Main Topics Summary:

0:53: Entering actuarial science

During his senior year of college, Alex was deciding between teaching, grad school, and actuarial science. Taking an early actuarial exam led him to begin his career at ISO, despite actuarial science not being a common path at MIT.

5:02: Early career and AIG

Alex discusses his early years at ISO, where he built technical skills and progressed through the actuarial exams. He then reflects on his brief but memorable time at AIG during the 2008 financial crisis.

8:26: Wisconsin roles and leadership growth

After moving to Wisconsin, Alex joined CUNA Mutual Group and later American Family. These roles gave him deeper experience in commercial lines pricing.

14:00: Joining C&F and becoming Chief Actuary

Alex explains that C&F was a company he had long wanted to join and that he came aboard in 2018; becoming Chief Actuary in 2020.

18:01: Decentralization at C&F

Marc and Alex discuss decentralization as one of the biggest changes at C&F during Alex’s tenure. They describe how it improved accountability, gave divisions more ownership over decisions, and strengthened the role of embedded actuarial support within the business units.

23:48: Reserve discipline and communication

Alex notes that C&F has become better at saying no to business that does not fit, and Marc connects that to stronger accountability and reserve discipline. They also discuss Alex’s writing in the President’s Report and the importance of explaining technical actuarial concepts clearly to a broad audience.

29:14: Actuarial vs. data science

The discussion turns to career paths and whether actuarial science or data science is the better choice for quantitatively minded professionals. Alex believes that the future is not one versus the other, but a combination of the two.

38:54: Soft markets, modeling, and AI

Alex talks about C&F’s strong reserve position and previews work on how modeling can help navigate a soft market. He and Marc also discuss AI as a force multiplier that can enhance actuarial work.

46:12: Future of the profession

Alex predicts that actuaries will increasingly move into broader leadership roles across the business. He ends on an optimistic note about the actuarial profession and the professional opportunities available at C&F.

1:54: An Unplanned Path to Insurance

From accounting at Liberty Mutual to practicing law and joining AIG, Mike's financial background unexpectedly helped shape his insurance career.

8:45: Building a Career Beyond the Courtroom

The conversation explores the realities of legal practice, the business skills attorneys need to succeed, and Mike's transition from litigation to transactional insurance work.

14:00: Corporate Legal as the Company's Goalkeeper

A look at the many responsibilities of Corporate Legal, from regulatory compliance and governance to contracts, policy development, and business risk management.

19:08: Managing Transactions and Deals

An inside look at how Corporate Legal manages transactions, works with Fairfax on major acquisitions, and leverages outside counsel when specialized expertise is needed.

22:48: Why Company Policies Matter

Company policies serve as both a resource for employees and a safeguard for the business — acting as both a sword and shield. This means that awareness, compliance, and early reporting are essential for success.

27:13: Navigating the Regulatory Landscape

The discussion turns to the challenges of operating in a highly-regulated industry and the importance of relationships with regulators across the country.

33:46: The Role of Trade Associations

Trade groups like APCIA help insurers monitor legislation, influence policy discussions, and stay ahead of emerging regulatory issues.

41:45: Improving the Industry's Reputation

Insurance affordability, public perception, and industry advocacy take center stage as the conversation examines how insurers communicate their value to consumers.

48:29: Legal as a Business Partner

The episode closes with a reminder that Corporate Legal is a business partner, helping teams navigate challenges and achieve their goals.

Flipping the Script: Friday Check-In Deep Dive episodes feature employees taking a closer look at topics from Marc’s Weekly Check-Ins, asking follow-up questions and gaining deeper insight into his perspective on the issues that matter most.

Main Topics Summary:

01:12: Andy’s path into surety

Andy describes how he entered surety through networking after majoring in economics. Marc and Andy reflect on how people often “fall into” insurance and surety from versatile academic backgrounds.

03:54: C&F growth and Fairfax

Andy asks about Marc’s Check-In #311, which noted that C&F’s Q4 growth outpaced the rest of Fairfax combined. Marc explains that C&F’s diversified business mix is similar to Fairfax’s approach – the diversity smooths the natural seasonality and cyclical nature of the industry.

08:21: C&F’s standing within Fairfax

Andy asks the perception of C&F in Fairfax’s eyes today. Marc says C&F is still sometimes viewed through an outdated lens, and sees storytelling as important to changing that perception, including his book, The Once and Future C&F.

