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Getting Ahead

On this episode of the Because Money Podcast, we are joined by Tom Drake, white collar by day, finance blogger by night. Chances are if you have spent anytime on the internet reading personal finance blogs, you have come across something penned by Tom. In our discussion, Tom shares his “secrets” << although not that crazy, about how he manages his small empire on the web while staying focused on what actually matters to him.

Here is a list of resources we thought you would like to see, enjoy!


Jackson: Jackson Middleton

Kyle: Kyle Prevost

Sandi: Sandi Martin

Tom: Tom Drake

Jackson: Good day, everybody. Welcome to the Because Money Podcast.  I’m Jackson Middleton, one of your hosts, joined with Sandi Martin, who is in black and white right now. We’ve got Kyle Prevost, as well.

And we’ve got our special guest, Tom Drake, today. You can’t throw a rock on the internet and not find a website that Tom doesn’t own. This guy owns almost every finance blog in Canada, or has had some part of it. But anyways, I’ll let Kyle tell you more about Tom and what he does and how he makes money, and we’re going to have a lot of fun today.

Kyle: Tom’s given me—Justin and I, my partner—a lot of help as we started, so I affectionately or sarcastically, depending on how you look at it, call him “The Godfather of Canadian personal finance”.  I think Tom started this whole online empire thing before I could legally buy a beer. So he’s been doing it for a while. He’s now growing his sprawling multinational conglomerate to include a lot of the leading personal finance blogs in Canada and a couple in the USA.

And perhaps what I find most impressive about Tom Drake’s rise to the top is that he’s managed to do this on the side. He’s got a full-time job and it’s not one of these full-time jobs where he gets to go there and not do a full-time job. It’s like a real full-time job. And he’s also raised a young family as he’s been doing this. So thanks for coming on, Tom.

Tom: Thanks for having me.

Kyle: So I think what every married person out there wants to ask is what sort of conversations did you have with your significant other when you started this online thing, and were you, like, “Yeah, I’m going to be putting in several hours, many nights, several nights a week, and it will all work out.” And it has worked out. But sort of how did those conversations go, Tom?

Tom: That’s a good question. First of all, I didn’t have that conversation. I just decided I was going to start a blog, and so I started it up in early 2009, and I don’t think anything would come of it. I figured at best it’s a tax deduction. [laughs] And it was just something fun I wanted to do, so I waited about a week or two and then I told my wife—or girlfriend, at the time— “Look, I’ve got this new site. What do you think?” And at first she’s like “Well, what’s the purpose?” [laughs] because she didn’t get the idea of a blog, really, let alone one on personal finance.

Kyle: I thought chicks dig personal finance bloggers.

Tom: No, it’s not true. [laughs]

Jackson: It’s not my reality. No, not there for me either, so we’re all on the same page.

Tom: So yeah, it just kind of evolved from there. It really was more hobby than business, though I knew enough to run it as a business that would at least be tax deductible.

Kyle: Cool. We’ve had some conversations back and forth. Sorry, I just had this weird flashback. I watch a lot of football right now, and the guys that talkover are always like, “We were talking this week about talking about if the quarterback you talked about”, and it’s just replaying in my head. But you and I have chatted, talked about the relationship you and your wife have in terms of splitting up work and just work/life balance as sort of the family unit, as opposed to like as individuals, and it works for you guys. So what’s sort of the secret sauce in the Drake household?

Tom: First of all, basically I consider it two full-time jobs. I’ve got my day job as a financial analyst and then in the evening after the kids go to bed, I do the whole blog thing. Liking both of my jobs makes it a lot easier. I really like the blog job more, but it certainly is easier to stay up for it. If you’re working 60 plus hours—I hate to actually calculate it—it could be up to 80 sometimes  in a week.

