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Exactly How I Landed My Most Lucrative Freelance and Consulting Deals

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How I Made $500/article

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My internal dialogue harangued all hope of focus as I bit into an eggs benedict at a Ritz Carlton next to a DC journalist my age. The journalist wrote professionally for a small yet high-paying publication. I coveted his job. The two of us were a part of a cohort of young entrepreneurs, lucky enough to be selected for a week long conference in southern California. At the breakfast table, the journalist and I spoke and I mentioned my Medium writing experience and Entrepreneur’s Handbook. He said that sounded similar to an editorial beat the publication covered about American small business owners. I asked the question I had been thinking about all week. “Could I contribute?” He said he’d introduce me to the editor-in-chief. From email introduction, to phone call, to initial pitches — a month later, I was paid for my first article of dozens to come.

How I Made $1/word

At 6:00 a.m., I walked into a men’s Christian group in Menlo Park with a friend. I poured a cup of coffee and struck up a conversation with a tech startup veteran with a deep network. He was friends with the organizer of a one-day digital marketing conference in San Jose, California. I told him I wrote for Inc. Magazine. He said there would be great people and stories at this conference in San Jose. He gave me a free press pass. At the conference, I listened to a session by one speaker who led the editorial team for one of the world’s largest banks. I caught him during a break and we spoke for less than two minutes and exchanged contact information. Two weeks later, we emailed, set up a call, and discussed content topics. After the call, he introduced me to a team mate who added me to their 14-step writing and editing process in Contently. I submitted my first rough draft and I was paid $800 immediately.

How I Made $3,000 for 8 Articles in a Month

The younger brother of the pastor I met at a church plant in Salt Lake City worked at a fast-growing startup. He headed up their marketing analytics. After a double date with our wives at a Cafe Rio, they invited us to compete in a Spikeball tournament. We went. My wife and I took second place. A couple weeks later, the marketer invited my wife and I to join his wife, friends, and dog on a mountain hike. On the trail, we spoke in depth about his job. He said his company was looking for a freelance blogger and that he would mention my name to the director of marketing. He introduced us over email, which was followed by a phone call. Sitting in my car outside a Starbucks, I told stories about articles I had written about interesting small business owners, which were their target audience. I told a dialed-in story for every question I was asked. I came across experienced, professional, and confident. It was one of the best interviews I had. We signed the contract a week later.

How I Made $55/hour

On a rainy day in Washington, DC, I walked into a meagerly attended conference. The number of empty seats in the huge auditorium suggested something was horribly miscalculated. Dillydallying in the foyer, I visited the merchants at their booths who showcased their relevant services. Behind one table stood a CEO with a staff member. We chatted at length, both grateful for a semi-interesting conversation to occupy the slow-moving afternoon. At the time, I was employed by a digital agency and aimed to land him as a client. Weeks and meetings later, the deal ended up falling through, due to inadequate budget (or overpricing, you decide). But for the next six months, I stayed in touch with the CEO. We had developed a trust. He bought my novel and followed my blog. Months later after I had quit my agency job, I called and asked if he needed content marketing help. He said yes. We chatted about scope and strategy and I wrote a proposal. He added me to his remote payroll and I consulted with his marketing team.

How I Made $75/hour (first time)

At a former employer, I was the director of marketing, a job I had carved out and pitched to the company (that’s another story). Four and a half years later, once I became independent, they reached back out to me to help keep up their email marketing campaigns. This newsletter was my baby. I had created the voice, process, content, direction, and design of these campaigns back when I worked there, so I was the originator and the perceived “expert.” Knowing the company didn’t have anyone to do it or to trust to do it well, they reached out. I replied with a micro-proposal in an email. Knowing my value and time, I gave them the highest hourly rate I’d ever proposed. They accepted. This changed the course of my consultancy work forever.

How I Made $75/hour (second time)

A rising tide raises all boats, so once I received this higher hourly rate, it showed me what I was worth, and what I could charge other clients. So when the content lead and wife of a former college hall mate reached out while I was in Salt Lake City and asked for help with her nonprofit’s content marketing, I knew which rate to propose. Fortunately, the nonprofit wasn’t the typical scrappy, cash-starved nonprofit with zero money in the bank. It’s more of a “venture philanthropy” organization backed by some of the world’s wealthiest donors. I quoted $75/hour again. We worked on monthly scope, signed contracts, and I began working with her organization promptly.

How I Made $100/hour (first time)

At a men’s retreat in Monterrey, California, the main speaker, a multi-exit serial entrepreneur and reified startup CEO, shared his life story. It was riveting and emotional (I hope to share it one day, but right now it must be kept private). After he spoke, I approached him and asked if I could share his story. He said yes. We met at his company’s headquarters and chatted further. He liked me. I looked up to him. I wrote up my notes from his talk and shared it with him. It brought tears to his eyes, he said. But it wasn’t time to share. Instead, he called me and said, “Let’s work on other stories.” Turns out, he’s a writer himself and needed editing and shaping help. “I’ll pay you a hundred dollars an hour,” he said. I didn’t say anything and he continued talking about the work we could do together. As he talked, I tried to imagine this rate and how it would change my career. I never would have imagined making $100 an hour as a person who grew up in a poor home, with a single-income parent, homeschooled with my three brothers. We almost never wore new clothes and qualified for subsidized lunch in high school. Assuredly, I grew up happy and well cared for (you don’t need lots of money to prosper). But I was never exposed to making lots of money. Even in college, I thought a $40,000 salary was plenty. All this was tumbling through my mind as the CEO spoke on the phone. We hung up and I was shaking with excitement. The first time you make a three figure hourly rate, it’s a major confidence boost. After signing an NDA, we began the work.

How I Made $100/hour (second time)

The first time I made $100/hour, it fell in my lap. A blessing from above. The second time, I asked for it. The sun splashed on my face on the rooftop of a midrise in east San Francisco. I was attending another one-day conference, covering the speakers on behalf of Inc. Magazine and Entrepreneur’s Handbook. I filled my plate with food from the buffet and found an empty space in the corner next to a man in a three-piece road-sign blue suit. We struck up a conversation. Unsurprisingly, he wrote about fashion and business for Forbes. We talked shop and fenced back and forth on client placements and content deals. A few weeks later, I wrote a one-off profile of one of his clients. Fast forward six months. He cut ties with the client and told me the news over Instagram. With his permission, I reached out to the client to see if they needed PR help. Sure enough, they did. The price I gave them? $100/hour. This sparked a negotiation and we agreed upon a customized incentive package that worked well for both of us. My writing rate remained at $100/hour.

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