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 [email protected] 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:

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 [email protected] 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