In the world of business exits, we often focus on the transaction. The reality is that the strongest exits are built years before a company ever goes to market.

In this episode of the Selling Successfully Podcast, Jim sits down with Dan Holstein, award-winning business coach at Kaizen Performance Improvement Corp, to explore how coaching helps owners build stronger, more scalable, and more transferable businesses long before a sale is on the table.

They discuss:
• What pre-sale readiness really means
• The operational discipline required to build optionality
• The most common risks in founder-led companies
• How coaching reduces owner dependency and strengthens leadership teams
• Why the strongest exits are earned, not timed

Jim and Dan also share a real client story about how coaching transformed a business and laid the foundation for a successful exit once Portage became involved.

If you are a business owner thinking about scaling, succession, or selling in the future, this conversation will reshape how you think about preparation.

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In this episode, Jim from Portage joins Kevin Laleyan from PE Gate for a conversation on what drives successful transactions in today’s lower middle market.

They discuss the common pitfalls buyers encounter and why both buyers and sellers need the right team in place to properly implement systems and processes after a deal closes. Alignment between both sides is essential, and PE Gate explains how they help uncover shared objectives and create clarity when navigating complex transactions.

The discussion also explores PE Gate’s flexible approach to deal structuring, including minority investments, rolled equity, vendor take-back financing, and majority ownership. By identifying operational weaknesses early and putting real skin in the game, PE Gate partners with management teams to build stronger businesses and work toward a successful exit.

Together, Portage and PE Gate focus on the lower-middle market, ensuring sellers are matched with buyers who are not only qualified, but truly the right strategic fit.

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In this episode, Nick Olsen, Managing Director at Cornerstone International Alliance (CIA), joins Jim to discuss how global buyer networks and data intelligence are transforming the M&A landscape. He shares insights on CIA’s role in the market, the scope of its international buyer network, and how data-driven strategies empower more efficient deal-making. We also explore how CIA’s reach enhances Portage’s sell-side process, hear examples of successful cross-border engagements, and get advice for business owners preparing for a sale. Packed with practical insights and forward-looking perspectives, this conversation offers a clear view of the strategic value behind buyer intelligence.

Thank you for listening!
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