Catch up on our Understory Unfiltered episode where Robert Yuen shares how he went from sleeping on an office air mattress to building a 100-person SaaS company serving architects.
Robert Yuen, founder and CEO of Monograph, spent nine months sleeping on an office air mattress while building a SaaS company that now employs 100 people and has raised nearly $50 million. His journey from licensed architect to successful software founder reveals hard-won lessons about scaling teams and staying resilient.
Listen to this episode to learn why four-day work weeks collapse after 10 employees, Robert's three-tier mentorship framework for different growth stages, and how Monograph's AI contract scanning eliminates hours of manual project setup for architects.
Robert Yuen is the founder and CEO of Monograph, a project management, time tracking, invoicing, and payment platform built specifically for architects and engineers. After working as an architectural designer for 10 years, Robert started Monograph with two co-founders to solve the operational chaos he experienced firsthand in architecture firms.
Six years later, Monograph has grown to 100 employees with nearly $50 million in funding. Robert's path included running an EdTech side hustle teaching at universities, getting fired from his architecture job, and sleeping in the office for nine months during a difficult personal period. His immigrant family background and parents' entrepreneurial experience running Chinese restaurants shaped his resilience and work ethic.
[01:05] What Monograph does: project management, time tracking, invoicing, and payments for architects and engineers
[01:44] How Robert got fired from architecture while running a weekend EdTech side hustle teaching at universities
[04:08] The four-day work week experiment: why it worked under 10 people but broke at 30 employees
[06:27] Nine months on an air mattress: Robert's story of sleeping in the office and showering at the gym
[10:16] Robert's three-tier mentorship framework: tactical advisors, seasoned guides, and people to teach
[14:27] How clear role division with co-founders enabled early scaling and their amicable departure
[18:39] Robert's father swimming from China to Hong Kong: the immigrant story behind his resilience
[27:08] Monograph's AI contract scanning: upload a contract and the system extracts projects, timelines, and team assignments
Robert and his co-founders successfully ran Monograph on four-day work weeks until around 30 employees. "When the team is small, I say small, let's say 10 people or less and you have a really high density of incredible talent, all 10. Everyone is accountable for what they're doing and what they need to get accomplished. You don't need to count days," Robert explains.
The model collapsed as complexity grew. "The four days break very fast after 10 people. And we just didn't know. First time founders, first time entrepreneurs never built a scaling business of that pace. There's internal operational workflows that just start to break. And you need that fifth day."
As we discuss in the episode, this mirrors what we see with SaaS clients at Understory: operational frameworks that work at one stage create bottlenecks at the next. The lesson for growth leaders is to plan for the scale you're building toward, not the scale you're at today.
Robert's mentorship framework involves three distinct tiers that evolve as the business grows. "Try to find someone that's only like two steps ahead of you and that person will probably be an incredible mentor. Find someone who's really, really seasoned and that person is going to help you with your mental space, mental head space, mental clarity. And then have a lot of people that are actually a few steps behind you," he explains.
The teaching component clarifies strategic thinking: "If you have to explain what you do, how you do it to someone who hasn't been there yet, it is actually helping you reaffirm what's important." One early mentor's fundraising advice stuck with Robert: "You're a really nice guy. You work incredibly hard. You're never going to close a round if you stop being a nice guy." Being aggressive about timelines and direct about expectations proved essential for closing rounds.
Robert's ability to command rooms developed through repetition, not natural talent. "I think I have parts of it, maybe growing up and then it takes a lot of practice. It takes a lot of honing in and it takes a lot of self-awareness," he explains.
His practice ground is weekly all-hands meetings. "We still have weekly all hands. We don't make them monthly. So like, and I speak at all of them. Good days, bad days, good months, bad months. Like the team needs to hear from the leaders. So you get a lot of practice."
As we explore in the episode, founders often develop opposite skills naturally and must deliberately practice the gaps. Some leaders are born with authority and presence but need to learn softer communication skills. Others have natural empathy but must practice being direct and commanding. The key is identifying which skills require conscious development and creating regular opportunities to build that muscle memory.
