Alleghany Bank of America Merrill Lynch 2020 Insurance Conference February 13, 2020

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Alleghany
Bank of America Merrill Lynch 2020 Insurance Conference
                  February 13, 2020
Conservative Management Approach

          Philosophy                                     Strategy

                                   1   Own high-quality underwriting franchises
“Conservatism dominates our
                                        ―   Underwrite for profit
management philosophy. We               ―   Grow premiums only when market allows
                                            for profitable growth
  shun investment fads and              ―   Consistently maintain appropriately
                                            conservative loss reserves
fashions in favor of acquiring
                                   2
                                       Invest for total return when risk/reward is
                                        attractive
  relatively few interests in
                                   3
                                       Acquire quality businesses at reasonable prices
basic financial, industrial and         ―   Provide resources, support and oversight to
                                            help them grow revenues, profits and
other enterprises that offer the            returns

potential to deliver long-term     4
                                       Maintain a conservative financial and operating
                                        risk profile

    value to our investors”        5   Hold significant unrestricted liquidity for
                                        potential opportunities (and downturns)

                                                                                          2
Attractive & Consistent Returns

                                                        600
                                                                                                                                                                  554.6
                                                                                                           CAGR
  Continued                                                                             Q3 '19 YTD Since '13     Since '09   Since '99                             509.4
   Focus on                                             500    Y BVPS                        16.1%       7.4%         8.0%        8.6%
 BVPS Growth                                                   Y Share Price                28.0%        13.1%       12.1%        9.1%
                                                               S&P 500 (Total Return)       20.6%        10.9%       12.9%        5.7%

                                                        400
                                 Indexed Total Return

                                                                                                                                                                   297.1
   Long-term                                            300

  Conservative
  Orientation
                                                        200

                                                        100
      Quasi-                                                                                                                                     Target Annual
                                                                                                                                                Growth in BVPS:
   autonomous                                                                                                                                      7% - 10%
    Subsidiary
                                                         0
    Operating                                                 1999      2001     2003       2005       2007        2009       2011       2013     2015   2017   Q3-2019
      Model                                                                       Y BVPS             Y Share Price            S&P 500 (Total Return)

Note: As of September 30, 2019. Compound annual growth rates (“CAGR”) for BVPS and Stock Price include the impact of $10 special dividend paid in 2018.

                                                                                                                                                                           3
Modest Financial Leverage and Conservative Risk Profile

                           Debt to Capital                                                                  Holding Company Liquidity
                                                                Other Debt (ACC)               (millions)
                                                                Senior Notes
                                                                                                                                           $1,383
                                                                                                                                                                      $1,294
     19.4%
                                                          17.5%                     13.4%                                                                $1,122
                                                                                                   $1,032                     $1,047
                   15.8%        15.6%                                  15.8%         excl.
                                             14.7%
                                                                                    2020                          $821
                                                                                   notes (1)

      2014         2015          2016         2017         2018       Q3-2019                        2014         2015         2016          2017         2018       Q3-2019

 Peak Zone PML / Shareholder Equity(2)                                                             Risk Assets / Shareholders’ Equity(3)
                                                                                                                                            0.62x
                    10%                                                                                                                                  0.58x
       9%                                                                                           0.51x        0.52x         0.53x
                                               8%            8%
                                  7%
                                                                          6%                                                                                          0.34x

      2014          2015         2016         2017         2018       Q3-2019                       2014          2015         2016         2017          2018      Q3-2019
(1) Alleghany 2020 Senior Notes were redeemed on January 15, 2020.
(2) Reflects net occurrence PML (after-tax) in a 1-in-250 year event (having a likelihood of being exceeded in any single year of 0.4 percent) for largest single zone peril (i.e.
    Florida wind).
(3) Risk assets are defined as high yield bonds, below investment grade collateralized loan obligations (“CLOs”) and bank loans, publicly traded equity securities, private
    equity and partnership interests.

