The construction industry has no shortage of people who will tell you how to build a project. What is harder to find are founders who will tell you, honestly, how they built themselves into a leader worth following.
In an episode of Built With Purpose, TrebleHook Founder and CEO Chris Fay sat down with Tony Iannessa, Founder and CEO of BIG Construction out of Chicago. BIG is a commercial general contractor that has been operating for nearly nine years, specializing in interior construction across Chicago’s central business district. What started as a raw conversation between two founders navigating a soft Q1 turned into one of the more candid leadership discussions you will find in the AEC space.
Here are the big takeaways.
A Strength Overused Becomes a Weakness
Tony did not arrive at nine years of leading BIG Construction without a few hard lessons along the way. He started at 31 with, as he describes it, a dangerous combination of drive and naivety. In the early days, that combination was exactly what the business needed. But somewhere around year five or six, the same qualities that built the company started to slow it down.
“That put it on my back, entrepreneur, founder, scrappy mentality works up to a point,” Tony said. “But it is not scalable. It is exhausting both for you and the people around you.”
The turning point came after losing two senior leaders in succession. Tony had to ask himself an uncomfortable question: what is the common theme here? The answer was him. Not in a self-defeating way, but in a clarifying one. The brute force style that got BIG to year eight was not going to get it to year eighteen. Something had to change.
This is a pattern that Chris knows firsthand. “I used to believe everybody should run at the same pace and be wired the same way,” he said. “But my team was still trying to implement the first thing while I was already three moves ahead.”
For AEC leaders, this tension is almost universal. The founders who built the company through sheer force of will often struggle most with learning how to lead through others. Recognizing it is the first step. Acting on it is the harder one.
Vision Without Execution Is Hallucination
Tony built BIG without a true integrator for years. He was the visionary, the seller, the driver. But without someone to translate that vision into a tactical plan that the team could actually execute, the business was running on willpower alone.
In 2023, he made a move that was both logical and emotionally difficult: he hired a president, Chris Farrington, to sit in the integrator seat.
“When I had two final candidates, I chose the one whose personality was almost the opposite of mine,” Tony said. “I knew him as a good, kind, humble, hungry, smart human being. That made the decision easier.”
The 30-60-90 day onboarding plan Tony put in place is worth noting on its own. The first 30 days, Farrington’s only deliverable was to sit down one-on-one with every single employee. Not to change anything. Not to suggest anything. Just to listen. By the time he was ready to propose changes at day 90, he had earned the trust of the people those changes would affect.
“The last thing you want is someone coming in and saying ‘we’re going to change this process’ when three people at the table built that process,” Tony said.
Thirteen months in, Tony describes the impact as hard to put into words.
Psychological Safety Has to Be Earned, Not Announced
Both Chris and Tony have wrestled with how to build a leadership culture where people will actually push back on the founder. The answer is not a policy. It is a pattern of behavior, consistently reinforced.
Chris shared that one of the most important things he did for his leadership team was give them explicit permission to challenge him. But as he put it, the first few times he told them, nobody believed it.
“They just said yeah, whatever, tell me what to do,” Chris said. “So when someone finally did push back, I stopped and said: you just pushed back on me. That is exactly what I need you to do.”
That is how psychological safety gets built in practice. Not through a single conversation, but through repeatedly showing the team that honesty is rewarded and dissent is welcomed. Tony described a similar approach, framing new ideas as something to attack rather than accept. “Poke holes in this,” he tells his team. It is not always comfortable, but it is how you surface blind spots before they become problems.
Running EOS All the Way Down the Organization
BIG has been running the Entrepreneurial Operating System since 2018, and Tony is candid about the mistakes he made along the way. They self-implemented without an integrator in the seat, which meant they got some of the value of EOS but not all of it.
The shift that has made the biggest difference recently is pushing EOS down past the senior leadership team. Today, project managers and superintendents are running on the same system, using the same language, tracking the same kind of metrics.
“To overhear people in our company talking about rocks, scorecards, progress not perfection, it is just super cool,” Tony said. “I wish I had pushed it down sooner.”
Chris echoed this from TrebleHook’s own experience running Rhythm, a similar operating system. Once the shared language gets into the organization, decision-making gets faster. Priorities become visible. Teams stop waiting to be told what matters and start navigating toward it on their own.
The Workforce Problem Is a Marketing Problem
One of the most urgent issues Tony brought up has nothing to do with the economy or material costs. It is the growing gap between the number of people entering the trades and the number retiring out.
“For every one person joining the trades today, three are retiring,” Tony said. “We have created a society where working in construction is viewed as a fallback.”
His take is that the industry has done a poor job telling its own story. The economics alone make a compelling case: a construction apprenticeship can put a 22-year-old into a $120,000 annual income, debt-free, with a tangible skill that benefits society. Compare that to a four-year degree that costs $250,000 and leads to an entry-level role at $75,000. The math is not close.
The problem is not the path. The problem is the narrative around the path.
Tony has made changing that narrative a personal mission, using his platform on social media to challenge what he calls the higher educational industrial complex and reframe construction as a legitimate, lucrative, professionally rewarding career. He also pointed to tearthepaperceiling.org as a growing movement with similar goals.
Chris connected this to manufacturing as well. The underlying issue is the same: industries built on skilled physical labor have undersold themselves for decades. The jobs have not changed nearly as much as the perception of them has.
Look Down the Mountain, Not Just Up
Tony closed the conversation with a thought from the book The Gap and the Gain, and it is the kind of thing that tends to hit founders hard.
The gap is the distance between where you are and where you are trying to go. The gain is the distance between where you are and where you started. Most driven leaders live in the gap. They are always measuring themselves against the horizon, which by definition they will never reach.
“If I had told myself nine years ago I would be here today, how cool would I have felt?” Tony said. “Instead I am always focused on the next nine years.”
Chris framed it simply: having people remind you of what you have actually built tends to make the horizon feel less impossible. Looking backwards with gratitude for what you have overcome does not mean losing sight of what is next. It means you are building from a foundation of something real, not just running from something incomplete.
The Bottom Line
The AEC industry has plenty of operators. It has fewer leaders who are willing to examine the gap between what they preach and how they actually show up for their teams. Tony Iannessa is one of those leaders, and this conversation is worth the time for anyone running a firm in this industry.
The themes here, scaling through others, building a culture of honest feedback, spreading your operating system into the organization, telling a better story about the trades, are not theoretical. They are the work. And they are exactly the kind of conversations that the Built With Purpose podcast was created to have.
Built With Purpose is hosted by Chris Fay, Founder and CEO of TrebleHook. New episodes feature leaders and executives from across the architecture, engineering, construction, and manufacturing industries. Follow along at www.builtwithpurposepodcast.com.