Aunchport

Landon Ray's entrepreneurial journey began unconventionally. After selling flowers at farmer's markets and playing in a band, he hit a quarter-life crisis at 25 in 1996. Inspired by the Silicon Valley tech boom—Yahoo at $12, Cisco rising—and unable to break in as a college dropout non-engineer, he discovered day trading. He borrowed $50,000 from his dad and moved to New York to learn stock trading. By 2000, he was making millions annually, but the 2001 crash cut his income by 90%, from "a couple million dollars" to "100 grand for more work." He walked away.

After taking a few years off to start a family, Landon co-founded an SEO business in 2004. The business worked, but he quickly realized SEO was fragile—"one day, Google was probably going to take away all my results." However, the experience forced him and his small team (just himself and two recent college hires) to learn online marketing and direct marketing strategies. They discovered no tools existed for what they wanted to implement, so they built tools internally. By 2006-2007, Landon realized the SEO business wasn't his future, but the tools they'd built were gold.

The pivot was brutal. From 2004 to March 2009—five years of "abject, horrible failure"—Landon invested "hundreds of thousands of dollars" while taking no salary, living off savings. They launched flops in 2007 and 2008. A third version in 2009 finally gained traction. "It wasn't till, till like March, April of 2009 that it really started going."

When Aunchport exploded in 2009, the company had the right product at the right time. By 2016, they'd grown to 6,000 paying customers and over 10,000 total users (including free tier). Pricing evolved dramatically: they'd originally charged $1,600/month because they "didn't have the wherewithal internally to support clients for less." Over time, they improved documentation, support, and UX, dropping prices to $79-$597/month, with an average customer paying around $400/month. They later launched Entrepages, a free landing page builder at $15/month premium, which skewed metrics lower but expanded their addressable market.

Unlike most SaaS companies, Aunchport stayed profitable. Landon credits their lack of VC money—raising only ~$3 million in equity from "old Wall Street friends" over 10 years—forced them to grow sustainably. "How do you not be profitable?" he asks, pushing back on Silicon Valley's "bleed money to win" playbook. They've made "504 years in a row" of profitability (likely "50% growth"), reaching approximately $14-20 million in ARR by January 2016.

By 2016, Aunchport employed 100 people, all based in Santa Barbara. Landon stayed true to his commitment to leave at 5:30 PM daily to be home with his two kids—a discipline that likely helped the company's focus and culture. The biggest challenges: learning to scale operations (his weakness, being visionary-oriented), managing engineering departments, and balancing profitable growth with expansion. Landon owned most equity, with co-founders (his college hires, now CTO and Chief Architect) and a president holding significant stakes, plus 10% in an employee stock option pool.

When asked about a hypothetical $100 million acquisition offer (roughly 5X ARR), Landon declined, noting unrealized opportunities: they'd never run paid customer acquisition until "a few months ago," representing "an extraordinary opportunity." He was open to smaller strategic investments—potentially 20-30% equity to a buyer like Oracle. His philosophy: build a business you love, serve your market, and don't chase exit multiples at the cost of mission.