DissedMedia: A Startup Story
by DissedMedia
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
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#112 Nicky Billou: Selling as Service, Not a Dirty Word
Nicky Billou, co-founder of eCircle Academy, joins Ben Olmos to talk about how he built a career coaching entrepreneurs on sales and mastermind dinners after an extraordinary childhood escape from revolutionary Iran. The conversation moves from his father's example of radical generosity, to the...
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#111 Bart Merrell on Losing a Leg and Building an Income Stream in Six Months
Bart Merrell built his career around a single question he asks whenever life hands him something, good or bad: can this be monetized? In this conversation he traces that mindset from a teenage DJ business in rural New Mexico through bungee tower contracting in Japan, an accidental dog training...
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#110 Debora Prossomariti: Executive Personal Branding and Building CEO Authority on LinkedIn
For founders and senior leaders who carry a great deal of authority inside their companies, yet have seemingly never given much thought to how they are perceived in public, executive personal branding can feel like a chore that sits somewhere between marketing and self-promotion, and it is often...
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#109 Joshua Griffin: Recovering from Startup Burnout and Business Debt
Startup burnout may be among the least discussed costs of building a business, and for Joshua Griffin it arrived after years of sixteen-hour days spent propping up an e-commerce brand whose loans sat in his own name, eventually leaving him with roughly £35,000 in business debt and a physical...
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#3 Getting Fired, Getting Hired, Getting Tired: AI Layoffs and the 2026 Job Market
Layoffs that seemingly keep coming, along with hiring systems that may reject an applicant before any person reads a resume, have left a great many professionals wondering where the next job actually comes from, and in the third episode of Better @ What You Do, host Ben Olmos brings back three...
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#108 Ted Wolf: How AI Agents for Business Boost Valuation Before You Sell
When an owner has spent decades building a company, it may come as a surprise that buyers weigh whether the business can run without its founder more heavily than the profits it reports, and that question of transferability is quickly becoming tied to how well a company puts AI agents for…
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#107 Ric Thompson on Temporal Intelligence and Knowing How You’re Built
Ben Olmos has long described himself as a natural skeptic, someone whose doctoral training taught him to trust data and observation before anything else, so when Ric Thompson, co-founder of Temporal Intelligence, offered to read him live on the show using nothing more than his name and his birth...
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#106 Brett Schklar: AI Adoption Strategy and the Real ROI of AI for Business Leaders
Most business leaders have run an AI pilot or two by now, yet it is believed that relatively few have stopped to ask what the AI they are already paying for genuinely returns to the business, and that accounting question sits at the center of this conversation on AI adoption strategy and AI ROI...
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#105 Ben Albert: Business Networking Tips for Introverts Who Dread Small Talk
Business networking can feel out of reach for founders who are shy or worn down by small talk, and Ben Albert built his business by finding another way in. Furloughed from a corporate sales role in 2020, the Rochester, New York marketer began messaging fellow college alumni on LinkedIn and…
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B@WYD #2 Who Holds the Scorecard? AI at Work and the Metrics That Still Matter
In this episode of Better @ What You Do, host Ben Olmos brings back three former guests of DissedMedia: A Startup Story to work through a question that has seemingly crept up on most operators in recent weeks, which is what remains worth measuring once somebody else holds the scorecard. The...
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#104 From Pastor to Craft Distillery Founder: Matt Estrin of 477 Distilling
Matt Estrin spent fifteen years as a music pastor before an anniversary trip to Napa Valley sent him home with a five-gallon stovetop still and a plan to start a craft distillery, and nine years later he is the founder of 477 Distilling in Greeley, Colorado, with craft spirits distributed across...
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#103 Josh Rosenberg: How to Scale a Business With People, Process, and Technology
How to scale a business is the question at the center of this conversation with Josh Rosenberg, founder of Forward Thinkers and former chairman and CEO of Accent Food Services. Josh spent eighteen years inside a global beverage company, beginning as a driver merchandiser and rising into national...
