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Adventures in Businessing: Entrepreneurship, Small Business, and a Healthy Dose of Humor

by Ciircles

Adventures in Businessing (AIB) is a podcast where four entrepreneurs in 3 different industries discuss all the challenges that come with creating. It's a whilwind of insight, discovery, and absurdity as these 4 take you on a new adventure on a different business topic each week.

Episodes

Helping Your Team Navigate Change

30m · Published 24 Sep 11:00

Show Notes:

[0:00:00] Intro | Timely Topics
- The Uncertain Edition?
- Recap on Uncertainty to Action & Unknown-unknowns
[0:02:30] How Do You Lead & Navigate Through Change?
- Acknowledging the different types and areas of uncertainty in your business:
  - 1) The uncertainty you may feel as an owner/manager.
  - 2) The uncertainty that your team might feel from lack of clarity and/or communication.
    - "How do you handle the uncertainty you feel, and how much of that do you share with the team?"
    - "How do you ensure the team has the clarity they need?"
- Living with chronic uncertainty can negatively impact anyone, literally rewiring our brains.
  - This kind of stress will change the way a person thinks.
  - When you convey your own uncertainty, you have to prevent simply piling on and multiplying fear.
- Transparency is always something to aim for, but some uncertainty is better held amongst the leadership.
  - But this is usually a very small list of things.
  - Assume the best from all parties involved.
  - Transparency regarding uncertainty is always a balance.
- Maybe don't impulsively share uncertainty.
  - Ruminate and consider it the unknown before sharing.
  - Your team will see how leadership responds to uncertainty and typically emulate that.
[0:09:06] You want an organization and culture where others can voice their uncertainty without repercussion or criticism.
- Even as a leader, you may think you see everything...but you don't.
  - Ensure your culture is an open one.
  - Survey your team to determine where their uncertainties are.
    - Ask the question.
- Adoption of change looks different for everyone.
- Don't underestimate the impact of change on your team.
  - "People don't struggle with the change, they struggle with the transition."
    - "With all transition, there has to be a time to mourn the loss. That's what people struggle with."
    - "Organizations don't always give the appropriate time for our teams to mourn and truly transition, that's why people fear change."
    - "You as a leader have often had the time to process, whereas your team is just hit with one thing after the other in a transition."
  - Listen to the feedback for uncertainty that you may have created in announcing change or transition.
    - Always do your best to address the why.
    - Allow your team to have input in how their day-to-day may change.
      - When we have input, we're more likely to be okay and internalize it.
  - See the change from your team's perspective.
    - Intentional empathy can work wonders for your organization.
- Have your culture and values in place ahead of change and any transition.
- Involve the team in solutioning.
  - It makes change so much smoother and easier in the long run.
[0:19:54] Presenting Change
- Consider presenting change as "here are my thoughts and suggestions, think about it, and let's discuss in a few days to a week".
  - Offer your input as flexible ideas that the team can influence and even improve upon.
  - It's a lot easier to accept something that may be possible, but not necessarily a last-minute directive or mandate.
- Lead the conversation with the uncertainty and challenge so that everyone is immediately looking to confront this as a team.
- Time-box your idea and solution/s.
  - Experiment.
    - Nobody mourns the loss of an experiment.
    - You have to follow through and weigh the results of the experiment.
    - Failed experiments are their own successes if we learned something.
- Ultimately you're trying to build resilience.
  - You want a culture that is versed in experiments and can bounce back from failures with positive lessons and takeaways.
[0:27:37] Parting Words
- "Business is change, there is nothing else."
  - Whether we like it or not.
  - Figuring out how best to change, and how to roll with the punches is vital.
  - Remember, how you transition through change is what matters.
  - Experiment, iterate, and move forward.
  - You're either helping your team become more resilient, or more brittle.

