Now I quit my job to start a startup
So I guess we’re both doing it
I wasn’t put on this earth to build someone else’s dream.
Ever since college, I’ve wrestled with finding meaning in my work. The closest I’ve come has been through side projects like Slice of SF, Nexus Maine and Hawk Hill Ventures. I’ve spent countless hours admiring those I look up to, wishing for their success, while avoiding the steps required to get there. I was enamored with the destination, not the journey. But over time, I began to notice a pattern: my moments of professional excitement and fulfillment always revolved around one thing—agency.
Updater gave me my first taste of agency, and for that, I’ll always be grateful. But the longer I stayed on the traditional path—software engineer to product manager to director of product—the more I realized it wasn’t for me. I wanted to build. I wanted to sell. I wanted to understand customers deeply and market to them effectively. I wanted to learn. Yet, in most of my roles, I kept hearing, “That’s not your responsibility” or “Stay in your lane.”
Nine months ago, I woke up and finally recognized that only I could change my situation.
The Team
First of all, none of this would be possible without the incredible support of my wife, Anne and her belief in me. Absolutely none of it.
People are the single most important ingredient. I am incredibly lucky to have found my co-founder, David LoBosco. Introduced by our mutual friend and his former CEO, David Engle, David LoBosco is a rare talent—a 10x engineer, intuitive designer, and product thinker who always puts the customer first. His skills complement mine, and he challenges me to think bigger and execute better. This journey wouldn’t be possible without him.
I also want to acknowledge Paul Klein, my partner in Hawk Hill Ventures and a founder I deeply admire. Paul’s resilience, grit, and generosity have been a guiding light for me. Watching him tackle the highs and lows of building Browserbase has been inspiring. His support gave me the confidence to take this leap.
To the rest of my family, friends, and mentors—your encouragement has been instrumental, and I’m beyond grateful for the role each of you has played in getting me to this point.
Getting to the Idea
Sometimes you can’t get an idea out of your head and it just starts to eat away at you. You question the very nature of an industry, someone’s way of working, the way time is spent, something you wish existed…
And sometimes, you want so badly to force something into existence by sheer power of will, regardless of the need. You want to create a reality that is different from your current one. You ask yourself “who do I admire? What do those people all have in common? What do I like about my life? What don’t I like about my life?” The list goes on and on and eventually, you take steps in the direction you think is right. However, aftering hearing about why I thought it was time for someone to build better gym software because MindBody sucks, my friend and advisor Drew Geant asked “are you playing to play, or are you playing to win.” That knocked me back a few pegs…
The idea maze is a tricky place to be and when you lack direct experience and a historical background on what you’re considering, it can feel neverending. The process sets you on this rollercoaster ride of highs when you think you’ve figured it all out and lows when you realize you’ve just come up with A) a horrible idea, B) an entirely undifferentiated idea, C) a tarpit idea, D) something impossible for you to build, or E) all of the above! After a while in the maze and thinking about Drew’s observation, it was time to take a step back. It was time to ask myself what problem I actually know about, what unfair advantage do I have, what motivates me.
There is one problem that has actually annoyed me for years on end and hasn’t gone away but the path to solving the problem seemed daunting and improbable…but that is because I kept looking at how it had been done before.
To reference Dharmesh Shah, many of the dots I’d been collecting for so long finally started to connect. The vision started to become clear. The problem now feels urgent, and the solution almost inevitable. It’s not just about iterating on the old but instead creating something entirely new; it’s about transforming the way people work, freeing them from inefficiencies, and building something that feels essential to the way we will work in the future.
What you’re about to read has finally been born from this drive to solve real problems in a meaningful way and modernize the way the physical world is managed.
The Industry
The property management industry generates about $100 billion annually but it feels like a small, tight-knit community. It’s an industry where everyone knows everyone, and even competitors maintain friendly relationships. I love it, I’ve never experienced anything like it and I am motivated to help improve it.
In this world, there are a few universal truths:
Products are sold, not bought.
Nobody likes their property management system.
Nobody will rip out their property management system.
Site-level staff turnover is absurdly high.
Software is rarely bought by the people who actually use it.
Property management software emerged in the 1980s with pioneers like Yardi and RealPage. These companies built the first on-prem systems, and while they’ve since moved to the cloud, their solutions remain far from modern. Their dominance has created a fragmented ecosystem of point solutions, resulting in silos, login fatigue, user dissatisfaction, inaccuracies...
After decades of unbundling, the industry is now craving rebundling. Several challenger property management systems have recently emerged, raising significant funding and sparking hope for a better future.
Introducing, Rely…sort of…
Rely was born out of a desire to combat the pervasive effects of turnover in property management. We’re building software for the people who actually use it—an experience designed to empower end-users, simplify workflows, and modernize the way the physical world is managed.
More to come on this soon though. Stay tuned.
Conclusion
When I graduated from middle school, I got to pick a quote that I liked or felt I could relate to and what I chose is, in hindsight, wildly embarrassing. I chose something from John Mayer: “everyone’s a stranger, but that’s the danger in going my own way.” While I was probably 13 years old at the time, something about that quote still resonates with the log-sized chip I have on my shoulder.
This decision to start my own company feels both daunting and exhilarating. For years, I’ve looked up to founders and creators who had the courage to step off the beaten path and build something meaningful. Now, it’s my turn.
For me, starting Rely is about more than just solving a problem. This is also about living with intention, chasing the vision of the life I want, and creating something that matters. It’s about choosing the harder, more uncertain path because that’s the one that aligns with who I am and what I believe.
I know this journey will be filled with challenges, setbacks, and unexpected twists. But I also know it will be filled with growth, learning, and the joy of creating something from nothing with amazing people. For the first time in my professional life, I wake up every day with a clear sense of purpose and excitement about the road ahead.
To everyone who’s supported me, challenged me, and encouraged me to take this step—thank you. Your belief in me has been a guiding force, and I’m endlessly grateful.
To anyone reading this who is contemplating their own leap of faith, bet on yourself. The journey may be uncertain, but it’s the only way to truly discover what you’re capable of.
It’s time to chase the dream. This year, I woke up and decided that “I am going to play for the asymmetric life.” – Paul Klein – Graham Weaver