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    Software How-To

    Getting Into Infosec

    Interviews with people who have transitioned and got jobs in #infosec and #cybersecurity so you can learn and be inspired from their experience. There is no linear path into the field of Information Security, so the hope is that you will resonate with at least one of the guests. Some of my guests were teachers, paralegals, librarians, military vets, developers, and IT help desk techs (to name a few) before transitioning. Also featuring “spoof” ads poking fun at the industry.

    Advertise

    Copyright: © 2020 Ayman Elsawah

    • Apple Podcasts
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    Latest Episodes:
    Masha Sedova - From Generations of CS to Behavioral Science and Entrepreneurship Mar 22, 2019
    Show notes

    Masha Sedova comes from a history of computer scientists! Her grandmother was in the first Computer Science graduating class in 1954 under Stalin in the Soviet Union! She loves challenges and is now utilizing what she thought was a waste of time in Liberal Arts to conquer challenges in Information Security using behavioral science, emotional intelligence, and other human factors.

    BIO

    Masha Sedova is an industry-recognized people-security expert, speaker, and trainer focused on engaging people to be key elements of secure organizations. She is the co-founder of Elevate Security, delivering the first people-centric security platform that leverages behavioral-science to transform employees into security superhumans. Before Elevate, Masha Sedova was a security executive at Salesforce where she built and led the security engagement team focused on improving the security mindset of employees, partners, and customers. In addition, Masha has been a member of the Board of Directors for the National Cyber Security Alliance, and a regular presenter at conferences such as Black Hat, RSA, ISSA, Enigma, and SANS.

    Notes

    • Grandmother was in the first Computer Science graduating class in 1954 under Stalin in the Soviet Union!!

    • Her Grandma taught her dad and her dad taught her programming around the 6th grade.

    • Had access to a computer only through the local University.

    • Masha began her search into 3 disciplines

      • Game Theory
      • Positive Psychology
      • Behavioral Science

    • Leaderboards are better for only a small subset


    Quotes

    • "You can't patch a human being."

    • "We've taken a technology solution to a human problem, and I think that's totally wrong way of going about it."

    • "Without the human interaction we would not have been able to get that alert."

    • "Focus on failure as an eventual outcome."

    • "I like picking hard challenges and very tall mountains to climb and computer science seemed like a tall mountain."

    • "If you give people the correct amount of challenge, that is a state of happiness."

    • "I found that leaderboards are effective for a small subset of people."

    • "The reasons people don't do things is not because they don't know."


    Links

    • 6:1 Positive Feedback Ratio for Performance: https://medium.com/@Praiseworthy/harvard-research-finds-employees-need-a-6-1-positive-feedback-ratio-to-perform-their-best-8f14160a8fbd

    • Dr. Gottman: https://en.wikipedia.org/wiki/John_Gottman

    • Reality is Broken by Jane McGonigal: https://www.amazon.com/Reality-Broken-Games-Better-Change/dp/0143120611

    • Flow by Mihaly Csikszentmihalyi: https://www.amazon.com/Flow-Psychology-Experience-Perennial-Classics/dp/0061339202/

    • BJ Fogg: https://www.bjfogg.com/

    • Opower Report: https://www.povertyactionlab.org/evaluation/opower-evaluating-impact-home-energy-reports-energy-conservation-united-states

    • Predictably Irrational by Dan Ariely: https://www.amazon.com/Predictably-Irrational-Hidden-Forces-Decisions/dp/006135323X

    • Intro Music (Cascadia by Trash80): https://trash80.com/#/content/133/weeklybeats-2012-week5

    • Outro Music (Quincas Moreira - Entire): https://www.youtube.com/watch?v=DoKpuXyIyVs


    Getting Into Infosec

    • Twitter: https://twitter.com/coffeewithayman
    • YouTube: https://www.youtube.com/channel/UCg6gV_gdfc188HZdN8LUx4A
    • Book: https://www.amazon.com/Breaking-Step-Step-Starting-Information-ebook/dp/B07N15GTPC/

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    BONUS - InfosecJon Learns Trust But Verify The HARD way Mar 20, 2019
    Show notes

    InfosecJon expands on some CRAZY follies he experienced during his times in the Navy. He learns through trial by fire, literally: trust but verify!