Moving from Uncertainty to Action

30m · Published 17 Sep 11:00

Show Notes:

[0:00:57] Intro | Timely Topics
- Radio voices are a go.
- Wear sunscreen!
- A brief recap of the previous episode.
[00:03:00] Leaving Behind Analysis Paralysis
- Punished by choice, leaving uncertainty to chance, and overconfidence
  - All of them exhibit a lack of knowledge/experience/data.
- Gaining information when under the thumb of uncertainty.
  - Iterative action/s through uncertainty.
    - Understanding pieces at a time.
- "Put one foot in front of the other...and soon..."
  - You can't overestimate the value of action.
- The scientific method is your friend!
  - You make observations and you ask questions. That's the start.
    - "What does this uncertainty/opportunity afford to us as a company?"
    - "Then what?" *what's next?*
    - "So what?" *measuring worth & magnitude*
[00:12:20] Important Aspects of Moving from Uncertainty to Action
- "Where is the opportunity in the uncertainty?"
  - Using the trend of distributed work culture as an example.
- Forming a testable explanation to get you to the next stage.
- "What are the limiters to growth?"
- "What are the things that good organizations do continually?"
- Financial capability can undoubtedly fuel growth, but ultimately people (and their experience/talent) are the finite resource that limits growth.
- You HAVE to make a prediction.
  - You want to come out of your experiment with more knowledge than you had going into the hypothesis.
  - Informing the prediction.
    - Expected outcomes vs the reality.
- Control your variables...as best as you can.
  - An example using seasonal discounts/sales.
  - Isolate individual actions.
- Results HAVE to be repeatable.
  - Because you will have to repeat your results, likely sooner than later.
- Moving from one experiment to another too quickly is dangerous.
  - One at a time is best if possible.
- Iterate, and repeat the processes.
  - Insert new variables, new predictions.
- Patience is so very important.
  - We often give up on things too quickly.
    - Stop it.
[00:24:50] Wrapping Up with Parting Words & Takeaways
- Things to keep in mind:
  - A failed experiment: a hypothesis PROVEN WRONG is a SUCCESS as long as you learned a lesson!
  - Everything moves you toward success.
  - To quote Adam Savage of Mythbusters, "Failure is always an option."
    - The truth is that failure doesn't have to be negative.
  - When you're dealing with uncertainty, decisions are riskier than experiments.
    - It's ok to be uncertain, but it's also ok to be certain...as long as you're right.
      - This is why it's a lot safer to admit when you're uncertain and create experiments than it is to double down on your pride/ego with decisions that come from false certainty.
      - Commitments are dangerous in experiments.
  - Action is okay, but experimental action is the best way forward.

Identifying & Understanding Uncertainty

29m · Published 10 Sep 11:00

Show Notes:

[0:00:49] Intro | Timely Topics
- We’re all surrounded by uncertainty in these trying times.
- Dealing with uncertainty in your business & your life
- How we respond to universal uncertainty is unique to each of us.
[0:05:25] Identifying Uncertainty in Your Business
- We wrongfully attribute uncertainty to risk.
- We often lack the information to reasonably define uncertainty as risk.
- Using Slack as an example.
- Certain people are excited by uncertanty.
- It’s very important to be able to react to the unknown things that pop up.
- You can address some uncertainty simply by not being too certain of your plans.
- Keep an eye and ear attuned to your marketplace.

[0:13:50] Everyone Handles Uncertainty Differently, and That’s Okay
- Uncertainty may entice, excite, and compel some to action.
- Some of the best things can come from uncertainty and learning to act in the face of it.
[0:15:35] Leadership is Not the Absence of Uncertainty
- There are 3 Responses to Uncertainty:
  - Denial
  - Overconfidence
  - Or Analysis Paralysis
- Huge Companies Have Crumbled Being Unready for Unknown-Unknowns
[0:17:30] If you don’t have any uncertainty...you may have larger problems.
- The further you move from this moment, the greater the uncertainty.
- The pandemic proved we were all a little too certain.
- Knowing your values forms an archor point to combat uncertainty.
- Your response to uncertanty will uncover things about you and your company culture.
[0:26:35] Parting Words
- Remember, if you've identified it, then it's a risk, not an uncertanty.
- When planning and identifying uncertanty, opportunity often presents itself.
  - If we're somewhat aware and prepared, we're then able to pivet more readily, and shift into the next thing we're supposed to become.
    - It's not easy to accomplish, but it's worth the investment.

