Watch: https://youtu.be/I8AUgv479HA

About the Guest: 
Jed Morris Jed Morris is the Managing Partner of Sunset Coast Partners, an independent sponsor firm focused on acquiring defense contractors. A former Air Force veteran and Microsoft engineer, Jed’s journey into entrepreneurship was marked by soaring ambition — and a brutal, humbling failure that left him facing nearly $1 million in personally guaranteed debt. Rather than hiding, Jed leaned in, building a growing community of fellow acquisition entrepreneurs committed to telling the full truth about the real risks behind buying businesses. He now actively shares his hard-won lessons through his writing, speaking engagements, and his "Start Searching Challenge" program for first-time buyers.

Summary:
In this raw and revealing conversation, Ron Skelton sits down with Jed Morris, Managing Partner of Sunset Coast Partners, to unpack the brutally honest realities of buying small businesses. A fellow veteran and self-funded searcher turned investor, Jed shares his journey from military service to big tech — and then into the world of business acquisitions, including his painful first-hand experience with failure, personal guarantees, and crushing debt. This isn't a feel-good "buy a business with no money down" fantasy — it's a boots-on-the-ground look at the risks, the egos, the missteps, and the hidden hazards first-time buyers need to face if they want a real shot at success. Far from doom and gloom, the episode offers sharp wisdom for new buyers: how to approach culture shock, why the "passive ownership" myth is dangerous, and the reality that buying a business means buying people first. It's a masterclass in what can go wrong — and what it actually takes to do it right.

Key Takeaways:

1. Buying businesses is buying culture, not just cash flow.
   Success hinges more on managing people and adapting to inherited cultures than on financial spreadsheets.
2. "No money down" deals are real — but extremely rare and dangerously hyped.
   Buyers pursuing these unicorns must be ready for much higher risk profiles and massive deal flow effort.
3. First-time buyers drastically underestimate change management.
   Rolling into a 30-year-old business and expecting quick improvements without cultural buy-in is a recipe for revolt.
4. Early relationships with PE firms and investment bankers are critical.
   If you're planning to flip a business to private equity later, you better design the acquisition and growth with their preferences from day one.
5. In distress, culture collapses faster than cash flow.
   When things go wrong, the hidden dynamics — loyalty, trust, morale — become your battlefield, not just your P&L.
6. Defense contracting offers real opportunity, but brings unique barriers.
   Issues like security clearances, government contract classifications, and niche buyer pools make it a specialized but lucrative target market.
7. Surviving business ownership demands humility, patience, and real respect for frontline workers.
   Ivy League degrees and fancy vests won't save you from getting "eaten alive" if you can't relate to your workforce.
8. Building for an exit must start before you buy.
   If you don't know what a future buyer needs — team, systems, margins — you're not "building to sell," you're just surviving.

--------------------------------------------------
Contact Jed on
Linkedin: https://www.linkedin.com/in/jedmorris/
Website: https://jedbmorris.com/
--------------------------------------------------
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▶️Previous Episode: E277: Most Marketing Teams Get Axed After a Sale - Here's How to Make Yours Unkillable - https://youtu.be/BbypHaRpOtA

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

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About the Guest: 
Victoria Hajjar is the founder of Ugli Ventures and a marketing strategist with deep experience building brands from the inside out. With a background that spans A&E, real estate development in China, and leading marketing departments for high-growth companies, Victoria has learned to build marketing engines that are scalable, measurable, and ready for acquisition. Her superpower? Turning messy marketing into a growth asset—fast.

Summary:
In this episode of How2Exit, host Ron Skelton sits down with Victoria Hajjar, founder and CEO of Ugli Ventures, for an energetic, no-fluff conversation about what it really takes to build a marketing machine that adds value in an M&A context. Instead of chasing vanity metrics or relying on branding for branding’s sake, Hajjar breaks down the systems, scorecards, and human factors that make marketing a driver—not a passenger—of enterprise value. Whether you're a seller prepping for exit or a buyer looking to avoid post-acquisition marketing disasters, this is required listening. Victoria doesn’t just theorize—she’s been on the acquisition side and knows firsthand what it looks like to inherit a marketing mess… or a marketing moat.

