Greetings from not-so-sunny Bristol, UK! ☁️

I'm overseas from my usual hangs in NYC writing this from either the train, the pub down from where I'm staying, or the coffeeshop in Old Towne Bristol, depending on what part of the edits you're currently reading.

I came to the UK after spending a week at the most magnificent How to Web conference in Bucharest, Romania. The conference, started by Bogdan Iordache, features builders, innovators, founders, and investors all around the globe, all focused on building internet-based products and tools.

I met with founders and startups chasing all sorts of wild ideas. I served as a mentor on the community products circuit, giving a talk and networking with founders with bright ideas at various stages of company life or funding.

Initially β€” I came to give a talk on proactive community moderation, but I left with more than just having done that β€” I also explored a glorious part of the world and made a bunch of new friends. Comrades and collaborators who all understood the value of the web and how it can help us collaborate.

By no means was this my first talk I've given, but it was one of the talks I'm most proud of having given.

This talk stood out for a few different reasons:

  1. First IRL international talk under my belt! πŸŽ‰
  2. I received great feedback from the conference organizers and attendees of my talk.
  3. My talk was described as a "fun, insightful look in the world of online community." Β (Yes, I immediately added that Twitter DM I received after my talk to the 'wins' folder).
  4. I rickrolled the audience in the name of education. πŸ˜‰

Now, I'm all for fun, games, and a laugh or two β€” I am, after all, a standup comedian by night. But sometimes, we sacrifice learning and insights when we lean into fun and games.

I struggled earlier on in my career to find the right balance between "fun" and "educational" and ended up more like a bad take of the One Semester of Spanish Lovesong.

I'm shrugging on a stage in front of Rick Astley's music video "Never Gonna Give You Up." I'm wearing black wide legged cropped jeans, blue blazer and a white tank top.

Here are some tips I've learned to effectively marry the content divide between fun and functional in the content arena.

Understand the point you want to make β€” how does your commentary move the narrative of that point forward?

If you have to "force" the plot forward because you're making a joke β€” it's not worth it. Your audience will be confused and struggle to draw a connection. Remember, your audience doesn't know the topic as much as you do; you're the expert in the room. Make it easy for them to understand what they should take away from this conversation.

We all hate it when things feel like they're not moving along β€”Β don't do that to your audience, either.


Know the stage you're on.

Different stages have different tolerance levels for comedy. Given I was at a very online, very tech-savvy audience, I understood internet humor would perform well. This was a primarily international audience. English Many folks spoke English as a second language. Satire, sarcasm, or other points of humor may not have landed as well as the rickroll because of the amount of nuance, context clues, and other subtleties that were to take shape. This doesn't mean it wouldn't be possible, but is it fun to make your audience work to understand your humor? Keep it simple.

Not all stages are for your type of vibe... take Abigail Breslin's dance in one of my all-time favorite movies, "Little Miss Sunshine."


Tie it together.

IMHO, nothing is worse than when you read a book and an author gets overly carried away in a side tangent or plot detour that doesn't matter or add value. Sure the joke could offer terrific prose and descriptive powers β€” but it also could open up confusion and frustration if not done well. How can you tie your humor or jokes into other parts of your talk?

In my case, I could connect the dots to show how the glorious Rick Astley has become a more harmless form of internet trolling on the larger spectrum of all internet trolls.

Trolling β€”Β ahem β€” teaching in style.


If you're not having fun, neither is your audience.

At the end of the day, if you're not having fun, neither is your audience. Take the stage with purpose and for a reason; entertain, delight, and inform with your words, mannerisms, and habits. Your audience came to see you and the content you're delivering. In the words of John Mulaney, canceling plans is as addictive as heroin. If you're fortunate to be a plan that someone isn't planning on canceling, make it worth their while. πŸ˜‰

sorry dude, fun is kinda *my thing*


How do you have fun in what you do?

What are your tips for having fun and incorporating humor in the talks or educational content you create? How do you surprise and delight your audience on a stage or video screen?

Let me know! I'm always looking to level up my repertoire!

πŸ„πŸΌβ€β™€οΈ Catch you online.


🧠 Things on my mind this week

Content I consumed


  • Office Hours with Abby!
    Mondays by appointment β€”Β RSVP here.
    The person I go to for all my "WTF DO I DO" work questions is now opening it up to the world (and she's damn good at it, too, so take her up on this!). Abby T. Miller is a coach and consultant helping startups and their people navigate growth and change confidently and even calmly. (Yes, it’s possible!) This happens every Monday, book time here, or follow Abby on LinkedIn.
  • Building a Newsletter Community with Clayton Chambers
    Wednesday, Oct 5, 2022 β€”Β 9 AM PT / 12 PM ET / 4 PM GMT β€”Β RSVP
    ​Join me as I chat with Clayton Chambers, founder of Sprezza as he chats about how he built the community behind his newsletter, what's next and learning curves along the way.

    We'll also break down and build in public some of Clayton's next project β€” a curated database of top independent brands.
  • Running Developer Communities with Discord (Workshop)
    Thurs, Oct 13, 2022 β€” 10-12 PST / 1-3 PM ET / 5-7 PM GMT β€” RSVP
    Whether you are considering Discord for your community or already running a Discord community and want to get more out of the tool, this workshop will provide you with the tips and insights you need. Join the team and me as I walk you through using Discord to manage developer and technical communities.
    Sponsored by Common Room.