Hi, it’s Melissa, and welcome (back) to “your founder next door“, a weekly publication on the strategies and stories behind building a company without an abundance of resources and friends in high places. No BS, just straight-up truth bombs.
A friend said something to me a few days ago, “I really respect the amount of risk and uncertainty you were able to endure (in your last startups). What was your main motivation? Freedom?”
It got me thinking about that thing we call “risk”.
Dictionary.com says it’s the exposure to the chance of injury or loss; a hazard or dangerous chance.
I looked back at my career and pinpointed the audacious, unreasonable things I did. The things people standing on the sidelines would call “risk.”. I never thought of any of it as danger. Risk never felt like risk to me.
In my early twenties, almost right out of university, I was a real estate agent making over $100k a year, which at that age was real money. I hated the job, so I quit. I moved to Hong Kong, and fell into international trade, manufacturing furniture in China and shipping it around the world.
My parents were furious. I finally had a job paying me enough and I’d pulled the plug because I didn’t like it. Why can’t you just be happy and settle down?
I lasted a year and a half. I didn’t like living in Hong Kong as I was at my parents’ house. Pulled the plug again and moved back to Vancouver.
Later, I was in large enterprise sales at SAP. Good company, good position, a clear corporate ladder to climb. I quit that too, and friends asked me the same question. Why would you leave a job like that?
I left SAP and started my first company. Commission jobs in my early twenties meant I’d saved what I thought was two years of runway at the time.
I burned through almost all of it in six months.
Then came the small business loans and the government grants. Then I maxed out all my credit cards. It took closer to two years after quitting SAP before I made my first sale. For the first time in my life I was living paycheck to paycheck.
It was uncomfortable, but it wasn’t scary.
I spent every dollar without second guessing, because there was no doubt in my mind I wouldn’t make it back. I’d never been an entrepreneur. I had no idea how hard it was going to be. I thought you made a product and someone bought it, because I came from sales and selling had always been easy for me.
I was so naive. That naivety is probably the reason I didn’t see risk.
Then I moved to New York with nothing. (I wrote about that move and Founder-Geography Fit here: Where you wake up determines your success)
A friend once told me the best decision he ever made for his career was moving to New York with $600 in his pocket. I remember thinking, well, I have more than $600. I can move there too!
I was between my first and second company, burning a loan I’d taken out against my first company’s revenue, trying to build my first SaaS product. I was spending close to 90% of what I made on rent every month. I ate one meal a day. (I wrote about all of this in My Founder Story.)
I knew no one. I had no community, no network, no plan. Anything could have gone sideways and there was no floor underneath me.
That was the scariest thing I’ve ever done. I was scared and I did it anyway, because something in that city was calling me and I’d stopped being able to ignore it.
Here’s what that one decision gave me…
I met David within weeks of landing. My partner, my husband, my cofounder. I had the best years of my life in the best city in the world. That’s where my greatest hustle story happened, the one where I invited a CEO over for dinner. That’s where I met the person who eventually acquired my last company.
Every single thing that matters in my life traces back to a decision that looked reckless from the outside.
💡 Here’s the thing: When you take enough of these leaps and collect enough rewards on the other side, you stop seeing the leap as the dangerous part. You start seeing standing still as the dangerous part.
Had I not quit SAP, maybe I’d still be there, or somewhere just like it. Had I not started that first company, I’d never have known what freedom felt like, and I wouldn’t have kept trying. At the time, freedom only looked like time. No alarm clock and sleeping in. Watching TV until 2am because no one could tell me not to.
Freedom has always been my number one priority. I’ve written about it, built a company around it, and it’s the reason behind every major decision I’ve made.
“Freedom” is the answer to my friend’s question. She guessed right.
Once I tasted it, going back was unthinkable. In my darkest years, the thing that pushed me to do the next hard thing was the image of myself back on a train at 8am, heading to someone else’s meeting.
That image was scarier than any leap.
What is the greatest pain in the world? It’s the pain of regret. The pain of knowing you could’ve done something when you had the chance. The pain of realizing you can never go back.
So take the leap. Make the awkward cold call. Knock on the door. Rejection stings, I know.
But I can think of a lot of things that sting more than trying to go after your dreams.
Till next time,
— Melissa, your founder next door ✌️
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Thanks for this, Melissa. It's true that standing still and living with regret is way scarier than taking a leap. Love this perspective on reframing what "risk" actually means.