DissedMedia: A Startup Story

DissedMedia
  • 5.0 (3)
  • Entrepreneurship
  • Updated Daily

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.

  1. 4d ago

    #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 David Leibner, CEO of Stupid Good, whose career spans roughly a decade working bars and kitchens and about twenty years building software for the hospitality industry, including GiftLocal, the digital gift card program that now sits on the websites of thousands of restaurants. That combination of operator experience and product development is uncommon, and it may explain why David approaches the question of where to eat and drink with a practitioner's sense of what diners and owners will actually use. The conversation centers upon Stupid Good, a consumer discovery platform David describes as the Spotify of where to eat and drink, one that pairs curated local lists with an AI concierge that can learn a user's tastes and dietary needs over time. David walks through the history of the idea, which began as a decision-tree chatbot called Foodie Bot roughly seven years ago and was shelved several times before advances in AI, along with encouragement from a friend and advisor who had been deploying AI across his own company, made the concept seemingly viable. He also explains why published rankings and star ratings can fall out of date almost as soon as they are written, and why a system that reads reviews and social posts every day may be better suited to answering the question for a specific person on a specific night. Ben and David also dig into the business model, which relies upon a largely free experience intended to build community first, a paid concierge tier, a lifetime offer for founding members, and aggregated trend data that could be of value to operators and beverage brands; Ben, drawing on his own background in the wine industry, raises the long-standing gap in restaurant-level data that suppliers face, and David shares how a Negroni list in every city might sell more Campari than a traditional ad campaign ever could. The episode closes with David's plans for a nationwide birthday loyalty program that could give local restaurants a tool previously reserved for large chains, along with his firm position that no business can pay its way onto a Stupid Good list. Try Stupid Good: https://stupidgood.ai About DissedMedia: A Startup Story DissedMedia: A Startup Story takes listeners behind the scenes of building a business from the ground up, hosted by Dr. Ben Olmos. Now in season five, the show is joined by our new panel podcast, Better @ What You Do, where experts in a space take on the business problems coming up today. We are working toward 100,000 YouTube subscribers by the end of 2026, and if this episode delivered value, subscribing and sharing it with a friend can help us get there. Subscribe on YouTube: https://www.youtube.com/@DissedMedia   www.dissedmedia.com  www.rostr.studio  www.benolmos.com

    #102 David Leibner From Restaurateur to App Founder: The Spotify of Where to Eat and Drink

  2. Sep 25

    #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 a large one, and that posting constantly is not the lever most business owners think it is. He and Ben talk through the real distinction between being the most connected person on LinkedIn and being the best connected, plus how a genuine mutual connection turns into a warm introduction instead of a cold pitch. They also get into why a personal profile beats a company page for generating leads, and why paying for LinkedIn Premium before you've tested the limits of the free platform rarely pays off. Daniel is the author of Build a LinkedIn Profile for Business Success. Find his work and book a session with him at danielalfon.com, or connect with him on LinkedIn at www.linkedin.com/in/alfon and on X at @DanielAlfon. Get Daniel's book, Build a LinkedIn Profile for Business Success: https://amzn.to/4jmiRob  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

    #101 Daniel Alfon: Why Fewer LinkedIn Connections Mean More Referrals

  3. Sep 24

    BAWYD #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 settlement and YouTube's new monetization requirements, along with the steady decline in new podcast launches. The conversation opens with the settlement, which the panel compares in scale to the tobacco settlement; however, Adam Spector of Chore argues that it may be fighting the last battle, since the next wave of concern seemingly centers upon AI chatbots and the companies building them. Brett Schklar raises the contradiction of teenagers who reject anything that looks AI-generated while spending hours inside algorithm-driven feeds, and Rob Broadhead points to the age verification problem that has followed the internet since its earliest days. That thread leads into the heart of the episode, where Ben introduces the idea of a motivational quotient, or MQ, as the capability that may matter most once intelligence becomes available to anyone by the token, and Brett names it plainly as grit. Adam worries aloud that frictionless tools could leave all of us sitting in WALL-E chairs, while Rob offers a more hopeful reading in which AI clears away the grunt work so that people with real drive can aim higher than they could before. From there the panel turns to the YouTube Partner Program and its higher watch-hour threshold for monetization, and the reactions vary considerably; Jeremy Yang expects smaller creators to lean harder into sponsorships, Rob suggests the change may push creators toward owning their platforms and audiences directly, and Adam takes the view that AI-generated content will eventually reshape YouTube much as YouTube reshaped Hollywood, while Brett, speaking as a viewer who has grown tired of AI slop and faceless videos, welcomes the higher bar. Ben's observation that nobody dabbles in social media, and that consistency and relentless improvement tend to separate the channels that last from those that fade, prompts Adam to widen the point to any career, since obsession with getting better at the work seemingly pays off whether someone is building a YouTube channel or baking pies. The final segment centers upon podcasting itself, where celebrity shows and Netflix distribution sit alongside a decline in new launches, a pattern Brett attributes to the pandemic hangover finally wearing off. The group compares notes on podcast monetization and lead generation, with Rob, whose show has passed 1,000 episodes, describing podcasting as primarily a networking game, and they weigh whether being a guest on other shows can deliver more value than hosting one; Adam closes by framing the entire conversation around the ROI of your time, which may be the most useful lens any leader can bring to deciding where their grit is best spent. Panel: Adam Spector, four-time founder of Chore and host of Entrepreneurial Excellence https://hirechore.com Brett Schklar, enterprise futurist and author of AI Without the BS: The CEO's Playbook for Actually Getting AI Right https://brettschklar.com Rob Broadhead, founder of RB Consulting and host of Develpreneur https://rb-sns.com Jeremy Yang, founder of Digital Goliath and host of Marketing and Ops for SMEs https://digitalgoliath.com.au Better at What You Do is sponsored by Rostr Studio. Questions about topics or guests can be sent to podcast@dissedmedia.com. www.dissedmedia.com  www.rostr.studio  www.benolmos.com

