Top iTunes Business Podcast

47+ Million Downloads

SPI 466: The Moment I Took the Entrepreneurial Leap

We go deep in this episode. We’re talking about the entrepreneurial leap—that moment when you accept the risk and truly dedicate yourself to the path of starting your own business. For me, it didn’t happen the moment I got laid off or even after I started making more than four times what I’d been making as an architect. It came later, after several eye-opening experiences and conversations with people I trusted. Today, I’ll tell you that story.

SPI 465: Making the Entrepreneurial Leap with Confidence with Gino Wickman
Rocket Fuel by Gino Wickman
Pat on Instagram
Pat on Twitter

You’ll Learn

Welcome to the Smart Passive Income Podcast, where it’s all about working hard now so you can sit back and reap the benefits later. And now your host, he’s got clubbed thumbs, but he likes to call them his Nintendo thumbs, Pat Flynn.

Pat Flynn:
Whether you’re an entrepreneur or not yet, in your head, I want to know if you’ve actually taken the leap yet. The leap, the entrepreneurial leap. Yeah, you could even be an entrepreneur and not yet take that leap. And I’m going to tell you a story here in this short follow-up Friday episode about the time I took the leap, and it didn’t happen when I got laid off. More on that in a sec, but welcome to the second Follow-Up Friday episode here on Smart Passive Income. This is a special episode that is now something experimental that we’re doing. Yes, we’re coming out with two episodes per week, the Friday episode, a follow-up to the Wednesday episode where we go in depth with a topic. And today we are going in depth with the idea of the entrepreneurial leap, because our guests earlier this week, if you haven’t listened to episode 465, I highly recommend you do that. That was with author Gino Wickman, the author of a couple of books, in fact. One of the most life changing books for my business was one of his called Rocket Fuel. This idea of the relationship between a visionary in a business, it could be you, the creator, the person who has the ideas, and the integrator, the person in your business who works with you, alongside you, or below you, if you will. As you do what you do on the front end, they’re helping you from the backend, and they’re the executer, they’re the online business manager. Again, the integrator. And this visionary integrator relationship is what Rocket Fuel is all about. And it’s what led me to feel very great about working with and even bringing Matt, my co-CEO now in SPI, alongside me to help execute on a lot of the big vision ideas that I have within SPI Media and within the brand.

So can’t thank Gino enough. I talked about that in the episode. And we interviewed him not just about Rocket Fuel, but we talked about this idea of the entrepreneurial leap and the different things that you might need in order to take that leap, the things that you can do to ensure that you’re going to be feeling okay when you do that and how to get support, and all those kinds of things. And what we do here on these follow-up Friday episodes is just me and you, I go deep and we talk about something that was discussed in that episode a little bit more deeply. And I wanted to tell you this story today about when I took the entrepreneurial leap. Now, you might know that I had gotten laid off in June of 2008. That was not a leap. That was essentially getting shoved off, if you will, and hitting the ground really hard and not really knowing where to go next.

And all I was trying to do when I hit the ground was to keep climbing back up that same ladder, the same ladder I was familiar with. Because in my head, I was so high up that ladder, and the higher up a ladder you go, the tighter you grip. And you can’t imagine letting go or trying something else, because you’ve dedicated your life to this, or at least your career, or even your schooling. And that was a hard thing that was there for me. I had five, or four and a half, if you will, years of schooling to be an architect. I got this amazing job in the Bay Area of California at a very renowned architecture firm working on some amazing buildings and designs and everything from casinos, restaurants, retail stores, et cetera. I mean, I had my fingerprint on so many buildings across the United States and that was my career and that’s what I thought I was going to do forever until I got let go.

But when I got let go, a lot of things happened. I fell into a little bit of a depression state. Didn’t know what I was going to do next. Was begging and pleading to go back into the architecture space climbing up that ladder again that I had once climbed before. Couldn’t imagine life anywhere else. And then I got presented with an opportunity. I had heard a podcast called Internet Business Mastery, and on that show, big, thank you and shout out to Jeremy and Jason, the hosts of that show. Very much the reason why I have a podcast today was because of them. They changed my life and I wanted to pay it forward and start a podcast to do the same for others. But on their show, I heard an interview with a man named Cornelius Fitchner, who I heard was helping people pass the project management exam and he was making six figures a year doing so.

And it just blew me away. That’s what inspired me to go and create my architecture website to help people pass the architectural exam called the LEED Exam, which stands for Leadership in Energy and Environmental Design. And that turned into the business that ended up making over $200,000 after monetizing that at the end of 2008. And it completely changed my life. It showed me that I could do it. It showed me that there were other opportunities out there to start a business, to do something of my own, to take control, to have more freedom with time, and to have eventually, not right away, but eventually some financial security. And it was amazing. But you might not know this. In March of 2009, this was several months after starting this business and the business was running and I was making $20,000 to $25,000 a month, which was five times as much as I was making monthly as an architect, yet I was still going in for job interviews.