Key Takeaways:

1. Marketing departments often feel the most vulnerable in acquisitions because buyers usually already have their own team. But dismissing the seller's marketing team too quickly risks losing the local expertise and systems that are driving current revenue.
2. Buyers should pause before overhauling anything—Victoria recommends a 60-90 day observation window before making marketing changes post-acquisition.
3. Most sellers don’t have a documented, measurable marketing system, and this lack of structure reduces perceived business value.
4. Brand value isn’t just logos or followers—it’s trust, relationships, and conversion rates. You need to prove that your audience responds to your messaging with measurable action.
5. Having one “rainmaker” on the marketing team is risky. Buyers want marketing systems that are transferable and not tied to individual talent.
6. Scorecards, SOPs, and a full-funnel strategy (not just top-of-funnel lead gen) are what differentiate valuable marketing machines from chaotic ones.
7. AI can’t replace human accountability. You can use AI tools for implementation and analysis, but you still need a human to own the marketing outcomes and make judgment calls.
8. Hyper-personalization is the future of marketing. With AI, customers will expect messages tailored to their unique context. Businesses need to prepare for that now—or get left behind.

--------------------------------------------------
Contact Victoria on
Linkedin: https://www.linkedin.com/in/victoria-hajjar/
Website: http://www.ugliventures.com/
--------------------------------------------------
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▶️Previous Episode: E276: She Built a 7-Figure Practice in 2.5 Days a Week—Then Taught Everyone Else How to Exit - https://youtu.be/v4cOn6Py_-Q

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

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About the Guest: 
Dr. Ruth Mannschreck is no ordinary advisor—she’s a former dentist who redesigned her practice around her family’s needs, scaling it with systems, hiring, and delegation. After helping fellow professionals do the same, she now coaches small business owners on how to make their companies scalable and sellable. Her advisory work blends operational excellence with human psychology, emphasizing leadership, culture, and communication.

Summary:
In this episode of the How2Exit Podcast, Ron sits down with Dr. Ruth Mannschreck—a former dentist turned business advisor—to unpack what it really takes to create a business that’s both enjoyable to own and easy to sell. With decades of experience under her belt and a personal story that led to a complete transformation in how she approached business, Ruth lays out a playbook for designing companies that are “self-propelled,” scalable, and ultimately sellable.

From building systems and replacing yourself, to cultivating culture and leadership that retains employees and attracts buyers, Ruth’s approach is deeply human and refreshingly practical. This is a must-listen for any service-based business owner (from dentists to drywallers) who dreams of exiting on their terms—without the chaos.

Key Takeaways:

1. Necessity breeds systems: Ruth transformed her dental practice into a two-and-a-half-day workweek business after a family crisis, focusing solely on systems, delegation, and efficiency—while growing revenue.
2. Self-propelled businesses sell better: The key to a scalable, sellable business is removing the owner from day-to-day operations. A business should run like an orchestra, with the owner as conductor—not a one-person band.
3. The “client journey” is everything: Ruth advises mapping the client experience from the very first call to ongoing follow-up, with clear expectations and responsibilities for each step.
4. Surround yourself with champions (not just experts): You don’t need a CMO—you might need a tech-savvy teenager who’s a social media champion. Ruth emphasizes creative, affordable talent that fits your needs.
5. Culture beats compensation: Employees stay where they feel seen, supported, and developed. Leadership is about painting a compelling vision and nurturing people’s personal and professional growth.
6. Communication style matters: Teams should be trained to adapt their communication to different customers—some want stories, others want the facts. Meeting people where they are improves loyalty and conversions.
7. Organizational clarity is non-negotiable: Ruth’s “A-B-C” test helps identify which tasks employees love, tolerate, or despise. This insight can guide hiring, delegation, and even retention strategies.
8. Owner dependency kills deals: A company that relies too heavily on the founder for sales or operations becomes nearly impossible to sell without a significant discount or risk premium.