If you don’t have a certain passion for it, I don’t think dollars alone would make that work out. [laughs] I don’t think I could do two full-time real jobs and make it happen. It just wouldn’t be there. And then my wife, at first she was working, but once we had our first kid, after the parental leave, she decided that we didn’t need her to go back. Obviously that’s a full-time job in itself too, with two kids. When we were looking at it, it was just was a case of the child care, especially once we had the second kid. Given her salary, it wasn’t going to pay a whole lot anyways, so it’s not like it was a huge sacrifice in a way. It just seemed a lot more effective for me to put more effort in on my end and go with what was working, than to have her almost start from scratch a bit, back in her job. It’s just how it worked out.

She’s an aesthetician by trade, so she’s been doing a bit of make-up jobs and eyebrows and all that sort of stuff, so she’s starting to get the entrepreneurial bug as well.

Kyle: Oh, that could be dangerous. Two entrepreneurs in the same house. [laughs] I don’t know if there’s enough oxygen for all that.

So obviously you you’re right up-front with saying I don’t sacrifice time with my kids. I come home, we have dinner together, I have my family time. You’ve got a great quote that you use about your working hours, and when you do damage. I forget the exact words, so I’ll let you throw your philosophy out there.

Tom: I wish I had it. It’s not my quote. It’s Gary Vaynerchuk, but I can paraphrase it a little bit. Basically it was related to people that basically say they can’t find time to do something else, and the quote was that 7 p.m. to 2 a.m. is plenty of time to do damage. [laughs] So there’s basically time for a full-time job in the evening, without getting in the way of family or anything like that. And that’s why I like the quote because it wasn’t 4 p.m. on, it was 7 p.m.   But literally, I get that window with my kids, and we have dinner, play games, toys, whatever, and I put them to bed with my wife, and then I go to it.

Sandi: Do you stay up till two o’clock in the morning?

Tom: Sometimes.

Sandi: Holy moly.

Tom: I’d say an average is 1 a.m. So, two o’clock, it does get a little tough. [laughs] I’ve told Kyle before though, I don’t think I’m at the point now where I’d say I was necessarily proud of how little I sleep. I think it’s almost become a hit to the productivity. If I had a goal, it seems like an impossible goal, but I’d like to get to bed at midnight. I think if I can get out of that sort of a downward spiral, it would be helpful where I’d probably end up being more productive and still accomplish the same amount.

Sandi: This might be totally tangential, but are you a morning person? Do you find that you have the energy to work during the nighttime?

Tom: I’m an evening guy. If I didn’t have a day job, I’d probably work till three in the morning and wake up at ten. Also, if I didn’t have kids, I guess.

Jackson: See that, right there. I’m going to stop you because I work from home. I do the online stuff, and I’ve actually started getting up between 4 a.m. and 5 a.m., so that I’ve got all those hours before my kids wake up. Because I was staying up till 2 a.m. to 3 a.m., but then my kids are going to wake me up at 7:00. I’m up at 7:00, regardless. There’s no sleeping in till 10:00, because they’re on you. [laughs] Yeah, I get up before them and I found that very successful.

Sandi: It’s fun to get up early in the morning. [laughs]

Tom: See, I don’t get up in the morning–well, I get up because I have to get up, because of the day job, and the kids. True, 7 o’clock, although lately it’s been 6 o’clock. The 7 o’clock is sort of a magic time where you’re guaranteed to have that kid alarm go off.

Sandi: I work from home too, and I remember talking to somebody three years ago now, when I was just starting the business, and would we have these weekly calls. It’s Jason Hull, who is in Texas and now with My Financial Answers, I think you probably know him. But he told me one time, “If you’re not getting up early or staying up late, then you’re doing this part-time.” Like, if you don’t have the time naturally during the day, you have to make it somewhere. And for three years now, I’ve been getting up at 5 o’clock every morning and it feels like the best time in the whole day. I can have a coffee that’s hot, by myself. Amazing. Everything else just comes with it. Like yeah, I also do work then, but the coffee’s hot and there aren’t really any kids yelling at me, which is quite refreshing. [laughs]

Tom: That’s the same way I feel in the evening. Certainly there’s times where you got sick or cranky kids and they wake up again,  at maybe ten o’clock in the evening. But my wife certainly covers that then. I’ll help get them to bed, so make sure I get that block of work time.

