Exit Algorithms

In this episode, I sit down with John MacInnes, MIT-trained serial entrepreneur, YPO member, and founder of SimAmplify, a platform connecting M&A advisors with qualified buyers that has already facilitated over $3 billion in deal flow in just its first year. John built Print Audit from his basement into a global software company over 20 years before selling it, then sold Payroll Rewards to American Express, and is now on a mission to help founders get the best possible exit through SimAmplify.

This episode is essential for any business owner thinking about selling, scaling, or simply building a more valuable company from day one.

We discuss:
– John's journey from selling his parents' books to secondhand bookstores as a kid, to running a painting franchise in college, to building a 20-year global software company from his basement.
– How Print Audit grew from a one-man basement operation into a global powerhouse by hiring based on values, building a product that created genuine switching costs, and transitioning to recurring revenue.
– The hook strategy: how bundling free software into a SaaS subscription made customers nearly impossible to leave, and why recurring revenue is the single most valuable asset you can build for a future sale.
– The near-death experience that almost killed Print Audit when their biggest customer, Ricoh, acquired a competitor, and how diversifying from one large customer to hundreds of smaller ones saved the company and tripled its value.
– The three biggest mistakes business owners make when preparing to sell: customer concentration above 20%, messy finances that do not match what buyers expect to see, and being the linchpin of the company instead of delegating.
– Why the best time to start preparing for your exit was 5 years ago and the second best time is today, and why everything you do to get ready to sell also makes the business run better anyway.
– How to choose the right advisor based on your revenue size: brokers for main street businesses under $1M, M&A advisors for the $2M to $5M and above range, and investment bankers for large mid-market deals.
– Why you should interview at least 5 advisors, ask for industry-specific references, and watch out for advisors who make more money on upfront fees than on actually closing deals.
– How John uses Claude and AI to automate LinkedIn posting, generate buyer profiles, classify deal industries, and run weekly deal reviews across $2 billion in live transactions on SimAmplify.
– Where AI is going in M&A: why junior analyst roles at investment banks are already being replaced, and what that means for the next generation entering the workforce.

Connect with John and visit www.cimaplify.com.

In this episode, I sit down with Alex Maibaum, founder and CEO of Predictive Supply Chain Solutions, a cloud-based software and consulting firm that helps mid-size businesses forecast smarter, cut excess inventory, and unlock serious cash flow. Alex is a supply chain veteran who has operated inside high-growth, hyper-accelerating businesses and built his platform specifically because the right tool did not exist for the operators who needed it most.

This episode is a must-listen for any product-based business owner who is sitting on too much inventory, struggling with cash flow, or trying to get their sales, operations, and finance teams to actually communicate with each other.

We discuss:
– How Alex worked his way through sales, marketing, and warehouse floors early in his career and discovered that the biggest problem in most businesses is not a people problem, it is a data communication problem.
– The ping pong table analogy: why sales and marketing, operations, and finance are constantly fighting each other instead of rowing in the same direction, and how data visualization fixes it.
– Why inventory turns is the business metric that unlocks cash flow, and how converting inventory into cash faster means more capital to grow.
– The 80-20 rule applied to supply chain: why 90% of most businesses' revenue comes from 10% of their SKUs, and how SKU bloat is silently strangling cash flow.
– A four-step framework any business owner can build today using Shopify, Excel, and a 3PL report: establish a source of truth, consolidate purchasing, understand historical sales, and log future big commitments.
– How to use AI for demand planning and forecasting without creating a black box, why asking the model to write a wiki after every build is a game-changing practice, and how to validate AI outputs without being a data scientist.
– Why the black box problem is the biggest risk in AI-assisted supply chain work, and the practical technique Alex uses to keep every model transparent, auditable, and updatable.
– How to think about minimum order quantities, carrying costs, and opportunity cost when deciding which SKUs to keep, cut, or reorder.
– Real examples of businesses that locked in large retail orders with Walmart or Target without planning for them and suddenly found themselves out of stock for six months.
– Where AI is going in supply chain: why demand planning used to require PhD-level data scientists and now any operator can access the same capability.

