About Sam

Sam Velasquez has walked away from two successful businesses. The third is Windy City Production — and after 14 years, he's more committed to it than he was at the start.

If that's a strange way to start an About page, stay with it for a minute. There's a reason.

The first walk-away was a master's degree in accounting from a top-10 business school, on track to become a CPA. He left it during the exam itself, after a couple asked him to fly to Costa Rica to capture their wedding.

The second was True Sounds Entertainment, the wedding DJ company he'd built and run for years, with over 100 personal reviews. He left it because the photo and video work he was doing on the side started outpacing it, and he refused to do either job at half attention.

Most people walk away from one thing in their lives. Sam has done it twice — at different stages, from different versions of success — and chosen wedding photography both times.

This page is about why.

The Pivot

In 2007, Sam founded True Sounds Entertainment while still in college. He was 20 years old.

The first wedding he DJ'd, around 2008, taught him painfully that he wasn't ready for weddings yet.

The bridal party was massive — a heavily Polish family with a long list of difficult last names. The couple had requested a unique song for every pair of names called. Sam was mixing on CDs. The intros went on. The dance floor that opened next, intended to start full-tilt, never filled — the crowd skewed older than the music suggested.

He left that wedding determined to never work another one.

What he did about it is the part that matters. Sam's instinct — then and now — has always been to take on more and figure it out as he goes. It's not the easy way. It's the way that requires you to fail, sometimes publicly, and then rebuild from the inside.

He pulled True Sounds out of the wedding industry entirely. He rebuilt around corporate events. Then private parties. Then engagement parties. Each step closer to weddings, but on his terms.

By the time he came back, he was a different DJ. The first wedding had taught him something most DJs spend a career not learning: the gap between what a couple asks for and what will actually serve their wedding day. That instinct — what to honor, what to gently redirect, what a room actually needs — is the same instinct that today, 18 years later, runs every Windy City Production wedding.

True Sounds eventually grew back into weddings, generating over 100 personal reviews. To differentiate it, Sam started capturing photo and video at the events he worked. The bridge to a real photo and video career came from an unlikely place: a Chicago engagement party. The couple had hired Sam to DJ but had also seen the side work, and they asked him to film the engagement party — knowing the actual wedding would be a small destination wedding in Mexico. Sam said yes.

That moment — saying yes to capturing more than he was contracted for — is the seed of everything Windy City Production has become.

By late 2011 or early 2012, Sam was sitting for the CPA exam. The master's was done. The scholarship had been earned (one of six tuition-waiver recipients at his school). The career path was in place.

A potential client reached out and asked if he'd fly to Costa Rica to photograph their wedding.

He said yes. He didn't go back to the exam.

Sam was contracted to capture the photos. He took on cinema too — same instinct as the engagement party, only bigger. That Costa Rica wedding was the first hybrid shoot of his career. The Hybrid offering Windy City Production runs today is its descendant.

The CPA path didn't formally end — and Sam will be the first to admit it bothers him a little. "Honestly, it still drives me nuts that I haven't fully completed it." He has the credit hours to sit any time. The same temperament that walks away from successful businesses also doesn't like leaving boxes unchecked.

A few years into Windy City Production's growth, he made the second hard decision: he shut down True Sounds entirely. Then, years later, a third version of the same decision — he pulled himself out of video, where couples specifically requested him for his same-day edits, and committed to photography. He had become known for one thing, and he chose to become great at another. The international rankings on his own work came after that decision, not before.

Three times — at three different stages — Sam has walked away from a successful version of his own work to do something harder. The pattern matters because it tells you what kind of person you'd be hiring.

The Cost

In 2023, on the Saturday before his first Ironman in Wisconsin, Sam shot the video for a Chicago wedding. He attempted a same-day edit during the reception. He couldn't finish it in time. He completed the Ironman the next morning, frustrated by the unfinished cut.

So in 2024, before his second Ironman, he took on more.

He shot a hybrid wedding — photo and cinema, both, alone. He stole 10-minute windows during the reception to build the same-day edit. He screened it for the couple before the night ended. He drove to Madison for three or four hours of sleep. He lined up at sunrise for a 140.6-mile triathlon — and finished 90 minutes faster than he had the year before.

Most photographers don't shoot weddings the day before an Ironman. Most photographers don't compete in Ironmans, period. Sam has finished three full Ironmans and two halfs.

That's not unusual for him. It's a slightly more extreme version of his normal week.

He has shot weddings days after each of his three children were born. He has shot on his anniversary, his birthday, New Year's Eve, Labor Day weekend, and the Fourth of July. The only holidays he hasn't worked are Christmas and Christmas Eve. In 14 years, he has never canceled a wedding — not after a surfing accident in Costa Rica that required stitches the night before, not for any reason.

The early years cost differently than the current ones. Sam's first wedding video package was $400. The Canon 5D — the camera he bought to take the work seriously — went on a credit card he wasn't sure he could pay off. "I just need one good opportunity with this camera on a wedding to change our future," he told Katie.

Then there was New York.

A couple Sam was contracted to photograph in South Florida wanted their engagement photos in New York City. He chartered a flight, landed in early spring, and got bombed by a snowstorm. Hotel rooms were not in the budget — every dollar was being poured back into the company. So Sam walked. All night. The only place open and warm was a 24-hour McDonald's in Times Square — even that had a sign capping how long you could sit. The next morning, exhausted, he slipped into a public library and laid his head on a table to grab a few minutes of sleep before the engagement shoot. A security guard tapped the table and woke him up. No sleeping in the library.

He shot the engagement session in soaked socks, took a shuttle to the airport, and fell asleep on a radiator. He says it was the best sleep he'd had in months.