                                                                                                                                                                                     4
Alleghany Today

                                                                                                                                      Alleghany
   Reinsurance                                              Insurance
                                                                                                                 Investments           Capital
          53%(1)                                                  27%(1)
                                                                                                                                         20%(1)

                                                                                                                     Asset           Subsidiaries &
        TransRe                                RSUI                            CapSpecialty
                                                                                                                  Management          Investments

  GAAP equity of                    GAAP equity of $1.9                  GAAP equity of                       $16.2 billion
   $5.3 billion                       billion                               $0.4 billion                          fixed income

  Gross premiums                    Gross premiums                       Gross premiums                       $2.1 billion
   written of $4.7                    written of $1.3                       written of $0.4                       equity portfolio
   billion                            billion                               billion
                                                                                                                 $0.6 billion
  Top 15 global                       10th largest U.S.                  Focuses on niche                      other invested
   reinsurer(2)                         excess & surplus                    specialty                             assets
                                        lines group(3)                      commercial lines

                                         90 years as a public company (NYSE: Y)
Notes: Financial data as of September 30, 2019 unless otherwise indicated. Gross premiums written for the trailing 12 months.
(1) As of September 30, 2019, YTD % Contribution to adjusted earnings before interest and taxes, excluding corporate items.
(2) Best’s Review March 2019 – Top 50 Global Reinsurers; ranking based on unaffiliated gross premiums written in 2018.
(3) A.M. Best U.S. Surplus Lines – Segment Review, September 2019.

                                                                                                                                                  5
Current (Re)insurance Operations
 ($ in millions)

                                                                                                          Cumulative Results Over Holding Period

                                                                                           Net              Underwriting
    Subsidiary /                Cash &            Stockholders’           Years         Premiums               Profits             Combined       Net
  Acquisition Date            Investments            Equity               Held           Written              (Losses)               Ratio     Dividends    IRR

                                $13,541               $5,348                 7          $28,320                 $1,179                 95.7%   $1,492(1)   10.2%
 March 6, 2012                   2.5x

                                  3,837                1,858                16            11,776                 1,785                 84.2     1,124      11.6
                                   2.1x
 July 1, 2003

                                   846                   413                17            3,430                  (28)                  100.8     130        5.6
January 1, 2002                    2.1x

 Total
                              $18,257(2)              7,639(2)
 (Re)insurance
                                2.4x

Note: As of September 30, 2019.
(1) Total dividends to Alleghany of $1,800 million less a $309 million capital contribution in 2014 primarily to repay senior notes.
(2) Inclusive of AIHL Re.

                                                                                                                                                           6
Consolidated Underwriting Results for Past 10 Years

                    Underwriting Profit                                                                           Combined Ratio

                                      $495                                                      83.0%
                                             $467                                          84.7%
                               $421
                                                    $401
                                                                                                                             88.8%
                                                                                                                                   89.0%
                                                                                                                        90.1%
                        $220                                            $232                                                           91.9%
                                                                                                          93.4%
   $129 $131                                                                                                      94.1%                                          94.3%
                                                                                                                                                       94.5%

                 $50

   Pre-TransRe                                                                               Pre-TransRe
                                                                                                                                                             103.2%
                                                                  ($162)

                                                                                                                                                     106.4%
                                                           ($316)
    '09    '10    '11    '12    '13    '14    '15    '16    '17     '18 Q3 '19               '09    '10    '11    '12     '13   '14    '15     '16     '17    '18 Q3 '19
                                                                         YTD                                                                                       YTD

          2009-to-Date Underwriting Profits of $2.1 B and Combined Ratio of
                                      ~94.5%

Note: 2019 YTD as of September 30, 2019. Underwriting profit is a non-GAAP financial measure. Refer to the appendix for further information.