10:32: Fairfax share buybacks

Andy raises Fairfax’s share buyback strategy and asks why repurchasing shares above book value can still make sense.

18:42: Long-term leadership mindset

Andy asks how long-term thinking influences Marc’s daily decision-making as CEO. Marc says it shapes how he develops people, manages the business, and avoids short-term decisions.

25:55: Career growth and culture

Marc expands on how leaders must shift from focusing on themselves to thinking about the company and its people with a long-term view.

27:11: Brand Ambassador program and C&F culture

When asked about the C&F Brand Ambassador Program, Andy says it has helped raise C&F’s visibility externally while connecting employees internally. Andy links C&F’s strong culture to leadership focus and employee-centered initiatives.

29:00: Hybrid work and local presence

Marc and Andy discuss how hybrid work functions in Surety, where in-person producer and agent relationships still matter.

31:49: C&F’s Future

Andy closes by stressing that C&F’s culture is a major differentiator, especially compared with other workplaces.

00:47: Alex's Path into Insurance

Alex explains that he originally expected to become a math teacher or professor. His path changed when he discovered actuarial science in college, and began building a career in insurance from there.

3:25: Building a Prediction Market with AI

Marc and Alex explore how an internal prediction market could become both fun and operationally useful. They also discuss needed improvements, such as bet-closing rules, admin controls, broader participation, and guardrails around insider knowledge. Visit C&F Signal to learn more.

12:20: AI Experimentation in Daily Work

Alex describes how his team uses AI to handle time-consuming analytical tasks. He emphasizes that these tools can save substantial time, but still require human review and validation to catch errors.

14:51: Industry AI Momentum and C&F's Positioning

Marc notes that C&F’s bubble-up innovation seems to be keeping us on pace with the industry.

16:13: Silver Platter and Underwriting Support

Alex outlines the Commercial Lines initiative called Silver Platter, which aims to surface key underwriting and claims insights more efficiently. The goal is to reduce administrative burden to focus more on judgment and decision-making.

18:43: Deterministic systems vs evolving AI Insights

Marc raises the challenge of consistency in AI-driven underwriting, especially when models can produce changing answers over time.

20:49: Growth Through More Underwriting Capacity

Alex explains that by reducing the time spent on document review, comparisons, and administrative analysis, underwriters could potentially quote significantly more business with the same resources.

22:46: Claims and Service Efficiency

Marc extends the AI discussion to claims and customer service, describing how AI can prepare information in advance so employees can respond faster and more effectively.

24:41: Innovation Day as a Team Practice

Alex explains how his team’s quarterly Innovation Day has evolved into a forum for experimentation, sharing ideas, and learning what new tools make possible.

28:01: Insurance in 2035

Alex shares his view that the future of insurance will depend heavily on how well companies capture and structure institutional knowledge, documentation, and context for AI-assisted decision-making.

34:49: Future Distribution and Quoting Dynamics

Alex notes that both carriers and producers are building more automation, which could lead to faster, more direct quote requests. They recognize that long-standing distribution relationships will still matter.

37:48: Encouraging Employees to Explore Better Tools

Alex closes by encouraging employees to reach out if they have repetitive or labor-intensive processes that may be improved through automation or AI.

Here’s a summary of what Marc and Michael discuss:

00:46: Michael’s Path to Insurance

Michael shares how he moved from banking to C&F and now supports Commercial Lines through data and analytics.

02:32: MarcBot

Marc and Michael briefly discuss how Michael used MarcBot to shape interview questions, with both highlighting its practicality and helpfulness.

02:49: Making Sense of Big Numbers

Referencing Check-In #300, Michael and Marc discuss how examples like SpaceX, AI data centers, and billion-dollar claims can distort perspective when massive numbers become normalized and influence decision-making.

9:14: The Compounding Impact of Insurance Trends

Marc explains how compounding trends and soft-market rate expectations can erode insurance profitability over time.

12:44: Float Explained

Referencing Check-In #201, Marc defines float as money insurers hold before paying claims and explains why it matters in P&C insurance.

18:58: Float, Return on Equity (ROE), and the Discipline of 95%

Michael and Marc discuss how float can support investment income and ROE, but Fairfax’s practical performance focus remains clear: deliver a disciplined 95% combined ratio.