Sandi: So you were seeing that your goal is to get to bed at midnight. Is there something going to have to give for you to do that? Do you feel that coming, or has it come already?

Tom: What I’m doing to get around that a bit is just changing how my business looks. You guys mentioned all the sites I own, well one thing I’m trying to do is just kind of merge them up and just have a little less to work on. The same traffic, there’s no loss there. But it’s less maintenance, it’s less time spent. It is just also less space in my head, because it gets to be too much stuff that you’re constantly thinking about. So I’m trying to get a little bit minimalist in my business, as much as I can, and even in my life; productivity hacks and stuff has become my new obsession,  of trying to figure things out and streamline it where I can.

Sandi: What’s a lifestyle hack you’ve tried that has actually been working for you?

Tom: Things that keep me focussed have been great lately. I may pronounce this wrong, but Pomodoro Technique. It’s basically 15-minute intervals or 20? Twenty, I think. Maybe even 25. I don’t know if it’s always even rigid about the time, but certainly you got a moment of focus and then and then five minutes of a break. And then you go back in kind of thing. And just having a clock to work to like that, even if you made it up yourself and I’m just going to work solid for an hour. It just keeps you a little more laser-focused.

Another neat thing for productivity I did recently, and seems a little too new age for me, [laughs] but it actually seems to be working, is Brain.fm. It’s a neat site that they have sort of this sometimes odd music, but it’s basically a science-based thing of focusing on the music you. Obviously there’s no lyrics in the music. It does sound very new wave-ish. I just thought I’d give it a try and it’s amazing.

And also on the point of trying to get sleep, they also have sleep setting, which is a whole different set of strange music. [laughs]

Jackson: I just pulled that site open and that looks pretty awesome. Sleep, focus, relax. Have you checked out Chris Bailey at A Life of Productivity, in Ottawa?

Tom: I don’t think so, no.

Jackson: To feed your obsession, that’s kind of where I get some of my life productivity hacks. He just wrote a book called A Life of Productivity, and he did a year of productivity, where he’s dedicated an entire year to just learning how to be more productive, and then he wrote blogs about it. You should totally check that cat out.

Tom: Yes, someone actually mentioned this to me. I remember the site now, but I never actually checked it out. I just had a conference and someone said, “Oh, you’ve got to talk to this other Canadian and check out their site”. It totally slipped my mind.  So I’ll have to make sure I actually check it out this time.

Kyle: My new productivity hack is to listen to people with kids and their schedules, and what they have to do, and then not have kids. [laughs] It’s making me feel quite lazy. So I will get my butt in gear since I have no excuse.

Jackson: Kyle wins the Internet with that comment.

Tom: It would be a good time to lay as much groundwork as you can because I know you’re newly married, so it wouldn’t surprise me if kids are around the corner at some point.

Kyle: My dad hopes.

Tom: The more you can do now. If I had something I wish I could turn back the clock on, I wish I had a clue about this stuff. Part of the reason I got into personal finance to begin with was because we had a kid on the way. [laughs] So by then it was a little too late to really get into any really productive time then.

Kyle: Yeah, we were looking at have you reached a point yet where you feel something giving on one job or the other? And I know this sort of Devil and Angel on the shoulder interplay’s been going on for a while. But why haven’t you just like lived the dream, like these guys I see online, whether it’s The Four Hour Work Week or Pat Flynn, or all these guys who give speeches about “Just jump, just jump and it will all work out”. And they use all these buzzwords, and then they try to sell you their spreadsheet or whatever.

Why haven’t you just become one of these guys that sells the dream? Why are you still working at your big bad corporate job there?

Tom: There are certainly times I wanted just jump. I think lifestyle-wise, it would be nice to maybe be the one at home that can pick the kids up and stuff. And my wife could go back to work to add a little stability at the same time. And we’ll probably get to that point, but I know lately one of the reasons I still do it is because I can. [laughs] As long as I’m not feeling like I’m about to break, because I think I push on.

