Behind Connoisseur Media’s pending acquisition of Alpha Media, you won’t find a blockbuster cash price. The real economic engine of the transaction is Connoisseur’s willingness to refinance Alpha’s debt, believed to be sizable even after the company’s 2021 bankruptcy restructuring.
In an FCC filing outlining their Stock Purchase and Exchange Agreement, at the heart of the Connoisseur/Alpha deal is a broad, multi-step transaction that includes the full repayment and retirement of Alpha’s outstanding obligations, including debt carried forward from its Chapter 11 proceedings.
In early 2021, Alpha Media entered Chapter 11 with a prepackaged plan to restructure $267 million in debt. That plan saw $72.6 million in second-lien debt converted to equity and the replacement of $90 million in first-lien debt with a $115 million financing package designed to both pay off the old loan and inject new capital into the business.
Based on court records and public disclosures, Alpha exited bankruptcy with an estimated $115 million in debt, though the precise number may have grown in the years following. The 2025 purchase agreement does not disclose a hard dollar figure for the debt Connoisseur assumed, but confirms that multiple existing credit agreements, including those with Brigade Capital, Citizens Bank, and ICG, were fully repaid and terminated at closing. These repayments were made using proceeds from newly arranged credit facilities under the Connoisseur umbrella.
To facilitate the transaction, Alpha’s owners reorganized into a holding entity called Newco Seller. That entity contributed 100% of Alpha Media’s equity to Connoisseur in exchange for a 3.75% minority equity stake, plus two warrants that allow for the purchase of an additional 10% of equity under specific valuation thresholds.
The warrants – one exercisable at a $30 million valuation for Connoisseur, the other at $70 million – suggest a blended implied equity valuation of around $34 million, presenting future upside for Alpha’s former stakeholders.
The deal is expected to close in late 2025, pending FCC approval. A Local Marketing Agreement took effect on May 5 for Alpha’s 207 stations.
As previously announced, the combined Connoisseur will continue to be led by CEO Jeff Warshaw and position the company among the top 10 US radio groups by revenue and station count, with 218 stations across 47 markets.
Glass half full or half empty? All problems come wrapped in their solutions. So the new guys will have to decide if they want to be part of the solution or part of the problem. The odds are stacked against them, but there is a solution if they have the guts to make it happen and the experience and wisdom to know which way out of the jungle.
Would would someone please jump in and help him make this decision NOT to do this move. I don’t know any business advisor manager would advise anyone to invest in any radio group of this magnitude in this day and age. It’s not 1980 or 1990 anymore….save him from himself.
I agree. Terrible move that is headed to disaster. Alpha has too much baggage and is hated in the communities. Alpha ruined a really great concept with the stations they purchased from Dean Goodman in 2007. Dean Goodman had inherited that ‘community’ atmosphere from the Shepherd Group. It took decades to build those stations and earn the trust of the community through results. Alpha totally destroyed it. If Connoiseur had been smart they would have visited some of the communities and seen the damage and distrust that has emerged from many of them. Maybe not all, but a lot of them.
You have to respect Jeff’s incredible courage, tenacity, and belief in radio by taking on 207 more radio stations, but this is a familiar industry story and far too often, it doesn’t end well. Since 1996, there have been numerous attempts to consolidate highly profitable local radio stations and combine their collective revenue streams…followed by lots of red ink, mass layoffs, desperate mergers, abrupt management reshuffles, financial shell games and a string of chapter 11 bankruptcies. The blame is often placed on irresponsible amounts of debt. It’s an easy shot to take, but is it really that simple? Here’s my take:
I think these radio group financial failures are the result of an industry composed of small, loosely run businesses (local radio stations) that rarely had uniform cultures of excellence inside them, rarely embraced the concept of best practices and process improvement in every department and were rarely led by managers who knew what a key performance indicator was or how to design them and use them. A lot of them barely finished high school. Instead, once upon a time, you were hired in radio if you were considered fun–and had a set of golf clubs. That was about it. I’m not sure it’s evolved much since then. Knowing what we know now, does buying a bunch of radio stations today seem like “easy money” or a collosal undertaking with plenty of things that could go wrong?
