In a recent conversation with Demetri Themelis, co-founder of Knock, I was struck by how many parallels existed between our entrepreneurial journeys. From similar motivations to start a business to the challenges of finding product-market fit, Demetri's story offers valuable insights for multifamily leaders and aspiring entrepreneurs alike.
So, I’ve decided to write up some of the lessons I took from that conversation, which you can listen to in full here:
When Financial Insecurity Becomes Fuel
Like many entrepreneurs, Demetri's drive wasn't born from privilege but from witnessing financial stress firsthand. "I have very early memories of waking up and hearing my parents fighting about money," he shared.
This experience created a powerful motivation to build financial security—something that resonated deeply with me as I had similar experiences growing up.
What's fascinating is how these early experiences shape our relationship with risk.
They don't necessarily make us risk-averse – instead, they can propel us toward calculated risks with the determination to create something better than what we knew growing up.
The Institutional Credibility Gap
One of the most enlightening parts of our conversation was Demetri's realization about institutional credibility.
In his previous role at UBS, he could make a quick call recommending stock trades, and clients would move millions based on his word. Yet when he stepped out to build Knock, that same credibility vanished overnight.
"I remember telling Tom, my co-founder, I'm going to be able to raise us millions of dollars, just a few phone calls," Demetri recalled. "I was so wrong about that."
For multifamily and tech entrepreneurs, this highlights an important truth: breaking into the industry isn't just about having a great product—it's about building trust in a space where decisions aren't made lightly.
Your solution might be revolutionary, but without established credibility, the journey to your first customer will be hard.
The Three-Year Journey to the First Check
Perhaps the most powerful story Demetri shared was about receiving Knock's first customer check: $75 from Connecticut Realty Trust in March 2016—nearly three years after he and Tom Petry quit their jobs to pursue their vision.
"The feeling of holding that check and being both incredibly excited because it was the validation of everything that we'd been through... Three years worth of problem solving, challenges, fundraising, like every problem, you name it."
This perfectly captures the pre-revenue phase that most tech startups face.
It's a jungle where validation is scarce, and faith must sustain you.
For property management leaders considering developing their own solutions or entrepreneurs entering this space: be prepared for a marathon, not a sprint.
When the Customer Reshapes Your Vision
Demetri and Tom started with a simple concept: create an "OpenTable for apartments"—a straightforward scheduling tool. What they didn't anticipate was how deeply they'd need to understand the multifamily industry's workflows.
When one customer sent a list of 63 feature requests, it caused a moment of crisis. As Demetri put it, "Will we ever have a business if it's going to take 63 custom feature requests to build one customer?"
They built all 63 features and converted that pilot into a paying customer.
The lesson? In multifamily tech, flexibility and customer-centricity aren't just nice-to-haves—they're survival requirements.
The product that achieves market fit rarely resembles the founder's original vision.
My Co-Founder, Kendrick Bradley, actually wrote about how we have taken on this mindset at Zuma and worked with our customers to shape our products. You can read it here.
Finding Balance in Leadership
Demetri's partnership with Tom offers a masterclass in complementary leadership.
"In the Venn diagram of strengths that two people could have coming to the table, we had very different sets of strengths," he explained.
Demetri excelled at sales, marketing, and customer-facing functions, while Tom's analytical mind and attention to detail made him perfect for product development and technical challenges.
For multifamily leaders building teams, this highlights the importance of surrounding yourself with people whose strengths differ from yours. The strongest organizations aren't built on uniformity but on complementary capabilities.
Life After Exit: The New Challenge
Two years after Knock's acquisition by RealPage, Demetri shared an unexpected insight about life post-exit: The financial security he worked decades to achieve brought its own challenges.
"It's like you're partying in a basement techno party for two decades, then you step out into a jazz bar and everything feels weird," he explained. Finding motivation beyond the all-consuming startup journey requires intentional effort.
What struck me was how Demetri described the psychological adjustment: "There's a mantle of pressure on you that I don't think can be replicated if you're not an entrepreneur. I've never experienced anything like that."
Having that pressure suddenly lifted created a void that was both freeing and disorienting.
His coach offered two powerful frameworks: "You've proven you can run, now you have to prove you can jog," and the idea that he had been "drinking from one bucket to energize himself" when there are many sources of purpose and meaning.
For Demetri, this meant exploring new avenues: starting a family, buying a house, volunteering at church, reconnecting with friends, and pursuing hobbies that were impossible during the all-consuming founder journey.
This perspective is invaluable for any leader who has tied their identity tightly to their professional role.
The skills that make you successful as a founder—intense focus, high-stress tolerance, single-minded drive—may need to be balanced with different capabilities in the next chapter. Perhaps most importantly, Demetri reminded me that true success means being present with family and friends in a way that the founder journey rarely allows.
Final thoughts
Conversations like these remind me why I started this podcast.
Behind every multifamily tech solution are founders who navigated uncertainty, faced rejection, and transformed their vision countless times before creating something of lasting value.
Whether you're leading a property management company, developing new technology, or just starting your entrepreneurial journey, I hope Demetri's story provides both inspiration and practical insights for your own path forward.
You can check out all episodes of Humans of Multifamily here!
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