How Rollo Insurance 5X'd in 5 Years Without a Niche or Outside Capital

How Scott Tannas Turned One Small-Town Agency into a $775M Exit

Host Callan Harrington sits down with Scott Tannas, Chairman of Western Investment Company and Canadian Senator, to explore how he transformed a single small-town insurance agency into a massive enterprise. Scott shares the remarkable journey of growing Western Financial Group's stock price by 1038 percent, ultimately leading to a $775 million acquisition in 2017. Scott walks through his methodical approach to acquiring insurance agencies across small-town Western Canada, starting with just $100,000 and a willingness to learn the business from the ground up. He discusses the critical moments when he had to systematize operations, rebrand individual agencies under one unified name, and build a cohesive culture across 140 distributed locations. From implementing employee conventions and boot camps to developing guiding principles that attracted the right people while repelling the wrong ones, Scott demonstrates how intentional culture-building scaled across hundreds of employees in dozens of communities. This conversation offers invaluable insights for anyone looking to scale an insurance brokerage through strategic acquisitions while maintaining culture and operational excellence. Key topics covered: [00:00] Intro [03:42] Acquiring High River Insurance with $100,000 [05:49] Early Growth Strategy and Phone Book Prospecting [07:33] Spotting Opportunities at Broker Conventions [08:38] Going Public with Junior Capital Pool [10:47] Small Town Focus Over Metropolitan Markets [12:26] Thoughtful Targeting and Relationship Building [16:54] Building Culture Across Distributed Workforce [18:52] Slaying Sacred Cows at 25 Stores [21:34] Employee Conventions and Boot Camp Training [24:58] Creating Real Guiding Principles [29:27] Single Number Focus and Flash Reports [31:12] Paying Branch Managers Like Mini Owners [33:57] Leading Through Different Growth Stages [35:32] Becoming the Brand at 50 Employees [38:45] Starting Western Investment Company [40:33] Building Fortress Insurance and Finding Partners [42:17] Vision for Specialty Insurance Constellation Connect with Scott Tannas on LinkedIn: https://ca.linkedin.com/in/scotttannas Subscribe to The Insurance Growth Lab for more tactical insights from insurance industry leaders who are driving real growth results.

Chad King's M&A Strategy That Grew King Risk Partners to $125 Million

Host Callan Harrington sits down with Chad King, Chairman and Founder of King Risk Partners, to explore how he transformed a 6-person family agency into a $125 million powerhouse with over 600 employees. Chad shares the pivotal lesson from his father about keeping your word that became the foundation of his business philosophy, from driving through hurricanes to close deals to building authentic relationships that differentiate King in the competitive M&A landscape. Chad reveals his unconventional early acquisition strategy where agencies with websites were considered too big to buy, leading to creative deal structures and genuine connections with sellers. He discusses the evolution from hands-on operator to visionary leader, the importance of finding patriots over mercenaries in partnerships, and how maintaining personal relationships at scale has driven King's growth to over 60 acquisitions.  Chad's story demonstrates how authentic leadership and genuine care for people can build extraordinary business results while maintaining strong company culture. Key topics covered: [00:00] Intro [01:06] Dad's lesson about keeping your word [03:17] Driving through hurricanes for M&A deals [06:16] Leaving Wall Street for family insurance agency [09:13] First acquisition strategy targeting agencies without websites [12:16] Creative deal structures for early acquisitions [15:02] Choosing the right private equity partner [18:51] Building emotional connections in M&A deals [22:02] Maintaining personal relationships at scale [26:22] Patriots vs mercenaries approach to acquisitions [28:48] Providing confidence through transparency and testimonials [32:38] Evolving leadership through different growth stages [36:33] Finding your zone of genius in M&A [39:41] Building with humility and asking for help [40:46] Long-term vision for company culture Connect with Chad King: https://www.linkedin.com/in/malcolm-chad-king-509a1812 Subscribe to The Insurance Growth Lab for more tactical insights from top insurance industry leaders, and don't forget to leave a review if this episode was valuable to you.

