The Intentional Owner

Sam Rosati and Kaustubh Deo explore the value of implementing a structured business operating system as a first-time owner on The Intentional Owner. Many entrepreneurs navigate the chaos of early ownership without clear long-term objectives or a framework to break them down into manageable steps. The conversation centers on how tools like the Entrepreneurial Operating System can help owners move from reactive firefighting to intentional execution, even if a lighter version makes more sense for smaller teams.

They discuss:

- Why most new owners operate rudderless for months or years without written objectives

- How core values function as daily decision-making rubrics for hiring, firing, and operations

- The difference between aspirational three-year goals and achievable one-year plans

- Whether weekly accountability meetings make sense before you have a real leadership team

- How defining your ideal customer profile prevents the trap of chasing every opportunity

This episode offers practical insight for small business owners trying to bring structure to chaos without overwhelming their already stretched teams.

Topics:

(00:00:00) - Intro

(00:05:12) - Why first-time owners need an operating system

(00:07:51) - Breaking down EOS and goal-setting frameworks

(00:09:31) - When to implement a vision for your business

(00:10:47) - Learning vision the hard way

(00:15:19) - Core values as decision-making tools

(00:19:48) - The BHAG debate

(00:26:00) - Defining your target market

(00:30:02) - Pure EOS versus EOS lite

(00:31:05) - Weekly L10s and quarterly rocks

(00:35:08) - Three-year vision and cascading goals

(00:45:19) - Making the framework work for you

(00:46:24) - Tampa happy hour announcement

Speaker Profiles:

Sam Rosati

LinkedIn —https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X —https://x.com/Sam_Rosati

Website —https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn —https://www.linkedin.com/in/kaustubh-deo/

Twitter / X —https://x.com/guessworkinvest

Substack -https://bigdealsmallbusiness.substack.com/

Sam Rosati and Kaustubh Deo explore the realities of managing change in small businesses on The Intentional Owner. The conversation begins with Kaustubh sharing recent observations about business owners who've grown rapidly through relentless change implementation, prompting a discussion about sustainable versus aggressive growth strategies. Sam and Kaustubh examine how an owner's tolerance for chaos shapes team capacity and business trajectory, using real examples from the home services industry.

They discuss:

- How personality determines whether fast-paced change or methodical implementation works better for a given business

- The tradeoffs between sequential process improvements and ripping the Band-Aid on major transitions

- Why acquiring companies at maximum capacity requires building systems before pursuing growth

- Kaustubh's experience testing four-tens versus five-eights schedules across two locations during an integration

- The relationship between M&A activity and a team's bandwidth for other operational projects

This episode offers practical perspective for owners balancing growth ambitions with team stability and sustainable operations.

Topics:

(00:00:00) - Intro

(00:01:20) - Tampa happy hour and upcoming conference plans

(00:02:49) - Change management in small business

(00:05:21) - Portfolio approach vs full focus

(00:09:19) - How much change can a team handle

(00:14:15) - Why fast growers operate differently

(00:15:27) - Tolerance for chaos

(00:16:36) - Team churn and aggressive growth

(00:22:15) - Different growth stages need different skill sets

(00:25:12) - Communicating change internally

(00:26:48) - Predictability and team participation

(00:27:51) - Leading the team through acquisition integration

(00:30:03) - M&A as a constant overlay

(00:30:59) - Maintaining idle capacity for deals

(00:33:55) - Building ahead of the next acquisition

(00:35:14) - Thoughtful change enables more change

(00:35:55) - Would you decline a transformative deal

(00:37:33) - Slow is smooth smooth is fast

(00:40:02) - Early years transformation at Blooma

(00:40:30) - Removing yourself from every step

(00:42:38) - Why first years are chaotic for new owners

(00:45:35) - The four tens vs five eights experiment

(00:50:05) - Wrap up and EOS preview

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Kaustubh Deo and Sam Rosati explore what it takes to build a small business that can function without its owner at the center of every decision. They compare the early days of operating owner-dependent businesses with the systems, people, and processes that gradually create more independence. The conversation covers everything from payroll and pricing approvals to staffing redundancy, employee performance, and the challenge of letting go of responsibilities. They also discuss using time away from the business as a practical test for identifying weak systems and remaining bottlenecks.