                                                                                                                                                                           7
TransRe – Structural Competitive Advantages
                      Net Premiums Written(1)                                                          Diversified, global reinsurer with
                                         (Q3 2019 YTD)
                                                                                                        casualty & specialty expertise
                            Engineering              Other Specialty
                     Aviation   1%                         3%                                          Long-standing client and
             Marine & 2%
              Energy                                                                                    intermediary relationships
               4%
                                                                                                           70% proportional business
      Specialty
        26%
                                                      Personal Auto /                                      Leads or co-leads more than
                                                          Motor
                         Guaranty
                           8%
                                                           16%                                                half of its book
                                                                                                       Strong balance sheet and
                     A&H                                             Traditional                        infrastructure
                      8%                                              Casualty
                                                                        16%                            Leveraging market position with
                  Catastrophe                                                                           third party capital
                   Property
                      7%                                                                                   Generates recurring fee
                                     Non-                 Professional
                                                                                     Casualty
                                                                                                              income
                                  Catastrophe               Liability
                                   Property                   15%                      47%
                                     20%                                                                   Q3 ’19 YTD Highlights
          Property
            27%                                                                                        Net premiums written up 13%
                                                                                                       Combined ratio of 96.2%
                                       $2.8 billion(1)                                                 Underwriting profit of $122mm

       History of Prudently Navigating Market Conditions and Opportunities
(1)   Excludes Farmers quota share treaty which contributed $509 million to net premiums written.

                                                                                                                                         8
RSUI – Taking Advantage of Improving E&S Market

     Underwriting Profit                                               30 years dedicated to wholesale
       (Cumulative data for 2003 – Q3 2019 period)                      specialty insurance market
      Alternative                          D&O Liability
                                                                       Proven ability to generate
      Structures
          2%
                                               7%                       underwriting profit and grow
                                                                        book value through cycles
                                                                       Highly experienced underwriters
                                         Professional
                                                                       Nimble and reacts quickly to
                                           Liability                    opportunities
                                             23%
              Property                                                 Proprietary, in-house developed
                49%
                                                                        technology, models and
                                                        General
                                                                        analytical tools
                                   Umbrella /           Liability
                                    Excess                 7%          Diversified profitable portfolio
                                     12%
                                                                           Q3 ’19 YTD Highlights
                                                                       Net premiums written up 14%
     Cumulative Underwriting Profit:
              $1.8 billion                                             Combined ratio of 81.7%
                                                                       Underwriting profit of $111mm
Continued New Business and Rate Momentum with Double Digit Renewal
                  Rate Increases on Multiple Lines

                                                                                                           9
CapSpecialty – Repositioned for Greater Efficiency & Overall
Profitability

 Gross Premiums Written                           Well-diversified specialty company
                         (2018)
                                                  Niche product focus for small and
                                                   mid-size businesses

              Surety                              Recognized experts in select classes
               15%
                                  Property &      New CEO, Jack Sennott appointed
                                   Casualty        July 1, 2019
                                     29%
   Professional
     Liability                                    Current focus on profitable growth,
       16%                                         expense management & technology
                                                   optimization
             Specialty            Healthcare
             Casualty               20%                Q3 ’19 YTD Highlights
               20%
                                                  Net premiums written up 10%

                                                  Combined ratio of 100.1%
                  $329 million                    10-point improvement in expense
                                                   ratio since 2014

Meaningful Progress Towards Its Goal of Becoming A Preferred Specialty
             Insurer for Small and Mid-Sized Businesses

                                                                                       10
Alleghany Capital – Becoming a More Meaningful Contributor

           Adjusted Earnings Before Tax(1) – 100% Basis                                                                       Permanent capital
                                                                                                                                    provider to leading
                                                                                                                                    middle-market
                                                                                                                                    businesses
 ($ millions)                                                                                             $140

                                                                                                                  $124
                                                                                                                              Partners with aligned
                                                                                                                                    entrepreneurial
                                                                                  $93                                               management teams /
                                                                                                                                    founders with high
                                                          $64                              $82                                      integrity
                                  $43                             $51
                                                                                                                              Acquire leaders in niche
         $25                                 $31                                                                                    markets, or rapid share
                     $14                                                                                                            gainers in large
                                                                                                                                    fragmented markets