--------------------------------------------------
Contact Ruth on
Linkedin: https://www.linkedin.com/in/ruthmannschreck/
Website:  self-propelledbiz.com
--------------------------------------------------
💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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▶️Previous Episode: E275: How AI is Changing Small Business Forever – Jonathan Mast on Scaling After the Acquisition - https://youtu.be/Q2QTYAN7Juo

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

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Watch Here: https://youtu.be/Q2QTYAN7Juo

About the Guest: 
Jonathan Mast isn’t your typical AI guru. At 55, with a Gandalf-like beard and 20 years in digital marketing, he’s positioned himself as the “voice of reason” in a landscape full of overhype and under-delivery. His company, White Beard Strategies, teaches business owners how to use AI without losing their minds—or their margins. Mast’s approach blends deep industry experience with a no-nonsense communication style. He’s not selling pipe dreams; he’s offering a toolkit.

Summary:
In this refreshingly candid episode of the How2Exit Podcast, Ron Skelton flips the usual script. Instead of diving into how to buy or sell companies, he sits down with Jonathan Mast—founder of White Beard Strategies and self-declared AI pragmatist—to tackle a more pressing question: Now that you've bought a business, how do you scale it with AI? With a long white beard and a sharper edge on reality than most AI evangelists or fearmongers, Mast offers a grounded, practical view of how artificial intelligence is changing the game for business owners. From cutting costs without cutting quality, to using AI as a "force multiplier" for human creativity, the conversation strips away the hype and lays down a roadmap that business buyers and owners can actually use.

Key Takeaways:

1. AI is an “Easier Button,” Not an Easy Button: Mast cautions that AI won’t magically solve all your problems—but it will streamline, accelerate, and amplify your existing business processes if used right.
2. Prompt Engineering is Just Delegation 2.0: The most effective prompts treat AI like a new hire—tell it what role it’s playing, what task you need, what the output should look like, and give it context. Then ask, “Do you have any questions?”
3. AI Won’t Replace Humans—But Humans Who Use AI Will Replace Those Who Don’t: The real risk isn’t AI taking your job—it’s your competitor using AI better than you and outpacing your entire operation.
4. Agents Are the Next Frontier: Current tools still need your input, but AI agents—autonomous task-doers with goals instead of prompts—are coming. These could revolutionize business ops by handling repetitive, logic-based tasks with little oversight.
5. AI Is a Skill Multiplier: A mediocre copywriter becomes competent with AI. A great copywriter becomes world-class. AI doesn’t level the playing field—it widens the gap between skilled and unskilled.
6. Bias Is Inevitable—Just Like in Humans: Every AI model reflects the biases of its creators. That doesn’t invalidate its usefulness, but it does mean you need to be vigilant about aligning its output with your brand’s tone and truth.
7. Business Intelligence on Steroids: Jonathan envisions a near future where agents will analyze data from every platform—Google Analytics, YouTube, LinkedIn—and proactively suggest growth strategies without human prompting.
8. Start Small, Start Now: You don’t need to be an engineer or visionary to benefit. Begin with basic tasks like drafting emails, summarizing reports, or analyzing transactions—and build from there.

--------------------------------------------------
Contact Jonathan on
Linkedin: https://www.linkedin.com/in/jonathanjmast/
Website: http://whitebeardstrategies.com/
--------------------------------------------------
💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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🎬SUGGESTED VIDEOS
Don't forget to watch 📽 Our other videos. Please check them out : 

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

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Watch here: https://youtu.be/L90nZyyR1qs

About the Guest: 
Ashish Gupta is the founder of Scale Up Exec, a firm specializing in fractional COO services for growing businesses. With a background in tech startups, corporate leadership at Apple, and turnaround management in the e-commerce space, Gupta has a proven track record of scaling companies and preparing them for exits. His approach blends operational efficiency, strategic growth, and leadership coaching to help founders achieve their business goals.

Summary:
In this episode of the How2Exit Podcast, host Ronald Skelton sits down with Ashish Gupta, founder of Scale Up Exec, a fractional COO firm that helps small and mid-sized businesses scale, streamline operations, and prepare for exits. Gupta’s experience spans from founding a wireless startup acquired by Qualcomm to managing billion-dollar budgets at Apple, to turning around distressed e-commerce businesses and advising companies on high-impact growth strategies. The conversation dives deep into the role of a COO, how founders can recognize when they need operational support, and what it takes to transition from a hands-on entrepreneur to an owner ready for an exit.

