Pantheon Community

WebOps Wednesday AMA: Brian Richards

Hi! My name is Brian Richards and I am the creator of WPSessions and lead organizer behind both WordSesh and WooSesh.

I’ve been developing for the web since 1998 (anyone remember Tripod hosting?) and using WordPress since 2007. I’ve worked as an independent contractor, in-house developer, and worked my way up the agency ladder to Director of Development, eventually managing a team of 20+ incredibly skilled people while working on projects for the Fortune 100 and beyond.

I launched WPSessions in 2013 so I could pay people smarter than me to fill my business and development blindspots. Seven years later, the site now hosts more than 170 hours of exclusive training content. There are a lot of great lessons to be learned here!

These past few years I’ve specialized in tutorial videos, private team training and onboarding materials, and online event organizing. My real passion is for self-directed learning and helping others to better solve important and complicated problems. I can’t resist helping good people do great things!

Conversation notes (the things I feel qualified to discuss):

  • Public Speaking, Training, and Event Organization
    • I’ve personally attended all 170+ hours of presentations on WPSessions and can offer plenty of advice on creating, delivering, and pitching a compelling presentation.
    • I’ve found a lot of success and opportunity from public speaking.
    • I can talk in-depth about creating both tutorial and promo videos.
    • I also have a ton of experience to share organizing and hosting both physical and virtual events (from meetups and conferences to webinars and summits).
  • Development and Design:
    • I’ve been working with WordPress since version 2.3, designing and developing custom sites, plugins, themes, and admin experiences.
    • I’ve worked both independently and with several agencies (both internally and as a contractor or consultant).
    • I run a mixture of custom code and commercial plugins for running both WPSessions and the 'Sesh events. I have a lot of opinions around when to pick a library vs build a custom solution.
    • Before going all-in on development I spent a lot of time learning graphic design. To this day I still design most of my own sites and artwork.
  • Personal Finance:
    • As best I can, I try to operate my business by maximizing runway (that is to say, future salary in the bank). I currently have the next 6 months worth of payroll stashed and invoices due for another 6 months beyond that.
    • We optimized our family budget early on to eliminate all our debt, keeping away from everything except mortgages ever since.
    • Our current family budget is optimized for experiences (things we can enjoy together) and various long-term savings goals (trips, home renovation, etc.)
    • Our long-term investment strategy is in rental property.
  • Personal Interests:
    • I have a degree in photography and can talk cameras, lighting, and composition for days.
    • I’m a super amateur woodworker, but I talk a big game. I have plenty of free opinions on tools.
    • I love high-quality action and sci-fi movies. Anything with a believable plot, characters who are congruent for the entire story, good dialogue, and great cinematography.
    • I’m a huge fan of Lego and have a collection that dates back 30 years.
    • True story: our house was robbed once, while we were sleeping, and only our Lego was stolen. I now have a LOT of experience with filing and completing an insurance claim.

Hi, Brian! Thanks for hosting this week!

I’ll start with this question: What do you recommend for newly-virtual conferences as far as the socializing aspect goes? My favorite part of a conference is often who I meet while I’m there and I know a lot of organizers are struggling with that part of the event going online.

And: I’d love some high-quality action/scifi movie recommendations!

Starting with the most difficult question right out of the gate!

The networking component of a physical event is hard to replicate in a virtual event. There is SO MUCH that we can do in physical spaces to foster conversation and community engagement that are difficult or impossible to do virtually.

For instance, let’s look at the highly coveted “hallway track.” This works because people can move about freely, joining and leaving conversations as they see fit. Seeking out people they know they wish to meet, or serendipitously encountering people they wouldn’t have otherwise met.

The best long-term experience I’ve had for virtual events to date has been a companion chat via Slack (or Discord) with guided conversation and targeted channels (e.g. based on topical interests or location).

I’ve seen some groups experiment with “Birds of a Feather” zoom rooms to varying degrees of success. The most crucial piece for success in these is advertising them ahead of time and providing quality moderation.


Hey Brian! Thanks for being available for questions today.

