What happens when a founder has the ultimate leverage... but chooses differently?

In this rare, unfiltered story from Charting Opportunities, founder John Lesnik of Lending Science DM shares his journey of building a 10X value business that caught the attention of top-tier Private Equity firms. He was weeks away from cashing a massive check when he did the unthinkable: He walked away from the PE deal.

This isn't a story about a failed sale; it's about the power of choice. John breaks down the pros and cons of selling to Private Equity versus pursuing an Employee Stock Ownership Plan (ESOP), explaining why he chose to put his people and his company culture first. This conversation is packed with hard-won lessons on:

- The critical steps to structuring your business to sell for maximum valuation.

- How to tackle major sale hurdles like customer concentration.

- The profound reason time kills all deals in the M&A process.

- Why the final decision for the business was the ESOP route.

John’s story is a powerful reminder that while money matters, a lasting legacy and culture may be the most valuable asset you can sell.

BIG THANKS to John Lesnik for being so transparent in sharing his journey with the Charting Opportunities community.

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00:00 Welcome: Charting Opportunities' 1-Year Anniversary
03:00 ESOP vs. Private Equity: The Core Decision
03:50 What is an ESOP? A Simple Definition
06:00 How We Knew It Was Time to Sell the Business
10:45 Going to Market: Hiring the M&A Firm
14:00 The First M&A Process: 383 Contacts, 7 LOIs
17:35 When the First Deal Fell Apart
19:40 Lessons Learned: Fixing Customer Concentration
22:15 Maximizing Value: Different Multiples for Different Business Lines
29:00 The Second Process and the ESOP Feasibility Analysis
37:00 The 10:30 Hour: Walking Away from Private Equity
40:55 The Biggest Hindsight Lessons (Time Kills All Deals)
45:00 Life Post-Sale: Finding Purpose and Starting Hooks of Hope
57:45 Final Thoughts and Next Speakers

ORIGINAL MEDIA SOURCE(S):

Based on the full episode "10X Your Business Selling to ESOP"
Originally Recorded on October 12, 2025 Charting Opportunities: Season 1, Episode 12
Images courtesy of: John Lesnik and Lending Science DM

In this episode of Portus Wealth Advisors' Charting Opportunities, David Vines, a practicing CPA and business attorney, provides an essential guide to the business documents that form the foundation of any successful company. He explains why meticulous record keeping isn't just about compliance but is a critical factor evaluated by potential buyers, creditors, and the IRS.

David stresses that organized, accurate, and complete documentation signals a well run business, while messy records act as a major red flag during due diligence for a sale.

David breaks down the concept of proactive legal maintenance, urging business owners to get their documents in order while things are good, not after a problem arises. He explains the serious risks of failing to observe corporate formalities, which can lead to creditors "piercing the corporate veil" and going after an owner's personal assets.

David demystifies the key differences between various business structures, including sole proprietorships, partnerships, LLCs, S-Corporations, and C-Corporations, focusing on the crucial distinction of owner liability protection.

A significant portion of the discussion is dedicated to the specific documents every business owner needs to understand. David details the nuances of partnership agreements, corporate bylaws, shareholder agreements, and LLC operating agreements.

He offers practical advice on common but costly mistakes, such as outdated "Tax Matters Partner" clauses, failing to hold and minute annual corporate meetings, undocumented shareholder loans, and the disastrous consequences of incorrect asset titling.

Through cautionary "horror stories," he illustrates how simple oversights with deeds and leases can lead to thousands in legal fees and jeopardize major transactions.

David provides actionable insights into what should be included in these agreements, from buy sell provisions to restrictions that protect a company’s S-Corp status. The conversation also covers the importance of filing annual reports to prevent administrative dissolution and the necessity of documenting major business decisions.

This episode is an invaluable resource for any business owner who wants to fortify their company's legal structure, protect their personal assets, and ensure they're fully prepared for a smooth and successful exit.

