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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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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What You Learn After 40 years of Leading Through Change with T.J. Coombs - EP.274
57:23
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57:23In 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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Right to Win Series EP.2: Building Trust as Second-Time CEO with Dan Calano - EP. 273
1:11:55
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1:11:55In 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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Matt Risinger: The New Ways to Sell Building Supplies to Builders - EP.272
50:08
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50:08In 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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Right to Win Series EP.1: Patience and Persistence with Kyle Baer - EP.271
52:27
52:27
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52:27In 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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185: Decision-Making As Partners in Life & Business
24:42
24:42
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24:42Going into business with a partner, friend, or family member can be a big undertaking. In this episode of the podcast, Vincenzo and his wife, Amy Landino, discuss how to make decisions as partners in life & business.By Vincenzo Landino
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Lessons from a Decade of Growth and Acquisitions - Janelle Heuton - Co-Founder @ Heiton Partners - Ep.270
39:51
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39:51In 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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From the PGA Tour to the Trades - John Peterson - Founder of Westoplex Garage - EP.269
58:32
58:32
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58:32In 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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Richard Emery - Building Private Jet Sales Teams [Replay]
56:47
56:47
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56:47Alex (@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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Evolving Dynamics of Engine Programs with Delray Dobbins - EP.268
58:31
58:31
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58:31In 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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Governance and Family Harmony in Business (From EP.267)
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15:44Watch the full episode with Dave Whorton here - https://youtu.be/KPcgK3lm-mwBy Alex Bridgeman
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Building Evergreen Companies with Dave Whorton - EP.267
1:03:48
1:03:48
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1:03:48In 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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Henry Schuck - Creating Ambitious Teams at ZoomInfo - EP.266 [Replay]
45:03
45:03
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45:03My 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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From Episode 265 with Erika Armstrong. Watch the full video on YouTube here: https://youtu.be/Nc2vgTLhbYABy Alex Bridgeman
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A Tour of Aviation Safety with Erika Armstrong - EP.265
56:37
56:37
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56:37In 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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Rory wins the Masters & Completes the Golf Grand Slam
29:45
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29:45Sunday 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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AI Breakthroughs in the Distribution Sector (From Ep.264)
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5:02Watch the full episode here - https://youtu.be/GTxWeRXap9QBy Alex Bridgeman
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Katie Poehling Seymour - Inside a 5th Generation Distribution Giant - EP.264
1:00:34
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1:00:34In 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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Hill Hamrick on Relentless Prioritization (From Episode 263)
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14:28Watch the full episode here: https://youtu.be/UTNl0xeSgZYBy Alex Bridgeman
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Severance, Survivor & TV Show Landscape in 2025
30:23
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30:23TJ and Cupe talk about the landscape of TV in the year 2025, whether or not Severance is the best show ever, and why Survivor is TJ's all time favorite. Watch the Show on YouTube: https://www.youtube.com/@tjlaessig Follow TJ on X: https://x.com/tjlaessig Follow TJ on Instagram: https://instragram.com/tj_laessig…
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Build Series EP.6: Relentless Prioritization with Hill Hamrick - EP.263
1:05:06
1:05:06
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1:05:06In 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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Win Your March Madness Bracket Using Game Theory
36:38
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36:38March 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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Crazy Requests in Aircraft Interiors w/ Trey Bryson
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8:05From Episode 262 of Think Like an Owner. Watch the full episode here.By Alex Bridgeman
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Golf is the Greatest Leisure Sport on the Planet
42:37
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42:37Cupe 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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Running Commercial and Bizav MROs at Scale with Trey Bryson - EP.262
48:10
48:10
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48:10In 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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Integrating Jet Management and Maintenance at Davinci Jets with Eric Legvold and Trey Darr - EP.261
48:15
48:15
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48:15In 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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USA vs Canada Recap & the Great Game of Hockey
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42:14For 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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5X Airline Founder David Neeleman on Building Ambitious, Customer-Obsessed Airlines - EP.260
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54:00In 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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Talent Acquisition - From Interview to Close (From Ep.259)
17:26
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17:26Watch the full episode on YouTube: https://youtu.be/bmq6URHPLJ0By Alex Bridgeman
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Make +EV Decisions & Think Like a SHARP Gambler
40:39
40:39
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40:39TJ 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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Build Series EP.5: The Role of Talent in High Performing Teams with Jake Dancyger and Cyrus Symoom - EP.259
1:03:25
1:03:25
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1:03:25In 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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$10,000 Wins & the Early Days of Daily Fantasy Sports (DFS)
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45:19
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45:19TJ 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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High Performing Sales Highlights from Ambitious CEOs and CROs - EP.258
54:32
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54:32In 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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Poker, Fantasy Sports & Intro to Gamble: The Game of Life
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37:10
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37:10TJ 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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Introducing Gamble: The High Stakes Game of Life
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3:34
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3:34TJ 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…
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Team Management Principle & Balancing Payoffs
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9:57From Episode 257. Watcht the full episode here: https://youtu.be/x1utcQzmxjIBy Alex Bridgeman
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Build Series EP.4: Identifying and Prioritizing Value Levers with Sam Hyde & Steuart Botchford - EP.257
1:00:25
1:00:25
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1:00:25Ep.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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Cory Bengtzen on Customer Journeys and Aircraft Management in Private Aviation
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8:30From Ep.256 with Corgy Bengtzen. Get the full episode here.By Alex Bridgeman
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The Economics of Flying Private - Cory Bengtzen - Ep. 256
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44:27Ep.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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Savneet Singh on Equity Comp and Incentives
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11:18From Ep. 255 with Savneet Singh. Get the full episode here.By Alex Bridgeman
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Savneet Singh - Urgency and Culture - EP.255
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56:16Ep.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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Internal Communication Best Practices & Aligning Leadership Teams - Tim Wade
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8:06From Ep.254 of Think Like an Owner. Listen to the full episode here.By Alex Bridgeman
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Tim Wade - Ensuring Safety at FlexJet - EP.254
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40:06Ep.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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M&A Highlights from Ambitious CEOs - EP.253
1:10:25
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1:10:25Welcome 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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Savneet Singh - Leading a Public Turnaround at PAR Technology - Ep.252 [Replay]
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47:35
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47:35Ep.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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Richard Emery - Building Private Jet Sales Teams - EP.251
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58:16
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58:16Ep.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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Craig Fuller - Acquiring Flying Magazine and Building a Media Playbook - Ep.250 [Replay]
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58:16
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58:16My 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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Craig Picken - Recruiting Top Aerospace Execs - EP.249
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45:27My 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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Build Series EP.3: Profitable Growth with Kush Das - EP.248
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52:01My 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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Jim Derry - "Culture is the lowest level of behavior you'll tolerate" - EP.247
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54:40
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54:40My 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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