What Robert Yuen’s journey from unemployed designer to venture-backed CEO teaches us about building stronger, more innovative architecture firms.
On this week’s episode of the EntreArchitect Podcast, I had the pleasure of sitting down once again with my good friend Robert Yuen, CEO and co-founder of Monograph. Robert’s story is not one of smooth, linear success. In fact, it begins with failure. He was fired from his job at a small San Francisco design firm just as he was about to begin his licensure exams.
From that low point, Robert has gone on to co-found Monograph, a project management platform built exclusively for architects and engineers. What started as a simple time-tracking tool has evolved into a venture-backed company serving thousands of firms, handling billions of dollars in fees, and raising over $40 million in capital along the way.
Most small firm architects will never raise millions from Silicon Valley investors. But the lessons Robert has learned along the way are deeply relevant to us. They’re lessons about failure, persistence, leadership, and valuing our own work.
Here are five powerful lessons from Robert’s journey that every small firm architect can apply to their own practice.
Listen to the full conversation at EntreArchitect.com/625.
Lesson 1: Failure Can Be the Beginning, Not the End
Robert’s career in architecture started like many of ours. He earned dual master’s degrees from the University of Michigan, worked at SOM, and eventually joined a boutique husband-and-wife practice in San Francisco. But while juggling his full-time role with his weekend passion for teaching and technology workshops, he simply couldn’t keep up. The firm let him go.
For someone highly competitive and driven, being fired was devastating. “I’ve never been let go before,” Robert shared. “It was a huge personal setback. Who am I? What am I going to be?”
But that painful moment became a turning point. Instead of retreating, Robert leaned into his passion project, Section Cut—a bookmarking platform and teaching vehicle he had built for himself and friends. It wasn’t a viable business, but it gave him a chance to experiment, to fail, and to learn.
I know this firsthand, because the very origins of my own architecture firm came from failure too. Annmarie and I left our jobs for a project that we believed would be our firm’s foundation. Then we were terminated without warning and without cause. At the time it felt like disaster, but that loss gave us room to accept a different commission—a home for a wonderful client—that opened the door to years of high-end residential projects. The work that grew from that unexpected turn became the true launchpad for our practice.
Failure hurts in the moment, but it often clears the space for opportunities we couldn’t see before.
For us as small firm architects, the lesson is clear. Failure is not the end of the road—it’s the start of a new one. The moments when we lose a client, stumble on a project, or face rejection are often the very moments that open new paths forward. The key is not to avoid failure but to extract the lesson it has to teach.
Lesson 2: Start Small, But Keep the Vision Open
Monograph didn’t launch as the robust project management platform it is today. The first version was far simpler: just time sheets.
Robert and his co-founders recognized that in architecture, everything comes back to time. Every fee proposal, every invoice, every measure of profitability is ultimately tied to how we spend and track our hours. So they started with the smallest possible tool that could address the problem: a clean, architect-friendly time-tracking app.
They were honest about what it did—and what it didn’t. It couldn’t manage projects or budgets yet. It was just a time sheet. But it was better than the spreadsheets most firms were using. And that was enough. Within a month, they had five paying customers.
At first, the vision was modest. “It was meant to be a lifestyle business,” Robert recalled. A side product to complement the agency work they were already doing. But when demand grew and more architects started knocking on their door, they realized this wasn’t just a side project. It could be much bigger.
This is a lesson every architect can apply: start small, but leave room for growth. Don’t wait to build the perfect system or launch the ultimate service. Solve one problem well. Deliver real value. Let that momentum carry you to the next step.
For your firm, that might mean refining one service, documenting one process, or experimenting with one new offering. Don’t be afraid to start small—but also don’t limit your vision to staying small.
Lesson 3: Rejection is Data, Not Defeat
When Monograph gained traction, Robert knew they needed outside funding. The math was simple: with three co-founders and one employee, they needed about $400,000 a year just to cover salaries. Their pricing model at the time would never get them there fast enough.
The problem? Robert didn’t have wealthy friends or family to back him. His parents were immigrants, and his network was almost entirely architects. So he went the hard route: cold calls, cold emails, and LinkedIn messages.
For three months, he heard nothing but “no.” In total, 120 investors turned him down.
But Robert didn’t treat those rejections as dead ends. After each “no,” he asked why. What made them decide against investing? What could he have explained better? What didn’t they believe? Then he went back to the pitch, adjusted, and tried again.
By the time the first investor finally said yes, Robert had refined his story so well that eight more quickly followed. Monograph closed a $2 million seed round.
For us, the lesson is obvious. Every time we present a proposal, we risk rejection. Every time we chase a client who doesn’t sign, it feels personal. But like Robert, we can choose to see rejection not as defeat, but as data. Ask why. Look for the pattern. Adjust your approach.
Rejection is inevitable. Learning from it is optional.
Lesson 4: Leadership Requires Owning Your Mistakes
After a successful Series A round of $7 million, Monograph raised a massive $20 million Series B led by Tiger Global. Suddenly, the company had resources it had never dreamed of. The team grew quickly. Too quickly.
“It felt like you could never spend it all,” Robert admitted. “But we lost some of the financial discipline that’s required to run a business.”
When the numbers no longer made sense, Robert faced one of the hardest leadership decisions of his career: layoffs. “It wasn’t that they did anything wrong,” he reflected. “I made a mistake in hiring too fast, and I needed to correct it.”
For a young entrepreneur who prided himself on building a company people could call home, letting team members go was painful. But it was also transformative. Robert realized that leadership isn’t about never making mistakes. It’s about owning them, correcting them, and leading through them.
As architects, we lead teams too—whether that’s a handful of employees, a group of consultants, or a room full of clients. We will make mistakes. The question is whether we have the humility to own them and the courage to make the hard calls to fix them.
Leadership is not about being flawless. It’s about being accountable.
Lesson 5: Value Your Work—Raise Your Rates
At the end of our conversation, I asked Robert what single piece of advice he would give to small firm architects who want to build a better business. His answer was immediate:
“Don’t forget to raise your rates.”
It’s simple advice, but also the most overlooked. Many architects underprice themselves, afraid of losing the project or of being compared to the competition. But if your fees don’t reflect your value, you’re building your business on sand.
Raising your rates isn’t just about making more money. It’s about respecting your time, acknowledging your expertise, and creating the financial foundation that allows your firm to thrive. Without the right pricing, you’ll never have the capacity to invest in your team, take on the right projects, or build a sustainable practice.
Take a moment to review your current rates. Do they truly reflect the value you provide? If not, it’s time.
The Architect as Entrepreneur
Robert Yuen’s journey from being fired to building a $40 million venture-backed startup is extraordinary. But the lessons embedded in his story are universal:
- Failure can be a foundation.
- Start small, but think bigger.
- Rejection is data, not defeat.
- Leadership requires accountability.
- And yes—raise your rates.
You don’t need to be a tech founder to apply these lessons. Every small firm architect faces the same challenges of vision, persistence, leadership, and financial health.
Robert told me he feels like he’s still in “chapter one.” With nearly 100 employees and a roadmap to build an “operating system” for the entire building industry, Monograph has much more growing to do.
But even at this early stage, his story offers a roadmap for us as small firm owners. A roadmap not just for building startups, but for building better practices.
Listen to the full conversation at EntreArchitect.com/625.
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