DissedMedia: A Startup Story
DissedMedia: A Startup Story is a podcast that chronicles the start of DissedMedia and takes listeners along for the journey starting from the first week the company was founded. This podcast is about what a founder goes through trying to start a business and is meant to be a learning tool for anyone interested in starting a business of their own. Listen as founder Ben Olmos and his co-founding board work to take DissedMedia from concept to reality.
Episodes
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...
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 b...
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 succes...
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 • Courses that do not convert • Traffic that does not return • Content that does not c...
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.
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 Sta...
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 St...
Is your business one phishing email away from a devastating data breach? In this episode, cybersecurity expert and bestselling author Robert Siciliano breaks down exactly how today's hackers, scammers, and organized cybercriminals are targeting small businesses and what you can do right now to stop them.
What if you could run your entire podcast; recording, editing, repurposing, publishing, and monetizing, from one platform, for less than the cost of a single tool you're already paying for?
In this episode of DissedMedia: A Startup Story, Ben sits down with Nathan Gwilliam...
Most entrepreneurs don't think about legal protection until it's too late, and by then, it can cost them everything. In this episode of DissedMedia: A Startup Story, we sit down with Bobby Klinck, a Harvard Law graduate with over 20 years of legal experience, former federal prosecutor, and founder of the legal tech platform Plainly Legal, to break down...
With Dr. Tom DuFore | Big Sky Franchise Team
Franchising your business can unlock national expansion, recurring royalty revenue, and long-term brand growth. But it can also destroy your systems, culture, and reputation if done incorrectly.
In this episode, Dr. Tom DuFore explains what it really takes to build a successful franchise system and how founders can scale sust...
What happens after the startup exit?
In Episode 45, Kevin Rice shares the real story behind scaling a digital agency to 250 employees, navigating high-pressure Fortune 500 clients, surviving a COVID-driven restaurant tech pivot, and discovering that executive success doesn’t guarantee personal fulfillment.
After co-founding and exiting his consultancy, Kevin realized burnout, emotional disconnection, and “robot mode” had quietly ta...
What does it really take to build an entrepreneurial mindset, and how do you actually apply it when figuring out how to start a consulting business that generates real revenue? In this episode, April Palmer (aka Hot Mess Boss) breaks down the realities of startup growth strategy, revenue generation, consulting business models, customer discovery, and why most founders fail before they figure out how startups truly make money.
April...
Cash flow is the lifeblood of every business, and mismanaging it is one of the fastest ways founders lose control of their runway. In this episode of DissedMedia: A Startup Story, we sit down with Kunal Bhasin, CEO of 1West, to break down how smart founders approach small business financing options, non-dilutive funding, and cash flow management without giving up equity.
Kunal shares real-world insights on SBA loan requirements, SB...
What does it really take to achieve bootstrapped business growth, without venture capital, hype, or chasing every new marketing trend?
In this episode of DissedMedia: A Startup Story, Ben sits down with Lindsay Pinchuk, founder of Bump Club and Beyond, to break down how she built a community-first media business from scratch, scaled it to seven figures, and successfully exited, without outside funding.
Lindsay shares the real behin...
What if mediocrity isn’t your ceiling but a choice you’re unconsciously making?
In this powerful and deeply honest episode of DissedMedia: A Startup Story, host Ben sits down with Mark Dulaney to unpack the hard truths about ownership, urgency, discipline, and reinventing your life after failure.
After surviving cancer, financial setbacks, and decades of starting over, Mark reached a defini...
Struggling to fund your CPG business as you scale into major retailers like Walmart and Target? Emily Reeves, VP of Capital Solutions at Bridge Marketplace, reveals how consumer product founders can access working capital without giving up equity. In this episode, discover proven financing strategies including purchase order financing, invoice factorin...
Nearshoring can be the difference between a startup that crawls and a startup that ships. In Episode 39 of DissedMedia: A Startup Story, Ben Olmos sits down with Brian Samson, founder of Plug Technologies, to break down how founders and operators can scale teams in Latin America (especially Mexico and Argentina) to extend runway, move faster, and keep real-time collaboration with US time zones.
Brian shares how he went from US tale...
What if half the country could not safely eat at most restaurants and no one was talking about it?
In this episode of DissedMedia: A Startup Story, we sit down with Dylan McDonnell, founder of Foodini, to explore the future of food transparency, dietary safety, and why ingredient data is becoming a major competitive advantage for restaurants.
Diagnosed with celiac disease at age 10, Dylan left a successful career in corporate law t...
What does it really take to build companies that work consistently, predictably, and without leadership heroics? In Episode 37 of DissedMedia: A Startup Story, Ben talks with Chris Hallberg, an EOS Implementer (since 2014) and leadership coach known for his “Business Sergeant” approach to execution and accountability.
Chris breaks down how leadership teams can reduce confusion, tighten alignment, and create “one source of truth” fo...
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