         2015                     2016                   2017                    2018               Q3 2019 YTD
                                                                                                                              Accelerate operational
                                                                                                                                    efficiency improvements;
        Corporate Activity & Deal Expenses                          Non-Industrial                                                  follow-on capital for
        Industrial                                                  Adjusted EBT (Net of Corp. Activity & Deal Expenses)
                                                                                                                                    growth / add-on
                                                                                                                                    acquisitions

         Diversified Portfolio of High-Performing Businesses Helps Mitigate
                           Individual Business Seasonality
(1)   Adjusted earnings before income taxes (“Adjusted EBT”) represents noninsurance revenue less all operating expenses, and does not include: (i) amortization of
      intangible assets; (ii) change in the fair value of equity securities; (iii) net realized capital gains; (iv) other than temporary impairment ("OTTI") losses; and (v) income
      taxes.

                                                                                                                                                                                      11
Key Macroeconomic & Industry Themes

             Opportunities                                    Challenges

1
1)   E&S market is firming                     1
                                               1)   Late in economic cycle (elevated
                                                    sovereign, corporate and household
                                                    debt)
     - Significant competitors
       retrenching
                                               2
                                               2)   Geopolitical uncertainty (including
                                                    trade)
     - Changing view of certain risks
       (e.g., wildfires, casualty inflation)
                                               3
                                               3)   Low return world
     - Limits contraction
                                               4)
                                               4    High asset prices (public and
2                                                   private)
2)   Reinsurance market slowly
     improving
                                               5)
                                               5    Industry consolidation
3
3)   Opportunistic capital allocation
                                               6
                                               6)   Increasing loss cost trends / social
                                                    inflation in casualty lines

                                                                                           12
RSUI – Accelerating Rate Increases and Increasing Opportunity
 15%
                                                             Renewal Rate Change (%)
12%

  9%

  6%

  3%

  0%

 -3%

 -6%
           Q1 '17       Q2 '17        Q3 '17       Q4 '17       Q1 '18        Q2 '18          Q3 '18   Q4 '18   Q1 '19    Q2 '19    Q3 '19    Q4 '19

 50%
                                                     New Business Submissions (Units)
 40%

 30%

 20%

 10%

  0%

-10%

-20%
            Q1 '17       Q2 '17        Q3 '17       Q4 '17        Q1 '18       Q2 '18         Q3 '18   Q4 '18    Q1 '19    Q2 '19    Q3 '19    Q4 '19

Note: Data is quarterly rate and new business submission increases over prior-year quarter.

                                                                                                                                                        13
Alleghany Capital – 2019 Bolt-On Acquisitions

            Wicked Cool Toys (Oct-2019)              Warren Manufacturing (Jul-2019)

   Jazware’s 4th acquisition since Alleghany’s    Acquired animal feed transportation assets
    investment
                                                   Deepens market share in animal feed
   Deepens management talent                       transportation segment
   Adds iconic brands such as Pokémon and         Broadens geographic coverage
    Cabbage Patch Kids to an already
    impressive portfolio

   CID Performance Tooling (Jun-2019)                 The Cardinal Group (Apr-2019)

   Leading manufacturer of consumable             Significantly expands IPS footprint in the
    precision cutting tools                         Northeast, a key biopharmaceutical hub
   Stable, recurring source of revenue for PCT    Adds highly experienced management
                                                    team, particularly in construction
                                                    management

                       $250 Million of Capital(1) Deployed in 2019

(1) Debt and equity.

                                                                                                 14
Slowing U.S. & Global Growth

   8.0%

   6.0%
                                                                                                                                              5.7%

   4.0%

                                                                                                                                              2.5%
   2.0%                                                                                                                                       1.8%
                                                                                                                                              1.0%
   0.0%

 (2.0)%

 (4.0)%

 (6.0)%
            1998         2000         2002         2004        2006         2008         2010         2012    2014       2016       2018   2020E

                                       World              United States             European Union            East Asia & Pacific

    What Impact Will The Coronavirus Outbreak Have on Growth?

