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What happens to your business when you're ready to step away?In this episode of the Wise Divine Women Podcast, Dana Irvine speaks with Matt Middendorp of VisionPoint Capital about Employee Stock Ownership Plans, or ESOPs, and how business owners can approach succession, retirement, wealth, and legacy with greater intention.Matt explains how an ESOP can give qualifying U.S. business owners another option beyond selling to private equity or an outside buyer. Through an employee ownership structure, owners may be able to transition all or part of their company while protecting the culture, leadership, employees, and community they worked so hard to build.The conversation explores why business transitions should be deliberate rather than something that simply “happens” to an owner. Matt shares how succession planning involves much more than the sale price. Owners also need to consider control, identity, profitability, employee retention, company culture, future leadership, and the legacy they want to leave behind.Dana and Matt also discuss the potential benefits of employee ownership for team members, including increased engagement, stronger retention, and the opportunity to build long-term retirement wealth through the success of the company.Matt explains what types of businesses may be a good fit for an ESOP, why profitability and management alignment matter, and how a feasibility study can help owners understand the potential financial impact before making a decision.They also explore how employee ownership may apply to women-owned businesses, wellness practices, spas, yoga studios, retail companies, service businesses, and organizations with government contracts.Key TakeawaysBusiness succession should be intentional. Your transition should reflect your financial goals, personal values, leadership wishes, and vision for the future.Legacy is about more than money. For many owners, protecting employees, culture, and community matters just as much as the final sale price.Employee ownership can align interests. Employees may become more connected to the success of the company when they participate in its long-term value.ESOPs are not right for every business. Profitability, employee count, management alignment, business structure, and ownership goals all need to be considered.There is rarely only one path forward. Matt encourages owners to explore their options rather than assuming a traditional sale is the only choice.About Matt MiddendorpMatt Middendorp works with VisionPoint Capital, helping business owners explore employee ownership and determine whether an ESOP may align with their succession, financial, and legacy goals.Learn more and take the ESOP readiness assessment at:This conversation focuses primarily on ESOPs under U.S. law. Canadian business owners should seek guidance specific to Canadian employee ownership, tax, legal, and succession planning regulations.ESOP, Employee Stock Ownership Plan, business succession planning, employee ownership, business exit strategy, retirement planning, women business owners, selling a business, business legacy, private equity alternatives, employee retention, wealth building, business valuation, VisionPoint Capital, Matt Middendorp, women entrepreneurs
How will you eventually exit your business? In Part 2 of our miniseries with Christine Robinette and Bryan Reft of Fragasso Financial Advisors, host Jonathan Kersting of the Pittsburgh Technology Council explores how employee ownership and ESOPs can become a powerful succession strategy. Learn the "three legs of the stool" — personal, financial, and business goals — and why every entrepreneur should treat exit planning as present-day business strategy, not an afterthought. Whether your exit is two years or twenty away, the smartest time to start planning is now. Produced by the Pittsburgh Technology Council, this is a podcast for tech and manufacturing entrepreneurs exploring the tech ecosystem, from cyber security and AI to SaaS, robotics, and life sciences, featuring insights to satisfy the tech curious.
Kevin Donnelly was 44 when an unsolicited offer set in motion the sale of the telecommunications company he had spent nearly 20 years building. The business had grown to more than 600 people in 38 cities and about $50 million in revenue, and Kevin says the deal itself worked out well for him financially. But that doesn't mean he looks back on the experience without regret.What bothers him most is what happened to the people who helped him build the company. After the sale, employees started getting let go, and Kevin came to believe he should have done more—through bonuses, transition planning, or simply by thinking more carefully beforehand about his obligations to the people who had helped create the value he was selling. As he puts it, the way you treat those people can “come back to haunt you.”That experience, along with a brief post-sale detour into the restaurant business, eventually led Kevin to become an exit-planning advisor and to launch Inside Exits. His focus now is on owners who may not have an easy path to a conventional sale—often because of customer concentration, owner dependence, limited scale, or other issues that make a business less attractive to strategic buyers or private equity.His answer is not that every owner should pursue an ESOP or any other single structure. In fact, Kevin is explicitly agnostic. He talks about ESOPs, employee ownership trusts, worker co-ops, management buyouts, sales to existing employee-owned companies, and other creative arrangements. His goal is to help owners find a path that works financially, gives the business a chance to continue, takes care of the people who helped build it—and, ideally, leaves the owner with fewer reasons to look back with regret. The episode is brought to you by Grasshopper Bank.
In this episode of the Smells Like Money Podcast, host Suzan Chin Taylor welcomes back Chris Buttenham, CEO and Founder of REINS, to dive deep into succession planning and exit strategies for contractors and skilled trades businesses. Many owners spend decades building a business only to watch their legacy unravel after a rushed exit. Chris details why planning years in advance, reducing owner dependency, and weighing options like ESOPs, private equity, and alternative equity incentive programs are essential to safeguarding both company culture and long term financial value.Key Topics Covered:- The Reality of Succession Planning: Every business eventually shuts down or sells, making a three to ten year transition runway critical for maximum control and flexibility.- Reducing Owner Dependency: Establishing systems and incentivizing key personnel ensures the business thrives independently, raising company valuation.- Understanding ESOPs: Why Employee Stock Ownership Plans offer immense tax advantages but carry high administration costs best suited for businesses with 100 plus employees.- Navigating Private Equity and Rolled Equity: Balancing substantial payouts with operational trade offs when rolling equity into larger acquisition platforms.- Alternative Equity and Retention: Using non qualified or phantom equity arrangements to create golden handcuffs, protect legacy, and empower key team members without giving up immediate operational control.Connect with Chris Buttenham:CEO and Founder, REINSContact: chris@myreins.comLinkedIn: Chris ButtenhamWebsite: myreins.comI hope you find this episode as informative and as exciting as we have.Please let us know your thoughts about the episode!Connect with Suzan Chin-Taylor, host of The DooDoo Diva's Smells Like Money Podcast:Website: www.creativeraven.com | https://thetuitgroup.com/LinkedIn: https://www.linkedin.com/in/creativeraven/Email: raven@creativeraven.com Telephone: +1 760-217-8010Listen and subscribe here to your favorite platform:Apple Podcast - Google Podcast - Cast Box - Overcast - Pocket Casts - YouTube - Spotifyhttps://creativeraven.com/smells-like-money-podcast/ Subscribe to the Podcast:https://creativeraven.com/smells-like-money-podcast/Be a guest on our show:https://calendly.com/thetuitgroup/be-a-podcast-guestCheck Out my NEW Digital Marketing E-Course & Coaching Program just for Wastewater Pros:https://store.thetuitgroup.com/diy-digital-marketing-playbook-for-wastewater-pros#SmellsLikeMoney #BusinessExit #SuccessionPlanning #ESOP #PrivateEquity #AlternativeEquity #SkilledTrades #ContractorBusiness #EmployeeOwnership #CreativeRaven
Ever wonder what the smartest tech companies are using to win the talent war—besides just bigger paychecks? In this episode of 10 Minute Tech Talks, Jonathan Kersting of the Pittsburgh Technology Council anf TechVibe sits down with Christine Robinette and Bryan Reft of Fragasso Financial Advisors to break down equity compensation in a way that actually makes sense. Here are three reasons you should hit play right now: You'll finally understand RSUs, ESOPs, and vesting—without the jargon headache. Christine and Bryan cut through the alphabet soup of equity comp and explain how these tools actually work in plain English, from four-year vesting schedules to the tax surprises that catch employees off guard. You'll learn the hidden risk almost nobody talks about. When your salary and your wealth are both tied to the same company, you're carrying double the exposure. Bryan breaks down the 10% concentration rule and why even a great stock benefit can become a portfolio problem. You'll walk away with a competitive edge for hiring and retention. Whether you're a founder wondering if it's too late to set up an equity plan or a leader looking to out-recruit your competitors, this episode lays out exactly how giving employees real "skin in the game" changes the game entirely. This is Part 1 of a three-part miniseries on building business value through employee ownership. Fire up the RSUs and dive in. Produced by the Pittsburgh Technology Council, this is a podcast for tech and manufacturing entrepreneurs exploring the tech ecosystem, from cyber security and AI to SaaS, robotics, and life sciences, featuring insights to satisfy the tech curious.
