DissedMedia: A Startup Story

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Aug 2026

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About the 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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60 recent

August 22, 2026Episode 9151 min

#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 sellers before handing them directly to real estate agents, an approach he calls the "Un-Brokerage." In this episode, he breaks down how Intellitary's AI concierge, Chloe, converts website visitors into transaction-ready leads at conversion rates far above the industry average, why he engineered the business backwards starting from investor returns, and where he sees real estate technology heading over the next five to ten years. We also get into raising venture capital, finding strategic partners, and whether AI or human agents win the trust game in real estate. Learn more about Intellitary at intellitary.com. This episode is for you if you're interested in AI for real estate agents, real estate lead generation, proptech, real estate technology, or what it takes to disrupt a massive, entrenched industry.

August 18, 2026Episode 9053 min

#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 itself. Kenneth walks through his Small Business Flight Plan, a twelve-month framework built around leadership, marketing, sales, operations, product offering, and cash flow, and he explains why professionalizing the day-to-day of a business may be the single biggest competitive advantage available to a small business owner, however unglamorous that word sounds at first. The conversation covers what it actually takes to fix staff retention in a creative business, the difference between managing analytical teams and managing people who are driven by emotion and story, and the fixed mindset that seemingly holds so many owners back from the growth they say they want. Kenneth also shares how his own background, from professional soccer to ballroom dance to franchise ownership, shaped a coaching approach that focuses upon trust, communication, and process before it ever gets to the numbers. Learn more about Kenneth and grab his free resource library at https://kennethcoaches.com/free Pick up Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do: https://amzn.to/4uDUC7K Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

August 14, 2026Episode 8953 min

#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 that she started asking what she alone was qualified to build. That question turned into Two Mile High Marketing, the firm she runs today to help thought leaders land speaking engagements and podcast interviews while finally showing up on LinkedIn in a way that sounds like them. This conversation centers upon how to tell a legitimate marketing partner apart from the coaches and agencies that take five figures from ambitious executives and deliver nothing worth the price. Kelly explains the idea behind her book, Unlocking Your Authority X Factor, and how she found the specific expertise that made her different from every other consultant offering to build a personal brand. Getting booked is only half the equation, however; Kelly walks through why most speakers waste the stage moment without ever capturing an audience member's contact information. She and Ben also dig into what Kelly calls the messy middle of the founder journey, the stretch where the logo looks amateurish, the website barely functions, and it seemingly matters far less than most new founders believe it does. The two cover why building a paid speaking platform may take nine months or longer to produce a single booking, how to build a content strategy around core topics that keeps posting consistent instead of scattered, and what it takes to build a thought leadership platform people still remember months later. Learn more about Kelly's work and take her free thought leader scorecard at twomilehighmarketing.com. Her book, Unlocking Your Authority X Factor, is available on Amazon ( https://amzn.to/3Uy3z5m ) and at authorityxfactor.com. She also hosts two podcasts, Beyond the Bestseller and the Authority X Factor podcast . Grab Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do, here: https://amzn.to/4uDUC7K Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

August 11, 2026Episode 8856 min

#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 performance marketing programs that convert clicks into measurable revenue, and here he walks through the psychology separating an ad that earns trust from one that only earns a click, explaining why small businesses often rush into paid traffic before their website, offer, and social proof can actually hold it. The conversation then moves into the widening gap between B2B and B2C advertising, where a mindset built for e-commerce, chasing volume above all else, can quietly bury a B2B pipeline in leads that never close; Slaymaker ranks Google, Meta, TikTok, LinkedIn, Reddit, and the rising ad network AppLovin by where his agency has actually seen results, and shares what it is believed drives so many businesses toward AI-powered lead generation tools that promise everything and deliver very little. However, the sharpest turn in the conversation comes when Slaymaker breaks down the AI generated ads backlash following campaigns like Coca-Cola's AI-built Christmas commercial, citing his own polling showing that roughly seventy percent of people say AI in advertising damages how they see a brand, a number that seemingly should give every marketer pause before handing creative control to a machine. Connect with Matthew Slaymaker and Slaymaker Marketing at https://www.slaymakermarketing.com , or find him on LinkedIn. Grab the first free chapter of Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do, at https://amzn.to/4uDUC7K . Subscribe to DissedMedia on YouTube as we work toward 100,000 subscribers by the end of 2026: https://www.youtube.com/@DissedMedia?sub_confirmation=1

August 7, 2026Episode 8754 min

#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 currently serves as chief marketing officer of Easy Home Search, and across a career that includes an $880 million IPO, dozens of acquisitions on both sides of the table, and behind the scenes advisory calls to the White House, he has arrived at a fairly blunt conclusion, which is that more dashboards rarely lead to better decisions and more tools rarely lead to better growth. The conversation works through why tracking the wrong things can quietly train a team to chase clicks and impressions instead of revenue, how a systems mindset built from years as a software architect shapes the way Uhlir now approaches both marketing and AI in marketing, and what it takes to lead a team toward bold or unpopular decisions without those decisions landing as a shock later. However, the most surprising thread may be how little marketing psychology actually changes from country to country once a team understands who its customers really are, translation and slang aside. Uhlir also walks through the call that pulled him into advising the Trump administration on the Made in USA country of origin label, a role that started with a single phone call he almost mistook for a prank from old college friends. Timestamps 00:00 Introducing Kurt Uhlir and what brought him to Easy Home Search 04:20 Why Kurt does not trust dashboards 06:54 Staying grounded in outcomes instead of activity 09:16 Task based leadership versus outcomes based servant leadership 12:09 Why most people with marketer in their title are not marketers 14:27 Systems mindset, psychology, and statistics in marketing 17:41 What changes, and does not change, across countries 21:22 The purpose behind setting goals inside servant leadership 26:06 Getting a team and a board on board with unpopular decisions 30:38 Bringing leadership into the reality of AI in marketing 39:40 Advising the White House on the Made in USA label 51:39 Where to find Kurt Uhlir and Easy Home Search Connect with Kurt Uhlir Website: https://kurtuhlir.com Easy Home Search: https://ezhomesearch.com Dissed Media is on a mission to hit 100,000 YouTube subscribers by the end of 2026. Subscribe here: https://www.youtube.com/@DissedMedia?sub_confirmation=1 Grab the first chapter of Ben Olmos's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do, free at his website, or pick up the full book on Amazon: https://amzn.to/4uDUC7K