I was still daily trying to make my resume look better. I was still daily calling around seeing if anybody had any open positions. And I remember vividly going to different architecture firms in the San Diego area. I was living with my parents at the time. I had moved out of my apartment to save money, because I had gotten let go and I had to pay for this wedding and there was a lot of things. It was multi-levels of bad timing. But I remember vivid memories of going into architecture firms, sitting down, and hoping that I would get every question on their AutoCAD Test correct, because I just couldn’t imagine doing anything else. I had been so conditioned to believe I was supposed to be an architect from the years of schooling to how much I was excelling in the architecture career that I had. And even though on the side I had this business that was booming, I still went in for job interviews.

And it was interesting, because every time I got told that they weren’t going to hire me, I felt like, well, this isn’t good enough. I need to try again, that I maybe had lost my touch. At the same time, I had my dad who is very supportive and has always been, he was telling me something that was his version of support, which was, “Hey, you can go back to school. You can go get your master’s degree. You could come out better on the other end and get an even better job. And this thing that you’re doing on the side, I mean, it’s risky,” was something that he said, I remember. I remember sharing this story online when people started to catch wind of my story and I was featured on a podcast called Entrepreneurs Journey with Yaro Starak, and I remember getting a lot of great comments on that podcast episode of his. But then there was one comment that said, “This guy’s just a flash in the pan. He’s going to go back to architecture in no time.”

And I read that and I was like, “Yeah, he’s probably right.” So even though I was doing business, I was not yet somebody who had taken the leap. I was still straddling two positions, two sides. It was as if I was on a new ladder, climbing the new ladder, but still with one foot on the old ladder. How in the world can you climb a new ladder if you still have a foot on the old one that you’re trying to leave behind? But I didn’t want to leave it behind, because that’s all I knew. But then I started to get some advice. I started to reach out to people and mentors who could help me grow my business more and I started to notice more and more the freedom of time and the ability for these people who were my mentors to connect with other people, to inspire other people, and not do it at a nine to five job, but do it as an entrepreneur.

And there was one person in particular, actually it was Jeremy from Internet Business Mastery—he’s such an important figure in my life who had helped me get to where I’m at today—we sat down at a Cheesecake Factory in San Diego. We had lunch together and I was telling him about my business and how it was going, because he was there at the start. I joined his Academy and all this stuff, and he was asking how it was going. And I said, “Business is going well, but I’m still looking for jobs.” And he said, “You know what? If you get another architectural position, you might be happy. I hope that if that’s in fact your life goal and your dream that that’s what you do, and I hope you get the next job. But if you go down that route, your business will not grow. It just won’t.” And I knew that to be true, but when I heard it from somebody else, it made complete sense.

And then he said something that really resonated with me. It was actually a question. He said, “Pat, how many thank yous have you gotten lately from your business and the things that you’re doing with helping people pass this exam?” And I told him, “Yeah, I’m getting emails every single day. People passing their exams, people saying “thank you”, people calling me by name,” which was different to me. I was just this guy on the internet blogging about passing this exam. There was even a woman named Jackie, who I spoke about in my book Superfans who actually said, “I’m your biggest fan.” All I did was help her pass this exam. But Jeremy then followed up with, “Well, how often did you get thanked and recognize when you were doing architecture?” And you know what? I couldn’t come up with an example. There were none.

And there were probably times when my project manager would say thanks for the blueprints or the CAD drawings, or whatever. But there were no moments where I knew that I was actually helping somebody, really, or changing a person’s life in the way that it seemed like I was doing it through helping people pass this exam, because people were getting raises and getting promotions. And Jackie specifically had mentioned that she was able to take her family to Disneyland as a result of her promotion. And later, this is not something I knew at the time, but later, and I spoke about this in Superfans, she had actually told her entire office to buy my guide. All 25 people in the office had been a customer as a result of this one person who I had helped. And like I said earlier, I have my fingerprints on so many different buildings in the United States, including Hawaii, in fact.

Now, my wife and I, we were married on February 21st, 2009, and we went to Hawaii on our honeymoon. And I remember we were walking down one of the main streets, this was in Oahu in Waikiki, and there’s a lot of beautiful buildings, and, of course, as an architect, somebody who’s just still engulfed in that world at the time, I was looking around, I love looking at buildings. And we’re walking down one of the streets and I just have to stop, because as we’re walking down the street, I notice a restaurant, a P.F. Chang’s, that I recognized. And, again, this was my first time in Hawaii, but I recognized it, because it was one that I had designed myself. The exterior, I remember specifically being in Photoshop. I remember the exact pattern of the chair material, the specific pendants that were used, and exactly where they were on top of each of the booths inside and outside.