Episode 116 – The Alphabet Soup of Employee Stock BenefitsWhy employee ownership can be a powerful wealth-building toolOverview of ESOPs, ESPPs, RSUs, and the NUA tax strategyHow ESOPs and ESPPs give you company stock through contributions or discounted purchasesHow RSUs work, when they're taxed, and why they often lead to concentrated employer stockWhat NUA is and when it can reduce taxes on appreciated company stock in a 401(k)Key risks of single‑stock exposure and why diversification is crucialPractical RSU tip: when it can make sense to sell vested shares and reinvest or pay down debtHow to think about these benefits as part of an overall financial and tax planIf you'd like help reviewing your equity compensation and overall plan, schedule a free introductory meeting at betterplanningbetterlife.com.This material is for general information and educational purposes only and is not intended to provide specific advice or recommendations for any individual.
Washington is sending new signals about employee ownership, but the headlines don't help much if you're a business owner trying to decide whether an Employee Stock Ownership Plan (ESOP) is actually doable. In this episode, Jason Miller and Makenzie Ragland welcome back Corey Rosen from the National Center for Employee Ownership (NCEO) to discuss the latest developments shaping the future of employee ownership. Corey breaks down key legislative efforts, including the Retire Through Ownership Act, the American Ownership Resilience Act, and efforts to fund the WORK Act. He also explains how the regulatory environment surrounding ESOPs continues to evolve and addresses common perceptions surrounding ESOP litigation risk and transaction costs. Other topics include the impact employee ownership can have on recruitment, retention, workplace culture, and long-term business continuity. Corey shares recent NCEO research on employee retention, explains why ownership and a strong culture work best together, and offers practical guidance for owners beginning ESOP Planning. From educating yourself on the available options to learning from existing ESOP companies, this episode provides a timely look at the Benefits of an ESOP, the Advantages of an ESOP, and what employee ownership could mean for business owners considering their next chapter. For owners seeking ESOP Advisory or professional ESOP Advisory Services, this conversation offers valuable insight into the process.
Most construction owners think they have four exit options. Pass it to a kid. Sell to an employee. Sell to a competitor. Sell to private equity. The reality is harder. Private equity passes on most contractors. Competitors often aren't buying. That's why ESOPs are now the fastest-growing succession trend in construction. Kelly Finnell, CEO of EFS ESOP Consultants, has done 22 ESOPs for general and specialty contractors in recent years. In this episode, Kelly explains how the deal is actually structured, what the owner walks away with, and where most owners are wrong about "leaving money on the table." What you'll learn: Why construction is the fastest-growing industry for ESOPs in the country The three sources of capital that fund an ESOP: bank loan, seller note, excess cash How two contractors with $3M EBITDA sold for $25M to an ESOP after $12M offers from a strategic buyer Why an owner is not personally on the hook for the ESOP bank loan How to manage the repurchase obligation so it doesn't crush you in a down year The first two moves to make if you're 58 and seriously considering this path Connect with Kelly Finnell on LinkedIn: https://www.linkedin.com/in/esopcoach/ Kelly's Website: www.execfin.com Kelly's Book, The ESOP Coach: https://www.amazon.com/ESOP-Coach-Ownership-Succession-Paperback/dp/B010CKUN9U National Center for Employee Ownership: https://www.nceo.org/ Free Succession Planning Guide: https://www.constructiongenius.com/free-succession-planning-guide
What if you could step away from your family business without walking away from everything you've built? What if your exit strategy could protect your people, preserve your culture, and secure your legacy for generations to come? "I've spent decades building this business. How do I leave without losing it?" "I don't want to sell to a buyer who will change everything we've worked for." "Is there a way to retire while keeping our employees and company values intact?" "How do I create an exit plan that benefits both my family and my team?" This conversation gives you the answer. In this episode of The Family Biz Show, host Michael Palumbos sits down with Tracy Till, former Chairman and co-founder of Butler Till, and Rob Brown, a nationally recognized ESOP attorney, to explore how Employee Stock Ownership Plans (ESOPs) can provide an alternative path for family business owners preparing for succession or retirement. Rather than viewing an exit as the end of the business, they explain how an ESOP can become a strategy for preserving company culture, rewarding loyal employees, and creating a lasting legacy. The discussion also highlights why trust, leadership development, and intentional succession planning are essential long before ownership changes hands. Meet the Guests Tracy Till is the former Chairman and co-founder of Butler Till, the Rochester-based marketing and communications firm that successfully transitioned to 100% employee ownership. Today, she serves on corporate and nonprofit boards and helps private companies strengthen governance and strategic leadership. Rob Brown is a nationally recognized attorney focused exclusively on employee ownership and ESOPs. For decades, he has advised closely held and family-owned businesses on succession planning, ownership transitions, and ESOP implementation across the United States. Together, they share practical insights from both the legal and leadership perspectives of employee ownership. Why This Episode Matters This conversation goes beyond the technical aspects of ESOPs. You'll discover why the strongest succession plans begin with culture, how trust creates future leaders, why founders often struggle to let go, and what family business owners should consider before choosing an exit strategy. The episode also explores the financial advantages of ESOPs, the importance of independent boards, and why preserving a company's mission can be just as valuable as maximizing the sale price. In This Episode, You'll Learn: Why an ESOP may be the right exit strategy for preserving your family business legacy. How employee ownership can strengthen culture, retention, and long-term growth. Why trust and leadership development are critical before any ownership transition. How boards of directors help family businesses navigate succession and strategic growth. What founders should consider emotionally and financially before stepping away. How ESOPs compare with selling to outside buyers or strategic acquirers. Why protecting your people can become one of the greatest measures of business success. Whether you're beginning to think about succession, evaluating exit strategies, or looking for ways to preserve the values your family business was built on, this episode offers practical guidance and real-world experience from leaders who have successfully navigated the journey. Listen now and discover how thoughtful succession planning can help you exit your business without losing the legacy you've worked so hard to build. Learn more and explore more Family Biz Show episodes: https://www.familybusinessflywheel.com/podcast
ESOPs are often presented as one of the best ways for a business owner to exit. You preserve your company's independence, reward the employees who helped build it, and create a retirement benefit that can be life-changing for the people who stay with the business. What gets less attention is that ESOPs are still businesses. They can lose customers. They can hit hard times. And because employees' retirement savings are often tied to the company, the stakes can be even higher than they are at a conventionally owned business.This week, Roland Burdett tells the story of Miklos Systems, a Virginia defense contractor that became an ESOP in 2006 and spent nearly two decades building an ownership culture in which employees truly thought and acted like owners. Then came the pandemic, the Great Resignation, and, most recently, the uncertainty created by DOGE and deep cuts to federal contracting. Suddenly, Roland found himself worrying not only about his employees' jobs, but about their retirement savings as well.Rather than continue rolling the dice, Miklos made the difficult decision to sell itself to a larger defense contractor. Roland takes us inside that process—from explaining the decision to employee-owners, to working with an outside trustee who ultimately had the authority to approve the deal, to the surprising complexity of unwinding an ESOP after 20 years. Along the way, he offers a refreshingly candid look at both the strengths and the limitations of employee ownership, and why, in the end, protecting the people who had helped build the company meant giving up the independence they had worked so hard to preserve. This episode is brought to you by Grasshopper Bank.