Work / Life Balance

32m · Published 03 Sep 11:00

Show Notes:

[0:00:00] Intro | Brief Recap

A Look Back on ‘Humanizing Your Team’
Final Part of the Series on Distributed/Remote Work

[0:02:50] Work/Life Balance vs Work/Life Integration

“Work/Life Balance is a Scam”?
When we think about work/life balance, we tend to think of it as:
- “I go to work to provide for the life I want to live, and I’m trying to intentionally keep those two things separate.”
- - We argue that what we’re looking for is not necessarily “Work/Life Balance”, but rather Work/Life Integration.
Instead of segmenting your life into work, play, downtime, etc.-- it’s the complete package we should embrace.
- A huge part of this integration is catalyzed in being happy with your work and feeling fulfilled with what your work asks of you from a creative and productive standpoint.
- This integration will naturally look different for everyone.
- Does your life need separation from your workplace, coworkers, and to-dos?
- - Or is it that your work just needs to better align with your non-work activities, responsibilities, and needs?
Work/Life Balance is about drawing lines in the sand, whereas Work/Life Integration is about flexibility and freedom.
- Even with integration, boundaries are important, necessary, and generally appreciated by all.
The more you can remove “putting out fires”, synchronous communication, and immediacy from your work, the easier it will be to have a sincere and stable Work/Life Integration.
- All of which assists greatly in combating and preventing burnout.

[0:17:57] Work/Life Integration Still Requires Intention, Strategy, and Planning

Incessant roadblocks, waiting for others, and spending your time “task hopping” isn’t an integration issue...it’s a strategy and planning issue.
- Plan ahead, think of the resources you need, gather those things, then build/create, etc.
- - Need feedback? Don’t wait, hand it off and move on.

[0:21:41] Things We Do to Ensure Quality Work/Life Integration

If you’re privileged enough, having a dedicated space is a great boon.
- If you can’t do that, coffee shops and local libraries are solid alternatives.
Determine what is essential in your life.
- Essentialism can help!
- Then determine what you ‘need’.
- - Followed by what you ‘want’.
- What does your ideal life look like?
- - It comes from a place of privilege, admittedly, but it’s worth considering nonetheless.
  - This isn’t something you ask and consider once.
  - - Ask yourself often for alignment.

[0:30:33] Parting Words

Topic Takeaways and Last Minute Tips
- Protect your schedule.
- It’s okay to have bad days, weeks, months, etc.
- - Don’t dwell in it.
  - It’s ok to feel unprepared.
  - - But the time to start creating the life that you want is TODAY!

Humanizing Your Team

28m · Published 26 Aug 11:00

Show Notes:

[0:01:12] Intro
- Brief Recap on the Last Episode of AIB
[0:02:05] “How to not turn your coworkers into your crazy Facebook uncle.”
- In a polarized world where everything is extreme, our society has a habit of pitting us against each other on most topics and issues.
- We evolved to be able to read body language and in-person communication.
  - But now we need to adapt to modern technologies and to the landscape of changing industries, and distributed workforces.
- Unlike Facebook, you can’t just turn off your coworkers.
  - How we humanize each other goes a long way toward creating a healthy and safe work environment.
- [0:06:03] Things we can do to humanize our perceptions of others and eliminate our own biases:
  - Give people spaces to discuss things that aren’t work-related.
  - Find out where you all have common ground.
  - Avoiding apathy out of anger, frustration, or as a symptom of poor communication.
[0:12:06] Things you can do to ensure broader interaction between coworkers:
- Personality Profile Workshops & Team Discussion
  - Enneagram
  - Strength’s Finders
  - Etc
- All-Team Video Calls
  - Cross-departmental discussion encouraged.
  - Don’t mandate or assume you’ll have every person on the team for every call.
- “Off-site” Events
  - Company Retreat/Summit
  - Sporting Event
  - Etc
- Any & All Common Ground Interactions
  - Experiment.
    - Find what works for your teams and company culture.
- Friendly Unmandated Coworking Calls
- Automated Check-ins Unrelated to Work
  - E.g. “What’s something you saw recently that you found interesting?”, or, “Have you read any good books you’d recommend of late?”
- Regularly Recorded and Publicly Shared Shoutouts
  - Hearing someone praise your work, or the work of others makes it really hard not to like them. :)
[0:25:50] Parting Words & Last Minute Insights
- Take the time to get to know your coworkers, beyond just their roles and opinions, political or otherwise.
- You don’t have to be friends with everyone you work with, but there is no harm in liking everyone you work with.
  - And that is more on you than it is on them, so put forth that effort to get to know them.
    - At the end of the day, the choice is yours.

