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TJ Laessig is a former corporate grinder turned entrepreneur, with a long history of winning at gambling games from poker, to fantasy sports, to business. Cupe is TJ’s best friend and partner in crime for the past 15 years, along for the ride every step of the way. Tune in to this podcast series for risk / reward strategies, untold stories, and hot takes on all things sports, gambling, and entrepreneurship. Follow along as TJ & Cupe navigate their way through the highest stakes game you can ...
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Think Like an Owner

Alex Bridgeman

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Exploring how the most ambitious CEOs grow great companies. Each week we dive into the strategies and tactics that build transformative businesses with the operators doing it firsthand. Learn more at https://tlaopodcast.com/
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The Vincenzo Landino Show offers concise insights into business, content, and the pursuit of excellence. No fluff, just ideas worth putting into play. For the ambitious creators and leaders who want influence that converts while living their best life.
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In this episode of Think Like an Owner, Alex Bridgeman sits down with T.J. Coombs, an experienced operator and turnaround expert with decades of leadership across industries including building products, manufacturing, and distribution. T.J. shares lessons from his 40-year career helping companies navigate transitions, execute turnarounds, and build…
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In this second installment of the Right to Win series on Think Like an Owner, host Alex Bridgeman sits down with Dan Calano to unpack the lessons learned from his journey as a two-time search fund entrepreneur. Dan reflects on his first acquisition of Utility Cloud, navigating challenges like intellectual property disputes and customer concentratio…
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In this episode of Think Like an Owner, Alex Bridgeman sits down with homebuilder and content creator Matt Risinger to discuss how the builder-supplier relationship is evolving and how technology is reshaping the construction industry. Matt shares the story of founding Risinger Build and Build Show Network, detailing how content creation transforme…
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In this episode, Alex Bridgeman sits down with Kyle Baer to reflect on his journey from Accruent to Datacor and now leading Crystal. Kyle shares the lessons he learned sourcing acquisitions, scaling a software business, and ultimately transitioning into his first CEO role. Their conversation highlights the importance of patience, building trust, an…
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In this episode, Alex Bridgeman talks with Janelle Heuton about her decade-long journey helping transform a small GIS company into a scaled software business serving local governments nationwide. Janelle shares how she joined GIS Workshop by chance, quickly rose to COO, and partnered with CEO Joe Heieck to drive strategic change, including shifting…
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In this episode of Think Like an Owner, host Alex Bridgeman sits down with John Peterson for a wide-ranging conversation on entrepreneurship, adaptability, and building a service business from the ground up. John traces his path from professional golf—where he saw firsthand the parallels between sports and entrepreneurship—to flipping houses during…
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Alex (@Aebridgeman) is joined by Richard Emery (@Richardemery2). In this episode, my guest is Richard Emery, who has held various notable positions in business aviation sales at brands like Canadair, Bombardier, Gulfstream, and Hawker Beechcraft. Richard shares his experiences in different sales cultures, managing high-performing teams, and partici…
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In this episode of Think Like an Owner, I sit down with Delray Dobbins, Director of Sales at Engine Assurance Program (EAP), to dive into one of the most overlooked yet essential components of business aviation: jet engine maintenance programs. With a career spanning Rolls-Royce, Pratt & Whitney, and now EAP, Delray brings a deep and practical pers…
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In this episode of Think Like an Owner, I sit down with Dave Whorton, founder of Tugboat Institute and author of Another Way, to explore a different path for entrepreneurs—one built on permanence, purpose, and long-term thinking. After an early career in venture capital and tech startups, Dave walked away from the high-growth, high-exit model to fo…
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My guest today is Henry Schuck, founder and CEO at ZoomInfo, one of the most successful data businesses in recent times with a market cap today around $12B. I've been looking forward to this podcast for a long time because Henry has proven to be an effective founder, acquirer, and public CEO capital allocator, which is a rare combination of skills …
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In this episode of Think Like an Owner, I sit down with Erika Armstrong, a pilot, author, and aviation expert whose career has taken her from corporate jets to major airlines to the university classroom. Erika shares stories from her early days in aviation, from sleeping on crash pads with seven other pilots to flying charter flights into some of t…