The most common question we hear may seem simple, but it can significantly change the outcome of a deal. Should you remain an S corporation or convert to a C corporation? In this episode, Jason Miller and Makenzie Wirth break down the key differences between the two structures and how each one affects the company and its selling shareholders. They also discuss the unique tax advantages associated with each approach.From S corporation tax exemptions to Section 1042 capital gains deferral, this conversation highlights the various factors that influence your decision, including ownership goals, liquidity needs, future growth plans, financing strategy, and long-term succession objectives. Whether you are just starting to explore an Employee Stock Ownership Plan (ESOP) or evaluating transaction structures, this episode provides a practical framework for understanding why there is no one-size-fits-all answer. The right structure depends on your specific goals and circumstances.
In this episode, Makenzie Wirth delves into the Mandela Effect and how our memories influence the stories we tell ourselves. Many business owners begin their exploration of Employee Stock Ownership Plans (ESOPs) with fragmented information they have gathered from the experiences of others—some of which may be accurate and some not. These stories can subtly influence significant decisions. Makenzie discusses the common misconceptions surrounding ESOPs, clarifies which elements are unique to each transaction, and highlights insights revealed during the ESOP process that can drastically alter how owners perceive employee ownership.
Host Jeremy C. Park interviews Kelly O. Finnell, Founder and President of EFS ESOP Consultants and author of "The ESOP Coach: Using ESOPs in Ownership Succession Planning," who discusses the importance and power of Employee Stock Ownership Plans (ESOPs). Kelly shares how he accidentally entered the ESOP field in 1979 while working at a law firm in Massachusetts during his first year of law school. After being assigned to research ESOPs for a white paper, he developed a passion for the topic and eventually built his consulting practice around it. Jeremy and Kelly discuss ESOPs, explaining that from a business owner's perspective it serves as an exit and succession strategy alternative to selling to private equity or strategic buyers. Kelly describes how ESOPs function as retirement plans from an employee's perspective, with the company fully funding them and the investment being limited to company stock. Jeremy notes the power of ownership, highlighting how it can transform employee perspectives and create a legacy for business leaders. Kelly discusses the performance benefits of employee-owned companies, citing academic studies and Higginbotham as examples of improved employee performance and business outcomes. Jeremy agrees with these points, sharing his firsthand experience of the positive impact on responsibility and ownership at all levels. Kelly outlines the criteria for determining if a company is a good candidate for an Employee Stock Ownership Plan (ESOP), including financial metrics like adjusted EBITDA and employee count, as well as subjective indicators such as emphasis on company culture, legacy, and philanthropy. Jeremy agrees, highlighting how outside ownership often leads to changes in culture and philanthropy, making an ESOP a viable option for preserving a business's legacy and values. Kelly advises business leaders that implementing an ESOP or any exit strategy typically requires a minimum of three years of planning and preparation. He emphasizes the importance of becoming educated about different options, including sales to private equity, and involving trusted advisors like lawyers and CPAs in the process. Kelly discusses the positive outlook for ESOPs, highlighting the bipartisan support from both Democrats and Republicans. He explains that ESOPs function as an effective wealth distribution vehicle, offering tax benefits to companies and providing a way for business owners to sell to employees with government support covering 40% of the cost through tax savings. Kelly shares contact information, including the company website www.execfin.com and LinkedIn page for EFS ESOP Consultants. He discusses his book, which was written specifically for business owners and includes case studies in plain English to explain complex ESOP topics. Visit https://execfin.com/ to learn more and connect with Kelly Finnell and EFS ESOP Consultants.
If you've owned a business for any length of time, you've probably told yourself some version of this: I'll deal with succession as soon as I solve whatever crisis my business is confronting right now. The problem, of course, is that there's always another crisis to solve or opportunity to pursue, and time has a way of passing.Jay Goltz has spent decades building a collection of successful businesses in Chicago. He knows he needs a succession plan. He knows that if something happened to him tomorrow, there'd be chaos. And he'd very much like to leave the business in the hands of the employees who helped build it. Over the years, he's considered the usual options—selling to a bigger company, to a few key employees, to an ESOP, even to an Employee Ownership Trust. But every option comes with compromises. And so, year after year, it's been easier to focus on challenges that seem more urgent—until this past April, when Jay turned 70. "I realized," he says, "I can't kick this down the road much further."This week, Jay sits down with David C. Barnett and Mel Gravely for an unusually candid conversation about what makes succession planning so difficult—even when you understand how important it is. Jay explains why he has no interest in selling, why money isn't really the issue, and why he still loves going to work every day. Mel, meanwhile, offers some tough love, suggesting that if protecting Jay's family and employees really are his priorities, then something else must be holding him back.Mel also shares an unexpected twist in his own succession journey. After stepping away from the CEO role two and a half years ago to become executive chairman, Mel found himself pulled back into operations this spring—a reminder that even well-designed succession plans don't always unfold as expected. And along the way, David offers a blunt explanation for why many aging business owners overestimate what their companies are actually worth. The episode is brought to you by Grasshopper Bank.
A global succession crisis is emerging as millions of business owners approach retirement without a clear succession plan. According to recent studies, a significant percentage of family businesses and SMEs across North America, Europe, and Asia face leadership and ownership transitions within the next decade, yet many remain unprepared. In this episode of CEO's Desk, Corum Group CEO Bruce Milne explores the growing succession challenge facing technology founders and CEOs. He discusses the risks of delaying succession planning, the realities of family succession, management buyouts, ESOPs, SPACs, and IPOs, and why mergers, acquisitions, and recapitalizations often provide the most practical path for technology companies. Whether you're actively considering a sale or simply protecting the value you've built, this video offers essential insights into succession planning, value preservation, and maintaining control of your future before circumstances force difficult decisions. Learn: Why succession planning has become a global business issue The unique risks facing technology founders and CEOs Common succession options and their limitations When to consider a merger, acquisition, or recapitalization Key questions every founder should ask before planning their next chapter Interested in learning more? Join one of Corum's upcoming Selling Up Selling Out events and explore your options before you need them. https://www.corumgroup.com/events Key Takeaways A global succession crisis is affecting businesses globally. Most recognize succession planning is critical but still lack an active plan. Technology companies face unique succession challenges Unexpected life events can dramatically change a founder's options and company value. Family succession is uncommon in technology businesses. IPOs and SPACs are not realistic exit options for most founders. The best exits are typically planned before they become necessary. Understanding your options gives you more control over your future Chapters 00:00 The Global Succession Crisis Begins 00:30 Succession Challenges Around the World 01:08 Why Tech CEOs Face Greater Risk 01:44 A Real-World Wake-Up Call 02:19 Why Succession Planning Matters 02:33 Understanding Your Succession Options 02:55 Family Succession in Technology 03:10 Management Buyouts and ESOP Realities 03:41 Why SPACs and IPOs Aren't for Most Founders 03:48 Why M&A Is the Most Practical Path 04:00 When Is the Right Time to Sell? 04:18 The Hard Questions Every Founder Should Ask 05:04 Succession Planning Is About Control 05:23 The Ultimate Founder Question 05:48 The Best Time to Plan Your Exit 05:56 Next Steps: Get Educated and Prepare
In this webinar turned podcast, Scott Becker speaks with Tom Mallon, CEO and Founder of Perpetuate Capital, about how ESOPs can provide business owners with a tax efficient succession strategy while preserving company culture, rewarding employees, and delivering competitive financial outcomes. Sponsored by McGuireWoods LLP, Perpetuate Capital, Priority Search Management, Thinkspan, Baird & Warner, Elevate […]
In this webinar turned podcast, Scott Becker speaks with Tom Mallon, CEO and Founder of Perpetuate Capital, about how ESOPs can provide business owners with a tax efficient succession strategy while preserving company culture, rewarding employees, and delivering competitive financial outcomes. Sponsored by McGuireWoods LLP, Perpetuate Capital, Priority Search Management, Thinkspan, Baird & Warner, Elevate […]
Most business owners hope to reach the day when someone offers to buy their business. If that day comes, the payoff isn't just financial. It's validation for years of risk-taking, sleepless nights, personal guarantees, and sacrifices that most employees never see. But that success can raise an uncomfortable question: What exactly do owners owe the people who helped them get there? Should employees share in the proceeds when a business is sold? Does an owner have an obligation to find a buyer who will protect the culture and the jobs that have been built over the years? Or is the owner's responsibility fulfilled by paying people well, treating them fairly, and creating a great place to work so long as the business is theirs to run?This week, Jay Goltz, Liz Picarazzi, and Ted Wolf wrestle with those questions—and not always from the same perspective. They agree that employees deserve respect and appreciation. But they also point out that employees weren't the ones who pledged their homes as collateral, absorbed the losses, or spent years wondering whether the business would survive. In other words, where should owners draw the line between gratitude and obligation?Plus: As Liz expands Citibin beyond New York City, should her marketing reflect that shift? Or should she lean into her hometown roots and emphasize that if her trash bins can make it there, they can make it anywhere? Liz also explains her plan to capture some recurring revenue.