    Notes

    • Jon almost gets crushed inside the engine of Naval ship

    • A boiler exploded and Jon, a jr. engineer, was left in charge of the situation and had to give orders

    • Jon got soaked with engine Oil on a running ship, resulting in the loss of pitch-control

    • Luckily, Jon was wearing a PEP suit

    • Tag-out manual: https://www.public.navy.mil/NAVSAFECEN/Documents/afloat/Surface/Rsrcs/References/TUM_REV_07.pdf


    Getting Into Infosec

    • Twitter: https://twitter.com/coffeewithayman
    • YouTube: https://www.youtube.com/channel/UCg6gV_gdfc188HZdN8LUx4A
    • Book: https://www.amazon.com/Breaking-Step-Step-Starting-Information-ebook/dp/B07N15GTPC/

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    InfosecJon - From Rudderless Youth to Navy Engineer to Security Professional Mar 16, 2019
    Show notes

    InfosecJon runs a website cataloging his learning and dedicated to helping others get in the field. He shares his personal story from a directionless youth to enlisting in the Navy (and its follies) and his tribulations getting into the field. He also shares some interesting Navy stories. Look out for the bonus episode!

    BIO

    Jon is a father, husband, and a veteran. He went from an aimless youth to enlisting into a career path he never liked. After 7 years as an electrical engineer, he got the chance to pursue his dream of working in information security. Now, he runs a website devoted to helping others.

    Notes

    • By almost getting crushed in a two-story engine, Jon learned to be adaptable to the situation
    • Got exposure to computers by working with dad at his computer store
    • Was an engineer at heart who fell in love with the inner workings of things and how they work
    • Became the go-to person for technology in his department
    • Always had a knack for helping others, even before the military

    Quotes:

    • "[The] biggest skill I got was to be able to figure things out quickly and troubleshooting."
    • "You can't troubleshoot something until you know how it works."
    • "I just wanted to learn as much as I could."
    • "I want to work with technology; I want to help people."
    • "Going to a traditional school, being more mature, was [seen as] a negative."
    • "Everybody doesn't know everything. That's why most security teams are... teams!"
    • "I want to help people; I want to protect people."
    • "The networking knowledge, the [SysAdmin] knowledge, and then the drive to learn new stuff... is what they were attracted to."
    • "Nobody wanted to do it. I volunteered and stepped up."
    • "One thing that attracted me to the school 100% was the advertised hands-on labs."

    Links

    • InfosecJon (Twitter): https://twitter.com/infosecjon
    • InfosecJon (Website): https://infosecjon.com/
    • Navy C-School: https://www.quora.com/Whats-a-Navy-C-school
    • Jon on the different types of hackers: https://infosecjon.com/types-of-hackers/
    • Intro: Cascadia by Trash80: https://trash80.com/#/content/133/weeklybeats-2012-week5
    • Outro: White Smoke by Endless - http://www.endlessslove.com/

    Resources

    • SEED Labs by Syracuse University: http://www.cis.syr.edu/~wedu/seed/index.html
    • David's CTF Post: https://bsidessf.org/news/2019/03/running-the-bsides-sf-2019-ctf

    Getting Into Infosec:

    • Twitter: https://twitter.com/coffeewithayman
    • YouTube: https://www.youtube.com/channel/UCg6gV_gdfc188HZdN8LUx4A
    • Book: https://www.amazon.com/Breaking-Step-Step-Starting-Information-ebook/dp/B07N15GTPC/

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    InfosecSherpa - From Travel Agent to Law Librarian to Security Analyst! Mar 01, 2019
    Show notes

    Tracy Maleeff (@InfosecSherpa) was a professional law librarian and at the top of her game. Looking for change and meaning, she searched until she found the field of Information Security. This is her journey.

    BIO

    Tracy Z. Maleeff (/may-leaf/), @InfoSecSherpa, is an independent information professional providing research and social media consulting with a focus on information security. She is a frequent presenter on best practices of data mining from social media, professional networking, and introduction to information security topics. Tracy has 15 years of experience as a librarian in academia, corporate, and law firm industries and earned a Master of Library and Information Science from the University of Pittsburgh. She is the Principal of Sherpa Intelligence LLC–your guide up a mountain of information.

