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SPI 474: My First-Time Hire Story (And How Much I Tried to Avoid It)

Today we’re going to jump back in the DeLorean and go all the way back to when I made my first time hire. Now, this wasn’t a long-term hire or a team member, but I learned a lot of valuable lessons in the process (some of them kind of embarrassing, to be honest). Making that first hire was really the unlock for me in a lot of ways: my entire mindset shifted from “they want to charge me how much?” or “I can do that myself!” to understanding the return on investment that was possible.

If you didn’t listen in earlier in the week, I sat down with my assistant of seven plus years, Jess, to discuss how to create positive relationships with executive assistants ( Today’s conversation — our follow-up Friday, if you will — is an extension of that episode.

Ultimately, you just can’t do everything on your own, and once you realize just how much more you can do by outsourcing, hiring, delegating . . . so many doors open up. So let’s sit back, relax, and I’ll tell you the story.

You’ll Learn


SPI 474: My First-Time Hire Story (And How Much I Tried to Avoid It)

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, his AOL instant messenger screen name was FatTrickFlynn: Pat Flynn!

Pat Flynn:
I’m remembering what it was like to hire somebody for the first time. So we’re going to go into the Delorean, back to 2008 when I had just started by website at, which later got changed to This is a website that was built to help people pass an architectural exam. The first business, and I created it after getting laid off from my architecture job, and I had created a written study guide that I published. It was just a PDF file sold online and it did fairly well, and it was all done by me. I was very proud of that. Proud of that fact that I was able to recover from getting laid off. Proud of the fact that I build the website myself. Proud of the fact that I wrote this study guide myself, that I published it, and that yes, through a little Q&A, helping myself by asking for help, I was able to get it done. But it was built all by myself. All the graphics were done by myself. Even the logo was created by myself. Again, I was very, very proud of that.

Fast forward a couple months, we’re in now December of 2008. I just filed for my LLC and taking this thing seriously now, and my son was about to be born. So I was quite motivated to see what else I could do to generate additional income. I decided that in addition to the study guide that I created, that I was going to create an audio version of the study guide. And I was like, “Okay, well, I have a microphone. I can do this myself.” I had gone to a friend and I told him that I was going to be doing this. I said “Hey,” and this friend was in online business, too. And I said, “Hey, I’m going to be creating an audiobook.” And he said, “Okay, who are you working with to do that?” And I said, “What do you mean, ‘Who are you working with?’ I’m going to be recording it myself.” And he said, “Oh, okay. Cool.”

I didn’t understand why he, number one, asked that question, and number two, why he reacted this way, but I was motivated because I knew that if I had this thing that was providing value, that it was an audio version that I could sell either on its own for people who didn’t want to read my audiobook, for people who would want to go to sleep listening to this information, or listen to it in the car or whatever, or I could potentially sell it in combination with my ebook, that it would do really well. I was quite motivated. I took my microphone, I had a Logitech gaming headset. I didn’t know anything about audio at the time. And I put it on and I remember spending three whole days, probably four to five hours each day, in my parents’ house in my old bedroom when I was a kid, because I had moved back in with my parents to save money at this time because I had just gotten laid off, and recording this thing.

I recorded it. I think it was, geez, what was it on? I think it was legit in Microsoft Sound or Voice Recorder. I don’t even remember what the app name was, but it was the generic app that came with the PC or Windows. And I think it was an old version of Windows, too, like Windows 95 or something. Anyway, this audio recorder, I recorded a separate file for every single chapter. There were about 56 different chapters in this book. It was, again, a study guide for a very difficult exam in the architecture space. I remember playing it back when I was done. I was quite proud that I had finished it, and then I had listened to it from the beginning and I just fell to the floor. I couldn’t believe that I had spent three days recording something that I couldn’t even listen to because the quality was so bad. And even though I was just reading from this book, I was just not happy with it at all.

I was having random pauses, it just was scratchy. Again, I didn’t know what I was doing. I hadn’t really involved myself with podcasting other than listening to it at the time. But I did have some audio equipment as a result of wanting to start a show, but again, this was just me trying to record a book. Didn’t work. So I felt like I wasted three days. I went back to my friend who was also part of another group. This was a part of Internet Business Mastery. And I asked him, I said, “Hey, how do you record an audiobook and make it sound good? Because I tried for the last three days to record my book and it sounded terrible.” I remember in the forums there was a bunch of LOLs, LMAOs, ROFLs – rolling on the floor laughing. And people who responded, we were all friends and we like to joke around with each other, but I wasn’t feeling very good. I was like, “Why are you guys laughing at me?” And they basically said, “You’re trying to record this on your own? Are you crazy? You don’t even have any audio experience.”