Join us as Dr. Thomas Powell shares invaluable insights on raising capital, exiting strategies, and the importance of storytelling in entrepreneurship. Whether you're a founder, investor, or business enthusiast, learn how to navigate the complex landscape of startup growth and exit planning. In this episode: How to craft a compelling story to attract the right investors The founders' isolation paradox and ways to mitigate it Strategies for preparing a business for successful exit Common mistakes founders make in capital raising and how to avoid them The importance of systemic systems and structured planning Different investment structures including SAFE notes, equity, and recaps How to identify promising industries like fintech, medtech, and energy The benefits and pitfalls of ESOPs and employee buyouts Lessons from historic market disruptions and their relevance today Tools and frameworks for assessing risk and opportunity in startups Timestamps: 00:00 – Welcome and episode overview 02:00 – The importance of storytelling in fundraising 04:20 – The founders' isolation paradox explained 08:15 – Setting up your company for exit success 12:00 – Common pitfalls in raising capital and how to avoid them 16:30 – Structuring investments: SAFE vs equity vs debt 21:00 – How to articulate your problem and solution to attract investors 25:00 – Exit strategies: recaps, ESOPs, and sale approaches 30:00 – Industry sectors with high growth potential: fintech, medtech, energy 35:00 – The impact of AI and technology on business operations 40:00 – Preparing for the inevitable founder exit 45:00 – Risks, regulations, and market dynamics 50:00 – Practical tools for analysis and storytelling 55:00 – Closing thoughts and resources Resources & Links: The Six Secrets of Raising Early Stage Capital FoundersOffice.com The Big Short by Michael Lewis Ben and Dan Sullivan's Strategic Coach Crunchbase for market research Nate Hertz's YouTube Channel Substack for insider insights Connect with Dr. Thomas Powell: LinkedIn Twitter Optional: Explore the “Six C's” storytelling framework to sharpen your pitch Use the “Risk Probability Framework” to evaluate investments Consider strategic exit planning early in your entrepreneurial journey
Success is not just about money.In this episode of the Fatherhood, Finance and Patriotism series, Brad Frisk shares a powerful way to think about life priorities through what he calls the four cups framework: faith, family, business, and health. For entrepreneurs, fathers, and high achievers, the challenge is not just building wealth — it is learning how to keep those four cups full without losing sight of what matters most.Brad Frisk, Founder and CEO of Cypress Creek Capital Group, joins the conversation to talk about fatherhood, raising kids, building trust, financial discipline, and the constant balancing act between success and personal growth.The conversation also dives into the financial side of entrepreneurship, including exit planning, selling a business, building the right advisory team, reducing taxes, QSBS, ESOPs, IPOs, market volatility, and what business owners should be thinking about before and after a major liquidity event.But this episode goes beyond finance.It is really about how to think clearly about success, how to align your life priorities, and how to build a life that works not just on paper, but at home, in your relationships, and in the long term.______________________________________________________________If this episode inspires you to be part of the movement, and you believe, like me, that entrepreneurs are the answer to our future, message me so we can join forces to support building truly great companies in our region. -Subscribe to my channel here: https://www.youtube.com/channel/UCom_... - Mark Haney is a serial entrepreneur that has experience growing companies worth hundreds of millions of dollars. He is currently the CEO and founder of HaneyBiz - Instagram: http://instagram.com/themarkhaney Facebook: www.facebook.com/themarkhaney LinkedIn: https://www.linkedin.com/in/markehaney Website: http://haneybiz.com Audio Boom: https://audioboom.com/channels/5005273 Twitter: http://twitter.com/themarkhaney-This video includes personal knowledge, experiences, and opinions about Angel Investing by seasoned angel investors. This content is for informational purposes only and should not be construed as legal, tax, investment, or financial advice. Nothing in this video constitutes a solicitation, recommendation, or endorsement.#thebackyardadvantage #themarkhaneyshow #entrepreneur #PowerOfWith #SacramentoEntrepreneur #Sacramento#SacramentoSmallBusiness #SmallBusiness #GrowthFactory #Investor#podcast
Ep 126: What happens when the people who helped build a company become its owners? In this episode of The Retirement Success in Maine Podcast, we welcome Thomas Flynn to discuss the growing role of Employee Stock Ownership Plans (ESOPs), particularly here in Maine. Thomas explains how ESOPs work, why more business owners are choosing employee ownership over private equity or third-party sales, and how these plans can help employees build meaningful retirement wealth. We also explore the benefits and challenges of employee ownership, the importance of diversification, and what both business owners and employees should understand before making the transition. Whether you're an employee at an ESOP company, a business owner planning your exit strategy, or simply curious about this increasingly popular model, this episode provides an accessible introduction to one of the most important trends in business succession planning. Chapters: Introduction & What Is an ESOP? – Understanding employee ownership and why it's gaining momentum in Maine [00:01] Why More Business Owners Are Choosing ESOPs – Comparing employee ownership with private equity and other exit strategies [10:44] How ESOPs Build Retirement Wealth – Tax advantages, employee benefits, and the role of ownership in long-term financial security [28:16] The ESOP Process for Business Owners – What it takes to transition a company to employee ownership and what employees can expect [31:43] Managing ESOP Shares in Retirement – Diversification, retirement distributions, and common misconceptions [41:25] What Makes an ESOP Successful? – Building an ownership culture and creating lasting value for employees and business owners [54:54] Retirement Success & Final Thoughts – Thomas shares his own retirement philosophy and key takeaways for listeners [59:43]
In this episode, Jason Miller explores how advisors can recognize when an Employee Stock Ownership Plan (ESOP) deserves a place in a client's transition planning conversation. Rather than positioning ESOPs as a one-size-fits-all solution for business owners, this 14-minute field guide offers practical advice for professionals aiming to engage in meaningful discussions with clients whose objectives may align with employee ownership. From addressing common assumptions around complexity, costs, strategic buyers, seller financing, management depth, company size, and control, this episode empowers advisors with the tools to ask the right questions and identify when an ESOP deserves a closer look. Don't miss the opportunity to enhance your advisory practice and offer your clients informed and effective solutions!
