The Contractor's Playbook: Built2Win

Getting bonded starts with knowing what a surety actually sees when it looks at your company. Brett Ragland learned it the hard way: his first account as a surety underwriter went bad. OSHA shut the jobsite down, and the loss cost the surety $1 million, a third of what his whole office took in premium that year.
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Brett spent 17 years on the surety side, underwriting bonds at Travelers, Continental, and CNA. Today he's a partner at Johnson & Company, an Orlando bonding and insurance agency, where he works alongside his two sons.
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Chris Coghlan asks him what a surety looks at before it bonds you. Brett walks through the three C's (character, capital and capacity), the four numbers an underwriter pulls off your WIP schedule, what the surety does when a bonded job goes bad, and why his team works off the engineer's estimate instead of your real bid number.
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If you need more bonding capacity, or will in the next few years, start here.
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Disclosure: Johnson & Company is a sponsor of The Contractor's Playbook, and Brett is a partner at the firm.
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▶ Watch every episode on The Contractor's Playbook | Built2Win:
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WHAT THIS EPISODE ANSWERS
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What is a surety bond, and why is it priced for zero losses when insurance isn't?
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What does a surety look at before it bonds you, and which four numbers on your WIP show how your jobs are really going?
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When a bonded job goes bad (a fatality, an OSHA shutdown, a missed payroll), what are the surety's options, and who pays it back?
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Why would a broker send your file to one surety instead of twenty, and why won't Brett's team take your actual bid number?
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When should a growing contractor bring in a bond agent, and why does Brett say it's easier to get bonded today than at any point in his career?
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ABOUT THE GUEST
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Brett Ragland is Senior Vice President and Partner at Johnson & Company, a family-owned Orlando commercial insurance and bonding agency founded in 1933. He has spent forty-plus years in surety, including 17 on the carrier side as an underwriter and branch manager at Travelers, Continental and CNA, before moving to the agency side.
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For 11 of those years he underwrote bonds by day and coached college baseball at Rollins and UCF by night. He works alongside his sons, Tyler and Tanner.
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Johnson & Company
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ABOUT BUILT2WIN
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Built2Win is where the ones who build the world come to think bigger, lead better, and win at a higher level — long-form conversations on leadership, construction, and building something that lasts. Hosted by Chris Coghlan.
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Our mission: elevate the contractor's voice, restore pride in the trades, and inspire the next generation of builders. When Contractors rise, America rises.
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#Built2Win #SuretyBonds #TheContractorsPlaybook #Bonding #Contractors

At 16 he was sleeping on a friend's couch after climbing in through the basement window. At 22 he was mixing mud and carrying chimney liners on a masonry crew in Franklin Park, New Jersey, because a general contractor named Billy Hendricks put him on the crew and told him he'd start at the bottom. Today he's 68, a Harvard MBA who built medical-technology companies for thirty years - and a candidate in the November 3rd runoff for Orange County Mayor.

Chris Messina sits down with Chris Coghlan for a conversation that is not about politics. It's about what a construction crew teaches you that Harvard never will, why a contractor was the first person to call him about the sewer main break near Aquatica, what a 70-step approval for a parking lot says about why Orange County is the hardest county in Florida to build in, and the $10 million trades fund he says he'd launch so a kid who's good with his hands doesn't need a quarter-million-dollar degree to build a life.

Chris Messina is a candidate for Orange County Mayor in the November 3, 2026 election. Built2Win does not endorse candidates.

The channel is The Contractor's Playbook | Built2Win - subscribe:

/ @thecontractorsplaybook-b2w

WHAT THIS EPISODE ANSWERS

What does a county mayor actually control, and why should a foreman on a job site care who has the job?

What did a masonry crew - and a GC who hired guys straight out of prison - teach a homeless kid that carried him to Hewlett-Packard and Harvard?

Why is Orange County the hardest county in Florida to build in, and what does a 70-step parking-lot approval have to do with the bottom-of-the-country wages here?

A contractor called him about the sewer line break near Aquatica before the public knew. What happened, what went wrong, and what does "burying the money" in infrastructure really mean?

You don't need to go to Harvard: how would a $10M county trades fund work, and who pays it back?

