Kaustubh Deo and Sam Rosati return for a conversation on blending lessons from recent industry conferences with a deep dive into the financial realities of running a small business. Drawing from Kaustubh’s experience speaking at an arborist conference and Sam’s perspective on using events for networking and deal flow, they explore how conferences can reinforce professional credibility and open new opportunities. From there, the discussion shifts toward capital structure, liquidity, and risk management—offering practical insights into how owners can balance leverage, cash reserves, and personal investing to build more resilient companies.

They discuss:
• How industry conferences can strengthen brand reputation and open new doors
• Why liquidity often matters more than lowering leverage in small business acquisitions
• Structuring debt and equity for long-term stability and optionality
• Managing cash flow swings and working capital through changing market conditions
• How operators think about inflation, investing, and personal risk alignment

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The Kalmar Group is a recruitment firm who partners with small business owners around the nation to find Manager to VP level hires in sales, marketing, operations, and finance across multiple niche industries. 

Website: https://www.thekalmargroup.com

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Links:

Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first

Sam on X - https://x.com/Sam_Rosati

Topics:

(00:00:00 ) - Intro
(00:01:33 ) - Catching up
(00:04:23 ) - Arborist conference insights
(00:06:10 ) - The value of industry conferences
(00:10:03 ) - Networking and education
(00:12:54 ) - Leadership and industry engagement
(00:24:57 ) - Conference strategies for searchers
(00:31:31 ) - Building industry relationships
(00:39:07 ) - Discussing Seattle's climate and business potential
(00:40:09 ) - Approach to business leverage and debt
(00:50:56 ) - Personal finance strategies and investments
(01:04:45 ) - Sports and networking benefits
(01:09:51 ) - Closing thoughts and fun facts