They discuss:

•

How owner-dependent businesses evolve as responsibilities move from the owner to the team

•

Why building redundancy creates the capacity to handle turnover and performance issues

•

Using extended time away from the business to expose broken processes and bottlenecks

•

Why owners often hold onto underperforming employees longer than they should

•

How to approach conferences more intentionally through prearranged meetings and stronger industry relationships

This episode offers small business owners a practical framework for reducing owner dependency, strengthening their teams, and building companies that can operate more effectively without constant intervention.

Topics:

(00:00:00) - Intro

(00:01:41) - The value of peer advisors

(00:05:39) - Buying a house as a business owner

(00:09:53) - Can your business survive without you

(00:12:02) - What broke at day one

(00:21:40) - Building excess capacity into the team

(00:28:36) - Taking time off to test systems

(00:30:51) - The superpower of firing people

(00:40:06) - Using conferences strategically

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Sam Rosati and Kaustubh Deo discuss quarterly planning, team structure, and financial transparency on The Intentional Owner. Kaustubh is preparing for Blooma's first multi-person quarterly planning session, bringing together functional leaders who previously weren't involved in strategic projects. Sam shares how PSG has implemented EOS across multiple locations, including full-day quarterly sessions and weekly level 10 meetings. The conversation explores when to share P&L data with leadership teams, how to balance special projects with revenue objectives, and why small business financials can be too noisy for monthly reviews.

They discuss:

- How PSG structures quarterly planning sessions from taking stock through identifying 30 to 40 issues and prioritizing five to seven as quarterly rocks

- Why connecting special projects to measurable KPIs helps leadership teams understand their impact on the broader business

- Managing seasonality by timing operational improvements for slow periods while relationship-building happens year-round

- The trade-offs between staffing up aggressively during peak season versus artificially throttling growth to maintain team stability

This episode offers practical frameworks for owners managing seasonal businesses who want to involve their teams in strategic planning without overwhelming them with financial noise.

Topics:

(00:00:00) - Intro

(00:01:24) - Q4 planning and quarterly rocks

(00:02:20) - Implementing EOS across multiple locations

(00:04:56) - Breaking down strategy into weekly goals

(00:06:32) - Building a leadership team at Blooma

(00:11:56) - Planning the offsite agenda

(00:14:15) - P&L visibility for the team

(00:15:15) - Managing noisy small business financials

(00:16:01) - The quarterly planning structure

(00:19:51) - Issue identification and prioritization

(00:27:22) - Planning around seasonal business cycles

(00:33:13) - Special projects in slow seasons

(00:35:33) - Revenue as an output versus input

(00:38:36) - Reacting to slow quarters

(00:42:15) - Sales cycles and seasonal timing

(00:47:36) - Managing growth and staffing seasonally
Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Sam Rosati and Kaustubh Deo explore what makes a capable searcher and business owner on The Intentional Owner. They examine a recent tweet from investor Grant Hensel about green flags and red flags in assessing searchers—and quickly discover how difficult these qualities are to articulate. The conversation shifts to Kaustubh's operational journey at Blooma, where he's doubled revenue while building out a leadership team that now includes an operations manager, a production supervisor, and offshore support staff.

They discuss:

- Why raw intellectual horsepower matters less than learning ability and decision-making stamina

- How Blooma transformed from a 10-to-3 crew-to-office ratio into a nearly one-to-one structure, creating operating leverage for the next million in revenue

- The mechanics of skinning up working capital through systematic collections and managing a seasonal backlog against crew capacity

- Why Kaustubh reduced prices for the first time to keep crews efficiently full, and how that trade-off affects profitability

- The reality of refinancing seller notes and SBA debt when cash flow is tight and EBITDA hasn't yet caught up to headcount

This episode offers a candid look at the operational maturity required to scale a services business while managing leverage and seasonal demand.

