The Crash-Test Dummy of Online Business

How Pat Flynn of Smart Passive Income built a successful online empire on empathy and connection

Pat Flynn, the mind behind the hugely successful (Source: Pat Flynn)

By Non Wels

If you’ve interacted with Pat Flynn of Smart Passive Income (SPI), even in the briefest of moments in a busy hallway at some vast podcasting conference, you know that he has a remarkable ability to engage with his audience — openly, honestly, and with the enthusiasm of Marty McFly punching eighty-eight miles per hour.

Flynn is known for connecting and engaging with his audience, but it’s also simply who he is — as a father, husband, entrepreneur, and human. It’s a connection that is wholehearted, without ego, and with a genuine drive to foster meaningful relationships. “That’s how engagement should be. It should be a way for you to connect with your audience, to empathize with them, to understand them, to listen to them, and to give them the answers they seek,” says Flynn.

His entire brand is built on empathy. As the self- proclaimed “crash test dummy of online business,” Flynn shares his successes and failures with his audience with an unabashed desire to help others. But achieving the role of online business crash test dummy takes time, effort, and sometimes a few unexpected stumbles along the way.

Check out this snippet from the fifth episode of the Hyperlink Radio podcast, where Pat Flynn talks about how to balance success with accessibility. Show Notes *** Subscribe on iTunes

After receiving his bachelor of arts degree in architecture from the University of California, berkeley, Flynn found a job working for a Southern California architecture firm, where he swiftly catapulted through the ranks.

A year and a half later, Flynn’s seemingly boundless energy and eagerness to be challenged inspired him to pursue more than what he had already achieved at the architecture firm, including an attempt at passing the Leadership in Energy and Environmental Design (LEED) Exam. After failing the exam the first time around, Flynn decided that wasn’t going to happen again, so he created a website that he and his co-workers used as a study guide to prepare for the exam on nights and weekends.

Like the Smart Passive Income blog and brand that would come later in the online business niche, the website Flynn created became the ultimate all-in-one LEED study source. He used it to take notes, add links to reference later, and organize all of the information he needed to pass the exam.

But everything changed in October 2008. Despite having rapidly climbed the ladder, becoming one of the youngest senior drafters in the company at twenty-five, working seventy hours a week, six months after his LEED study guide website launched, Flynn was laid off.

It was a stumble he didn’t see coming. “It felt like getting punched in the stomach times a hundred,” Flynn says. “I was upset, angry, and felt like a failure.” He had been working so hard, doing everything he should. but the crumbling economy had another story to tell. Flynn would be one of 7.9 million workers across the United States who lost their jobs during the Great Recession.

In what might be called a serendipitous turn of events, it was a podcast that helped propel Flynn out of that post-layoff haze. Listening to the podcast Internet business Mastery, he remembers a guest on the show who told a story about how he had managed to make six figures a year by helping people pass the Project Management exam. Hearing that story, everything clicked, and Flynn realized that his study guide could serve not just himself and his former co-workers, but thousands of others who yearned, like him, to eventually pass the LEED exam with flying colors.

“That’s how engagement should be. It should be a way for you to connect with your audience, to empathize with them, to understand them, to listen to them, and to give them the answers they seek.”

That website started as and eventually became what it’s known as today,, a study prep website that has seen 1.4 million unique visitors, 5.5 million page views, and more than 20,000 total paying customers since its inception.

Nearly ten years later, Flynn understands how integral that time in his life really was. In fact, he embraces every aspect of his career, from the lows to the highs. In Let Go, the book he wrote and self-published in April 2013, he highlights his journey from being laid off to finding success as an entrepreneur. Flynn is the first to note that without the recession and his layoff, he might never have found his way to his now-thriving business, Smart Passive Income.

“The layoff became a huge blessing in disguise, to motivate me not just to help myself by forcing me to see what other opportunities were available to me, but also to drive me to help others as well and help them realize there are so many opportunities out there for us,” says Flynn. “We just have to know that they are there, and that we have to make the choice to take advantage of them.”

After losing his job, he also realized that the work he had put into was laying the foundation for the “learn from my experiences” type of work he wanted to be doing and sharing with others. Testing ideas and sharing the results has become Flynn’s calling card, and has resulted in a brand — Smart Passive Income — that shows others how to embrace all of life’s experiences as potential opportunities for learning and growth. Flynn knows that it’s best to take a genuine interest in his audience’s experiences, because the experiences are what shape his audience, and what have shaped him.

