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$7.7B insurance firm acquisition backstory: meet the (AI) speed of the moment

The Baldwin Group, in conversations that began in April, put together a $7.7 billion deal to sell itself and go private to adjust to new industry realities.

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Latest News

1
  • October 28, 2026
Naples senior living campus sells for 63% below 2021 sale price
2
  • October 28, 2026
VA commissions 135K-square-foot outpatient clinic in Sarasota County
3
  • October 28, 2026
Sarasota gun dealer buys building for $1.65M
4
  • October 28, 2026
Chicago trucking entrepreneur plans high-end Naples nightclub
5
  • October 28, 2026
Hoffmann buys Naples yacht club

40 Under 40

Relive the Business Observer's 40 Under 40 issue — in photos, videos
  • October 15, 2026
Relive the Business Observer's 40 Under 40 issue — in photos, videos
40 Under 40 class of 2026 brings elevated list of achievements
  • October 8, 2026
40 Under 40 class of 2026 brings elevated list of achievements
Tampa liquor store chain owner modernizes his way to an $11M business
  • October 8, 2026
Tampa liquor store chain owner modernizes his way to an $11M business
Sarasota developer reflects on lead-up to Waldorf project
  • October 8, 2026
Sarasota developer reflects on lead-up to Waldorf project
Next-generation leader implements processes at SWFL family flooring business
  • October 8, 2026
Next-generation leader implements processes at SWFL family flooring business
Young entrepreneur flees California to build SWFL affordable housing leader
  • October 8, 2026
Young entrepreneur flees California to build SWFL affordable housing leader
College basketball star takes family awnings firm to new heights
  • October 8, 2026
College basketball star takes family awnings firm to new heights
SWFL interior design exec turns childhood dreams into reality
  • October 8, 2026
SWFL interior design exec turns childhood dreams into reality
Non-CPA's energy, acumen help CPA firm soar
  • October 8, 2026
Non-CPA's energy, acumen help CPA firm soar
SWFL car rental giant exec prioritizes constant improvement
  • October 8, 2026
SWFL car rental giant exec prioritizes constant improvement
Founder leads Tampa mortgage firm to hit five-year mark, now in four states
  • October 8, 2026
Founder leads Tampa mortgage firm to hit five-year mark, now in four states
Sarasota-based Amish furniture exec helps build $3M Amazon channel
  • October 8, 2026
Sarasota-based Amish furniture exec helps build $3M Amazon channel
Champion athlete-turned-investor, entrepreneur builds development firm
  • October 8, 2026
Champion athlete-turned-investor, entrepreneur builds development firm
Sarasota startup capital firm co-founder helps raise $100M for clients
  • October 8, 2026
Sarasota startup capital firm co-founder helps raise $100M for clients
Tampa entrepreneur, immigrant, builds $3.5M, 24-employee real estate business
  • October 8, 2026
Tampa entrepreneur, immigrant, builds $3.5M, 24-employee real estate business
Bradenton entrepreneur reboots career from software engineer to COO
  • October 8, 2026
Bradenton entrepreneur reboots career from software engineer to COO
Bradenton HR leader, 'cycle breaker' to launch 24/7 coaching app
  • October 8, 2026
Bradenton HR leader, 'cycle breaker' to launch 24/7 coaching app
SWFL recruiting director specializes in finding top executive talent
  • October 8, 2026
SWFL recruiting director specializes in finding top executive talent
SWFL construction exec rises quickly after COVID relocation
  • October 8, 2026
SWFL construction exec rises quickly after COVID relocation
Young Lakeland attorney grows into statewide leader on elder law
  • October 8, 2026
Young Lakeland attorney grows into statewide leader on elder law
University director connects USF research with Tampa Bay's high-tech future
  • October 8, 2026
University director connects USF research with Tampa Bay's high-tech future
Tampa nurse practitioner helps others turn healthcare expertise into businesses
  • October 8, 2026
Tampa nurse practitioner helps others turn healthcare expertise into businesses
From the courtroom to the soccer pitch, lawyer finds a path to 'yes'
  • October 8, 2026
From the courtroom to the soccer pitch, lawyer finds a path to 'yes'
Fashion designer-turned-hairdresser now runs three companies
  • October 8, 2026
Fashion designer-turned-hairdresser now runs three companies
From laborer to leader, Fort Myers native builds a future for family’s business
  • October 8, 2026
From laborer to leader, Fort Myers native builds a future for family’s business
Tampa native brings creativity to regional banking
  • October 8, 2026
Tampa native brings creativity to regional banking
Executive engineers rapid growth at Garver's Tampa aviation hub
  • October 8, 2026
Executive engineers rapid growth at Garver's Tampa aviation hub
Engineering exec comes 'full circle' at manufacturer where he interned
  • October 8, 2026
Engineering exec comes 'full circle' at manufacturer where he interned
Bloomin' Brands leader builds better workplaces through trust, authenticity
  • October 8, 2026
Bloomin' Brands leader builds better workplaces through trust, authenticity
St. Pete contractor buys building, launches AI-fueled startup
  • October 8, 2026
St. Pete contractor buys building, launches AI-fueled startup
Naples senior living exec reflects on personal career 'why'
  • October 8, 2026
Naples senior living exec reflects on personal career 'why'
Early real estate purchase helped Naples executive’s career
  • October 8, 2026
Early real estate purchase helped Naples executive’s career
SWFL tech exec goes from startup to 10K-square-foot HQ
  • October 8, 2026
SWFL tech exec goes from startup to 10K-square-foot HQ
Running a $4 billion investment fund leaves little time
  • October 8, 2026
Running a $4 billion investment fund leaves little time
SMH leader builds relationships, pays it forward
  • October 8, 2026
SMH leader builds relationships, pays it forward
SWFL air traffic controller lands patent-pending tech service
  • October 8, 2026
SWFL air traffic controller lands patent-pending tech service
Lee schools official finds consensus amid chaos
  • October 8, 2026
Lee schools official finds consensus amid chaos
Necessity creates opportunity for SWFL children's party gear entrepreneur
  • October 8, 2026
Necessity creates opportunity for SWFL children's party gear entrepreneur
TV news anchor shifts to helping nonprofits shine — and raise more funds
  • October 8, 2026
TV news anchor shifts to helping nonprofits shine — and raise more funds
Fitness entrepreneur with fast success craves more impact, growth
  • October 8, 2026
Fitness entrepreneur with fast success craves more impact, growth
New United Way CEO guides $21.7M organization into new era
  • October 8, 2026
New United Way CEO guides $21.7M organization into new era

