The Future Of The Future

Today on The Future of the Future, we sat down with someone who’s been at the center of Charleston’s growing tech scene and has spent the last decade connecting some of the most innovative minds in the Southeast: Stanfield Gray.Stanfield is the founder and force behind DigSouth, the premier tech summit and media platform showcasing what's next in technology, business, and culture across the South. From launching the first editions of DigSouth to bringing major tech leaders to Charleston, Stanfield has built something bigger than just an event—he’s helped shape a regional movement.In this conversation, we unpack his journey: how he got started in the tech world, what inspired him to create DigSouth, and how the landscape has evolved—especially through the COVID era. We’ll dive into his playbook for attracting big names to Charleston, his perspective on networking in a digital-first world, and what he sees coming next for the Southeast’s innovation economy.And of course, we’ll take a step back to learn more about the person behind it all—his lessons as an entrepreneur, his vision for the future, and what keeps him grounded when he’s not working.If you’re curious about building communities, driving innovation outside of Silicon Valley, or just want to hear a great story from someone at the intersection of tech, media, and the South—this one’s for you.Let 's get into it.

I've been deeply immersed in the technology world for the last 5 years of my career.I am not an engineer myself, but I work with engineers daily, and I've interviewed quite a few technology leaders to learn more about their story and their path in this industry.I always learn something new. Most stories are not a simple straight line. There is a beginning, a spark, there's lots of hard work, there are opportunities and paths taken, decisions, there are mentors, there are lessons learned, discoveries by chance and preparation alike.Today, we will dive deep into the story of Jeff Bridwell, a seasoned technologist and software engineering leader with over three decades of experience building systems and leading high-performing teams across fintech, ecommerce, and supply chain. Jeff is not only passionate about the craft of engineering, but also about growing people, fostering clarity, and making systems work for real-world impact.In this episode, we explore Jeff’s journey into tech, his leadership philosophy, what he values in team members and how to foster high performing teams, how technology has evolved since he got started, and what he sees coming next. We’ll also touch on what keeps him grounded outside of work.Whether you’re an engineer, a leader, or just someone thinking about the future of tech and teams, this conversation is packed with practical insights and thoughtful reflections.Enjoy!

Today, we’re diving into a space that affects every product we use, every service we interact with, and, whether we realize it or not, every decision we make as consumers: customer experience and user experience, or CX and UX.Joining me is Dante Vono, a seasoned leader in the CX/UX space with a unique background that bridges business strategy, design thinking, and emerging technologies. With a career that spans pivotal roles in both consulting and in-house innovation teams, Dante has spent years helping companies rethink how they engage with customers, from first interaction to long-term loyalty.In this episode, we’ll talk about:- what CX and UX actually mean in practice, - why they’re more critical than ever, - how the field has evolved over the past two decades, and where it’s headed next. Dante will also share personal milestones from his career journey, offer advice to those breaking into the field, and, on a lighter note, what he enjoys when he’s not shaping the future of digital experiences.Enjoy!

People are, especially for services companies, the most important asset for a business.Building the right culture, so the right people want to stay and contribute, is key to success.Easier said than done in today's world of remote work and uncertainty.What are the keys to understanding and building the culture you need?Joining me today, is Alice Yoo LeClair, Senior Vice President and Head of Talent, Culture & Performance at Ascendion — a global leader in digital engineering and talent orchestration.Alice has spearheaded Ascendion’s efforts in aligning human capital strategy with business goals, ultimately transforming the way organizations build and scale digital products. She leads thousands of people working remotely across the world.  In our conversation today, we’ll explore:Ascendion’s mission—how they help enterprises tackle digital transformation and talent challenges. Alice’s journey—her career path, leadership philosophy, and what energizes her in this work. Alice’s thoughts on building strong, inclusive tech cultures—especially in remote and hybrid environments. Whether you care about DEI, remote work, or human-centered leadership in tech—this episode is you.Enjoy!

He was an entrepreneur. He was travelling across the US raising funds for a non profit org building houses for the unhoused.But, wherever he went, he carried his guitar with him. Music was always his anchor.Late into his twenties, he made a pivotal decision. He gave it all up, and found a way to enrol in Berklee, to study music and follow his passion.How did a successful and young Uruguayan entrepreneur pivot from Business and Entrepreneurship into Music?How did his background help him and inform the way he thought and go about playing or composing music?This is the story of Nacho Gonzalez Nappa, an award winning film and video game music composer. Nacho is a very, very talented musician. But I would venture to say he is also a great philosopher and a humanist.In a world where technology advances drastically by the minute, and the cost and time to “create” new things is reduced to mind numbing levels, Nacho’s call for doubling down on our own aesthetic lens, our very own point of view of the world and the magic within, is refreshing, compelling, and timely.I could listen to this one a million times, and always find new golden nuggets. Go for it. Enjoy.