Choosing the right business structure is one of the most important decisions a mission-driven business owner will make, and taxes are only part of the story. In this episode, Brian Thompson walks through every major business structure available to entrepreneurs, viewed through the lens of ownership, profit sharing, decision making, and mission protection. Whether you are just starting out, growing your team, or thinking about the best way to share profits, this episode will help you ask better questions and make a more informed decision about the structure that fits the business you are actually trying to build. In this episode you will learn: Why business structure affects ownership, profit sharing, governance, and mission protection The five questions every mission-driven business owner should ask before choosing or changing a structure Red flags that your current business structure may no longer fit your vision The key differences between sole proprietorships, LLCs, S-Corps, C-Corps, and benefit corporations Why an S-Corp may limit your ability to build a mission-driven business over time How cooperatives and ESOPs create shared ownership and democratic governance What steward ownership and purpose trusts are and why mission-driven founders should know about them The right business structure is not the one that saves the most in taxes today. It is the one that supports the mission-driven business you are trying to build over the next decade. Ownership, profit sharing, decision making, and legacy all depend on getting this right. Resources + Links Episode with D.G. Safeer Hopton on Co-Ops Episode with Brian on S-Corps Newsletter Sign Up Follow Brian Thompson Online: Instagram, Facebook, LinkedIn, X, Forbes Follow & review the podcast: on Spotify and Apple Podcasts About Brian and the Mission Driven Business Podcast Brian Thompson, JD/CFP®, is a tax attorney and Certified Financial Planner® who specializes in providing comprehensive financial planning to LGBTQ+ entrepreneurs who run mission-driven businesses. The Mission Driven Business podcast was born out of his passion for helping social entrepreneurs create businesses with purpose and profit. On the podcast, Brian talks with diverse entrepreneurs and the people who support them. Listeners hear stories of experiences, strength, and hope and get practical advice to help them build businesses that might just change the world, too.
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Plenty of companies make the move to employee ownership—ESOPs, EOTs, buyouts—and then wonder why nothing really changes. The shares transfer, the announcement goes out, and then... people still feel like employees. The ownership is technically there, but the culture hasn't caught up. In this mini episode, Rodney and Sam respond to a listener who's seen this gap firsthand and wants to know which parts of the operating system to examine first. Drawing heavily from The Ready's own experience as an EOT, Rodney and Sam make the case that ownership culture lives in three places most companies underinvest in and why checks and balances between long-term purpose and short-term operations are the structural move that makes distributed power meaningful. -------------------------------- Ready to change your organization? Let's talk! Get our newsletter: Sign up here. Follow us: LinkedIn Instagram -------------------------------- Mentioned references: ESOP (Employee Stock Ownership Plan) EOT (Employee Owned Trust) The Ready's EOT transition The Ready's OS Canvas Sound engineering and design by Taylor Marvin of Coupe Studios.
Greg Hawks is a keynote speaker, author, and corporate culture specialist who challenges leaders and teams to Act Like an Owner. For more than 25 years, he has partnered with organizations across the country to reshape culture, deepen trust, and activate ownership mindsets. Earlier in his career, Greg spent a decade as Executive Director of a nonprofit, leading teams through complex challenges and building environments where people contributed their best. That experience became the foundation for his work with companies of every size, from ESOPs and credit unions to Fortune 500 corporations and national associations. In his upcoming book, Act Like an Owner: Five Unlocks for Creating Culture People Love and Results Leaders Need, Greg introduces vivid metaphors and frameworks such as Owners, Renters, Vandals, the Five Unlocks, and the 3D Plan for designing culture intentionally. Known for his energetic presence, distinctive language, and practical strategies, Greg equips executives and employees alike to re-engage, increase accountability, and spark growth. Today, his work transforms workplaces into ecosystems where an ownership culture becomes the competitive advantage.
Fresh off the sale of Eucalyptus to Hims & Hers in a $1.6 billion deal, co-founder Tim Doyle joins Equity Mates to unpack the journey from startup idea to global healthcare platform. He shares what it was really like in the deal room, the early lessons from Koala and digital marketing, how GLP-1 medications transformed the business, why Australia needs better startup infrastructure, and what founders can learn about risk, ambition and building at scale.In this episode:00:00 – The $1.6 billion exit and signing day chaos02:49 – Why Eucalyptus decided to sell10:31 – The origins of Eucalyptus and early startup lessons17:54 – Good businesses, bad businesses and portfolio thinking26:34 – Building telehealth amid industry criticism30:52 – How GLP-1s changed everything40:53 – AI, startups and the next technology wave47:50 – ESOPs, startup talent and the future of Australia's ecosystemETFs and Stocks mentioned: Meta Platforms (NASDAQ: META), Alphabet (NASDAQ: GOOGL), Eli Lilly (NYSE: LLY), Novo Nordisk (NYSE: NVO), Amazon (NASDAQ: AMZN), Netflix (NASDAQ: NFLX), Atlassian (NASDAQ: TEAM), Woolworths Group (ASX: WOW)———Want to get involved in the podcast? Record a voice note or send us a messageAnd come and join the conversation in the Equity Mates Facebook Discussion Group.———Want more Equity Mates? Across books, podcasts, video and email, however you want to learn about investing – we've got you covered.Keep up with the news moving markets with our daily newsletter and podcast (Apple | Spotify)We're particularly excited to share our latest show: Basis PointsListen to the podcast (Apple | Spotify)Watch on YouTubeRead the monthly email———Looking for some of our favourite research tools?Download our free Basics of ETF handbookOr our free 4-step stock checklistFind company information on TIKRResearch reports from Good ResearchTrack your portfolio with Sharesight———This podcast is intended for education and entertainment purposes only. Any advice is general advice and has not taken into account your personal financial circumstances. Before acting on general advice, you should consider if it is relevant to your needs. If unsure, speak to a financial professional. The host of this podcast and their guests may have positions in the companies mentioned. Equity Mates Media is part of the Betashares Group but maintains editorial independence and operates under Australian Financial Services licence 540697. Hosted on Acast. See acast.com/privacy for more information.
Chirag Taneja built GoKwik into 1 in 5 D2C checkouts in India. But the path there was a series of bets that didn't work, jobs that didn't last, and one moment in 2020 where the suitcases for Canada were packed and waiting in his living room.In Episode 12 of Unstarted, Chirag sits down with Avnish Bajaj to talk about what it actually means to keep tinkering, and when tinkering becomes the thing that holds you back.They get into: 1. What's really important to start a business: idea, capital, or knowledge? 2. Why choosing the right problem matters more than solving any problem 3. The Canada PR that almost happened (and the suitcases that are still in his house) 4. Probabilistic thinking, and why "generate choices" beats "make decisions" 5. Should you have a co-founder you don't already know? 6. How he thinks about ESOPs, the size of the pieUnstarted is a Z47 series. For founders, by founders. New episode every Thursday.Chapters 00:18 From the shop floor to a 1-in-5 D2C company01:35 A banker father, a single parent, and "play with intent"03:15 Why he chose Delhi College over IIT Delhi Civil05:30 The first Asian team to build a Formula race car06:25 The Maruti bet that landed him on the shop floor07:10 Q: Idea, capital, or knowledge — what matters most?08:50 How Bombay Shaving Company became the foundation of GoKwik09:35 The right problem matters more than the right solution10:55 Payments were broken in 2005. They were still broken in 2017.11:50 Pick your game: badminton or golf?13:20 The Canada PR, the suitcases, and the trip that never happened15:25 Generate choices before you make decisions17:50 When the tinkerer turns on himself19:15 Why "what worked then" stops working at 1-to-1022:45 Q: When should you have a co-founder?24:45 Why arranged co-founders are too risky28:30 Closing
In this episode of Journey to an ESOP and Beyond podcast, Jason and Mackenzie discuss the full lifecycle of an ESOP company. The conversation covers what changes in the first 90 days after an ESOP transaction, including new debt obligations, administrative responsibilities, and the importance of employee communication and engagement. The podcast also discusses how boards and leadership teams evolve over time, why committee structure matters, and how companies can successfully navigate the growing complexities of mature ESOPs. From early-stage growing pains to long-term planning challenges like diversification, repurchase obligation, and balancing opportunities between long-tenured employees and newer participants, this episode provides a practical and candid look at what it truly means to operate as an ESOP company for the long haul.
