What happens when a former CIO with a decade of AI experience sits down to have an unfiltered conversation about where artificial intelligence is really headed? You get this episode.

Stephanie Sylvestre is the founder and CEO of Avatar Buddy, an AI company she started building in 2016 before most people had heard the term machine learning. A former Chief Information Officer and Chief Programs Officer, Stephanie brings rare technical depth and real-world business experience to every conversation about AI. She has presented at universities across the Caribbean, built AI solutions for enterprise clients who could not otherwise afford robust technology, and pioneered a framework she calls the Human Digital Handshake, which centers AI development around making people more effective rather than replacing them.

In this episode of DissedMedia: A Startup Story, Stephanie joins host Ben Olmos for a frank, thought-provoking conversation about the promise and the very real danger of the current AI moment. She explains why she refuses to build agentic AI solutions for clients, breaks down the security nightmare that root access creates for everyday business owners experimenting with AI agents, and makes a compelling case that creativity and intellectual curiosity, not prompt engineering, are the skills that will separate the winners from the losers in the AI era.

Stephanie also shares the work that gets her out of bed every morning: using AI to preserve endangered indigenous languages in Belize including Creole, Yucatec Mayan, and Garifuna, deploying AI to help farmers in Ghana improve crop yields, and building digital twins that allow everyday people to preserve their personal legacies for future generations. This is AI being used the way it should be used.

Topics covered in this episode include agentic AI risks and security vulnerabilities, the Human Digital Handshake framework, digital twins for legacy preservation, indigenous language preservation using AI, AI productivity for small and mid-sized businesses, why teenagers are Stephanie's secret weapon in product development, AI ethics and responsible deployment, and how to think about AI as a strategic thinking partner rather than a search engine.

Connect with Stephanie Sylvestre and learn more about Avatar Buddy:

Website: avatarbuddy.ai LinkedIn: linkedin.com/in/stephaniesylvestre Mention DissedMedia when you reach out and Stephanie will personally offer you a complimentary 30-minute consultation.

Subscribe to DissedMedia: A Startup Story on YouTube and help Ben reach 100,000 subscribers in 2026: youtube.com/@TheDailyPitchNews

Pick up Ben's book, 10 Topics to Help Managers, Leaders and Entrepreneurs Get Better at What They Do, at benolmos.com, on Amazon, and at Barnes and Noble.

Most entrepreneurs start a business chasing freedom. What they get instead is a job they can't quit, a team that can't move without them, and a calendar that owns every hour of their life. David Salerno built a packaging solutions company from zero to eight figures with fewer than 20 people, and then walked away. Not because he burned out. Because he built it right.

In this episode of DissedMedia: A Startup Story, Ben Olmos sits down with David Salerno, entrepreneur, author, Forbes Business Council member, and Vice Chair of the Montreal Economic Institute, to break down exactly how founders can stop being the bottleneck in their own business and start building something that runs without them.

David shares the Sherpa Method, his proven three-challenge framework for growing a business built on freedom, not dependency. If you are a founder, operator, or entrepreneur who feels trapped in the day-to-day grind of your own company, this episode will change how you think about growth, delegation, and what it actually means to lead.

In this episode you will learn:

How David scaled from $80K in year one to an eight-figure exit with a lean team of under 20 people

Why growth without systems creates a trap, not a business

The difference between delegating and abdicating, and why most founders get it wrong

How to identify when you have become the bottleneck in your own company

The three core challenges every entrepreneur must master: Growth, Sustainability, and Service

Why your best early hire may become your biggest scaling obstacle

How the Sherpa Method creates business freedom without sacrificing momentum

The mindset shift that unlocks the next level of revenue growth

Why trust but verify is the management mantra that actually works

How to build a team culture where people own their sandbox and thrive in it

About David Salerno

David Salerno is the founder of Entrepreneur Sherpa, author of Built for Freedom, Vice Chair of the Montreal Economic Institute, and a Forbes Business Council member. He scaled Solo Pack Packaging Solutions from a solo startup to an eight-figure business before exiting, and now helps entrepreneurs build companies designed for freedom, not dependency.

Get David's book: Built for Freedom — https://amzn.to/4cCLGJv 

Visit David's website: https://www.davidsalerno.com

Connect with David on LinkedIn: https://www.linkedin.com/in/davidvsalerno/ 

About DissedMedia: A Startup Story

DissedMedia: A Startup Story is the podcast that takes you behind the scenes of building a business from the ground up, the wins, the walls, and everything in between. Hosted by Dr. Ben Olmos, analyst, entrepreneur, author, and educator.

We are on a mission to hit 100,000 YouTube subscribers by the end of 2026, and we need your help to get there. If this episode delivered value, subscribe to our YouTube channel and bring a friend along for the ride.

