The “Do What You Love” Show: Episode 2 – Dan & Ian Put The Freedom in “Freedom Business”


After a larger break than anticipated, I’m excited to bring you Episode 2 of the “Do What You Love” show (formerly the Do Shit You Love show).

[If you can’t see the video click here to visit the page directly]

Episode 2 features Dan and Ian, the masterminds behind the Lifestyle Business Podcast and the Tropical MBA program.  In addition to their web projects, Dan and Ian run a tangible, product-based business from their headquarters in San Diego and satellite offices scattered all over Southeast Asia.  We filmed this episode while spending a weekend together on the beaches of Ko Phi Phi, Thailand.

Episode 2 Content Guide:

  • [1:18] – Content covered in the Lifestyle Business Podcast.
  • [3:05] – The details on Dan and Ian’s primary business (and their model).
  • [4:15] – How they got started and their influences.
  • [5:00] – How much work does it actually take?
  • [6:00] – Dan and Ian’s advice for “getting started with a product-based business”
  • [7:20] – Their #1 business tip for testing markets.
  • [8:45] – Difference in Dan and Ian’s traveling preferences for productivity.
  • [11:00] – “Freedom” is about much more than just travel.
  • [11:48] – Why Dan loves setting up offices in Southeast Asia.
  • [13:10] – Background behind the Tropical MBA.
  • [16:10] – Where do they see their business in 5 years?
  • [18:50] – Ian’s question for the Militia.
  • [19:35] – Dan’s question for the Militia.

Ian and Dan’s questions for you!

Ian:  What’s the “next step” in your progression towards you own definition of freedom?

Dan:  What do you love most about Man Vs. Debt?  Why do you come back to read?

Let Dan & Ian know your answers below!

(No, Dan is not on my payroll… I can’t afford him right now)  😉

27 thoughts on “The “Do What You Love” Show: Episode 2 – Dan & Ian Put The Freedom in “Freedom Business””

  1. Great interview everyone! If I had stayed to watch it, I would have seen the battery die on the camera and warn you about it, pity! 😀
    To answer the two questions asked by Dan&Ian:

    1. The next step to freedom is letting go of the ideas of steps and freedom altogether and embracing how I’m free in what I have right now 🙂 The same can be applied to so many people if they just looked at their lives slightly differently.

    2. This site’s posts are extremely detailed; either thorough interviews like in this new series or amazingly well researched posts. The site’s merits are uncountable and the reason that it’s clearly so popular.
    However, these days I come here because I met you personally and now consider you a friend! I’m sure readers who have commented and been in touch with you frequently would feel they’d know you too.
    Hope the two girls are doing well!!

    1. Thanks, Benny!

      I like your comments on freedom. Although, I bet there is a more tangible next step even if you are letting go! 🙂

      I’m having fun loading and breaking down your interview as well. Not sure how I’m going to share all, but it’s a blast! 🙂

      1. Good point Baker – staying stagnant and being happy about it is also not quite a good solution! A balance of improvement and acceptance would be ideal 😉
        Glad you’re having fun with the video! Looking forward to seeing what you’ll have done with it 🙂 Wait until the Internet gets hit by 1GB+ of Bennyness!!! 😛

  2. I love the back ground noise and the setting as I sit here in Chicago surrounded by snow and cold. Ok you have found the life style. Best of luck and enjoy the journey. Looking forward to your next post. I also love the practical advise from Dan and Ian

  3. Hi guys,

    I’d love to ‘bite’ on these questions – great idea, and thanks for the chance to share my thoughts.

    1. Next step. I have always had some kind of ability to help people figure out what they should be doing with their lives – their Calling, and to inspire them to pursue the dreams they’ve left on the back-burner of life. I’ve made this my full time business with live workshops, and eCourses, which is great BUT… MY NEXT STEP, in order to achieve what I want for me and my wife and kids, and the travel and adventures we are salivating for: I consistently make about $28k a year with my business – no matter what I do. I have rutted in at that point, and somehow my next step is to break through that. I don’t know hot to do that yet, but somehow just saying it out loud to you guys feels right.

    2. I come back to read this blog because of the inspiration I get from Baker living his travel dreams with his young family. He’s at a similar spot in his life to me, and he’s been able to take his family dreams and make them happen, and I want to too 🙂

    Thanks for listening,
    Alex Baisley

    1. Alex, I loved how you know that know what you do (without reason I assume) you’ve developed the skills to have that base income, even if smaller than hoped, working in your passion.

      The ‘break through’ point is bound to come if you continue to work at it. And when it does, it’ll be awesome! (I assume, working on that myself)

  4. First off, thanks to all of you for taking the time to share our conversation. Oh man did you guys make me long for the open road again! My husband and I just returned to the US from a 2-year journey by expedition vehicle (spending most of our time in South America) and we are having a bit of trouble “fitting in” here now. Yes, it’s easy to slip right back into old routines and habits, but we now employee a very different mindset from most Americans (some might say we were “not normal” before!) and are having a tough time finding our “tribe” here. We don’t watch TV (with the exception of the Olympics right now and a few cooking shows while I work out) and we often find it difficult to find common areas of interest or topics of conversation that we are interested in pursuing with folks here. Yes, we have some very intelligent and fun friends and family members, but there seems to be very little focus, or even interest, in meaningful, change the world, types of conversations. And no, we don’t consider who’s winning on the Amazing Race world changing (although it is cool that Americans are getting exposed to other countries and cultures). I hope this does not sound arrogant – it is simply our reality after spending so much time away from the media- and celebrity-focused U.S.