The pattern of trips like that ran for years. To make destination weddings possible in South Florida and California, Sam and Katie became regulars at sleeping in cars in hospital parking lots. (Hospitals, it turns out, are the safest overnight option. They learned this from experience nobody asks about.) Travel toothpaste from Target. Public beach showers in Florida.

The harder version was a whole season at home.

In January 2015, Sam and Katie's furnace broke. Wedding season had ended in October. The math was simple — there was money for the studio or money for the furnace, but not both. They chose the studio. They went without heat for the rest of that winter, which turned out to be tied for the coldest February in Chicago history. The cold pushed them out of the house for longer hours at the studio, and the longer hours pushed the editing forward faster. The cold that should have hurt the business ended up making the work better.

The current cost looks different but is the same kind of cost. Climbing a mountain in Costa Rica until he found cell service for a phone call with a couple who hadn't even booked yet. Client meetings from Yellowstone, from the deserts of New Mexico and Arizona — sometimes thanks to Starlink, sometimes thanks to whatever ridge or ledge would hold a signal. Planning his life almost two years in advance because that's how far out couples book Sam directly.

Shooting weddings every weekend while raising three children. Workouts stolen from the edges of his calendar — early mornings before a wedding, or late nights after.

Couples don't usually see this part. Sam doesn't talk about it on consult calls. The reason it's on this page is because it's the thing most photographers won't pay — and the thing every couple should know they're getting when they hire him.

April 2020

On April 6, 2020, three weeks into the original COVID-19 stay-at-home order, with the entire wedding industry in free-fall and most vendors quietly hardening into non-refundable deposit policies to survive, Sam recorded a video for Windy City Production's 2020 couples.

The video did three things. It promised any couple forced to reschedule a refund of the deposit for any service WCP couldn't accommodate on the new date — a position most studios were not taking. It upgraded every 2020 wedding — Associate, Katie, and Sam packages — to include a free Romantics album, regardless of what each couple's contract specified. And it offered free business help — photography, video, web design, branding — to three past WCP clients who were small-business owners struggling in the shutdown.

Read that last one again. In the worst quarter the wedding industry had ever experienced, with the studio's own future uncertain, Sam volunteered free professional services to past clients he had no obligation to.

The videos are still on Windy City Production's YouTube channel. Anyone can watch them. That's the part that matters most: this wasn't said behind the scenes. It was said publicly, on tape, in real time, during a moment when most of the industry was retreating.

That instinct — give more, not less, when it costs you the most — is the same instinct that drives every WCP wedding day. It's not a marketing position. It's how the studio is run.

The Three Pillars

Three operating principles run Windy City Production. They've been the same since the beginning, and Sam has them written down — partly because writing things down keeps a person honest when the wedding season gets long.

Shoot like your life depends on it.

Every wedding day is unrepeatable. There is no second take on the first kiss. There is no rescheduled father-daughter moment if the light goes wrong. The shooter who treats a wedding like a job he'll do again next weekend is the shooter who misses the moments only experience teaches you to anticipate. Sam shoots every wedding like it's the only wedding — because for that couple, it is.

Relentlessly grow and refine your skillset.

This is the pillar that explains the three dismantlings. Sam has spent 14 years deliberately becoming uncomfortable. By his own associates' description, he's the strongest overall shooter on the Windy City Production team — and his honest opinion is that he might be wrong about everything next year, which is exactly the point.

He treats each year as a blank canvas. He does not coast on Windy City Production's Knot Hall of Fame designation, on his own WedAwards rankings (Internationally Ranked 2023, 2024, 7th Best Internationally 2025), or on 14 years of weddings. Couples who hire Sam are hiring the version of him still actively trying to get better at this.

Be the best at adding value.

This is the pillar most clients see directly. It explains the things Sam does that aren't in the contract.

He personally shoots the free pre-video sessions for every associate-tier couple who books video — even though the contract doesn't require it. He has personally shot the majority of Windy City Production's free mini sessions and Christmas shoots. When an associate-tier wedding sits on the studio calendar and Sam's schedule is open, he picks it up and shoots it himself. He is the editor on every Wedding Day Love Story Windy City Production has delivered for the past five years — every gallery, every cinema film, his hands, every time.

His own associates have a nickname for him. They call him the wizard — a reference to things they've watched him pull off on a wedding day they've never seen another shooter do.

That's not a line written for an About page. It's something his team came up with on their own.

The Mindset

Sam describes a wedding day like a chess board. You have to think three or four or five moves ahead to maximize the day. Bride's morning is light. Reception is timing. First look is timing and light and emotion all at once — two families, a coordinator, a bridal party, all moving through it together. The shooter who only sees the move in front of him misses the move that's coming.

The endurance side of Sam's life shows up here. The 40-day cross-country bike ride. Three full Ironmans, two halfs. The 10K open water swim. The ultramarathon in his history. Spearfishing in Baja. None of those things make him a better photographer in a technical sense. But they're physical proof that the same person who shows up to a wedding has spent years building tolerance for the long, painful, multi-step commitments that don't have shortcuts.

Wedding days don't have shortcuts either.

There's a posture in the wedding industry — Sam has watched it for 14 years now — where photographers reach a certain level of success and start coasting. "It's my way and this is how I've done it and this is how I'll always do it." Sam's instinct is the opposite. "I need to be humble. I need to be creative and open to the fact that I can be completely off on everything."

He looks at every year as a blank canvas. Not because the previous years didn't matter — but because the previous years aren't going to be the ones holding the camera at this couple's wedding.

Your wedding hasn't happened yet. That's the only thing that matters.

Couples who book Sam directly are booking the founder, the lead artist, the editor, the person whose name is on the brand, and the person whose decisions over 14 years have built every standard the company holds itself to. Katie shares the same standards. They co-founded Windy City Production and run it together — and Katie's About page is coming next, because her story deserves the same room this one got.