The moment this email arrived in your inbox today, I was on stage at the Times Square Hilton telling a room full of startup founders the story of how I f*cked up the launch…

…of this very newsletter.

I know.

Very meta.

So I thought today would be a good time to tell y’all about that.

F*ck-up #1

Drunk Business Advice started as a podcast.

The reason I liked the idea of a podcast is because I wanted to have unfiltered conversations with badass business leaders about the un-sexy stories behind their success.

And I still think it’s a solid concept.

But—

It was a horrible idea. 🤦

Why?

A few reasons…

❌ I know nothing about podcasting. I don’t even listen to podcasts.

❌ I suck at marketing, and you have to be a killer marketer to achieve any remotely meaningful traction with a podcast. 

❌ Podcasting is a broadcast medium. You don’t “own” your audience, and it’s hugely difficult to create a conversation with them, which means you can’t collect early feedback and iterate.

I recorded four episodes (with four brilliant guests), and had three other interviews lined up, when I realized that my plan was deeply flawed.

The conversations were killer, but I simply wasn’t qualified to cold-launch a podcast.

None of the episodes were ever published, and I went back to the drawing board to begin crafting a plan to launch Drunk Business Advice as a newsletter.

I thought I was soooo smart

In my second attempt to launch Drunk Business Advice (this time, as a newsletter instead of a podcast), I did two very smart things that most solo-operators neglect:

1. I got myself an accountability partner

2. And I committed to a deadline

And not only did I do those things — I f*cking nailed them.

👉 The first smart thing I did was get the BEST accountability partner imaginable. 

Rob Capili is probably the most badass person I know. He’s an accomplished entrepreneur, software engineer, filmmaker, writer, salsa dancer, and even has a black belt in Jiu Jitsu.

He had the perfect blend of skills to provide me with constructive creative feedback, while also keeping me on track with my deadlines, business goals, and tech stack.

I cannot stress this enough — surrounding yourself with talented people who care about your goals as much as you do is the universal cheat-code to life.

And without Rob, I would have been as productive as a dizzy squirrel.

👉 The second smart thing I did was tie my launch date to a major industry conference.

Not only did this make my launch date rigid (although Rob probably would have bashed my head into a wall if I had tried to move it anyway), the conference itself was an opportunity to nail down some partnerships and generate some PR buzz—

Which are both important for gaining early traction when you’re launching a media product without an existing audience (or heaps of cash to throw into advertising).

My plan was to approach major publishers at this conference who had similar audiences to the one I was trying to build for Drunk Business Advice, and offer to perform free editorial work for them in exchange for a plug for my newsletter.

You can pat me on the back. It was a great plan.

I had even purchased a premium ticket to this conference so that I would be sure to have the opportunity to connect with the people I wanted to partner with.

Which leads us to…

F*ck-up #2

I stuck to my deadlines, and published my first issue of Drunk Business Advice on April 25 — one week before the conference.

The evening before the conference, there was a cocktail party and dinner for premium ticket-holders. So I hopped on a call with Rob that afternoon for a pep talk.

He asked me about my goals for the evening, and I told him who I was planning to try to chat with that night, and what I hoped to achieve through those conversations.

Then he asked me a question that made me immediately uncomfortable:

“So – what are you planning to actually say?”

Um. I dunno. I was just planning to tell them about my cool new newsletter, and try to get them to let me write some editorial for their publications.

Y’all — Rob already has “resting bitch face”, so when he’s truly annoyed, his “frustrated look” could melt steel.

He repeated:

“Ok, but what words are you actually going to use? Pretend I’m one of the publishers you want to meet. We’ve just bumped into each other at the cocktail party. Go.”

Shit shit shit shit shit shit shit.

Rob to the rescue

After uncovering the fact that I was utterly unprepared to talk about the amazing newsletter I had just launched, Rob dipped into his expansive skill set to help me out.

He told me about a technique he had used for pitching screenplays.

It’s sort of like an elevator pitch, but an elevator pitch has a major flaw—

After you’ve delivered it, if your conversation partner is interested in hearing more, one of two things happens:

1. You freeze up, and don’t know what to say next.

2. Or you word-vomit jargon all over the person, digging up every detail imaginable, until they’re bolting away from you.

Neither of these things underpin an enjoyable party conversation.

But with Rob’s screenplay pitch technique, you strategically reveal a little bit at a time, looking for positive signals from the other person that they’re interested in hearing more.

Ya know — like an actual conversation.

This makes so much sense for Hollywood, where (I imagine) far more business interactions take place at parties and events than “formal” meetings where you’d be pitching your screenplay in an office. 

Here’s how it works:

And so on…

I wish I could tell you that in the couple of short hours I had between learning about this technique, and attending the event, I was able to carefully craft the casual and concise sentences you see above.

Um. No.

I’m reminded of the Mark Twain quote:

“I didn't have time to write a short letter, so I wrote a long one instead."

Mastering conciseness takes a shit-ton of effort.

But even though my words weren’t as concise and curiosity-inducing as I would have liked them to be, my last-minute pep talk with Rob did remind me to do something very important that night.

👉 Speak a little bit, then shut up.

And at least that made me likable, which eventually led to some fantastic opportunities.

It blows my mind

When you stop to think about it, it’s incredible how few people are truly prepared to discuss what they’re working on in a social setting.

If we’re invited to “pitch” somewhere, we:

• Agonize over every slide in our deck

• Write and re-write and re-write our script

• And rehearse like crazy

But, in the same way that Hollywood business gets done at parties and premiers, pretty much every other kind of business gets done at conferences and networking events.

And those conversational opportunities are dramatically more numerous than “formal” pitch opportunities.

So why aren’t founders and business leaders prepared for them?

I began putting together a structure for how entrepreneurs can craft a “conversation pitch”, and introduced it at some workshops I was invited to facilitate last year.

It went pretty damn well.

Then I added it to the curriculum for Rebel Scribes.

And now, I’ve crafted a short e-course, so everyone else can master this technique, too.

(At the very least, everyone collectively getting better at conversations will make events far more enjoyable.)

I’m excited to launch the e-course on March 10th, and y’all will get it for $49  $29 if you pre-order before then with coupon code: DRUNK

That’s my pitch. 😉

Cheers! 🍻

-Kristin :-)

Tell me what you think of Drunk Business Advice.