How is AI impacting the world of Education? What Opportunities exist and how are they being leveraged today? What risks exist? How do we overcome these risks?These are just a few of the topics we talked about in this episode, with Joon Nak Choi, a.k.a. JC, Adjunct Professor at HKUST Business School, and Founder at Learnovate,  an edtech startup focusing on making AI useful for educators.JC is the mastermind behind pregrade, an easy-to-use AI grading assistant that allows educators to efficiently grade an entire batch of essays simultaneously using their own rubrics, delivering personalized feedback for each student, while always keeping a human in the loop that maintains accountability and appropriateness in the final evaluation.You don’t want to miss this one. Enjoy!

Today we’re diving deep into a topic that touches every growing company: recruitment. More specifically, how we find, attract, and retain great talent in a world that’s constantly shifting.Joining me is Ali Sichel, founder of Fox Talent Solutions, a company that’s not just filling roles, but helping organizations build smarter, more strategic hiring engines. Ali’s journey through the world of recruitment is as inspiring as it is insightful. She’s helped shape teams at high-growth startups and understands both the art and the science of connecting companies with the right people.In this episode, we’ll explore:Ali’s path into the recruiting world, and the pivotal moments that shaped her approachWhy she founded Fox Talent Solutions, and what gap in the market she sawHow her team blends customized search with internal tooling to empower clientsThe trends shaping the future of hiring, from AI and automation to cultural shifts in how people view workAnd what she sees on the horizon for both recruiters and the organizations they supportWhether you're building a team, navigating the job market, or just curious about how the recruiting landscape is evolving; this episode is packed with wisdom and forward-looking insights.Let’s jump in. Here’s my conversation with Ali Sichel.

Today, we're diving into a space that impacts nearly every one of us, whether we rent, own, invest, or simply live: real estate.Joining me is Inaas Arabi, the Chief Operating Officer at Block, a fast-growing property management company that's not just managing real estate assets—but reimagining the systems behind them. From centralizing complex operations to integrating AI-driven solutions, Inaas is helping transform how property management works at scale, and how it feels to those who depend on it.In this conversation, we’ll unpack:How Block is redefining what operational excellence looks like in real estateWhy the industry has lagged in tech adoption—and what’s changing nowThe future of ERPs, AI, smart buildings, and even VR in housingAnd why human connection still matters most, even in a tech-powered worldWe’ll also talk about Inaas’s personal journey—from building systems and leading change, to how he stays inspired outside the office.This episode is for anyone fascinated by the convergence of technology, operations, and real human impact. Whether you're in PropTech, managing properties, or just curious about where your rent check is heading—this one’s for you.Let’s get into it. Here’s my conversation with Inaas Arabi.

What does it take to navigate the evolving landscapes of technology and leadership? How can systems guide us through complexity?Today, we're joined by Kevin Henrikson—a technologist, entrepreneur, and pilot. From co-founding Acompli, which was acquired by Microsoft and became Outlook Mobile, to leading engineering teams at Microsoft and Instacart, Kevin has been at the forefront of building and scaling impactful technology. In this conversation, we'll unpack Kevin's journey through startups and big tech, discuss the importance of systems in scaling teams, examine the evolving landscape of AI and the future of work, and uncover how his experience as a pilot informs his approach to leadership and innovation.Enjoy!

Today, we’re going to talk about small and mid-sized businesses—and the transformative role AI should be playing in their future.You’ve probably heard about generative models, language agents, and enterprise AI stacks—but what about the bakery, the logistics firm, or the family-run manufacturer? Why are these businesses so often left out of the AI revolution? And more importantly, what can be done about it?Our guest is Justin Massa, a seasoned technologist, product thinker, and founder who’s now laser-focused on bridging the gap between cutting-edge AI and the everyday companies that need it most.Justin is the founder of Midwest Quality Consulting, where he advises SMBs on how to thrive with generative AI. He also publishes the newsletter AI for SMBs, sharing insights and practical guidance for small businesses looking to leverage AI technologies .In this episode, Justin will unpack the gap between what AI can do and what most SMBs are actually using it for— and share his vision for democratizing access to powerful tools, rethinking design roles in the age of AI, and training the next generation of AI-native leaders.Let’s get into it.