Summary
Highlights
Will Cannon recounts his childhood growing up in a single-parent household and his early entrepreneurial ventures, such as selling burned CDs. He shares his experience working in various jobs, including at Sears and a collection agency, before getting into real estate during the subprime mortgage boom. He learned valuable lessons about hard work and the importance of timing by starting his own mortgage company with his then-girlfriend (now wife).
Will details the early success of their mortgage company, driven by aggressive cold calling during a period when obtaining loans was easy. They made significant money, but the 2008 financial crisis led to the collapse of their business, leaving them with foreclosures and repossessed assets. This hardship sparked a new idea: capitalizing on the demand for lead lists, which they had used to recruit loan officers. He observed a company called Listguy.com selling similar lists for $200,000 and decided he could build a similar business.
Will launched "The Data Supplier," a website selling categorized lead lists. Within months, it was generating $30,000-$50,000 per month through gray-hat SEO and cold emailing. This organically evolved into an agency model, providing clean B2B data and cold email/calling services for a decade. He recounts facing a challenge when his first attempt at building a SaaS platform was scammed. Five years later, motivated by long work hours and accumulated assets, he successfully launched a B2B SaaS focusing solely on that niche.
During COVID-19, Will sought to build another SaaS. After extensive research on G2, a B2B software review site, he identified the e-signature market as ripe for disruption. He noted that only 1% of documents were signed electronically, indicating immense growth potential. Observing that major players like DocuSign and Adobe Sign were criticized for complexity, he decided to create Signaturely, an e-signature tool designed to be "stupid simple." He leveraged his SEO expertise and a freemium model to attract users, quickly gaining over 100,000 users in the first couple of years, with most still on the free plan.
Will shares insights into future business opportunities, particularly in vertical SaaS. He envisions a future where lead generation and customer acquisition are highly automated. He suggests building industry-specific CRMs (e.g., for dentists or barber shops) and offering the software for free, monetizing through ancillary services like credit card processing, payroll, or health insurance. He highlights that these services often yield higher profits than the software itself, creating a win-win for businesses and their clients.
While acknowledging the lower barrier to entry for building software with no-code tools, Will cautions against underestimating the challenges of scaling a SaaS business. He emphasizes that reaching millions in ARR requires more than just a functional product; it demands profitable customer acquisition strategies, brand building, and addressing complex compliance issues. He advises aspiring entrepreneurs to focus on acquiring customers profitably and building a mini-brand, and to even pre-sell their ideas before investing heavily in development.