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#102 David Leibner From Restaurateur to App Founder: The Spotify of Where to Eat and Drink
Most couples, and seemingly most groups of friends, have spent far longer than they would care to admit debating where to eat, scrolling through map results that know very little about what they actually enjoy. In this episode of DissedMedia: A Startup Story, host Dr. Ben Olmos sits down with…
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#101 Daniel Alfon: Why Fewer LinkedIn Connections Mean More Referrals
Daniel Alfon has been on LinkedIn since February 2004, long enough to have made every mistake the platform allows and to have built a method that runs against most of the advice circulating about it today. In this conversation, Daniel makes the case that a smaller, well-chosen network outperforms…
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B@WYD #1 Grit in the Age of AI: What Leaders Can Learn from Meta's Settlement and YouTube Monetization
Welcome to the first episode of a new show from DissedMedia; Better @ What You Do In this first episode of Better at What You Do, host Ben Olmos and four returning guests from DissedMedia: A Startup Story explore what that shift means for leaders by way of the Meta social media addiction…
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100 Episodes: From Cold Calls to Cash Flow
A hundred episodes into DissedMedia: A Startup Story, I step away from the usual guest interview to give an update on how the show and the company behind it got here, beginning with thanks to my advisory board and to former co-host Alan Landry, and moving into the PodFest event in Atlanta that, a...
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#99 Lady Jen Du Plessis: How to Monetize a Podcast Through Guesting and Networking
Lady Jen Du Plessis holds every one of her five shows to a six-figure revenue standard, and in this conversation she walks Ben through the mechanics behind that number, which center upon what happens after the recording stops rather than inside the episode itself. She spent four decades in...
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#98 Rob Broadhead: AI Implementation Starts With Business Process Improvement
Leadership teams across nearly every industry are moving quickly on AI implementation, and while the tools and models seemingly perform well, many rollouts stall at the handoffs and decision points that nobody took ownership of beforehand. Those gaps tend to surface the moment the technology…
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#97 Jaden Sterling: How to Pick Stocks and Build Wealth on Your Own
Anyone trying to work out how to pick stocks on their own, without turning the whole portfolio over to a brokerage firm, tends to hit the same wall, which is that the language of Wall Street can seem designed to keep ordinary investors confused and dependent upon the people selling them products....
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#96 Willie Blake: How to Overcome Analysis Paralysis and Build a Business Around the Way You Think
Willie Blake built WB Coaching around a premise that runs against most of the discipline and productivity advice sold to entrepreneurs, namely that a brain which does not process information in a straight line needs a different operating system rather than a harder version of the same one, and on...
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#95 Josh Elledge: Podcast Guesting as a Revenue Strategy, and Why Most Pitches Get Deleted
Podcast guesting has become one of the most crowded channels in B2B marketing, and Josh Elledge, founder of PodVerified and host of The Thoughtful Entrepreneur, fields somewhere between 400 and 500 spam pitches every month for his own show, which may explain why so many would-be guests feel like...
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#94 Patrick van der Burght on Ethical Persuasion
Most professionals build their pitch for the part of the brain that decides almost nothing, and Patrick van der Burght has spent two decades explaining why that habit quietly costs them business; in this episode he walks through the science of how people actually arrive at yes, drawing on the…
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#93 Walt Thiessen: How Vibe Coding Breaks at Scale and How AI Gather Fixes It
Most software built by prompting AI, what people now call vibe coding, works well enough to impress in a demo, yet it tends to buckle the moment real complexity enters the picture, and Walt Thiessen has spent the better part of two years chasing down why that happens and what actually fixes it....
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#92 Per Sjofors: Pricing Strategy Secrets From The Price Whisperer
Per Sjofors, known as The Price Whisperer, built his career on the idea that pricing strategy is the real lever separating profitable companies from struggling ones, more than product or marketing alone. In this episode, Per explains why pricing gets barely a page and a half in most business…
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#91 AI for Real Estate Agents: Sheldon Wolf on Intellitary's "Un-Brokerage" Model
Sheldon Wolf is the founder of Intellitary, a real estate lead generation platform built to solve one problem: most brokerages don't have enough qualified transactions coming in. After 30 years in real estate and finance, Sheldon built Intellitary's AI system to screen and qualify buyers and...