I help out with our Drupal User Group meetup, and one of the things that we struggle with is enticing new attendees. We have a pretty solid group of 5-8 attendees each month, but we’d love to see that grow and help get new people involved and speaking on new topics. Do you have any tips , tricks or advice for growing a user group?

In non-pandemic times, we usually have a physical location we meet at with a way to tie the meeting space into a zoom room so that we can have remote attendees as well. Right now, we’ve obviously shifted to fully digital.

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Hi @rzen! I heard that you’re in the market for a new bicycle. :biking_man: What do you currently do and what are you planning to do once you have a new bike? Are the kids getting into it, too? :kick_scooter:

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For movie recommendations, here are a few recent(ish) releases that I enjoyed a lot:


  • The Accountant
  • John Wick 1 & 2
  • The Equalizer
  • Mission: Impossible Fallout
  • Kingsman
  • American Made
  • Jack Reacher
  • Baby Driver
  • 1917
  • The Hitman’s Bodyguard


  • Ready Player One
  • Blade Runner 2048
  • The Martian
  • Arrival
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I currently ride a decades-old mountain bike on permanent loan from my brother-in-law (it’s been in my possession for at least one of those decades). It’s done a fine job, but it is quite cumbersome.

Our two oldest kiddos (currently 7 and 5) have been getting into riding their own bikes recently. Our youngest (nearly 2) really enjoys strapping into a stroller for walks, and mostly enjoyed his single outing in our bike trailer.

I’m looking to do more casual riding with something modern and a bit more light-weight than a mountain bike. We have plenty of pavement to ride on here (plenty of neighborhoods, parks, and paved trails) I have lofty aspirations of getting out for a ride several times per week for some good physical exercise throughout the spring and summer months. We’ll see how I do!

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In my experience, more people attend an event when 1) they know somebody and 2) they’re personally invited. My first recommendation is that you encourage the 5-8 regular attendees to each personally invite someone to the next meeting (including people who have attended in the past but haven’t been to a recent event).

Following that, I have a few different ideas that might show varying degrees of success:

  • Invite well-known and compelling presenters to share with your group. Make sure to advertise this event through all the regular channels (mailing list, social accounts, etc).
  • Host a “show and tell” event and encourage each attendee to bring something neat either from their own portfolio or that they found across the web. Stress that they don’t need to spend more than 3-5 minutes sharing.
  • Host a “bring your problems” or “ask the experts” event and encourage attendees to submit some of their challenges ahead of time. Make sure you tap a few group members to help moderate and answer questions ahead of time. This typically works best in a physical event where you can spread out and address some questions 1:1.
  • Host a “meetup reboot” event where you invite people to come and suggest a topic they would like to see covered in the coming months. When we kicked off a local meetup we gave each attendee three post-it notes to write whatever three topics they wanted to hear most. Then we stuck them on the wall and clustered them around similar topics. The topics with the most stickies were what we used to priority order the topics for the next several months. You’ll have to get a bit more creative to do this one virtually.
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With so much employment upheaval happening in the US right now, a lot of people are looking at the future of their career differently than they would have 2 months ago. I’d love to hear more about building a consulting portfolio or any tips you have as a former development director for interviews/hiring.

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Given that I like all of the films on here that I have seen, this looks great. Thank you!

The parallel Slack/Discord makes a lot of sense – and I like the Birds of a Feather zoom rooms idea too! Thank you for the thoughts on that.

I was heads-down coding/designing yesterday, so I missed this AMA. I do want to ask, if you’re still available to answer, what the prospects of success are in the WordPress and general website marketing tutorials arena. I’ve been wanting to do this to build my personal brand and share my expertise as an online business coach, but everywhere I look there are people like me and it seems even more difficult of a market to differentiate in than owning a digital agency is. Am I too late to that party or is there still a niche to be filled?

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It is definitely not too late! WPSessions was not the first site to compile WordPress training, and there have been many others since.

There will always be new people looking to learn a topic, and they will seek out voices (instructors) they like. Yours could be the 100th tutorial/explainer on a given topic, and it will find an entirely new audience than the previous 99. Or it may find the same audience and resonate with them differently.

You have a unique perspective, a collection of experiences unlike anyone else. Teach what you know, in the topics you want to be known for, and hold nothing back.