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ABOUT THE GUEST

Chris Messina is a tech entrepreneur and CEO of Body1, with 30 years founding and running medical-technology and life-science businesses in Boston, and a founding director of MassMEDIC. He holds an MBA from Harvard Business School and a master's in city planning (Rotary Fellow, Australia). He and his wife Julie co-founded the 321 Foundation for children with Down syndrome. He coaches high-school football in Orange County and is a candidate for Orange County Mayor.

Website: https://www.chrismessina.com

Facebook: / chrismessinafl

Instagram: / chrismessinafl

LinkedIn: / chmessina

ABOUT BUILT2WIN

Built2Win is where the ones who build the world come to think bigger, lead better, and win at a higher level. Hosted by Chris Coghlan - World Series champion turned construction entrepreneur - The Contractor's Playbook sits down with the builders, operators, athletes, and leaders whose stories give something useful to anyone responsible for leading a crew, growing a company, or raising up the next generation of builders.

Our mission: elevate the contractor's voice, restore pride in the trades, and inspire the next generation of builders. When Contractors rise, America rises.

Connect with us:

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#Built2Win #TheContractorsPlaybook #OrangeCounty #Orlando #Construction #Contractors #SkilledTrades #Infrastructure #Leadership #ChrisMessina #OrangeCountyMayor

There's a hammer hanging in the lobby with a piece of PVC and duct tape where the handle should be. "We could not afford a new hammer."

Chris Coghlan sits down with Ben Burgess, P.E., founder of Burgess Civil, who started in June 2014 with a tiny bit of working capital, five men hired off Craigslist, and one rented office behind a real estate receptionist he asked to pretend she worked for him. Twelve years later: Burgess Civil employs roughly 200 people, has about $100 million in backlog, $130 million in DOT bonding capacity, and the site package on the USF football stadium.

Ben didn't take a paycheck for the first three years — there are still employees at Burgess Civil with employee numbers lower than his. He ran the business and the projects during the week and estimated on weekends. Then a divorce settlement put him millions of dollars in personal debt in January 2020, and COVID shut down his residential work ten weeks later.

Ben walks through all of it: the broken hammer hanging in his lobby, cutting from 95 people to 60 and getting back to 100 within 90 days, the heavy equipment simulator that catches operators who've never actually run one, and the daily green/red scoreboard that tells every foreman whether he made or lost money that day instead of sixty days later.

If you're building a crew, deciding what to self-perform, or trying to figure out how to keep good people in the trades, this one is for you.

▶ Watch every episode on The Contractor's Playbook | Built2Win:

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WHAT THIS EPISODE ANSWERS

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How do you survive losing money on the very first job you ever bid?

What do you do when a personal crisis and a market shutdown land in the same ninety days?

How do you know a new hire can actually run the machine he says he can run?

How do you show a crew whether they made money today instead of sixty days from now?

Can an 18-year-old who starts on a shovel really retire a millionaire?

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ABOUT THE GUEST

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Ben Burgess, P.E., is the founder and owner of Burgess Civil, LLC, a Tampa-based self-perform site and civil contractor he started in June 2014. A civil engineer out of NC State with an MBA from the University of Florida, he built the company from five Craigslist hires to roughly 200 people running clearing, earthwork, underground utilities, roadwork and paving across commercial, residential and DOT work in Tampa Bay. Burgess Civil is an Inc. 5000 and repeat Gator100 honoree, and describes itself as "a training company that happens to do construction" — with core values of Integrity, Learning, Availability and Mentorship printed on every hard hat.

Website ▶ https://burgesscivil.com

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ABOUT BUILT2WIN

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Built2Win is where the ones who build the world come to think bigger, lead better, and win at a higher level — long-form conversations on leadership, construction, and building something that lasts. Hosted by Chris Coghlan.

Connect with us:

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Michael Waldrop starts this episode with a question most contractors can't answer: who cleans the port-o-lets on your jobsite?

It sounds like a small thing. He'll tell you it's the whole thing - because the answer tells him how a company treats the people doing the work when nobody's watching. And the man asking isn't a safety consultant. He has a Purple Heart and two Bronze Stars for Valor.