    BAWYD #1 Grit in the Age of AI: What Leaders Can Learn from Meta's Settlement and YouTube Monetization

  4. Sep 22

    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 little over a year ago, seemingly changed how I understood podcasting and convinced me to put the show at the center of DissedMedia. From there, much of the conversation centers upon the practical side of building a podcast on a bootstrapped budget, including how the guest pipeline grew from cold pitches by bookers and PR firms into referrals through Ben Albert's Grow Getters Only network and PodMatch, how a growing backlog of recorded episodes and a modest $5,000 in seed money led me to build Rostr Studio, which brought in about $125 in its first week, and how each episode moves from a first edit in Descript through CapCut, vidIQ, Semrush, and Podbean before it reaches you. The episode closes with the announcement of Better @ What You Do, a new panel-format show drawn from my book, 10 Topics to Help Managers, Leaders & Entrepreneurs Get Better at What You Do, which gives several guests at once the room to carry a conversation further than a single interview may allow; the first episode, taped with Adam, Jeremy, Brett, and Rob, is in the edit now and will air on the DissedMedia feed before eventually moving to its own channel. If you have been listening along, thank you, and I hope you will stay with us on the way to episode 200. www.dissedmedia.com  www.rostr.studio  www.benolmos.com

    100 Episodes: From Cold Calls to Cash Flow

  5. Sep 20

    #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 financial services, reaching the top 200 producers in an industry of roughly a million people, before turning that experience into coaching and advisory work through Kinetic Spark Consulting. Jen explains why downloads may be the least useful figure a host can track, since half of all indexed podcasts seemingly peak near 27 downloads in their opening week, and she lays out the discernment process she applies before accepting or extending an invitation. The two of them get into what separates a prepared guest from a forgettable one, covering the story frameworks she teaches and the reason canned pitch emails get deleted unread. She also shares the story behind the title, including the childhood that shaped an overachiever's habit and the philanthropic work that led to two knighthoods and her standing as an elevated dame commander. However, the thread running through the hour comes down to treating every guest as a potential partner and designing a network on purpose. Connect with Lady Jen Du Plessis Website: https://www.jenduplessis.com Email: mentormeladyjen@gmail.com Mortgage Lending Mastery: https://ladyjenduplessis.com/mortgage-lending-mastery Success to Significance: https://ladyjenduplessis.com/success-to-significance Business on the Vine: https://ladyjenduplessis.com/business-on-the-vine Tell Me I Can't: https://amzn.to/3V0nYR6 Impact: Inspiring Motivational Powerful Acronyms for Cognitive Thinking, Volume Three: https://amzn.to/4rnTTqv Books: https://amzn.to/4rnTTqv | https://amzn.to/3V0nYR6 Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do: https://amzn.to/4uDUC7K Subscribe on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

