled in night classes at NYU and took real estate finance and modeling. That effort helped me eventually land a job at Blackstone.

2. Relationships Matter More Than Ever
   Keep networking. Not just to get your first job, but even once you’re in a role. Build your Rolodex. Talk to people who are a few steps ahead of you. Share what you're working on. Most people are more willing to help than you think.

3. If You Can’t Beat Them, Join Them
   If your original plan was to go into investment banking and then pivot to private equity, but that path is now harder to access, consider joining the companies building the tools instead. Shortcut and Offdeal are two examples. These teams are on the front lines of change. And working with them could be just as interesting and valuable as working in traditional finance.

4. Learn Distribution
   This doesn’t have to do with real estate directly, but it’s something I’m seeing every day on the media side of my business. The cost of content creation is approaching zero. Words, photos, and even financial models are now easier to produce. But distribution is not. The ability to get your message in front of the right people is becoming more valuable. That’s why companies keep coming to The Street Sheet. We’ve built a list of 130,000 investors who actually pay attention. And it’s why I’m doubling down on building our own distribution. If I were starting over today, I’d take a serious look at marketing. Modern marketing, the kind built around trust and reach, is only going to matter more.

Final Thought

I believe AI will make the real estate investment process more efficient and scalable. But it’s still important to train people. If we phase out too many early-career roles, we may find ourselves with fewer experienced professionals down the line.

If you're thinking about how to put capital to work and want to talk about what we’re seeing across our deals and operations, I’d love to connect.

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— Brooks