Why Self-Funded Search Is Harder Now and How to Stand Out as a Business Buyer

Why Self-Funded Search Is Harder Now and How to Stand Out as a Business Buyer

Sam Rosati, Kaustubh Deo, and Jacob Hall explore the evolving challenges of self-funded search on The Intentional Owner. Jacob Hall runs Kando Capital, a minority equity investor focused on self-funded searchers, and teaches entrepreneurship through acquisition at the University of Texas. His operational background includes Fortune 500 turnarounds and firsthand experience uncovering embezzlement in a small business. The conversation addresses how the playbook that worked from 2019 to 2021, max leverage, wide-open geography, hockey stick projections, no longer matches today's market reality. Interest rates have risen, competition has intensified, and buyer awareness has exploded without a corresponding increase in buyer preparedness. They discuss: - Why searchers must define a specific edge rather than treating any quality business as a fit - How emotional intelligence and transparency matter more than credentials when diligencing people - The underestimated difficulty of operating a small business compared to corporate work - Why geographic constraints can become advantages if leveraged through in-person relationship building - The gap between romanticized perceptions of business ownership and the visceral reality of layoffs, cash constraints, and daily firefighting This episode offers a clear-eyed view of search for anyone considering leaving a stable career to buy and operate a small business. Topics: (00:00:00) - Intro (00:02:32) - Introducing Jacob (00:04:14) - Jacob's path from operations to investing (00:10:26) - How Kando Capital works (00:11:29) - Deal flow and investment pace (00:18:00) - Why the old search playbook doesn't work (00:20:30) - The Four Horsemen of search challenges (00:27:00) - Running a business is harder than it looks (00:30:12) - What separates successful searchers (00:33:30) - The importance of EQ over IQ (00:35:43) - Diligencing the people side (00:46:14) - Preparing searchers for reality (00:51:54) - Finding your edge as a searcher (01:01:23) - Geographic constraints as an advantage (01:08:50) - The pep talk for searchers Speaker Profiles:   Sam Rosati     LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/ [https://www.linkedin.com/in/sam-rosati-68787a8/]     Twitter / X — https://x.com/Sam_Rosati [https://x.com/Sam_Rosati]     Website — https://www.samrosatismb.com/ [https://www.samrosatismb.com/]   Kaustubh Deo     LinkedIn — https://www.linkedin.com/in/kaustubh-deo/ [https://www.linkedin.com/in/kaustubh-deo/]     Twitter / X — https://x.com/guessworkinvest [https://x.com/guessworkinvest]     Substack - https://bigdealsmallbusiness.substack.com/ [https://bigdealsmallbusiness.substack.com/]  Jacob Hall     Kando Capital - https://www.kandocapital.com/ [https://www.kandocapital.com/]     LinkedIn - https://www.linkedin.com/in/jacobhall01/ [https://www.linkedin.com/in/jacobhall01/] Sponsors:   NewCo Risk — https://newcorisk.com [https://newcorisk.com]   Bay Business Group — https://bay-biz.com/ [https://bay-biz.com/]

Capital Efficiency & Getting to Scale: The Real Cost of Starting From Scratch

Sam Rosati and Kaustubh Deo explore when it makes sense to start a business rather than acquire one on The Intentional Owner. The conversation stems from a listener question about the rising difficulty of self-funded search deals, higher multiples for even small businesses, and whether starting from scratch might be a better path forward. They examine the economics of buying a single-crew service business versus building one, the fragility inherent in very small operations, and the underappreciated challenges of replacing an owner who serves as both technician and manager. They discuss: - Why the payback period on small acquisitions often exceeds the multiple paid plus a year - How margins degrade when transitioning from owner-operated SDE to a true EBITDA business - The case for working in a trade before starting versus relying on sales and marketing skills alone - Whether the rise of solo entrepreneurship enabled by digital tools shifts the calculus away from traditional search This episode offers a practical framework for aspiring owners evaluating whether to buy an existing business or build something new in an increasingly competitive acquisition market. Topics: (00:00:00) - Intro (00:06:00) - The start versus buy debate for small businesses (00:10:30) - Personal objectives drive the decision (00:15:30) - Comparing single-crew acquisition costs (00:18:30) - The debt payoff timeline versus startup growth (00:19:30) - The margin degradation of growth (00:20:46) - Breaking even in year one of a startup (00:23:27) - Buying bigger versus smaller (00:37:00) - The fragility of very small businesses (00:47:00) - The solopreneur alternative (00:49:00) - Agency versus financial independence (00:55:20) - Book recommendations and wrap-up  Sam Rosati     LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/ [https://www.linkedin.com/in/sam-rosati-68787a8/]     Twitter / X — https://x.com/Sam_Rosati [https://x.com/Sam_Rosati]     Website — https://www.samrosatismb.com/ [https://www.samrosatismb.com/]   Kaustubh Deo     LinkedIn — https://www.linkedin.com/in/kaustubh-deo/ [https://www.linkedin.com/in/kaustubh-deo/]     Twitter / X — https://x.com/guessworkinvest [https://x.com/guessworkinvest] Sponsors:   NewCo Risk — https://newcorisk.com [https://newcorisk.com]   Bay Business Group — https://bay-biz.com/ [https://bay-biz.com/]

