GOOD AFTERNOON! It’s been an all caps kinda day at Smooth—today marks our second birthday. 🥹 It also happens to mark our CEO Josh’s birthday (no, we don’t know what compelled him to launch a company back on his 26th birthday, maybe something to do with health insurance?).

To celebrate, we’re sharing a random assortment of 10 lessons, ideas, learnings, and observations we’ve collected over the last two years. Let’s party!

—Kinsey, cofounder and head of editorial & Jenny, cofounder and COO

10 Kinda Random Learnings & Observations, 2 Years into Smooth

1. We can’t be afraid to make a change. Pivoting? That’s show biz, baby. We’ve done it, it’s worked, and we’re committed to staying nimble because of that experience. Your thesis can stay the same even as the strategy you use to act on it can change.

2. Our most sophisticated POVs are the ones we can write out. To offer critical feedback or the dreaded “my two cents” verbally is easy—anyone who got north of a 500 on the SAT Writing & Language section can sound smart if they use big words.

But articulating your thoughts in written word requires much more. You’re forced to question your own line of thinking and crystallize your points into something that makes sense. And for the teammates you’re sending it to—being able to read your work allows them to take it in slowly, ruminate, and ask insightful questions that foster a productive conversation.

Always. Write. It. Out.

3. Give things fun names. Because it’s fun, but also because it’s effective.

• Our company value to always share information with the broader team to break down silos → #Overcomms.

• Our quarterly full company in-person week → SQIRL (Smooth Quarterly IRL).

• Our sales channel Slack bot that automatically goes off when an IO gets signed → #yaeshbot (Colin will have to explain that one to you).

• Our Notion database for all our revenue campaigns → The Revenue Canoe. 🛶

Imagine saying the former instead of the latter in each of those?? Sounds brutal.

4. Taking a moment to learn and reflect is and should always be in our DNA. We do it weekly during our Monday full-squad sync in what we call Learnings & Observations™ (hey we’re even L&Oing here too). Everyone shares, everyone discusses, we all get better.

5. We’ve learned when to, proverbially speaking, dress for the job we want. There are times we have to act like a scrappy, bootstrapped startup and times we have to act like the company we want to become. Differentiating between the two has been a big unlock.

6. Startup company culture has no obvious best practices. There’s the crystal clear stuff about fostering earnest company culture—don’t say “we’re all a family here,” don’t make people work the Monday before a Tuesday Fourth of July, etc.—but when it comes to the personality and the flair of a growing company, do what feels authentic to you and your early team.

We love a good Slack voice memo, posing in-depth hypothetical questions, creating our own terms (see above). It makes work fun, and it makes it ours.

Because getting shit done is even more gratifying when you can have fun doing it.

7. Play your game and worry about your team (also sports metaphors >>>). Focusing on what only we can do uniquely for our partners is our primary goal. We’ve learned what we’re best at, and that’s helped us keep the blinders on when we get those “have you seen this company” Twitter DMs.

8. We have to keep our cofounder friends (cofrienders?) honest. The three of us (Josh, Jenny, yours truly) were close friends before we were cofounders.

There's inevitable emotion and disagreement that come with running a startup, and we've had to be diligent about how we manage our personal relationships and working relationships with one another.

While we can't say we have all the answers, a few quick tactics that have worked for us: direct questions, biweekly cofounder check-ins that start with the intentionally open-ended "how are we feeling," and opting for a phone call vs. endless Slacks when things get hairy.

9. Be an owner. Take accountability. It's easy to take credit and feel proud when something goes right. Not to say you shouldn’t, but it’s not hard. When something goes wrong—a partner, project, new hire, or strategic decision doesn’t work out—our egos can tempt us to avoid addressing it head on and instead place blame on conditions out of our control.

We’ve made countless mistakes the past two years. What we like to believe we’ve done and will continue to do is fully acknowledge and own them—speak about them, unpack them, and learn from them. Say we f*cked up. Explain what we thought when we made this choice, why we were wrong, and how this experience will inform our decision-making going forward.

In short: Make mistakes, but put your ego to the side and take ownership when you do. Learn from them and don’t make the same one twice.

10. We’re confident in what makes us us. While seeking advice and talking to peers/mentors is great, we can’t and shouldn’t implement every last piece of advice we hear. Blanket feedback won’t always apply to us. Even from the smartest and most trusted of sources. Some things we have to be headstrong on—knowing what those few things are is knowing what makes us Smooth.

Bottom line: These 10 L&Os are a small sampling of what we consider to be a very, very strong foundation for the future here at Smooth. We’re curious to hear what you think. Hit reply and let us know your Ls, Os, and feedback.

Media news had major “Lemon it’s Wednesday” vibes this week. If you don’t get that reference please Google it.

• Kinsey’s favorite deal of the week: Alex Cooper’s new Unwell Media signs Alix Earle and Madeline Argy in development deals. Is this the defibrillator podcasts need to appeal to Gen Z?

• TikTok will let creators link their videos to full-length podcast episodes via RSS feeds. Could be significant in curing the headache of getting short-form views → podcast downloads.

• Betches is killing it: revenue has grown 40% every year since 2020, it’s been profitable since it started in 2011, and unlike many of its digital media peers founded around that time, it’s still alive and kicking.

• Puck has raised over $10 million in a Series B growth round.

• Fun read: “The biggest names in food are just regular people on TikTok,” from Vox.

• Dave Portnoy has bought back Barstool Sports from Penn in what truly feels like a bonkers deal.

#digibuzzcodevoxious is a term we coined back in our Morning Brew days—a portmanteau of Digiday, BuzzFeed, Recode, Vox, and Axios. Obviously, the year was 2018 and the interest rates were zero. But still, the sentiment of “interesting media trends and news” remains. So the name stays.

To celebrate Josh’s birthday, I’d like to share the three photos he took as my guest at WeWork last week, all of which landed in my inbox as jumpscares. Here’s to another year, Josh!

Thanks for reading, everyone! Make today count because August will eventually slip away like a bottle of wine.