    Notes

    • There is a condition called the "Librarian Face"

    • Librarians who have a Master's Degree in Library Science are taught to be approachable

    • Was never a public librarian; she worked in "special" libraries. This made her really good at finding and accessing data

    • Tracy shares some social engineering tricks she did earlier in her life

    • Didn't grow up with computers around her

    • Advice: "Know yourself"


    Quotes

    • "If you are out in public… people are likely [going] to come ask you questions because you look like you know things."

    • "I did fail, but I did not fail as badly as I thought I would!"

    • "I don't regret the path that I took."

    • "For someone like me who does come from a technical background... having the certifications is what people want to see."

    • "They need to see some receipt!"

    • "Even if it turned out to be nothing, don't be afraid to speak up."

    • "I don't think I realized it was social engineering; I just knew it was something that I wanted."

    • "Managed to talk my way not only on the plane, but also into business first."

    • "They had me at port scanning."


    Links

    • Infosecsherpa: https://twitter.com/infosecsherpa

    • Women’s Society of Cyberjutsu (WSC): https://womenscyberjutsu.org/

    • Intro Music: Cascadia by Trash80 - https://trash80.com/#/content/133/weeklybeats-2012-week5

    • Outro Music: JR Tundra - Natty Roadster


    Resources

    • Art of Improvement: https://www.youtube.com/channel/UCtYzVCmNxrshH4_bPO_-Y-A

    Getting Into Infosec

    • Twitter: https://twitter.com/coffeewithayman
    • YouTube: https://www.youtube.com/channel/UCg6gV_gdfc188HZdN8LUx4A
    • Book: https://www.amazon.com/Breaking-Step-Step-Starting-Information-ebook/dp/B07N15GTPC/

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    Adrian Kaylor - From Network Admin to Trainer to Sales Engineer for Life Feb 22, 2019
    Show notes

    Adrian is a Sr. Sales Engineer at Splunk who focuses on security. He has worked for various security startups in the Bay Area for the past 15 years from vulnerability management to endpoint investigation to ML-based threat hunting.

    Notes:

    • Had an interest in security early on, starting with opening binaries on Sierra King's quest games and looking for hints.

    • Took any opportunity he got to get exposed to security

    • His job as an instructor was very useful during support and later as a sales engineer

    • Keeps a Trello board for his lab!

    • Adrian expenses (deducts) what he spends on his lab from his taxes (consult a tax attorney)

    • He mentions an awesome hack for installing Kali on a Chromebook (~22 mins)


    Quotes:

    • "I remember the first time I found Phrack, my mind exploded a little bit."

    • "Experience is experience: everything that you use (skills) will get used later on."

    • "Figure out what pieces they're missing, so you can fill them in."

    • "Go through the CIS top 20 critical controls."

    • "Be less focused on the whizbang fun stuff, and more focused to get you the most return."


    Links:

    Please thank my guests for sharing their time with us and let them know if this episode helped you.

    • Adrian Kaylor on Twitter: https://twitter.com/AdrianKaylor
    • Adrian Kaylor on LinkedIn: https://www.linkedin.com/in/adriankaylor/
    • Phrack Magazine: http://www.phrack.org/
    • Lack Rack: https://www.google.com/search?q=ikea+lack+rack&source=lnms
    • ISS: https://www-03.ibm.com/press/us/en/pressrelease/20468.wss
    • Splunk Dev License: http://dev.splunk.com/
    • CIS 20 Controls: https://en.wikipedia.org/wiki/The_CIS_Critical_Security_Controls_for_Effective_Cyber_Defense
    • JA3: https://github.com/salesforce/ja3
    • Irongeek: http://www.irongeek.com/
    • Netsec Reddit: https://reddit.com/r/netsec
    • SANS Holiday Hack Challenge: https://www.holidayhackchallenge.com/2018/
    • Garage Door Hack by Samy Kamkar: http://samy.pl/opensesame/
    • Sam Bowne's Class: https://samsclass.info
    • Adrian's Presentation on YouTube: https://www.youtube.com/watch?v=8LF96Oq_pgo (Picture of lab at 24:05)
    • Intro Music by Trash80
    • Outro Music (Liberation Theology - Exploitation is Sin):
      https://open.spotify.com/album/0oc93ZsbMluxL8H994U9MW

