DissedMedia: A Startup Story

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 collapse that sent him to the doctor.

In this episode of DissedMedia: A Startup Story, Ben Olmos sits down with Joshua, co-founder of the UK marketing agency Intrinzi, to talk through what it seemingly takes to rebuild after business failure, from a debt management plan and a winter spent sleeping in layers because the heating bill was out of reach, to a second venture that turned a profit within its first six months. Joshua explains why he chose to document the debt and burnout publicly as it was happening, how he pushed himself from five sales calls a day to one hundred despite hating outreach, and why he believes honesty with clients and audiences can matter more as AI fills every feed with the same polished advice.

The conversation also centers upon how Joshua found the right co-founder in a former colleague, and why he believes most founders should expect somewhere around three to five years before a business turns profitable, a timeline Ben recognizes from nearly four years of building DissedMedia in the red.

Connect with Joshua Griffin:

Get 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 

www.dissedmedia.com | www.rostr.studio | www.dailypitch.news | www.benolmos.com 

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 former guests of DissedMedia: A Startup Story to work through that question from noticeably different seats. The conversation opens with Disney president Dana Walden's remarks at a Bloomberg conference, where she called the company's latest round of cuts extremely painful while signaling that restructuring will continue each year. Jack Oujo, who spent eight years as a professional baseball umpire before founding Oujo Wealth Strategies, draws on clients between 50 and 65 who have lived under the threat of a layoff for years, and his advice centers upon knowing your numbers well enough to weigh a consulting role or an equity stake when the call finally comes. Josh Rosenberg, who was asked to relocate six times in six years to keep his job at a global beverage company, pushes back on the public reaction to Walden, arguing that society has grown cruel toward leaders who speak candidly and that accountability between employer and employee may be closer to 50/50 than most people care to admit. However, Ben holds that a leader ought to open with the people affected before offering the business rationale, and Dr. Christiane Schroeter adds that no job stays safe for the rest of anyone's life, so the work of building skills and relationships has to begin well before any announcement arrives.

From there the panel turns to hiring, where research out of Stanford suggests that applicants screened by the same vendor can carry one result from employer to employer, and where the discussion keeps returning to the people a job seeker already knows. Jack notes that all five people his firm hired in the past year came through personal connections, while Josh describes how a referral can pull a screened-out candidate back to the top of the pile. Christiane, who teaches innovation and entrepreneurship at Cal Poly, explains why people tend to be hired for character and trained for skill, and she introduces the failure resume, an exercise that turns setbacks into some of the strongest material a candidate can bring into an interview. Ben's own interview advice centers upon asking what success looks like in the role before answering anything else and closing every answer with a quantifiable result, and the group questions whether sending 200 applications without following up on any of them can really be called a job search.

The final stretch centers upon paid mastermind groups, some of which charge $20,000 to $40,000 for a seat, and Ben admits openly that he struggles to see the value proposition. Jack suggests that a struggling owner may learn more by sitting down with customers and employees before paying anyone, and Josh shares that he has been let go from three coaching engagements in the past year because clients did not like what their own people told him. Christiane offers a behavioral economist's reading of the price tag, in which spending an uncomfortable amount of money may be the very thing that finally makes some people accountable enough to change.

Connect with the panel

Dr. Christiane Schroeter, leadership strategist, Professor of Innovation and Entrepreneurship at Cal Poly, and host of Happy Healthy Hustle

Jack D. Oujo, founder of Oujo Wealth Strategies and author of Too Smart to Be an Umpire

Josh Rosenberg, founder of Forward Thinkers

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

Subscribe on YouTube: https://www.youtube.com/@DissedMedia?sub_confirmation=1 

Better @ What You Do is sponsored by Rostr Studio. Questions about topics or guests can be sent to [email protected].

www.dissedmedia.com  www.rostr.studio  www.dailypitch.news  www.benolmos.com

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 business to work. In this episode of DissedMedia: A Startup Story, Ben Olmos sits down with Ted Wolf, co-founder of GuideWise and author of The Intelligent Business Equation, to talk through how AI can raise business valuation for owners who are preparing for an exit.

Ted and his brother left IBM with $1,000 between them and knocked on ten banks for a $10,000 line of credit, getting turned down by nine; the tenth, seemingly the most conservative of the group, approved it on the spot and remained their primary bank for the life of the company. That technical consulting and IT staffing firm grew to roughly 650 billable professionals before it was acquired by a publicly traded company, and the lessons from that journey, along with years of executive coaching on how organizations adopt change, led him to co-found GuideWise with his son.