29:15: Growth, Deals, and Acquisitions

Marc discusses how C&F evaluates new opportunities, using the pet sale and potential acquisitions as examples.

33:01: Culture & Continuous Learning

Michael reflects on C&F’s positive culture, flexibility, leadership support, and the value of continuous learning.

Marc and Sara Iuzzolino, Associate Underwriter Trainee in Surety, discuss Sara’s entry into insurance, lessons for early-career professionals, and how young employees can build toward leadership over time. The conversation centers on career ownership, confidence, networking, intern and trainee development, and the role C&F’s culture plays in making work meaningful and motivating.

Here’s a summary of what Marc and Sara discuss:

00:32: Entering Surety

Sara shares that she has just reached her C&F one-year anniversary, and explains how a marketing background and an internship led her into insurance, and ultimately to a Surety trainee role at C&F.

03:20: Revisiting Check-In 189

Sara introduces Marc’s earlier thoughts and asks whether he always intended to pursue senior leadership. Marc explains that leadership became clearer over time and emphasizes intentionally building skills, experiences, and readiness for future roles.

08:54: Getting Exposure Early

Marc explains how focusing on being useful and adding value gave him early access to senior-level conversations.

16:41: Being Young in Senior Executive Meetings

Sara asks about feeling intimidated as a younger professional, and Marc says confidence comes from knowing why you were invited.

22:51: Networking and Building a Cohort: Check-In 156

They discuss how networks expand over time and why building relationships with peers and future leaders matters early on.

27:12: Interns, Trainees, and Choosing Insurance

Marc shares his personal path to insurance. He notes that most people do not study specifically for insurance careers and that curiosity and willingness to learn matter more.

39:01: Advice and Perspective of the Next Generation

Sara challenges stereotypes about Gen Z and says she feels energized by C&F’s supportive culture and work environment.

40:12: In-Person Connection and Culture

Sara describes the strong sense of support among Surety trainees, including shared study efforts and daily walks. Marc emphasizes the value of office interaction, informal relationship-building, and the importance of not taking strong company culture for granted.

Watch the full podcast and share your thoughts in the comments!

00:24: Intro

Marc welcomes John and sets an informal tone with jokes about “wrestling with chaos,” John’s Dallas-era look, music background, and other early interests.

03:09: Finding Actuarial Work

John explains how he discovered actuarial science at the University of Wisconsin and was drawn to its mix of math, business, and insurance.

07:16: Early Career Lessons

John covers his early roles at Saint Paul, TIG, and Travelers, reflecting on how underwriting discipline, market-share decisions, and preserving core capabilities can shape an insurer’s long-term success or struggles.

20:52: John's Start at C&F

John recalls joining C&F in Houston in 2013 and how his role grew from actuarial leadership into broader responsibility across Fairmont, middle market, and risk management businesses.

27:12: Trust, Mobility, and Leadership

Marc and John discuss career moves built on trust, including John’s move to New Jersey, and the value of confidence and resilience when roles are not fully defined.

32:02: Legacy and Opportunity

Marc frames John’s business as balancing C&F’s legacy commercial platform with opportunistic growth. John describes the retail multiline business as a disciplined “ground game” built on relationships and organic expansion.

40:57: Cyber Discipline

John explains how C&F built cyber capabilities, grew when conditions were attractive, and pulled back as the market softened, making cyber a case study in cycle discipline.

47:44: 2035 Vision

John outlines a long-term vision for Commercial Lines, with P&C and financial/executive lines each moving toward major scale through capability-building and disciplined growth.

52:32: Staying Relevant

Marc and John close by emphasizing future relevance, claims expertise, relationships, disciplined execution, and readiness when market dislocations create opportunity.

Here's a summary of what Marc and Steve discuss:

00:38: Career Path

After a short DJ stint, Steve explains how he entered insurance unexpectedly after graduating with an electrical engineering degree during a weak job market. He joined Factory Mutual as a field engineer and discovered that insurance offered more than he originally expected.

05:28: Move to Underwriting

After Steve took graduate business courses, he realized he was more interested in the business side of insurance. He reset his career path by taking an entry-level underwriting role at Allendale Mutual.