Ready to work with Alex? Visit predictivescs.com.

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.

In this episode, I sit down with Chris Carter, founder and CEO of Approyo, a firm specializing in SAP migrations, monitoring, basis support, and application hosting. Chris is also a serial entrepreneur who has started 11 companies, sold multiple, authored 17 books including 4 bestsellers, and is currently building Approyo, Mugatu AI, and Charging Bunny simultaneously while investing in a professional soccer team in Belfast, Ireland.

This episode is a masterclass for any business owner trying to implement technology the right way, hire and build a high-performance culture, and prepare a business for a high-value exit.

We discuss:
– Chris's path from a Commodore VIC-20 at age 14, to Georgia Tech, to a Coca-Cola internship that accidentally launched a 30-plus year career in the SAP ecosystem.
– Why SAP runs 93.7% of financial transactions globally, what the current cloud migration wave means for businesses, and why the US Navy and government run on SAP.
– His three-step framework for implementing any new technology in a business: train first, find the passionate champion, and sell it from the top down.
– Why most companies fail at AI adoption not because of the technology but because of poor thought process, and how to separate the right tools from the noise.
– The hiring mistakes Chris made in his early companies, why he was the bottleneck, and the lesson it took selling multiple businesses to fully learn: hire fast, fire faster.
– Why he now gives new hires 30 days to get up to speed on the tools that matter, and why he actively recruits from the military and fresh graduates who will go all in.
– His framework for running a business as if it were publicly traded, keeping financials, HR, contracts, and documentation fully in order before any exit conversation begins.
– How Chris uses Gemini, Notebook LM, Gamma, and vibe coding tools daily to write books, build apps, prep presentations, and run three companies simultaneously.
– Why AI is not replacing humans but making them bigger, better, faster, and stronger, and why that conversation needs to start in high schools, not boardrooms.
– Where he sees enterprise AI going: less about consumer apps and more about deeply integrated organizational decision-making that uses historical data to shape the future.

Want to connect with Chris? Visit christophermcarter.com

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.

In this episode, I sit down with Ricky Ho, co-founder and CEO of SourceReady, the AI-powered search engine for finding factories and suppliers globally. Ricky dropped out of UC Berkeley at 19, built and sold his first supply chain tech company by 23, raised $22 million, landed on Forbes 30 Under 30, and now leads SourceReady, which is already trusted by Fortune 500 brands just two years in.​​

This episode is packed with tactical insight for any founder building a physical products business, navigating tariffs, or trying to find the right suppliers in a fast-changing global market.​​

We discuss:
– Ricky's path from a manufacturing family background to UC Berkeley dropout, to building and selling his first supply chain software company at 23.
– Why legacy enterprise software had terrible adoption rates and how he built a more collaborative, modern alternative that grew to nearly 100 people.
– What he would do differently the first time: scaling too fast before finding true product-market fit, and why raising too much money too early creates pressure that hurts startups.
– How SourceReady uses customs data, government records, and trade show data to index the world's supply chain and help buyers find vetted, reputable suppliers fast.
– Why Alibaba search results are pay-to-rank, not quality-ranked, and how to use customs data to verify a supplier is actually working with reputable brands.
– How to think about supply chain diversification beyond China, the hidden costs of long lead times, and when sourcing from Mexico or Vietnam makes more financial sense than a cheaper FOB price from Asia.
– Tariff strategy: how changing a product's material composition can shift its HS code classification and legally reduce import tariff exposure.
– Where AI is already doing the work no human team could match: searching millions of global suppliers in seconds against specific criteria.
– Why AI will commoditize the data-heavy, pattern-recognition side of sourcing, but human expertise in relationships, negotiation, and strategy will only become more valuable.
– How Ricky structures his week, his P0 priority system, and why great CEOs make fewer, higher-quality decisions rather than staying perpetually busy.

Ready to find suppliers faster? Visit sourceready.com, completely free to use. Connect with Ricky on LinkedIn at linkedin.com/in/ricky-ho-a25a05104.

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.