This episode is a must-listen for business owners struggling with growth plateaus, operational inefficiencies, or founder burnout. Gupta provides an eye-opening perspective on how businesses should think about leadership transitions, succession planning, and the strategic use of fractional executives to achieve scalable success.

Key Takeaways:

1. The Invisible COO Role in Small Businesses – Even if a company doesn’t have a formal COO, someone is always filling the operational leadership role, whether it’s the founder or an informal manager.
2. Why Founders Get Stuck – Most entrepreneurs are either visionaries or execution-focused, but rarely both. Without a strong operations leader, founders can get caught in a cycle of inefficiency, distraction, and burnout.
3. Recognizing Exit Readiness – Not all business exits are the same. Some founders just want to step back from day-to-day operations, while others need a full buyout. Knowing the difference is crucial for structuring the right transition.
4. Strategic vs. Financial Buyers – A company’s value depends on who the buyer is. Strategic buyers may care more about market share or IP, while private equity and individual buyers are EBITDA-focused. The key is optimizing the right metrics.
5. Boredom is a Business Killer – Many founders unconsciously sabotage their businesses because they get bored after a few years. This often leads to side projects, disengagement, or operational neglect.
6. Fractional COOs as a Scalable Solution – Many companies under $10 million in revenue can’t justify a full-time COO, but a fractional executive can provide high-level leadership and operational improvements without the full-time cost.
7. The Power of Small Changes – Business turnarounds don’t always require sweeping changes. Gupta advocates for a step-by-step approach to transition founders out of operations, proving that small wins build trust and momentum.
8. AI’s Emerging Role in Operations – While AI is improving efficiency in operational management, it still lacks the human touch necessary to navigate company culture, team motivation, and complex decision-making.

--------------------------------------------------
Contact Ashish on
Linkedin: https://www.linkedin.com/in/ashish-gup/
Website: https://scaleupexec.com/
--------------------------------------------------
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▶️Previous Episode: E273: Are You Making This Mistake? – Why 80% of Small Businesses NEVER Sell - https://youtu.be/2Q11T0Dnvu4

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0 

#How2Exit # # 💖Thanks for watching! 💖

Become a supporter of this podcast: https://www.spreaker.com/podcast/how2exit-buy-don-t-build-m-a-of-small-businesses--4859429/support.

Watch Here: https://youtu.be/2Q11T0Dnvu4

About the Guest: 
Mike Finger is the founder of Exit Oasis, a platform dedicated to helping small business owners prepare for successful exits. A former business owner himself, he learned the hard way that not every business is sellable. After a wake-up call from brokers who told him his company wasn’t worth buying, he spent years transforming it into a sellable asset. Today, he coaches owners on how to create businesses that are both profitable and sellable, whether they want to exit or simply work less.

Summary:
Most small business owners believe they’ll sell their business whenever they’re ready. The harsh reality? Most businesses don’t sell. In this eye-opening episode, Mike Finger, founder of Exit Oasis, sits down with Ron Skelton to expose the myths around small business exits. With personal experience transitioning from burned-out owner to successful seller, Mike breaks down the three fundamental questions every owner must answer to create a sellable business. This conversation is a wake-up call for entrepreneurs who assume their business is ready for sale—when in reality, it may not be sellable at all.

Key Takeaways:

1. Most businesses never sell – The industry loves success stories, but the real numbers show that most owners fail to transition their businesses.
2. Sellability starts long before you decide to sell – Owners should focus on making their businesses ownable first. If you can step away without the business collapsing, it’s far more attractive to buyers.
3. Three critical questions determine sellability – Does your business generate desirable results? Can a buyer duplicate those results? Can you document those results?
4. Tax strategies can sabotage sellability – Owners who “minimize” profits for tax purposes are also minimizing the value buyers see in their business.
5. Buyers want proof, not promises – Handshake deals and back-of-the-napkin accounting don’t inspire confidence. If it’s not on your tax return, it doesn’t exist to a buyer.
6. Cash-heavy businesses raise red flags – Many owners say, “a lot of cash walks in the door.” Buyers hear: “I don’t report my real income.” If you want top dollar, run a clean operation.
7. You can’t replace decades of knowledge overnight – Many buyers overestimate their ability to replace an owner who has spent years mastering their business. Experience matters.
8. Start preparing now, not when you’re burned out – Most owners wait too long to think about an exit, and by the time they’re desperate to sell, they’ve already devalued their business.