The Guide to Information Sharing w/ Employees for SMB Owners

Kaustubh Deo and Sam Rosati unpack the complicated balance between transparency and confidentiality as small business owners managing growing teams. They explore how much financial and operational information should actually be shared with employees, where the line exists between helpful transparency and unnecessary stress, and why many owners unintentionally create confusion by failing to define what information is confidential. The conversation moves beyond theory into practical examples from their own businesses, including SBA debt, KPI dashboards, compensation structures, equipment purchasing decisions, and the realities of managing perception inside small companies. They also discuss how the search fund playbook has changed dramatically since 2021 and why many traditional acquisition assumptions no longer work in today’s market. They discuss: • The tradeoffs between transparency and oversharing with employees• Why KPI visibility should align directly with what each team member can control • How SBA debt and rising interest rates shape owner decision making• The danger of employees making assumptions when owners communicate too little • Why equity compensation often fails to create “owner mentality” in small businesses • The importance of clearly defining what information is confidential internally • How today’s acquisition environment differs from the low-rate search fund boom years • The four “horsemen” of bad deals in the current ETA market This episode is valuable for operators, searchers, and small business owners trying to build trust with teams while navigating the financial realities of ownership. Support our Sponsors: NewCo Risk gives SMB businesses access to the same bespoke approach, sophisticated strategies and big thinking as the leading global insurance consulting firms. Learn more @ https://www.newcorisk.com/ [https://www.newcorisk.com/] Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses.  Learn more at ⁠https://bay-biz.com [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [https://x.com/Sam_Rosati] Topics:

Durability vs. Growth in Small Business Ownership

Kaustubh Deo and Sam Rosati examine the hard tradeoffs that come with building a service business for durability instead of chasing the highest possible annual earnings. They discuss Q1 planning, seasonality, backlog pressure, pricing strategy, crew utilization, and the operational leverage that shows up when a business adds capacity without adding overhead. Kaustubh walks through how he is thinking about seasonal pricing, commercial work, delegation, and the choice to optimize for a well-run business that can still exist 10 years from now. They discuss: * Why seasonal pricing may matter more than blanket advice to raise prices * How adding a fourth crew changes margin math, capacity planning, and backlog pressure * The tradeoff between higher annual earnings and a smoother, more durable business * Why owner bottlenecks often remain in HR, accounting, sales meetings, and growth systems * How commercial work, pricing discipline, and delegation can support the path to a five-crew business Support our Sponsors: NewCo Risk gives SMB businesses access to the same bespoke approach, sophisticated strategies and big thinking as the leading global insurance consulting firms. Learn more @ https://www.newcorisk.com/ [https://www.newcorisk.com/] Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses.  Learn more at ⁠https://bay-biz.com [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [https://x.com/Sam_Rosati] Topics: (00:00:00) - Intro (00:03:01) - Listener Questions Grab Bag (00:04:01) - Why Q1 Feels Brutal (00:06:06) - Seasonality And Lead Gen (00:12:30) - Vacation Backlog Problem (00:13:59) - Recurring Meeting Cleanup (00:15:08) - Sales Meeting Bottleneck (00:16:37) - Can AI Replace You? (00:19:27) - Seasonal Pricing Strategy (00:31:01) - Scale Vs. Price Hikes (00:32:19) - Seasonal Layoffs Dilemma (00:38:50) - Choosing Stability Over Peaks (00:40:17) - Service Adjacencies Brainstorm (00:53:24) - Sales Systems And Constraints

Buying a Remote Business Through Self-Funded Search

Sam Rosati and Kaustubh Deo are joined by Vince and Kalyn Saulsberry-Fong to share the story behind acquiring a niche data business as a married couple. They walk through their transition from corporate careers into entrepreneurship, the intentional planning that led to their search, and how they aligned their business goals with their personal priorities. The conversation highlights their highly specific investment thesis around proprietary data, the unexpected challenges they faced post-close, and how they are thinking about building a scalable, automated business while preparing for a major life transition. They discuss: * How Vince and Kalyn transitioned from corporate careers into a joint search and acquisition journey * Why proprietary data became the foundation of their highly targeted investment thesis * The process of finding and acquiring a remote healthcare data business through a direct seller connection * Lessons from early ownership including working capital surprises and operational realities * How they are balancing business ownership, automation, and preparing for their first child Support our Sponsor: NewCo Risk gives SMB businesses access to the same bespoke approach, sophisticated strategies and big thinking as the leading global insurance consulting firms. Learn more @ https://www.newcorisk.com/ [https://www.newcorisk.com/] Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses.  Learn more at ⁠https://bay-biz.com [https://bay-biz.com] Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com [kd@sunthra.com] and they will answer them on the Pod!  Links: Kaustubh on Substack - https://bigdealsmallbusiness.substack.com/p/read-me-first [https://bigdealsmallbusiness.substack.com/p/read-me-first] Sam on X - https://x.com/Sam_Rosati [https://x.com/Sam_Rosati] Links: Kalyn on LinkedIn - https://www.linkedin.com/in/kalynsaulsberry/ [https://www.linkedin.com/in/kalynsaulsberry/] Vince on LinkedIn - https://www.linkedin.com/in/vince-saulsberry-fong/ [https://www.linkedin.com/in/vince-saulsberry-fong/] Audience Synergy - https://audiencesynergy.com/ [https://audiencesynergy.com/] Topics: (00:00:00) - Intro (00:02:17) - Meet Vince and Kalyn (00:10:02) - Vision planning and goals (00:21:34) - Search thesis and buy box (00:27:18) - Audience synergy explained (00:30:52) - The catch and founder fit (00:32:42) - Monetization and revenue mix (00:35:27) - Data diligence and margins (00:37:41) - Finding the deal fast (00:41:25) - Direct seller negotiations (00:44:54) - Self funded search reality (00:46:53) - Day one transition plans (00:49:12) - Channel partners onboarding (00:51:20) - Working capital surprises (00:55:14) - Pregnancy and operations (01:01:03) - Automation and ai systems (01:09:24) - Spouse partnership dynamics (01:13:31) - Wrap and sponsor reads