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Devin: What is your superpower?
Justin: I see possibility where other people see limitations.
Some entrepreneurs see a difficult problem and start looking for an easier one. Justin Smith does the opposite.
The co-founder and CEO of Contractor+ told me that the bigger and more difficult a problem becomes, the more attracted he is to solving it. That mindset has shaped both his company and his approach to entrepreneurship.
Contractor+ grew out of Justin’s own experience running a handyman business. He began building software to solve the bottlenecks he was experiencing himself. Years later, those solutions became a platform serving small business operators and trade contractors.
The need is substantial. Small contractors often struggle with contracts, change orders, estimates, payments and other administrative processes. Contractor+ has built tools to automate much of that work. Its Estimatic AI, for example, can reduce an estimating process that once took hours to about five minutes.
Justin knows those problems personally.
He recalled having a foreman return from several daily estimates with handwritten notes, photos and rough calculations. Justin would then spend hours turning those estimates into finished proposals. Sometimes he was still working on them at 2 a.m.
That experience became part of the motivation for building something better.
But Justin’s entrepreneurial journey has also included profound personal hardship. After spending about six years in the prison system, he said he came to understand that money was not the definition of success he once thought it was.
“What makes me happy is creating value,” Justin told me.
That lesson now seems deeply connected to his business philosophy. He described his ambition as creating “real value that impacts other people’s lives.”
That purpose also shaped how Contractor+ has raised capital. After speaking with 126 investors, Justin turned to the crowd. He saw an opportunity to let customers and others who believed in the company participate in its future.
The company has raised capital through Wefunder in multiple rounds and, as Justin explained, has been exclusively funded by the crowd.
For me, the most compelling lesson from this episode is that limitations do not always have to remain limitations. Sometimes they reveal the opportunity.
Justin put it simply: “I see possibility where other people see limitations.”
That is more than an entrepreneurial philosophy. It is a useful way to approach difficult problems. The obstacle in front of us may contain the clue to what we should build next.
tl;dr:
Justin built Contractor+ from firsthand experience solving operational problems he encountered while running a contracting business.
Contractor+ helps small contractors streamline contracts, change orders, payments and estimates through increasingly automated technology.
Justin’s personal hardships reshaped his definition of success, shifting his focus from pursuing money toward creating meaningful value.
After 126 investor conversations, Justin found a community-powered path to funding Contractor+, bringing customers and supporters into the company’s growth.
Justin’s superpower is seeing possibility where others see limitations, then persisting until difficult challenges become opportunities.
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How to Develop Seeing Possibility As a Superpower
Justin’s superpower is seeing possibility. He explained it this way: “I see possibility where other people see limitations.” He is naturally drawn to problems that seem too large or difficult for others to tackle. Rather than being discouraged by the size of a challenge, he becomes more interested in solving it. He also connects this ability with persistence, saying, “the one thing for sure is that I persist where a lot of people would give up. I persist.”
One of the clearest examples came from Contractor+’s fundraising journey. Justin had spoken with 126 investors while trying to find traditional investment. Rather than treating repeated rejection as evidence that the company could not raise capital, he looked for another possibility. He realized that the people who actually benefited from Contractor+ could become investors themselves. He pivoted toward community funding, put substantial time and energy into the effort and successfully raised capital from the crowd.
Another example involved technology certifications. Contractor+ spent six months building technology only to discover that it could not ship without the necessary certification. Instead of treating that requirement as the end of the road, Justin pushed through it. The certification ultimately became an asset, helping create a stronger product and valuable relationships with Google.
How To Develop The Superpower
Care deeply about the problem. Justin’s strongest advice was to make sure you genuinely care about what you are building and the problem you are trying to solve.
Focus on the outcome. When you care about the outcome, obstacles become easier to confront rather than reasons to quit.
Look at limitations differently. When you encounter a barrier, ask what opportunity might exist on the other side of it.
Persist when others stop. Justin repeatedly emphasized persistence. Continuing through difficulty can create opportunities that are invisible at first.
Get outside your comfort zone. Justin connected difficult challenges with growth, noting that possibilities can become greater after being forced through demanding situations.
Serve the people who benefit. His fundraising experience suggests looking closely at who genuinely values the solution. Those people may become important supporters and participants in the journey.
By following Justin’s example and advice, you can make seeing possibility a skill. With practice and effort, you could make it a superpower that enables you to do more good in the world.
Remember, however, that research into success suggests that building on your own superpowers is more important than creating new ones or overcoming weaknesses. You do you!
Guest Profile
Justin Smith (he/him):
CEO, Contractor+
About Contractor+: Contractor+ is an all-in-one business operating system built to revolutionize the way contractors run, manage, and grow their businesses. By bringing together customer relationship management, estimating, invoicing, payments, project management, scheduling, and AI-powered automation into one platform, Contractor+ eliminates the fragmented, outdated systems that hold millions of hardworking tradespeople back. Our mission is simple: empower the people who build and maintain the world with the same powerful technology and competitive advantages traditionally reserved for large enterprises. We’re not just building software. We’re building the digital infrastructure for the next generation of construction and field service businesses, creating a connected ecosystem where contractors, subcontractors, suppliers, and property owners can work together seamlessly.
Website: contractorplus.app
X/Twitter Handle: @cplusapp
Company Facebook Page: facebook.com/contractorplus.app
Other URL: wefunder.com/contractor
Biographical Information: Justin Smith is a serial entrepreneur, bestselling author, and Co-Founder and CEO of Contractor+, a rapidly growing technology company on a mission to transform the construction and field service industries. A builder and problem solver at heart, Justin has dedicated his entrepreneurial career to challenging outdated business models, identifying overlooked opportunities, and creating technology that levels the playing field for small businesses. Under his leadership, Contractor+ has evolved into a comprehensive, AI-powered operating system serving thousands of paying customers and generating approximately $1 million in annualized revenue. But Justin’s ambitions extend far beyond building another successful software company. He envisions a future where independent contractors have access to intelligent automation, powerful business tools, and a connected marketplace that allows them to compete with much larger organizations. Driven by a deep belief in entrepreneurship, individual freedom, and the transformative power of technology, Justin is determined to help the people who build our communities build extraordinary businesses of their own.
Personal X/Twitter: @justinonsuccess
Personal Facebook Profile: facebook.com/justinbriansmith
LinkedIn: linkedIn.com/in/justinbriansmith
Instagram: @justinonsuccess
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