

Gay Men Going Deeper
Gay Men's Brotherhood
Gay Men Going Deeper is a weekly podcast that showcases raw and real conversations about personal development, mental health, and sexuality - from an unapologetically gay perspective.
Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time.
This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between.
Visit us at www.GayMenGoingDeeper.com
Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN
Hosted by Matt Landsiedel and Michael DiIorio, and featuring a wide range of special guests, you can expect to be inspired, entertained, and even a little triggered from time to time.
This provocative podcast is for anyone who craves deeper conversations on topics ranging from spirituality to sexuality - and everything in between.
Visit us at www.GayMenGoingDeeper.com
Support the show: https://www.paypal.com/donate/?hosted_button_id=LT55M79CMH5FN
Episodes
Mentioned books

Oct 6, 2022 • 50min
Trusting Yourself
We often talk about trust in the context of trusting others, but in this episode, we’re focusing on how to build an internal sense of trust.
We’re exploring questions such as:
How do you know if you trust yourself? What gets in the way of trusting yourself?What is one thing you can do to build greater self-trust?
Join us for this informative conversation that will help you develop your relationship to self, and ultimately your relationship with others.
Take the Attachment Style Quiz!
Watch this ep on YouTube
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Join the private Facebook community
Take our "Building Better Relationships" course
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Sep 29, 2022 • 53min
Making Space for Being Uncomfortable
In today’s episode, host Calan Breckon and guest Drummond Fulcher dive into the uncomfortable for a conversation that revolves around cancel culture, the "either you’re with me or against me (or us)" mentality, giving space for the in-between where conversation happens, how bridges are where understanding is born, and where we need to go in order to work through the uncomfortable feelings in order to learn and grow.
Together they unpack questions like:
Why do people avoid being uncomfortable?How do you think cancel culture affects our community?How do we make space in our lives for being uncomfortable and having hard conversations?
Take a listen to find out how you can better navigate uncomfortable conversations and begin building more bridges of understanding and compassion in your life today.
More on Drummond:
@DrummondCultureWebsite
Take the Attachment Style Quiz!
Watch this ep on YouTube
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Sep 22, 2022 • 54min
Your Questions Answered
You asked and we answered!
In this episode, we're answering some of the juiciest questions from our community such as…
How to let go of the past?Why can’t gay men find love?How to get unstuck and move forward?
Join us as we cover topics such as shame, gay dating, self-confidence, and trust in this Q & A style discussion.
Take the Attachment Style Quiz!
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
Instagram
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Sep 15, 2022 • 1h 11min
Behind the Scenes of the Gay Men’s Brotherhood
In this very special 💯 100th episode 💯, we are taking you behind the scenes of the idea that started it all, The Gay Men's Brotherhood.
Today, we represent a group of thousands of men who share a vision to create a community where people feel more authentically connected to one another and feel comfortable showing up vulnerably so deeper intimacy can be established within our community.
We have invited our moderators to the podcast to join us as we share our personal experiences as a leadership team.
In this episode we talk about:
► The origin story of the Gay Men's Brotherhood
► How this community has impacted our lives
► What it's like to be a leader in the group
► The challenges that come with being part of a community
► Our fondest memories
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Sep 8, 2022 • 48min
Our Community
From the outside looking in, the queer community is seen as an inclusive space that celebrates diversity. Yet for many people, it feels quite exclusive and lonely.
In this episode, we are sharing our vision for the gay community and the different ways we are implementing this vision.
We’re talking about...
What exactly is our vision?What are the different parts of our community?Why is building this community important to each of us?How we’ve changed from the beginning to today?What is one thing we’re excited about co-creating for our community in the future?
Take the Attachment Style Quiz!
Watch this ep on YouTube
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Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Sep 1, 2022 • 56min
The Dark Night of the Soul
Dark periods are an inevitable part of life that can happen at any moment and in any number of ways:
The death of a loved one
A terminal diagnosis
Job loss
Relationship breakdown
But what is the spiritual and psychological significance of this pain?
In this episode of Gay Men Going Deeper, Michael is joined by LGBTQ+ affirmative psychotherapist Justin Oberste to discuss the concept of the Dark Night of the Soul, including:
The 4 phases of a dark night of the soul
Sharing personal, real-life examples
The spiritual significance of dark periods
Tips for finding hope within the darkness
The 4 Phases of a Dark Night of the Soul - blog post referenced in today's episode
Connect with Justin
Website: www.justinoberste.com
Instagram: www.instagram.com/justinoberste
Today's Host: Michael DiIorio
Website: https://www.wellismo.com
Instagram: https://instagram.com/wellismo_coach/
Courses: learn.wellismo.com
Watch this ep on YouTube
Take the Attachment Style Quiz!
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Join the private Facebook community
Take our "Building Better Relationships" course
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Aug 25, 2022 • 43min
Mindset
Your mind is a powerful tool that you can use to create a life that you love. Your mindset is your overall outlook on life and it will determine whether you remain stuck spinning your wheels or moving towards your goals and dreams.
In this episode, we’re looking specifically at the difference between the Fixed and Growth Mindsets. We will be discussing questions such as….
What type of mindset were you raised with (growth of fixed)? And what mindset do you have today?How do you cultivate more of a growth mindset for yourself? What did you have to transform to become a more growth mindset-oriented?What is your internal dialogue in a fixed mindset say to you vs. when you’re in a growth mindset?What has helped you on your growth journey that may help our listeners?
By the end of this episode, you’ll feel motivated and inspired to leave behind the fixed mindset and shift into a growth mindset.
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Aug 18, 2022 • 1h 17min
Pretty Privilege
In this episode, Matt Landsiedel and Andre-Lee Wills unpack the hot topic of pretty privilege.
Pretty privilege works on the principle that people who are deemed more attractive—based on accepted societal beauty standards—have an upper hand in the world and are afforded many opportunities that less “attractive” people don't have. Yet, it's not often that people are willing to admit it—or even talk about it—especially if they’re on the receiving end of its benefits.
Here is what Matt and Andre-Lee explored in this episode:
What is pretty privilege?What is your personal experience with pretty privilege?Why is this topic important for gay men to discuss?What does it mean to be attractive?Why does our culture place so much emphasis on attractiveness?How does pretty privilege relate to ageism, racism or sexism?How can we start to deconstruct the system that is conditioning us to be so limited in our definition of attractive?
Connect with Andre-Lee:
Andre-Lee Wills is an Empowerment Coach. He uses his unique gifts and talents to offer guidance, support, and assistance to others in being an expression of their truest and highest self. He is adept in career coaching, life and relationship coaching, communication, team building, and organizational management.
mrandreleewills@gmail.com
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take the "Healing Your Shame" course
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
Instagram
GayMenGoingDeeper.com
Patreon
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Join the Gay Men Going Deeper Membership coaching community!