In this episode, I sit down with Brian Root, former Amazon and Walmart Labs product executive, US patent holder in e-commerce product classification, and now the founder of two simultaneous ventures: Norris Advisory, where he helps SMB buyers navigate due diligence and acquisitions, and Rooted in Product, his fractional CPO practice helping companies scale through smart technology decisions.

Brian's story is one of the most grounded and practical we have had on the show. After a layoff from big tech, he spent six to nine of the hardest months of his life before finding his footing, building two businesses from a $25 website, and developing a framework for evaluating technology in small businesses that most buyers and operators have never heard of.

We discuss:
– Brian's path from programming games in QuickBasic at age 10 to supply chain, business school, Amazon, Walmart Labs, and eventually being laid off and building two businesses from scratch.
– Why being laid off from what felt like a stable tech career was the shock that forced him to discover what he actually wanted, and how entrepreneurship through acquisition became the answer.
– What "tech enabled" actually means when evaluating a business for acquisition, and why a chatbot on a website is not the same as real technology differentiation.
– How to evaluate whether a business is using AI in a meaningful way or just slapping a label on it, and the signals that tell you the difference during due diligence.
– Why the biggest red flag in a tech-enabled acquisition is not bad software, it is undocumented thought process, and what good structured thinking actually looks like in a business.
– How to identify the two categories where technology genuinely adds value: growth levers that scale reach without proportional cost, and internal process automation that lowers the cost basis of the business.
– Why owner dependence is not just a relationship problem but a systems problem, and how one founder Brian worked with literally coded his own thought process into proprietary software before selling.
– Why AI content and outreach often fails, what Amazon figured out about automation that most companies still get wrong, and why the hidden use of AI almost always outperforms the obvious use.
– How Brian structures his week running two service businesses simultaneously, and why he is building systems now so the business scales disproportionately to his effort later.

Want to connect with Brian? Visit rootedinproduct.com and norisadvisory.com.

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.

In this episode, I sit down with Ricky Ho, co-founder and CEO of SourceReady, the AI-powered search engine for finding factories and suppliers globally. Ricky dropped out of UC Berkeley at 19, built and sold his first supply chain tech company by 23, raised $22 million, landed on Forbes 30 Under 30, and now leads SourceReady, which is already trusted by Fortune 500 brands just two years in.​​

This episode is packed with tactical insight for any founder building a physical products business, navigating tariffs, or trying to find the right suppliers in a fast-changing global market.​​

We discuss:
– Ricky's path from a manufacturing family background to UC Berkeley dropout, to building and selling his first supply chain software company at 23.
– Why legacy enterprise software had terrible adoption rates and how he built a more collaborative, modern alternative that grew to nearly 100 people.
– What he would do differently the first time: scaling too fast before finding true product-market fit, and why raising too much money too early creates pressure that hurts startups.
– How SourceReady uses customs data, government records, and trade show data to index the world's supply chain and help buyers find vetted, reputable suppliers fast.
– Why Alibaba search results are pay-to-rank, not quality-ranked, and how to use customs data to verify a supplier is actually working with reputable brands.
– How to think about supply chain diversification beyond China, the hidden costs of long lead times, and when sourcing from Mexico or Vietnam makes more financial sense than a cheaper FOB price from Asia.
– Tariff strategy: how changing a product's material composition can shift its HS code classification and legally reduce import tariff exposure.
– Where AI is already doing the work no human team could match: searching millions of global suppliers in seconds against specific criteria.
– Why AI will commoditize the data-heavy, pattern-recognition side of sourcing, but human expertise in relationships, negotiation, and strategy will only become more valuable.
– How Ricky structures his week, his P0 priority system, and why great CEOs make fewer, higher-quality decisions rather than staying perpetually busy.

Ready to find suppliers faster? Visit sourceready.com, completely free to use. Connect with Ricky on LinkedIn at linkedin.com/in/ricky-ho-a25a05104.

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.