00:00 - Intro

05:25 - Intelligence and small business success

08:25 - Managing people as an introvert owner

10:01 - Assessing searchers: green and red flags

12:09 - The it factor for searchers

16:42 - AI-generated materials and underwriting

22:26 - Backing into decisions you've already made

25:09 - Blooma update: operational maturity

26:39 - Building layers and delegating work

32:21 - Promoting yourself as the owner

34:27 - The cost of operational growth

37:07 - Step functions in scaling overhead

41:36 - Managing cash flow with leverage

42:02 - Skinning up working capital

45:02 - Considering a refinance

49:31 - Sales funnel and backlog management

53:54 - Understanding seasonality patterns

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Sam Rosati and Kaustubh Deo explore a question many small business owners face but rarely discuss: what size business should you actually build toward? The conversation examines the trade-offs between revenue growth, quality of life, and the evolving skill sets required at each stage of scale. Rather than assuming bigger is always better, they map out the distinct lifestyle and operational realities of running businesses at different revenue thresholds—from under $2 million to national multi-location operations.

They discuss:

- Why the $2–5 million revenue range often becomes a "trap size" where complexity outpaces profitability and the owner gets stuck in both visionary and integrator roles

- How buying a sub-$1 million business with minimal debt can yield $300–400K in annual owner earnings without the stress of scaling beyond local operations

- The specific operational and leadership transitions required to move from a single-location operator to a regional or national player, and why those transitions don't suit every owner's strengths or interests

- How debt structure and investor expectations fundamentally change what end state is realistic or desirable for a given acquisition

This episode, from The Intentional Owner, offers a framework for operators thinking honestly about where growth creates value and where it simply creates work.

(00:00:00) - Intro

(00:01:38) - Tampa meetup and fitness bet payoff

(00:04:16) - Small business owner attention to detail

(00:04:51) - The frame shop mistake story

(00:08:23) - How kindness works with small businesses

(00:13:51) - Managing priorities as a small business owner

(00:16:55) - Setting business size goals

(00:19:51) - The small local operator path

(00:22:56) - The trap size business dilemma

(00:27:16) - From revenue producer to manager

(00:30:30) - Getting out of trap size

(00:33:17) - The small business path without debt

(00:35:15) - Buying under one million in revenue

(00:36:00) - Two to five million as an end goal

(00:38:05) - Inflation and the changing trap size

(00:40:18) - Growing from five to fifteen million

(00:44:30) - PSG's geographic expansion strategy

(00:48:42) - Staying regional versus going national

(00:52:13) - Final thoughts on growth paths

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Sponsors:

Bay Business Group — https://bay-biz.com/

Sam Rosati, Kaustubh Deo, and Adam Markley explore the realities of small business ownership through the lens of investor pattern recognition on The Intentional Owner. Markley, who has spent a decade navigating the ETA ecosystem as a searcher, operator, and now investor, brings perspective from both sides of the transaction. The conversation challenges conventional wisdom about dealmaking and operator success, emphasizing that execution after closing determines outcomes far more than deal structure alone. While economic alignment matters, small businesses remain fundamentally owner-dependent, making operator capability the critical variable in creating value.

They discuss:

- Why strong communication during search signals future operational performance with customers and employees

- How seller financing and proper capitalization from the start change trajectory for first-time owners

- The difference between playing business and actually executing sales, employee retention, and revenue growth

- Why going bigger with less ownership can compound better than owning more of a smaller, undercapitalized business

- How irrational optimism gets people into deals but realistic expectation-setting determines who survives the first few years

This episode offers practical insight for anyone evaluating the gap between acquiring a business and successfully operating one over the long term.