--------------------------------------------------
Contact Mike on
Linkedin: https://www.linkedin.com/in/mike-finger/
Website: https://exitoasis.com/
--------------------------------------------------
💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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▶️Previous Episode: E272: How to Buy a Business with Almost No Money: SBA Loan Strategies & Franchise Goldmines - https://youtu.be/d01ccqcb1lY

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

Become a supporter of this podcast: https://www.spreaker.com/podcast/how2exit-buy-don-t-build-m-a-of-small-businesses--4859429/support.

Watch Here: https://youtu.be/nvOnJ02n8KA

About the Guest: 
Beau Eckstein is a business coach and expert in SBA lending, business acquisitions, and franchising. With a background in real estate and finance, he now specializes in helping aspiring entrepreneurs secure funding and find the right business or franchise to acquire. His experience includes flipping houses, securing SBA loans for clients, and even starring in an HGTV house-flipping show. His latest project is his book Paycheck to Freedom, co-authored with Tom Wheelwright, aimed at guiding people from employment to business ownership.

Summary:
This episode of How2Exit features Beau Eckstein, a business coach with deep expertise in SBA lending, real estate, and business acquisitions. His journey from struggling student to real estate investor, then into SBA lending and franchise brokering, highlights the resilience and adaptability needed for success in business. The conversation dives into financing strategies, franchise opportunities, and the critical role of business ownership in wealth creation, with Eckstein sharing valuable insights on how entrepreneurs can leverage SBA loans and other funding methods to achieve financial freedom.

Key Takeaways:

1. From Failure to Success – Eckstein’s early struggles in real estate and financial collapse in 2008 forced him to reinvent himself, leading to his expertise in SBA financing and business ownership.
2. SBA Lending as a Wealth-Building Tool – SBA loans, especially the 7(a) and 504 programs, provide pathways for entrepreneurs to finance businesses with as little as 10% down.
3. Franchise vs. Independent Business – While some prefer acquiring independent businesses, franchises offer proven systems and structured support that can accelerate success.
4. The Myth of Passive Income in Real Estate – Owning rental properties isn’t always the cash flow generator people assume; business ownership often yields more predictable profits.
5. Recurring Revenue Models Win – Businesses like pest control, restoration, and commercial painting franchises generate recurring revenue, making them attractive investment choices.
6. Private Equity in Franchising – PE-backed franchises can be a red flag for some buyers, as corporate strategies may prioritize investor returns over franchisee success.
7. SBA Loan Collateral Requirements Can Be Tricky – Borrowers with significant real estate holdings may find SBA lenders requiring liens on personal assets, making alternative financing strategies worth exploring.
8. Eckstein’s Mission: 100,000 Business Owners – His goal is to help aspiring entrepreneurs transition from employees to business owners through education, financing, and franchise opportunities.

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Contact Beau on
Linkedin: https://www.linkedin.com/in/beaueckstein/
Website: https://businessownershipcoach.com/
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💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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▶️Previous Episode: E271: How This Dealmaker Closes a Business Acquisition Every Week—WITHOUT Using His Own Money! - https://youtu.be/31r3dCWdUtA

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

Become a supporter of this podcast: https://www.spreaker.com/podcast/how2exit-buy-don-t-build-m-a-of-small-businesses--4859429/support.

Watch Here: https://youtu.be/31r3dCWdUtA

About the Guest: 
Rob Richmond is a dealmaker, strategic advisor, and founder of Synergy Groups. With decades of experience in technology, business acquisitions, and rollups, Richmond has developed a reputation for structuring creative and sustainable deals. His ability to optimize businesses before acquisition, leverage vendor financing, and create high-value group exits has positioned him as a thought leader in the space.