Set-Up for Success for Distributed Teams

32m · Published 19 Aug 11:00

Show Notes:

[0:00:54] Intro

You have found it!
Jeremy messes up Kevin’s ‘flow’.
Very Brief Last Episode Summary

[0:2:23] Decisions We’ve Made to Set Up for Success for Distributed Work

Rule #1: Experiment!
- Rule #2: Test what works for you, throw away the rest.
Categorizing our decisions by clarity, connection, and collaboration.
How transitioning to distributed, at first, brought teamwide clarity to a halt.
- Being colocated for so long was our crutch, the one that made us think we were better at clarity than what we actually were.
- Looking back, we also confused in-office distraction and being “busy” for solid communication and real progress.
- - Which is certainly less than ideal.
If Slack communication is the main way you run your business (like ours was), you may find clarity, quality communication, and work/life balance to be suffering.
Distributed isn’t isolated to software.
- Jeremy elaborates on his time with bankers and his remote experience regarding his own work in distributed banking.

[0:09:52] Your location does matter.

- Whether that be from your home office, kitchen table, porch, coffee shop, etc.
- You probably don’t need a “private space”, but you definitely need a “dedicated space”, or spaces.
- Long term distributed success justifies routine and normalcy, strengthened by your own personal dedicated workspaces.
Some of the business owner tips and tricks to enable a successful transition to distributed work.
- Thoughts on automatic check-ins.
- - High-fives & Shoutouts
- Heartbeats and Cycle Kick-offs
- Friendly nudges.
- Leading by example.
- You don’t actually need long recurring meeting to build clarity.
- - How you’re probably doing meetings wrong.
  - You might just need an internal organization specific podcast.
  - - How a weekly internal podcast improved clarity and communication.
- If a piece of information is important, you should be communicating the same information across all your channels (at relatively the same time), be that via message board, email, podcasts, etc.
- - If you’re tired, and sick, or bored of saying the same thing over and over, keep in mind that you’re just at the point of the entire team having absorbed and registered that information.
- Infrequent coworking calls-- consider them.
- Personality tests and discussions.
- A place for water cooler discussions and hobby chats.
- - It might go without saying, but coworking call, water cooler & hobby talk should always be treated as optional, not mandatory.
- Have some back-up plans so that poor internet connection and other obstructions don’t ruin your work day.
- Good camera, lighting, etc.-- all welcome additions.
- If you don’t have a private workspace: a good pair of noise cancelling headphones.
- Find the right space for your team, whether that’s Slack, Basecamp, whatever-- experiment and find what works for you...not all of them will.
- Consider any special needs of individual employees.
- - Vision, hearing challenges as an example.
- Don’t expect to go into distributed work high performing.
- - There will absolutely be a challenging (though ultimately rewarding) transition time.
  - - Give yourself and your team/s plenty of grace.

[0:30:37] Parting Words

Patience is the key!
Create a framework for solid communication.

Why We Chose Distributed Work

30m · Published 05 Aug 11:00

Show Notes

[0:00:00] Episode Summary | Intro

[0:02:25] Remote Work: Pros/Cons

How we’ve done it, and how you can learn from our mistakes.
There are options.
- The pandemic has made a huge portion of people realize their jobs can be done from home.
- - Not everyone is going back to the office, and for valid reasons.
The pros far outweigh the cons.
Comfort and convenience go a long way toward being productive.

[0:06:40] Why We Chose Distributed

- We started as a completely co-located business.
- - Think 1/3rd....or 1/10th of Silicon Valley and you have the right idea.
- In late 2019 we decided it was time for a shift.
- - Being pre-pandemic, the thing that made us kick-off a new normal was quite simply that our office became less desirable.
  - - And inconvenient parking (aka no parking) led to distributed considerations...seriously.
  - We were always remote friendly, but more people started working off-site: from local coffee shops, gastro-pubs, their homes.
  - We misunderstood business for productivity.
  - Being co-located was actually instigating poor communication.
- Jeremy’s 15+ years of Distributed Work Experience
- - How his experience encouraged a dramatic change in where and how we conducted business.
- We also brought on a new team through an acquisition, which only further exemplified the need for this change.
- We chose distributed over hybrid for a reason.
- - We did attempt a hybrid approach for a brief time, but we were slowly learning that even it wasn’t the best People First fit for our business.
[0:18:34] ...and then the pandemic happened.
- Converting processes, communication, and our approach to clarity and collaboration had to be rethought and reconsidered from almost every angle.
- - And we continue to refine and iterate even now.
- There was a huge mental shift for James and Kevin in how they had to think about what they were doing, and how to lead a distributed team-- simply how to make it work.
- The dangers of the hybrid space stem from communication issues.
- - The people not co-located often pay for this by not receiving the clarity and collaboration that co-located team members were.
  - - The answer was moving to 100% distributed.
    - - Which we’ll unpack in the next episode of Adventures in Businessing.

