Day 2: A Business Double-Date

It’s Day 2 of my #100rejectionschallenge and guess what — we have ourselves another SXSW-centered challenge.

What

This time, I decided to reach out to one of my favorite speakers, authors, marketers, and publishers of newsletters(?) whose name I will conceal out of respect. He’s at SXSW every year as a featured speaker and puts on a meetup and other events while in town. I started following his work in 2021 and attended one of his meetups in 2022, where I met him and his lovely wife. I reconnected with them in 2023 and more chats were had.

But in 2024, I’m approaching the conference (and life) a little differently …

Reeewind

Once upon a time, I was all about quantity. My mark of a successful (FOMO-fueled) SXSW would be the stack of business cards I collected and the plethora of ‘free food & free booze’ parties, activations, sessions, and meetups I attended.

But 40-year-old Nammy is different.

By now, I’ve seen some life. My tolerance for alcohol, junk food, crypto bros, and general BS has dramatically reduced. Now, I’m more about that JOMO (joy of missing out) life.

This year, rather than cram my itinerary with 100 things, I’m seeking more curated, meaningful experiences. That means quality 1x1 interactions with a select few. And because I’m not Oprah (yet), I’ll have to curate said quality interactions myself.

How

Now here’s the rub: I’m not a celebrity with a huge brand or bushels of clout. So what's a muggle to do when asking magical folk for their time? You find a way to add value!

In this case, I figured it would be easier to propose a double-date, or a 2x2, if you will. And that’s what I did.

One, because it makes things less awkward. But more importantly, I genuinely feel the speaker/author/newsletter-er and my partner (Andy) have overlapping interests and would benefit from knowing one another. I believe this is what business types call “synergy”. Gross.

Plus, with Andy and me being local foodies, I offered to show them around and introduce them to something new and authentically Austin in case they’re sick of the same old food trucks every year.

The Result(ish)

I crafted the email and sent it out last week with some trepidation. A few days later, I got this response from the wife:

Hey Nammy. Hello! Looking forward to seeing you at SX again and thanks so much for reaching out. [Husband] has a crazy schedule this month, as well as at SXSW - but I'll see if we can make it happen. We are in the midst of scheduling interviews and events at SX, so I will have a better idea of times that he's available early March. [Husband] is in town from Thursday to Monday - so I'm sure we can find a time to get together. Can you ping me back in early March?

Ok, ok. Not a hard YES. But what a nice response and definitely not a NO! I can deal with that. You best believe I’ll be following up in early March! (And updating this post accordingly).

And now, a note from my conscience:

I had to think long and hard about why I’m doing these challenges the way I am. When you’re asking for speaking gigs or people’s time who have more power and influence than you, there’s a tendency to come off as disingenuous and ‘clout-chasey’. So how do you avoid falling into that category? Self-awareness. At least, I think so. I’ve gotten very clear about my mission, vision, and why in the past few months, and am going about things in a deliberate way that will create an impact in this world.

But another part of me can’t help but feel this is really my daakshan talking. Didn’t everyone who ever achieved anything big have to start somewhere and do uncomfortable things? That is, after all, the entire point of this exercise! If it doesn’t give you the heebie-geebies, you’re doing it wrong.

So what are your thoughts? And what do you think I should attempt next?

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