Source: World Bank. GDP growth (annual %) based on constant local currency and U.S. dollars for aggregates.

                                                                                                                                                     15
Investment Environment Remains Challenging

                        Treasury Yields & Credit Spreads                                      Is the S&P 500 Overpriced?
                                                                                  35.0x
                 4.5%
                                                                                                                                               32.1x

                 4.0%                                                Jan 2018 -
                                                                                  30.0x
                                                                     Feb 2020

                 3.5%
                                                                                  25.0x
                 3.0%
Yield / Spread

                                                                                  20.0x
                 2.5%

                 2.0%                                                             15.0x                 30%

                                                                                                        20%
                 1.5%                                                                                    10%
                                                                          1.56%                                                   Slowing
                                                                                  10.0x                                           Growth
                                                                          1.28%                          0%
                                                                                                                                         1.92%
                 1.0%
                                                                                                       (10%)
                                                                                   5.0x                (20%)
                 0.5%                                                                                       2014 2015 2016 2017 2018 2019
                                                                                                                  Quarterly Earnings Growth

                 0.0%                                                              0.0x
                     2010    2012      2014     2016          2018      2020           2009    2011   2013      2015       2017         2019

                             UST 10Y            BBB Credit Spreads
                                                                                                      Shiller P/E - S&P 500

     Source: Bloomberg. Market data as of February 10, 2020

                                                                                                                                                 16
Alleghany’s Tactical Response

1   Prudently manage underwriting risks
     - Reduction in emerging risks where future severity not reflected in current pricing (e.g., cyber)

     - Conservatism in property-cat opportunities where rate still not sufficient (e.g., Florida reinsurance)

     - Grow where significant rate, terms and conditions allow (Attritional Property, Umbrella / Excess, D&O,
       Professional Liability)

     - Focus on aggregations and tail risk

2   De-risk investment portfolio
     - Reduced size of equity portfolio by more than half

     - Sold lower quality fixed income securities

3   Efficiently deploy capital
     - Allocate capital to ACC to support bolt-on acquisitions at existing portfolio companies

     - Return capital to shareholders

     - Potential to de-lever balance sheet over time; retired $300 million of debt in January 2020

4   Maintain sufficient dry powder for eventual opportunities
     - Significant holding company liquidity

     - Meaningful debt capacity

                                                                                                                17
Key Takeaways

   Long-term focus with track record of consistent growth in book value
    per share, despite significant headwinds over last 3 years

   TransRe and RSUI are strong franchises in their respective market
    segments with improving outlook

   Alleghany Capital has achieved critical mass with prospect of improved
    earnings contribution and double-digit return on equity

   Holding company conservatively capitalized with significant optionality

   Reiterating long-term goal of 7 to 10% growth in book value per share

                                                                             18
Appendix
Capital Allocation as of September 30, 2019
  amounts in millions, except book value per share

Consolidated:                                                                         Alleghany Capital Operating Entities:

Stockholders' Equity                       $          8,829              89.9%        W&W|AFCO Steel                                        $       275     2.8%
                             (1)
Parent Company Debt                                      994              10.1%       Jazwares                                                      233     2.4%
Total Capital                              $         9,823            100.0%          Concord                                                       109      1.1%
                                                                                      Precision Cutting Technologies                                103     1.0%
Shares outstanding (mm)                               14.41                           Wilbert (45% investment)                                        79    0.8%
BVPS                                       $        612.87                            IPS                                                             69    0.7%
Market Capitalization                      $         11,795                           Kentucky Trailer                                                79    0.8%
                                                                                      Total Alleghany Capital                              $        947     9.6%

(Re)insurance:                                                                        Other:

TransRe                                    $           5,348             54.5%        Parent cash and marketable securities(2)             $      1,206    12.3%
RSUI                                                   1,858             18.9%        Stranded Oil                                                    88    0.9%
CapSpecialty                                             413               4.2%       Alleghany Properties                                            24    0.2%
AIHL Re                                                    20             0.2%        Other items, net(3)                                           (81)   (0.8%)
Total (Re)insurance                        $          7,639             77.8%         Total Other                                           $    1,237     12.6%

Note: All subsidiaries are majority owned unless otherwise stated. Market data as of February 10, 2020.
(1) Excludes $350 million par value senior notes at TransRe that mature in 2039. Also excludes $311 million of debt at ACC.
(2) Parent cash and marketable securities exclude cash at the TransRe holding company ($88 million at 9/30/2019), which is included in TransRe capital.
(3) Primarily deferred compensation and deferred taxes, as well as ACC parent.

                                                                                                                                                              20
Alleghany Capital - Platform Companies

                 Company                                Description                           Founded Revenue(1) Acquired   % Owned

                                          Manufactures specialty machine
                                           tools and, through DTI, supplies                     1975     $37       2012      100%
                                           waterjet cutting consumables

                                          Manufactures highly-engineered
Industrial

                                           custom trailers and truck bodies                     1879    $227       2013       77%
                                           for a variety of niche markets

                                          Fabricates and erects heavy
                                           structural steel for bridges and                     1945    $926       2017       80%
                                           large structures

                                          Supplies products and services to
                                           the funeral and precast concrete                     1880     $171      2017       45%
                                           markets

                                          Manages and develops hotels in
Non-Industrial

                                                                                                1985     $172      2018       85%
                                           the U.S. and Canada

                                          Provides technical consulting for
                                           the biopharmaceutical and other
                                                                                                1989    $599       2015       84%
                                           highly-complex manufacturing
                                           environments

                                          Global toy, entertainment, and
                                                                                                1997    $358      2016(2)     77%
                                           musical instrument company

 (1) LTM 3Q 2019. Revenues are on 100% basis in $millions.
 (2) 30% stake acquired in 2014. Additional 50% acquired in 2016. 3% stake sold in Q1 2018.

                                                                                                                                    21
Non-GAAP Financial Measures

This document and the remarks made during the presentation today may also contain non-GAAP financial measures.
Reconciliations of these non-GAAP financial measures to the most direct comparable GAAP measures and related
information are provided in our financial supplement and Form 10-K and 10-Q filings, which are available on our website
at www.alleghany.com, and below.

Adjusted Earnings Before Income Taxes
Adjusted earnings before income taxes represents noninsurance revenue less all operating expenses, and does not include:
(i) amortization of intangible assets; (ii) change in the fair value of equity securities; (iii) net realized capital gains; (iv)
OTTI losses; and (vii) income taxes. Because adjusted earnings before income taxes excludes income taxes, change in the
fair value of equity securities, net realized capital gains, OTTI losses and amortization of intangible assets, it provides an
indication of economic performance that is not affected by investment activity, levels of effective tax rates or levels of
amortization resulting from acquisition accounting. Alleghany uses adjusted earnings before income taxes as a
supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance
of certain of its noninsurance operating subsidiaries and investments. A reconciliation of adjusted earnings before income
taxes to earnings before income taxes is presented on page 35 of the 3Q 2019 financial supplement.

Underwriting Profit
Underwriting profit represents net premiums earned less net loss and LAE and commissions, brokerage and other
underwriting expenses, all as determined in accordance with GAAP, and does not include net investment income, net
realized capital gains, OTTI losses, other revenue, other operating expenses, corporate administration, amortization of
intangible assets and interest expense. Alleghany consistently uses underwriting profit as a supplement to earnings
before income taxes, the most comparable GAAP financial measure, to evaluate the performance of its segments and
believes that underwriting profit provides useful additional information to investors because it highlights net earnings
attributable to a segment's underwriting performance. Earnings before income taxes may show a profit despite an
underlying underwriting loss, and when underwriting losses persist over extended periods, a reinsurance or an insurance
company's ability to continue as an ongoing concern may be at risk.

                                                                                                                               22
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