Welp. I failed.

When I launched Drunk Business Advice 129 weeks ago, I envisioned a very different outcome.

I’m an entrepreneur, so I wanted this newsletter to anchor a media business. I wanted it to… ya know… make money.

And given that I had no experience building a media business from scratch, I threw myself into that world. I befriended all the heavy-hitters. Attended all the conferences. Joined all the masterminds. Spent hundreds of hours and thousands of dollars educating myself.

And if you’ve been with me for a while now, you’ve witnessed me launch a whole flamin’ heap of media products:

But nothing really quite… landed. Which is an ego-saving way of saying they failed.

So what’s next for me?

👉 Some investments have extraordinarily unexpected returns.

And now — the story behind why this advice matters. 👇

If you love this newsletter, which I sincerely hope you do, I’ve got good news for you:

I’m not going to stop.

This might seem crazy to some. Y’all know that I spend 8+ hours crafting most issues of Drunk Business Advice. So that’s over 1,000 hours spent so far on just writing the damn thing. And I’ve published 190,000 words over 129 weeks.

—hold for applause—

I never use AI to write this shit — every word (and yes, every em dash) is 100% USDA Certified Grade-A Kristin.

That’s an absurd amount of time to dedicate to a project that I’m no longer trying to monetize. But I’m not continuing this effort as some sort of masochistic activity, or because my heart is so angelically pure that I just want to give and give without expecting anything in return. 

No. There are two very practical reasons I plan to continue publishing Drunk Business Advice every week:

And if you don’t start putting your original ideas out into the world after reading what I’m about to tell you, I haven’t done my job.

Over the last 129 weeks, I’ve been saying “no” to a shit-ton of opportunities.

Why? Because I was busy building my media empire, of course.

I had decided that I no longer wanted to be the kind of entrepreneur with clients. I wanted to be the kind of entrepreneur with customers. Since I have no interest in building software (and SaaS is dying a painful death), a media business felt perfect for me. 

And I had already been trained by the best in the biz during my brief stint at The Hustle:

One thing that I learned is that you can’t half-ass a media business.

There is a treacherous ocean of gurus out there who will try to convince you that a sustainable media business can be built as a “side hustle”. Just spend a few hours on it every week, and watch it print money.

HA! Utter bullshit.

Because aside from creating insanely good content every week, you also have to relentlessly earn subscribers, build offers, sell those offers, oh shit that offer didn’t land with my subscribers, but some of them bought so I still have to deliver that product, wait who actually are my subscribers, let’s spend 100 hours building out a different offer, oh no the top of my funnel is dwindling, gotta estimate how much I can spend on acquisition, but wait I don’t have a monetization engine yet, let’s test more offers, oh I’ll find a sponsor to pay for marketing, but if I have a sponsor where can I place my own offers in the newsletter without interfering with their results, did I remember to post on LinkedIn this week, shit it’s Saturday afternoon and I haven’t written Sunday’s issue yet.

So picture me in the middle of all that when some fantastic reader reaches out to me. They love what I do, and want to find a way to work together.

My response? “No! I don’t want clients. I want customers. And I’m absolutely killing myself to build this business, so I don’t have time for anything else.”

As idiotic as it may sound to decline opportunities because I’m too busy creating opportunities, I stand by that decision. I had to see this thing through to the bitter end.

But while I was busy building a business, I didn’t realize that I was also building an asset. A reputational repository. A pipeline of potential.

So a few months ago, after two years of workin’ my hiney to the bone, I stopped trying to create a business out of this scrappy little newsletter… and just started saying “yes”.

Now I’m working on some dynamite projects, with some dynamite people — none of which would have been possible without Drunk Business Advice. 

But even if there was no personal brand equity to be gained, no business opportunities to be seized by writing this newsletter, I would still do it.

There’s a great quote that’s often misattributed to Abraham Lincoln, but it’s worth repeating:

“In the end, it’s not the years in your life that count; it’s the life in your years.”

I can think of no other initiative I’ve undertaken which has added more life to my years than shamelessly deploying my original thoughts into the world. (Try it. It’s hella fun.)

And I’ve identified three reasons why this is a universally good thing:

Most of my friends are curious, but their curiosities get bashed to bits by the overlords of productivity. 

Think about it.

Something catches our attention… we wonder about it for a moment… we might Google it, or mention it over dinner, or add a book about it to the reading list we know we’ll never get through…

But then life gets in the way. Unless there’s an apparent payoff for wandering down a rabbit hole, those little intellectual sparks tend to disappear beneath more pressing responsibilities. Adulthood treats curiosity like an indulgence. Which is such a shitty predicament, because curiosity is the primary mechanism through which people develop original thinking.

But what if exploring your curiosities had a legitimate claim over your time? Because, ya know, you have thousands of readers who expect you to deliver a badass essay every Sunday?

Suddenly, a question about a suspicious business model, or an obscure piece of history, or some oddity of human behavior, is all worth investigating.

Frankly, it’s a beautiful way to live.

I bet you have opinions. I also bet those opinions have never been subjected to much scrutiny.

And I don’t necessarily mean scrutiny from other people — scrutiny from yourself.

Before you hit “publish” on a piece of writing any longer than a tweet, you better be shredding the hell out of your own ideas. You better be interrogating yourself. You can’t just declare what you believe about business, leadership, judgment, human behavior, whatever… without also explaining why.

Because if you don’t do it first… they will. (And they are ruthless.)

This exercise sharpens your judgment. It takes a basket of disjointed opinions and molds it into a cohesive point of view. It forces you to expose the reasoning behind your conclusions, and creates a record of that reasoning.

And it also reveals that the ideas we carry around in our heads are considerably less coherent than they seem. (Or at least it did for me. 😬)

One of the biggest reasons readers return to Drunk Business Advice week after week is the crazy f*cking stories that come to life on these pages.

And let’s be honest — we all have crazy f*cking stories.

But the art of sharing those stories with others requires you to revisit them in a different way.

For instance, if you’re journaling about your experiences you can write about what happened, how you felt, and what you think it meant. But when you’re writing about your experiences for others, you have an obligation to deliver value.

So how do you find that value?

You examine your experiences. You figure out what they actually taught you. You move beyond remembering an experience to extracting something transferable from it.

And that transferable thing has a name: wisdom. 

I know it sounds like I’m overselling the value of this. But I swear to you, I’m being completely genuine when I say that the compounding effect of exploring my curiosities, honing my ideas, and telling my stories has incalculably improved my life.

So yeah.

I’m going to keep writing Drunk Business Advice. And I hope that you’ll keep enjoying Drunk Business Advice.

Here’s one small request:

If you’ve never responded to one of my emails, and you’ve reached the end of the newsletter, please hit reply and introduce yourself. I’ve met many riveting readers, and it’s been the greatest delight. But there are so many of you that I haven’t met yet. I’d love to learn more about you.

Signing off on this week’s 1,633 words. 😮‍💨

Cheers! 🍻

-Kristin :-)

P.S. — I don’t just write Drunk Business Advice — I bring it to life on stage. And I’d love to speak at your next event. Hit reply or click here to learn more.