• $110 Billion Hollywood Takeover Explained: Who Overpaid, Who Got Paid, and the AI Cash Burn
    Oct 7 2026

    This week three buyers wrote checks most of us will never see, and every one of them ran the same playbook you use on a $3 million deal. Charles and I take apart Paramount closing its $110 billion takeover of Warner Bros. Discovery, Schneider Electric agreeing to pay a 42 percent premium for industrial software company PTC, and Clayton, Dubilier and Rice teaming up with McKesson to take Option Care Health private in a 51 to 49 split. Then we get into OpenAI's projected cash burn through 2030, the industry call to slow down frontier AI, and what both mean for operators who buy real businesses.In this episode I cover:Why closing is the starting gun, not the finish lineHow a regulatory settlement works like a covenant package and an earnout in reverseWhy a premium is pre-paid synergy, and how sellers find the buyer who will pay itWhy SBA financed buyers usually cannot match a strategic buyer's premiumHow staged ownership works and the clauses a minority partner should demand before closingWhat it means when projected spending is bigger than projected revenueA holdco reality check on paying yourself versus reinvesting everythingThe deal on the front page and the deal on your desk are the same deal. Just move the decimal.Deal figures are as reported in public filings and news coverage at the time of recording. Schneider and PTC and the Option Care transaction are announced, not closed. OpenAI figures are company forecasts reported by the Financial Times, not results. Nothing in this episode is investment, legal, or tax advice.LINKSTry Deal Flow OS free - https://dealflow-os.comSubscribe to my newsletter - https://buybuildexitwithroyredd.subst...Follow me on Instagram - @buybuildexitFree Class - https://www.skool.com/buy-build-exit-...

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    58 mins
  • Anthropic IPO: The $518 Billion Bill Behind the $2 Trillion Valuation
    Oct 2 2026

    Anthropic wants to go public at a reported valuation above $2 trillion. According to its IPO prospectus as reviewed by Reuters, it lost about $42 billion last year, and roughly $34 billion of that was a non-cash accounting charge. The number I care about is different. Reuters reports at least $518 billion in cloud, compute, and infrastructure commitments, and about 80 percent of it is owed whether the compute gets used or not. That is not spending. That is a lease.Charles Oglesby and I underwrite the whole front page this week like it is a deal on our desk. Oura postponed its IPO the day it was expected to price, despite strong demand, and most of the shares on offer were insiders selling. AMD agreed to buy Fei-Fei Li's World Labs for about $8.2 billion in stock, not cash, and we break down why paying in stock turns a seller into a partner. A BlackRock-backed group is in exclusive talks for up to $25 billion of Asia-Pacific data centers after the seller asked for more than $30 billion. And Paramount's deal for Warner Bros. Discovery comes with roughly $79 billion of net debt and a ticking fee that starts October 1.Every one of these deals has a Main Street version. Customer concentration, key-person risk, rollover equity, lease terms, and lenders who underwrite trailing cash flow instead of synergies. Same mechanics, different zeros. If you are buying a business in the $1 million to $5 million range, this is how you read your own deal.Drop the deal you are looking at in the comments and Charles and I may underwrite it on air.Nothing in this episode is investment advice. Disclosure: I used Claude, an Anthropic product, to help produce this episode.0:00 Five deals, one question: who is paying?2:30 Anthropic IPO: the $42B loss vs the $518B bill14:00 Oura walks away from its own IPO21:00 AMD buys World Labs for $8.2B in stock30:00 BlackRock and the $25B data center talks38:00 Paramount, Warner Bros., and $79B of net debt51:00 Rapid fire56:00 Headlines report the price, operators read the capital stackLINKSTry Deal Flow OS free - https://dealflow-os.comSubscribe to my newsletter - https://buybuildexitwithroyredd.subst...Follow me on Instagram - @buybuildexitFree Class - https://www.skool.com/buy-build-exit-...

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    41 mins
  • The Warner Bros Deal: The $7 Million a Day CLock That Forced a Settlement
    Sep 24 2026

    The Paramount Warner Bros deal just cleared its biggest obstacle nine days before a $7 million a day ticking fee was set to start. Charles Oglesby and I break down why that timing matters and what it teaches you about buying a business at any size.Paramount beat Netflix for Warner Bros Discovery with $31 a share in cash, a $7 billion regulatory termination fee, and a promise to cover the Netflix breakup fee. Sellers price certainty, not just the headline number. Then 12 state attorneys general sued, and Paramount settled with commitments on film output, worker funds, and a news editorial independence board. The deal is settled, not closed.From there we get into the AI acquisition arms race. China forced Meta to unwind its $2 billion Manus deal after it had already closed. Cohere signed a definitive agreement with Aleph Alpha at a reported $20 billion valuation. SoftBank launched roughly $11 billion in junk rated bonds to fund its next OpenAI check.Then politics. A new sanctions law gives the President tariff power of up to 100 percent on the biggest buyers of Russian oil, and the Supreme Court already reshaped tariff policy earlier this year. We cover what that means for how you underwrite a business with imported inputs.In the last segment Charles and I move the decimal. Every megadeal term has a Main Street twin: termination fees, ticking fees, key person risk, concentration risk, tariff clauses, and the new SBA 7(a) and 504 decoupling.Figures reflect reporting as of September 22, 2026. This is not investment, legal, or tax advice.LINKSTry Deal Flow OS free: https://dealflow-os.comNewsletter: https://buybuildexitwithroyredd.subst...Instagram: @buybuildexitFree Class: https://www.skool.com/buy-build-exit-...

