What are you most proud of?

If you weren’t so hard on yourself, what would you be most proud of?

Feb 24, 2025

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.

The story in this newsletter the moment I realized – very recently – that I’d been too hard on myself for the successes I had not yet achieved because I only looked forward to see how much farther there was to go, and never backwards to see how far I’d come. May this be the reminder that we can all use a bit more kindness towards ourselves.

Backstory 👩‍🏫

14 years ago, I quit my job to pursue entrepreneurship without a business idea or a concept of what it meant to start a business. I just wanted to be free of the 9-5, and free of my managers telling me what to do.

In Vancouver where I lived at the time, there was no YC, no Techstars…there wasn’t even a coworking space until a year later. There was only meetup.com where a bunch of us aspiring founders would gather once a month to shoot the shit about the brilliant ideas we were working on. That was how my professional network began, one hopeful conversation at a time. Eventually, Vancouver saw its first accelerator, VC fund, and events like Startup Weekend.

Vancouver’s first co-working space, HackHut turned Launch Academy.

The startup community is funny in the way it ebbs and flows. You meet people who have just left the workforce, full of optimism and hope for the future. They enthusiastically tell you about their idea and how they plan to execute. You’re excited for them and you want them to win. You run into them over and over at various events for months, but then something happens. You start to notice their light dimming as their runway dwindles and they realize that maybe their idea wasn’t as good as they originally thought. One day, you don’t see them around anymore. Perhaps they had to go back to a job…not because they didn’t want it enough, but because life happened. Or, maybe they ended up making things work and moved up the food chain to network in communities of founders who’d also figured it out. Whatever the reason, soon a new set of newly minted founders enter, like excitable golden retrievers.

And that’s how it was for me when I quit my job. I had a bunch of ideas, a lot of them didn’t work out. But I put myself out there, I talked about them to anyone who would listen to get feedback. I iterated, pivoted, and burned through my savings quicker than I ever thought I could. I borrowed money from my parents, applied for government loans, and took out small business loans from banks to keep pursuing my entrepreneurial dream simply because I could not bear the thought of waking up at 8am to be in the office at 9am. I’ve never been a morning person, so the alarm clock was the enemy that kept me from living my best (and rested) life.

Someone once told me that if you give a person enough time, they’ll eventually figure out a successful business. The problem is, most people run out of time. Entrepreneurship is a game of endurance; a game of persisting through different levels of pain for as long as it takes to find a business that pays you a livable wage. You don’t need to be the smartest or the hardest working to win, you only need to stay in the game the longest. I think this is what they call “grit”.

Eventually, I also figured it out, bit by bit. From my first business which was an app development agency I ran for 4 years, one contract at a time…to my second business, a SaaS software in real estate which I ran for 5 years. I’m one of the most “normal” entrepreneurs I know, hence “your founder next door”. I had no entrepreneurial background. My dad worked in the same company for 40 years, my mom was a housewife. My whole founder journey moved at a snail’s pace because I had to learn on my own through trial and error. My biggest advantage was that I was young and single, so I was able to live frugally for years and take on debt without impacting any dependents. The only reason I was able to endure pain for that long was because my pain was isolated to just me.

Most people do not have that privilege. Hats off to those who are on this journey with real responsibilities…

Comparison is the thief of joy 😱

When I was starting my second business, I moved to New York to surround myself with more people like me who were doing cool things. There wasn’t much of a scene in Vancouver and it became increasingly difficult to stay motivated in a sleepy town.

The New York startup scene is active and vibrant. That’s where my professional network exploded. It’s where the smartest, most successful people congregate because it’s New York! The greatest city in the world, and…o yeah, also where the money is. For the first time in my life, I met founders I deeply respected and aspired to become. I met founders who were peers and friends of mine that were featured on Techcrunch, raising tens (sometimes hundreds) of millions of dollars on a whim.

It was incredible to be in such close proximity to the success I wanted to have, but also soul crushing as I was trying so hard at the time and could barely get my startup off the ground. That said, I loved it because it fueled me. I loved knowing how high the mountain was because I was hopeful that I, too, would get to the top one day.

That, however, was a double-edged sword. When you’re around people who are achieving things that you are not, it’s impossible not to compare yourself to them. Over the years, I watched friends who were younger than me, spend less years on their businesses, and exit for 8 to 9 figures. These things often led me to question my own ability…

Am I not as smart as them? If yes, then why am I not as successful?

What if I never see the success that I want? Will it ever be my turn?

Should I keep going or am I wasting my time?

Am I even meant for this? What if I’m not? 😟

selective focused of brown dog lying on sofa — Picture of a puppy to break up the text.

