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From Dropping Out of College to Building a $5 Million Email Platform

William Cannon, founder of email marketing company UpLead, epitomizes the American Dream. A college dropout from a low-income single-parent household in Southern California, Will not only stayed afloat despite being a mortgage broker during the 2008 housing crash, he’s been a pioneer in the field of email marketing for almost twenty years.

This is the story of how a not-so-average kid with a big dream and his high-school sweetheart worked together to make it all come true. Creating an email marketing company with 22 employees, a run rate of over $5 million, over 3,000 paying customers, and VCs clamoring for space in his inbox. Entirely bootstrapped. 

A Pioneer in Email Marketing

Will attended college for two days before dropping out to work in real estate. He still thinks it was a great decision.

“I wanted to get out there and start building and making income,” he says. “I didn’t want to wait and college wasn’t fulfilling me financially.”

Will credits his impatience to growing up in a low-income household. He was used to working for the things he wanted in life.

“I wanted lots of things growing up like new shoes and other stuff and I just learned you got to work for it,” he says. “I think it gave me this drive and fire to want more and to pursue more. A little fear inside to make me keep pushing. This had a huge impact on me.”

Instead of studying, then 19-year-old Will followed his girlfriend into the real estate industry and made his own business. Barely 20 years old and with only a high school diploma, he was confident of success. “Real estate was booming in the mid-2000s so everyone was getting into it,” says Will. “We were young and didn’t know what we were doing and there was a ton of money in it. We didn’t need a degree.”

Will started his own real estate mortgage business when he was only 19 years old

Will’s real-estate venture evolved into a mortgage company around 2005 and 2006. To source clients, Will and his loan officers had to do a lot of cold client outreach — a long and tedious process in an age where computers were only just starting to become the norm. However, Will quickly came up with a new system years ahead of its time.

“Email marketing wasn’t really a thing back then but I started creating email campaigns and compiling lists of people to email,” says Will. “Colleagues started coming up to me saying, ‘Hey how did you get that list?’ And so I would sell my lists to them on the side.”

As we all know, the real estate bubble popped and brought the whole market down with it in 2008. But Will and his email lists were only picking up speed. He made a pivot into full-time email marketing in 2007 and created the beginnings of UpLead.

UpLead Was Forged in a Decade of Trial and Error

Will spent the next decade two steps ahead of the email marketing curve at his company, BWG Marketing.

“I had to learn everything from scratch,” says Will. “Initially I only knew cold email outreach. Over time I realized we needed a diverse range of channels like SEO and PPC. Today most of our customers are actually from referrals and they know our brand. The way I look at it, if I can get one customer I can get ten and if I can get ten I can get a hundred.”

Through trial and error in the increasingly saturated industry, BWG marketing established a name for itself in the email marketing space. By 2017, Will saw tech increasingly moving into the email marketing scene and a growing need for better quality email leads so he pivoted again. In 2018, UpLead was born.

How UpLead Took Email Marketing Somewhere New

Today there are hundreds of email marketing services out there with huge databases of emails for cold outreach. The way UpLead differentiates itself is by the accuracy of its leads.

“Instead of just providing contacts we want to provide more information on these contacts,” says Will. “I want you to know who is specifically in the market buying your services. We have high-quality data and we have a great database of contacts and companies.”

Massive email lists scraped from every corner of the internet are ineffective if they don’t lead to anyone. Without verifying if the email is correct, it becomes impossible to track the real read rate of sent emails. This in turn makes it hard to track campaign effectiveness because the reason you’re not seeing leads is because no-one is reading the emails. He created UpLead to make sure you never send an email to a dead address.

“When we started, we would use tools from other companies to verify our lists but then we decided to build a tool for that too,” says Will. “Today, the moment you export an email list from our service we run it through a verifier so you don’t waste time emailing dud emails. In 2017 and ‘18 no one else was doing that.”

Today Will believes UpLead is right where they need to be despite massive competition.

“We’re in a place where product-market fit is already reached. There are multi-billion dollar companies in this space, so we’re not in a position of, ‘I’m not sure if this will work,’ it’s just more about, can we get enough eyeballs on UpLead?”

Despite achieving profitability, Will’s new business model is still in the early stages and he is very open about the areas he needs to improve: “Right now it’s a bit of a stressful time. We’re switching payment providers because of errors and we’re in talks with Stripe and stuff,” he says. “I think managing and hiring people is tough. I don’t have a ton of experience managing and a limited amount of time in the day. I have two kids: a seven-year-old and an 11-month-old and our whole team is remote.”

Today the business they built has about 22 employees and is still growing strong.

“There’s been lots of momentum since we started,” says Will. “There are still ups and downs. Times do get stressful. But we push through.”

Is There a Mrs. UpLead?

Will credits his wife and longtime partner for not only his business’ success but his success in life.

“We met through a mutual friend when we were 16 or 17 and didn’t know where it would go, but we’ve been together ever since,” recalls Will. “I’d say she’s truly my cofounder. When I went into real estate I was following her because she had just gotten her license. She’s also been an integral part of our business today and even picked the name UpLead. I remember when we were working on the initial website, she helped do all of our wireframes. We’re kind of a team.”

Staying Bootstrapped Despite Multi-Million Dollar Offers

Being on the top of email marketing for nearly two decades, UpLead has naturally drummed up more than a little VC interest.

“In the past year or two VC firms started reaching out and I initially shut down all conversations,” says Will. “At one point we had an offer to purchase for $13 million. I declined because the business was growing and I knew we’d be more valuable in a year or two.”

That’s not to say Will is opposed to selling. He has even brought UpLead to market before.

“At the beginning of this year, [2021] we took it to market,” he says. “We had a number that we thought the business was worth and one bidder came in with a very high price to stop our bidding process. We went exclusive with this PE firm but they were buying 50-60 percent and I was essentially going to be an employee.”

This deal did not sit well with the lifetime entrepreneur used to being the master of his own fate. “I love being bootstrapped and not answering to anyone. I don’t want a boss,” says Will. “We’d look at offers and we’ll consider them but we’re happy doing our thing.”

When asked about what advice he’d give to other bootstrapped entrepreneurs, Will believes marketing is an area new startups rarely get right.

“Interview your customers. Get on the phone. Learn what led them to use your product and get that testimonial when they’re done.”

“I think if you work with a VC firm you will have some guys sit you down to talk about branding, but being bootstrapped you don’t think about it,” he says. “As a bootstrapped startup you need to think about product-market fit. Interview your customers. Get on the phone. Learn what led them to use your product and get that testimonial when they’re done. Some of the best marketing you’ll do will be from customer referrals.”

In an era where many believe the American dream has grown tired, It’s refreshing to hear a new take on the college dropout turned successful entrepreneur story. One from a man of humble beginnings who fell into his calling by putting himself out there and doing. A man who continues to chase his own version of success instead of dollars because he values freedom more than anything else. Stories like this need to be told.

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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