August 4, 2026Episode 8657 min

#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 breaks down why income taxes, not your mortgage, are most people's biggest expense, and how maxing out a pre-tax retirement plan solves two problems at once. He walks through the worst case scenario planning that came straight from his umpiring days, why paying off your mortgage before retirement protects your downside, and the early hiring mistakes that taught him to pay for quality over cost. He also gets into what he's taught his own kids about choosing a marketable career and building financial independence instead of chasing hype. If you're working through a tax planning strategy, thinking about wealth management for the years ahead, or just want a clear path to financial independence, this conversation is packed with the kind of practical, math based thinking that built Jack's firm. Connect with Jack Oujo Book, Too Smart to Be an Umpire: https://amzn.to/4xaM7lx Oujo Wealth Strategies: https://www.oujowealthstrategies.com Ben's book, 10 Topics to Help Managers, Leaders, and Entrepreneurs Get Better at What You Do: https://amzn.to/4uDUC7K Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

July 21, 2026Episode 8553 min

#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 the podcast workflow that keeps a show running consistently, why most podcasters quit within the first eight episodes, and how tools like Claude, Semrush, and Substack are reshaping podcast SEO and content strategy in 2026. Topics include the collapse of barriers to entry in media, building an automated production pipeline from recording to distribution, Substack versus Spotify for podcast growth, using Claude's MCP connectors to manage a website and podcast bookings, and why ranking inside AI search results (not just Google) is becoming the new authority game for creators and entrepreneurs. Connect with Mitch Carson at www.MitchCarson.com or MitchCarson@RocketMail.com , and check out his podcast, The Amazing Authorities Podcast. Connect with Ben Olmos at benolmos.com, and check out his book, 10 Topics to Help Managers, Leaders & Entrepreneurs Get Better at What You Do, available on Amazon and Barnes & Noble. If you enjoyed this episode, please leave a review. It helps more listeners find the show. Timestamps 00:00:00 Introducing Mitch Carson 00:02:01 40 years of media evolution 00:06:24 Pivot or perish in a changing media landscape 00:10:06 The barrier to entry has collapsed 00:13:22 Why most podcasters quit after eight episodes 00:18:22 Ben's production and distribution workflow 00:20:14 Substack versus Spotify for podcast growth 00:24:25 Claude, MCP connectors, and AI-powered workflows 00:26:32 Mitch's offer of a follow-up interview and PR package 00:39:35 The origin of "the instant celebrity maker" 00:41:14 Semrush, Claude, and keyword research in practice 00:47:54 Where to find Mitch Carson

July 16, 2026Episode 8443 min

#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 business. Scherrie explains her four-part framework for structuring a business from day one, why a 50/50 partnership on a handshake is a lawsuit waiting to happen, and how mixing personal and business finances can pierce the corporate veil and expose your personal assets. She and Ben also dig into a real-world estate planning failure, the Gene Hackman will dispute, and what it teaches about keeping legal documents current. Scherrie is the author of Build The Moat First: A Practical Guide for Entrepreneurs Who Want to Grow Without Building a Fragile Business, and host of the Play Big Faster podcast. Connect with Scherrie: LinkedIn: @SherriSpeaks Play Big Faster podcast: available wherever you get your podcasts Pick up Ben's book: 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do — https://amzn.to/4uDUC7K Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

July 14, 2026Episode 8356 min

#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 explains why response time is the single biggest revenue leak she sees across industries. Kati and Ben talk through how to get buy-in from a team that resists new structure, why staying in your lane protects both culture and cash flow, and two real client turnarounds where her team cut outstanding collections from four million dollars down to 1.2 million and from eight hundred thousand down to two hundred ten thousand. They also dig into how fractional executive support differs from traditional consulting and what it actually takes to build a company that runs on systems instead of guesswork. Connect with Kati Peterman and learn more about Your FRX at https://yourfrx.com . She's also active on LinkedIn if you'd like to reach out directly. Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do, is available now: https://amzn.to/4uDUC7K Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

July 9, 2026Episode 8248 min

#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 execution problem, and how self discipline outside of work builds sales confidence inside of it. Drewbie shares his path from a 1.6 GPA and failed English classes to building a national sales training brand, how he lost 100 pounds and rebuilt his confidence through personal development, and the systems he uses to turn sales execution into a repeatable habit instead of a one-time push. If you want practical sales motivation and a clear look at what daily discipline actually looks like, this episode has it. Find Drewbie and his books at https://callthedamnleads.com/ , and follow him @callthedamnleads on social. Grab Ben's book, first chapter free, at https://benolmos.com/ .