Six years after he resigned his commission, a Western Union mailgram told Michael Waldrop to report for Afghanistan in 30 days. He was wounded three weeks in, talked his way back onto a helicopter, and finished the tour. Today he builds the facilities that serve the veteran community he came from.

Chris Coghlan sits down with Michael Waldrop, founder and chairman of Blue Cord Design & Construction, to talk about leading men in combat, coming home, and building a construction company around the people he served with.

From receiving a property-tax bill while deployed in Afghanistan - and turning that frustration into a Florida constitutional amendment - to convincing two men to take a million-dollar chance on his vision, Michael lays out the unlikely path that led to Blue Cord.

CHAPTERS

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0:00 - Who Cleans the Port-O-Lets?

11:29 - Why He Walked Away From the Army

18:29 - The Mailgram: 30 Days to Afghanistan

36:00 - His First Gunfight

41:32 - Wounded - and Why He Went Back

49:52 - Who Would You Call at 3AM?

1:21:58 - Starting a Construction Company in 2009

1:41:32 - Inside Blue Cord: "Don't Commoditize Us"

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ABOUT THE GUEST

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Michael Waldrop is the founder and chairman of Blue Cord, a Service-Disabled Veteran-Owned construction firm that began by building and renovating medical facilities for the Department of Veterans Affairs and has since expanded into other federal, healthcare, commercial, industrial, and education work.

As a former U.S. Army infantry captain, Michael was recalled to active duty in 2006 and deployed to Southern Afghanistan, where he commanded an Afghan National Army rifle company during combat operations. He was wounded in action and was awarded the Purple Heart and two Bronze Stars for Valor.

After returning home, Michael launched Blue Cord during the recession and built the company around a mission of serving veterans and creating opportunities for those transitioning into civilian careers. He later founded the Florida Association of Veteran-Owned Businesses and co-founded the Camaraderie Foundation, which provides mental-health counseling and support to service members, veterans, and their families.

Website: ⁠https://blue-cord.com⁠

Camaraderie Foundation: ⁠https://www.camaraderiefoundation.org...⁠

ABOUT BUILT2WIN

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Built2Win is where the ones who build the world come to think bigger, lead better, and win at a higher level - long-form conversations on leadership, construction, and building something that lasts. Hosted by Chris Coghlan.

The best job FINFROCK ever lost ended up being the one that gave the company time to rethink how parking garages should be built. What followed was a decades-long transition from precast concrete subcontractor to a fully integrated design-build firm.

Chris Coghlan sits down with Bill Finfrock, president of FINFROCK, to discuss moving up the construction value chain — from manufacturing pieces of the building to taking responsibility for its design, engineering and construction.

From his early days estimating projects, to FINFROCK developing and building its own hotel to prove a structural system the market hadn’t yet embraced, Bill breaks down how a company founded in 1945 transformed the way it delivers buildings.

Bill also discusses the risk of leaving one business model before the next is guaranteed to work, why controlling more of the construction process can create better outcomes, and what it takes to bet your own resources on an idea the market hasn’t proven yet.

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⏰ CHAPTERS

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0:00 Intro

0:27 1945 → today: sand piles, golf carts, and an 83-year-old chairman

3:53 Lessons from Dad: hard work, candor, "nobody owes you anything"

6:23 A 24-year-old estimator and plans with more questions than answers

10:45 The best job we ever lost

13:13 The voicemail: 14 parking garages on one piece of paper

15:58 Curiosity as the operating system — "knowledge is economic power"

21:18 Foot out of one boat: the 15-year transition

26:11 "You're not a contractor" — refusing the lane

29:09 One of one: why nobody else does this

33:28 Bringing 40 architects in-house

38:15 Design-build removes excuses: "Guess whose fault it is?"

38:55 The internship plant test

40:42 Inventing the DualDeck: 10 years, 10,000 blind alleys

44:44 "How the hell am I going to sell the first one?"