    Learning Resource Mentioned:

    • https://www.youtube.com/watch?v=6MYF6Zo6i6A (based on https://www.coursera.org/learn/it-security)

    Getting Into Infosec:

    • Twitter: https://twitter.com/coffeewithayman
    • YouTube: https://www.youtube.com/channel/UCg6gV_gdfc188HZdN8LUx4A
    • Book: https://www.amazon.com/Breaking-Step-Step-Starting-Information-ebook/dp/B07N15GTPC/

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    Nipun Gupta - From Security Consultant to Security Innovator Feb 09, 2019
    Show notes

    Nipun graduated during the recession, but found a job as a consultant which helped him gain experience quickly. He was in fact discouraged to pursue a career in information security due to his immigrant status. Nipun is now a Cyber Security Executive focused on innovation.

    BIO:

    Nipun Gupta is a Cyber Security Executive at a large global financial institution focusing on innovation. Armed with many years of experience helping Fortune 500 companies solve cyber risk challenges, Nipun is tasked to help his employer discover, adopt, access new cybersecurity solutions protecting against emerging threats.

    In the past two years, Nipun co-founded and ran the global Cyber Innovation Ecosystem strategy at a global consulting company with a specific focus on US and Israeli startups. He offers a strong network of security executives, startup founders, and the Venture Capital community in the West Coast and abroad. Technically proficient in network and application security, Nipun is a trusted advisor for many financial service institutions, technology, and telecom companies contributing to solutions worth tens of millions of dollars. Nipun completed his Masters of Information Technology and Information Security at Carnegie Mellon University, and has been collecting industry certifications like CISSP and SABSA ever since.

    Notes:

    • Was discouraged to go into cybersecurity due to his immigrant status

    • Graduated in a tough time during the 2008 recession

    • Discusses burnout and having to work odd hours for 6 months of the year

    • The show "24" was an influence in sparking the interest in information security

    • Shares an interesting war story where he accessed tons of files

    • Discusses the personality traits needed to be a consultant


    Quotes

    • "The biggest problem security professionals will continue to face is how to bridge that gap between technical conversation and business conversation."
    • "You have to be technical to understand the depth of the issue, but at the same time, you need to be able to express it in business language so non-technical people can make those decisions."
    • "I think you have to talk in terms of risk. Every business professional [in a] large or small company understands risk because risk can put them out of business."
    • "While I'm an introvert when it comes to working, I'm an extrovert when it comes to expressing my work-related conversations or expressing my work-related issues."

    Links:

    • Nipun on Twitter: https://twitter.com/nipungupta
    • Nipun on LinkedIN: https://www.linkedin.com/in/guptanipun/
    • SecurityTube: https://www.youtube.com/channel/UCBRNlyf9lURksAEnM-pyQdA
    • Hak5: https://hak5.org
    • Nullcon: https://nullcon.net
    • BayThreat: http://baythreat.org/
    • Intro Music - "Cascadia" by Trash80: https://trash80.com/#/content/133/weeklybeats-2012-week5
    • Outro Music - "Put This Rap Together
      " by Bobby Cole: https://www.audioblocks.com/stock-audio/put-this-rap-together%C2%A0-98857.html

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    BONUS - My Book is OUT: Breaking IN: A Step-by-Step Guide to Starting a Career in Information Security Jan 25, 2019
    Show notes

    My book is out!

    Breaking IN: A Step-by-Step Guide to Starting a Career in Information Security

    https://www.amazon.com/gp/product/B07N15GTPC

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    Marcus Carey - Childhood Builder/Breaker to Navy Cryptologist to Founder and Mentor Jan 11, 2019
    Show notes

    Marcus Carey has been hacking since he was five. A true MacGuyver, he had to make do with the little resources available to him. He later enrolled in the Navy, worked for 3- letter agencies including the NSA, and now has his own security startup. Marcus shares a TON with us in this episode.