Subscribe on YouTube: https://www.youtube.com/@DissedMedia

What happens when your startup faces a crisis and you have no plan? In Episode 60 of DissedMedia: A Startup Story, Ben Olmos sits down with Joshua Altman, Fractional Chief Communications Officer and founder of Beltway Media, to break down crisis communications strategy for startups and small businesses. Joshua shares the three-tier framework every founder needs — story, narrative, and brand architecture, and explains why most companies start thinking about communications too late. From managing investor messaging during a rough quarter to knowing when to respond to a rumor versus letting it die, this episode delivers a practical, real-world playbook for protecting your brand reputation before a crisis hits.

Joshua draws on his background as a multimedia journalist covering Congress for The Hill newspaper to explain how storytelling and technical production skills combine to shape perception and build trust. Founders will walk away understanding the difference between founder panic and a real crisis, how to build a communications drill before you need one, and why authenticity in content is harder, and more important, than most people think.

Whether you are pre-launch or scaling fast, this episode is essential listening for any entrepreneur who wants to communicate with confidence when it matters most.

Connect with Joshua Altman:

Website: beltway.media

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/joshuaialtman/

Free startup tools and self-assessments: beltway.media

Connect with Ben Olmos: Website: benolmos.com

Book — 10 Topics to Help Managers, Leaders & Entrepreneurs Get Better at What They Do: benolmos.com

The Daily Pitch: dailypitch.news LinkedIn: linkedin.com/in/benolmos

What happens when a Wall Street veteran bootstraps a Kickstarter campaign into a seven-figure e-commerce business and then turns around to help other founders do the same? In Episode 59, Ben sits down with Nate Littlewood, founder of Future Ready CFO, to unpack the financial truths most founders learn too late. Nate shares how he grew Urban Leaf from a crowdfunded idea into a thriving CPG brand, why most physical products businesses are quietly bleeding cash, and what a fractional CFO actually does versus what founders think they do. The conversation goes deep on cash conversion cycles, performance-based agency agreements, the brutal economics of CPG distribution, and how AI is reshaping the future of financial advisory. If you are running a product-based business and wondering where all the money went, this episode is for you.

Links Mentioned in This Episode

Guest: Nate Littlewood

Connect with Ben Olmos and DissedMedia

What happens when algorithms replace editors and social media becomes America's newsroom? In this episode of DissedMedia: A Startup Story, host Ben Olmos sits down with Julian Baron, Managing Editor of Off The Press and Baltimore Sun contributor, to tackle one of the most urgent challenges facing managers, leaders, and entrepreneurs today: how do you build trust in a world where the information your team, your customers, and your market relies on is being filtered through an algorithm designed to keep people addicted, not informed?

Julian brings frontline experience from inside the media industry to break down why 2025 marked the first time a majority of Americans named social media as their primary news source, what that shift means for businesses trying to communicate credibly, and why the collapse of local news is happening faster than most people realize. He also explains how Off The Press is building a lean, donor-funded, algorithm-aware media operation designed to fill the void before the bottom drops out of legacy journalism entirely.

In this episode you will learn why the social media algorithm is not a neutral tool, it is a business model built on engagement over accuracy; how platforms like TikTok, Instagram, and Facebook have deprioritized links to lock users inside their ecosystems; why television news is being quietly subsidized by sports broadcasting and what happens when the NFL fully moves to streaming; how Canada's experience with Meta pulling news from its platforms is a preview of what could happen in the U.S.; and what responsible journalism built for the social media era actually looks like in practice.

Whether you lead a team, run a company, or simply want to be a more informed decision-maker, this conversation will change how you think about the news you consume and the sources you trust.

Follow Julian Baron on X at https://x.com/JulianTBaron and explore Off The Press at https://www.offthepress.com

Subscribe to DissedMedia: A Startup Story on YouTube and help us reach 100,000 subscribers at https://www.youtube.com/@TheDailyPitchNews

Most business owners know they need to show up on social media. The problem? They don't know where to start, they're afraid of the camera, and they don't have time to create content every day. Aaron Witnish has built a career solving exactly that problem.

Aaron is a content strategist and agency owner based in Australia who has been helping business owners build their online presence since 2012. In this episode, he breaks down his signature 30 Days of Content in 30 Minutes system — a framework that turns a single conversation into a full month of social media posts, reels, and video clips using AI tools anyone can access today.

In this conversation, Aaron and Ben dig into what it really takes to get comfortable on camera, why giving away your best content for free is the smartest business strategy, and how AI is changing the content game without replacing the human element that actually builds trust with buyers.

What you'll learn in this episode:

Connect with Aaron Witnish: aaronwitnish.com

DissedMedia: A Startup Story is the podcast that takes you behind the scenes of building a business from the ground up. New episodes drop regularly on The Daily Pitch. Subscribe and follow along at dailypitch.news.

What does it actually take to walk away from a career that looks successful on paper and build something that feels purposeful? Chanda Coston knows that moment well, and she has made it her mission to help other women navigate it.

