Podcast
Think Like an Owner
Hosted by Alex Bridgeman · EN
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/
21episodes
Episodes
Newest firstAll episodes
Connecting the PNW at SeaPort Airlines with Kent Craford - EP.281
Mar 3100:40:19Tap to summarizeIn this episode, Alex Bridgeman sits down with Kent Craford to unpack the evolution of SeaPort Airlines and the lessons learned from building and rebuilding a regional aviation business. Kent shares how a simple frustration with travel time between Portland and Seattle sparked the original idea, and how early missteps, capital constraints, and strategic pivots shaped the company's trajectory. The conversation explores the realities of operating in niche aviation markets, the pitfalls of government-subsidized routes, and how Kent applied hard-earned lessons from Alaska to relaunch SeaPort with a stronger foundation. Throughout, Kent offers a candid look at what it takes to build a durable transportation business in a challenging and highly operational industry. We discuss: How a commuter pain point led to the founding of SeaPort Airlines Why the Essential Air Service program often leads operators astray Lessons from scaling a regional airline in Alaska and rebuilding with better systems and capital The operational and cultural advantages of small aircraft and localized air travel What it takes to change customer behavior and build a new travel habit Links: Kent on LinkedIn - https://www.linkedin.com/in/kent-craford-2b070332/ SeaPort Airlines - https://flyseaportair.com/ Topics: (00:00:00) - Intro (00:00:51) - Kent's background and career (00:10:53) - The Essential Air Service Program (00:15:02) - Kent's experiences in Alaska (00:18:58) - Applying learnings to SeaPort in it's second iteration (00:26:27) - Customer feedback (00:30:41) - Developing route design (00:36:41) - The vision for SeaPort
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Right to Win EP.5: Better Boards with Chris Hendriksen and Aaron Perrine - EP.280
Mar 2400:50:01Tap to summarizeIn this episode, Alex Bridgeman is joined by Aaron Perrine and Chris Hendriksen to explore how boards can become a true competitive advantage for entrepreneurs. The conversation dives into the evolving role of boards within the ETA ecosystem, highlighting the growing demand for strong governance as the space expands. Drawing from recent industry discussions and their own experience, Aaron and Chris break down what separates high-performing boards from dysfunctional ones. They also share practical frameworks for building, managing, and evolving boards to better support CEOs over time. They discuss: Why board quality and CEO relationships are declining and how to fix it What a high-performing board actually feels like in practice How to think about board composition, roles, and timing during formation The importance of trust, chemistry, and engagement between CEOs and directors Why board evolution, feedback, and executive sessions are critical for long-term success Links: Boardroom Toolkit Pacific Lake Partners Trilogy Search Partners Topics: (00:00:00) - Intro (00:02:11) - Conference feedback and the state of Boards (00:07:19) - What are your goals for the next year regarding Boards? (00:12:36) - What does a well functioning board look like? (00:18:00) - How can Searchers effectively form a board? (00:25:27) - Best practices for forming a Board (00:35:34) - What are the personal reasons that you'd be excited to join a board? (00:43:20) - Recruiting new board members (00:45:57) - Closing thoughts
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Crafting your Life and Business with Matt Kuehlhorn - EP.279
Mar 1000:58:07Tap to summarizeMatt Kuehlhorn joins Alex Bridgeman to share the unconventional journey behind building Kooler Garage Doors and the lessons he has learned about focus, leadership, and craftsmanship along the way. Matt explains how a business that started almost by accident evolved into a disciplined operation centered around service, systems, and intentional growth. The conversation explores how entrepreneurs mature alongside their companies, why focus can unlock new opportunities, and how communication and leadership shape both teams and customer experiences. Matt also reflects on the personal mindset shifts required to move from chaotic growth to sustainable profitability. They discuss: • How Matt used podcasting as a networking tool to build relationships in a new market • The accidental start of Kooler Garage Doors and the early years juggling multiple service lines • Why focusing on one core service unlocked growth, better culture, and operational clarity • The difference between "old school" contractor models and a homeowner focused service business • Communication frameworks Matt teaches his team to build trust and deliver better customer outcomes Links: The Kraft Your Life Radio Show - https://www.craftyourliferadio.com/ Matt on LinkedIn - https://www.linkedin.com/in/matthewkuehlhorn/ Kooler Garage Doors - https://koolergaragedoors.com/grand-junction Topics: (00:00:00) - Intro (00:00:48) - Matt on his podcast backstory (00:03:47) - Crafting is Intention and attention (00:06:59) - Pivoting to garage doors (00:15:16) - Becoming laser-focused on one service (00:22:49) - Seasons in the life of a company (00:31:52) - V 1.0 of the company vs. today (00:38:49) - Strategic problem solving (00:40:57) - Customer service training and improvments (00:54:00) - Final thoughts
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Future of Home Services with Workiz CEO, Didi Azaria - EP.278
Feb 2400:28:56Tap to summarizeIn this episode of Think Like an Owner, Alex Bridgeman sits down with Didi Azaria to explore how firsthand experience in the trades led to building one of the leading automation platforms for home service businesses. Didi shares his journey from working as a locksmith in Los Angeles to founding a business intelligence company that scaled to hundreds of millions in ARR, and eventually launching Workiz. The conversation dives into how friction in communication, scheduling, and payments quietly kills service businesses and how AI driven automation is reshaping the industry. Didi also explains why he believes traditional CRMs should not exist and how a vision of "automate everything but the wrench" is guiding the future of home services. They discuss: Didi's path from technician to tech founder and the lessons learned from building his first company Why most leaders fail by trying to do everything and how defining your true strengths changes outcomes Eliminating CRM friction through AI dispatchers, automation, and invisible systems Turning home services into subscription style businesses with service agreements and upsells Using strategy as a filter to say no to feature requests and stay aligned with long term vision How AI driven tools like Workiz Genius are increasing revenue by improving communication and capture This episode is a must listen for operators and software founders who want to understand how automation, vision, and disciplined strategy can transform traditional service industries. Links: Workiz - https://www.workiz.com/ Didi on LinkedIn - https://www.linkedin.com/in/adiazaria/ Topics: (00:00:00) - Intro (00:00:29) - Didi's career background (00:02:57) - Pivoting from locksmithing into software (00:06:25) - What are your strongest skills? (00:07:42) - "CRMs shouldn't exist" (00:09:37) - Founding ideas behind Workiz (00:13:43) - What are ambitious home service business owners asking for from Workiz? (00:18:02) - Balancing feature requests and keeping the broader vision of the company aligned (00:19:59) - What excites you about the business for 2026? (00:23:01) - What does the organizational structure look like for home service businesses 3-5 years from now? (00:26:51) - What excites you the most for the future?
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Right to Win Series EP.4: AMA with Lindsey Gray and Aaron Perrine - EP.277
Feb 600:42:29Tap to summarizeIn the fourth episode of the show's Right to Win series, host Alex Bridgeman is joined by Aaron Perrine and Lindsey Gray for an AMA-style conversation on search, investing, and operating small businesses. Drawing on real examples from recent deals, they unpack what separates strong searches from stalled ones, how investors evaluate searchers, and where value is actually created post-acquisition. The discussion blends tactical advice with candid reflections on boards, capital structures, and the realities of building durable businesses. They discuss: How searchers can identify and narrow industry theses before and during fundraising What investors look for when evaluating searcher talent beyond resumes Signs that a search is progressing well, including compounding learning and quality seller meetings Common deal pitfalls around quality, valuation, and defensibility How boards create value for first-time CEOs and evolving companies Links: Pacific Lake Partners Trilogy Search Partners Topics: (00:00:00) - Intro (00:01:54) - Fundraising and identifying industries (00:09:43) - Evaluating searcher talent (00:13:35) - Acquisition models and strategies (00:18:30) - Cap table construction and investor relations (00:20:28) - Navigating investor relationships (00:22:12) - Signs of a successful search (00:24:28) - Key metrics for searchers (00:27:14) - Lessons from recent deals (00:30:42) - Building an effective board (00:35:00) - Creating value in acquisitions (00:38:15) - Desert island CEO picks (00:39:48) - Sports rivalries and fun bets (00:41:45) - Conclusion and farewell