46:12 The entire balance sheet: a $50M hotel in Naples

50:59 One year to the day: financing to open

53:23 Two Cat 4 hurricanes, zero damage

54:54 Lasers on the ceiling: why FINFROCK builds tech in-house

57:19 The AI panic: "complete nonsense"

1:02:34 The old prison that became a 100-acre plant

1:06:12 How he sizes a bet-the-company risk

1:09:18 "I'm competing against a spreadsheet"

1:13:24 #1 career advice: bring what they didn't ask for

1:17:17 It's five pm and everybody's walking out the door

1:18:20 What he'd change for the next generation

1:21:20 What he's most grateful for

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ABOUT THE GUEST

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Bill Finfrock is president of FINFROCK, the Apopka, Florida design-build contractor founded in 1945. FINFROCK engineers, manufactures, and builds its own structures under one contract. Bill joined full time in 1993, when the company had 88 employees and worked only as a precast subcontractor; it now has more than 700. Over the following fifteen years he helped move it up the value chain to become a design-build general contractor.

FINFROCK now builds parking structures, hotels, multifamily, office and student housing across Florida from plants in Apopka and Belle Glade.

Website: https://finfrock.com

Five straight All-Pro seasons ended on one Monday night hit in December 1987. The nerve never regenerated. Four years later Dwight Stephenson started a construction company with his wife, and stocked the drywall himself.

Chris Coghlan sits down with Pro Football Hall of Fame center Dwight Stephenson, co-founder of D. Stephenson Construction, to discuss what transfers from a locker room run by Bear Bryant and Don Shula to a job site — and what doesn't.

From his father working two jobs for 47 years to a first contract that took the company from zero to 200 people in a month, Dwight lays out the second career he built after the one he trained for was taken away.

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CHAPTERS ⏰

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00:00 Intro — NFL Hall of Famer Dwight Stephenson

00:38 One of seven kids: "You enjoy it, and you don't quit on it"

01:30 His father's two jobs — one hour off, for 47 years

02:36 Mom, seven kids, and a job by the fourth grade

04:16 Setting the standard — how Alabama found a two-year player

06:40 Mama's rule: "You're not going to follow anybody anywhere"

07:26 Alone in Alabama with two years of football

09:12 From defense to center

11:05 The rule: go to the next level, humble yourself

14:34 Playing for Bear Bryant

15:58 Bryant's principles: "I help those who help themselves"

18:09 Draft day — the phone call from Don Shula

21:21 Bottom of the depth chart again: just learn the plays

24:10 Shula's mental-error board: "Don't beat yourself"

26:22 What both legends shared: the CEO, not your buddy

28:34 The Dan Marino broken-finger story

33:59 December '87 — the Monday night injury

36:23 The nerve never came back

39:42 "Bring your playbook" — released from his dream job

41:38 Tears in the car — and choosing gratitude

43:35 Finding out he made the Hall of Fame at a gas station

45:35 His sister — the real leader of the family

47:49 The Dwight Stephenson Award

48:33 Starting over: "I'm gonna learn it from the ground up"

51:19 Christmas Eve drywall at the airport — why he loves hard jobs

53:31 Founding D. Stephenson Construction (January 1992)

54:48 Coaching for the man who released him

56:12 Building a company with his wife

59:32 Hurricane Andrew and Waste Management: 0 to 200 employees

1:00:38 What transfers from center to CEO

1:01:58 The skill he had to level up: people

1:06:07 "None of us are undefeated" — repairing a correction gone wrong

1:10:17 Elite vs. average: humble yourself

1:12:04 Advice to the young tradesperson

1:14:17 Why construction — money, pride, and work you can drive past

1:16:57 The Dwight Stephenson Foundation: computers for kids

1:20:44 What he's most grateful for

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POWERED BY OUR SPONSORS

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Big League Construction Supply ▶ https://linktw.in/NIMVjE

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ABOUT THE GUEST

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Dwight Stephenson is a Pro Football Hall of Famer and co-founder of D. Stephenson Construction, the South Florida construction firm he launched with his wife, Dinah, in 1992. Before entering construction, Stephenson spent eight seasons at center for the Miami Dolphins under Don Shula, earning five consecutive Pro Bowl selections and All-Pro honors from 1983 through 1987. At Alabama, he played under Bear Bryant and was part of back-to-back national championship teams in 1978 and 1979. Bryant called him the best center he ever coached and “a man among children.” Pro Football Hall of Fame

A severe left knee injury suffered during the 1987 season ultimately ended his NFL career. After football, Stephenson transitioned into construction from the ground up before he and Dinah founded D. Stephenson Construction, which now provides construction management, general contracting, program management and design-build services throughout South Florida.