11:48: Industry Evolution

The discussion explores how property underwriting changed from the early 1990s to today, including the move from named perils to all-risk forms. Steve shares his view that catastrophe models today are highly useful, even if they are not exact predictors of loss.

18:38: Soft Market and an Undated Division Strategy

Steve outlines how C&F is responding to the soft market by exiting unprofitable segments, advancing product development, and preparing operationally for future opportunities. He explains that his team is using this period to prepare to move from a follow market to a lead market.

27:40: Talent Development

Steve highlights C&F’s approach to hiring college graduates and notes that the company has refined its training program. He sees strong value in developing underwriters in C&F’s own technical underwriting culture.

30:03: Product Recall

Steve explains product recall as a specialized business with a smaller universe of insurable accounts, but one that has performed well for C&F when underwritten carefully.

33:09: Data Centers

The conversation turns to data centers as a major current theme in property and builder’s risk. Steve describes the rapid growth and challenges in large-scale projects.

36:07: Builder's Risk

Steve explains how builder’s risk differs from operational property coverage. He notes that the later stages of a project can be especially challenging because values are high, while systems and protections may not yet be fully operational.

38:00: The Future of the Property Division

When asked about how property insurance will evolve in 2035, Steve explains that the goal of the shared and layered property market is to be a lead market, and shares the significance and benefits that will occur as a result.

39:40: AI and Technology in Underwriting

Steve discusses how AI and technology is beginning to help with underwriting research, submission triage, and early-stage risk review. Newer technologies, such as satellite imagery could be used for assessing roof condition and other visible characteristics and could eventually reduce the need for some traditional inspection activity.

Here's a summary of what Marc and Barb discuss:

00:40: Barb's Career Path

Barb explains that entering insurance was a “happy accident,” while her path into HR came through retail leadership, executive training, mentors, and leaders who recognized her strength in working with people.

13:17: Work Environment Pivot at C&F

Barb describes joining C&F in January 2020 with plans to learn the business in person, only to quickly help lead the company through COVID, marking a major shift to remote and hybrid work.

17:17: Cultural Development

Barb reflects on C&F’s cultural progress from an HR perspective, including investments in Workday, BERTI, ERGs, clubs, and intentional moments of connection across a decentralized organization.

22:00: Managing Hybrid

Marc and Barb discuss C&F’s steady, trust-based approach to hybrid work, emphasizing employee listening, flexibility, clear communication, and avoiding the whiplash many companies created by repeatedly changing policies.

28:43: Talent & Mobility

Barb outlines C&F’s approach to career development, mobility counseling, learning journeys, job shadowing, mentorship, insurance credentials, and the move from external headhunters to a stronger in-house recruiting model.

38:50:Career Plateaus

Barb advises employees who feel stuck to take ownership of their careers by speaking with managers and HR, using development resources, building networks, seeking exposure, and being open to nonlinear moves.

53:01: Fortune 100 Recognition

Barb explains the Great Place to Work and Fortune 100 Best Companies process, noting that C&F’s recognition reflects employee feedback, strong development programs, trust, belonging, advancement opportunities, and ethical culture.

59:26: 2035 Vision

Barb and Marc envision 2035 as a time when insurance is more visible and attractive to young talent, C&F has even stronger mobility and connection through our events-driven culture, and employees are actively learning how AI can improve their work.

Here's a summary of what Marc and Matt discuss:

00:00: Introduction & Matt’s Career Path

Marc introduces Matt Lubin and asks about his entry into the surety business, highlighting Matt’s unconventional route from retail to insurance and eventually to surety.

05:38: What is Surety?

Matt provides a layman’s explanation of surety, its origins, and its role as a pre-qualification service for public works, referencing the Miller Act.

07:18: Surety Industry Model & Profitability

Discussion on the business model of surety, its profitability, and the risks involved, including loss cycles and the importance of skillful underwriting. Examples from Matt’s prior experience at Chubb Insurance.

14:40: Type of Surety Products

Overview of contract surety vs. commercial surety, including bail operations and other financial guarantees.

16:59: Industry Historical Context

The unique nature of surety claims, including active management of exposures and the role of the claims team in mitigating losses.

19:49: Relationship Management & Underwriting

The importance of ongoing client relationships, the three C’s of surety underwriting (capacity, capital, character), and the role of indemnity agreements.

