Did Caissa Have Fun?

1. Zac showed up 20 minutes late. How did that make you feel?

Honestly kind of iconic — I like a man with zero regard for the clock.I respected it. Showed up late but still took the lead — baller move.Had me questioning if this was a Tides Equities underwriting model.Was ready to leave… until he started talking about IOS like it was religion.Late, but brought main character energy. So I forgave him.

2. The conversation included a 30-minute segment on institutional IOS. Your review?

Informative. I now know more about truck parking than my own portfolio.Didn’t ask, but somehow still wanted more. Mansplaining done right.I blacked out halfway but nodded along respectfully.He’s either insane or a visionary. Could go either way.Honestly? Would listen again. Add a deck next time.

3. Zac admitted to looking you up before the date. Your thoughts?

Due diligence is sexy. He’s clearly an underwriter at heart.Love the honesty. And mildly flattered.Slightly alarming… but also efficient. Respect.He probably knows my credit score too. Hot.Honestly? I looked him up too. Let’s not pretend.

4. Overall, how did the date make you feel?

Like I’d been pitched a JV deal and weirdly wanted to sign.Like I was back at HBS but this time... interested.Skeptical at first. Not expecting to get kicked out of our own reservation.Somehow charmed despite him not knowing how to hail a cab in Manhattan.Emotionally underwritten. Spiritually cash flowing.

5. If this date were a real estate deal, what kind would it be?

A fully paved Class A IOS site in Savannah — rare and oddly thrilling.A funky value-add with questionable zoning and a charming sponsor.An off-market deal someone begged me not to overlook — glad I didn’t.A quirky covered land play I’ll be thinking about for days.A once-in-a-cycle assemblage with… red flags I’m ignoring.

6. What should Zac plan for Date #2?

Cycling in New Jersey with a free bike tune up from Zac.Late-night rooftop drinks — no IOS talk until round 2.A property tour disguised as a date. I won’t fall for it again. Or maybe I will.A quiet night where no one mentions cap rates — just vibes.Surprise me — just not another 30-minute truck parking rant.

7. Do you think Zac is actually one of the top IOS brokers in the country?

Yes. He told me 5 times and cited sources.Probably. He made IOS sound like an elite underground scene.Unsure, but confident enough to sell me on it.He had charts. I trust it.Let’s just say… the man can lease.

8. Any final thoughts?

Thanks for the drink. And the unsolicited crash course on gravel lots.He’s lucky he’s charming. And tall. And mildly unhinged.Might’ve rolled my eyes once. Might’ve liked him anyway.10/10 would let him underwrite my soul.I laughed, I learned, I might respond to his next survey.

9. Would you invest in Zac’s next deal?

Yes — blind commitment. Wire already sent.Maybe… send the deck and some comps.Only if there’s no mysterious waterfall language.Absolutely not, but I’ll still get drinks again.I'm emotionally over-allocated, but tempted.

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