In this episode, I sit down with Nate Littlewood, founder of Future Ready CFO and host of Profits on Purpose, who helps ecommerce and CPG founders master cash flow, profitability, and fundraising so they can scale with clarity instead of chaos. Nate bootstrapped his own urban gardening brand from a small Kickstarter to seven figures, worked on Wall Street, mentored at a New York accelerator, and now acts as a fractional CFO and “numbers wingman” to purpose-led founders.​​

We discuss:
– Why most ecommerce and CPG businesses die from cash problems, not bad products, and how to use your financials as a strategic ally instead of an afterthought.
– What Nate learned from building Urban Leaf through content, SEO, community, and Amazon as a customer acquisition engine rather than just a marketplace.
– The three metrics he cares about most: lifetime gross profit versus CAC, cash conversion cycle, and current ratio, and what each one actually tells you about the health of your business.
– How to think about debt like an investor, when borrowing is smart, and when high-cost capital quietly kills your margins.
– Why forecasting is always “wrong” but still essential, and how to use projections to see potholes months ahead so you can negotiate better funding or avoid the problem entirely.
– How Nate is starting to use AI for marketing, analysis, and his “hidden profit audit,” and why financial model-building in spreadsheets is likely to be automated away in the next few years.
– His one practical tip for founders: track your time for a month, then feed it into AI and let it diagnose how you are really running your business.

If you are an ecommerce or CPG founder trying to stop flying blind with your numbers, plug cash leaks, and make smarter decisions about inventory, marketing spend, and financing, this episode will shift how you think about your role and your metrics.​

Want to connect with Nate? Visit futurereadycfo.com and find him on LinkedIn by searching “Nate Littlewood Future Ready CFO.”​

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.​

0:00 Intro to Exit Algorithms and Nate Littlewood
1:01 Nate’s background: Wall Street, Urban Leaf, and Future Ready CFO
2:15 Why most startups fail because of money, not ideas
3:30 What Urban Leaf sold and how it grew with content, SEO, and community
5:30 Using Amazon as a customer acquisition engine, not the whole business
7:21 What Nate would do differently and why he would not start the same brand again
9:20 Realizing he is more valuable as a founder’s CFO “wingman”
10:31 The top three metrics: lifetime gross profit vs CAC, cash conversion cycle, current ratio
13:50 Cash conversion cycle and working capital in physical product businesses
15:10 How forecasting actually works and why it is about spotting potholes early
17:43 How to think about debt, ROI, and risk as a founder
20:15 Choosing funding based on returns and risk, not just interest rate
22:20 Tools, spreadsheets, and where Nate expects AI to replace financial modeling
24:10 The “hidden profit audit” and finding leaks in ecommerce P&L
25:49 Where AI is going for ecommerce operators and finance
29:54 Why product and customer experience will matter more as AI commoditizes acquisition
30:48 One practical tip: track your time for a month and have AI diagnose it
32:13 Where to find Nate online and learn more about Future Ready CFO

In this episode, I sit down with Ken Himmler, personal wealth strategist with over 40 years of experience, author of multiple books including the upcoming One Wealth Map, former host of Money Talks radio, and founder of a family office practice serving business owners from $2M to $25M in net worth.

Ken breaks down exactly why most business owners leave millions on the table when they sell, why waiting until the last minute to plan an exit costs you 40% or more of your valuation, and how an integrated financial strategy, combining tax planning, M&A structure, and personal wealth, changes the entire outcome of a sale.​

We discuss:
– Ken's path from one of the first financial planning firms in the country in the early 80s, through launching his own firm, to building a family office model that serves the $2M to $25M business owner.​
– Why the fragmented CPA, lawyer, and financial advisor model is one of the most expensive problems a business owner can have, and why no one is connecting the pieces.
– Why three years is the minimum runway to prepare for a high-value exit, how to eliminate key person risk, and why most owners find out too late how much they could have gotten.​
– How to maximize EBITDA before a sale by fixing the inefficiencies a private equity buyer is already planning to profit from.​
– Why good tax planning makes your returns look less profitable, why that is actually correct strategy, and how to use a P&L recast to show buyers the real picture.
– The danger of tying all your net worth to one business, why asymmetric risk destroys founders, and where to invest excess capital at different stages.​

Want to connect with Ken? Find him on YouTube at @OneWealthMap where he shares in-depth content on tax strategy, business valuation, and retirement planning.