A HUGE THANK YOU to David Vines! His detailed explanations and real world examples offer crucial guidance for business owners looking to protect their assets and maximize their company's value.

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In this episode of Portus Wealth Advisors' Charting Opportunities, Andrew Ashur, founder of Lucid Bots, shares groundbreaking insights into the evolving role of robotics and AI in the modern workforce. He discusses how Lucid Bots is leveraging advanced technology to address critical labor shortages in industries like construction and cleaning, focusing on solutions that extend human reach rather than replace human touch.

Andrew delves into the fundamental problem of AI being "trapped behind a screen" and how robotic bodies enable AI to perform physically productive tasks. He highlights the shift from text-based data for AI to the need for spatial data from robot sensors, emphasizing the multi-trillion dollar market opportunity in physical AI, robotics, and domestic manufacturing. Drawing from Lucid Bots' journey, he shares the origin story of their innovative cleaning drones and pressure washing robots, driven by real-world safety concerns and efficiency needs in elevated and dangerous jobs.

A significant portion of the discussion focuses on the ethical and moral considerations of introducing robots into the workforce. Andrew explains Lucid Bots' commitment to accessibility, designing robots that empower existing workers to enhance their output rather than displacing them. He explores the long-term impact on the workforce, drawing parallels to historical shifts in agriculture and predicting the creation of new, more fulfilling jobs focused on creativity and problem-solving. He also touches on the practicalities of scaling a robotics company, including the complex interplay of mechanical, electrical, and software engineering, production challenges, and supply chain management.

Andrew provides practical insights into the future of human-robot collaboration, envisioning a Chat-GPT-like interface for robots that allows users to communicate tasks in natural language without writing code. He addresses how businesses can approach integrating robotics, emphasizing three key questions: whether robots will become more prevalent and intelligent in their industry, and if they prefer to be at the forefront of adoption. He also advises on due diligence when selecting a robotics provider, stressing the importance of site visits, understanding support and repair plans, and seeking customer testimonials for proven ROI.

A HUGE THANK YOU to Andrew Ashur! His detailed explanation and real-world examples offer invaluable guidance for business owners considering how to strategically enhance their operational efficiency and workforce capabilities with cutting-edge robotic solutions.

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Andrew Ashur - Robotics In The Workforce | Charting Opportunities

ORIGINAL MEDIA SOURCE(S):

Originally Recorded May 13, 2025
Charting Opportunities: Season 1, Episode 8
Images courtesy of: Andrew Ashur and Lucid Bots

In this episode of Portus Wealth Advisors' Charting Opportunities, Greg Brown of Cardinal Finance shares his extensive experience on the role and value of a Fractional Chief Financial Officer (CFO) for growing businesses. He delves into when it makes sense for a company to engage a Fractional CFO, what business owners should expect from such a relationship, and how to identify the right fit for their specific needs.

Greg Brown explains common red flags indicating a business might need a CFO, such as being consistently profitable but cash-poor, facing indecision due to a lack of financial data, or business owners losing sleep over financial uncertainties. He outlines his approach to initial client interactions, often starting with a specific project to understand the business and build rapport, rather than relying on checklists. Brown also discusses typical referral patterns from CPAs and banks, often triggered by growth challenges or the need for more sophisticated financial oversight to make key business decisions.

A significant portion of the discussion focuses on the pros and cons of hiring a Fractional CFO versus a full-time CFO. Brown highlights advantages of fractional support, including cost-effectiveness, access to higher-level expertise than a company might otherwise afford, and a broader perspective gained from working with multiple clients. He also addresses trade-offs, such as potential limitations on priority setting, bandwidth for very large projects, and the understanding that a fractional role may be a stepping stone to an eventual full-time hire as the business scales. Key attributes for a successful Fractional CFO were emphasized, including an accounting-oriented background, being intentionally in the fractional market (not just between full-time jobs), and having experience relevant to the client's current stage and future aspirations, such as growth or an exit strategy.

