Second Flight Consultancy

Nick Cullen's entrepreneurial journey started at age 13 when he discovered an early growth hack on YouTube. Noticing that popular music videos generated massive comment engagement with visible timestamps, he realized he could leverage this attention to connect fans with similar artists. He built an automated tool that grabbed YouTube URLs, personalized messages, and sent them to potential fans—charging bands $25 each to manage their outreach. At his peak, he was managing around 20 bands and earning $1,000-2,000 monthly, eventually making $20,000 total from the venture before finishing it at age 16.

This early success led to legitimate employment offers. By 17, he landed a sales and marketing role at a golf resort in Northern Jersey (earning $55,000 plus commission), which he hustled for through persistent cold outreach—even sending donuts with a note saying "my sales are sweeter than these donuts." He pivoted through several high-level positions: selling gym memberships at Equinox in Manhattan, handling major accounts at Time Warner Cable Business Class, and working at the startup Booker, where he helped grow the company from 25 to 150 employees. By age 22, he'd landed the highest-paying safe job—a financial services role paying $120,000 base plus $50,000 annual bonus—handling business development operations.

Despite the lucrative corporate role, Nick felt profoundly unfulfilled. He kept telling his girlfriend (now wife) that the money wasn't worth the lack of purpose. The turning point came when clients began asking him for advice outside his formal role. He was talking to clients about what he actually knew—marketing and how to grow tech businesses—and they found it intriguing. Word spread, but his employer grew suspicious, thinking he was building a competing business using their clients.

Instead of continuing to hide it, Nick decided to launch Second Flight Consultancy in 2014. He chose the name deliberately: every business owner he met wanted to get from point A to point B, and like a long flight, most journeys needed a "second flight"—a connecting strategy to reach the destination. He got fired on the Fourth of July weekend and entered a five-month grinding period before landing his first client in November.

Nick's 2014 revenue was humble: just $12,000 (accounting for his five-month startup period). Word-of-mouth from his previous corporate clients who'd asked for advice became his initial customer source. His background in sales—from the golf resort, Equinox, Time Warner, and corporate BD—gave him the skills and mindset to pitch effectively and follow up relentlessly.

He focused on results-driven strategies rather than vanity metrics. Where most agencies promised followers and engagement, Nick asked: "How many of your followers are actually buying from you?" This sales-centric approach resonated with business owners tired of fluff. His typical client engaged for 12-14 months at around $5,000+ monthly, depending on the number of campaigns. The key was delivering real revenue-driving results so clients wouldn't want to stop.

The breakthrough came when Nick developed an AI sales robot that prospected on LinkedIn and automated meeting setup. This allowed him to scale beyond his personal hustle. He also built a complementary Academy—a coaching product for entrepreneurs who couldn't afford full agency rates ($5-10 students per month, generating roughly 30% of total revenue by 2016).

He assembled a lean, remote team of 10 across San Francisco, Tampa, Boulder, and London, hiring intellectually aligned people who could handle client strategy calls and conversations. The agency model kept costs low: with typical $5k/month clients, the agency retained about 70% of revenue after project costs, while people remained the primary expense.

By June 2016 (during this interview), Second Flight Consultancy was running at $60,000-$100,000 monthly, putting them on pace for roughly $800,000 in 2016 (half-way through the year) with a full-year projection of $1.3 million. Nick was retaining approximately 50% of revenue as profit—roughly $650,000 in cash flow from $1.3M in revenue—an unusually healthy margin for an agency. His strategy centered on actual results and revenue impact rather than metrics, positioning Second Flight as a counter to agencies focused on vanity.

At 26, married with one child and ambitious for more, Nick had gone from unfulfilled six-figure employee to profitable agency founder in just two years, proving his own thesis: "Don't wait. Just start your business."