Think Like an Owner

In 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

In 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

Matt 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

In 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?

In 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