  6. Sep 17

    #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 begins moving work faster than the organization was built to handle. In this episode of DissedMedia: A Startup Story, I sit down with Rob Broadhead, founder of RB Consulting and a fractional CIO with more than 30 years of experience across companies ranging from startups to the Fortune 50. Together they talk through the idea that AI behaves as an accelerant, amplifying whatever an organization already does, the strong parts and the weak parts alike. Rob centers upon a point many leaders may overlook in their rush toward a solution; business process improvement usually has to come first, because defining the real problem, including its exceptions and the places where employees quietly fix things by hand, can determine whether an AI implementation pays off or simply moves a company faster toward its true bottlenecks. Rob explains how he uses a string of repeated why questions to push past surface requests such as "we need a CRM." He also describes how he earns the trust of frontline employees who may be guarding process knowledge that the executive team has never seen, an approach that tends to soften even the blockers who seem most resistant at the outset. When a client wants results before the discovery work is finished, he looks for a smaller, painful problem that can produce a quick win, much the way an emergency room physician treats the most urgent wound before anything else. The conversation also moves into the shadow spreadsheets and shadow AI tools that can appear wherever an organization has not supported its people well. Rob makes the case for keeping company context portable so that a business can switch between AI models as they leapfrog one another. Rob discusses why some companies that cut roles in favor of automation are now rehiring, often into positions that look different from the ones they eliminated. Rob also walks through his Decision Bottleneck Scan, an interview process that seemingly works best when it helps an executive put words to problems they already sense. For founders weighing whether to bring in outside help, his advice starts with trusting your gut; the clearer signal, however, may be a lack of clarity, particularly when nobody can name who is waiting on a bottleneck or who has the authority to move it. Connect with Rob Broadhead Website: https://rb-sns.com Email: rob@rb-sns.com LinkedIn: Rob Broadhead and the RB Consulting company page, home of the weekly Inside the Process series and weekday five-minute AI tips Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do: https://amzn.to/4uDUC7K Subscribe on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1 More from Ben: dissedmedia.com | rostr.studio | benolmos.com

  7. Sep 14

    #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. Jaden Sterling spent the 1990s inside that world, first at Merrill Lynch and then at Citi Corp, and what he noticed there set the rest of his career in motion; clients came in holding a handful of individual stocks in companies like John Deere and IBM, management told him to sell those positions and move the money into packaged products, and over the years it became clear that the clients who had simply held their original shares would have done considerably better than the diversified portfolios they were moved into. In this episode of DissedMedia: A Startup Story, host Ben Olmos talks with Jaden about what he built after he walked away from that system. Sterling Stock Picker is now in its ninth year with close to 6,000 members, and it runs on a patent-pending ranking system called North Star that scores a stock on financial health, insider buying and selling, analyst sentiment, and the percentage of shares held short rather than owned long. The platform was built upon investing fundamentals long before AI was a going concern; the AI investment coach sitting on top of it now, however, serves as confirmation and education, which Jaden draws a hard line between and the idea of handing a bot the login to your trading account. Across the rest of the conversation, Ben and Jaden get into what separates investing from trading, why balance sheet strength may matter far more now that the 30-year Treasury sits near levels it has not seen in a very long time, how fractional shares let someone start small, and why Jaden believes it is never too late to begin. He tells the story of a subscriber who put insurance money into stock in a tool company her father had worked around her whole childhood, and what happened to that position afterward may be the cleanest argument for his core advice, which centers upon investing in industries you already understand. This episode covers investing education and general market discussion. It should not be treated as investment advice. Connect with Jaden Sterling: Sterling Stock Picker offers a 30-day free trial, and Jaden can be reached directly through the platform. https://sterlingstockpicker.com  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

  8. Sep 12

    #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 this episode he explains what happens when a dyslexic or neurodivergent founder tries to force themselves into someone else's framework. Willie has carried this message across more than five hundred stages and upward of one hundred sixty podcast episodes, by his own account, and much of that output traces back to one idea he keeps returning to: staying stuck in analysis costs more than most people realize, and getting unstuck starts with treating neurodivergence as a design constraint to build around, not something to hide or manage. Ben and Willie work through what generic productivity advice tends to get wrong for non-linear thinkers, what an alternative morning might actually look like in practice, and where the line sits between honoring how your brain operates and using that as an excuse to avoid something difficult. Willie also walks through the GPS Method, a free one-page framework he built for people who recognize themselves in this conversation but aren't ready to invest in coaching; it may be the most useful takeaway here for anyone trying to move from analysis into action this week. Connect with Willie Blake: Website: https://coachwillieblake.com LinkedIn: https://www.linkedin.com/in/willieblake-light/ YouTube (Dyslexic Achievers Hub): https://www.youtube.com/@DyslexicAchieversHub Facebook: https://www.facebook.com/WillieBlake.Light/ Instagram: https://www.instagram.com/willieblake_light/ Grab 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

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5
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About

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.

Information

  • Creator
    DissedMedia
  • Years Active
    2023 - 2026
  • Episodes
    103
  • Rating
    Clean
  • Copyright
    © DissedMedia Corporation
  • Show Website
    DissedMedia: A Startup Story