How I found product-founder fit

I never aspired to be a founder, but I’m hoping that once you read this story, you’ll understand how I couldn’t possibly say no and realize that maybe you can be a founder, too!

In 2013, I was working as a waitress to make ends meet while I figured out what I really wanted to do. I stumbled into software engineering, almost by accident, when a friend mentioned something called a “dev bootcamp.” The concept was totally foreign at the time, but I crossed my fingers that it wasn’t a huge scam, and moved to San Francisco.

I managed to (barely) squeak out a job at a small startup, where I learned a lot, before moving over to Reddit. I had a blast learning how to build features at scale, but after two years I began to feel frustrated at the slow pace of my career progression — I felt helpless in pushing myself up the career ladder.

It wasn’t until I discovered a reliable and repeatable formula for career growth that I started seeing the gains I was looking for. I was quickly promoted to Senior Engineer, then manager of a team, and then two teams. I thought “This is nuts. If I can do this, anyone can” and founded the GAINS Program to share my knowledge and empower others to take their future into their own hands. And it worked — graduates of my program regularly received the promotions and raises they were looking for. I took my learnings on the road to empower women outside of Reddit, speaking at the Women in Tech Conference and the Grace Hopper Celebration in 2019.

I tell this long-winded history to make it obvious: I have a longstanding passion for empowerment. One of my core beliefs is that the only way to attain empowerment and equality is through equal access to knowledge. I especially care about empowering groups that are on the shitty side of some information asymmetry — that is, those who would benefit if they just had all the information available to them.

Although this is a passion of mine, I never ever saw myself running a company. It just seemed impossibly difficult. So when a friend approached me about his prop-tech startup idea, I was skeptical. “The space is so crowded!” “I’m pretty sure big prop-tech has a handle on it,” I objected. He said to me “OK Sam, if you’re so smart, how would you go about buying a home?”

His question stopped me in my tracks. I had no idea how to buy a home. I didn’t even know what the first step was. Looking at houses? Calling an agent? Talking to a bank?

How was it possible that something so common, that everyone in my family had done, was so foreign to me? On top of that, is the advice my parents would give me still even relevant? And what about people who were first-generation homebuyers — how were they faring? This realization set off a series of lightbulbs in my brain. There was a HUGE opportunity here to empower an entire generation of first-time homebuyers by simply giving them equal access to information.

Traditionally, first-time homebuyers are at the mercy of their real estate agent. It is impossible for homebuyers to partner with an agent from a place of mutual understanding and strength, simply because the home buying process is complicated! Because home buyers have no idea what to expect, they often lack confidence and are underprepared during the process. And why shouldn’t they? This is the largest purchase most people will ever make, and they are coming to the table completely unprepared. Furthermore, agents don’t want their buyers to feel nervous either! This dynamic is completely detrimental to both parties.

So, I quit Reddit and took on building DwellWell full-time with my co-founder, Matt Canzoneri. We have built a step-by-step home buying web app that walks you through every step of the buying process. Our approach requires an extreme focus on helping home buyers, whereas most traditional prop-tech is focused on helping home sellers, loan refinancing, or with real estate agent tooling. This seems crazy to me. If you’re the person spending a million bucks on a house, why isn’t the process catered to you? DwellWell’s buyer-centric approach delivers education, decision-making tools, and recommendations for our home buyers that empower them.

And we’re just getting started. Our ultimate goal is to forever remove the information asymmetry that exists within the home buying process and empower future generations of home buyers. When we make the relationship more equal between buyers and real estate agents, banks, inspectors, and more, we will have succeeded.

I explained at the top what an unlikely founder I am. I’d like to leave you with a few key takeaways, in the hopes that it inspires someone who doesn’t view themselves as founder material.

1) Principles matter. Write down your core principles and go after opportunities that allow you to exercise them.

2) Take smart risks. I had no idea what an engineering boot camp was, but I knew I wanted to learn a new skill and was open to taking a risk. The same applies to starting a company and building a first-of-its-kind product. The scariest part is making the decision to do it.

3). Your cofounder matters (A LOT). I couldn’t do any of this without Matt, who motivates me, runs the entire financial side of the business, and challenges me to reevaluate my preconceived notions.

You can learn more about DwellWell here.