Ready to grow and plan your exit? Visit www.BizExitGrow.com where thoughtful systems and strategies help build lasting value and legacy.​

Chapters:
0:00 Introduction to Ken Himmler and One Wealth Map
1:29 Ken's background: from the first financial planning firms to 40 years of wealth strategy
3:29 Why the fragmented CPA, lawyer, and advisor model fails business owners
3:50 How integrated financial planning unlocks earlier and larger exits
4:56 The cost of waiting: why selling without a three-year runway loses you 40%
6:14 The three-year exit roadmap: leadership, org chart, and deal search
7:03 What actually increases business valuation beyond owner dependence
8:15 Why most business owners have all their net worth tied up in one asset
9:34 Shiny object syndrome and the case for focusing on one business to sell
10:15 Where and how to invest personal capital outside the business
12:18 Can you ever truly coordinate your CPA, lawyer, and advisor?
13:37 The family office model: same experience without needing $25 million
14:42 Upgrading your financial coaching as your business grows
14:56 Tax strategy for business owners: P&L recast and books and records
17:21 What a buyer is actually buying and how to show them the real cash flow
18:31 How Ken's firm is building custom AI tools for tax and investment analysis
20:29 Real-time beta testing and building faster than legacy fintech
21:13 Where AI is going: 90% of grunt labor replaced and AI avatar interviews
22:18 One Wealth Map: Ken's new book on pairing humans and AI for better decisions
24:04 Ken's One Life Map app and structuring days for maximum output per hour
25:29 The 4:30am gym routine with a laptop and why focus beats multitasking
27:09 One practical tip for business owners: plan, plan, plan
27:33 Where to find Ken online

In this episode, I sit down with Charlie Safro, founder and CEO of CS Recruiting, to break down what it really takes to build a people-first recruiting firm, scale through uncertainty, retain top talent, and navigate an exit without losing the culture that made the business work in the first place.​

Charlie bootstrapped CS Recruiting from an accidental start into a leading supply chain recruiting firm, helped grow a transportation technology company to 110 employees before its sale, and recently sold her own company after 15 years of building it. We also get into why recruiting should focus on retention, how hybrid work became part of her culture long before it was mainstream, and why AI is creating as much noise in recruiting as it is efficiency.​

We discuss:​
– How Charlie went from marketing into recruiting, helped scale her husband's transportation technology company, and turned a side stream of referrals into CS Recruiting.​
– The early leap-of-faith moment that forced her to hire her first employee and build capacity before she fully knew how she would deliver.​
– Why scaling a service business is a constant balancing act between market demand, team capacity, and responsible hiring.​
– How a personal childcare need helped shape a hybrid work culture years before remote work became standard.​
– What finally pushed her to consider selling after years of saying she had no exit strategy, and how burnout and client demand both played a role.​
– Why the right buyer was not just about price, but about preserving her team, client relationships, and the integrity of the brand.​
– The biggest hiring mistake business owners make: hiring a warm body instead of recruiting to retain.​
– Why retention comes down to simple human behavior like trust, recognition, and actually knowing your employees beyond their job title.​
– Her candid take on AI in recruiting, where it helps with speed and admin work, and where it creates noise, fake applications, and more work for humans.​

If you are a founder, operator, or supply chain leader trying to hire better, retain longer, and build a business that is both scalable and sellable, this episode is packed with practical insight.​

Want to learn more about Charlie's work? Follow Charlie Safro and CS Recruiting on LinkedIn (https://www.linkedin.com/in/charliesaffro/), where she regularly shares advice on hiring, retention, job search strategy, and leadership.

Ready to grow and plan your exit? Visit www.BizExitGrow.com where thoughtful systems and strategies help build lasting value and legacy.

