Where you wake up determines your success
Do you have founder-geography fit?
Hi, it’s Melissa, and welcome to “your founder next door”, a weekly column with relatable stories of my journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
This newsletter is the prequel to to “When balance becomes complacency.”
The Big Aha! 💡
Where you live quietly shapes your ambition, your drive, and your definition of success. Years of feeling stuck in Vancouver nearly put out my entrepreneurial fire, until one spontaneous move to New York flipped everything. That decision sparked the Butterfly Effect that led to my first acquisition, meeting my life partner, and building the foundation for who I am today.
Backstory: Feeling stuck at home 👩🏫
I was living in Vancouver, Canada, when I quit my job at SAP to start my first company in 2010. There were no accelerators and coworking spaces; only monthly Meetups where aspiring founders would hang at the neighborhood pub and talk about their ideas. I was one of those founders, and every few months, there’d be a fresh crowd of people cycling in and out as they quit their jobs and re-entered the workforce, realizing how short of a runway they had and how difficult it was to capitalize on an idea.
Trying to build a startup in a sleepy city where very few people are doing what you do is an uphill battle. I know what you’re thinking…and no, Vancouver wasn’t a “startup city”. It had startups in the city, but it was nowhere near San Francisco, New York, Austin, London…you get my point.
The city you live in determines who you are and how you live; it’s the environment and people you surround yourself with. Your friends, your community, your social life, everything contributes to the person you become. This city is not just the physical place you choose to call home -- it’s the vibe, energy, and ambition you absorb by simply existing within it.
I ended up in Vancouver from Calgary when I went to the UBC. Vancouver is a beautiful city with an extremely high standard of living. The scenery rivals any place on best-of lists in North America. It’s got the mountains, ocean, and cityscape all within half an hour of each other. The water is fresh, food is incredible, and people are happy. I’ve never been in a city where people cared about health more than Vancouver. Everyone is always on a special diet or about to try one. Friends of mine in their 20s would skip happy hour because they’re no longer drinking alcohol so they could have an early night and wake up at 6am to exercise before work. But, everything that was right about it for most people was also everything that was wrong for newly minted founders who were activated by networking and exchanging ideas with likeminded people, usually after hours at a bar.
When I was in Vancouver, everyone around me just wanted to live a comfortable, white-picket-fence life. I was one of the few singles in my late 20s not looking to settle down and have their first child. Unlike my peers, I did not want to be a mother. There’s absolutely nothing wrong with that life…it just wasn’t what I wanted. It didn’t help my conviction in choosing something different though when I was often judged for spending time on my business instead of dating.
I wanted to carve out my own destiny, try to make money on my own, and never wake up to an alarm again. I wanted the ultimate lock-up-and-go freedom. I knew I didn’t want a conventional life because I tried putting myself in that box, but it was too unsettling. My parents were each other’s first loves, and I was taught to date only to marry, get a stable corporate job and make myself an attractive candidate for a rich husband. I genuinely tried going down that path, but I was so different from anyone who wanted that life. I just wanted to focus on my projects and earn my way so I could do whatever I wanted.
My friends were supportive of what I was doing but they couldn’t fully understand it because we were on different life paths. The farther along they progressed on theirs, the less we were able to connect, and the more we grew apart as people. My closest friends who got me through my 20s were getting mortgages and adulting, while I was trying to make payroll and next month’s rent.
If you’ve ever tried self-motivating for an extended period of time, you know how exhausting it is to rally yourself day after day. Without an active, thriving community of successful startup founders to bounce your energy off of, Vancouver didn’t have what I needed to keep my fire burning. It was incredibly lonely with no end in sight.
I don’t think this experience was unique, as there must be many others who suffered from their versions of “Vancouver”.
After four years of that, in 2014 I hit a wall.
Triggering the Butterfly Effect: Moving to New York 🦋
One night, I was having drinks in Vancouver with one of the few startup friends and mentors I had, Mike Tippett, the founder of NowPublic which was acquired in 2009 for a reported $25m (he has yet to confirm or deny this).
“What was the best decision you made in your career?” I asked.
He said, "When I was in my 20s, I had $600 in my pocket and I moved to NYC." The Big Apple was where he joined Afternic as one of their first employees, which was sold to Register.com for $60m. NowPublic was a venture he founded shortly after.
I thought to myself that I had more than $600 and had never been to NYC! I was so desperate for change and had nothing to lose, so I followed in his footsteps and moved there a few months later.
When I got there, I had the opportunity to be the third cofounder of Gramercy House, a co-living space at a 5 bedroom, 2-level townhouse in the middle of the city. It was a place where we could live, work, and host events. A spot where we could build community in both our personal and professional lives. When I sold my car in Vancouver, instead of paying off my credit card debts, I invested in this project. (The New York Times touted it as “The Millennial Commune.”)
Two weeks after landing in NYC, I met David at this house, my now life partner and cofounder of eWebinar. He was our first "Airbnb guest" who subletted my roommate's room.
In the living room of this house was where I met every new friend; it became my NYC experience. It led me to business connections and conversations that taught me how to hone in on my startup idea, Spacio (an open house app for real estate agents), which I was iterating on at the time.