    BIO

    Marcus is renowned in the cybersecurity industry and has spent his more than 20-year career working in penetration testing, incident response, and digital forensics with federal agencies such as NSA, DC3, DIA, and DARPA. He started his career in cryptography in the U.S. Navy, and holds a Master’s degree in Network Security from Capitol College. Marcus regularly speaks at security conferences across the country. He is passionate about giving back to the community through mentorship, hackathons, and speaking engagements, and is a voracious reader in his spare time.

    Notes:

    • Marcus had an opportunity to play college basketball, but couldn't since it was only a partial scholarship

    • After taking the ASVAB test, he had the choice of nuclear engineering or cryptography. He chose cryptography

    • Marcus made an Olympic-sized track pit up to spec as a child.

    • Marcus, like many other security professionals, had a strong artistic side. He achieved first chair in just a few weeks in Jr. High.

    • Marcus teaches us "How to Learn"

    • Marcus achieved over 115 college credits on his own, without attending college!

    • Open source tools Marcus created ended up being used be used to save people's lives in other parts of the world


    Quotes:

    • "[I] told them all I wanted to do was work with computers."

    • "I've always been a tinkerer. I built stuff, I was a science fair geek... the whole nine."

    • "I was the poorest person growing up... so anything I did was a hack. I made my own hacky sack. I used to make my own toys."

    • "You can't learn how Marcus learns because everyone is different.... Nobody can tell you how to learn as good as yourself."

    • "So now, I'm like a finely tuned weapon when it comes to learning... cause I know exactly how to learn."

    • "Never be surprised how your work turns out to be used for good... it actually blew my mind that my stuff was being used to do that [saving people's lives]. "

    • "Show externally that you've mastered those concepts in some way."

    • "Sometimes your employees are going to go rogue, and hopefully, you can detect when they do."

    • "If you're focusing on a specific set of skills that are evergreen, and if you work that long enough, it doesn't matter your aptitude: you can become an expert at that."

    • "There are people out here that are celebrities, and they act like they know everything. Don't be one of those people."

    • "Aptitude allows people to learn stuff faster. I think the military requires you to learn stuff fast."


    Links:

    • Marcus Carey Twitter (@marcusjcarey)

    • Marcus's Company: Threatcare

    • ASVAB Test

    • MacGuyver

    • Python The Hard Way

    • Sub-Vocalization

    • Book: "How to Measure Anything in Cybersecurity Risk"

    • Clep Test

    • DSST

    • Excelsior College Examinations

    • Book: "Never split the difference on negotiating"

    • Threat Agent and Honeydocs

    • Intro Music: Cascadia by @Trash80

    • Outro Music: Coupe by @yungkartz


    Resources Mentioned:

    • The Paradox of Choice by Azeria Labs
    • Cyberseek Pathways

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    Jack Rhysider - From Odd-jobs to Network Analyst to SOC Architect to... Darknet Diaries! Jan 01, 2019
    Show notes

    With an engineering background, Jack found himself doing odd jobs at first. Looking to get back into tech, he certed up and got a job in the NOC (Network Operation Center) and eventually became a SOC architect building a SOC from scratch. Looking to do something different, he started Dark Net Diaries, and it's been an adventure since! This is Jack Rhysider's origin story.

    BIO

    Jack Rhysider started his professional career in a NOC. He then became a network security engineer doing a lot of work to harden the network and detect threats in the network. He became a security architect and successfully built a SOC for a MSSP. He's currently the host of the podcast Darknet Diaries, where he interviews hackers or those who've suffered a major attack. The podcast has experienced phenomenal growth, so Jack now works on it full time.

    Notes

    • A glimpse into the life of a security analyst and a Managed SOC

    • Takes about 3-6 months for an analyst to baseline and come up to speed

    • His first hack was hacking the Sim City savegame file. Dad was thrilled!

    • Several years of blogging his journey in Infosec helped Jack with his communication skills and explaining difficult concepts to people.


    Quotes:

    • "As a security engineer, I need to know a little bit about everything."

    • "I would do things like remove (rm -f /) the whole root directory just to see how many files I could delete before the whole operating system would crash!"

