How Personal Brand Builds Business Reputation

We had six businesses fail. And one of them failed in such a big way, I had to sell everything I had.

That stark admission from Matthew Stewart—co‑founder of College Works Painting—sets the tone for an interview that cuts past buzzwords and into the real work of leadership.

• Your Values Are Already Building or Breaking Your Brand
• Feedback: The Toughest Mentor in the Room
• Customers Spark New Ventures When You’re Listening
• Leading Through a Generational Shift
• What Founders Need to Hear But Rarely Do
• Uncertainty Is the New Constant

Watch the full interview:

Your Values Are Already Building or Breaking Your Brand

Matthew is quick to shrug off the term personal brand, but he takes action the moment values and behavior drift apart. When high performers clashed with company culture, he didn’t hesitate:

We’ve gotten rid of our top people a few times because they didn’t fit in the culture.

That decision illustrates a larger principle: values are not a feel‑good poster on the wall; they are the rules that govern every hiring, firing, pricing, and product decision. In practice, this means:

Consistency beats charisma. A leader who makes decisions on the same principles every time is predictable, and predictability builds trust with employees and customers alike.

Values reduce costly mistakes. When profit is the only metric, short‑term gains can mask long‑term risk. A values lens highlights hidden costs—such as reputational damage, higher churn, and regulatory backlash—before they impact the P&L.

Purpose attracts top talent. Mission‑driven companies grow faster because high performers increasingly choose workplaces that reflect their beliefs. Stewart’s willingness to cut misaligned stars signals that the culture isn’t for sale.

By treating values as a daily decision filter, Matt flips the usual equation: culture drives profit, not the other way around. Staff and customers sense when that filter fails—and they leave. When it holds, they invest more deeply, creating a compounding advantage that pure price competition can’t match.

Feedback: The Toughest Mentor in the Room

Today, tracking and acting on customer reviews is not a hype cycle or a marketing fad—it’s a survival skill. Ignoring them can quietly drain revenue, talent, and trust long before the balance sheet shows red. Matt learned this firsthand: unchecked complaints pointed to deeper flaws in hiring, training, and communication.

Net Promoter Score surveys, mid‑project check‑ins, and public review audits now inform leadership meetings. Matt treats feedback as a diagnostic dashboard. Patterns in complaints reveal root‑cause issues—poor onboarding, gaps in communication, mismatched expectations—so the team can act before problems snowball into costly churn. Reviews are no longer a reputational threat; they’re an early‑warning system that links frontline performance directly to profit.

Customers Spark New Ventures When You’re Listening

When Listening Pays Off

A roofing client who also needed siding repairs sparked the creation of Home Genius, a one‑stop shop that bundles roofs, windows, doors, gutters, and siding under a single contract. The move kept homeowners from juggling subcontractors—and opened a new, high‑margin revenue stream for Stewart’s team.

When Rushing Backfires

But customer demand isn’t the same as strategic fit. Repeated requests to replace rotten wood before painting led College Works into a full wood‑replacement venture. Margins looked attractive, lead flow was automatic, and the venture flopped. Sub‑contracted crews slipped on quality, schedules exploded, and warranty claims ballooned until Stewart shut the division down.

Stewart’s Three‑Point Test for Expansion

• Capability match – Does the request align with existing strengths, systems, and talent?
• Control point – Can the company own the customer experience end‑to‑end, not just add labor?
• Compounding value – Will the new offer deepen loyalty or simply add operational drag?

Leading Through a Generational Shift

Stewart has managed crews and customers across three—and soon four—generations, watching expectations pivot from hierarchical loyalty to real‑time transparency.

Gen X: Earn Trust, Keep It Simple. This cohort valued expert opinion and a transparent chain of command. Policies were printed manuals, and feedback was provided annually.

Millennials: From Experts to Peers. Millennial employees shifted the trust anchor from “what the boss says” to “what my friends experienced.” Social proof—ranging from ratings and referrals to Glassdoor reviews and customer experience on the platform, such as PissedConsumer—now influences both hiring and purchasing decisions.

Gen Z: Pattern Spotters, Efficiency Hackers. Raised on TikTok filters and instant fact‑checks, Gen Z assumes any single review can be gamed. Instead, they scan patterns: review velocity, tone consistency, and response quality. If a company’s public persona doesn’t match its internal culture, they spot the gap quickly.

What It Means for Leaders

• Radical Consistency: Align public claims with everyday decisions; Gen Z will call your bluff in hours, not years.
• Transparent Feedback Loops: Publish how complaints are resolved, not just the star rating. Show the work behind the score.
• Tech‑Enabled Efficiency: These Gen Z employees automate repetitive tasks. Provide tools—or they’ll hack together their own.

What Founders Need to Hear But Rarely Do

Based on hard‑won experience, Matt’s advice boils down to four repeatable checks:

• Begin with the end in mind – Be crystal‑clear on where the venture should take you before spending the first dollar.
• Validate before you scale – Pilot relentlessly; only pour fuel on models that show traction in the real world.
• Respect the stop‑loss line – Set a point where you walk away and do not keep moving it.
• Double down on training – When cash gets tight, resist the urge to cut learning budgets; capability compounding is the cheapest growth engine you own.

Uncertainty Is the New Constant

Tariffs, supply shocks, and political divides now define the playing field. Stewart worries that most of his workforce has never seen a real downturn:

My employees have never known anything but prosperity. They’ve never seen a recession.

It has already brought a new challenge to American business leaders: almost everybody will have to stress‑test their values, finances, and supply chains now, before volatility does it for them.

The story comes full circle: the hard‑won lesson that once forced Matt to “sell everything I had” now fuels a leadership philosophy built to weather the next storm, whatever form it may take.

Watch the full interview with Matt Stewart on YouTube