Website: https://www.dstephenson.com

An estimator took the roads off on the wrong scale — a $1 million bust in asphalt and rock. Wal-Rose Site Development ate it, finished the job, and told the builder at the final walkthrough.

Chris Coghlan sits down with Jeremy Griffin, VP and third-generation owner of Walrose Site Development, to discuss how a Central Florida dirt contractor became a 300-person full-site-package company — and what it costs to be the one who tells the truth about a bad bid.

From cutting two fiber optic lines in his first week on a machine to developing 980 lots in 16 months, Jeremy lays out how Wal-Rose went from his dad and a handful of guys to 20+ pipe crews and over 300 pieces of iron.

If you run a site work, utility or dirt shop and you're deciding what to self-perform, when to RPO a machine, and how to build a superintendent bench instead of hiring one — this one is for you.

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⏰ CHAPTERS

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00:00 Intro: third-generation site developer

00:45 Growing up in the business: OJT & baseball

04:07 From ballplayer to the family business

04:52 The genesis of Wal-Rose (1994–95)

07:37 Why they went to a full site package

09:20 Starting in the ditch: "I ripped out two fiber optics"

11:20 300+ people, and never missing a schedule

14:15 Mom, dad, and how the family decides

17:57 Dad's lesson: your word. Mom's lesson: faith

19:04 Jeremy's North Star

20:04 How he keeps getting better

22:06 Recovery and a day in the life: up at five thirty

25:05 Promote from within: pipe layer to superintendent

27:46 Jackets, vacations, and Rolexes

29:25 Advice to foremen: show up, own it

30:32 "I was right, but I said too much"

34:58 The first job he owned

35:44 The job he's proudest of: nearly 1,000 lots in 16 months

36:40 What people overlook about site development

38:09 Who they build for: the national builders

39:31 The $1M estimating bust — and what the builder did

44:08 2008–09: nobody got fired

45:15 Equipment strategy: RPO, backlog, and turns

49:27 Hiring and what he looks for

51:16 Culture and values at Wal-Rose

53:13 Great vs. average superintendents

58:06 Safety that owns itself

1:00:16 Reading the 2026 market

1:04:29 Keeping the team from cracking under pressure

1:05:38 The Christmas party and the ice sculptures

1:07:02 Advice to the next gen: "AI can't lay pipe"

1:10:05 One thing he'd change in the industry

1:11:52 Gratitude and close

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POWERED BY OUR SPONSORS

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ABOUT THE GUEST

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Jeremy Griffin is vice president and part of the family leadership behind Wal-Rose Site Development, a Central Florida site contractor founded by his family in the mid-1990s. Today, Jeremy and his brother Josh help lead an operation with hundreds of employees and an extensive fleet of heavy equipment, performing site development work for major residential and commercial projects throughout Florida.

Jeremy’s path through the company started in the field. He began as a laborer working in the ditch, eventually became a pipe foreman, and later earned his underground utility contractor license — helping Wal-Rose bring utility work in-house rather than subcontracting it. Today, the company fields pipe crews, dirt crews, surveyors, mechanics and other self-perform capabilities across its site-development operation.

Website: https://www.walrose.com

He watched the Pentagon burn from a rooftop three miles away and saw a fighter jet come out of nowhere to turn back a news helicopter. Hensel Phelps would go on to renovate Wedges 2 through 5 of the Pentagon — a 4.5-million-square-foot project that took more than a decade to complete.

Chris Coghlan sits down with Matt Krystolic, operations manager at Hensel Phelps, to discuss nearly 30 years with one employee-owned construction company — and what it actually takes to work your way from field engineer to company stockholder.

From counting Pentagon windows by hand to helping lead major projects at Orlando International Airport and Universal’s Epic Universe, Matt breaks down the career behind the projects — and how a company founded in Greeley, Colorado, in 1937 eventually transitioned to employee ownership.

