About Will Cannon
From a One-Bedroom Apartment to $30M+ in Sales — Without Raising a Dime. (How I Bootstrapped My Way Out of Broke)
Humble Beginnings
I grew up in a tiny apartment in Southern California — just me and my mom. We didn’t have much. Single-parent household. Always tight on cash. When I was a kid, all I wanted was a pair of Jordans.
Not because I wanted to fit in — but because I loved basketball, and Jordans were part of the culture. We couldn’t afford them. So I learned something early:
If I wanted something, I had to figure out how to earn it. Like a lot of kids with hustle, I started with a lemonade stand. Then it was selling CDs at school. Then flipping car parts. By 16, I was working full-time selling appliance warranties — while still in high school. That’s when I realized: no one’s coming to save us.
If I wanted a different life, I had to build it.
The early hustle
One day was enough
I left college after one day, knowing school wasn’t for me.
Passed over, moved on
I became a top rep at a collections agency — until I got passed over for a promised promotion. So I quit.
10K and a bathroom break
A friend introduced me to the mortgage industry. First month in, I made the company $100K — and got paid $10K. It was the most money I’d ever seen. I thought I was rich… until I got scolded for leaving my desk to use the bathroom. That moment, I knew: I couldn’t work for anyone else again.
From partners to co-founders
My girlfriend (now wife) and I decided to start our own mortgage company. That same day, I walked out and never looked back.
The cold email spark
While building that business, I started using cold email to recruit loan officers — and it worked. This was 2006. That moment sparked my obsession with outbound sales.
Crash. Burn. Rebuild.
Then 2008 hit. The crash wiped us out. Bankruptcy. Foreclosures. Back to zero.
Building something from scratch (Again)
Starting over, I found a company for sale on BizBuySell that sold email lists. I already had some — I thought, I can do this too.
So I started buying and selling lists. Then I launched a website. Then a marketing agency. For over a decade, I ran cold email campaigns, built lead gen systems, and helped businesses scale with better data — one client at a time.
It was good money. But it wasn’t scalable. I wanted to build something real — something that could grow without me in the middle of every deal.
Enter: UpLead
In 2017, with no technical background, I hired developers on Upwork and started building. My wife was with me every step of the way. In fact, there would be no UpLead without her.
She was the original push behind going out on my own. She helped sketch the first version of the UpLead website on paper — wireframes we still have to this day. She believed in the vision before anyone else did — and without her, it never would’ve happened.
Our goal was simple
Help sales teams find in-market B2B leads with verified data — so they stop wasting time on dead contacts.
We bootstrapped UpLead from zero to over $1M in sales within the first two years. Since then, we’ve done $30M+ in total sales — all with a lean, remote team and no outside capital. We also built Signaturely, a simple eSignature tool now used by over 1 million people.
Along the way, I’ve started dozens of businesses — most failed. A few worked. But every single one taught me what I needed to learn.
This chapter is about giving back
Everything I learned came from books, YouTube, and making a lot of mistakes.
Now I’m in a new season — one that’s not just about building, but about sharing everything I've learned and what actually works.
Not fluff. Not theory. Just the real plays that helped me scale multiple businesses from scratch.
Here’s the kind of stuff I’ll be sharing:
How I built a $30M+ sales machine with cold email, cold calling, and no funding
The systems and messaging we use at UpLead to consistently book outbound demos
What works (and doesn’t) in modern B2B lead generation
Practical frameworks for sales, content, and founder-led growth
The lessons I wish I had when I was starting — and still rely on today
I’m not selling a course. I’m not launching a coaching program. This is just the part where I give back — by teaching the stuff I actually lived.
Who this site is for
This site exists for anyone trying to grow something real — whether you’re a:
Founders
building from scratch
Sales Reps
trying to close smarter
Marketers
pushing growth with limited resources
Operators
looking for proven systems that actually work
It’s for the underdogs. The self-starters. The ones willing to outwork and outlearn everyone else.
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Get tactical insights, growth strategies, behind-the-scenes lessons, free guides, and new videos — all from someone who built UpLead ($0 → $30M in sales) and Signaturely (0 → 1M users) without a dime of funding.