    • "Be fearless, grandma!"

    • "I think there is a lot of shaming that goes on if people... do security wrong... that kind of makes things stressful."

    • "I think what [we], as security people, lack sometimes is good communication."

    • "Taking on tasks when nobody asked them to take it on... is amazing!"

    • "I would keep corrupting files over and over, but eventually, I figured out which byte in the file was for the amount of money, and I was able to give myself a billion dollars!"


    Links:

    • Darknet Diaries Podcast
    • @JackRhysider
    • CFP Time
    • Intro Music by Trash80
    • Outro Music by Mid-Air Machine

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


    Yaron Levi - Entrepreneur to Security Architect to CISO and Security Champion Dec 25, 2018
    Show notes

    Yaron Levi is the CISO for Blue Cross and Blue Shield of Kansas City. We talk about what he looks for in people when hiring in Infosec and a time when he took a chance on someone (against the opinion of his peers), and his chance was a big success. We also discuss a breach he had to deal with only 3 months into his job!

    BIO

    Yaron Levi is the CISO for Blue Cross and Blue Shield of Kansas City (Blue KC). In this role, he manages a team responsible for information risk management, cyber defense, regulatory and compliance, architecture and engineering, and identity and access management for an organization that provides health insurance for about 1 million members and has over $2B in annual revenue.

    Prior to joining Blue KC, Yaron was a Director of Information Security for Cerner Corporation, an Information Security Business Partner for Intuit, an Information Security Architect and Product Manager for eBay, and a Director of Cloud Security for ANX.

    Yaron is a Research Fellow for the Cloud Security Alliance (CSA). The Research Fellow designation is the highest honor and distinction given to a CSA research volunteer who has demonstrated significant contributions to CSA research. Yaron is a co-chair and lead architect of the Cloud Enterprise Architecture. Contributor to the Consensus Assessments Initiative Questionnaire (CAIQ), Cloud Controls Matrix and promoted the CSA as best practice in various cloud projects with various Fortune 500 companies.

    Yaron is the co-founder of the Kansas City CISO forum, B-Sides Kansas City, and is a frequent speaker on Cyber Security Architecture, DevSecOps, and Cyber Defense.

    Yaron holds a B.A. in Social Sciences and Management and is a graduate from the FBI CISO Academy.

    Notes:

    • Created his own IT company to pay his way through college

    • A SOX Compliance project was his first exp

    • His first computer was a Sinclair ZX81

    • Had to save up to buy his own Commodore 64!

    • Yaron's discussion with youth whether a laptop is more dangerous than a gun? What about the 2nd Amendment?

    • 3-months into his job, he experienced a breach!


    Quotes:

    • "Security is one of those areas that you can be part of something that is bigger than yourself."

    • "Having a real calling for something... that can make a difference."

    • "It's one of those communities [where] people really want to help each other."

    • "I think, for many people, there isn't a prescription, if you will, of how and where to start."

    • "Are you the type of person who likes to crack codes and puzzles and bang your head against the wall for 16 hours...that may lead you to a dead-end or nothing? Oh no, I like to talk to people."

    • "First and foremost, we are educators."

    • "Sometimes, when we look for people, we tend to look for people based on a very specific mold or template [unfortunately]"

    • "Usually, I hire for character first, then skill."

    • "At the end of that record is a person... a human being."

    • "I think people need to realize that it can be a very thankless job, not just hoodies and hackers all day long. If you google a "Hacker" today... it's kind of depressing to everyone with hoodies like that... that's not the reality."

    • "It's all about defense... protection... enablement of the business securely. When everything goes well, nobody really thinks of you, nobody thanks you for that. But when something bad happens, everybody looks for a head to chop."

    • "It's, in my opinion, one of the more rewarding careers one could have and being part of something bigger than just themselves."


    Links:

    • Yaron Levi on Linked IN
    • Yaron on Twitter
    • Women in Security KC
    • BSides KC
    • Sec KC
    • Intro Music: Cascadia by Trash80
    • Outro: A Rising Wave - Jeremy Blake

    See omnystudio.com/listener for privacy information.

    Mentioned in this episode:

    Stay In Touch


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