Greg provided practical insights into engagement structures, typically month-to-month, allowing flexibility for both parties. He shared examples of successful outcomes, like guiding a company from inception to a $60 million sale and helping businesses navigate financial distress or better understand their core business model and profitability drivers. Conversely, he also discussed scenarios where engagements don't work, often due to misaligned expectations, an unwillingness from the business to change, or foundational issues a CFO alone cannot fix. He stressed the importance of the business owner's commitment and clear communication, advising business owners to seek a Fractional CFO who not only has the technical skills but also makes them feel more at ease and brings a sense of calm to their financial oversight.

A HUGE THANK YOU to Greg Brown! HIs detailed explanation and real-world examples offer invaluable guidance for business owners considering how to strategically enhance their financial leadership and decision-making.

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Greg Brown - The Role of a Fractional CFO | Charting Opportunities

ORIGINAL MEDIA SOURCE(S):

Originally Recorded April 9, 2025
Charting Opportunities: Season 1, Episode 7
Images courtesy of: Greg Brown and Cardinal Finance

In this episode of Portus Wealth Advisors' Charting Opportunities, Brandon Davis, President of the Carolinas for the National Christian Foundation (NCF), offered insights into strategic charitable giving for business owners. He explained how NCF, a 501(c)(3) grant-making foundation, assists donors, advisors, and charities in developing efficient and effective giving strategies, often involving Donor Advised Funds (DAFs).

Davis detailed the mechanics of Donor Advised Funds, likening them to "charitable checking accounts" where donors make irrevocable gifts (cash, appreciated securities, complex assets), receive immediate tax deductions, and then advise on grants to charities over time. He strongly advocated for donating appreciated assets (like stocks or mutual funds) instead of cash, highlighting the significant tax advantages: receiving a deduction for the full fair market value while avoiding capital gains tax on the appreciation, ensuring more funds reach the charity.

A key focus was the strategy of gifting interests in privately-held businesses prior to a sale, an area of NCF expertise with over $6 billion in such gifts facilitated. Davis explained how NCF handles these complex transactions, becoming a temporary owner of the gifted portion (often non-voting shares). Using a C-corporation case study ($16M value, 10% gift), he demonstrated how this pre-sale gifting strategy typically results in significantly more funds reaching the intended charities (e.g., $1.6M vs $1.27M) and substantial tax savings (avoiding capital gains on the gifted portion) compared to selling the business first and then donating cash. He noted the importance of qualified appraisals (which may include valuation discounts for minority interests), due diligence on operating agreements, and timing the gift before a legally binding sale agreement exists.

Davis also clarified that Donor Advised Funds currently have no mandatory annual payout requirements, offering flexibility. He addressed potential concerns from business buyers regarding a charity co-owning shares pre-sale, stating that clear, early communication typically alleviates issues, and NCF often participates in these discussions. Ultimately, he emphasized letting the donor's passion for specific causes drive the charitable planning process, making the steps involved more meaningful and maximizing impact.

A HUGE THANK YOU to Brandon Davis and the National Christian Foundation! Brandon's detailed explanation provides invaluable guidance for business owners looking to maximize their charitable impact through strategic and tax-efficient giving.

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Brandon Davis - Strategic Charitable Giving With NCF | Charting Opportunities

ORIGINAL MEDIA SOURCE(S):

Originally Recorded March 12, 2025

Charting Opportunities: Season 1, Episode 6 (estimated)

Images courtesy of: Brandon Davis and National Christian Foundation

In this episode of Portus Wealth Advisors' Charting Opportunities, Erin Patterson JD, CPA of Erin Patterson Law shares her knowledge on estate planning for business owners, emphasizing a multi-layered approach. She stresses the foundational elements like wills, powers of attorney, and revocable trusts to avoid probate and ensure a smooth transition of assets. Patterson highlights the importance of regularly updating these documents, especially for business owners, due to the dynamic nature of businesses and tax laws.