Ted focuses upon what is often called the silver tsunami, the wave of owners in their 50s and 60s whose net worth is locked inside their companies, and he estimates that as many as 10 million mid-sized businesses may need to change hands over the next seven years while buyer demand holds roughly steady. In that environment, he believes a business exit strategy without a credible AI plan can leave owners facing something close to a 30% chance of a successful sale, and he explains why lenders, including SBA lenders, are increasingly asking what a company intends to do with AI before extending credit.

Ben and Ted also work through the five closes from Ted's book, which move from knowing your numbers and building systems to implementing AI, orchestrating shared context across the business, and developing leaders who can process conflict, and Ted explains why he treats those closes as multipliers, where any one falling to zero can cancel out the rest. Along the way, the conversation touches on the leapfrog moment Ted expects as companies begin reporting bottom-line results from AI, his idea of the benevolent predator, lessons from the dot-com era, and why critical thinking and emotional intelligence may grow more valuable as AI spreads through the workplace.

Connect with Ted Wolf

Get 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 

Connect with Ben

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 details, the conversation carried some genuine risk for both of them. Ric and his wife Liz have spent roughly 25 years building companies together, starting with a dial-up internet service provider in the early 2000s, where a recurring run of failed servers and identical customer complaints that seemed to line up with Mercury retrograde gradually moved Ric from dismissal toward curiosity. That curiosity carried through 13 years of running Healthy, Wealthy and Wise, an online personal development magazine, where they watched bestselling authors quietly time their book launches to astrological calendars.

Temporal Intelligence brings seven symbolic systems, developed by different cultures across thousands of years, into a single written report called a Structural Architecture, and it treats the places where several of those systems agree as signal worth paying attention to. Ric is candid that he cannot explain why it works; his position is that observation is the first step in any science, and that the pattern either fits the person or it does not.

Over the course of the reading, the report seemingly lands on Ben’s comfort speaking plainly to rooms of any size, his career of reinventions, his habit of taking on more than he can finish, and the tendency of his reactions to reach speech before his judgment does. The two also talk through how managers might use a tool like this responsibly, how it compares to Myers-Briggs and DiSC, and a few client stories that may change how you think about where you fit. However you feel about astrology going in, this episode can serve as a useful prompt for any leader or founder thinking about how they are built and where that wiring may be helping or getting in the way.

Connect with Ric Thompson:

Hosted by Ben Olmos | www.dissedmedia.com 

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 with enterprise futurist Brett Schklar.

Brett founded the B2B marketing agency Market Creation Group in 2005, scaled it, and sold it to a private equity firm in 2019; after a period of reflection he started Grow Powered, a fractional CMO business, and following his own ChatGPT moment chose to run that company largely on AI and agentic models, keeping headcount and overhead well below what a traditional agency would carry. The interest that experiment drew from other executives led him to spend roughly half his time talking with more than 1,800 CEOs and business leaders, and what he has heard in those conversations may surprise anyone who assumes the largest companies are furthest ahead, since he finds many enterprise teams still reluctant to admit they use AI at all.

At the core of Brett's AI adoption framework is what he calls the power of the 1%, a habit in which each person identifies one easy task each week that AI can make less painful, an effort he suggests can compound into a team roughly 68% more effective over the course of a year. That weekly discipline can then scale toward larger monthly improvements and, eventually, toward the one problem each quarter that a team had long written off as impossible.

Ben and Brett also explore how AI may expose weak leadership as readily as it elevates strong leadership, and how AI seemingly reshapes tasks far more often than it eliminates jobs. Brett makes the case that AI strategy belongs to a cross-functional steering committee or center of excellence, with IT seated at that table as one voice among several, and he encourages leaders to push their software vendors and professional service providers to pass AI efficiencies along so the business is spared from building everything on its own. For business leaders working through AI change management inside their own organizations, the episode offers a measured and practical path that may lower the fear keeping many teams on the sidelines.

Connect with Brett Schklar:

Get 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 

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 inviting local business leaders onto a podcast that did not yet exist, which filled his calendar within days and seemingly turned each interview into a string of new introductions.