Topics:

(00:00:00) - Intro

(00:03:22) - Adam Markley's ETA journey

(00:07:09) - UK acquisition dynamics and tax arbitrage

(00:09:28) - Lessons from buying and operating businesses

(00:10:32) - Operator fit versus deal quality

(00:13:19) - Why operators matter more in small business

(00:14:35) - Economic alignment in self-funded search

(00:20:34) - Investor case studies from 2024

(00:31:35) - Assessing operator quality and playbook depth

(00:35:20) - Post-close expectations and communication

(00:41:16) - Sales skills as a red flag indicator

(00:45:21) - Rapid fire: advice and resources

(00:47:19) - What Adam would do differently

Show Platforms:

YouTube — https://www.youtube.com/channel/UCnQQ0EBtTcZmNieNf0trvDw

Apple Podcasts — https://podcasts.apple.com/us/podcast/the-intentional-owner/id1797346741?uo=4

Spotify — https://open.spotify.com/show/0H5n91PR3c9RqyNAbh1AH9

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://twitter.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/kaustdeo

Adam Markley

LinkedIn — https://www.linkedin.com/in/adammarkley/

Twitter / X — https://x.com/adammarkleysmb

Companies:

NewCo Risk — https://www.newcorisk.com/

Bay Business Group — https://bay-biz.com/

Sam Rosati and Kaustubh Deo tackle capital allocation for small business owners on The Intentional Owner. The conversation examines four primary options for deploying excess cash: reinvesting in the business, repaying debt, returning capital to investors, and maintaining liquidity. Sam and Kaustubh explore the psychological pressure many owners feel to rapidly pay down SBA loans, the actual cost-benefit of debt reduction versus cash reserves, and why liquidity often trumps marginal return advantages in the early years of ownership.

They discuss:

- Why paying down term debt early can backfire without loan reamortization

- The real return delta between holding cash and eliminating debt or preferred equity

- How reinvestment often means absorbing P&L burn rather than big capital expenditures

- Whether buying operating real estate makes sense for small business owners

This episode offers a practical framework for owners managing the tension between financial optimization and operational resilience.

Topics:

(00:00:00) - Intro

(00:01:51) - Catching up and summer doldrums

(00:04:56) - Capital allocation for small business owners

(00:05:34) - The four buckets of capital allocation

(00:06:52) - Why you should prioritize liquidity first

(00:08:37) - Paying down debt vs holding cash

(00:10:12) - Understanding loan reamortization

(00:14:02) - Setting a liquidity waterfall

(00:15:55) - Returning capital to investors

(00:17:58) - Reinvesting in the business

(00:18:09) - What reinvestment actually looks like

(00:20:31) - The renter mindset for equipment

(00:22:52) - Real estate as the fifth bucket

(00:23:46) - Why most shouldn't buy real estate day one

(00:26:07) - Running the real estate purchase math

(00:32:53) - Long-term ownership and real estate value

(00:36:08) - Blending SBA loans with real estate

(00:37:55) - Investor expectations and tax distributions

(00:39:02) - Setting capital allocation expectations pre-close

(00:47:48) - Due diligence warning on real estate costs

Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Jacob Hall

Kando Capital - https://www.kandocapital.com/

LinkedIn - https://www.linkedin.com/in/jacobhall01/

Sponsors:

NewCo Risk — https://newcorisk.com

Bay Business Group — https://bay-biz.com/

Sam Rosati and Kaustubh Deo explore practical alternatives to traditional entrepreneurship through acquisition on The Intentional Owner. The conversation examines how small business ownership provides agency and flexibility that corporate careers rarely offer, especially as professionals enter their 30s and 40s and face competing life priorities. Rosati and Deo discuss buying very small businesses, the realities of work-life balance as an owner, and the mindset required to turn a fragile job into a sustainable enterprise.

They discuss:

- Why buying a business under $200,000 in earnings requires entrepreneurial vision to impose on a small operation

- How agency over time differs from reduced stress in ownership, especially when personal guarantees are involved

- The four models of franchise ownership and whether franchising offers comparable independence to self-funded search

- Why married couples may be better positioned to buy and grow micro businesses together

- How to evaluate franchise unit economics and territory strategies for building regional dominance

This episode offers a clear-eyed look at path options for aspiring business owners who face competitive deal markets or seek models that fit specific lifestyle goals.