I’m well aware that comparison is the thief of joy, and the only time you should look into your neighbor’s bowl is to make sure they have enough. But we’re entrepreneurs and we wouldn’t be doing this if we didn’t have big egos. My ego wants me to win too.

I’ve been blessed to be surrounded by a community of founder friends that I look up to and learn from, who have been pillars in my journey. I designed it that way by surrounding myself with superstars, people who inspire me to be better by simply existing. While I’m happy for their success, it makes me feel like a complete failure.

I’ve had some successes in the last decade, but not enough to feel at peace, so every day feels like a rat race. There’s always another level to unlock, another growth hack, another million ARR.

I am always chasing the next thing, unable to be happy and content with where I am today.

Reality check ✅

Last month, an old friend from my past life in Vancouver reached out to me on LinkedIn and wanted to catch up. This was someone who tried and tried and tried and couldn’t make his startup work. After years of trying, he hit the end of the road, went back to corporate, and vowed never to start another company again. I can honestly say that he was one of the hardest working founders I’d ever met. He tried everything under the sun, and nobody would’ve blamed him if he gave up earlier. Unfortunately, he couldn’t find product market fit, and couldn’t get adoption and revenue.

We hopped on a call and updated each other on the last several years. He was there when I was at the lowest point of my career, struggling the most with my last startup. He watched me get annihilated by over 20 VCs at a pitch event, Shark Tank style, telling me how my startup would never work because my total addressable market was too small and that I needed to change my product and business model. (PS. That startup was acquired because we were the best-in-class in our category for the niche market we served, which I wrote about here.) He saw how miserable I was from trying things that didn’t work, but we lost touch before I came out the other side.

On that call, I matter-of-factly shared with him how I kept going in my last startup until we became profitable. How I sold that business and founded eWebinar by investing my own capital. And how I intentionally designed this startup as a lifestyle business to give myself, my cofounder (and life partner) a life of freedom where we have a fully remote team of contractors, no meetings, no live calls and events…ever. We have a home base in Amsterdam, travel 10 months of the year, and go to as many fun things as we’re invited to.

David and I with our community at our friend’s festival in Portugal, July 2024.

“Sounds like you’re doing great!” He said.

“We’re not where we need to be.” I responded. “We’re barely at break even, our growth is stagnant, and we have no idea what we need to do to get this business to the next level.”

“You have autonomy. A lot of us set out to find it, and you actually achieved it. You’re living it.”

That was my reality check. All these years I had been so consumed with looking forward to see how much farther there was to go, I forgot to look backwards to see how far I’d come. I’ve only compared myself to those who were so far ahead of me, and failed to recognize my tenacity beyond those who didn’t — or weren’t able to — keep going…all those other founders I had met along the way, who came in and out of my life like the wind.

All this time, I had forgotten to congratulate myself for doing the hard things that were required, even when I didn’t want to, so I could live the dream life that I have today.

What are you most proud of? 🤩

Recently, I was on a podcast, and the host asked me, “What are you most proud of?” And that got me thinking…

For me, it’s RIGHT NOW.

A lot of people may hear that question and think of a financial success or milestone. That’s understandable, because money is a quantifiable measure of success.

14 years ago, I left my cubicle to pursue a life of freedom, without knowing what true freedom meant. I just didn’t want to wake up with an alarm clock anymore. For years, I refused to give up no matter how difficult things got and how much debt I was incurring. I believed things were going to be okay if I kept trying. I saw the light at the end of the tunnel when no one else did. I kept going when giving up seemed to be the only option. I did what needed to be done because I didn’t have a plan B.

My first two startups were good, not great – but they gave me the experience and capital to found eWebinar 5 years ago on my own terms; I intentionally designed my life around enjoyment by putting myself first; something I had never done because I didn’t know how. To this day, I actively prioritize happiness over revenue in every part of our business so we can live our lives to the fullest while we build rather than deferring the fruits of our labor.

I didn’t pay myself for the first 4 years, until everyone else got a good salary. For the first time in my life, right now, I’m finally getting a proper salary that allows me to live a “normal life” without compromises. I don’t have everything that I want, but I don’t feel like I’m lacking.

Now, I am truly living the life that I dreamt about 14 years ago. This is what I am most proud of.

The biggest lesson I learned through all of this is:

We all need to be kinder towards ourselves.

Reflections 🪞

As founders, we are so hard on ourselves for the successes we have not achieved. Our goalpost is constantly moving, and that is fine, as long as we recognize that and also celebrate our successes, the mini goals we did accomplish along the way that got us here.

There’s always going to be someone doing better than you. More successful than you (not just financially, but in every sense that you want). There’ll always be someone who has what you most desire. That’s amazing, because they show us what is possible.

Just because you haven’t seen success the way you want to yet, doesn’t mean you’re not successful at all.