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.

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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

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

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

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

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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:

Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do:

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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:

Grab Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do: https://amzn.to/4uDUC7K

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 the door has already been closed on them. In this conversation he pulls back the curtain on how the guesting industry operates from the host's side of the microphone, why it is believed that north of 90% of podcasts never reach episode 20, and what separates the guest who books the show from the one who gets deleted unread.

Josh makes the case that guesting is a learned skill set, and that answering a question correctly and answering it well are two very different disciplines once business goals are attached to the appearance. He explains what he calls lottery mentality, where people pitch the top 100 shows before they have earned any track record at all, and he walks through how PodVerified works as a free credit score for podcast guests, giving you a score and telling you what caliber of show you should seemingly be aiming for right now.

The conversation also centers upon the assets that quietly signal whether a guest is serious, including a visible press kit, a LinkedIn profile written for producers rather than for converted customers, and a website where the person a listener just heard on the show is still easy to find instead of buried somewhere on an About Us page. However, the segment that may sting most is Josh's take on calls to action, since booking a call, joining a newsletter, and gated lead magnets all rank among the lowest performing asks a guest can make; he offers an alternative that centers upon getting listeners off the podcast and into your own environment with ungated short-form video, then earning enough minutes of attention that conversion takes care of itself. Ben takes that hit live on air, because his own closing call to action gets named.

Josh closes with the argument underneath all of it, which is that he has grown two seven-figure companies without ever spending a dime on advertising, and that generosity can outperform the lead generation tactics that most business owners already hate doing.

Josh Elledge

Get the first chapter of Ben's book, 10 Topics to Help Managers, Leaders & Entrepreneurs Get Better at What You Do: https://amzn.to/4uDUC7K

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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 work of Dr. Robert Cialdini, who personally trained and licensed him as one of a small number of practitioners worldwide.

Patrick centers upon a distinction that Nobel laureate Daniel Kahneman made famous, in which System 1 runs fast and unconsciously on shortcuts while System 2 works slowly, consciously, and only when red flags go up; roughly 90 to 95 percent of decisions get resolved by the first system, and yet the arguments most of us prepare are built for the second. The result may look like rejection, however it is often indecision, since an audience handed too much material for conscious processing tends to grow uncertain and back away from an offer that would genuinely have served them.

He is careful about the word ethical, because persuasion practiced honestly builds loyalty that survives long after you leave the room, while the manipulative version can produce short-term numbers and long-term damage once clients work out what happened. Along the way he covers why face-to-face still outperforms every other channel available to you, what a gated e-book actually does to reciprocity, the review score range that reads as credible rather than suspicious, why loss framing moves people roughly twice as far as gain framing, and what one truthful sentence added to a receptionist's script did to a London real estate office, where appointments rose 20 percent and signed contracts rose 15.5 percent.

Founders, sales leaders, marketers, and anyone who has to move other people through an idea will find something usable here, and it is worth saying that Patrick treats all of this as a learnable skill; the principles seemingly hold across languages and cultures, which may explain why work first published in 1984 keeps appearing on lists of timeless reads for entrepreneurs.

Chapters

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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.

Walt is the creator of Superfluidity and the founder of AI Gather, a project that began with a simple goal, building a working app for his ex-wife's gardening business without having to write the code himself; however, getting that app to scale turned into a two-year lesson in why most AI-generated software eventually collapses under its own patches. The breakthrough, when it finally arrived this past July, came down to one idea that unsettled several developers he shared it with, namely that the guardrails meant to keep AI safe were also part of what kept it from scaling, and that the fix required letting AI make the decisions software has always tried, and mostly failed, to hard-code in advance.

That same breakthrough eventually led to Superfluidity, a service Walt describes as something like an advisory tool for startup ideas, built to help entrepreneurs weigh viability and competition while accounting for the time it might take to reach profitability. Ben and Walt spend the rest of the conversation on the mechanics of running multiple AI models as a working team, along with the principles it took months of arguing with three different AIs to establish. They also get into why a startup building its code base from scratch sits in a much better position to take this approach than an established company, since it carries none of the old patches an existing system may already depend on.

If you're building anything with AI right now, this conversation may change how you think about the gap between a demo that works and a product that scales.

Learn more about Walt's work at super-fluidity.com and ai-gather.com, or reach him directly at [email protected].

Grab Ben's book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better At What You Do, at https://amzn.to/4uDUC7K.

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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 school textbooks, and how his holistic approach to pricing has helped companies scale from hundreds of millions to over a billion dollars in revenue by changing nothing but how they price and present their offer.

Per and Ben dig into real case studies, including a coffee chain that doubled sales volume with a smarter marketing message instead of a price cut, and a SaaS company that raised prices 400 percent while growing both revenue and customer satisfaction. They cover price anchoring using Apple's infamous $17,000 gold Apple Watch, the psychology behind why a $100 bottle of wine tastes better than a $6 bottle even when it is the exact same wine, and why dynamic and surveillance pricing are reshaping how companies price everything from airline seats to your grocery cart.

Learn more about Per Sjofors and his consultancy, Sjofors & Partners, at sjofors.com. Connect on LinkedIn at linkedin.com/in/persjofors or follow the company page at linkedin.com/company/sjofors, and catch more of his content on YouTube at youtube.com/@thepricewhisperer. His book, A Holistic Approach to Pricing Power, is available now: https://amzn.to/46ojTby

If you're building a business and want more ideas beyond pricing, check out my book, 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Do: https://amzn.to/4uDUC7K

We're on a mission to hit 100,000 subscribers by the end of 2026. Subscribe to DissedMedia on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1

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.