She then delves into advanced planning, including properly funding revocable trusts and establishing buy-sell agreements to govern the transfer of business ownership in various scenarios like death, disability, or retirement. Patterson urges business owners to communicate their succession plans to key stakeholders, including family and employees, to ensure clarity and minimize potential conflicts.

Finally, she discusses legacy planning, focusing on optimizing business structure for tax efficiency and long-term value. This included strategies like creating holding companies and utilizing irrevocable trusts for tax minimization and wealth transfer. Patterson emphasizes the importance of early planning, especially before any business sale, to maximize benefits and avoid complications. She also touches upon the role of appraisals, gifting strategies, and the importance of involving financial advisors and CPAs in the estate planning process.

A HUGE THANK YOU to Erin Patterson and Erin Patterson Law LLC! Erin's expertise and concise presentation provide invaluable guidance for business owners seeking to protect their assets and plan for the future.

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Erin Patterson - Estate Planning With Erin Patterson JD, CPA | Charting Opportunities - Highlights
Erin Paterson on Portus Advisors Charting Opportunities: Highlight reel
ORIGINAL MEDIA SOURCE(S):

Originally Recorded on February 12, 2025
Charting Opportunities: Season 1, Episode 5
Images courtesy of: Erin Patterson Law, PLC and Portus Wealth Advisors

Dr. Carlos Jorge, a functional medicine doctor, discusses the impact of stress on health and aging in a presentation for Portus Wealth Advisors' ongoing business owner educational series, Charting Opportunities. He introduces the concept of blue zones, which are areas in the world where people live the longest, and highlights the importance of community, stress management, and a healthy lifestyle in achieving longevity.

Dr. Jorge emphasizes the negative effects of chronic stress on both physical and mental well-being, linking it to an increased risk of various diseases, including cardiovascular disease, diabetes, cancer, and dementia. He also notes that workplace stress is a significant contributor to overall stress levels, highlighting the importance of social connections and trust among coworkers.

The presentation also touches on the difference between lifespan and health span, with the goal being to extend the period of good health in one's life. Dr. Jorge discusses the role of inflammation in aging and how stress can accelerate this process. He offers strategies for managing stress, including mindset training, meditation, breathwork, and prioritizing sleep, nutrition, and exercise.

Dr. Jorge concludes with an overview of common chronic diseases and the importance of early detection and prevention. Dr. Jorge emphasizes the value of investing in one's health as a form of wealth and encourages viewers to take a proactive approach to their well-being.

*This comes from a 1 hour footage onsite at the CocoTiv coworking space in Charlotte, NC.


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Dr. Carlos Jorge - Managing Stress As A Business Owners | Charting Opportunities
ORIGINAL MEDIA SOURCE(S):

Originally Recorded on December 11, 2024
Charting Opportunities: Season 1, Episode 4
Images courtesy of: Dr. Carlos Jorge and Companion Health

In this episode of Portus Wealth Advisors' Charting Opportunities, Jay Ripley, Head of Investments at GEM, pulls back the curtain on the world of private equity and business acquisitions. Geared towards owners of small to medium-sized businesses, Jay provides valuable insights into what PE firms look for in potential acquisitions, how they evaluate businesses, and the current market dynamics affecting valuations.

He also offers practical advice on how business owners can prepare their companies for a successful sale, including optimizing financial reporting, improving operational efficiency, and developing a clear growth strategy. Whether you're actively considering selling your business or simply want to understand your options, this episode provides essential knowledge and expert guidance.

A HUGE THANK YOU to Jay for sharing his insights on private equity and business acquisitions with the group and with our channel followers.

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Jay Ripley of GEM - Selling Your Business to Private Equity | Charting Opportunities Highlights
Jay Ripley on Portus Advisors Charting Opportunities: Highlight reel
ORIGINAL MEDIA SOURCE(S):

Originally Recorded on November 20, 2024
Charting Opportunities: Season 1, Episode 3
Images courtesy of: Jay Ripley of GEM and Portus Wealth Advisors