27:35: Commercial Surety & MGAs

Discussion of commercial surety and the lower barriers to entry compared to contract surety, including shared surety.

29:42: C&F Surety Division Transformation

Marc and Matt discuss the challenges and turnaround of C&F’s Surety division, including rebranding and restructuring.

41:14: Culture & Talent Development

Focus on hiring and training new talent, the importance of culture, and building a pipeline of future leaders within the division.

51:52: Vision for the Future

Matt shares his vision for C&F Surety in 2035, including expansion, profitability, and becoming a top six player, with potential for international growth.

Here's a summary of what Marc and Lauren discuss:

00:57: Fortune 100 Workplace Honor

C&F was named to Fortune’s 100 Best Companies to Work For. Marc says the recognition is gratifying, but the real goal was to build a place people truly enjoy working. A strong culture isn’t just about employee relations, it’s a long-term business strategy. Marc aims to prove that culture translates into superior external relationships.

10:23: Market Cycles

Marc explains hard versus soft insurance markets. He describes the recent hard market as relatively rational and disciplined, while warning that the industry is now entering a softer phase where pricing and terms can deteriorate quickly as competitors chase growth.

19:22: What to Watch for in a Soft Market

The discussion turns to the indicators of a softening market. Premium shrinkage, retention quality, rate adequacy, business mix, and adverse selection all matter, and soft markets create more ways to get results wrong than hard markets.

26:20: Why the Soft Market is Exciting

Marc says he is looking forward to the soft market because it will test C&F’s underwriting, actuarial, and analytical discipline. He uses cyber as an example of a business where C&F scaled up when conditions were attractive and pulled back when the market became irrational.

34:47: Rate Signals

They discuss rate change data, including the appendix showing generally positive pricing by line of business. Marc cautions that rate alone is not enough; teams must also understand what was retained, what was lost, and whether C&F is avoiding adverse selection.

37:34: Q1 Results

Lauren and Marc review Q1 consolidated production, which was below both prior year and plan. Marc says the shortfall is not necessarily alarming in a softening market, but makes forecasting more difficult and increases the need for realism for rest of the year.

53:21: Underwriter Advice

Marc offers guidance for underwriters experiencing their first soft market. He stresses the importance of working with actuaries and developing a mental model for navigating future cycles.

1:00:24: Use the Time

A soft market does not have to mean unprofitable business or wasted time. Marc encourages employees to keep working hard, pursue opportunities selectively, and use slower periods to build skills, and prepare for the next favorable part of the cycle.

Time Stamps

00:53 - Tom’s Origin Story Tom

03:12 - The C&F Origin Story

16:56 - From “Data-Free” to Data Driven Marc and Tom

35:09 - Limits Discipline and Nuclear Verdicts

39:50 - Market Cycle and MGA/Fronting Model Risk

43:04 - Gig Economy and Telematics

49:54 - S&S Today

56:48 - Readiness for the Coming Headwinds

1:00:13 - The Benefits of the Long View

1:03:42 - Future Runway and AI

In this video, Marc Adee and Lauren Train chat about the President’s Report at C&F—why it matters, how it’s evolved, and how everyone can use it. They break down what’s inside, from key company results to division highlights, and encourage all employees to dive in, ask questions, and really get to know the numbers. Their message: the more you understand the report, the more you can contribute to C&F’s success!

Page Numbers Mentioned & Time Stamps

3 (PDF, C&F consolidated results) 13:13 Start of metrics discussion, gross premium, underwriting result

39 (Appendix, C&E exhibit) 39:56 Divisional analysis for C&E

40 (Appendix, C&E detail) 45:56 Dive into Executive Risk and underwriting profit

95 (Appendix 5, five-year history) 53:05 Historical perspective for C&E

35 (Appendix, S&S summary) 56:45 S&S division summary and comparison

82 (Appendix, S&S accident year results) 59:13 S&S accident year results, historical trends

38 (Appendix, S&S historical accident years) 1:05:00 S&S historical accident years, unfavorable development

11 (Appendix, five-year track record) 28:38 Five-year track record, ROE discussion

12 (appendix, trend lines) 29:45 Trend lines, used in A&H conference room

5 (Appendix, float by division) 27:41 Float generated by divisions, S&S vs. A&H

4 (Appendix, year-to-date block) 26:16 Year-to-date results, repetition of main metrics