It’s also give some safety, obviously, but I know a lot of the entrepreneurial types you mentioned, yeah, they say go for it. But I am personal finance first, anything I can do to protect my worth kind of thing, I don’t see the point. If I ever got to the point that I was making so much more money on my business, then okay, maybe. But I make more on my business than I do on my day job, but it’s not reigning me in.

Kyle: Yeah, but I know. My students are on me all the time, because occasionally I will try to gain some street cred by showing them something I’ve written in the Globe & Mail or in a magazine—which never works for one thing. Half the class is like “Globe & Mail, what it that?” [laughs]

Tom: Kids don’t read that.

Kyle: Like give me a break. It’s not a list. I’m not clicking on that crap. But yeah, so occasionally I will try this, and then the ones that do pay attention are like, “Why are you teaching? Like, you’re writing.” It’s like, “Yeah, I wrote this for free”. [laughs] Or I got paid the same amount of a half day of teaching. And it’s hard. It’s harder than people think to maybe make that jump. And you talk about the entrepreneur versus the personal finance, and I always have that battle in my head too. The entrepreneur is like “Go, try all these things and throw yourself into it whole heartedly, and see what happens”, and “how can you ever call yourself an entrepreneur if you still have a job?” [laughs}

Yeah, Jackson’s raising his hand. That’s what he does. He’s the man. I’m still like, “Ah, I’ll dip my toe in, but I’m going to like hang onto the edge here with my benefits plan” and you know all these nice things about being a teacher. So it is, I think it’s a unique for each individual that sort of break down for their own—like you mentioned—kids and a family, and I think that alters the equation.

I don’t know Jackson, what was like the driving force for you?

Jackson: I just simply can’t work for anyone else. [laughs] I don’t like people telling me what to do. So I’ve always just done my own thing. But I think Tom nailed it when he said he’s personal finance first, and he’s going with what works for him. And that that makes a lot of sense. I found that when I finally accepted who I was and started doing things that I was comfortable doing. And I think you nailed it, Tom, when you said, “Because I can”. Because this is what I still can do.

I realized very quickly that I can’t work for other people. And it’s not a bad thing, it’s just I’m not wired that way. I will work for 16 hours, 6 days a week on my own, doing my own thing, and I’ll struggle for you to tell me what to do for 2 hours a week. Same money, I’ll choose to work for myself. I just know how I’m wired and I’ve kind of figured that out. So if you’re personal finance first, and that’s where you place your emphasis and your value, great. But for me, I put it on freedom, being able to do what I want, when I want, to be my own boss.

I’m hard-wired entrepreneur and I mean, so much so that we moved out to the island and we live as hippies on a commune on the side of a mountain with chickens. It’s crazy, but I’m loving life and I’m doing what I want to do, and nobody’s telling me what not to do. So I’m having fun and just doing it.

Kyle: You should write, like The 18 Hours-A-Day Work Week.

Jackson: Don’t get me wrong. I like cooking and I like doing other things better than working, [laughs] but I’ll do what I need to when it comes down to it.

Kyle: And Sandi, you sort of have a grey area blend, right? Because like sort of your side gig sort of blends in and gives credibility to like your full-time income, or how would you describe it?

Sandi: It is my full-time income. So I blog as an ancillary activity for my financial planning business. I’m not an entrepreneur at heart. Like I was never yearning to watch the bank account for when the next deposit was coming in or anything. I’m not a risk-taker, so the idea that I’m doing this now–five years ago I would have laughed at myself and thought it was an alternate universe.

But there yeah there I was, self-employed, doing this fee-for-service financial planning, and my husband was self-employed in construction, and it was insane. It was just too much. So now he’s self-employed as a house dad. [laughs]

Kyle: Nice. That is ideal.

Tom: Jackson mentioned freedom, but one thing I did find lately is with the business doing slightly better than the day job is that my stress level at work has gone down a lot.  I don’t have the freedom of additional help whenever I want, but where I used to get stressed out, now it’s not that I don’t care about my job, but it’s just a different feeling it. Like I can be in a room of people completely stressed, worried about whatever the latest crisis is at work, and it just doesn’t seem to affect me. I can be just fine.