In this episode of the Journey to an ESOP podcast, Jason and Makenzie interview brothers Marc and John Farrell of to discuss their company's transition to employee ownership and the multi-generational legacy behind it. The Farrell brothers share the history of their 80-year family business, why they chose an ESOP over other transition options, and what they've learned in the early stages of becoming employee owned. From succession planning and leadership transitions to culture and communication, this conversation offers practical insight for business owners thinking intentionally about the future of their company.
>> Get A Free Copy Of The Book (Big Idea To Bestseller): https://www.bigideatobestseller.com/free-book>> Book A Call With Our Team: https://write.bigideatobestseller.com/booking-page>> Step-By-Step Process To Becoming A Bestselling Author: https://write.bigideatobestseller.com/vsl-watch-pageIG: @jakekelferLinkedIn: @jakekelferDiscover how Bob Whalen uses ESOPs to help owners secure their future, reward staff, and protect their legacy. Learn to build a thriving, trust-based culture and a smarter succession plan. Tune in now to transform how you grow and exit your business.>>LINKEDIN: https://www.linkedin.com/in/bob-whalen-4023a21b/>>BOOK LINK: https://a.co/d/00dCnIeR
We weren't aware of ESOPs before this conversation, and chances are you haven't heard of them either. Employee Stock Ownership Plans can drastically change how you run your business and transform the lives of your employees. Publix is one of the best examples of making their employees' lives better. Cashiers who may never make more than $20 an hour but stay there 20-30 years retire as multimillionaires because of employee ownership. Matt Middendorp helps business owners understand this transition option that most have never heard of. He started working at an ESOP company in college without knowing what it meant, but recognized the culture felt completely different from corporate retail. People collaborated and took ownership of problems instead of waiting for someone else to solve them. Matt Middendorp helps business owners explore this transition option. He started working at an ESOP company in college without knowing what it meant, but recognized the culture felt completely different from corporate retail. People collaborated and took ownership of problems instead of waiting for someone else to solve them. We talk about how ESOPs work, why they offer better tax benefits than other transitions, what makes a business a good fit, and how this approach solves problems for both owners looking to exit and employees building toward retirement.HighlightsHow employee ownership changes company culture when people take ownership of problems instead of waiting for others to solve them.Why ESOP companies grow faster than non-ESOP companies once employees have real financial stakes in success.The tax advantages that make ESOPs attractive for both sellers and companies compared to other transition options.What makes ESOP transactions collaborative instead of the combative due diligence process with private equity or strategic buyers.How long-term employees build wealth that solves the retirement gap many Americans face.Make sure to subscribe to Blue Collar BS where we talk about the real gaps between generations in blue collar work and what it takes to lead across different age groups in today's trades. Be the first to hear conversations like this that introduce options you didn't know existed and challenge what you thought was possible in business.Get in touch with Matt: WebsiteLinkedInPhone - 715-897-0879Get in touch with us:Check out the Blue Collar BS website.Steve Doyle:WebsiteLinkedInEmailBrad Herda:WebsiteLinkedInEmailThis podcast uses the following third-party services for analysis: Podtrac - https://analytics.podtrac.com/privacy-policy-gdrpOP3 - https://op3.dev/privacy
What does it take to create an ownership culture when most employees don't literally own the business? In this episode, Kevin talks with Greg Hawks about the mindset shifts leaders need to make to help people act like owners by bringing more of their heart, head, and hands to work. Greg explains how his framework of owners, renters, and vandals influences behavior and why leaders must pay close attention to the environments they create. He shares how organizations unintentionally produce renters by limiting contribution, tolerating toxic behaviors, and failing to help people see the bigger picture. They also discuss why the desire for responsibility is often driven by more than money, how leaders can broaden the circle, so people think beyond their own "room" in the house, and why shaping a culture of trust, contribution, and shared perspective is one of the most important responsibilities any leader has. Listen For 00:00 Why Ownership Mindset Matters (Beyond Financial Ownership) 00:38 Creating an Ownership Culture 02:54 The Big Idea: Why Acting Like an Owner Changes Everything 03:42 What "Ownership" Really Means at Work and in Life 05:20 The 3 Workplace Mindsets: Owners, Renters, Vandals 06:20 How Each Mindset Shows Up (Heart, Head, and Hands) 07:21 The Real Problem: Why Vandals Drive Disengagement 08:23 The Tipping Point Strategy: Reduce Vandals, Grow Owners 09:01 Should You Fix or Remove Toxic Employees? 10:11 Why Organizations Tolerate "Vandals" 12:08 Leadership Responsibility vs. Labeling People 14:05 How Leaders Accidentally Create "Renters" 14:35 The Power of Contribution in Building Ownership 16:32 "Reach for Responsibility" – The Key to Ownership 23:05 Breaking Silos: Widening Perspective Across Teams 28:03 Final Leadership Insight: Culture Shapes Everything Greg's Story: Greg Hawks is the author of Act Like an Owner: Five Unlocks for Creating Culture People Love and Results Leaders Need. He is a keynote speaker and corporate culture specialist who challenges leaders and teams to Act Like an Owner. For more than 25 years, he has partnered with organizations across the country to reshape culture, deepen trust, and activate ownership mindsets. Earlier in his career, Greg spent a decade as Executive Director of a nonprofit, leading teams through complex challenges and building environments where people contributed their best. That experience became the foundation for his work with companies of every size, from ESOPs and credit unions to Fortune 500 corporations and national associations. Known for his energetic presence, distinctive language, and practical strategies, Greg equips executives and employees alike to re-engage, increase accountability, and spark growth. https://www.greghawks.com/ https://www.linkedin.com/in/ghawks https://www.instagram.com/greghawks/?hl=en Looking to Develop Stronger Leaders? Want help developing the leaders in your organization? Reach out to explore how the Kevin Eikenberry Group can support your team. info@kevineikenberry.com Book Recommendations Act Like an Owner: Five Unlocks for Creating Culture People Love and Results Leaders Need by Greg Hawks Right Kind of Wrong: How the Best Teams Use Failure to Succeed by Amy C. Edmondson Like this? Compassionate Accountability with Nate Regier How Leaders Can Inspire Accountability with Michael Timms Leave a Review If you liked this conversation, we'd be thrilled if you'd let others know by leaving a review on Apple Podcasts. Here's a quick guide for posting a review. Review on Apple: https://remarkablepodcast.com/itunes Join Our Community If you want to view our live podcast episodes, hear about new releases, or chat with others who enjoy this podcast join one of our communities below. Join the Facebook Group Join the LinkedIn Group
In this episode, Jason Miller speaks with Steve Baker of The Great Game of Business about the critical role of financial literacy in building successful employee ownership and ESOP cultures. They explore why ownership alone does not automatically create an ownership mindset and why education is essential for helping employees understand how businesses actually work. Steve shares practical insights on how organizations can strengthen engagement, accountability, and performance by teaching teams to think and act like owners through a deeper understanding of financials and business performance. The conversation highlights a key takeaway for ESOP companies and leadership teams: financial literacy is the foundation that connects employee ownership to real behavioral change and long-term business success.
In recognition of April as Financial Literacy Month, this episode explores an important question: what happens when employees are given ownership but don't fully understand its value? Jason and Makenzie dive into the critical role financial literacy plays in helping employee-owners make the most of their ownership stake. From understanding equity to building confidence in financial decision-making, this conversation highlights how empowering employees with knowledge can unlock the full potential of employee ownership.