And I said, “I know, but I know how to talk. I can read and I have a microphone.” And they were like, “What kind of microphone do you have?” And I said, “Well, a Logitech gaming headset that I use when I play Quake II.” And they started laughing even more. Well, they eventually opened my eyes up to the world of virtual assistance and getting hired help. In fact, there was a website that they introduced me to called, and that changed everything for me because I found thousands of people offering their services to others who needed it, and if only I had known that this was available, I probably would’ve started there.

Now, I did have a little bit of money that was coming in from the business selling these ebooks and that was good. So I said, okay, I’m going to go on and see what exactly this is going to cost me. And the cool thing about Elance – which later combined with Odesk to become what is now known as – the cool thing about that website is you put in a job and you have people around the world who will bid, almost like an auction, to work with you. And they’ll tell you, “I’ll do that job for $200.” Here’s another person who’s going to do it for $150. Here’s another person that’ll do it for $400, but they’re more experienced and look at their portfolio, wow. By the end of two days after putting my job up for a voiceover to read this study guide, I saw 35 different people with price ranging from $200 to $5000. And I just got really confused. I had no idea what it was going to be like to choose from any of those.

Again, they all had decently sounding audio in their portfolios and again, different voices, different quality. It was just like okay, I have no idea where to go. So I got some good advice. Somebody had told me, “Do not go with the cheapest prices, because those are people who are likely not going to give you the best results. They’re just undercutting everybody. They’re probably going to hand you off to somebody who’s going to do it for much cheaper and that’s how they make money, so don’t do it that way.” I said, “Okay, I’m going to take away anybody who’s under the $400 to $500 range,” based on the averages that I was seeing. I was hoping to pay less than $1000, so I was looking more toward the bottom end of what I had leftover, but then I heard the other thing that somebody once told me, and that said, “Well, make sure you listen to the portfolios and actually try to reach out to people who have worked with them before because communication with these people are very important.”

So I did a couple things. Number one, I reached out to every single person who was left. I got rid of the super high end people, because they seemed to be people who are reading more professional books and things like that. I needed somebody sort of in the middle. But I reached out to every single person in a direct message on this platform. Again, back then it was called Elance, now it’s basically called Upwork, and again, all these people were voiceovers. I was gauging how quickly they responded. My friend said, “If people don’t respond to you in a day, get rid of them. Those people are likely going to be people who are probably not going to be responsive when you work with them and we don’t want to work with them.” So that got rid of about half of them, which was really exciting because now I had a pool of maybe 15 people left. And then I got to pick and choose. I got to pick and choose based on the voice type that I wanted. I wanted a female voice because it was a little bit easier to listen to for long periods of time, especially for studying, so that got rid of about half of them. And I was left with about eight.

Then I started to have communication and conversation with each, and there was a woman named Trish. Voiceovers by Trish. Dot com, I think. I remember she sent me a voice message with my name in it, and that had a lot to do with the reason why I chose her. Now, she wasn’t the least expensive, but she wasn’t the most expensive, either. She was at the $2400 range and I got to tell you, she was definitely the best one for the job, but it was a little bit higher than I was wanting to pay, almost twice, actually more than twice as much. And I remember specifically going, “Wow, this is three months worth of rent for something that I could do myself. Maybe if I just get a better microphone. Maybe if I just practice a little bit more.”

I kept making these excuses as far as why I should continue to hire nobody and do this work on my own. But then I remembered my friends, number one, laughing at me. Not really, that’s not what I was remembering, although I do remember that. But again, all in good fun. But I do remember and I was thinking about what they would say and how much my time was worth. And that’s what really did it for me, to consider that I could get, quite confidently because of the portfolio and the communication I had with Trish, a really, really decent set of audio files that I could sell and the fact that I was probably going to get this done, she told me in about a week and a half, based on the workload, and that I could work on other things in the meantime and it would just all be delivered one day to me. I was like, “Okay, I’m going to pull the trigger and I’m going to do it.”