Kyle: Yeah, it is interesting how each of us has sort of created our own unique approach to balancing this stuff. One thing I wanted to note, Tom, is did you anticipate this in 2009? You were if not the first, one of the first few personal finance blogs, and really probably one of the first blogs in almost any niche to actually makes money. Did you did you want to turn this into a side gig, or at what point did that evolution happen?

Tom: It’s a good question. I don’t know when I sort of noticed it was going to become something more, because it really was an evolution. It’s not like I had this huge spike of traffic or income. It was this slow build, and even some drops, and it would go back up. So it really just kind of happened. It’s like when you look at your kids and all of a sudden it’s like, “Oh, you’re a lot taller”.  [laughs] You don’t notice it as it happens.

Kyle: How old are you now? At what point were you like, “Man, I’m going to make a lot of money off this”? Was there like a motivational curve? Like you were super-motivated and then you did make a lot of money, or sort of the money came in and then you’re like, “Man, I want to just do this”?

Tom: Yeah, once it started becoming really consistent, and certainly bigger amounts, it does help the motivation. I don’t think I could have done it this long—it’s not terribly long—but for years without something coming back to me, for sure. You mentioned from your vantage point, on one of the first sites in Canada, but really there were quite a few before, but a lot of them have come and gone. And that’s probably due to lack of income. You just can’t keep doing it forever. So kind of by attrition, I’ve become one of the more established bloggers over time.

But I when I started, I was reading blogs. I read six different Canadian blogs, and only one of them still stands, really.

Kyle: That’s interesting. So there’s like you keep plugging away morale in there somewhere.

Jackson: No, you’re  definitely plodding. That’s totally it. You’re a plodder, and that’s the coolest thing out there. It’s funny because how I first found out about you as I sat around my house and thought, I’m going to buy some really cool finance blogs. And I started doing GoDaddy searches and you owned every site that I said, “I want to own that one”. I’ve been following you for a while, but you’ve been there, like right from the start and you keep going. So that’s totally cool.

Tom: That was another thing I was able to do to build too, is because I had the income at my day job money, money I made at the business didn’t necessarily–I wasn’t relying on it to pay the bills. I could reinvest it back into buying sites and all sorts of fancy software and stuff like that, but nowadays I’m getting better about trying to actually make sure there is some extra income for us, not just bring it all back into the business.

But for the first five years probably, I probably didn’t really pull any money out of the business.

Kyle: Tom and I are both UFC fans. I picture Tom cutting a UFC promo, like “Embraced the grind. It doesn’t just happen overnight. You’ve got to want it”, something all cliché and sportsy like that.

Tom: I was just going to say that makes me picture this one image—you’ve probably all seen it—where two people are digging a tunnel and one stops and the other is just like a fraction away, one more dig and they’d hit this pile of diamonds.  Because if you if you stop, you don’t really know.

Kyle: Before we say goodnight here, I wanted to ask all you family folks sort of, if you had any like tips off the top of your head for some of the people out there that are looking at doing something on the side? Maybe they’re into this personal finance thing now and they want more money to invest. Their day job is, you know, they’re working towards a promotion but it’s just not cutting it. They want to earn some money on the side. What are some tips to balance that out?

I know Tom talked a little bit about how he does it. How can you, aside from waking up at 5 a.m. or embracing hacks, is there one thing  that you were like, “Oh, this really actually works quite well, and my wife or husband is happy with it, and it allows me to do XYZ?”

Tom: For me, I think the biggest thing, when it when I hear people say they can’t do anything. Not necessarily if they have kids or not, but the idea that you can’t do anything, but these are the same people that say, “Oh I had a long day at work, so now I’m going to watch TV for five hours”. That drives me slightly crazy [laughs] that they don’t see the available time. And yeah, you don’t have to stay up till 2 a.m. You don’t have to wake up at 5 a.m., but even Iike three hours a day would be just an amazing amount of time that you could put into something. And some people just say, “Ah, I don’t have any time. I’m busy all day” and it’s just not true if you looked at what you were actually doing.