Robert's partnership with co-founders Alex and Mo lasted through early scaling but ended amicably two years ago. "We all had our three swim lanes and we all swam in our lanes. I handled anything that a CEO, sales, ops, marketing, anything that was customer facing fell into my lane. Alex focused 100% of his time on the product. And Mo was 100% of his time building the product," he explains.
As we discuss in the episode, this resonates with how we built Understory. Having a co-founder with complementary skills creates balance: one person's intensity gets tempered by another's softer approach, and vice versa. The trust that comes from years of friendship means neither partner worries about the other dropping the ball. Beyond skills, the emotional support matters: the founder journey is lonely, and even close friends outside the business don't want to celebrate your wins or hear about your struggles the way a co-founder does.
Clear separation enabled rapid early growth, but personal evolution created natural divergence. "Now life does happen, you know, like they both had and grew their incredible families. You do get tired and you do have to reassess where you want to spend your time." They remain close friends: Robert plays golf with Mo weekly and helped him raise funding for his new venture. Well-managed transitions preserve relationships while allowing everyone to pursue their own path.
During a difficult personal period, Robert lived in Monograph's office for nine months, sleeping on an air mattress and showering at the gym. "I didn't have a place to stay, so I just slept in the office. I slept on Alex and Mo's couch. I showered at the gym. And the air mattress on the office floor worked for almost, I would say, probably nine months," Robert shares.
His framing reveals the mindset separation that enables founder resilience: "When you really like to do something, you're just going to do it. You don't see it as work. Every founder friend I know, we all work hard, but we don't call it work. It's what you want to do." Exhaustion naturally follows intense effort, requiring periods of recovery, but the psychological distinction between "work" and "what you want to do" enables sustained energy during extreme circumstances.
Robert's insight addresses founder sustainability directly. "I like to have other things be predictable so I can deal with the unpredictability of work. If not, because imagine this, if you're everyday at work being unpredictable and then your personal life and everything else is also completely unpredictable. Yeah, that's really really hard. It's a little bit easier if you can keep one side of that constant."
For SaaS leaders managing rapid growth, this principle becomes essential. Creating stable personal systems provides the foundation to handle business volatility effectively. By keeping the external environment controlled, mental bandwidth stays focused on strategic challenges rather than being drained by uncertainty in multiple areas simultaneously.
Monograph's AI feature demonstrates how intelligent automation streamlines professional services workflows. Previously, architects would win a contract and spend hours manually logging client information, project costs, timelines, and resource requirements. "At Monograph, all you have to do is just upload your contract. Our model will essentially take care of everything else," Robert explains.
The system extracts project details, builds proposed timelines, and auto-suggests available team members based on current capacity and skill sets. "It kind of takes a lot of the guessing, a lot of the mundane tedious tasks away." The technical approach combines workflow automation with large language models layered on aggregated data tables. For SaaS companies serving professional services, this demonstrates how AI can eliminate the manual handoff between sales and delivery that scales poorly as customer volume grows.
Robert's father escaped southern China by swimming to Hong Kong when the border was closed. "This was back in the day when China had a closed border. And Hong Kong was still a British colony. So the only way to get freedom was essentially to smuggle into Hong Kong. To do that yet to swim," Robert recounts. His father and one friend survived after three of five companions died during the crossing.
This family history creates what Robert calls an existential advantage. "The stories I hear are insane. I think I can do hard things and like that's a completely different world." When facing difficult business decisions, he has reference points for real adversity that put SaaS struggles in perspective.
As we discuss in the episode, this immigrant family experience resonates deeply with our own backgrounds at Understory. Ali's family also immigrated to the US with his uncle sponsoring his father, similar to Robert's story. That shared context shapes how founders approach risk: when your reference point for "hard" includes escaping closed borders or building a new life from nothing, startup challenges feel manageable by comparison. And for founders fortunate enough to achieve success, giving back to parents who sacrificed everything becomes one of the most meaningful ways to spend that success.
Want more insights on SaaS founder journeys and scaling strategies? Listen to the full episode on YouTube and subscribe to Understory's podcast for more conversations with founders building successful B2B companies.
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