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

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

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 [email protected], 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

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:

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

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

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/.

How do you monetize a podcast and turn it into a real business? In this episode of DissedMedia: A Startup Story, host Ben Olmos talks with Adam Torres, founder of Mission Matters and host of 15 shows with thousands of interviews behind him. Adam breaks down how to monetize a podcast from day one through live events, book publishing, PR, and paid guest experiences instead of waiting on downloads and CPM. He shares his journey from a 14-year finance career to building a media company around storytelling, the dramatic sign that pushed him to go all in, and why the podcast business is still in its infancy with only four million shows worldwide. If you want to grow a podcast, make money podcasting, and stay in the game long enough to win, this conversation is full of practical, hard-won lessons.

Connect with Adam Torres:

Get 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 

Some of the most knowledgeable professionals in their fields are nearly impossible to find online. In this episode of DissedMedia: A Startup Story, host Ben Olmos sits down with Ashley Smith, a former realtor of 18 years turned personal branding strategist who studies what she calls the proof gap, the distance between what you know and what shows up when someone searches for you.

Ashley explains why AI search is rewriting how people discover professionals, why Google is overhauling search for the first real time in 25 years, and how she got her own expertise indexed on Google in just three days using podcasting and an RSS feed. She shares the concept of minimum viable proof, a practical 90 day sprint for building presence, and why being referenced by others may carry far more weight than posting on your own.

If you are a mid-career professional, an entrepreneur, or an emerging expert who wants to get discovered for what you actually know, this conversation gives you a clear place to start.

In this episode:

Connect with Ashley Smith:

About the show:

Most founders lose their best hours to the back office. Chore founder and angel investor Adam Spector explains how back office outsourcing hands HR, finance, compliance, payroll, and bookkeeping to a fractional team that runs all of it for you, so you get your time back for product and customers.

Adam has founded four companies and made more than 200 startup investments, and he built Chore to solve the problem that distracted him in every one of them. He breaks down how Chore differs from a PEO, the company stage where fractional support starts to pay off, why a single full-time generalist is often a liability, and how Chore's AI co-pilot Ollie turns your operational data into instant answers. If you want to spend more time in your zone of genius and less time chasing invoices and state registrations, this one is your playbook.

Connect with Adam and Chore:

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

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What does it actually take to reinvent yourself after your career pulls the rug out from under you? Andrew Brummer found out at 53 — no degree, no external network, and a company that was winding down after a decade of his best operational work. In this episode, he breaks down how he rebuilt from scratch, why he became a double author and co-founder of multiple companies, and what it means to make yourself operationally dispensable so the people around you can thrive without you.

Andrew and Ben get into the culture of trust that makes teams run without you in the room, the difference between listening to respond and listening to learn, how ageism is really just a failure to communicate across generations, and how AI can be your best thinking partner — or your worst echo chamber, depending on how you use it.

Andrew also shares the story behind My Story Told, his platform that uses AI to help people capture and publish their life stories — because everyone's earned the right to be remembered.

If you've ever hit a wall in your career and wondered what comes next, this one's for you.

Connect with Andrew Brummer:

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

What if your next client already trusted you before they ever called your office? That's the outcome Dennis "DM" Meador has been engineering for attorneys and professionals for the past two years, and it starts with a podcast.

Dennis is the founder of The Legal Podcast Network and The Authority Podcast Network. He has built a system that runs 250 shows and produces 350 episodes a month with a team of 75. His approach flips the traditional marketing model: instead of chasing reach and viral views, his clients publish niche, FAQ-driven content aimed at the exact people who need them most. The result is a pipeline of prospects who show up already sold.

In this episode, Dennis and Ben dig into:

— Why authority marketing through podcasting outperforms mass-audience content for high-value professionals

Dennis also shares two real-world examples of clients who had niche content already in place when major national news events broke in their specialty areas, and how that content turned them from local practitioners into nationally wait-listed authorities overnight.

Connect with Dennis "DM" Meador:

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

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