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Sunday was one of the most epic Master's finishes of all time, with Rory McIlroy defeating Justin Rose in a playoff. TJ and Cupe break down this historic win, share their viewing experiences, and discuss the state of professional golf as a whole. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig Follow TJ on X: https://x.com/tjlaessig F…
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In this episode of Think Like an Owner, I sit down with Kathryn Poehling Seymour, President and CEO of First Supply, a fifth-generation, family-owned distribution business with over 700 employees and 53 locations across the Midwest. We cover everything from leading a 128-year-old company through generational transition to building one of the larges…
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In this episode of Think Like an Owner, I sit down with Hill Hamrick, Co-CEO of Central Storage & Warehouse, to explore how he and his team run a complex, high-volume cold storage business that ships hundreds of millions of frozen food products across North America every year. We dive into how Hill and his co-CEO, Sam, transitioned from first-time …
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March has arrived, which means one thing - college basketball will be taking over our TVs! On this episode, TJ and Cupe discuss how you can use the principles of Game Theory to win your March Madness bracket. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig Follow TJ on X: https://x.com/tjlaessig Follow TJ on Instagram: https://instrag…
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Cupe and TJ talk all things golf including their reasoning for why golf is one of the best sports in the world. They cover their golf history and why golf has EXPLODED in popularity over the last 10 years. Hint: Netflix and YouTube have a lot to do with it. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig Follow TJ on X: https://x.com/…
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In this episode of Think Like an Owner, I sit down with Trey Bryson, an aviation industry veteran with deep experience across business aviation, commercial MRO, and aircraft completions. Trey shares how his career has spanned everything from customizing luxury VIP jets—including designing in-air hot tubs and modular gyms—to founding Jet Works, an i…
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Poker is the OG skill gambling game. On this episode, TJ and Cupe talk through their journeys in the game of poker, the evolution of poker study over the years, and the poker retreat TJ attended last November. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig Follow TJ on X: https://x.com/tjlaessig Follow TJ on Instagram: https://instra…
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In this episode of Think Like an Owner, I sit down with Eric Legvold and Trey Darr of Davinci Jets to explore the business of private aviation management and MRO (Maintenance, Repair, and Overhaul) services. We dive into how Davinci Jets was built from the ground up, the evolution of private jet management, and why the company has remained profitab…
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For a brief moment last week, hockey took the sports world by storm with the 4 Nations tournament, culminating in the USA vs Canada championship game. On this episode of Gamble, TJ and Cupe break down their past experiences with hockey, discuss the success of the 4 Nations tournament, and talk about the future of hockey, its potential to increase i…
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In this episode of Think Like an Owner, I sit down with David Neeleman, one of the most accomplished entrepreneurs in aviation history. With a track record that includes founding five airlines—Morris Air (sold to Southwest), WestJet, JetBlue, Azul, and now Breeze Airways—David has built transformative companies across three different countries and …
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TJ and Cupe break down one of the key terms in the gambling space - Expected Value. TJ explains the concept of EV, shares examples of EV across games like poker, fantasy sports, and NBA Top Shot - and even discusses how you can apply this decision-making framework in your everyday life. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig …
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In this episode of Think Like an Owner, we're tackling one of the most critical elements of scaling a business—building a world-class talent engine. Joining me are Jake Dancyger and Cyrus Symoom, co-CEOs of Clariti, who have spent the last five years growing their company from 20 employees to over 120. We break down the entire talent lifecycle, fro…
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TJ and Cupe travel back in time to 2012-2017, the early days of Daily Fantasy Sports (DFS). They reflect on the landscape of the games at that point in time, share stories of their first $10,000 wins, and discuss the value of being early to new game types, and how you can identify these types of opportunities for yourself. Watch the Show on YouTube…
