"Just Checking In"

What capital raising forgot about building human relationships

Two friends of mine recently raised $20 million for a multifamily development deal. In this market, which—if you’ve tried to raise for ground-up multifamily recently—you know is about as fun as a root canal with no anesthesia.

They didn’t use a placement agent or tap large institutional capital. And they certainly didn’t rely on mass email blasts to a thousand investors.

I asked them what worked, and the answer was so obvious it was almost embarrassing.

They went deeper on relationships they already had.

They went to dinners, remembered kids’ names, texted articles that had nothing to do with the deal, congratulated people on things that weren’t fundraises, showed up at events and didn’t pitch, and followed up when they didn’t need anything.

They did the actual work of building relationships that no one seems to prioritize anymore.

Probably because most GPs I talk to treat capital raising like a top-of-funnel problem…

• Build a bigger list,

• Blast it,

• If someone doesn’t commit in 60 days, mark them as dead and move on.

The entire capital raising process today is optimized for volume, which is a polite way of saying most capital raising strategies have just become email marketing with a higher minimum check size.

Meanwhile, there are probably 200 people sitting in your CRM right now who already know you, already trust you, and already understand your strategy. Half of them said “not right now” on your last deal — which you interpreted as “not interested.” It almost certainly meant “not right now.” People have a lot going on… their kid is applying to college; they’re closing on a house; they just started a new role; etc. Your $5 million capital call was not top of mind that particular Tuesday in March.

The problem is that maintaining 200 relationships at any real depth is a full-time job, and capital raising already sits on the most senior, most time-constrained person at the firm. So the quarterly update goes out, three people reply, and the rest slowly forget you exist. Not because the relationship soured, but because nobody watered it.

This is where AI gets interesting — and I don’t mean using it to write faster cold emails to bigger lists. That’s just spam with better grammar and a LinkedIn thought leader telling you it’s “scale.”

The real unlock is using AI to watch the people you already know and surface moments worth acting on.

Your investors are not just rows in a CRM. They’re people generating signals constantly across every public channel they touch — LinkedIn, Instagram, Facebook, their firm’s website, Google News, SEC filings.

• An investor’s firm just closed a new fund

• Someone you pitched last year just got promoted to head of real assets at a family office

• A contact just posted vacation photos from Nashville, where you happen to have a project under construction

👆 These are the opening lines of real conversations. And they produce outreach that actually deepens a relationship — not “just checking in” or “wanted to circle back,” which are both shorthand for “I have nothing specific to say but my CRM told me to email you.”

The relationship building workflows we’re building with a few groups right now looks like this.

1. You take your existing investor universe — everyone who’s ever taken a call — and build signal monitors across their public channels.

2. AI watches all of it, continuously, and surfaces relevant moments as signals.

3. AI drafts the follow-up — specific, short note tied to that signal, written in the GP’s voice and calibrated to the relationship.

4. The GP reviews it, tweaks it if needed, and hits send.

Thirty seconds instead of thirty minutes, which means it actually happens instead of aging on a to-do list.

The playbook looks more like what a great consumer brand does than what a traditional capital markets team does. The best DTC companies track customer behavior across every touchpoint and reach out at exactly the right moment with exactly the right message.

Investors are consumers too. They have social media accounts and life events and interests that extend well beyond their allocation mandate. The information is all public. Almost nobody in real estate is systematically using it.

The line between thoughtful and creepy is the senior person’s judgment (which is why the human stays in the loop). AI surfaces the signal; then the GP decides whether to act on it. That human filter is what keeps it personal instead of algorithmic, and it’s why this only works when the workflow is built around how a specific person actually operates, not jammed into some off-the-shelf sequence.

My friends who raised that $20 million didn’t use any of this technology. They did it the old-fashioned way — remembering details, checking in on people, showing up. It works because it’s genuine. What we’re building is the infrastructure to do that at scale without losing the part that made it work in the first place.

The biggest opportunity in capital raising right now isn’t finding new investors. It’s going deeper with the ones who already know your name.