Commercial Real Estate

  • October 28, 2026
Naples senior living campus sells for 63% below 2021 sale price
  • October 28, 2026
VA commissions 135K-square-foot outpatient clinic in Sarasota County
  • October 28, 2026
Sarasota gun dealer buys building for $1.65M
  • October 28, 2026
Chicago trucking entrepreneur plans high-end Naples nightclub

Entrepreneurs

  • October 28, 2026
Hoffmann buys Naples yacht club

The business empire with local roots has added the Hamilton Harbor Yacht Club to its ever-growing lists of companies.

  • October 21, 2026
With over 10M followers, viral Manatee toy store owner rides squishy fame wave

Fidget Toys Plus owner Faith Bench is a teacher-turned-entrepreneur who has become a global sensation for her videos of sensory toys and pioneering an activity called fidget trading.

  • September 11, 2026
Work to begin on $15M luxury car and social club in Sarasota

Scott Stevenson recently began accepting memberships for Sarasota Motor Club, which will offer a place for car enthusiasts to gather and store their luxury, exotic or collector vehicles.

  • September 9, 2026
Madeira Beach boutique damaged by Helene reopens two years later

Hubbard’s Marina’s shop in John’s Pass Village in Pinellas County is back after suffering structural damage and facing delays in construction work.

Food-Beverage

  • October 28, 2026
Chicago trucking entrepreneur plans high-end Naples nightclub

The club’s plans, according to the owner, include a "three-hour show featuring singers, dancers, aerialists and live music in a spectacular, theatrical setting."

  • October 28, 2026
Buzzy California coffee chain makes Florida debut in Tampa Bay
  • October 23, 2026
Down at least $500K in sales, Tampa nightlife landmark plans bankruptcy
  • October 22, 2026
Bagels & Co. enters Tampa market with shop near USF
  • October 7, 2026
Tampa-based burger chain launches drive-thru makeovers as part of turnaround

Finance

  • October 27, 2026
$8B credit union’s Sarasota bank purchase reflects shifting M&A market

DFCU Financial looks for leadership and personnel alignment first in a bank acquisition, then demographics and financials. It found all three in Gulfside Bank.

  • October 26, 2026
$7.7B insurance firm acquisition backstory: meet the (AI) speed of the moment
  • October 20, 2026
Tampa credit union names new CEO as longtime leader departs
  • October 19, 2026
Michigan credit union to acquire Sarasota community bank
  • October 12, 2026
Tampa Bay Wave picks 13 startups for fintech accelerator

Healthcare

  • October 28, 2026
VA commissions 135K-square-foot outpatient clinic in Sarasota County

Construction is expected to start at the Lakewood Ranch Boulevard site in summer 2027, with the project's completion projected for summer 2029.

  • October 23, 2026
$23M Tampa health firm pursues deal for telehealth, drone delivery tech

DataMEDS AI’s proposed acquisitions and licensing agreements would expand its digital health platform, with one partner seeking a 19.9% ownership stake.

  • October 19, 2026
Chewy Vet Care opening clinic in Manatee County

The Parrish location will mark the ninth veterinary clinic in Florida for Chewy.

Residential Real Estate

  • October 28, 2026
Naples-based brokerage names next CEO

Budge Huskey, the CEO of Premier Sotheby's International Realty, will turn over leadership of the firm in 2027.

  • October 27, 2026
Builder plans 825-home community in south Sarasota County

More than 800 homes will be built between Englewood and Wellen Park by the end of 2029, according to Pat Neal, owner of Neal Communities.

  • October 22, 2026
Gulf-front Naples mansion sells for $71M in off-market sale

The waterfront estate spans more than 9,500 square feet under air-conditioning and was just completed in 2026.

More News

  • October 28, 2026
Naples-based brokerage names next CEO
  • October 28, 2026
Buzzy California coffee chain makes Florida debut in Tampa Bay
  • October 28, 2026
Florida land and agribusiness CEO plans retirement
  • October 27, 2026
Builder plans 825-home community in south Sarasota County
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Advice

1
  • October 13, 2026
AI doesn't need emotional intelligence — but AI-concerned leaders do
2
  • September 9, 2026
Your organization doesn't need a workshop. It needs coaching infrastructure.
3
  • August 4, 2026
The family meeting: The best way to prep your family for what comes next

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