In this conversation, Ben Albert, owner of Balbert Marketing and host of Real Business Connections, shares the networking tips behind his CAN approach, where creating content alongside other people becomes the reason to connect. He walks through the LinkedIn outreach message that earned a yes from roughly three out of four of the people who connected with him, along with the "nominations" request that once produced 17 introductions from a single guest. He also explains the follow-up habits that may help an introvert become difficult to forget after an event, and why he would rather be different than better.

The discussion also centers upon the harder side of community building; Ben speaks candidly about closing the larger Grow Getters Only community that same week, and about narrowing his attention to the work that is already paying the bills.

Connect with Ben Albert:

Get Ben Olmos'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

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 conversation opens with a recent Omni Calculator survey in which 40% of employees said managers who use AI come across as less competent and 36% said they trust those managers' judgment less, with Gen Z offering the harshest read of all. Stephanie Sylvestre separates what she calls lazy AI from the kind that gets real work done, while Rich Ashton argues that communication may be the most powerful tool a leader has, and that handing it to a machine can give some of that leadership away. Joshua Griffin adds the view from a growing agency, where a phone call between two people outperformed every automated outreach campaign his team had tried.

From there the panel turns to social media, where LinkedIn feeds have begun to read like the same post written fifteen times and where YouTube's changes to how a view gets counted may leave creators with bigger numbers that say less. Views and subscriber counts can look impressive on a channel page; however, the panel keeps returning to whether any of it leads to a sale, a relationship, or a conversation worth having. The final stretch centers upon what draws listeners to a podcast, the host or the guest, before taking an unplanned and candid turn into women in leadership and the idea that hiring decisions should rest on the knowledge, skills, and abilities a person brings to the job.

Connect with the guests

Stephanie Sylvestre, CEO of Avatar Buddy: https://avatarbuddy.ai | https://www.linkedin.com/in/stephanie-a-sylvestre

Rich Ashton, Owner of Growing Your Own and author of Growing Your Own: https://growingyourown.net

Joshua Griffin, Co-Founder of Intrinzi: https://www.intrinzi.com | https://www.joshgriffin.co.uk

About the host

Ben Olmos is the founder of DissedMedia and the host of Better at What You Do and DissedMedia: A Startup Story. Find more episodes and everything else DissedMedia is working on at https://dissedmedia.com, with guest booking powered by https://rostr.studio and more from Ben at https://benolmos.com.

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 nine states. In this episode of DissedMedia: A Startup Story, Ben Olmos and Matt talk through how to start a distillery when doing so means leaving a steady paycheck for one of the most heavily regulated consumer product categories in the country, beginning with the week Matt spent at Moonshine University in Louisville learning production and compliance before he ever opened his doors.

The conversation centers upon the parts of the craft spirits business that founders tend to discover late. Matt explains how a 2020 cease and desist forced a rebrand from Tower 56 to 477 Distilling, a name drawn from the 477-vote margin that legalized alcohol in Greeley in 1969. He also describes how the three-tier system shapes alcohol distribution for a small producer, since self-distribution in Colorado gave way to distributor partnerships that worked well in Wisconsin; however, a faster push into additional states led to relationships he later had to end. The episode closes with the seven ventures he has launched, including an axe throwing venue that closed within six months, and the year in which the strain of running the business led him to professional counseling, which he writes about in his book, I Know the Owner.

Find Matt Estrin: www.477distilling.com and www.mattestrin.net 

Buy Matt's Book: https://amzn.to/4zohfiJ 

More From Ben & DissedMedia

www.dissedmedia.com 

www.rostr.studio

www.benolmos.com 

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 sales leadership, before joining a 129-person vending and refreshment operator in Texas and growing it to nearly 700 employees across 12 states under private equity ownership.

Ben and Josh, who worked together during those corporate years, trade leadership lessons that carried over from a large system into a founder-led company, including the "street to suite" clarity that may allow a strategy to survive contact with the front line. Josh explains his people, process, technology formula, the business acquisition model that worked when founders shared the company's values, and the late deals in which the analytics overruled his instincts and the culture absorbed the cost.

The conversation closes with his current advisory work, where a perceived sales problem often proves to be an organizational alignment problem, and where AI adoption begins with governance over who is using it and who retains the IP.

Connect with Josh Rosenberg

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

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

Subscribe on YouTube: https://www.youtube.com/@DissedMedia  

www.dissedmedia.com