Chapters:​
0:00 Introduction to Charlie Safro and CS Recruiting​
0:55 Charlie's background in marketing, transportation tech, and recruiting​
3:05 Building CS Recruiting from an accidental start​
4:00 The early leap that forced her to scale​
6:24 Hiring, layoffs, and the balance of scaling responsibly​
9:25 How hybrid work became part of the company culture early​
12:50 Thinking about an exit after years without a plan​
15:33 Burnout, timing, and putting the idea of a sale into the universe​
16:28 Why HireWell was the right fit​
19:44 What she would do differently before diligence​
21:31 Common hiring mistakes business owners make​
23:24 Talent retention and treating employees like humans​
25:50 AI in recruiting: efficiency vs noise​
30:36 Tools, prompts, and where AI actually helps​
33:07 One practical tip for business owners​
35:02 Where to find Charlie online

Lexson Mathieu is the co-founder of Odase Investment Consortium, a holding company that acquires and scales operating businesses across fragmented industries. Before stepping into M&A, Lexson was an undefeated professional boxer and IBF champion who walked away from his belt during COVID, cashed out of crypto at the top of the market, and used that discipline to make 10,000 cold calls before closing his first acquisition, a $5.4 million trucking company with little to no capital down.​

We discuss:

– Lexson's journey from professional boxing and international gold medals to crypto exits and business acquisitions, and why resilience was the common thread throughout.​

– How he built Odase Investment Consortium by giving equity to lawyers, accountants, and industry experts he had never met in person, and why that unconventional bet paid off.​

– The 10,000 cold calls it took to land his first deal, why motivated sellers are the only sellers worth pursuing, and how to identify them fast.​

– How Lexson acquired his first $5.4M trucking company with little to no capital and saved over $100,000 in the first two months by renegotiating fuel, insurance, and maintenance contracts.​

– Why bigger deals are actually easier than small ones, why the drama is the same at $100 and $6 million, and how his roll-up strategy works across trucking and moving companies.​

– His approach to building accountable management teams, why he keeps no more than five direct reports, and why he describes himself as Nick Fury, not Iron Man.​

Want to connect with Lexson? Find him on Instagram (@Lexson Mathieu) and send him a direct message.​

Ready to grow and plan your exit? Visit www.BizExitGrow.com where thoughtful systems and strategies help build lasting value and legacy.​

Timestamps:

0:00 Introduction: Exit Algorithms with Lexson Mathieu

1:00 Why Lexson Lists Himself as Chief Business Development Officer, Not CEO

1:45 Boxing Background: From Amateur Gold Medals to IBF Undefeated Pro

3:00 Walking Away From the Belt: How COVID Changed Everything

3:30 Moving to Mexico, Going All In on Crypto, and Exiting at the Top

4:30 Founding Odase Investment Consortium and Giving Equity to Strangers

5:30 Following the Dan Peña Model: Your First 100 Million

6:00 18 Months and 10,000 Cold Calls to Close the First Deal

7:00 First Acquisition: $5.4M Trucking Company with No Money Down

8:30 How Boxing Built the Resilience to Take Rejection in Business

10:30 What Makes a Business Attractive Beyond EBITDA: The Motivated Seller

12:30 How a Seller Can Prepare for a Successful Exit and Be Part of the Solution

15:00 Line of Credit as a Business Asset: Why Sellers Should Build It Now

16:30 Asset-Heavy vs. Asset-Light: Lexson's Preference in Trucking

17:30 Saving $100K in the First Two Months Post-Acquisition

20:00 Stretching Payables and Building Working Capital as a New Owner

21:30 Growth Through Acquisition: How Lexson Closed Deal Two Just Four Months Later

23:00 Why Bigger Deals Are Simpler Than Small Ones

25:00 Integrating a Trucking and Moving Company: Synergies and Challenges

27:30 Building Accountable Management Teams: The Nick Fury Model

29:00 Hiring Mistakes, Firing Fast, and Screening for Red Flags

31:00 Using Industry Experts for Equity to Secure Financing

33:00 A Contrarian Take on AI: Where Lexson Draws the Line

35:00 Technology That Has Transformed His Moving Company Operations

38:00 KPIs That Actually Matter: Why Lexson Focuses on the Top Line and Deal Flow

41:00 Playing to Your Strengths: Why He Does M&A, Not Trucking Sales

43:00 Practical Tip: The Weekly Self-Accountability Report