How I Blew an Opportunity to Help Brian Chesky

Paul Hosch
Career Resource Institute
5 min readDec 13, 2016

I learned a massive lesson a few nights back. I was scheduled to meet a close friend — a brother, really — who was in LA on business.

We couldn’t figure out a good time to connect. So, to kill two birds, he invited me to an AirBnB reception he was scheduled to attend. We figured we’d bounce if it was a bore.

I arrived early, as I loathe not being on time. If you’re not 15 minutes early, consider yourself late. I’d had a long day so wasn’t up for making small talk with strangers. I just wanted to chop it up with my boy when he arrived, so I grabbed a complimentary chardonnay, found an awesome view of downtown LA — it was a rooftop reception — and waited. My friend shows up, we catch up and then quickly move on to how our respective businesses are doing. He’s killing it — traveling the world, Cape Town Friday — I’m in perpetual beta, but that’s another story.

As he’s telling me about his latest presentation to a 5,000-plus person audience, I look up and notice Former Attorney General, Eric Holder, talking with guests right next to our table. Then I recalled reading something about AirBnB hiring Eric’s law firm, but my friend and I can’t really be bothered to discuss that at the time — we’re talking about our passions. You know how it is.

Side note: It’s a blessing having a friend/brother who really gets it and is doing it himself. To actually like to help each other out with honesty, encouragement, and advice. And, to talk books. When one of us reads a good one, we nag the other to read it until they do. I am lucky to have Romal Tune in my inner circle.

We decide to leave the pool area — get away from the reception to order real drinks at the bar — my usual greyhound and his usual “something new” — a St. Germaine — a pretty damn good drink. Romal was hungry, so we decided to leave the event and find some food. While he tipped the bartender, I noticed the AirBnB crowd gathering for a speech. I waved Romal over and we went back to the pool area to listen. Romal was somewhat indifferent and immediately started texting. I listened to the AirBnB regional guy and then Eric Holder. Then, CEO and Founder of AirBnB Brian Chesky took the mic. Now I’m really interested. Romal pockets his phone.

Brian talked about some intimate family stuff — his mom and dad were present. His words were quite touching. Then he talked about Experience, which he had launched earlier that day. He appeared to be a really thoughtful and regular kind of guy. In other words, approachable.

Brian finished, people clapped, he stepped down into the crowd and atypically, no one swarmed the $3B Founder as would usually happen at such an event. Romal is now ready to leave. I say, “Wait, you don’t want to talk to him!?” “Nah, let’s just go,” Romal responds. One thing I like about Romal is he has a strong sense of himself and believes he is equal to all. In fact, he often exudes the sense that others who are considered more successful would benefit from knowing him — and less so the other way around.

Somehow we’re still there five minutes later and Brian ends up standing next to us, clearly ready to leave. I prod Romal again, “Are you sure you don’t want to say something?” “Nah,” he replies. Next, I check to see if I have everything and when I turn to leave, Romal and Brian are in a clearly meaningful conversation. I’m stunned. Eventually, Brian’s assistant walks over and encourages him to hurry as they have another event to attend. Brian staves the assistant off, pulls out his phone, and takes down information Romal is nonchalantly providing. Not knowing what else to do, I offer to take pictures…lol…don’t judge me.

Later, I ask Romal what the heck they were talking about. Romal replies, “I asked him why such a cutting edge tech company like AirBnB is handling its diversity in such a low tech manner.” That’s when I recalled hearing Brian ask Romal if he had any suggestions and that’s when he pulled out his phone to take down Romal’s information.

Now I’m looking at Romal wondering, “How the hell did you think of asking him the perfect question reflecting an opportunity for AirBnB’s that coincidentally lines up with exactly what you’re best equipped to help them meet?”

During dinner, it dawned on me — my massive lesson: Memorizing a great elevator speech isn’t enough. You have to be more prepared than that. Romal exhibited he is prepared with the following when he knows he may meet someone new:

1) Ready to help anyone, authentically, large or small with a need or a challenge he’s uniquely qualified to address.

2) Ready with his story (his elevator speech) to illustrate his credibility.

3) After connecting 1 and 2, he presents an immediate call-to-action.

Unsurprisingly, being the thoughtful down-to-earth guy I initially suspected he was, and just plain trying to get things right, Brian emailed Romal to tell him he appreciated the information and he’d be in contact soon. Who does that in this day and age!?!

If I had a do-over, this is what I would say to Brian:

1) “I understand you’re working to improve your diversity profile. I applaud you doing that. You’d be surprised how many companies ignore such challenges. Have you considered hiring strategically and diversely? Everything meaningful and long-lasting starts within, not without.”

2) “I run Career Resource Institute, a small career-oriented platform. We’re a hub for curated career service providers and employment information.”

3) You might consider working with firms that specialize in diverse hires? You don’t pay them if you don’t find good hires. Here’s my card. Let me know if I can help you find a firm appropriate for your industry. And thanks for putting on this nice reception. I enjoyed your candid remarks at the podium.”

An elevator speech requires too much work connecting the dots as you delivery a silique to prospective constituents. Connecting the dots, painting the picture — that’s your job!

What’s the best or worst elevator speech or sales pitch you’ve delivered or have had delivered to you when brevity is key?

Oh, and here’s the photo of me and Brian Chesky
And, here’s one with Romal and Brian (I can’t figue out how to enlarge Romal’s picture)
Coming Soon! …still in beta… www.CareerResourceInstitute.com

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Paul Hosch
Career Resource Institute

Paul Hosch, Founder/CEO of NFM, supports religious institutions in fundraising. Notable partners: The Emory Fellowship, St. John's UMC, and SBC21.