Summary:
In this episode of the How2Exit podcast, host Ronald Skelton sits down with Rob Richmond, a seasoned dealmaker and founder of Synergy Groups. Richmond shares his experience in mergers and acquisitions (M&A), detailing his innovative strategies for structuring deals, including vendor financing, virtual rollups, and work-in-buyout (WIBO) models. With a track record of completing a deal nearly every week, Richmond offers valuable insights into how business buyers can creatively structure acquisitions, avoid common pitfalls, and maximize value. The conversation also delves into the psychology of sellers, the importance of profiling employees, and how to build scalable business groups.

Key Takeaways:

1. Vendor Financing as a Deal-Making Tool – Richmond explains how structuring deals with seller financing, instead of traditional bank loans, helps align interests and often results in better terms for both buyers and sellers.
2. Work-in-Buyout (WIBO) Strategy – He outlines how entering a business as an advisor or operator before a formal acquisition can lead to stronger deals, minimizing risk and increasing value for all parties.
3. The Power of Virtual Rollups – Richmond discusses his success with virtual rollups, where companies in similar industries collaborate, scale, and eventually exit together for higher valuations.
4. The Importance of Value Creation – Instead of simply acquiring businesses, Richmond emphasizes improving them through strategic changes, sales optimization, and operational efficiency.
5. Overcoming Seller Expectations – Many business owners overvalue their companies. Richmond’s strategy is to shift the conversation from an unrealistic sales price to the actual post-sale cash in the seller’s bank account.
6. Employee Profiling for Growth – By analyzing staff skill sets, businesses can reposition employees for better performance without the need for external hiring.
7. The Right Business Mindset Matters – Smaller business owners often struggle with valuations, unrealistic goodwill expectations, and an inability to scale, while those with $10M+ in revenue tend to be more pragmatic and open to creative deal structures.
8. The Fastest Way to Exit? Management Buyouts. – Richmond highlights management buyouts (MBOs) as one of the quickest and most effective ways for business owners to transition out while ensuring business continuity.

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Contact Rob on
Linkedin: https://www.linkedin.com/in/rob-richmond/
Website: https://morewaysgroup.com/
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💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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▶️Previous Episode: E270: From Landscaping Hustle to Tech Empire: Bryan Clayton’s $90M GreenPal Revolution - https://youtu.be/e3HHrrIc4Hc

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

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Watch Here: https://youtu.be/e3HHrrIc4Hc

About the Guest: 
Bryan Clayton is the CEO and co-founder of GreenPal, a tech platform connecting homeowners with lawn care professionals. Before launching GreenPal, Clayton built and sold a successful landscaping business with over 150 employees. He’s an advocate for using technology to modernize service-based businesses and believes AI will dramatically reshape industries in the coming years.

Summary:
In this episode of How2Exit, host Ronald Skelton sits down with Bryan Clayton, CEO and co-founder of GreenPal, a platform often dubbed the "Uber for lawn care." Clayton shares his entrepreneurial journey, from a childhood forced into mowing lawns by his military father to scaling and selling a multimillion-dollar landscaping company. He discusses the challenges of selling a business, the emotional void that follows an exit, and how he transitioned into the tech space to launch GreenPal. The conversation dives deep into automation, AI’s impact on business, and how small service-based companies can leverage technology to scale efficiently.

Key Takeaways:
Forced Entrepreneurship Sparks Innovation: Clayton’s first business began out of necessity when his father made him mow lawns as a teenager. That small hustle turned into a multimillion-dollar landscaping business.

Scaling a Service Business is a Systematic Process: Building a large-scale landscaping company required Clayton to develop efficient processes, training programs, and a system for hiring and retaining workers.

Selling a Business Takes Preparation: It took Clayton two years—one to structure the business properly and another to find a buyer—to successfully sell his landscaping company.

The Emotional Impact of an Exit is Real: Clayton struggled with an identity crisis after selling his business, which eventually pushed him to start GreenPal.

AI and Automation Are Changing Business Operations: The discussion explores how AI is reshaping everything from customer acquisition to software development, making it easier to run lean and profitable companies.