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Building Trusted Brands with Dan Antonelli of Kickcharge Creative - EP.276
Jan 2901:09:40Tap to summarizeIn this episode of Think Like an Owner, Alex Bridgeman sits down with Dan Antonelli to unpack why branding is the foundation of sustainable growth for home service businesses. Dan shares the long arc of building his firm through specialization, the discipline of saying no to the wrong work, and how focusing on being "five-mile famous" can dramatically reduce reliance on paid advertising. The conversation explores how brand decisions influence not just marketing efficiency, but recruitment, culture, and long-term enterprise value. We discuss: Why niching into home services unlocked scale, profitability, and clarity The difference between branding, marketing, and advertising and why brand must come first How strong brands lower customer acquisition costs over time The role of vehicles, mascots, color, and design in creating memorability Why internal culture and recruiting are deeply shaped by brand choices This episode is a must-listen for operators and founders who want to build a brand that drives growth, loyalty, and lasting competitive advantage. Links: KickCharge Creative - https://www.kickcharge.com/ Dan on LinkedIn - https://www.linkedin.com/in/danantonelli/ Topics: (00:00:00) - Intro (00:00:37) - Finding your niche in business (00:04:16) - The importance of branding in home services (00:05:32) - Making data-driven decisions (00:07:51) - Challenges and rewards of specialization (00:09:00) - The value of saying no (00:13:53) - Building brands that change lives (00:27:50) - The impact of branding on recruitment (00:32:30) - The power of a strong brand story (00:35:16) - Effective use of vehicles in branding (00:37:02) - The decline of phone numbers and QR codes (00:41:08) - The role of mascot branding (00:45:17) - The power of color in branding (00:53:36) - Retro vs. modern branding (01:01:49) - Customer experience and brand authenticity (01:07:31) - Final thoughts and recommendations
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Right to Win EP.3: Learning to Fly with Jordan Huibers and Alvin Wong - EP.275
Dec 200:41:38Tap to summarizeAlex Bridgeman is joined by Alvin Wong and Jordan Huibers on Think Like an Owner, exploring their long-standing partnership, the focused search that led them to Advanced Aircrew Academy, and the lessons they've carried into running the company. They walk through the origins of their collaboration, how a shared passion for aviation shaped their search thesis, and the discipline required to pursue only the opportunities that truly aligned with their experience and values. They also reflect on the emotional highs and lows of stepping away from a business they loved, only to return months later with deeper conviction and ultimately close the acquisition. Their discussion highlights themes of curiosity, humility, relationship building, and maniacal focus as tools that helped them through both the search and their first year as CEOs. They discuss: • How Alvin and Jordan developed their industry-focused search thesis and complementary roles within it • The emotional and practical challenges of walking away from an LOI and what ultimately brought them back • Lessons from navigating remote-team dynamics during their first year of ownership • The importance of curiosity, people-orientation, and focus as competitive advantages • Guidance for future searchers on prioritizing effectiveness over efficiency Links: Advanced Aircrew Academy - https://www.aircrewacademy.com/ Alvin on LinkedIn - https://www.linkedin.com/in/alvinwongto/ Jordan on LinkedIn - https://www.linkedin.com/in/jordanhuibers/ Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/ Topics: (00:00:00) - Intro (00:04:55) - The origin of Alvin and Jordan's relationship (00:08:16) - The Search and circling in on an industry focus (00:23:15) - The first few months on the ground post-close (00:30:47) - How the Search community helped Alvin and Jordan (00:33:46) - Taking a people-oriented approach to the business (00:36:51) - Advice for the listeners
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What You Learn After 40 years of Leading Through Change with T.J. Coombs - EP.274