The specific color, the specific material of the exterior, all of it, I just recognized it, because when you’re that deep into a project, you get very close to it. And so I just stopped there and I look inside and I look around. Inside there is so much noise, I’m sure, with the restaurant serving their patrons, people sitting and having conversations at their booths, the people behind the bar pouring drinks, the manager in the back calculating receipts, people dining outside right near where I’m stopped. And then people walking up and down the street not paying any attention to the store at all. And it made me realize in that moment that nobody there would ever know that I had anything to do with that building, nobody. And that was a moment where I realized that online as an entrepreneur helping a few people pass an exam that most people have never heard of before, they’re becoming fans of me. They’re supporting me in sharing my book and my study guide with other people. They’re recognizing me for the work that I’m doing.

And that was a big moment for me, because that was a moment while in this amazing state of euphoria with my new wife and my family that we were starting, it was just incredible to have all that happen at the same time. It was fate that I walked down that particular street. And it was interesting, because we were walking a very long way, it wasn’t near our hotel. We just were taking a stroll and loved the scenery. A couple of months later back in San Diego, business is rolling. It’s growing even more. I also have this new website called Smart Passive Income where I’m teaching a lot of this stuff to other people, and just being very open and transparent about what I’m doing and what I’m earning and what I’m spending and what’s working and what’s not. And I get a phone call, and I get a phone call from the boss who had let me go. His name was Iman, and Iman calls me and he goes, “Pat, I hope you’re doing well. I hope everything’s okay. How are you?”

And it was nice to get a call from him to check up on me and to see how things were going. But he had other intentions as well. He was calling because he wanted me to come back and work for him. He had ended up leaving the position he was in and he started his own firm. He was able to take a couple of my coworkers, some of my best friends when I was at work, people who I could peek over the stantion, the cubicle, and have a conversation about last week’s game kind of people. They were working for him. He even promised me my own office. I never had an office before. He even promised me that if I were to come up to Irvine, California that he would pay for me and my wife for one year for rent. He really wanted me to come work for him. And interestingly enough, and almost as a surprise to me, it didn’t take me more than a few seconds to say, “Iman, thank you so much, but no thanks. I’m good. I appreciate the offer.”

And I didn’t hang up on him at that moment, but I think he was taken aback and he started asking questions about what I was doing and he was very nice about it. He was very proud that I had been able to stay afloat, and I think that he really did care about what I was doing. I think he was a little disappointed, or at least surprised, but that was the moment that I took the entrepreneurial leap. And when I took the entrepreneurial leap, that was the moment I let that last leg go from that other ladder, the corporate ladder, and I was fully on this entrepreneurial ladder now. And the beauty of the entrepreneurial ladder is that it goes up, and up, and up. And there is no ceiling. There is no limit. And I’m very grateful that I got laid off. So, for me, it was a moment. For many others, I know there are moments as well.

For others, you might have breezed by that moment and you look back and you go, “Wow, look at where I am now,” or, “Look at what I’m attempting to do now.” And that’s so great. And for all of us, you listening while on a run or at the gym or in your car or while doing chores or just hanging out in the living room, maybe you have other family members listening to this at the same time, I’m just here to tell you that it does require some letting go in order to move higher and grow into a new space. As we discussed this past week with Gino, there are safeguards that you can put into place and support systems, and essentially, often the worst case scenario that we think might happen is not even a part of the scenario. It’s just our brain trying to make up these stories. But you have advocates in your life who could support you.

Perhaps you might want to save up a little bit. Or perhaps you actually know deep down that if you did make the leap, that you could grow even faster and get to where you want to go even quicker. And it’s not about working hard, it’s about working smart. Thank you for listening to this Follow-up Friday episode of Smart Passive Income. I hope you enjoy them. And if you do, if you’re listening to this and you’ve gotten all the way to the end here, let me know how this story has impacted you. Find me on Instagram, send me a quick DM, or on Twitter, same thing, or just message me @PatFlynn. And I look forward to hearing what you think. Let me know what you think about these Friday follow-ups. I think I’m liking it, because we’re going to go deep here. Thank you. And, again, if you haven’t listened to the last episode with Gino Wickman, episode 465, do it. Thank you so much. I appreciate you. And as always, Team Flynn for the win. Have a great weekend.

Thanks for listening to the Smart Passive Income podcast at

Share this post

Smart Passive Income Podcast

with Pat Flynn

Weekly interviews, strategy, and advice for building your online business the smart way.

Get Unstuck in just 5 minutes, for free

Our weekly Unstuck newsletter helps online entrepreneurs break through mental blocks, blind spots, and skill gaps. It’s the best 5-minute read you’ll find in your inbox.

Free newsletter. Unsubscribe anytime.

Join 135k+