It was definitely an investment. $2400, again, for something that I could do, or I thought I could do on my own. And something that I was comparing in my head, just something of a similar price range. Three months worth of rent – yhat’s one quarter of the entire year. But here I was being a big boy, investing in my own business. A week and a half came by. I got the audio files from her. They sounded amazing. I put them on my website. I uploaded them all to the tools that I was using to deliver all these files and such. You can use tools that are similar today that are much better, like SamCart, honestly, for digital things. if you want to check that out. Easy to create sales pages. Easy to deliver files, etc. SamCart is what it’s called. There’s many other tools out there, but I’m an advisor to SamCart. That is an affiliate link, by the way, Little plug in there for my guys at SamCart. Brian, Scott: love you guys. [Full Disclosure: I’m a compensated advisor and an affiliate for SamCart.]

Anyway, I put it on the website. First day goes by, I make some sales. I make some individual sales. Some people bought the audiobook alone for $29.99. By ebook was also $29.99. But a majority of the people purchased the bundle for $44.99. A major savings when you really consider it. That’s what? $60 total. Now it’s $45. So $15 savings if you purchase both of them. And most people, like 80 percent of people from that day forward bought the bundle. Your best customers are your existing customers. I had a small email list of buyers that I sent an email to and gave them all a discount to it as well, so that added to the sales too. Within that first day, within that first day, because I had an email list, because I had this bundle, I made up the cost in one day. In one single day. And every day after in perpetuity. Even to this day. Actually, no, not until this day because I don’t sell that product anymore. I sell another company’s product as an affiliate because I’m no longer in that industry, I no longer keep up with what is new, and I essentially just have affiliate marketing on now.

Anyway, that’s not the point of the story. Passive income for the win though, for sure. But also investing in your own business for the win. Trusting somebody else. Doing a little bit of research upfront, like I was talking about, to find the right people to do the job. This was not a hire for long term. This was just a project hire. But it was an amazing way to start the process and to open my eyes up to this world of working with other people. Since then, of course, if you’ve listened to the previous episode with Jess in episode 473, I highly recommend checking that out as we talk about appreciation for those who work with you and the importance of that and how to show appreciation and whatnot. Definitely check that out. Jess has been on the show before. In fact, she was one of my first hires internally when I hired her for a non contractual hire, and this was Jess who came on board in episode 115, if you want to listen to episode 115, back in the day where I hired her mainly for email marketing. Or, excuse me, not even email marketing. It was just email management and I was drowning in nearly 10,000 unread emails.

She’s then since grown to so many more important roles in the business and is definitely my right hand gal for a lot of things in the business at Flynndustries and I can’t thank her enough for all the great work that she does. But I wouldn’t have been open to that if I didn’t, again, have that experience on a small level, on a project level. And yes, you don’t have to spend $2400 to see what it’s like to have other people help you. I mean, this was a big job, voiceover, 80 different lessons, etc. It was a big job, for sure. But definitely well worth it, definitely well worth it. When you find the right people and you really start to understand the value that your time is, it starts to make sense. So start small, pick those projects that you probably shouldn’t be doing that you know can help move the needle. And again, I was grateful that this project that I helped hire Trish for, Voiceovers by Trish, she gave me something back that was some intellectual property that I could continue to sell, and I sold it for years.

In fact, that product, again remember, $2400 to create, probably ended up generating over $150,000. In the world of investment, that’s a pretty good return. All this to say it’s great to relive those first moments and hopefully this has inspired you to get out of that comfort zone a little bit and to yes, invest in your business, which is – guess what? – also investing in yourself, and when you hire people and you work with them, make them feel special, too. Make sure to listen to the previous episode with Jess, episode 473. This is episode 474. Appreciate you coming up and listening on our followup Fridays. All the valuable feedback about these followup episodes on Fridays have been really great. And again, it allows me to just be here with you one on one and I can tell you these stories that normally wouldn’t come out because I don’t want to interrupt the interviews, but they do come to mind. I do take notes during the interviews and I go, “You know what? What would be a fun thing to talk about on Friday for people?” So we can go deep, and we can tell some stories, and we can relate to each other and hopefully I can help you pave some success in your journey, too.

Thank you so much. I appreciate you. Looking forward to seeing you next Wednesday in our next interview and episode. It’s a good one, I promise. It’s with one of my mentors and it’s going to be one that you don’t want to miss. Hit subscribe if you haven’t already. Thank you so much in advance for all the amazing reviews. Take care. And as always, Team Flynn for the win. Peace out.

Thanks for listening to the Smart Passive Income Podcast at I’m your host, Pat Flynn. Sound design and editing by Paul Grigoras. Our senior producer is Sara Jane Hess, our series producer is David Grabowski, and our executive producer is Matt Gartland. The Smart Passive Income Podcast is a production of SPI Media. We’ll catch you in the next session.

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