Starting out as a personal blog, Smart Passive Income has grown into an essential resource for success in the online business world. Each week, features new blog posts, from Flynn’s personal exploration of lessons he’s learned to guest blog posts about search engine optimization (SEO), productivity, or countless other topics pertinent to online entrepreneurs. His weekly podcast, the Smart Passive Income Podcast, features extensive interviews with industry leaders, he has a web TV series called SPI TV, and, not to outdo himself, he also has a daily podcast called AskPat, answering questions submitted from his audience Monday to Friday. Through SPI, Flynn also publishes a host of free ebook guides and extensive how-to tutorials, hosts live Q&A sessions weekly on Facebook, and this year entered the online course space.

What compels his audience to start their journey in online business, what inspires them to keep at it, and what they are looking for to guide them toward success — all of it informs Flynn how he can further grow and develop the SPI business to best serve them. “I love that I’m able to help entrepreneurs at various stages of their business journey,” he says. “To fully meet their needs, I need to understand where they are in their journey and how they are connecting to my business so I can create strategies to serve each of them in a way that’s relevant and specific.”

Source: Pat Flynn

One recent way Flynn has served his audience is by creating two online courses, Smart From Scratch and Power- Up Podcasting. Each of these online courses is painstakingly handcrafted, borne out of Flynn’s personal experiences, the ups and downs he’s had running a business, to help guide students through two essential entrepreneurial building blocks: starting a business and launching a podcast. Flynn holds regular office hours for his students to give them a chance to ask him questions directly. And each of the online courses has a Facebook group so students can interact and find inspiration in each other’s failures and victories as a community, a tight-knit group, comrades in pursuit of a singular goal.

This genuine connection Flynn has with his audience is just the way he likes to operate. He has, over the past ten years, evolved from blogger to CEO of his own business. but his approach remains steadfast in wholehearted engagement. Early on, when Flynn was just getting started in his business,
 he decided that he would be the type of entrepreneur who responded to each and every comment directed his way. On social media. On his website. In email. In person. He answered every single question. He expressed his gratitude. He showed that he cared because he wanted to, and he felt it was the right way to run a business.

With the success of Smart Passive Income, that personal, connected engagement is just as important to him. However, now he needs a little bit of help with the volume of feedback he receives daily from the raving Smart Passive Income audience. “I couldn’t keep up, so I hired a team,” he says, adding that working with the teams at Winning Edits and Rocket Code and a virtual assistant helped him reimagine how his business could operate. “My team helped to swiftly establish processes that allowed me to continue to engage on a level that made sense for my workload, created editorial strategies that served my audience in ways that I never thought possible, and just made my life easier while making my audience’s lives better.”

As Flynn’s business has grown, even though he has a team to help with the output and audience support, the generosity, transparency, and joy with which he operates his business hasn’t changed. He connects openly with his audience on social media. He builds online courses to target specific needs his audience has expressed interest in. He pursues, seemingly without
 pause, new ways to ensure his audience is always learning and engaging and growing.

One way Flynn maintains this pursuit is with his fan-favorite monthly income report blog posts. Each month, he shares his monthly income report, which is a detailed and fully transparent look into his earnings, affiliate income, and, most important, the victories and failures he experienced the previous month. He shares these highs and lows to stick to his promise of being the “crash test dummy of online business,” because without the trust of his audience, he wouldn’t be able to run the online business he loves, explore new entrepreneurial adventures, and create diverse streams of passive income that afford him the time he cherishes with his family.

“I always have things on my task list, my mind constantly racing with bigger and brighter ambitions.”

And when he’s not running Smart Passive Income, he strives to focus 100 percent of his energy on engaging with his family, making crafts or science experiments with his kids, Kai and Keoni, or cheering on his wife, April, at the Disneyland half-marathon. He works hard to be there for his family both physically and mentally. “It means being there in the moment and appreciating every bit of it,” he says. “Sometimes it’s difficult to do this as an entrepreneur. I always have things on my task list, my mind constantly racing with bigger and brighter ambitions.”

Much like he shares his business struggles, he shares the difficulties of balancing life and work with his audience. He understands, more than most, that it’s his humanity that people are drawn to. The more human he is, the more people want to engage with him, which is why if you do run into Flynn in the hallway at a conference, you’ll likely be one of many folks waiting in line to talk with him. And that’s okay by him; he’ll always take the time for one-on-one conversations with anyone who asks.