I come from the sales management side, so let me take some personal responsibility here and look in the mirror for a minute. I think it’s time to be brutally honest about the quality of your sales process, or lack thereof. I thought about it and it prompted me to make some major changes and they all paid off. You can’t just go out and “wing it.” You need a legitimate plan.
Consistent, robust revenue growth is the cure. It doesn’t matter what the ailment is. When you grow revenue each quarter, your list of problems gets a lot shorter or disappears. The question is, “What is your sales process to grow revenue?” How are you preparing, equipping, supporting and empowering your sellers and managers to succeed in building long-term, lucrative partnerships with clients? Hint: It involves way more than just handing out a budget and a laptop. The “sink or swim” technique of training radio sales people and sales managers was pretty outdated in 1961, but it’s downright insane in 2025. It’s the sure path to failure. So, why is it still embraced today? Why did we used to smoke cigarettes on planes?
I see the first quarter revenue results coming in. You tell me—are the largest companies in the radio industry delivering robust OVERALL first quarter revenue growth today, or is it a little disappointing out there? Lackluster revenue performance is the result of a lackluster sales process. They’re inseparable. You can try to “spin” poor sales performance by listing all the categories that are “down” but there is always a mixture of up and down categories, so that’s a pretty weak excuse.
Consider this: Facebook (Meta) generated $164.5 Billion in revenue in 2024 and $62 billion in profit! Google (Alphabet) generated $349.8 Billion in revenue in 2024 and $100 billion in profit! How much money did advertisers entrust to radio in 2024? A lot LESS. Have you ever seriously wondered why? You should. People spend money with the companies that earn their respect and deliver results. See where I’m going?
Meta and Alphabet carefully train and support their sales teams with a world-class sales process designed to deliver a pristine customer experience to build long term customer relationships. Can the same be said for radio groups today? Can you appreciate the irony of the commercial radio industry not investing more time, effort and energy into improving its overall ability to sell commercials?
CEO’s, if you think your current sales process is really “dialed in” even though it’s not generating conistent revenue growth, here’s a crazy idea: Pick up the phone and call some clients. Ask them how your sales team can do a better job of helping them achieve their goals. Trust me. They’ll tell you. They’ll also respect you immensley for making that call. It’s a win / win. You’ll also understand how far short of “dialed in” your sales process really is right now and how you can improve it immediately. The less you know about how your own sales process is resonating with clients, the more vulnerable you’ll be to lackluster performance. It’s also pretty simple to spot: If your sales are declining, there’s a sales process problem. Period. So, investigate “why” with your clients.
Jeff, you’re an extremely accomplished industry leader and if you make this Alpha deal work, it will be a landing on the moon moment in radio—and the entire industry will be better for it. I, for one, really hope you do. The industry needs a “win” right about now and this is a perfect moment to deliver one and start a rally. I’m rooting for you!
This is not going to result in better local radio for the majority of the acquired markets. The smaller the market, the worse it will be.
Buying a business that’s in a hole so you can turn it around is one thing. But the vast majority of the acquired markets are not strong enough to float this kind of debt.
Do they have the infrastructure to run 210 stations across the country? All they’ve operated was 10 stations in the same region and now they’re going coast-to-coast. Oh my.
Can they turn it around? Most of these stations have had multiple ownership changes over the past 20 years and have struggled mightily to keep the lights on. There’s nothing special about Connoisseur Media that I’ve seen that leads me to believe that they have the answer.
That’s why this one no longer looks like a hole, it resembles an impact crater. Once all the dust hits the air, Connoisseur Media will face the same fate as the dinosaurs.
This is now like the dumb and dumber of the radio industry…. Should be another fun one to watch fold and for one fool to overpay.
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