[0:24:31] Closing Thoughts, and one additional thing to NOT do if you plan to shift to distributed work.

Don’t jump the gun, and try to plan out a timeline for what going distributed could/would look like, and how it might affect individuals, and teams, for better and worse.

Managing Up

30m · Published 29 Jul 11:00

Show Notes

[0:00:00] Episode Summary | Intro

Jeremy tries out new greetings…
- And also recommends everyone watch Guga Foods.

[0:02:16] Managing Up & Why it Works

Challenging...and comes with many landmines.
- Do it right and your life is easier.
- Do it poorly and it could make your work and culture really suffer.
You can’t control whether someone is a good or bad manager, but you can put your best foot forward.
- You have very real restrictions in how you can deal with a manager, and how you interact with them.
Managers aren’t perfect, and are oftentimes someone who was in a similar role to you, but was good enough at their job to be moved up (sometimes against their will or desired growth path).
- This however does not mean that they’ll inherently be a good manager.
Rarely is a manager ever actually ‘out to get you’, but poor communication and misunderstandings can make it feel like the opposite.
- Over communicate.
- - Don’t assume you’re on the same page and that you have the same goals or high level view of the work and tasks at hand.

[0:09:55] Healthy Ways to Communicate

Force Clarity
Ask Questions
- Also ask good questions. ;)
Understand How You’ll be Measured
- How will you know you’ve done a good job?
- How do you know when you’re excelling or falling behind expectations?
- - Try to avoid unwritten/undiscussed expectations from both parties.
- Share what success looks like to you.
- - Make efforts to humanize yourself and your manager by finding that common ground.
- Don’t be afraid to negotiate priorities when you’ve developed a good rapport with your manager.
Recurring check-ins are great refreshers and reminders of what’s on your plate.
- Which helps measuring workload.

[0:19:57] Be to Solution...with caveats.

Figure out ways to remove stress and not be the source of stress for your manager.
If you bring an issue to your manager, attempt to bring a solution, or a series of solutions.
- When you come with a solution you give your manager options, which provides the potential for them to lead well.
- - You also shape how you’re known. You can be known as the person for solutions, or for problems.
  - - You have to decide which you want to be known for. (This all assuming you don’t work for, or belong to, a toxic culture.)
Some situations can be fixed.
- But you might be able to course correct and salvage what’s there.
- If you can’t manage up, it might be time to think about transitioning out.

[0:26:15] Parting Words

Just like peer relationships, managing up is never done.
- It’s an ongoing process, and it’s an uneven relationship with a “balance of power” to keep in mind to make sure you’re handling that relationship in a productive manner.

Subscribe/Follow us on Ciircles.com for more helpful advice, best practices, and tips that cover all kinds of solutions to workplace tensions and challenges.

Managing Relationships with Others

30m · Published 22 Jul 11:00

Show Notes

[0:00:39] Episode Summary | Intro

Jeremy gets “folksy”.
All relationships take work and conscious effort to make them affective.
- This applies to work, family, and friends.
- You’re managing relationships, even when you’re not.

[0:06:06] Diving Into Managing Relationships Well

Communication Mistakes
- We often go in NOT assuming the best.
- - Whether you’re sick, maybe you slept poorly, etc.
  - We’ve found that very-very rarely does anyone actually have any ill intent going into their interactions.
  - Assume the best!
  - With the advent of social media dominance, the world at large right now needs to come together and acknowledge there are MANY more individuals with you than against you.
  - - And those people want peace, kindness, equality, and much more for themselves and others.
If you are going to manage your relationships well, you’re going to have to listen.
- Listening is a skill that takes effort, and it’s not one people come by naturally.
- Listening isn’t, and shouldn’t be used as, a gateway to counter points, attacks, and conversational dominance.
- - The goal is to listen twice as much as you talk.
Questions are key.
- To great benefit, asking the right questions after engaged listening can unlock a lot of mutual understanding and trust.
- - But questions shouldn’t come veiled with “gotcha” scenarios painted in, and should never be used to set someone up for failure.

