DissedMedia: A Startup Story

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 client story of a personal trainer who went from $1,200 to over $100,000 a month, to how Nicky screens who he'll actually work with.
Listeners will come away understanding why Nicky thinks "narrowing your focus" only works when it's tied to a real emotional connection, not just a bigger paycheck, how he structures his mastermind dinners to stay value-driven instead of turning into pitch-fests, and why he believes most business owners dramatically underrate how much a 10-out-of-10 commitment to selling would change their results.
In this episode:Nicky's family fleeing Iran after a Molotov cocktail landed in their living room, and how his father's habit of giving away loans shaped Nicky's view of entrepreneurshipThe story of "Danny," a personal trainer who went from $1,200/month to signing 400 clients in six weeks after narrowing his focus to people with missing limbsHow Nicky screens potential clients through an application form, looking for at least three years of business experience and genuine intent to actThe structure of his mastermind dinners: six to eight people per "pod," a no-pitching rule in the group chat, and sponsors getting a short pitch slotHis "steep effort to benefit ratio" theory, that dropping below a 9 or 10 out of 10 in sales skill costs you the vast majority of potential clientsThe story of coaching a Texas RV park investor from giving away coaching for free to charging $10,000 for an eight-week programSpotting "charlatan marketers" who are good at "selling the sizzle" but don't deliver, including a personal story about a no-show meeting that turned into a patternNicky's view that a coach who only makes a client "like them" without pushing for results has failed them
About Nicky Billou, Founder / Co-Founder, ECircleWebsite: https://www.ecircleacademy.comFacebook: https://facebook.com/thethoughtleaderrevolutionX: https://x.com/NickyBillouInstagram: https://instagram.com/nickybillouLinkedIn: https://www.linkedin.com/in/nickybillou/

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 company built on a mouthy rescue Rottweiler, and, most strikingly, turning the loss of his lower leg into a consulting income stream within months. This is a conversation about reframing circumstance as opportunity, not a conventional business playbook.
Listeners will come away with a concrete way of thinking about side income: that applied, current knowledge from years on a job is worth as much as a degree, that AI is a tool for solopreneurs to close the "knowledge gap" rather than a threat, and that building multiple income streams is really about financial security rather than chasing billionaire status. The episode closes with Merrell's own version of the Acres of Diamonds parable, built around his father's pig farm, as a way of asking listeners where their own overlooked asset might be.
In this episode:How a disqualifying eye surgery derailed Merrell's planned FBI career and redirected him into bungee tower contracting in JapanStarting a DJ business at 15 by renting the community center himself because no one would hire a teenage DJReframing a prosthetist appointment as a job interview and turning it into a paid retainer helping other amputees six months after surgeryBuilding a six-figure first year in dog training after a rescued Rottweiler named Rex kept getting him on the phone with a trainer friendTurning down free funding for a Japanese curry restaurant because he didn't want the level of hands-on work it requiredWriting and releasing AI-assisted music under two alter egos, Mason Kane and Dana Call, as a low-earning but enjoyable side projectThe origin of "Monetize Your Mindset" from watching a rehab center Toastmasters session and a sister's Facebook post about living on lessWhy a cancer scare with his wife in the early 2000s pushed him to build multiple income streams before the amputation happened
About Bart Merrell, Founder, The Side Hustle SamuraiWebsite: https://thesidehustlesamurai.com/https://thesidehustlesamurai.com/shophttps://youridealsidehustle.comLinkedIn: https://www.linkedin.com/in/bart-merrell-2440148/Facebook: https://www.facebook.com/bart.merrellYouTube: https://www.youtube.com/@BartMerrell-SideHustleSamuraiTikTok: https://www.tiktok.com/@bart.merrellInstagram: https://www.instagram.com/bartmerrell/
Chapters:0:01 Introduction and premise of the show3:01 FBI dreams, disqualifying eye surgery, and landing in Japan8:44 Reframing the leg amputation as something to monetize11:04 AI, authenticity, and why side hustles make sense now18:21 Building a six-figure dog training business from a rescued Rottweiler23:19 Turning down the Japanese curry restaurant opportunity33:51 DJing heavy metal and country in small-town New Mexico40:37 Creating AI music under two alter egos48:31 Writing "Monetize Your Mindset" after a Toastmasters session at a rehab center1:04:47 A cancer scare and the push to build multiple income streams1:15:13 Closing story: Acres of Diamonds and acres of pig poop
More from DissedMedia: www.dissedmedia.com

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 the first thing pushed aside when the calendar fills up. In this episode of DissedMedia: A Startup Story, Ben Olmos sits down with Debora Prossomariti, founder of Personal Branding Atelier and a Fractional Chief Brand Officer to CEOs, who began building her own visibility on LinkedIn during a job search, went on to advise businesses on paid social at Meta and Pinterest, and launched her consultancy as a side hustle that, by her account, allowed her to leave her full-time role within about four months.
The conversation centers upon the practical side of building CEO authority online, beginning with the mismatch she often sees between the message a leader sends and the result that leader expects, and moving into the cultural differences that can shape how a message lands, a subject she approaches as someone who speaks five languages and has lived in ten countries. Debora and Ben discuss how a leader's ego and the urge to sound polished and corporate may get in the way of content that connects, particularly now that so much AI-written content reads the same, along with the reputational risk of posting without judgment; however, she makes the case that being intentional and strategic can coexist with showing up as yourself. They also work through the fear that tends to sit underneath "I don't have time," the balance between quality connections and enough volume on LinkedIn, how she views promoted posts relative to organic reach, and how often an executive may need to post, with her suggestion being that somewhere between one and four times a week can be enough for thought leadership.
Toward the close, Debora explains why it may be wiser to build credibility well before you need it, since an ask made from an empty profile tends to land very differently from one backed by a visible record of your thinking, and she previews CEO Brand Architecture, a new resource she is developing to help leaders assess where they stand and identify the gaps in their authority and reputation.
Connect with Debora Prossomariti:LinkedIn: https://www.linkedin.com/in/debora-prossomariti 
Get Ben's book, 10 Topics to Help Managers, Leaders & Entrepreneurs Get Better at What You Do: https://amzn.to/4uDUC7K 
Subscribe on YouTube: https://www.youtube.com/@DissedMedia 
Check out Rostr Studio: https://rostr.studio 

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:Newsletter: https://www.joshgriffin.co.uk/newsletter Website: https://www.joshgriffin.co.uk Intrinzi: https://www.intrinzi.com LinkedIn: https://www.linkedin.com/in/joshualloydmd/ Instagram, TikTok, and YouTube: @joshuagriffinseo 
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 Hustlehttps://doctorchristiane.com Take the Superpower Scorecard Quiz: https://quiz.tryinteract.com/#/680acbb35fb6f0001547ba20 https://linkedin.com/in/christianeschroeter 
Jack D. Oujo, founder of Oujo Wealth Strategies and author of Too Smart to Be an Umpirehttps://toosmarttobeanumpire.com Get the book: https://amzn.to/4xaM7lx Speaking engagements: https://bookjack.org 
Josh Rosenberg, founder of Forward Thinkershttps://www.forwardthinkers.io 
Ben's book: 10 Topics To Help Managers, Leaders, and Entrepreneurs Get Better @ What You Dohttps://amzn.to/4uDUC7K 
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 podcast@dissedmedia.com.
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 WolfGuideWise: https://guidewise.ai The Intelligent Business Equation: https://amzn.to/47vpoG3 LinkedIn: https://www.linkedin.com/in/tedwolftwo/ 
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 Benhttps://dissedmedia.com