From Chaos to Clarity: Building Enduring Service Businesses - John Barrett - Executive Director at ISSA

Reinventing Legal Services w/ Fractional Counsel - Rachel Saunders, Founding Partner @ Saturday Legal

Rachel Saunders joins Seth Deutsch on Diners and Deals for a candid conversation about her unconventional path from big law to private equity to launching her own firm. She reflects on the mindset shift required to move from mitigating risk as a lawyer to taking risks as an entrepreneur, and how pivotal experiences—like investing in NFTs and running a crypto company—shaped her confidence to bet on herself. Rachel shares the lessons learned from building Saturday Legal, her vision for delivering legal services differently, and the personal values that guide her as a mother and founder. We discuss: * The transition from being "entrepreneurial" to fully embracing entrepreneurship * Lessons from private equity and operating a crypto company through volatile markets * The importance of taking personal risks to strengthen decision-making * Building Saturday Legal on a flat-fee, client-first model instead of billable hours * Balancing professional ambition with being fully present for family This episode offers practical insight for anyone navigating career transitions, entrepreneurship, or redefining what success looks like on their own terms. Links: Saturday Legal - https://saturday-legal.com/ [https://saturday-legal.com/] Rachel on LinkedIn - https://www.linkedin.com/in/rachel-b-saunders/ [https://www.linkedin.com/in/rachel-b-saunders/] Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/ [https://www.linkedin.com/in/sethdeutsch/] Topics: (00:00:00) - Intro (00:03:53) - Introducing Saturday Legal (00:05:36) - From entrepreneurial to entrepreneur (00:11:21) - Influences and upbringing (00:13:17) - Journey through education and early career (00:15:35) - Law school and early legal career (00:20:27) - Transition to Peak Six (00:26:16) - Learning to take risks (00:29:23) - The thrill of NBA Top Shot (00:30:37) - From investor to CEO: Embracing the unknown (00:31:06) - Navigating imposter syndrome (00:31:47) - The reality of operating a business (00:35:01) - The crypto company journey (00:39:48) - The decision to bet on myself (00:45:41) - The path to starting a law firm (00:56:13) - Balancing career and family (00:57:48) - Final thoughts and words of wisdom

From Immigrant Grit to Transforming the Law Firm Model - Andy Kvesic - CEO of Aprio Legal

In this episode of Diners and Deals, host Seth Deutsch sits down with Andy Kvesic for a candid conversation about his unconventional career path and entrepreneurial journey. From growing up as the son of Croatian immigrants in Arizona, to building a successful legal career, pivoting into public service as a prosecutor, and eventually founding a pioneering law firm, Andy shares the pivotal choices and lessons that shaped his path. Their discussion explores resilience, risk-taking, and the vision behind transforming the legal industry through innovative ownership structures and integrated professional services. They discuss: * The resilience and independence Andy developed growing up in an immigrant family and how it influenced his career * His pivot from private practice to becoming a prosecutor and why that experience became a springboard for his future success * How Arizona's regulatory changes enabled the creation of his pioneering law firm and opened the door for non-lawyer investment in legal services * The challenges and breakthroughs of scaling a business, navigating private equity, and going through a transaction without a playbook * The values he hopes to pass on to his children about building, learning, and leaving the world better than they found it This episode is for entrepreneurs, professionals, and anyone interested in the intersections of law, business, and personal resilience. Links: Aprio - https://www.aprio.com/ [https://www.aprio.com/] Andy on LinkedIn - https://www.linkedin.com/in/andy-kvesic-01b1ba7/ [https://www.linkedin.com/in/andy-kvesic-01b1ba7/] Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/ [https://www.linkedin.com/in/sethdeutsch/] CSuite Financial - https://csuitefinancialpartners.com/ [https://csuitefinancialpartners.com/] Topics: (00:00:00) - Intro (00:04:39) - Andy's early life and immigrant background (00:12:35) - From college to law school (00:17:39) - The call to public service (00:23:39) - The entrepreneurial leap (00:31:20) - Navigating the legal industry's evolution (00:33:40) - Non-lawyer ownership in law firms (00:36:19) - The vision for a comprehensive professional services firm (00:38:16) - Challenges and opportunities in building the firm (00:39:07) - The unexpected offer and decision to sell (00:42:25) - Navigating the emotional rollercoaster of a business sale (00:46:50) - Post-sale reflections and future plans (00:52:54) - Final thoughts and advice for entrepreneurs (01:08:53) - Closing remarks

From Chaos to Clarity: Building Enduring Service Businesses - John Barrett - Executive Director at ISSA

