Beware the Relentless Middlemen: How to Avoid Being Held Hostage in Your Own Business
In 2025, the entrepreneurial landscape is more connected yet more complex than ever—and the old problem of middlemen holding your business hostage remains stubbornly relevant. These middlemen aren’t just the traditional brokers or agents anymore; they’ve evolved into AI-powered platforms, automated agencies, and creator economy gatekeepers who expect a lifetime cut or perpetual favors in exchange for introductions or services.
The worst kind of middlemen are those who constantly remind you of past favors or “help” they provided, expecting you to pay them back forever—often at steep discounts or with free work. This is the business equivalent of a loan shark: you end up paying back 20 times over, long after the original favor. In today’s world, that might look like a platform taking a huge cut of your creator revenue indefinitely or an AI service that locks you into expensive subscription tiers under the guise of “exclusive access.”
When someone helps your business, send a genuine thank-you—whether that’s a lunch, a thoughtful note, or a small gift—to close the loop and signal that the favor is settled. This is crucial because if you leave the debt open-ended, you’ll never stop paying it back. In 2025, with AI and automation making business introductions and services more scalable, it’s easier than ever to fall into this trap if you don’t set clear boundaries.
Another modern twist is how some middlemen block you from direct access to your customers or clients—the “purse strings.” Whether it’s a platform algorithm controlling who sees your content or an agency that insists on being the sole contact point, don’t let anyone keep you from building a direct relationship with your audience or buyers. Your business thrives on direct connections; middlemen should facilitate, not gatekeep.
Remember, middlemen exist for a reason—they often provide expertise or access you don’t have. But the key mistake entrepreneurs make is ceding too much control to them. You need to lead these relationships, not be led. In negotiations, dial up your own involvement and dial down reliance on intermediaries. This is especially true when AI tools and automation can sometimes obscure who’s really in control of your business outcomes.
In short, don’t be a victim to relentless middlemen in 2025. Use technology and human connections wisely, set clear boundaries, and always keep your direct relationships front and center. Your business—and your sanity—depend on it.
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Kevin "KevRoss" Ross is a music and radio industry expert. He is a 20 -plus year entrepreneur with the leading most successful industry trade publication and site Radio Facts (www.radiofacts.com). He has also published various books, magazines, performed marketing and promotions for major corporations and recording artists and he is on the advisory board of several industry organizations. This year Ross introduced his non profit organization LOMARI (Leaders of the Music and Recording Industry) to help teach young minority students how to market and manage their music and products.