Technology is Now Essential for Service Businesses: Small business owners who fail to adopt tech tools are operating as if it’s still the 1990s, missing opportunities to increase efficiency and profitability.

GreenPal Provides a Business-in-a-Box for Lawn Care Providers: The platform handles customer acquisition, scheduling, invoicing, and even upselling additional services for lawn care professionals.

Future-Proofing Means Staying Tech-Savvy: Clayton warns that service providers who resist technology will fall behind as AI and automation continue to accelerate business capabilities.
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Contact Bryan on
Linkedin: https://www.linkedin.com/in/bryan-clayton-a96b33214/
Website: https://www.yourgreenpal.com/
--------------------------------------------------
💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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▶️Previous Episode: E269: How to Sell Your Business for Top Dollar – Secrets from an Acquisition Expert - https://youtu.be/XLZjRoLivJw

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

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Watch Here: https://youtu.be/XLZjRoLivJw

About the Guest:
Dolores Hirschmann is the founder of Masters in Clarity, a business strategist, speaker coach, and acquisition entrepreneur. With a background in marketing and communication, she helps business owners clarify their message to scale and exit successfully. She previously ran one of the largest TEDx events on the East Coast and co-founded a company that she later sold to Grant Cardone. As an active buyer of small professional services businesses, she works with founders to structure successful exits while preserving their companies’ legacy.

Summary:
This episode of How2Exit dives into the power of communication and marketing in business sales and acquisitions. Guest Dolores Hirschmann, founder of Masters in Clarity, shares her expertise on crafting clear messaging that attracts the right buyers, partners, and investors. She breaks down the importance of strategic storytelling, leveraging public speaking, and using platforms like podcasts and events to increase business visibility—crucial for both selling a business and making acquisitions. Hirschmann also shares insights from her experience running a TEDx event, selling a business to Grant Cardone, and helping entrepreneurs build their stage presence to drive business success.

Key Takeaways:
Marketing is the Foundation of Business Success – Without clear messaging and strategic marketing, businesses struggle to grow, scale, or exit successfully. It’s not about throwing money at ads—it’s about human-to-human connection. 

Public Speaking as a Business Growth Tool – Whether you're selling or buying, putting yourself on the right stages (conferences, podcasts, networking events) can position you as an authority and attract opportunities.

Clarity Drives Deal Flow – Whether pitching investors or marketing a business for sale, clear communication about what you offer, who you serve, and your vision is key to getting the right people engaged.

The Power of Out-of-Category Marketing – Sometimes the best opportunities come from speaking to audiences adjacent to your industry—where you stand out and capture attention.

The Seven-Step Speaking Framework – Hirschmann lays out a structured way to craft a powerful talk, from grabbing attention to delivering a strong call to action.

Legacy and Liquidity in Acquisitions – As a buyer and consultant, Hirschmann helps business owners structure their companies to sell while preserving their brand’s legacy.

Networking is Key in M&A – Building relationships with CPAs, attorneys, and industry insiders can lead to acquisition opportunities that aren't publicly listed.

Content Lives Forever – A single speaking engagement or podcast appearance can be repurposed into multiple pieces of content, creating long-term value.
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Contact Dolores on
Linkedin: https://www.linkedin.com/in/dhirschmann/
Website: http://www.mastersinclarity.com/
--------------------------------------------------
💰If you’d like additional ways to support this podcast, you can become a paid subscriber here: https://how2exit.substack.com/

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Don't forget to watch 📽 Our other videos. Please check them out :

▶️Previous Episode: E268: Your Business Isn't Worth What You Think! (How to Fix It Before You Sell) - https://youtu.be/ZCwj--I0XU0

▶️E135: Sam Rosati On His Journey From Being A Lawyer To Becoming An Entrepreneur In The ETA Space - https://youtu.be/D2qJOidptRA

▶️E100: CEO Of Flippa Blake Hutchison Discusses Innovations In Buying And Selling Digital Assets - https://youtu.be/R1D5guQU9Z0

#How2Exit # # 💖Thanks for watching! 💖

Become a supporter of this podcast: https://www.spreaker.com/podcast/how2exit-buy-don-t-build-m-a-of-small-businesses--4859429/support.