For many family business owners, the succession question is more complicated than it looks — especially when some family members want to stay involved, others don't, or there's simply no heir apparent willing or able to take the reins. An Employee Stock Ownership Plan can bring remarkable clarity to exactly these situations. Kelly O. Finnell, J.D., CLU, AIF®, President of EFS ESOP Consultants and one of the nation's foremost ESOP authorities, joins Pat, Walter, and Corby to explore how ESOPs can serve as a powerful and often underutilized tool in family business succession planning. With more than 40 years helping business owners design and execute ESOPs — and author of the preeminent guide The ESOP Coach: Using ESOPs in Ownership Succession Planning — Kelly brings unmatched depth to this conversation. He covers the general parameters for when an ESOP makes sense, the specific benefits in a family business context, how ESOPs can minimize taxes while maximizing shareholder legacy, and why owners with no clear successor should be looking hard at this option.Conversations that move you closer to a regret-proof exit. Subscribe To The Channel By Clicking HERE!Learn more about Pat and Walter: https://ennislp.com/about CONNECT ON SOCIAL MEDIA:YouTube: https://www.youtube.com/channel/UCOwUmJP3Fm4rYbRAQhYQkpg ExitReadiness Blog: https://ennislp.com/read-our-blogFacebook: https://www.facebook.com/exitreadinessWebsite: Ennislp.com#PatEnnis #WalterDeyhle #ExitReadinessDISCLAIMER: The information in this presentation is provided as education only. Neither the presenter nor ENNIS Legacy Partners is engaged to render legal, accounting, or other professional services. Consult a qualified professional for advice specific to your situation. ENNIS Legacy Partners assumes no legal liability for any loss related to information contained in this presentation.
What's the right first question when an owner starts exploring an ESOP? It may not be “Can my company do one?” In this episode, we unpack why technical possibility and strategic fit are not the same thing. Using the metaphor of the kitchen in a family home, we explore what owners are really trying to preserve, strengthen, and pass on through transition — and why an ESOP works best when it supports the fundamentals rather than distracting from them. A thoughtful conversation for owners considering employee ownership, succession, continuity, and legacy.
In this episode of Poised for Exit, Steve Storkan, Executive Director at The Employee Ownership Expansion Network, discusses how employee ownership is gaining traction as a business exit strategy. He shares the growth of employee ownership across the U.S. and explains why more business owners are considering it as part of their transition planning.Steve breaks down how increased awareness, new sources of capital, and impact investing are making employee ownership more accessible. He also highlights research showing the significant wealth created for employees through these models, along with the flexibility and legacy benefits for business owners.This conversation explores the different forms of employee ownership, including ESOPs, and what makes a company a good fit. Steve also emphasizes the importance of having the right advisors and ensuring strong financial feasibility when considering this path.This episode offers a practical look at how employee ownership can support both successful exits and long-term business continuity. Connect with Steve Storkan hereLearn more about The Employee Ownership Expansion Network hereConnect with Julie Keyes, Keyestrategies LLCFounder, Consultant, Author, Pod-caster and Instructor
The importance of early succession planning, cannot be overstated for business owners. Tim Staton and Byron McFarland emphasize that starting the process as soon as possible—ideally years in advance—makes a huge difference. Many owners procrastinate until their seventies, but building an exit strategy early helps you get paid properly and maximize the sale value of a business. Byron suggests a three-year lead time for a solid plan that ensures the owner gets compensated, while committing to seven years can secure the full value of a business. This proactive mindset lets owners envision life after the business, reducing delays and emotional hurdles when selling a business. A common pitfall is overestimating your company's worth, often because owners enjoy a lifestyle funded by pre-tax dollars. Normalizing those expenses reveals the true financial picture and impacts how to evaluate value of a business. Key methods include looking at multiples of EBITDA, discounted cash flow, or comparable sales—far beyond just the book value of a business or simple asset tallies. Owners often hear "four times EBITDA" as a benchmark, which might be the ceiling for smaller businesses relying heavily on bank financing. Larger buyers, like private equity firms, can offer higher multiples (six to eight times EBITDA) due to their capital structure. When considering exit options, owners typically have three paths: selling to a management team (internal buyout), to an external buyer (strategic, financial, or owner-operator), or via an Employee Stock Ownership Plan (ESOP). Selling to management demands heavy preparation to create "bankable buyers"—employees with an ownership mindset, strong emotional intelligence, and the ability to handle stress, personal guarantees, and risks like pledging assets. These buyers must be groomed in finance, risk management, and HR to qualify for buying a business loan, often through SBA-backed options or bank financing in phased transactions. External buyers frequently pay premium multiples because they inject more equity. ESOPs provide timing flexibility but add complexity. Buying and selling a business involves significant risks on both sides. For owners, risks of business ownership extend into the exit phase, including financial exposure from personal guarantees and the emotional toll of letting go—founders often tie their identity so deeply to the company that they experience breakdowns or last-minute "red zone fumbles," finding excuses to back out even when the deal benefits them financially. Potential internal buyers may walk away once they fully understand these commitments. To minimize risks and boost the sale value, engage key employees early. Share your vision for the company's future to foster loyalty and prevent talent loss (as in cases where key staff departed after a surprise sale announcement, slashing the price by 25%). Make employees "heroes" in due diligence by highlighting their expertise—this lowers buyer-perceived risk and can increase the final price. Discuss aspirations with your team to align goals and build buy-in. The steps to selling a business generally include early valuation, cleaning up financials, assembling a deal team (brokers, advisors, attorneys), identifying buyers, negotiating terms, and handling due diligence and closing. Preparation is key—whether selling a business near me locally or to a broader market, thorough planning ensures a smoother transition. In this episode, Byron McFarland dives deep into the nuances of business succession planning, stressing preparation, creating bankable successors, and addressing the financial and emotional challenges of when selling a business. He reminds us that people are at the heart of any organization—understanding their needs and risks is essential for a successful exit and long-term value. Connect with Byron Website: https://www.themcfarlandgroup.com/ LinkedIn: www.linkedIn.com/in/byronkmcfarland Website: https://thebankablebuyer.com/ Connect With Tim Website: timstatingtheobvious.com Facebook: https://www.facebook.com/timstatingtheobvious YouTube: https://www.youtube.com/channel/UCHfDcITKUdniO8R3RP0lvdw Instagram: @TimStating TikTok: @timstatingtheobvious LinkedIn: https://www.linkedin.com/in/tim-staton-04b41a271/ SKOOL Community: https://www.skool.com/timstatingtheobvious-9537/about?ref=de9c7e65d8ba4eeabc1a8eea413c125b
In this episode of The Matt Feret Show, Matt Feret sits down with ESOP consultant Matt Middendorp to explore how employee ownership is reshaping the way people think about work, wealth, and career fulfillment—especially in midlife. Moving beyond traditional conversations about retirement or business exits, the discussion examines Employee Stock Ownership Plans (ESOPs) as an alternative model that aligns employee success with company performance. Middendorp shares real-world insights into how employee-owned companies foster stronger cultures, higher retention, and long-term financial security while offering business owners a legacy-driven transition strategy outside of private equity or layoffs. Together, they unpack why so many professionals have never heard of ESOPs, what employee ownership teaches us about purpose and identity at work, and how individuals at any career stage can rethink success, stability, and the value they help create.The Matt Feret Show is about thriving in midlife, retirement, and beyond. Each week, Matt shares smart conversations on Medicare, Social Security, retirement planning, health, wealth, wellness, caregiving, and life after 50.Explore more episodes and sign up for The Matt Feret Newsletter: TheMattFeretShow.comNeed Medicare help? Book a no-obligation consultation: BrickhouseAgency.comWatch full episodes on YouTube: The Matt Feret ShowSubscribe on Apple, Spotify, or YouTube for more insights on wealth, wisdom, and wellness in retirement. Hosted on Acast. See acast.com/privacy for more information.
