Think Like an Owner

Chris Hendriksen, investor at Pacific Lake Partners who builds board toolkits. Aaron Perrine, partner at Trilogy who advises on post-acquisition governance. They explore what high-performing boards feel like, how to form and evolve boards, building trust and chemistry with CEOs, practical composition and timing tips, and why feedback, executive sessions, and recruited operators matter.

Matt Kuehlhorn, founder of Cooler/Kooler Garage Doors and host of Craft Your Life radio, shares his accidental startup story and how focus transformed his company. He discusses pivoting to a single service, building systems and culture, communication frameworks for trust, and maturing leadership to enable steady, profitable growth.

Didi Azaria, founder and CEO of Workiz and former locksmith turned tech entrepreneur, built a BI company to huge ARR before creating an automation platform for trades. He talks about eliminating CRM friction, AI dispatchers that capture intake, automating scheduling/payments, turning services into subscriptions, and using strategy to filter features while boosting revenue with Workiz Genius.

Lindsey Gray, investor at Pacific Lake Partners who advises searchers on fundraising and board-building. Aaron Perrine, investor/operator at Trilogy with deep experience in evaluating searchers and post‑acquisition value creation. They discuss how to pick and narrow industry theses, what signals investors look for in searchers, signs a search is progressing, common deal pitfalls, cap table and board dynamics, and where value is created after acquisition.

Dan Antonelli, founder of KickCharge Creative and author of Branded Not Blandet, specializes in vehicle-first branding for home service companies. He explains niching into HVAC/plumbing/electrical, why brand must come before marketing, and how being “five-mile famous” cuts ad spend. The conversation highlights vehicles, mascots, color, rebranding resistance, and brand impact on recruitment and culture.

Jordan Huibers, an aviation entrepreneur and general aviation pilot, teams up with Alvin Wong, an operator and investor with a banking background, to share insights from their journey at Advanced Aircrew Academy. They delve into the challenges of their search thesis focused on aviation, the emotional strain of stepping back from a deal, and the critical importance of curiosity and relationship building in business. Their candid reflections on managing a remote team and the necessity of discipline when evaluating opportunities make for an engaging listen.

T.J. Coombs, a seasoned operator with 40 years in leadership and turnaround roles, shares valuable insights from his extensive career. He emphasizes defining success as the moment you leave, fostering accountability in transitions. T.J. advocates for spending time on the shop floor to gather practical insights and highlights the necessity of open assessments for success. He discusses the balance between strategic vision and hands-on leadership, the importance of service in the building products industry, and the role of technology in enhancing processes.

Dan Calano, a two-time search-fund entrepreneur and current CEO of Fleetflo, shares his invaluable insights on building trust and navigating the complexities of leadership. He reflects on overcoming challenges like intellectual property disputes during his acquisition of Utility Cloud and emphasizes the importance of transparency in building relationships with sellers. Dan also discusses the significance of thoughtful hiring practices, recovering from COVID-related setbacks, and how his experiences shaped a more confident and strategic approach in his second CEO role.

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 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

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, and embracing the challenges of leadership, while also diving into the practical realities of acquiring and running a company. They discuss: Kyle's career path from Accruent into Datacor and the operational experience he gained The core lessons learned at Datacor, including persistence, compounding growth, and the impact of key hires The long process of building trust with Crystal's founders and closing the acquisition The challenges of moving from operator to CEO and learning to lead through others Insights on patience, continuous improvement, and choosing the right partners and investors Follow the show on Apple Podcasts, Spotify, Google Podcasts, Stitcher, Breaker, and TuneIn. Learn more about Alex and Think Like an Owner at https://tlaopodcast.com/ Links: Kyle on LinkedIn - https://www.linkedin.com/in/kylebaer/ Crystal Practice Management - https://www.crystalpm.com/ Pacific Lake Partners Trilogy Search Partners Topics: (00:00:00) - Intro (00:05:20) - Kyle's background and career path (00:13:08) - The search fund decision (00:17:59) - The long road to acquiring Crystal (00:23:31) - Navigating the acquisition process (00:26:25) - Building relationships and support systems (00:31:06) - Challenges and learnings as a new CEO (00:42:26) - The importance of patience and continuous improvement (00:50:11) - Hiring the right people and building a strong team (00:51:24) - Final reflections and podcast conclusion