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⏰ CHAPTERS

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0:00 — Trailer: 9/11, the Pentagon, and 28 years at one company

1:00 — Mowing lawns at 14: where the work ethic started

3:16 — Family, football, and an Ohio State dad

4:33 — Choosing Colorado State over Ohio State

5:48 — Rugby and the regimen that carried him

7:40 — First taste of construction in the Rockies

9:12 — Getting hired at Hensel Phelps (five offers, good cop/bad cop)

14:27 — The Hensel Phelps origin story (1937, Greeley, CO)

15:05 — Employee ownership: how the ESOP actually works

17:16 — The Joseph Phelps wine connection

24:46 — 5,000 employees and a coast-to-coast career

26:49 — First job: NC State's arena, seven days a week

32:30 — "Do the right thing, get it open, then negotiate"

35:42 — Doubt, the ditch, and the move into estimating

37:26 — Why relationships are the real skill

41:00 — Virginia, and counting every window of the Pentagon

48:00 — 9/11: three miles from the Pentagon

52:43 — Five years rebuilding the Pentagon

58:28 — Florida, the Space Coast & Orlando's Terminal C

1:05:53 — The promotion that didn't come

1:14:03 — Christine: "the executive of everything that matters to me"

1:22:50 — Inside bidding the toughest clients — and the "snakes in the grass"

1:25:40 — Why the last mile is the hardest

1:27:38 — What construction really means: "you're building gold"

1:29:16 — Advice to the next generation of builders

1:33:19 — Elite vs. average: the mindset you can't teach

1:34:21 — The one thing he'd change: safety

1:35:46 — ABC Central Florida & the Robe Walk

1:39:44 — What he's most grateful for

1:41:05 — Closing: the next generation of builders

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ABOUT THE GUEST

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Matt Krstolic is an operations manager at Hensel Phelps, the employee-owned construction firm founded in Greeley, Colorado, in 1937 which employs nearly 5,000 people. He joined the company after studying construction management at Colorado State University and has spent nearly three decades building across markets including Raleigh, Washington, D.C., and Florida.

His career has included five years working on the Pentagon renovation and leadership roles on major Central Florida projects, including Orlando International Airport’s Terminal C and work at Universal’s Epic Universe. He also serves on the board of directors for Associated Builders and Contractors’ Central Florida chapter.

Website: https://www.henselphelps.com

Sixth-round pick. Oakland A’s. 1996. Nick Sosa made it as far as Double-A before baseball ended and he had to start over. Today, he’s a vice president with Kiewit Infrastructure, part of one of North America’s largest construction and engineering organizations — a company where employee ownership isn’t automatic. You earn the opportunity to buy in.

Chris Coghlan sits down with Nick to talk about the transition from professional baseball to heavy civil construction and what it takes to build a career inside a company whose roots go back to 1884.

From starting over as a rod man on a South Florida bascule bridge to helping deliver major infrastructure work at Orlando International Airport’s Terminal C, Nick explains why building the full tool belt matters more than rushing toward the next title.

He also gets into how Kiewit decides which jobs to pursue, how leaders know when someone is ready for more responsibility, what employee ownership actually means, and how to lead crews filled with people who may know far more about the work than you do.

