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.

What if your marketing has been speaking to the wrong customer all along? In this episode of DissedMedia: A Startup Story, founder Ben Olmos sits down with Amber Gaige, founder and chief marketing advisor at Far Beyond Marketing, to break down exactly why most small business marketing fails, and what to do about it.

Amber brings 20 years of marketing strategy experience, a background in private equity, a run as CMO and CIO overseeing 90 subsidiaries across 10 states, and a bestselling book that helps entrepreneurs stop wasting money on marketing that does not work. She also holds one of only a few hundred StoryBrand Guide certifications in the world.

In this episode you will learn the Four Cs of effective marketing (clear copy, consistent branding, customer demographics, and channel management), why video is no longer optional for small business growth, how AI is transforming what a lean marketing team can accomplish, what high buyer intent targeting is and why it may cut your sales cycle in half, why going viral is the lottery ticket version of a marketing strategy, how to speak the language your actual customer is using, and what happens when you stop doing a la carte marketing and start building a full system.

Whether you are a startup founder, solopreneur, franchisee, or small business owner who has ever burned money on marketing that went nowhere, this episode is built for you.

Connect with Amber Gaige: farbeyondmarketing.com | LinkedIn: Amber Gaige

Most people overlook raw land as a real estate investment. No utilities, no structures, no obvious appeal. Abi Asija saw something different. Starting with just $5,000, no debt, and a strategy most investors had never considered, Abi and his wife built a seven figure land business from the ground up, completing more than 700 deals across the United States over eight years.

In this episode of DissedMedia: A Startup Story, host Ben Olmos sits down with Abi to unpack the business principles, hard lessons, and unconventional strategies that turned desert parcels into a thriving operation. This conversation goes well beyond real estate. It is a masterclass in business fundamentals that applies to any entrepreneur at any stage.

What You Will Learn:

Abi breaks down the core formula at the heart of his book and his business: Money equals Goodwill times Number of Offers. It sounds simple. The way he applies it will change how you think about revenue, customer relationships, and growth.

Beyond the formula, this episode covers how to find and flip raw land for two to five times your investment, why the key to the land business is not buying but selling and how to do it online without a realtor, the real due diligence process for raw land including wetlands, arroyos, environmental contamination, easements, and soil testing, how Abi and his wife went from two deals on eBay to 700 plus properties sold, why customer lifetime value matters more than customer acquisition as your business scales, the show up rate problem in sales and creative ways to solve it, how to build goodwill in the marketplace through daily content and relationship building, and why Abi got rejected by business podcasts and started his own show instead.

About Abi Asija:

Abi Asija is a land investor, author, and founder of Honest Wealth Builders, a platform dedicated to helping people transition from a nine to five into entrepreneurship through land investing. Over eight years Abi and his team have completed more than 700 land deals across the United States and built a seven figure business without taking on debt. He is also the host of the Honest Wealth Builders podcast, where he sits down with active business owners to discuss real time strategy and problem solving.

Abi's Book: The Land Business by Abi Asija is available on Amazon.

Connect With Abi Asija and Honest Wealth Builders:

YouTube: https://www.youtube.com/@HonestWealthBuilders

LinkedIn: Search Abi Asija

Website and Free Resources: Search Honest Wealth Builders

Connect With Ben Olmos and DissedMedia:

Website: https://www.dissedmedia.com

Daily Pitch News: https://www.dailypitch.news

Ben's Book: 10 Topics to Help Managers, Leaders and Entrepreneurs Get Better at What They Do, available at https://shop.dailypitch.news and on Amazon and Barnes and Noble

Ben's Personal Site: https://www.benolmos.com

DissedMedia: A Startup Story is the podcast that takes you behind the scenes of building a media company from the ground up. No outside funding, no shortcuts, no overnight success. Just real conversations with real entrepreneurs about what it actually takes to build something from nothing. Subscribe wherever you listen to podcasts and help us reach 100,000 YouTube subscribers in 2026.

The audiobook industry just crossed $2 billion in U.S. revenue and is projected to double. So why are most entrepreneurs, coaches, authors, and podcast hosts still sleeping on it?

In this episode, Ben Olmos sits down with Tina Dietz, CEO and founder of Twin Flames Studios, one of the most respected audiobook production companies in the world. With over 500 audiobooks produced, a pioneering remote narration model, and more than a decade at the forefront of audio publishing, Tina breaks down everything entrepreneurs and independent authors need to know about turning their expertise into audio.

Whether you are a first-time author, an established podcast host sitting on years of untapped content, or a business owner trying to build a brand that outlasts the algorithm, this conversation is for you.

What You Will Learn:

Who Should Listen:

This episode is essential listening for entrepreneurs, managers, leaders, authors, coaches, consultants, course creators, and podcast hosts who want to expand their reach, build credibility, and create lasting content assets. If you have a book idea, a manuscript collecting dust, or years of podcast episodes that have never been monetized, Tina explains exactly how to put that content to work.

About Tina Dietz:

Tina Dietz is the CEO and founder of Twin Flames Studios, an award-winning audiobook and audio publishing company that has produced more than 500 titles across fiction, nonfiction, and multi-voice formats. She is a pioneer in remote author-narrated audiobook production and the creator of Voice Powered Publishing, a framework that helps experts and thought leaders build books from their existing podcast content. You can connect with Tina and access free monthly events for authors at TwinFlamesStudios.com.

DissedMedia: A Startup Story is the podcast that takes you behind the scenes of building a media company from the ground up. No hype. No overnight success stories. Just real conversations with real entrepreneurs about what it actually takes to grow something from nothing.

Subscribe, leave a review, and share this episode with a fellow entrepreneur who is ready to stop ignoring audio.