Jackson: Isn’t that the other Gary Vaynerchuk famous quote, “Stop watching ‘Lost'”?

Tom: Yes, yes  that actually is him.

Jackson: Yeah, stop watching and then a big old swearword lost.  And that’s one of his best lines.  It’s like, “Wow, you don’t have time? Stop watching @*% Lost”. [laughs] I remember the first time I heard it and I think I was actually watching Lost. I’m like, “I don’t have time for this.” For real, so it was yeah, a smackdown.

Tom: I’ve become so anti-TV in a way, that I will watch new shows. We have some shows. I need some time to spend with my wife, [laughs] so we will watch one show an evening. But people at work will say, “Oh, you’ve got to watch this new show”, and I’m like, “No, I’m kind of just waiting for my shows to get cancelled”. As another show gets cancelled, we leave it at that.

Sandi: And of course, I’m always going to say this, but if somebody is sitting at home saying, “I want to start a side business”, or “I need to make more money”, my first question is never, “Well how are you going to do it and what are the life hacks you’re going to put in place?” or “Why are you watching TV?” My question will always be “why are doing it in the first place?” Honestly, it seems like a wonderful idea  for somebody who’s never even thought about it: “I’m just going to go out and make an extra $1,000 a month”, but I would want to know the amount of time that you have to put in, the amount of your own personal energy, and then the amount of your own investment capital that you would need to actually do it. I would want to know why you feel like you need to warn that extra $1,000 in the first place before telling you how to start. I don’t mean to say that you should try to spend less and then you don’t have to worry about earning more as a question, not at all, but I would definitely ask why you feel like you need to do it, before telling you to go start.

Kyle: Yeah, compare it to why do you need it and maybe compare it to why not go work for someone else. If money is the only factor, like Tom said, probably even now with a fully developed company, if Tom put in all those hours working for someone else, he could probably come pretty close. What do you think Tom? Would you would you actually overshoot working for someone else in terms of income coming in? You were saying it’s more of a passion, or was at least at first, right?

Tom: Yeah, if you don’t have a passion for what you do, it would be possible. The dollars only take you so far. [laughs] It’s basically what Sandi said. If you don’t have a reason for doing something, then the money alone is not going to do it.

Jackson: Yeah, it’s funny because that was my point, when you were going to roll around to me, and you would say, “Jackson, what do you think?” I was going to say, you’ve got to do something you’re passionate about. If you’re not passionate about it, forget it. You will not follow through. So, if you can see yourself doing it consistently, without generating income, and the act of doing it itself is worthwhile and brings you joy in your life, great. Just be smart about it and figure out how to monetize it. But if it takes five years, great. But yeah, side businesses,  if you’re doing it just for the money, forget it, you’ll fail.

Kyle: So Tom, before we wish everyone a Merry Christmas here, why don’t you tell us and we’ll give you like about seven and a half minutes here, so you can go down the entire list of where we could find Tom Drake.

Tom: Canadian Finance Blogs, obviously, the site I’m most known for. It is the one I started with. But I’ve certainly spread out. createhype.com is sort of where I cover some marketing stuff, plus it’s been kind of an exciting thing for me as I build the business. And there’s a slew of sites in the states that I have not merged to anything yet, [laughs] so I’m trying to figure those out. But persondividends, stupidcents, even financialhighways, mostly American-angled. The Mastermind Show, I’m on there with Kyle, so I have to give that one a shout-out. There’s probably a few more.

Kyle: So if you type in “money” and “Canada”, Tom will be six of the top nine results.

Tom: I haven’t tried that. [laughs]

Jackson: Well yeah, the first 78 pages of Google—all Tom. [laughs]

Kyle: All right, guys, we’re going to take a little Christmas break. So this will be a final episode and we will see again January 12th. Until then, on behalf of Sandi and Jackson, Because Money would like to wish you a very Merry Christmas and Happy Holidays.

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