(00:00:00) - Intro
(00:02:50) - Foster care and work flexibility
(00:03:35) - Finance career constraints versus ownership
(00:06:45) - Mid-career reckoning and ETA's appeal
(00:11:12) - Effort versus stress in ownership
(00:12:32) - Building resilience as risks evolve
(00:14:33) - Playing the long game
(00:15:33) - Alternatives to traditional ETA
(00:19:20) - Buying small as an entry strategy
(00:19:50) - Starting a business in your domain
(00:24:37) - Buying micro businesses as add-ons
(00:27:18) - Married couples as business partners
(00:31:10) - Imposing vision on small businesses
(00:34:30) - Franchising as an ETA alternative
(00:35:34) - Four franchise ownership models
(00:38:20) - Franchise startup costs and financing
(00:40:11) - Non-food service franchise opportunities
(00:40:31) - Evaluating royalty fees and brand value
(00:42:15) - Franchisor expectations and exit paths
(00:46:56) - Unit economics and franchise selection
(00:53:20) - Closing thoughts and sponsor messages
Speaker Profiles:

Sam Rosati

LinkedIn — https://www.linkedin.com/in/sam-rosati-68787a8/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Sponsors:

NewCo Risk — https://newcorisk.com

Bay Business Group — https://bay-biz.com/

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/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Substack - https://bigdealsmallbusiness.substack.com/

Jacob Hall

Kando Capital - https://www.kandocapital.com/

LinkedIn - https://www.linkedin.com/in/jacobhall01/

Sponsors:

NewCo Risk — https://newcorisk.com

Bay Business Group — https://bay-biz.com/

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/

Twitter / X — https://x.com/Sam_Rosati

Website — https://www.samrosatismb.com/

Kaustubh Deo

LinkedIn — https://www.linkedin.com/in/kaustubh-deo/

Twitter / X — https://x.com/guessworkinvest

Sponsors:

NewCo Risk — https://newcorisk.com

Bay Business Group — https://bay-biz.com/

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/

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

Links:

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

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

Topics:

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/

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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
(00:03:01) - 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

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/

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

Links:

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

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

Links:

Kalyn on LinkedIn - https://www.linkedin.com/in/kalynsaulsberry/

Vince on LinkedIn - https://www.linkedin.com/in/vince-saulsberry-fong/

Audience Synergy - 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

Sam Rosati and Kaustubh Deo are joined by Andy Harbut and Josh Richman to break down the often-overlooked role of insurance in small business acquisitions. Drawing from decades of experience in private equity and insurance brokerage, Andy and Josh share how they built NewCo Risk through a hybrid of acquisition and startup, and why they chose to focus on the underserved search and ETA community. The conversation dives into real-world examples of how insurance diligence can make or break a deal, along with lessons from their first year as entrepreneurs scaling a niche, service-heavy business.

They discuss:

- How insurance diligence can uncover hidden risks that materially impact deal viability

- Why many small businesses are underinsured or mispriced and how that affects buyers

- The strategy behind building an insurance brokerage through a carveout and acquisition model

- Key operational and technology decisions that shaped NewCo Risk’s early growth

- Why sales capability is critical for operators and searchers running small businesses

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/

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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
(00:02:34) - Introducing Josh and Andy
(00:07:22) - Learnings from the self-funded community
(00:12:15) - How Josh and Andy think about the NewCo Risk business model
(00:15:22) - The decision to start NewCo Risk
(00:24:45) - The state of NewCo in 2026
(00:29:14) - How to run your business for less money
(00:32:16) - Josh and Andy’s roles within the business
(00:39:28) - War stories
(00:51:23) - Getting in touch