In this episode of Diners and Deals, host Seth Deutsch sits down with his longtime friend John Barrett to trace the pivotal moments of John's career—from earning a life-changing Evans Scholarship to learning the ropes at Xerox, turning around broken service businesses, and ultimately leading ISSA, a trade association serving over 11,000 members across 130 countries. John opens up about what really matters in business and life, sharing hard-won wisdom on resilience, humility, and the power of staying curious. They discuss: * Why cash equals time, and how that truth shaped his approach to turnarounds and growth * Lessons in humility and leadership from corporate America and chaotic service businesses * How John scaled Chemco from two states to a 10,000-employee national player * The strategic exit to Compass Group and what he learned from a near-catastrophic customer concentration issue * His reflections on ambition, self-awareness, mentorship, and legacy as he prepares to retire A compelling listen for entrepreneurs, operators, and anyone navigating the messy, meaningful road of business building. Links: John on LinkedIn - https://www.linkedin.com/in/john-barrett-a634624/ [https://www.linkedin.com/in/john-barrett-a634624/] ISSA - https://www.issa.com/ [https://www.issa.com/] Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/ [https://www.linkedin.com/in/sethdeutsch/] Topics: (00:00:00) - Intro (00:02:57) - John's early life and career beginnings (00:04:21) - Hanukkah memories and personal stories (00:07:02) - John's role at ISSA (00:10:08) - John's upbringing and family life (00:15:14) - College years and early career aspirations (00:20:58) - Journey at Xerox and transition to the service industry (00:38:07) - Mastering cashflow forecasting (00:38:15) - Lessons from recessions and turnarounds (00:39:28) - The brutal reality of layoffs (00:40:25) - The importance of mentorship (00:42:48) - Navigating family-owned businesses (00:45:56) - Scaling and cash management (00:50:11) - Customer concentration risks (00:52:46) - Selling to private equity (01:01:17) - The journey with SMS (01:05:36) - Reflections on leadership and legacy (01:13:11) - Concluding thoughts and farewell

From Stuntman to Service Empire: Building with Grit and Purpose - Josh Zolin - CEO of Windy City Equipment

In this episode of Diners and Deals, I sit down with Josh Zolin, CEO of Windy City Equipment, to talk about what it takes to build a service business that scales—without losing your soul. Josh started his career as a Hollywood stuntman before joining his father's one-man repair operation. Over time, he helped transform the company into a multi-state commercial kitchen equipment service provider, while staying deeply connected to the skilled trades. We dig into Josh's journey of self-discovery, from identity struggles and career pivots to a defining personal tragedy that reshaped how he leads. He shares how he built a values-driven company culture, why presence matters more than growth at any cost, and how writing his book Blue Is the New White helped him advocate for the next generation of skilled workers. We also cover: * The challenges of scaling high-trust service operations * What it takes to expand into new markets—and when to pull back * Lessons in leadership, hiring, and letting go of ego * How to structure a business that prioritizes people and reputation * The evolving conversation around private equity in the trades * The emotional and personal growth required to lead with authenticity This episode is a powerful reminder that building a great business starts with understanding who you are—and having the courage to grow alongside it. Links: Josh on LinkedIn - https://www.linkedin.com/in/joshzolin/ [https://www.linkedin.com/in/joshzolin/] Windy City Equipment - https://www.windycityequip.com/ [https://www.windycityequip.com/] Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/ [https://www.linkedin.com/in/sethdeutsch/] CSuite Financial Partners - https://csuitefinancialpartners.com/ [https://csuitefinancialpartners.com/] Topics: (00:00:00) - Intro (00:02:29) - Introducing Josh Zolin (00:05:57) - The Origins of Windy City Equipment (00:07:22) - From Technician to Business Leader (00:21:50) - A Family Tragedy and Transformation (00:31:51) - Expanding the Business and Writing a Book (00:35:00) - Starting a Career in Skilled Trades (00:37:52) - Lessons Learned from Expansion (00:42:33) - Building and Restructuring the Organization (00:51:23) - Navigating Financial Leadership Challenges (00:54:50) - Vision for the Future and Private Equity (01:00:43) - The Importance of Presence and Overcoming Fear (01:06:48) - Closing Remarks and Reflections

The Investrepreneur Model: Marrying Vision with Execution - Scott Silverman - Founder and CEO of Agman

In this episode of Diners & Deals, host Seth Deutsch sits down with Scott Silverman, founder and managing partner of Agman, for an in-depth look at how a multi-generational investment firm is quietly building and backing enduring companies in sectors often overlooked by traditional private equity. Scott shares his unconventional path—from earning a PhD in molecular genetics at Oxford to working at BCG and biotech venture firms, and eventually launching Agman with family capital just before the Great Financial Crisis. What started as a fund of funds has grown into a diversified investment firm with meaningful holdings in real estate, restaurants, insurance, and more. The conversation dives into: * Agman's approach to "Investrepreneurship" and backing operators from day zero * Building Ampler, a restaurant platform with 500+ units across Taco Bell, Burger King, and more * How a cold call led to Vertus, a fast-growing insurance brokerage * The creation of Omaha National and AEN Entity, two insurance companies born from within Agman * What it takes to move from passive investing to hands-on company building * Lessons in partnership, patience, and spotting long-term value Scott also reflects on the emotional realities of entrepreneurship, the power of elegant solutions, and how he balances a high-conviction investing career with life at home. Whether you're an operator, capital allocator, or founder building in a niche market, this episode offers a rare window into how real value gets created—over time, and with intention. Links: Agman [https://www.agmanpartners.com/] Scott on LinkedIn [https://www.linkedin.com/in/howard-scott-silverman-006683a5/] Seth on LinkedIn [https://www.linkedin.com/in/sethdeutsch/] Topics: (00:00:00) - Intro (00:05:51) - Being an Investrepreneur (00:07:06) - Scott's portfolio companies (00:11:15) - Scott's upbringing and influences (00:13:26) - The values of being an investor (00:14:59) - Undergrad/Graduate experiences + Early career (00:25:38) - Forming and scaling Agman (00:43:11) - How Agman is geared to help founders (00:46:12) - Building out finance and accounting teams (00:52:50) - Maintaining health and marriage alongside a career (01:01:01) - Closing thoughts