[0:13:25] Other Thoughts on Managing Relationships

Relationships aren’t one and done, they’re ongoing.
- Intention and ongoing effort are required.
- Some relationships come easier than others, and sometimes that’s a good thing.
- - Though we do have to be careful about spending all our time and efforts on what comes easy, while letting other relationships slip up.
Respond, don’t react.
- Teaching yourself to think about your response is always worth the investment.
The best relationships work when you don’t have the walled off facade in the way.
- Measure this for yourself and context is important.
- - But there is something to say for being honest and sharing your feelings in earnest.
  - - Otherwise bitterness becomes the poison you drink...assuming the other person will get sick.
Sometimes you just have to be humble and apologize.
- Too often work relationships fall apart because of one person or the other refusing to be wrong or accept the blame.
- - Some of this can be from a toxic work culture, but a lot of it can be prevented.

On that note, if you come from a toxic work culture, let us know!

We want to help you get out of that, or improve that situation; and we have a network of amazing professionals who just might be able to help.

Be a person and place that is safe to fail around.
- We can’t improve without failing.
- - Help others navigate failure and acknowledge efforts of others with grace and humility.

[0:23:57] Sometimes we make mistakes when we should know better…

It’s easy to just pile on, try offering support.
- We all need allies, not enemies. So put that supportive energy out in to the world and help others rather than ridicule.
Unspoken expectations are the landmines of all relationships.
- Assume the best, but don’t assume others know your expectations of them.
- Communicating expectations is so very important; the sooner the better!

[0:28:45] Parting Words

Spend time thinking and being intentional about your relationships in your life today, and the ones you wish could be better.
- Then ask how you can improve yourself to meet those relationship goals.

Managing Yourself

29m · Published 16 Jul 03:47

Show Notes

[0:01:05] Episode Summary | Intro

Give Us Your Thoughts on the Show!
- Find us on Twitter @Ciircles

[0:03:16] Managing Yourself

Applicable to Everyone, Even if You’re Not Actively in a Leadership Position
If you don’t have a culture of people who can/will self manage...you’ll notice it quickly.
In distributed work you have to focus on objectives over time tracking.
- Activity can be disguised as progress, but oftentimes it’s anything but.

[0:07:12] Things we do to Manage Ourselves

Incrementally enhancing the mundane has a positive ripple effect.
- Improving sleep is a prime example.
Start every day with a loose list of things you can accomplish, that which if completed will ensure you feel successful.
- Identify your Essential Three:
- - What are the three things that are imperative to move forward today?
- Try to make sure the thing you do not want to do is on that list, attempt it first; the goal is that hopefully you can then snowball through the rest of the day on easy mode.
Get your mind engaged without focusing on work.
- Whether through exercise, meditation, spiritual and/or philosophical studies.
- Be wary: you can’t have multiple focuses and still be focused.

[0:17:29] The Crucial Piece in Self Management is Finding Time to Unplug

Self-care is 100% vital.
- Schedule, prioritize, and protect your time for self-care.
- Be flexible and don’t punish yourself when things don’t go according to plan.
- - You will have bad days, and if you can accept that, you can bounce back from it with greater success.

[0:22:05] Preventing “Bad Days” as Much as Possible

What are the distractions that could get in your way, the things that could steal you away from a good day?
- We all have our own triggers, but being mindful of them can help you avoid distractions on a daily basis.
We can underestimate the impact of minor disruptions.
- Rarely are you responsible for putting out every fire.
Be flexible, but stick to your schedule overall.

[0:27:42] Parting Words & Advice

There’s always more work to be done than there is time.
When you’re managing relationships, the most important one for you to be managing is yourself.
Next Time on AIB

Adventures in Businessing: Entrepreneurship, Small Business, and a Healthy Dose of Humor has 100 episodes in total of non- explicit content. Total playtime is 66:02:14. The language of the podcast is English. This podcast has been added on August 20th 2022. It might contain more episodes than the ones shown here. It was last updated on April 8th, 2024 09:14.