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In this episode of Think Like an Owner, I'm diving into one of the most crucial aspects of scaling a business—building and optimizing high-performing sales teams. To bring you the best insights, I've pulled together wisdom from past conversations with some of the sharpest minds in the game, including Tim Strickland, Mahesh Rajasekharan, Michael Cos…
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TJ and Cupe premier the first episode of a new podcast, Gamble : The High Stakes Game of Life. The show will cover TJ's life journey and a decades worth of highs and lows in poker, fantasy sports, entrepreneurship, and more with color commentary from side-kick Cupe. On Episode 1, they provide an introduction to the podcast series as a whole, dive i…
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TJ Laessig is a former corporate grinder turned entrepreneur, with a long history of winning at gambling games from poker, to fantasy sports, to business. Cupe is TJ’s best friend and partner in crime for the past 15 years, along for the ride every step of the way. Tune in to this new podcast series for risk / reward strategies, untold stories, and…
  continue reading
 
Ep.257: Alex (@aebridgeman) is joined by Steuart Botchford (@Botchford) and Sam Hyde. In this episode, I sit down with Sam Hyde and Steuart Botchford to dive into their journey of acquiring and growing Northstar Fertility, a leading surrogacy and egg donation agency. Sam and Steuart share their insights from building and managing the business, incl…
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Ep.256: Alex (@aebridgeman) is joined by Cory Bengtzen (@Cory-Bengtzen). In this episode, I sit down with Cory Bengtzen, founder and CEO of SkyShare, to explore his entrepreneurial journey from the auto industry to building a vertically integrated private aviation business. Cory shares how his passion for aviation inspired him to leave the car busi…
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Ep.255: Alex (@aebridgeman) is joined by Savneet Singh (@SavneetS). In this episode, I sit down with Savneet Singh, CEO of PAR Technology, to explore the interplay between urgency, culture, and leadership in building a successful public company. We discuss how Savneet has embedded a sense of urgency as a core value at PAR and how it drives decision…
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Ep.254: Alex (@aebridgeman) is joined by Tim Wade (@Twade889). In this interview, we dive deep into safety in the aviation industry with Tim, the Director of Environmental Health and Safety at FlexJet. We discuss the current safety landscape, Tim's role, and the importance of a Safety Management System (SMS). The conversation highlights the transit…
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Welcome to a special holiday episode of Think Like an Owner! For this unique experiment, we've compiled highlights, concepts, and invaluable ideas from some of our most popular episodes, creating a "mega episode" filled with wisdom from multiple accomplished guests. The focus? M&A (Mergers and Acquisitions)—a topic that captivated our audience thro…
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Ep.252: Alex (@aebridgeman) is joined by Savneet Singh (@SavneetS). My guest today is Savneet Signh, CEO of PAR Technology, a billion-dollar market cap publicly traded point of sale software business serving the restaurant industry. I've been following Savneet's career since college when he went on Invest Like the Best talking about acquiring softw…
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Ep.251: Alex (@Aebridgeman) is joined by Richard Emery (@Richardemery2). In this episode, my guest is Richard Emery, who has held various notable positions in business aviation sales at brands like Canadair, Bombardier, Gulfstream, and Hawker Beechcraft. Richard shares his experiences in different sales cultures, managing high-performing teams, and…
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My guest on this episode is Craig Fuller. Craig is the founder of FreightWaves, a data and media business focused on freight and supply chains. FreightWaves is a VC backed company with $19 million in revenue with editorial content, a data product, job board, video content, and multiple podcasts. Prior to FreightWaves, Craig had no background in med…
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My guest on this episode is Craig Picken, an executive recruiter for C-suite executives in the aviation industry. We discuss key trends in aviation recruiting, top firms' strategies to attract and retain talent, and how small companies can have recruiting advantages over larger competitors. We also touch on the importance of having an external-faci…
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My guest for this third episode in our Build Series is Kush Das, CEO of Ennoble Care, to talk about profitable growth. Or as he calls it, sustainable growth; something that goes to the heart of his mission to serve patients with the best possible care alongside a disciplined and motivated team. Kush and I discuss how they measure return on investme…
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My guest on this podcast episode is Jim Derry, the CEO of Field Fastener, a $180 million fastener business based in the Midwest with a unique vendor-managed inventory system. We discuss two main topics: culture and maintaining a multi-generational family business. Jim shares insights on creating a measurable, data-driven culture where talented peop…
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