In this episode of The Intentional Owner, Kaustubh Deo sits down with Michael Young to explore the realities of building and scaling a people-first accounting firm after a long and uncertain search journey. Michael shares how he transitioned from Big Four accounting into entrepreneurship, ultimately acquiring and growing Bay Business Group while navigating the challenges of hiring, client selection, and operational discipline. The conversation dives into what small business owners should actually expect from bookkeeping, controller, and CFO services, and how financial clarity can drive better decision-making. Along the way, Michael offers an honest look at the emotional and practical challenges of search, and why defining your “why” matters more than anything. They discuss: - The differences between bookkeeping, controller, and CFO support, and what small businesses actually need - Why search is unpredictable and heavily influenced by luck, not just effort - How to scale a people-driven business and the challenges of hiring high-quality talent - The importance of client selection, scope control, and saying no to the wrong fit - How AI is changing accounting and why advisory and judgment still matter Support our Sponsor Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at ⁠https://bay-biz.com/⁠ Have SMB questions for Kaustubh and Sam? Email them to ⁠kd@sunthra.com⁠ and they will answer them on the Pod! 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
(00:01:26) - Introducing Michael Young
(00:04:06) - Dropping search to build a startup
(00:07:49) - Bookkeepers vs controllers
(00:11:35) - When do you need a CFO?
(00:13:03) - Owner finance literacy
(00:14:51) - Scaling a people firm
(00:16:42) - Client fit and boundaries
(00:20:09) - Operational metrics and change
(00:24:07) - Family life and time control
(00:25:22) - Long term vision and short term priorities
(00:28:50) - Ideal client profiles
(00:31:37) - Searchers as clients
(00:34:02) - Churn and scope control
(00:35:41) - Sales versus service
(00:36:34) - AI and accounting
(00:39:01) - Future proofing systems
(00:44:53) - Search journey reflections

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo sit down with Denisse Montenegro to unpack the realities of operating and scaling a business while fully owning the P&L. Denisse shares a candid look at navigating financial visibility, decision-making, and the evolving responsibilities that come with ownership. The conversation explores the tension between delegation and accountability, as well as the importance of building the right support systems across finance and operations. Throughout the episode, Denisse offers an honest perspective on what it actually feels like to be in the operator’s seat, especially when answers are not always clear.

We discuss:

• The responsibility of being both the operator and the ultimate owner of the P&L
• How to think about delegation when everything still feels like your responsibility
• The role of bookkeeping, accounting, and advisory support in growing a business
• Why complementary partnerships across finance and operations create leverage
• The challenge of finding peers who truly understand the financial realities of ownership

Support our Sponsors

Bay Business Group provides managed accounting and finance--think bookkeeping to fractional CFO--for scaling businesses. Learn more at https://bay-biz.com/

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/

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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
(00:02:22) - Introducing Denisse
(00:06:41) - Acquisition story and first year challenges
(00:12:11) - Financial awareness as an owner
(00:17:48) - The P&L owner seat
(00:23:14) - Cash flow vs reported profits
(00:29:55) - Bookkeeping vs real financial insight
(00:35:40) - Surviving the turnaround year
(00:42:12) - Advisory support and peer groups
(00:48:27) - Advisory board idea
(00:55:12) - Discipline in financial review
(01:02:30) - Closing thoughts and advice for new owners

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo break down the real differences between self-funded ETA and independent sponsorship. Drawing from their own experiences, they explore how each path shapes your day-to-day responsibilities, risk profile, compensation structure, and long-term upside. They go beyond surface-level comparisons to unpack capitalization, personal guarantees, M&A strategy, and the often misunderstood economics behind equity splits and carry.

The conversation also addresses a growing misconception: that moving “up market” to avoid an SBA personal guarantee automatically makes the path easier. Sam and Kaustubh explain why larger deals come with rarer air, more sophisticated competition, significantly higher deal costs, and greater dead-deal risk. They provide practical context around governance control, management fees versus salaries, pref/common structures, and why leverage is the hidden engine behind self-funded search economics.

