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/ Windy City Equipment - https://www.windycityequip.com/ Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/ CSuite Financial Partners - 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

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 Scott on LinkedIn Seth on LinkedIn 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  

In this episode of Diners and Deals, host Seth Deutsch sits down with Dave Rauch, founder and CEO of ProTec, a company that has spent nearly three decades redefining how homeowner associations (HOAs) approach maintenance. With over 370 employees, eight offices, and more than 1,000 communities served across Southern California and Las Vegas, Dave has built a business that fills a major gap in a largely overlooked industry. They dig into the unique operational challenges of serving HOAs, the massive opportunity in preventive maintenance, and how Dave has layered on services like plumbing, restoration, inspections, and construction to create a full-service solution. Dave also shares his long-term vision for taking ProTec national—and the systems, processes, and technology he’s investing in to scale efficiently. This episode also covers: Why preventive maintenance is the “holy grail” for HOAs The importance of coaching, mentorship, and peer learning in entrepreneurship What it takes to build a great management team and step out of daily firefighting Dave’s passion for skiing, the power of de-stressing, and staying creative as a founder How insurance and deferred maintenance are creating major risk in HOA communities nationwide Whether you’re scaling a service-based business, thinking about M&A, or curious about building something meaningful in a niche industry, this episode is packed with wisdom from a founder who’s in it for the long haul. Links: ProTec Building Services: https://www.protec.com/ Dave on LinkedIn - https://www.linkedin.com/in/jdavidrauch/ Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/   Topics: (00:00:00) - Intro (00:02:18) - Meet Dave (00:04:00) - Understanding ProTec's Business Model  (00:05:54) - Challenges and Opportunities in HOA Maintenance  (00:07:27) - The Importance of Preventive Maintenance  (00:11:31) - Navigating HOA Insurance and Legal Issues  (00:19:42) - The Founder’s Journey: From City Planning to ProTech  (00:21:45) - Financing the Business and Early Challenges  (00:22:17) - The Importance of Coaching and Mentorship  (00:22:44) - Advice for Aspiring Entrepreneurs  (00:28:32) - Building a Strong Management Team  (00:32:46) - Balancing Work and Personal Passions  (00:37:07) - Future Vision and Industry Trends  (00:42:03) - Closing Remarks and Final Thoughts 

In this episode of Diners and Deals, I sit down with Matt Schachman, Co-founder of Cold Bore Capital, for a deep dive into his journey from the military to private equity. We explore how his experiences shaped the founding of Cold Bore Capital and break down the complexities of buy-and-build strategies in the microcap space. Matt shares insights on the impact of veteran leadership, the importance of human capital, and the challenges and rewards of entrepreneurship. We also discuss what it takes to scale businesses effectively and navigate the private equity landscape. If you're interested in private equity, veteran career transitions, or the entrepreneurial mindset, this conversation is packed with valuable takeaways.   Links: Cold Bore Capital - https://coldborecapital.com/ Matt on LinkedIn - https://www.linkedin.com/in/matt-schachman-55719423/ Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/   Topics: (00:00:00) - Intro (00:02:53) - Introducing Matt (00:08:43) - Early Life and Influences (00:14:42) - Military Service and Leadership (00:18:08) - Transition to Civilian Life (00:23:27) - Entrepreneurial Leap (00:29:53) - Balancing Family and Career (00:33:21) - Balancing Entrepreneurship and Personal Life (00:34:26) - Starting a Human Capital Staffing Company (00:37:12) - Building successful partnerships (00:41:15) - The Vision for Cold Bore Capit (00:45:10) - Scaling and Operational Strategies (00:54:01) - Finance and Accounting in Private Equity (01:00:29) - Future Goals and Motivations (01:04:36) - Final Thoughts and Advice  

Steve is the CEO and Co-founder of Kelso Industries, which provides mechanical, HVAC, refrigeration, industrial, plumbing, and electrical services all throughout the United States.   Seth and Steve discuss: Seth and Steve discuss: - Early ambitions and motivations behind Kelso Industries - The importance of partnerships in executing a buy and build  - Challenges and strategies in finance management - Insights on making tough decisions and scaling through the platform build to create a sustainable m&a engine   Links: Steve on LinkedIn: https://www.linkedin.com/in/stevenhcarroll/ Seth on LinkedIn: https://www.linkedin.com/in/sethdeutsch/ Kelso Industries: https://kelso-industries.com/   Topics: (00:00:00) - Intro (00:06:27) - Kelso Industries (00:07:58) - Proving doubters wrong (00:11:38) - Steve’s early career (00:17:18) - Founding Kelso (000:29:54) - Finding the “right” acquisitions (00:39:07) - The realities of acquisition (00:49:35) - Building teams and core functions (00:58:53) - Advice to aspiring entrepreneurs