Oct 2800:57:23Tap to summarizeIn 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 strong leadership teams. He discusses his philosophy of defining success by when you leave, the importance of disciplined assessments, and the hands-on approach required to truly understand and improve a business. They discuss: • How defining success as "when you leave" creates accountability in leadership transitions • Why the best business insights often come from the shop floor, not the boardroom • The mindset and structure required to execute successful turnarounds • How effective CEOs balance strategic vision with time spent in the field • The future of the building products industry and the growing importance of service and technology Links: T.J. on LinkedIn - https://www.linkedin.com/in/tjcoombs/ Topics: (00:00:00) - Intro (00:01:48) - The drive to lead (00:05:12) - When you know you're work is done (00:07:04) - Evaluating WHO you want to work with (00:12:17) - "Staple yourself to an order" (00:15:46) - Favorite questions to ask in order to better understand a business (00:18:08) - How long do you typically spend as an interim CEO? (00:20:06) - Involvement in hiring the permanent CEO (00:23:13) - Leading a turnaround business (00:31:00) - The key jobs of a CEO (00:42:56) - The state of the Distribution and Install industries (00:54:41) - Advice to building supply leaders
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Right to Win Series EP.2: Building Trust as Second-Time CEO with Dan Calano - EP. 273
Oct 2101:11:55Tap to summarizeIn 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 concentration, and how trust, discipline, and process shaped his leadership. He then shares what it was like to sell the company, transition through an acquisition, and ultimately launch Grouper Companies and acquire Fleetflo for his second CEO chapter. They discuss: • Building trust with sellers through transparency, follow-through, and "show me" actions • The importance of hiring slowly, managing talent thoughtfully, and reducing organizational friction • Navigating customer concentration risk and recovering from COVID-era setbacks • The decision-making and emotional process behind selling a company • How Dan approached his second search and CEO role differently, focusing on autonomy, community, and process-driven risk-taking Links: Dan on LinkedIn - https://www.linkedin.com/in/dcalano/ Fleetflo - https://fleetflo.com/index.html Pacific Lake Partners Trilogy Search Partners (00:00:00) - Intro (00:04:27) - Dan's background and career (00:10:03) - Building trust and overcoming challenges (00:23:19) - Navigating talent and reducing friction (00:33:01) - Deciding to sell Utility Cloud (00:37:51) - Reflecting on team and autonomy (00:40:23) - Post-acquisition role and insights (00:44:21) - Starting Grouper Companies (00:45:32) - Autonomy and community (00:50:36) - Second-time search and CEO experience (01:04:59) - Approach to risk and decision making (01:11:06) - Conclusion and final thoughts
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Matt Risinger: The New Ways to Sell Building Supplies to Builders - EP.272
Oct 1500:50:08Tap to summarizeIn 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 transformed his business and his approach to education within the trades. The conversation explores how trust, service, and transparency remain the cornerstones of effective supplier relationships, even as digital tools and AI change how materials are ordered and managed. They discuss: • How Matt built Risinger Build and transformed his blog into a thriving media company through YouTube • Why builder-supplier relationships depend on service and reliability over price • How purchasing groups helped small builders gain better pricing and leverage • The impact of new digital platforms on takeoffs and pricing transparency • The role of content in shaping homeowner expectations and industry standards through Build Show Network and the upcoming Build HD Standard Links: Build Show Network - https://buildshownetwork.com/ Risinger Build - https://www.risingerbuild.com/ Build Show on YouTube - https://www.youtube.com/mattrisinger Topics: (00:00:00) - Intro (00:01:26) - Matt's journey: From builder to YouTube star (00:07:33) - The birth of The Build Show (00:13:06) - The importance of customer service in building (00:19:58) - Changes in the building supply industry (00:26:15) - The future of semi-custom home building (00:28:42) - Challenges in window and door sales (00:33:10) - The importance of detailed orders and communication (00:37:44) - The role of content in builder-supplier relationships (00:40:18) - Introducing the Build HD standard (00:45:45) - Upcoming events and reflections on the industry
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