Michael Litt and Humza Ahmed on Building Through Different Eras
Second Founder Dinner for W26: YC '11 meets YC '25 + B2B SaaS meets AI-native infrastructure + 15 yrs of lessons compressed into one year = why the fundamentals never change but everything else does.
TL;DR: Michael Litt (Vidyard CEO, Garage VC GP, YC W11) and Humza Ahmed (Automax.ai CEO, YC F25) shared the second dinner of our W26 series. Separated by 15 years of startup evolution, their conversation revealed a striking truth: the fundamentals of building—founder-market fit, distribution challenges, doing things that don’t scale—remain constant even as AI reshapes execution speed. Michael’s journey from video tools to B2B SaaS giant informs his investing thesis. Humza’s path from weekend demos to full-stack appraisal company shows how today’s founders iterate faster but face the same human challenges in hiring, firing, and finding product-market fit.
This week’s second dinner, thanks to the support of Osler and TD Innovation Banking, brought together two builders whose stories bookend a transformative period in startup building. Michael Litt co-founded Vidyard in 2011, went through Y Combinator, and spent over a decade scaling it into one of Canada’s most successful B2B SaaS companies. As a GP at Garage VC, he invests in early-stage technical founders, bringing operator experience to the table.
Humza Ahmed represents the new generation. At 21, he dropped out of Waterloo exactly one year ago (January 20th, to the day of the dinner), moved to San Francisco, went through YC’s Fall 2025 batch, and raised $4.5M to build Automax.ai, an AI-native appraisal platform that’s disrupting the mortgage industry.
The Common Thread: Founder-Market-Channel Fit
Michael framed the evening around a concept he returns to constantly as an investor: founder-market-channel fit. “You have the capabilities of solving a problem - you can write software, it’s easier than ever to do that, though it’s way more complicated to build real value. You understand a market deeply. And you’ve figured out distribution.”
Humza’s story perfectly illustrates this framework. His extended family operates real estate appraisal firms, his grandfather started one in the 1970s. At a family wedding, he kept hearing complaints about manual data entry and week-long turnaround times for appraisal reports. The problem was staring at him, “kind of unsexy” as Michael noted, but deeply understood.
Over a weekend, Humza built a demo that automated appraisal report writing. His family’s reaction - ”this is insane, you should talk to other appraisers” - led him to create a fake LinkedIn profile (complete with AI-generated beard and suit) to appear older and credible to industry veterans. When the CEO of Canada’s largest appraisal company saw his Figma mockup and wanted a demo, Humza spent that weekend building something that would “all break apart” if you pressed a single button but it was enough to sign his first enterprise customer.
Things That Don’t Scale (Still Don’t Scale)
The conversation kept circling back to a Paul Graham essay that shaped both their journeys: “Do Things That Don’t Scale.” Michael talked about Vidyard’s early days doing whatever it took to understand customers. Humza described spending months in enterprise discussions with his first customer, building to a 13-page requirements list before getting real user feedback, a mistake that cost them 200 pull requests of wasted work.
“The first version of our product that they were paying us for took 200 pull requests to get there,” Humza explained. “Now anytime we’re building any feature without thinking about this from a customer perspective, I say ‘200 pull requests guys, we’re not going to make the same mistake again.’”
The lesson transcends technological eras: you have to do the unsexy work of deeply understanding your customer’s problem. For Humza, that eventually meant hiring his customers, the appraisers, onto his own team and becoming a full-stack service provider, not just a software vendor.
The Full-Stack Pivot
One of the evening’s most revealing discussions centered on Humza’s pivot during YC from selling software to appraisal firms to becoming an appraisal company themselves. His first customers were paying “peanuts” for technology that was saving them days of work, yet they remained inefficient and slow.
“I regret not building the full-stack thing sooner,” Humza admitted. “I used to think I need to build a tech company, I need to be a tech founder, I don’t want to do services. But the more you build and learn, the more you realize that the only thing that really matters is creating value and doing the thing that creates the most value.”
Michael connected this to a pattern he sees across Garage’s portfolio: “You can’t build a big business just selling a tool. You have to basically own that industry.” He cited examples like Cartage, which evolved from booking software to a full 3D logistics company, and a YC company in company valuations that started with tech support before moving upstream into full auditing services.
The insight cuts to a fundamental tension in startup building: the ambitious vision versus realistic execution. As Michael put it, “You need to eat an elephant one bite at a time. Market size initially doesn’t matter. Pick a really small problem where nobody exists. As you solve that small problem, you realize you can automate that entire industry.”
The Waterloo Ecosystem Advantage
Both founders leveraged Waterloo’s unique position in the startup ecosystem, though in different ways. Michael’s Vidyard emerged from the University of Waterloo’s engineering talent pool and the nascent Velocity program. Humza, arriving a decade later, found a more developed infrastructure - Jesse Rodgers’ Founder Dinner series, connections to VCs who had come through the same path, and a network of technical talent willing to drop out and build.
The evening included stories of early Waterloo/YC successes that shaped the local ecosystem - companies that validated the path from university to accelerator to acquisition, creating a template for future founders. These early wins, even the near-misses for early investors, helped establish the pattern of Waterloo founders supporting each other across generations.