They discuss:

- The Core Differences Between Self-Funded Search And Independent Sponsorship

- Day-To-Day Responsibilities Of An Operator Versus A Board-Level Sponsor

- How Capitalization Structures Shape Risk, Control, And Upside

- Why Dead Deal Risk Is Dramatically Higher In Larger Independent Sponsor Deals

- The Real Economics Of Equity Step-Ups, Carry, And Long-Term Wealth Creation

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/

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

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 (00:01:32) - Super Bowl in Seattle (00:07:41) - ETA models compared (00:12:05) - Day to day roles (00:15:54) - Hold period and equity (00:22:46) - Salary vs management fee (00:25:04) - M&A strategy differences (00:28:29) - Capital stack basics (00:29:33) - Earnouts and leverage (00:30:08) - Personal guarantees explained (00:31:09) - Who fits indie sponsorship (00:33:40) - The deal size no man's land (00:35:24) - SBA vs conventional debt (00:36:20) - SBIC lenders overview (00:39:26) - Dead deal cost risk (00:45:15) - Indie sponsor economics reality (00:45:49) - Search fund equity step up debate (00:49:45) - Owner pay and cash flow (00:52:37) - Lifestyle and age advantage (00:56:11) - Wrap up and sponsor plug

#TheIntentionalOwner #TIO #SMB

Sam Rosati and Kaustubh Deo take a transparent look at how they actually spend their time as entrepreneurs juggling multiple commitments. From running their primary businesses to investing, community building, family life, and personal admin, they break down their weekly hours in real numbers. The conversation evolves into a broader discussion about tradeoffs, intentionality, screen time, and what balance really looks like when you are building businesses and raising families. By the end, they explore what would change if life circumstances shifted and how their “secondary” passions might one day become the main event

They discuss:

• Breaking down primary and secondary business commitments into real weekly hours
• The difference between recurring obligations and one off time commitments
• How live deal cycles can dramatically shift workload and family balance
• The hidden cost of phone usage and screen time in entrepreneurial life
• How to think about adding or removing commitments as life stages change

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/

Have SMB questions for Kaustubh and Sam? Email them to kd@sunthra.com and they will answer them on the Pod!

Topics:

(00:00:00) - Intro (00:00:58) - Discussing personal and professional commitments (00:02:12) - Breaking down work and personal life balance (00:05:24) - Detailed analysis of primary job roles (00:07:10) - Secondary job roles and extracurricular activities (00:13:20) - Time allocation and efficiency strategies (00:23:56) - Peer groups and community involvement (00:31:13) - Calculating weekly hour (00:36:14) - Challenges of business growth (00:40:03) - Time management strategies (00:48:06) - Screen time and productivity (00:56:00) - Future plans and retirement thoughts (00:58:13) - Conclusion and call to action

In this episode of The Intentional Owner, Sam Rosati and Kaustubh Deo sit down with Mike Botkin for a wide-ranging conversation on operator mindset, capital alignment, and what it really takes to build and scale small businesses. Drawing from his experience growing a tiny landscaping company into one of the largest in the Southeast, Mike shares hard-earned lessons on choosing partners, knowing when to stay in the CEO seat, and why not all growth paths are created equal. The discussion blends candid reflections on leadership, stress, and lifestyle tradeoffs with tactical insights on capital structures and service business economics.

They discuss:

• Why underwriting the operator matters as much as underwriting the business
• The realities of giving up the CEO role and when it backfires
• How capital partner incentives shape decisions in both good and bad times
• The differences between residential and commercial services from an operator’s perspective
• When turnarounds and small businesses can outperform larger, more polished deals

Links:

Mike on X - https://x.com/MikeBotkin_

Mike's website - https://botkinhq.com/

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

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

Topics:

(00:00:00) - Intro (00:00:55) - Introducing the guest: Mike Botkin (00:06:23) - Mike's journey in the landscaping business (00:17:35) - Challenges of being a CEO (00:23:26) - Finding the right role: operator vs. advisor (00:36:04) - The value of turnarounds and small business investments (00:37:23) - Navigating business challenges and stress (00:38:03) - Finding your passion in business operations (00:38:42) - The micro business operator's advantage (00:42:15) - Balancing lifestyle and business goals (00:52:59) - Choosing the right capital partner (00:58:33) - Residential vs. commercial services debate (01:10:50) - Launching commercial services: tips and strategies