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⏰ CHAPTERS

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0:00 Cold Open

1:04 Welcome Nick Sosa

1:17 Growing Up Around Heavy Civil Construction

4:23 Baseball, Sports & Getting Drafted by the A's

9:47 Pro Ball: From Best in Town to Mediocre

14:32 The Sound of a Different Level

15:20 Getting Released from Pro Baseball

19:30 The Pivot Into Construction

21:50 Starting at the Bottom: Rod Man to Builder

25:15 A Title Doesn't Make You the Boss

30:03 Finding Kiewit Through ENR Magazine

34:16 What Kiewit Actually Is

39:13 Employee Ownership & Skin in the Game

45:06 Kiewit's Origin, Omaha & Warren Buffett

47:04 Mission: Best, Not Biggest

49:23 Stewardship & Developing People

51:40 No End Goal: How the Opportunities Came

53:05 Coaching the Full Tool Belt

58:23 Big Company, Small-Contractor Feel

1:00:33 MCO & Building Terminal C

1:05:13 The People Who Built Nick

1:06:40 First Time You're "the Guy" & Managing Chaos

1:10:10 The Bad Job: The Army Corps Lesson

1:13:14 Health, Work-Life Balance & Performance

1:19:56 Doing Hard Things: Elk Hunting & Failure

1:24:47 Why Join Construction Now

1:27:23 What Construction Means to Him

1:28:20 Advice to the Next Generation

1:32:27 Training & Kiewit University

1:36:06 Gratitude & Close

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ABOUT THE GUEST

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Nick Sosa is a vice president at Kiewit Infrastructure, running the Southeast district — Baltimore to Mississippi and Florida, 300-plus staff. Drafted by the Oakland A's in the sixth round in 1996, he came out of pro baseball onto his father's bridge crews as a rod man. He joined Kiewit twenty years ago by answering an online job posting, has been a shareholder for over a decade, and helped build the company's Central Florida presence through Terminal C.

Website: https://www.kiewit.com

His wife was six months pregnant with their first child when he quit a good job to start on his own. "I was scared of failing — but the fear of not trying was bigger."

Chris Coghlan sits down with Junior Davis, founder of Junior Davis Construction, to discuss going from a worn-out 1973 loader and a used dump truck to 1,700 people and a billion dollars in backlog — without ever leaving ten Florida counties.

From parking equipment and building fences during a downturn to trading nights of wrenching on cars for repairs to his machines, Junior breaks down four decades of self-performing heavy civil work — and the culture he credits for making it work

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⏰ CHAPTERS

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00:00 Cold Open: Fear of Failing vs. Fear of Not Trying

01:17 From Zero to $1B Backlog in 10 Counties

02:13 First Construction Job: Mixing Mud and Tying Steel in High School

04:58 Why He Picked Civil Engineering as His College Major

06:41 The Coaches and Parents Who Shaped His Work Ethic

08:38 Ring Power Cat Sponsor Break

09:51 Betting on Himself: Quitting a Great Job with a Pregnant Wife

13:20 "You Don't Need a Partner — His Name is Jesus"

16:25 Buying His First Cat 930 Loader and Beat-Up Dump Truck

18:32 Clearing Lots and Knocking Doors: The First JDC Jobs

19:48 The 110% Commitment That Built Junior Davis Construction

21:43 Survival Mode: The Only Goal in the First Five Years

22:20 White-Knuckle Years: Building Fence to Keep the Lights On

26:01 Hiring His First Employee and Getting His Contractor's License

28:47 Getting Burned: Learning Florida Lien Law the Hard Way

31:09 How He Thinks About Risk on Big Contracts

33:47 Johnson & Co. Sponsor Break

35:21 Building a Family Culture: Why He Started When His Crews Started

38:55 The Standard: Quality Over Margin, Every Job, Every Time

41:47 9/11 and the National Day of Prayer That Changed JDC

44:39 Thanksgiving and Easter Services: Faith Inside the Company

47:00 Baptisms in the Shop: A Horse Trough and a Stage

50:31 Handing the Company to His Son Steve: "The University of JDC"

53:10 Earning Respect: Why Steve Started on a Shovel

56:33 What Steve Taught Junior About Patience and People

57:44 What Makes Him Most Proud of His People

58:19 1,700 People, $1B Backlog, 10 Counties — Did He Ever Envision This?

1:00:18 Focus on Effort, Not Results: The Anti-Goal Philosophy

1:01:23 Avoiding Complacency After Success

1:02:07 What Gets a Founder Out of Bed After 40 Years

1:03:54 Delegation vs. Control: Keeping a Finger on the Pulse

1:06:10 Why JDC Self-Performs and Stays Diverse Across Markets

1:08:21 Owning vs. Renting Equipment: The Utilization Rule

1:11:36 The Leadership Shift: Creating an Environment for Creative Thinking

1:14:49 Lead With Questions, Not Answers

1:16:20 What the Construction Industry Means to Him

1:17:08 What He Would Change About His 40-Year Journey

1:19:41 Why Most Construction Companies Don't Make It

1:22:12 Why Florida is the Best State to Build In

1:22:48 Advice for the Next Generation Getting Into Construction

1:23:39 Fix This One Thing: Permitting, Bureaucracy, and Modified Design-Build

1:29:28 What He's Most Grateful For

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Junior's Website: https://jr-davis.com