In this episode of the Foundations of Transition series, Jason and Makenzie focus on the theme of Communication, Culture & Trust, exploring how these elements shape the success of an ESOP transaction. Each workshop-style conversation in this series is designed to help business owners think more intentionally about the future of their company and the role they play in shaping it. This episode encourages owners to consider not just the structure of a transition, but the human side of the process. Jason and Makenzie discuss why clear communication, a healthy company culture, and strong trust between leadership and employees are essential to building momentum and confidence throughout an ESOP journey. Through practical insights, they unpack how intentional communication and cultural alignment can reduce uncertainty and help create a smoother, more successful transition for everyone involved.
(0:00) Intro (1:40) About the podcast sponsor: The American College of Governance Counsel (2:26) Start of interview (3:19) Eric's origin story (5:00) The Lean Startup Journey (10:23) About The Long-Term Stock Exchange (18:00) Governance and Eric's New Book Incorruptible (24:14) On Governance in Startups vs. Public Companies and so-called "best practices." "One of the key ideas in the book is that it's always too early until it's too late." (28:37) Why the title Incorruptible. How to become an incorruptible force for good in the world. (33:15) The board members' sacred obligation. The call for a director's oath. (34:40) The concepts of Financial Gravity and Career Equity. "The force that no one controls, but everyone obeys." "The number one thing CEOs notice before and after the IPO: every employee is looking at the stock ticker every day." (41:38) Innovations in AI Governance (OpenAI, Anthropic, etc) "A new old idea" (44:36) On the Public Benefit Corporation (PBC) structure. (46:25) The Case for New Governance Structures. "The shareholder primacy debate has become completely divorced from the actual material interests of shareholders." The example of Costco. (52:45) On Dual-Class Share Structures. "I don't think emperor for life is a great political system" "[The] standard governance [model] has to be really bad for dictator for life to be an improvement." "I'm interested in trying to create what I call the architecture of institutional longevity. What would it take to create organizations that can endure for decades or even centuries? In order to do that, by definition, we have to find ways to encode the ethos." (56:51) Mission-Locked Constellations. "Structures that involve many different entities that are locked together to act as a bit of an immune system against corruption." "The spiritual holding company: a constellation of multiple entities where some entity has the responsibility of being at the center to provide basically mission protection as a service to the for-profit entities under its purview." (1:01:07) The Novo Nordisk story. *reference to the Acquired podcast episode. (1:07:10) Books that have greatly influenced his life: The Machine that Changed the World, by James P. Womack, Daniel T. Jones, and Daniel Roos (1990) Toyota Production System, by Taiichi Ohno (2001) Toyota Way, by Jeffrey Liker (2003) Dune, by Frank Herbert (1965) The Dawn of Everything, by David Graeber and David Wengrow (2021) The Enlightened Capitalists, by James O'Toole (2019) (1:12:20) His mentors. Steve Blank, Ken Duda, Maliz Beams, Dario Amodei, Brian Chesky, Matthew Prince, Sid Sijbrandij, Dustin Moskovitz, James Reinhart, Todd Park. (1:14:00) Quotes that he thinks of often or lives her life by "Nothing real can be threatened, and nothing unreal exists" (from A Course in Miracles) (1:15:25) An unusual habit or an absurd thing that he loves (1:16:08) The living person he most admires Eric Ries is the Creator of the Lean Startup method and author of The Lean Startup, he has spent two decades reshaping how companies are built and managed. He is also the founder of the Long-Term Stock Exchange (LTSE) and host of The Eric Ries Show podcast. More info on his latest book Incorruptible here. You can follow Evan on social media at:X: @evanepsteinLinkedIn: https://www.linkedin.com/in/epsteinevan/ Substack: https://evanepstein.substack.com/__To support this podcast you can join as a subscriber of the Boardroom Governance Newsletter at https://evanepstein.substack.com/__Music/Soundtrack (found via Free Music Archive): Seeing The Future by Dexter Britain is licensed under a Attribution-Noncommercial-Share Alike 3.0 United States License
This week, Jason and Makenzie cover what could go wrong in an ESOP transaction. From concerns about overpaying for shares to the burden of debt service, unrealistic projections, and the momentum that can build during negotiations, this episode unpacks the risks that can make an ESOP feel “off track” and what causes those outcomes. Jason and Makenzie explore the difference between a deal that is truly broken and one that simply needs course correction, offering an honest look at the warning signs, human dynamics, and importance of sustainable structure.
In this episode, Jason and Makenzie walk listeners through the step-by-step process of an ESOP transaction, breaking down what can often feel like a complex and overwhelming journey into a clear, approachable roadmap. They cover common questions business owners often ask at the start of the process, including: How do I know if my company is a good fit for an ESOP? and who should be involved? From evaluating readiness to understanding the key players involved, Jason and Makenzie share practical insights on who to engage first, what steps to expect, and how to navigate the early stages of exploring employee ownership with confidence.
In this episode, Jason and Makenzie explore what is often one of the most challenging roles in an ESOP transition: frontline management. Immediately after a transition to employee ownership, frontline managers often take on the greatest level of responsibility as they help employees navigate change while keeping the business moving forward. Jason and Makenzie unpack six key threads that can help frontline managers better support their teams and guide the company through a successful transition.
Ted speaks with Rich Gioia, co-founder of Gioia Capital and Managing Director of Lazear Capital, an investment banking firm specializing in ESOP transactions. Rich shares his path from leaving a legal career to acquiring and growing businesses in the lower middle market, eventually discovering the advantages of Employee Stock Ownership Plans while selling one of his companies. The conversation breaks down how ESOPs work as a business succession strategy, including how owners can sell their company while maintaining control, receiving liquidity, and potentially eliminating capital gains taxes through unique provisions in the tax code. Rich explains the structure of ESOP transactions, including bank financing, seller notes, and equity warrants, while demystifying common misconceptions that employee ownership is purely altruistic or requires employees to contribute capital. Ted and Rich also explore why ESOPs are particularly relevant for contractors, builders, and other owner-operated businesses where private equity interest may be limited. They discuss the importance of succession planning, preserving legacy, and aligning incentives between ownership and employees. The episode highlights how ESOPs can create a win-win structure—providing business owners with liquidity and tax advantages while giving employees a meaningful ownership stake and incentive to drive long-term success. TOPICS DISCUSSED 01:10 Introduction & Meeting Rich Gioia at Sundance 02:45 Rich's Background: Lawyer to Entrepreneur 04:45 Building Companies in the Lower Middle Market 06:40 Selling a Business & Discovering ESOPs 09:00 Common Misconceptions About ESOPs 11:20 Why ESOP Exits Can Outperform Traditional Sales 13:30 How ESOP Financing Works 16:00 Breaking Down a Real ESOP Transaction Example 19:00 Tax Advantages & Section 1042 Explained 22:30 Employee Ownership Without Financial Risk 24:40 Why More Businesses Don't Consider ESOPs 27:30 Legacy, Ownership & Selling to Employees 30:00 Incentives, Productivity & Employee Alignment 32:20 Exit Planning for Contractors & Builders 35:00 Private Equity vs. ESOP Outcomes 37:40 Preserving Company Culture & Legacy 40:10 ESOPs as a Succession Strategy 42:30 Final Thoughts & How to Learn More About ESOPs CONNECT WITH GUEST Rich Gioia Website LinkedIn KEY QUOTES FROM EPISODE “You as a business owner could sell your company effectively tax-free, tax-deferred and ultimately eliminated.” “Your employees don't contribute any cash in an ESOP.” “There are no personal guarantees with that and the employees aren't raising or contributing any capital.”