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    58 mins
  • The Real Reason Big Tech Is Buying AI Companies: It's Not What You Think
    Sep 19 2026

    Six weeks ago Big Tech was buying AI companies. This month it stopped buying companies and started buying control points. In this no-guest reaction episode, Charles and I break down six real deals from the last two weeks and translate every single one into a move you can run on a 1 million to 5 million dollar business.The headlines call this an AI boom. It is a control grab. Every one of these deals is a company deciding it is cheaper to buy the bottleneck than to buy the business, and the deal on the front page is the same deal on your desk. You just move the decimal.What we cover:Nvidia licensing Groq and hiring the founder, and the DOJ probe now testing the reverse acquihire playbook. Salesforce assembling the customer conversation loop with Fin and the reported Listen Labs talks. Meta buying a nine person Swedish team to own the inbox. The agent security gold rush nobody is clicking on. Nvidia buying the open model marketplace with Hugging Face. And the cleanest roll up template on the board, Copart buying ACV.The operator takeaway in one line: buy the bottleneck, own the recurring workflow, buy the adjacency that makes your network worth more, and structure for the value that walks out the door with the seller. Same moves, fewer zeros.CHAPTERS0:00 Cold open, buy the bottleneck3:00 The backdoor acquisition, Nvidia and Groq15:00 The customer conversation wars, Salesforce and Meta28:00 The hidden winners, agent security and infrastructure39:00 Nvidia buys the marketplace, Hugging Face47:00 The boring deal every operator should study, Copart and ACV55:00 Rapid fire59:00 Close, move the decimalLINKSTry Deal Flow OS free: https://dealflow-os.comSubscribe to my newsletter: https://buybuildexitwithroyredd.subst...Follow me on Instagram: @buybuildexitFree Class: https://www.skool.com/buy-build-exit-...

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    59 mins
  • SBA Buyers, Wake Up: $85 Billion in Megadeals Just Rewrote Your Playbook
    Sep 11 2026

    Six megadeals. One week. One playbook every acquisition entrepreneur needs to run.In this reaction episode, Charles and I break down the biggest week in M and A this year, and we translate every single deal from Wall Street numbers into Main Street mechanics. If you are an SBA buyer, a lower-middle-market operator, a lender, or an owner thinking about your exit, this one is for you.Here is what we cover:Nvidia agreed to buy Hugging Face for roughly thirteen billion dollars. We break down why the buyer wanted the default distribution layer, not the technology, and how that same question applies to a three million dollar plumbing acquisition.NextEra and Dominion shareholders approved a sixty-six point eight billion dollar all-stock combination that would create the largest regulated electric utility in the country. Vertiv agreed to buy UtilityInnovation Group for one point four five billion in cash plus a big earnout. Both deals point to the same Main Street opportunity: boring trades businesses that serve utilities and data centers just became strategic assets.Chime announced it is buying Stride Bank for five hundred ninety million dollars in cash, ending a seven-year sponsor-bank relationship. Charles uses this to walk through the July 4, 2026 SBA policy notice that decoupled the 7(a) and 504 program limits. If you have not updated your capital stack thinking, you are leaving money on the table.Charter closed its thirty-four point five billion dollar combination with Cox, creating a thirty-seven million customer footprint across forty-five states. Bending Spoons agreed to acquire Airtable at a valuation well below its 2021 peak. Bain Capital agreed to buy Gong cha at a reported price of more than six hundred thirty-five million dollars, and Riverview Landscapes just closed its twenty-sixth acquisition since 2022.Same playbook. Different zeros. That is the whole game.We finish with a ten-question rapid fire, one takeaway from each host, and a close on the one lesson every one of these deals is telling you at the same time.If you got value out of this episode, subscribe, drop a comment on which segment landed hardest, and share it with the buyer in your network who needs to hear it.LINKSdealflow-os.comhttps://buybuildexitwithroyredd.subst...IG: @buybuildexitFree Class: Buy Build Exit Academy — https://www.skool.com/buy-build-exit-...