Aug 11, 2022 • 1h 5min
Open and Closed Relationships (Vol. 2)
As more people are choosing to explore non-monogamous relationships, the discussion about open and closed relationships can be divisive and unhelpful.
In today's episode, we are having an open conversation about open and closed relationships that will enrich your understanding of the many different types of relationships out there and help you figure out what's right for you. We will cover questions such as:
What is the ideal relationship structure for you?How do you handle jealousy in your relationships?Which of your needs do you expect your primary partner to meet and which needs can be met outside the relationship?What tips will help someone decide which relationship structure works for them?
Listen to this episode to get some fresh and insightful perspectives on this hot topic.
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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Aug 4, 2022 • 36min
Community Inclusion
Recognizing and understanding privilege can be a hard pill to swallow for some. It means admitting you’re not perfect and possibly “looking bad,” which we were all taught growing up not to do.
In today’s episode, host Calan Breckon unpacks some of the hard questions around community inclusion with guest Raymond Jordan Johnson-Brown and the work they do as an indigenous wellness leader. Raymond, who uses they/them pronouns, is passionate about creating connections for marginalized groups and having courageous conversations around these sometimes hard topics.
Together they explore questions like...
How do you think people are “missing the mark” when it comes to inclusivity for racialized folks?How has your lived experience inspired your work?What is intersectionality?What are some of the ways the queer community has contributed/participated in systems of harm?What could a path forward look like to create an equitable world?
By the end of this episode, you’ll have a better understanding of how you can be more courageous about getting uncomfortable and having those sometimes difficult conversations around inclusivity.
Follow Raymond on Instagram: @TheOnlyRJJB
Foundry BC
Watch this ep on YouTube
- Connect with us -
Join the private Facebook community
Take our "Building Better Relationships" course
Take the Attachment Style Quiz!
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