Chanda is a business strategist, certified Project Management Professional, and Six Sigma Black Belt who spent a decade in the military before moving through corporate consulting, government contracting, and entrepreneurship. After losing her brother to gun violence in 2018, she founded the HEB Foundation, a nonprofit serving families affected by gun violence in the Hampton Roads area of Virginia. It was in that work that she discovered her true calling: coaching women around the age of 40 to build businesses that are sustainable, purposeful, and designed around their lives rather than the other way around.

In this episode, Chanda and host Ben Olmos get into the real reasons entrepreneurs burn out, why structure is actually the path to freedom, how to stop building another job for yourself, and what it means to give yourself permission to work differently.

If you have ever felt overwhelmed running your own business, wondered whether the grind is supposed to feel this hard, or found yourself asking what comes next, this conversation is for you.

Connect with Chanda at chanda-co.com and on social media at @cchanda__co. Learn more about the HEB Foundation at thehebfoundation.org.

What if the fastest path to generational wealth is not launching a startup, but acquiring one?

In this episode, Tyrus Shivers breaks down entrepreneurship through acquisition and why serious founders must master capital raising, business systems, and long-term strategy if they want to build real enterprise value.

We explore how to design a business operating system that creates a scalable business model, attracts investors, and positions a company for the IPO process. Tyrus shares how he transitioned from Air Force veteran to founder of Legacy Wealth Capital Group, building an ecosystem focused on business acquisitions, regulation crowdfunding, Reg CF opportunities, and strategic growth.

Inside this conversation:

• Why capital raising is a core leadership skill

• How business acquisitions accelerate small business growth

• The opportunity inside small cap stocks and private companies

• What founders misunderstand about wealth management strategies

• How digital entrepreneurship and content monetization fit into equity strategy

• The difference between operating a business and building an asset

If you are focused on raising capital for startups, structuring your company for scale, or building generational wealth through ownership, this episode delivers practical insight grounded in real execution.

Learn more about Tyrus Shivers:

https://tyrusshivers.com/

https://legacywealthcapitalgroup.com/our-story

Watch full episodes and exclusive content on YouTube:

https://www.youtube.com/@TheDailyPitchNews

We are on a mission to reach 100,000 subscribers in 2026. If you believe in serious conversations about entrepreneurship, capital strategy, and building scalable companies, subscribe and share the channel.

Subscribe to the podcast for more episodes on entrepreneurship through acquisition, capital raising, business systems, and building businesses designed to last.

What does it take to walk away from a six-figure income, start over from scratch, and build a thriving ad agency from nothing? In this episode of DissedMedia: A Startup Story, Ben Olmos sits down with Jeremy Yang, a paid media expert, agency owner, and one of the sharpest minds in digital advertising, to unpack the real journey behind building a successful marketing business.

Jeremy's story is unlike most. At 36, after years running a franchise business, he went back to university as a mature-age student, graduated at the top of his class, and still couldn't land a job. What followed was a full year of unpaid internship work, updating WordPress sites and manually transcribing YouTube videos, before he found his calling in paid advertising and media buying.

In this episode you'll learn:

Whether you're a startup founder, a small business owner trying to crack social media marketing, or an aspiring entrepreneur looking for a real-world roadmap, this episode delivers the kind of hard-won insight you won't find in a textbook.

Website: https://digitalgoliath.com.au

LinkedIn: https://www.linkedin.com/in/jeremy-yang/

Topics covered: paid media, media buying, digital advertising, Facebook ads, startup growth, social media marketing, entrepreneurship, agency building, immigrant entrepreneur, career pivot, marketing strategy, ad spend ROI, organic vs paid social

If this episode gave you something to think about, drop a comment and let us know your biggest takeaway. We read every single one. And if you haven't subscribed yet, we are on a mission to hit 100,000 subscribers on YouTube in 2026 and we would love your help getting there.

Subscribe to The Daily Pitch on YouTube here: https://www.youtube.com/@thedailypitchnews and join a growing community of entrepreneurs, founders, and builders doing the work every day.

Connect with DissedMedia: Website: www.dissedmedia.com | Newsletter: www.dailypitch.news | YouTube: The Daily Pitch

DissedMedia: A Startup Story is the podcast that takes you behind the scenes of building a business from the ground up, raw, real, and unfiltered.

What do you do when the content is good… but the growth is not there?

In this raw update, I break down the strategic pivot that is reshaping DissedMedia from a blog-first platform into a video-driven business engine.

This episode is for founders, operators, coaches, and creators who are wrestling with:

• Organic growth that feels too slow

After attending a media event in Atlanta, one question stopped me cold:

“What are you actually selling?”

At the time, I did not have a good answer.

So we rebuilt the model.

Inside this episode, I walk through:

We are currently at 17,000+ subscribers and pushing toward 100,000 by the end of 2026.

This is not theory.

If you are building a business in public…

This episode will challenge how you think about media, leverage, and growth.

Listen in and see how we are turning a passion project into a scalable platform.