Having a dining table that fit 18 people was how I was able to host a dinner with real estate industry leaders, including the CEO of Zillow (Spencer Rascoff). My peers started to notice me after that dinner. They became my friends, gave me advice, and helped me get to first revenue. That event was where I met Aaron Kardell, who would acquire my startup 4 years later.
The Zillow dinner was the greatest hustle story of my career, which I wrote about on this viral LinkedIn post. I invented a story to invite Spencer to my house for dinner, then used his name to fill the rest of the seats at the table. Because I didn’t have any money to pay for it, I found a sponsor to cover the whole thing. I never told Spencer this story until he saw my LinkedIn post - and yes, he did chime in on the comments. 😂 Take a look here.
New York offered vibrant opportunities and perspectives like no other place, and it became the turning point of my career and my life. I fully attribute the success and acquisition of my last startup, and who I am today to my years spent there.
New York State of Mind 🗽
I saw this on Instagram as a description of NYC by ChatGPT:
“New York City is the only place where the myth of greatness still feels within reach - where the chaos sharpens your ambition, and every street corner confronts you with a mirror: who are you becoming?
You love NYC because it gives shape to your hunger. It’s a place where anonymity and intimacy coexist; where you can be completely alone and still feel tethered to the pulse of a billion dreams. It matches your velocity. The people here choose to suffer beautifully: to pay exorbitant rent for a fifth-floor walkup just to be near that energy, that proximity to ambition, art, money, and madness.”
These words encapsulate everything NYC made me feel, I could not have described it better myself.
I moved to the city without a single friend. I felt more aligned with every new person I met than with the friends back home I had known for over a decade — because they were “just like me”. I said yes to everything for two months and became “the person who showed up”, so I kept getting invited to things and grew my network. I went to multiple startup events every week and met founders at various stages who were ready and willing to help. I met with investors and pitched my struggling startup, which led me to the conclusion that I’d be much better off bootstrapping (I shared my story on why bootstrapping is better than VC on S1E1 of ProfitLed Podcast).
For the first time in my life, I was in a city where all sorts of talented people went to chase their dreams. Whether it was building a startup like myself, or trying to make it on Broadway, there was a fire within that was fueled by New York’s collective energy. This energy made up of hope and desperation was inescapable.
This energy made me feel alive 🔥.
New York is where the impossible starts to feel possible because even a stranger will ask, “If not you, then who?” It’s where you can be whoever you want to be and nobody will question your normality, they don’t have time to care. It’s where you will constantly push past your limits because it’s the only way to survive.
And yes, it was where we chose to suffer beautifully by paying exorbitant rent for a property none of us could really afford. The rent and expenses to Gramercy House was $12k USD a month. 90% of what I made went to my room but it was worth every penny because of its stumbling distance to virtually anywhere and its constant flow of people from events we threw.
I moved to New York at the lowest point of my career. I went to sleep with fear and woke up with hustle. 💡Here's the thing:
I loved every moment of it because it gave me the adventure of a lifetime.
Reflections 🪞
As I think about how I moved to NYC on a whim, I'm reminded that the reward of building a startup is not always the financial outcome at the end.
Sometimes, like in my case, it's where your company takes you that is the most life-changing.
The biggest lesson I learned through all of this is:
You never know if your Butterfly Effect is just around the corner.
The day before I left Vancouver, I was nervous about whether I had made the right choice. My friend said to me, “In 5 years, if you decide to come back, everything will still be here. Your friends will be older, maybe they’ll have families, but they’ll still be here. Now imagine, where would you be in 5 years if you went to New York?”
I left, and never looked back.
Stay tuned, there’s more… 👀
🗞️ In the next article, I wrote about what led me to leave New York, find Amsterdam, and how getting too comfortable there almost extinguished my entrepreneurial fire again, leading to my first “mid-life crisis”.
Read When balance becomes complacency here 👇👇👇
When balance becomes complacency
Hi, it’s Melissa, and welcome to “your founder next door”, a bi-weekly column with relatable stories of my journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
Stuff mentioned in this article 👇
LinkedIn Post: I once invited the CEO of Zillow to my place for a Leadership in Real Estate Dinner, then used his name to fill the rest of the seats at my table.
LinkedIn Post: 9 years ago today, I moved to NYC and triggered the butterfly effect that led to the sale of my last company.
ProfitLed Podcast, S1E1: Bootstrapping vs Venture Capital — Why Bootstrapping is Better
Thank you for reading!
— Melissa, your founder next door ✌️
Newsletters I follow (and think you should too) 🗞️
Dr. Julie Gurner: Ultra Successful - Insightful, easy to digest advice & executable strategies that makes you think, by a nationally recognized executive performance coach.
Greg Head: PracticalFounders - Weekly interviews with founders who have built valuable software companies without big funding.
Kyle Poyar: Growth Unhinged - In-depth case studies and deep dives on pricing & packaging, go-to-market strategy, SaaS metrics, and product-led growth.
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That NYC description is spot-on for me too!! Though I am only NY-born. Raised and based in ATL.. a mix of dreams, nerds, hustle (and scamming), suburbs, illusions, rising rent, and “same-old, still there”. Anyways, I am new to the founder journey and this piece brought me much insight. Thank you 🤍