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    1 hr and 3 mins
  • M&A Is Back: The $111 Billion Megadeal and the Main Street Deals Nobody Is Bidding On
    Aug 19 2026

    Ten thousand boomers a day are aging toward an exit, and four hundred miles up the coast a 111 billion dollar media merger is bleeding money because it cannot get out of its own way. Same week, same country, same question underneath both. In this one Charles and I skip the guest chair and just read the tape on what is actually hot in M&A right now.We break down the Paramount and Warner Bros. Discovery megadeal as a bellwether, not gossip, because whatever regulators allow at the top sets the tone all the way down to your desk. Then we make the turn that matters for our audience, the lower middle market, where deal volume just hit a record and the boomer wave keeps feeding supply. We cover the timing mismatch that breaks even a great deal on paper, the disclosure discipline that scales from a corner store to a 111 billion dollar merger, the real math behind SBA change of ownership financing, and the honest two sided debate on private equity roll ups on Main Street.My whole thesis in one line: the deal on the front page and the deal on your desk are the same deal. Just move the decimal.What we get into:The megadeal returns and why the guardrails here matter to youThe timing mismatch hiding in a Hollywood storyFees, conflicts, and related party optics you have to priceWhy record dry powder is not the same thing as demandThe SBA numbers first time buyers get wrongRoll ups, are they saving Main Street or strip mining itIf this makes you rethink one deal on your desk, we did our job.Deal Flow OS: https://dealflow-os.comSubstack: https://buybuildexitwithroyredd.subst...Instagram: @buybuildexitFree Class, Buy Build Exit Academy: https://www.skool.com/buy-build-exit-...

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    56 mins
  • Buying a Business in 2026: Richard Parker on Seller Financing vs SBA Debt
    Jul 29 2026

    In this episode I sit down with Richard Parker, founder of Diomo Corporation and author of How To Buy A Good Business At A Great Price. Richard has personally bought 14 businesses over more than 35 years, he was hired by the Dalio family to mentor one of Ray Dalio's sons on buying small businesses, and he has built one of the most widely read buyer education resources in the world.This one is a real debate. Richard is a buy-side skeptic who leans hard on seller financing, and most of you watching make your living on SBA and bank debt. So we put him in the room and let him make his case. We get into why he tells buyers to fall in love with the profit and not the product, how he actually values a business, why he says most listings are overpriced and carry hidden problems, and what separates the small group of people who close from the ones who look for years and never buy.Charles and I also walk through what has changed in the market this year, from larger SBA borrowing capacity to the shift toward cash flow underwriting, and we pressure test whether cheaper and bigger capital makes buyers better or just makes it more expensive to be wrong. The figures Richard shares are his own numbers from his own track record, so take them as his experience, not a promise about your deal.If you are trying to buy your first business or your next one, this is the honest conversation about risk, discipline and financing that I wish more people were having.Chapters0:00 Cold open1:30 Welcome and guest intro4:00 Origin story and buy vs build philosophy12:00 Why now: the boomer wave and the bigger SBA checkbook20:00 Valuation and the Diomo method30:00 The financing fault line: seller financing vs SBA40:00 Due diligence, quality of earnings and the landmines48:00 Buyer psychology: why most never close54:00 Rapid fire58:00 CloseTry it free - https://dealflow-os.comSubscribe to my newsletter - https://buybuildexitwithroyredd.subst...Follow me on Instagram - @buybuildexitFree Class - https://www.skool.com/buy-build-exit-...

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    1 hr and 11 mins
  • The E-Myth Author Michael Gerber on Why SBA Lenders Fund Failing Businesses
    Jul 26 2026

    Michael E. Gerber wrote The E-Myth Revisited forty years ago and it has sold millions of copies since. Inc. Magazine calls him the world's number one small business guru. In this episode I sit down with Michael alongside my co-host Charles Oglesby to ask the question every lender should be asking: why do most of the businesses we finance fail, and what separates a bankable business from a well-paid job with overhead?We cover the entrepreneurial seizure and why the technician who makes the pies should almost never own the pie shop. We dig into why documented systems are not just an operations idea but an underwriting standard, and how the SBA's move away from credit scores toward cash-flow fundamentals lines up with what Michael has been saying for four decades. With SBA loan limits expanding dramatically, we ask whether more capital for Main Street is a blessing or a loaded gun, and what has to change inside a business before it can responsibly carry serious debt.We also get into the acquisition wave, what a buyer actually owns when all the systems live in the seller's head, the due-diligence version of the E-Myth, whether AI finally solves the systems problem or just automates the seizure, and Michael's unfinished mission to transform small business worldwide.If you lend to, advise, buy, or run a small business, this one is required listening.Deal Flow OS: dealflow-os.comNewsletter: https://buybuildexitwithroyredd.subst...Instagram: @buybuildexitFree Class, Buy Build Exit Academy: https://www.skool.com/buy-build-exit-...

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    50 mins