July 30, 2026

207: Gregory Kovsky: "The Hidden Barriers To Becoming a Real Business Broker"

207: Gregory Kovsky: "The Hidden Barriers To Becoming a Real Business Broker"
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With Guests

Selling a business is often the largest financial transaction of an entrepreneur’s life—but according to Gregory Kovsky, most business owners underestimate how complex the process really is.

In this conversation, Erik sits down with Gregory Kovsky, President and CEO of International Business Associates (IBA), to unpack the realities of business brokerage, M&A advisory, and what separates elite dealmakers from average brokers. Gregory shares lessons from more than 30 years in the industry, including why so many businesses never sell, how experience changes outcomes, and why communication—not information—is often the most valuable asset in a transaction.

Along the way, they explore negotiation, AI, leadership, business evolution, and the surprising similarities between business brokerage and heart surgery.

👤 About the Guest

Gregory Kowski is President and CEO of International Business Associates (IBA), the Pacific Northwest’s oldest and largest business brokerage firm. With 30+ years of experience and 300+ personal transactions, he leads a team across 10 offices in Washington and Oregon and has helped complete 4,400+ deals. He blends brokerage, finance, and licensing expertise, and publishes and speaks on buying and,

🧭 Conversation Highlights

  • Why barriers to entry are too low for what business brokerage actually demands
  • The “three tiers” of communication: articulate, educate, persuade
  • A broker’s job is to spot yellow flags, then pull in the right experts fast
  • Industry-specific nuance and process discipline matter for long, emotionally loaded retirement exits

💡 Key Takeaways

  • Business brokerage is not one skill. It spans accounting, taxes, finance, law, insurance, real estate, licensing, and psychology.
  • A good broker is a facilitator: recognize risk, educate clients, and coordinate experts, not claim omniscience.
  • Communication wins deals: clarity in the moment, plus referenceable written materials.
  • Screen brokers like you’d screen a surgeon: track record, specialization, and experience under pressure.

❓ Questions That Mattered

  • What should the minimum licensing and continuing education bar be for business brokers to match the complexity of the work?
  • Why do so many deals fail or leave sellers regretting the outcome, and what predicts those outcomes?
  • How is technology and AI changing information asymmetry in business sales, and why does lived execution still matter?
  • How should an entrepreneur vet a broker: personal trust, firm scale, and industry-specific experience all at once?

🗣️ Notable Quotes

  • “A good business intermediary needs diverse knowledge and experience to professionally represent their client.”
  • “Our job is to get people to shake hands.”
  • “If you don’t know about them, if you don’t understand them, how can you guide a client through that sale process?”
  • “There’s nothing good that happens from forcing anything.”

🔗 Links & Resources