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What does it mean to communicate clearly without losing kindness - or yourself? In this episode of Synching Up, Jake sits down with Jarryd Boyd, a senior communications leader and certified coach, to unpack the real power of clarity in work and life.
They explore why queer professionals often overexplain, how directness differs from harshness, and how simple frameworks like “clear is kind” can change your personal and working relationships, leadership style, and self-care practices.
With insights on conflict, coaching, emotional marketing, and generational communication shifts, this is a candid and practical conversation for anyone trying to be understood - and stay grounded.
Links and References:
In this episode of Synching Up, Jake sits down with Kai Wong (she/they), Principal of Digital Accessibility at Teladoc Health and contributing author to Inclusive Design for Accessibility. Together, they unpack what digital accessibility really means—beyond checklists and compliance—and how Kai’s lived experience as a neurodivergent, non-binary, queer AAPI professional fuels their advocacy.
From hiring with empathy to designing for inclusion, Kai shares why accessibility is essential to good UX, legal protection, and discoverability—and how embracing identity can be a superpower in the tech world. Plus, we talk about their book journey, the burnout realities of advocacy work, and the magic of weird friendships (shoutout to Pokémon Go!).
Whether you’re new to accessibility or deep in the work, this episode will leave you feeling empowered, seen, and inspired to do better by design.
Links and References:
Inclusive Design for Accessibility
AxeCon (free accessibility conference)
Kai Wong’s LinkedIn
Jake Tenenbaum’s LinkedIn
Out in Tech Virtual Community
Our Pokémon Go Trainer Codes
Kai: 752861053459
Jake: 200519292777
In this season two premiere of Synching Up, we sit down with Brendon Hawkins — a transdisciplinary artist and technical product manager working at the intersection of editorial, emerging technologies, and queer identity.
Brendon walks us through a deeply reflective timeline, from fashion photography to fine art to cybersecurity and product innovation. We explore how their identity as a Black, queer, American professional informs their creative approach to both art and tech — and how cycles of tension and transformation have guided their personal and professional pivots.
Along the way, we talk about showing up for community, the parallels between art critique and product management, and what it means to build with accountability in times of social and political unrest.
Episode links and references below:
Synching Up brings you conversations at the intersection of tech, identity, and innovation from Out in Tech NY.
Hosted by Jake Tenenbaum, each episode explores how technology shapes who we are, how we connect, and where we’re headed next.
Season 2 is sharper, shorter, and more focused — featuring conversations on marketing and leadership, clarity and communication, design and storytelling, building inclusive legal communities, creativity and career growth in the digital space, and so much more
Shorter episodes, deeper insights, all centered on how identity and innovation meet in today’s digital world.
Now streaming on Spotify, Apple Podcasts, Audible, Amazon Music, and Pocket Casts.
Annie Beckman’s journey spans volunteering in China, signal and space operations in the U.S. Army, and an upcoming chapter in law school - all grounded in an ethos of service. In this season finale, Annie reflects on leading a diverse array of teams as a junior officer, navigating identity in hierarchical institutions, and her passion for using technology to promote digital equity and effect change. Jake and Annie discuss space operations, mentorship, emotional intelligence, character both in and out of uniform, and how to make your life about more than just your job title.
If you’ve ever wondered how your values translate across sectors - or if leadership and impact are truly compatible - this one’s for you!
In this episode of Synching Up, Jake sits down with Jacob Gordon to explore what it truly means to have a life outside of work. From growing up in Iowa and entering the tech world during a global pandemic, to teaching group fitness classes and mastering skincare routines, Jacob shares how building a fulfilling “five-to-nine” identity has shaped his career, resilience, and sense of fulfillment.
Jacob is happy to connect with anyone who would like to dive deeper on any of the topics discussed. Connect with Jacob on LinkedIn or reach out to his personal training email if you're interested in a private fitness class, both of which can be found in the links below:
Links
What happens when a queer Indonesian lawyer gets laid off in New York and starts feeding strangers? You get Studio Bumi - a food experience studio on a mission to fight urban loneliness, one dinner party at a time. In this episode, Bagus joins Jake to talk about immigration, reinvention, and why fried rice might be the most honest metaphor for queer identity. Together they unpack what it means to go from tech law to sweat equity, build chosen family from scratch, and turn DMs into real-life community. It’s messy, moving, and deeply delicious - just like all good things.
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What does it take to build a startup - and a life - from a winding path of poetry, healthcare IT, Amazon grocery stores, and now fintech? In this episode of Synching Up, Jake sits down with Sara Schmitt, co-founder and COO of Adro, a neobank built for international students and newcomers to the U.S. banking system. Together, they unpack Sara’s “collage career” - from her early days as a poetry major to running medical records rollouts at Epic, launching Amazon Fresh during the 2020 pandemic, and co-founding a fintech startup grounded in purpose and accessibility. The two talk startup realities (fundraising, team equity, compliance), queer visibility in tech, the power of storytelling in career pivots, and why it’s okay not to found something in your twenties. If you’ve ever felt like your resume doesn’t follow the rules, this conversation is proof that a nonlinear path can still lead to the top.
Links
In this episode of Synching Up, we talk with longtime project management leader and Out in Tech member Michael Matute about building a career rooted in curiosity, queerness, and clear timelines. From launching a digital photo lab; to the dot-com boom; to coaching PMs today, Michael shares how LGBTQ+ identity, emotional intelligence, and the art of getting things done all converge in the project management world. We explore burnout, boundary-setting, mentorship, and why EQ might be the most underrated tool in your project toolkit.
Links from the show:
What does growing, adapting, and leading mean when your identity defies easy categorization? In this episode of Synching Up, we sit down with JD Valladares-Williams, an emotional intelligence consultant and storyteller who’s lived through civil unrest in Peru, self-discovery in Madrid, and creative breakthroughs on Broadway. Together, we explore how emotional intelligence, queer identity, and personal reinvention intersect with technology, learning, and leadership. From trauma and transformation to thriving in digital spaces, this conversation is a powerful reflection on resilience, empathy, and the frameworks that shape us.
Disclaimer: There were some audio issues while recording. We recognize them and continue to work on the audio tech. If you have any experience with audio and want to volunteer on this project, please do reach out (email below). A special shout-out and massive thank you to Rainbow Creative for helping us with the sound on this episode!
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