That ecosystem thinking - paying it forward, staying connected to Waterloo even while building in San Francisco - creates a flywheel. Humza is already opening a Canadian office for engineering despite being based in the Bay Area.
AI Changes Speed, Not Fundamentals
A question from the audience got at the heart of what’s different today: has AI fundamentally changed what it means to build a startup?
Michael’s answer was unequivocal: “AI has really just changed the rate at which you’re iterating and the speed at which you’re building, not ultimately what you’re building, which is just creating value.”
Humza agreed, noting that while he can prototype faster and leverage AI for product development, the hard parts remain hard: finding product-market fit, hiring the right people, building distribution, maintaining motivation through the grind.
“There’s so many options in every single category now,” Michael observed. “You have to be the best product to fundamentally win. The pressure on the quality of the product and the value it delivers is much greater now than it used to be.”
The Hiring Trap
Perhaps the evening’s most valuable discussion centered on hiring mistakes. Michael has cycled through seven revenue leadership teams at Vidyard. Each time, he fell into the same trap: hiring someone with impressive credentials from a big company who brought a playbook that didn’t translate.
“First-time founders look to hire people to make their life easier,” Michael explained. “Those individuals come with a playbook that is often irrelevant to your business. They had a billion dollars of R&D and marketing spend behind them at Salesforce or Shopify. You’re not going to have that.”
The lesson he’s learned: “Look for people that are scrappy and are going to accelerate your company from a first principles understanding of your customer, your needs, and what your product has to do. Hire people that have that same energy and care that you do.”
Humza shared his own recent painful experience: hiring his first engineer, knowing within two days it was wrong, but delaying the firing for a month during YC. The result was code so poor he had to scrap it and rebuild himself. “I wanted to give him a chance because no one starts at the perfect level,” Humza said. “But that subconscious feeling of letting somebody down is a distraction, and that’s demotivating.”
Michael’s advice was blunt: “Higher slow, fire fast. And firing people fucking really, really sucks.” He described having to terminate someone three minutes before a call where they shared news about their mother’s brain tumor and a new apartment deposit. “That’s why you need the high bar, because you’ll delay firing them, you’ll build a team of low performers, and it compounds.”
Building for the Long Game
The conversation turned to what actually motivates founders to build venture-scale companies versus lifestyle businesses. Michael reflected on patterns he's observed across hundreds of investments - founders who succeed at scale often have a chip on their shoulder, something driving them beyond just financial outcomes.
Humza's story illustrated this clearly. After multiple acquisition offers during and after YC - including one at exactly the $10M number he'd calculated as "never have to work again" money - he faced a moment of clarity: "I'm going to spend a year traveling, then what do I do? I just start the next company. There's nothing else I'd rather do than just building the next company to be even bigger. So why waste this opportunity to build what could be a monumentally generational company?"
That clarity about motivation - not building to sell, but building because it's what you actually want to do - separates lifestyle businesses from venture-scale outcomes. Understanding your own motivation becomes critical when the grind sets in and early exit opportunities appear.
Vision That Evolves
When asked about his big vision, Humza offered something appropriately blurry: “I see the home buying process changing entirely in its structure.” Rather than appraisals happening at the very end of a transaction to confirm a deal, he envisions them at the beginning - sellers scanning their homes, getting data on which improvements add value, creating transparent 3D tours with appraisal data for every listing.
“That evaluation is no longer a black box,” he explained. “You build an evaluation framework, that’s the first step to building a true marketplace where you no longer need real estate agents or lawyers. The entire way we buy and sell homes basically goes away and becomes a fundamental marketplace.”
Michael smiled at this. “The vision (for Vidyard) was always there, that the way we get there has changed as the technology landscape has evolved.”
Key Takeaways
The evening crystallized several insights for early-stage founders:
Founder-market-channel fit matters more than the idea—deep understanding of a problem, capability to solve it, and a path to distribution beats a clever concept.
Full-stack often beats pure software—especially in established industries where you need to own the entire value chain to create transformative change.
Speed of iteration has increased, but the fundamentals haven’t—AI lets you build faster, but you still have to talk to customers, do things that don’t scale, and find product-market fit.
Hiring is where first-time founders make their worst mistakes—look for scrappy, curious people who understand your customer, not impressive resumes from big companies.
The ambitious vision needs to coexist with realistic next steps—you need to know you’re climbing Everest, but you can only see to the next base camp.
Motivation matters more than opportunity—understanding why you’re building (not just for an exit) determines whether you can sustain through the hard parts.
As the dinner wound down and founders continued conversations over the remnants of home-cooked food, the intergenerational exchange revealed something important: Waterloo keeps producing builders because the community shares these lessons forward. Michael investing in Humza’s round. Jesse running these dinners. The ecosystem paying attention to what works.
The tools change. The speed increases. But building something people want - truly want, enough to pay for, enough to change their behavior - remains as hard and as rewarding as ever.
About this series
The Founder Dinner series is offered by Builders Club and Barn Ventures. The series features home cooked meals, founder discussion and connection, and is supported by a workshop series that has been developed with founders. This has evolved over nearly three years with the support of various people and organizations in the ecosystem. We have had a significant number of founders move on to raise capital from YC, Afore.vc, Garage VC, etc. Founders from companies like Datacurve.ai, Voltra, Automax.ai, and many others have attended.
Applications are open for the next series in the spring.