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Should We Open a Bar? | Slightly Unhinged with Sean O’Hare
In this episode of Slightly Unhinged, Justin sits down with Sean O’Hare, founder of Evolution RoofWorks, owner of PDX DJs, flight attendant for Alaska Airlines, entrepreneur, casino enthusiast, and one of Justin’s favorite humans.
What starts with talk of opening a bar and spirals through business ideas, entrepreneurship, friendship, and chosen family turns into a much more real conversation about support systems, identity, ambition, and the people who actually show up for you when it matters. Sean has a way of turning the mic right back on Justin, which makes this episode feel a little different from the usual format in the best way.
They get into entrepreneurship, family complexity, allyship, social media, housing, roofing, and the emotional side of building something from the ground up. It’s chaotic, funny, honest, and unexpectedly personal.
In this episode
how Sean ended up owning multiple businesses at once
why entrepreneurs always seem to have one more idea
the fantasy of opening a nasty grungy Portland bar
what chosen family really looks like
Justin on siblings, family complexity, and letting go
the emotional reality of building Blake & Alder
why support systems matter more than blood sometimes
how Sean got into Alaska Airlines
what Evolution RoofWorks is really built around
why human-first business actually matters
the kind of friendship that lets a conversation go from chaos to something real
About the guest
Sean O’Hare is the founder of Evolution RoofWorks, a roofing company dedicated to delivering high-quality craftsmanship and a better overall experience for homeowners. Since launching the company in 2024, he has focused on raising the standard in the roofing industry through transparency, attention to detail, and a strong emphasis on quality work. With a passion for both construction and customer education, Sean works closely with clients to ensure they fully understand their roofing investment. He’s committed to building a company known not just for great roofs, but for trust and long-term value.
Sean also owns PDX DJs and works as a flight attendant for Alaska Airlines, which makes this episode especially fitting for someone who somehow manages to live several careers at once.
Connect with Sean O’Hare
LinkedIn
https://www.linkedin.com/in/sean-ohare-pdx/
Evolution RoofWorks
Website
https://www.EvolutionRoofWorks.com
Instagram
https://www.instagram.com/evolutionroofworks?igsh=MTBkcjhza3FxZWxkcw==
Preferred call to action
Visit website or call/text to schedule a roofing consultation.
PDX DJs
Website
https://www.thepdxdjs.com/
Instagram
https://www.instagram.com/pdxdjs?igsh=MXJvZGcwN3V6aXl3MA==
Mentioned in this episode
Jordyn Jones
Website
https://www.jjoneshomes.com
Instagram
https://www.instagram.com/jordyn.jones.realtor
LinkedIn
https://www.linkedin.com/in/jordynj/
YouTube
https://www.youtube.com/@jordynjonesrealtorportland/videos?app=desktop&view=0&sort=dd&shelf_id=2
Ghost Hill Cellars
https://www.ghosthillcellars.com/
Poop Solutions PDX
https://www.poopsolutionspdx.com/
Mental health and suicide prevention
This episode includes a real conversation about mental health and suicide. If you’re struggling right now, please know you are not alone and there is support available.
If you are in immediate danger or may harm yourself, call 911 right away.
If you are in the U.S. or Canada, call or text 988 for the Suicide & Crisis Lifeline.
https://988lifeline.org/
Please reach out to someone. Support is here, and your life matters.
Follow the show
Instagram
https://www.instagram.com/slightlyunhingedthepodcast/
Subscribe
Follow, like, and subscribe to Slightly Unhinged for more episodes that start in one place, spiral somewhere unexpected, and still manage to land somewhere real.
View all episodes
By Justin PavisIn this episode of Slightly Unhinged, Justin sits down with Sean O’Hare, founder of Evolution RoofWorks, owner of PDX DJs, flight attendant for Alaska Airlines, entrepreneur, casino enthusiast, and one of Justin’s favorite humans.
What starts with talk of opening a bar and spirals through business ideas, entrepreneurship, friendship, and chosen family turns into a much more real conversation about support systems, identity, ambition, and the people who actually show up for you when it matters. Sean has a way of turning the mic right back on Justin, which makes this episode feel a little different from the usual format in the best way.
They get into entrepreneurship, family complexity, allyship, social media, housing, roofing, and the emotional side of building something from the ground up. It’s chaotic, funny, honest, and unexpectedly personal.
In this episode
how Sean ended up owning multiple businesses at once
why entrepreneurs always seem to have one more idea
the fantasy of opening a nasty grungy Portland bar
what chosen family really looks like
Justin on siblings, family complexity, and letting go
the emotional reality of building Blake & Alder
why support systems matter more than blood sometimes
how Sean got into Alaska Airlines
what Evolution RoofWorks is really built around
why human-first business actually matters
the kind of friendship that lets a conversation go from chaos to something real
About the guest
Sean O’Hare is the founder of Evolution RoofWorks, a roofing company dedicated to delivering high-quality craftsmanship and a better overall experience for homeowners. Since launching the company in 2024, he has focused on raising the standard in the roofing industry through transparency, attention to detail, and a strong emphasis on quality work. With a passion for both construction and customer education, Sean works closely with clients to ensure they fully understand their roofing investment. He’s committed to building a company known not just for great roofs, but for trust and long-term value.
Sean also owns PDX DJs and works as a flight attendant for Alaska Airlines, which makes this episode especially fitting for someone who somehow manages to live several careers at once.
Connect with Sean O’Hare
LinkedIn
https://www.linkedin.com/in/sean-ohare-pdx/
Evolution RoofWorks
Website
https://www.EvolutionRoofWorks.com
Instagram
https://www.instagram.com/evolutionroofworks?igsh=MTBkcjhza3FxZWxkcw==
Preferred call to action
Visit website or call/text to schedule a roofing consultation.
PDX DJs
Website
https://www.thepdxdjs.com/
Instagram
https://www.instagram.com/pdxdjs?igsh=MXJvZGcwN3V6aXl3MA==
Mentioned in this episode
Jordyn Jones
Website
https://www.jjoneshomes.com
Instagram
https://www.instagram.com/jordyn.jones.realtor
LinkedIn
https://www.linkedin.com/in/jordynj/
YouTube
https://www.youtube.com/@jordynjonesrealtorportland/videos?app=desktop&view=0&sort=dd&shelf_id=2
Ghost Hill Cellars
https://www.ghosthillcellars.com/
Poop Solutions PDX
https://www.poopsolutionspdx.com/
Mental health and suicide prevention
This episode includes a real conversation about mental health and suicide. If you’re struggling right now, please know you are not alone and there is support available.
If you are in immediate danger or may harm yourself, call 911 right away.
If you are in the U.S. or Canada, call or text 988 for the Suicide & Crisis Lifeline.
https://988lifeline.org/
Please reach out to someone. Support is here, and your life matters.
Follow the show
Instagram
https://www.instagram.com/slightlyunhingedthepodcast/
Subscribe
Follow, like, and subscribe to Slightly Unhinged for more episodes that start in one place, spiral somewhere unexpected, and still manage to land somewhere real.