How Rollo Insurance 5X'd in 5 Years Without a Niche or Outside Capital

Callan Harrington sits down with Jackson Rollo, President of Rollo Insurance, to explore how he became president at 24 and led the agency through 5x growth over 5 years without private equity backing. Jackson explains Rollo's unique philosophy of being a local generalist rather than pursuing industry niches, focusing on relationships and community connections over product specialization. He details their systematic approach to scaling culture across 250 teammates in 50 locations nationwide, including the creation of the Rollo Rules and integration processes for acquisitions. The conversation covers practical strategies for driving cultural adoption remotely and how they maintain their family business values while achieving venture-backed growth rates. Discover how relationship-first thinking and local community focus can drive exceptional growth in the insurance industry. Key topics covered: [00:00] Intro [02:17] Top producer credibility drives leadership success [04:02] Converting sales expertise into teachable processes [07:59] Local generalist strategy over niche specialization [11:03] Building trust through personal connections [13:27] Scaling local relationships across multiple states [17:12] Culture integration for new acquisitions [22:28] Handling cultural misalignment in acquisitions [25:59] Defining culture through beliefs values standards [29:26] Driving adoption of Rollo Rules nationwide [33:53] Right people doing right way growth formula [38:13] Learning from mistakes with mentorship guidance [40:20] 10 year vision staying true to core values Connect with Jackson Rollo: https://www.linkedin.com/in/jacksonrollo Subscribe to The Insurance Growth Lab for more tactical insights from top insurance industry leaders, and don't forget to leave a review if this episode was valuable to you.

How Brokers Can Become True Risk Advisors with Aclaimant President David Wald

Callan Harrington sits down with David Wald, President and Co-Founder of Aclaimant, to explore what it truly means to become a risk advisor in today's insurance market. David shares the unexpected origin story of Aclaimant and its growth trajectory to tracking billions of dollars in claims annually and serving thousands of companies. The conversation dives into the practical aspects of becoming a true risk advisor rather than just a rate-shopping broker. David outlines the three key components that separate real risk advisors from those who just talk about it. He also shares his insights on the importance of leveraging professional networks, the transition from founder to president, and why listening to industry veterans can accelerate business growth. This episode provides actionable insights for brokers looking to evolve their service model and technology entrepreneurs entering the insurance space. Key topics covered: [00:00] Intro [01:01] Father-in-law's app idea sparks startup [04:11] Three early customers say yes immediately [07:58] What being a risk advisor really means [11:00] Quarter million premium threshold for advisory services [12:32] Three parts of successful risk advisory [17:54] Geographic density versus vertical specialization [22:46] Leveraging asymmetric relationship advantages [25:48] Network building creates business opportunities [30:34] Hiring Kathy Burns as CEO transition [34:47] Organizational maturity through experienced leadership [37:33] Listen more to industry wisdom Connect with David Wald on LinkedIn: https://www.linkedin.com/in/davidawald Subscribe for more tactical insurance growth insights and strategies from industry leaders who are driving real results.

Chris Paradiso's Retention System Every Insurance Agency Needs

Host Callan Harrington sits down with Chris Paradiso, owner of Paradiso Financial and Insurance Services, to dive into the retention strategies that form the foundation of real agency growth. Chris shares how his 50+ employee agency learned the hard way that retention is everything when their numbers dropped nearly 10% after getting lazy with client communication during COVID. Chris breaks down his systematic approach to client retention, from the 60-day renewal process to the three-attempt phone call strategy for top clients. The conversation covers practical tactics like same-call resolution, Net Promoter Score follow-ups, and why Chris believes emails are for information but phone calls are for communication. This episode delivers actionable insights for any agency owner looking to build sustainable growth through stronger client relationships and proven retention systems. Key topics covered: [00:00] Intro [01:00] Marine Corps Boot Camp Experience [03:46] Conquering Fear Through Challenges [07:37] Real Growth Starts with Retention [08:15] Vegas Agency Retention Disaster [10:45] Phone Calls Drive Retention Success [13:53] Calling Every Single Client [18:14] Single A Clients Become Triple A's [20:30] Growth Formula with Retention Math [21:00] Soft Market Premium Challenges [23:55] Coverage First Price Second Strategy [26:02] Recording and Auditing Phone Calls [28:44] Segmented Client Touch Points [30:21] 60 Day Renewal Process [32:17] Net Promoter Score Follow Up [34:01] Dunkin Donuts Gift Card Hack [37:36] Same Call Resolution Strategy [39:17] First Step Retention Coaching Advice [41:40] Investing in the Best Training Connect with Chris Paradiso on LinkedIn: https://www.linkedin.com/in/christopherparadiso Subscribe to The Insurance Growth Lab for more tactical growth strategies from industry leaders.