Matt Matros is one of America’s leading consumer-focused entrepreneurs, having founded and successfully exited two businesses since 2009. Matt is the founder of PROTEIN BAR & KITCHEN®, a wildly popular chain of healthy fast-casual restaurants he sold to to private equity firm L Catterton in 2013. Matt also founded LIMITLESS®, an innovative beverage company he sold to Keurig Dr Pepper in early 2020.  On this episode, Seth and Matt discuss: What it takes to be in the #1 seat in a business Experiences with Private Equity The role of a CFO in building and scaling businesses Links: Matt on LinkedIn Seth Deutsch on LinkedIn Topics: (00:00:00) - Intro (00:03:23) - Catching up with Matt (00:06:21) - Matt’s work with Edge Acquisitions (00:08:48) - What it takes to be in the #1 seat (00:13:10) - Matt’s background, career, and lessons learned (00:33:31) - Experiences with PE (01:00:40) - The role of a CFO in building and scaling businesses (01:08:50) - Closing thoughts and advice

Frank Campise is the Co-Founder and Principal of Jab Real Estate, which transforms underperforming properties in desirable urban neighborhoods into modern and efficient residences that attract young, upscale professionals.  On this episode, Seth, and Frank discuss: Building Jab Real Estate How to structure a team Looking at the future of the real estate market  Links: Jab Real Estate Frank Campise on LinkedIn Seth Deutsch on LinkedIn   Topics: (00:00:00) - Intro (00:05:44) - Frank’s background and career (00:13:45) - JAB Real Estate today (00:16:37) - How have you structured your team? (00:22:29) - What excites you about the future?    This Podcast is brought to you by CSuite Financial Partners.

Redi Lappin is the Founder & CEO of Vokal, a growth agency purpose-built to maximize value for mid-market and private-equity brands. Reid is also joined by Hery Byrne, CFO of Vokal.   On this episode, Seth, Reid, and Henry discuss: Founding Vokal and evolving the CFO role Achieving organizational alignment Organic & inorganic growth Approaches to acquisition   Links: Vokal Reid Lappin on LinkedIn Henry Byrne on LinkedIn Seth Deutsch on LinkedIn   Topics: (00:00:00) - Intro (00:04:35) - Reid on Founding Vokal (00:09:50) - Henry’s journey to becoming CFO of Vocal (00:14:08) - Evolving the CFO role (00:19:14) - Achieving alignment at every level of an organization (00:21:55) - Structuring a stock-equity program (00:29:39) - The impact of Reid’s father (00:42:03) - Tapping into mid-market PE (00:47:43) - Performative contracts (00:50:01) - Organic and inorganic growth (00:54:07) - Key industry trends (00:58:31) - Acquisition approaches (01:02:11) - Advice for founders scaling their businesses   This Podcast is brought to you by CSuite Financial Partners.

Chris Santiago is the CEO of RUI Construction. RUI provides multi-state construction services such as emergency restoration, fire reconstruction, fire and smoke damage repair, flood damage, water mitigation, structure drying, renovations, and additions. A Great Range Capital portfolio company since January 2022, the mid-market company is currently expanding nationally through de novo growth strategies and synergistic acquisition opportunities. On this episode, Seth and Chris discuss: Implementing technology into RUI Building out the CFO office Making the transition to the middle-markets & much more! Links: Chris Santiago on LinkedIn RUI Construction Seth Deutsch on LinkedIn Great Range Capital   Topics: (00:00:00) - Intro (00:03:42) - Chris’ career and company (00:06:47) - background and upbringing (00:11:39) - Making the jump from big corporate to the lower mid-market PE world (00:21:00) - Chris’ first year in the restoration business (00:27:34) - Learning the levers of the business and industry (00:30:14) - Implementing technology into the business (00:41:08) - Building out the CFO office (00:46:44) - What to look for in a business partner and CFO (00:48:41) - Predictions for the restoration industry (00:52:28) - What should folks be asking themselves if they want to make the transition that you have to the lower middle-markets?   This Podcast is brought to you by CSuite Financial Partners.

Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way. Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built. Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!