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#90 Kenneth Kollasch: How to Grow a Small Business With Trust, Systems, and Leadership
Kenneth Kollasch, a third-generation entrepreneur and certified business coach who spent fourteen years running a century-old franchise, joins Ben to talk about how to grow a small business through the exact transition that separates a mom-and-pop operation from a company that actually runs…
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#89 Kelly Schuknecht: How to Build a Personal Brand and Become a Thought Leader
Kelly Schuknecht spent a decade in publishing helping authors figure out what actually happens after a book hits shelves, then spent seven years growing an accounting firm's marketing department from four million to twelve million in revenue, and it was only after a layoff eliminated her role…
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#88 Matthew Slaymaker: Performance Marketing Psychology and the AI Ad Backlash
Most performance marketing fails long before a single dollar reaches an ad platform, and this conversation with Matthew Slaymaker centers upon that idea from the very first question. Slaymaker, founder of Slaymaker Marketing, has spent his career helping B2B brands and e-commerce companies build...
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#87 Kurt Uhlir: Servant Leadership and the Discipline of Scaling Past Activity
Kurt Uhlir has spent a career watching companies confuse activity with progress, and on this episode of Dissed Media he sits down with Ben Olmos to explain what servant leadership actually looks like once a company moves past the idea stage and into the hard, unglamorous work of scaling. Uhlir...
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#86 Jack Oujo: From Umpire to Financial Independence Expert
Jack Oujo spent eight years chasing a Major League umpiring career before a release letter ended it at age 30, broke and with a baby on the way. He turned that setback into one of the most successful careers in wealth management, and in this episode he shares the exact strategies behind it. Jack...
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#85 Pivot or Perish: Mitch Carson on Media Evolution and AI-Driven Podcast Growth
How do you get an AI search engine to recommend your podcast? Mitch Carson, known as the instant celebrity maker, joins the show to answer that question and walk through 40-plus years of media experience, from radio and television to podcasting and AI search visibility. Mitch and Ben break down…
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#84 Scherrie L. Prince: Asset Protection Strategies Every Entrepreneur Needs
Growth without protection is a trap. Attorney and asset protection coach Scherrie L. Prince joins Ben to break down the asset protection strategies entrepreneurs skip until something goes wrong, from choosing the right entity structure to building an estate plan that actually matches your…
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#83 Kati Peterman: Fractional COO Systems to Scale Your Business
Kati Peterman, founder of Your FRX, has worked with over 1,200 businesses and helped them scale into multiple seven and eight figure revenue. In this episode she breaks down the SIPOC framework her team uses with every client, covering suppliers, input, process, output, and customer journey, and...
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#82 Drewbie Wilson: Sales Motivation and Execution: Call The Damn Leads
On this episode of Dissed Media: A Startup Story, Ben talks sales motivation and sales execution with Drewbie Wilson, founder of Call The Damn Leads and five-time author who has generated over $15 million in sales. They dig into why most business leaders don't have a lead problem, they have an...
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#81 Adam Torres: How to Monetize a Podcast and Build a Media Business
How do you monetize a podcast and turn it into a real business? In this episode of DissedMedia: A Startup Story, host Ben Olmos talks with Adam Torres, founder of Mission Matters and host of 15 shows with thousands of interviews behind him. Adam breaks down how to monetize a podcast from day one...
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#80 Ashley Smith: The Proof Gap: How Invisible Experts Get Found in AI Search
Some of the most knowledgeable professionals in their fields are nearly impossible to find online. In this episode of DissedMedia: A Startup Story, host Ben Olmos sits down with Ashley Smith, a former realtor of 18 years turned personal branding strategist who studies what she calls the proof…
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#79 Adam Spector: Back Office Outsourcing for Founders Who Want to Scale
Most founders lose their best hours to the back office. Chore founder and angel investor Adam Spector explains how back office outsourcing hands HR, finance, compliance, payroll, and bookkeeping to a fractional team that runs all of it for you, so you get your time back for product and customers....
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#78 Andrew Brummer: How to Reinvent Yourself After a Career Pivot
What does it actually take to reinvent yourself after your career pulls the rug out from under you? Andrew Brummer found out at 53 — no degree, no external network, and a company that was winding down after a decade of his best operational work. In this episode, he breaks down how he rebuilt from...
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#77 Dennis "DM" Meador: Authority Marketing Through Podcasting
What if your next client already trusted you before they ever called your office? That's the outcome Dennis "DM" Meador has been engineering for attorneys and professionals for the past two years, and it starts with a podcast. Dennis is the founder of The Legal Podcast Network and The Authority...
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#76 Mark Gordon: Go-To-Market Strategy and Product Market Fit for Founders
What separates a business that scales from one that stays stuck? In episode 76 of Dissed Media: A Startup Story, Ben Olmos sits down with Mark Gordon, founder of Integrated Go-To-Market Solutions, to break down the go-to-market strategy that turns struggling companies into growth machines. Mark...
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#75 Austin Bonderer: How to Patent an Idea and Protect Your Startup
Wondering how to patent an idea and protect your intellectual property before someone else profits from it? In this episode of DissedMedia: A Startup Story, host Ben Olmos talks with patent attorney Austin Bonderer, who brings 25 years of experience, more than 700 secured US patents, and an...
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#74 Ral West: How to Scale a Business That Runs Without You
What if you could step away from your business for a month and come back to find it ran perfectly without you? In this episode, Ben Olmos sits down with Ral West, an entrepreneur who spent 25 years building a Hawaii travel company into a charter airline flying 35,000 passengers a year between...
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#73 Randy Gage: Rewire Your Entrepreneurial Mindset and Build Wealth Without Apology
What if the biggest obstacle to your success isn't your strategy, your market, or your competition but the beliefs you inherited before you ever started a business? Randy Gage knows this firsthand. He went from a jail cell as a teenager to becoming a Speaker Hall of Famer, a multimillion-dollar...
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# 72 Charlie Sheppard Stop the Drama, Start Leading: What's Really Killing Your Team's Performance
What if the toxic work environment you keep trying to fix is actually a drama triangle problem? This week on DissedMedia: A Startup Story, Ben sits down with Charlie Sheppard, behavioral scientist, executive coach, and author of Save Your Drama for Your Mama (available on Amazon:...
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#71 Wes Towers: How AI Threatened His Business And How He Fought Back
What happens when a professional tells you your life's work is losing value because of AI? That's exactly what happened to Wes Towers, founder of Uplift 360, an Australian digital agency with over 20 years of experience helping trades, construction, and service-based businesses get found…
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#70 Aurora Winter: How 7 Words Generated $3 Million in One Week
What if the words you're using right now are costing you clients, income, and opportunities, and you don't even know it? In this episode, Ben Olmos sits down with Aurora Winter, former Hollywood television executive, award-winning screenwriter, bestselling author, and founder of Same Page...
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#69 Debbie Fay: Stop Killing Your Presentation — What Nobody Tells You About Public Speaking
Most people think they know what makes a great presentation. They are wrong. In Episode 69 of DissedMedia: A Startup Story, Ben Olmos sits down with Debbie Fay, founder of Bespeak Presentation Solutions and author of Nail It: Create and Deliver Presentations That Connect, Compel, and Convince....
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#68 Dr. Andy Neillie: Personal Development Lessons from Leadership Expert
If you're serious about personal development, this episode of DissedMedia: A Startup Story is exactly what you've been looking for. Dr. Andy Neillie, bestselling author, keynote speaker, and leadership consultant with over 20 years of experience, joins Ben for a deep dive into the leadership…
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#67 Anna Brambilla: Reclaim Your Time With a Virtual Assistant
Are you drowning in admin tasks and losing sight of why you started your business in the first place? In this episode of DissedMedia: A Startup Story, Ben sits down with Anna Brambilla, founder of Virtually Aligned, to talk about how hiring the right virtual assistant can help entrepreneurs…
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#66 Rich Ashton on Turning Great Workers Into Confident Managers
What makes someone a great leader? According to Rich Ashton, it is not something you get to decide for yourself. The people who follow you make that call. Rich Ashton is the founder of Growing Your Own Leadership, a program built specifically for small businesses that need to develop managers…
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About this show
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.
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DissedMedia
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