    In answer to your questions:
    Ian: What’s the “next step” in your progression towards your own definition of freedom?

    We already consider ourselves free. After all, we have done what many other simply dream about – we checked out of normal life, shed our possessions and traveled the world (43 countries at last count). But, we are again faced with wanting to build our “nest egg,” so we are exploring opportunities. Finding those, from a list of pursuits we feel we can feel passionate about, will provide us with the ultimate freedom. Freedom, for us, is not doing nothing. Been there and done that! Freedom for us is growing, learning, exploring and adding value, leaving the world better than we found it, in whatever way we choose to do so at the time.

    Dan: What do you love most about Man Vs. Debt? Why do you come back to read?

    I love that there are Americans who are saying “ENOUGH ALREADY!” Enough to debt, to materialism, to the status quo. To be honest, I thought we were the only ones who felt that way! Rock on Militia Members – we are a tribe to be reckoned with!

    I wish you three, and all your readers, my fellow “tribespeople,” much success (however you define it) and happiness in 2010.

    Steph H.

  5. Nice interview.

    One tip – Let them talk more. Have your questions ready, ask them, then let them talk.

    You don’t need to validate them with “yeah.. yeah”, or to finish their answers for them.
    Sometimes they were about to keep talking, but then you cut them off.

    Keep it up.

    1. Thanks, David. I’ll work on that! Watching the interviews back again is a great exercise for me to realize when I fill in gaps to much. I don’t want it to be super-scripted, but I also don’t want to talk in circles!

      Appreciate it!

    2. David, my thoughts exactly as I watched the interview. Ask and then sit back and let them answer.

      I just stumbled onto the site here and am liking it thus far. Keep going.

  6. Great video, guys! We’ve been working on our round-the-world trip for a while, so our next steps are pretty well laid out. My cat is moving to my mom’s house next week, and the house goes on the market the week after that. We’ve already saved quite a bit of money and decluttered and will continue on that path until we leave on October 1. It is really amazing how just putting one step in front of the other takes you from a margarita-induced idea to travel the world to actually doing it.

    The reason I come back again and again to MvD is that Baker does such a good job of sharing information, both his own and from others. His enthusiasm is also contagious. The community is like-minded, and I love hanging out in a place where people understand the richness that comes from living within your means.

    1. Betsy, I’m super excited to hear more about your “launch” day as it approaches.

      You guys have awesome drive and dedication. It’s inspiring. Thanks for the kind words!

  7. To answer the questions from the video:

    1) My next step is to take the plunge. Quit my job. I get paid very well to do a job where I honestly don’t have to work a lot and rarely am stressed. I get to work from home quite often and my boss is the best. But I’m still in a cubicle (most of the time) doing something that I don’t enjoy. Quitting my job is a huge risk for me – and it’s tempting to wait until the “perfect moment”. But I’m afraid that if I keep waiting, the perfect moment will never come.

    2) I come to Man vs Debt because it is inspiring. I would consider myself on the edge of breaking through the 9 to 5… but I’m not there yet. So it’s very motivating to hear other people’s stories of how they did it. It is so great to see people doing what I want to do… traveling, working for themselves, enjoying every moment of life. I know I can get there – because others have done it!

  8. Baker, wow that video looks clean. What a pleasant surprise to see this video posted here! It’s great to see everyone’s comments. My next step is to build an office here in Manila that can help to grow our business and give people great jobs. The challenge I’m facing is that I don’t want to build myself a job, so I’ll be focused on getting great people who can manage themselves in a flexible environment. One thing I really love about your blog is the design, I know that’s a little superficial but I don’t read stuff through a reader so its a nice experience to stop by your neck of the woods. I also think your essential reading block is really smart. On my first visit I read half of the articles and got hooked. Now I’m looking forward to future video interviews, looking forward to getting that phone call!

  9. Baker, Great post as usual. I love hearing from people who are actually living the dream. I hope you can do more of these interviews in the future.

    The next tangible step for me is completing the inventory of all of my “stuff” I started a few weeks ago and barely finished one room. It’s amazing how much junk you can collect!

    I started reading PF/Lifestyle design blogs last month and MVD is by far my favorite. At first I liked that your posts were very “scannable”. (now i read every word) Your writing style is very personal and genuine. You seem to really connect with your readers. All that said, the one thing that made me come back was Tyler Durden’s Guide to Personal Finance.

  10. Adam,

    I agree with David’s advice above and was thinking the same thing throughout both of your shows so far. To implement: ask a very open-ended question (without elaboration or clarification), wait a few seconds, and let them run with it until they are done.

    First, the people you are interviewing will most likely have an agenda of what they want to talk about, so by giving them a very open-ended question, you allow them to respond in whatever context they see fit. After that, then you can ask more specific questions to hone in a particular item of interest, etc.

    Second, as a teacher I know how awkward “wait time” feels, but it is essential. Don’t feel like you have to fill up any silence gaps for your interviewees or your audience. Both groups need that time to process your question and, in the case of the interviewees, to formulate their answers.

    Having said all this, your enthusiasm is absolutely contagious and your eagerness really shows through! This constructive criticism is definitely coming from a place of love so please don’t be offended!!!

    My first “next step”: Get out of my teaching job! I just can’t take it anymore :p I’m sure you’ve heard some horror stories from your wife, so maybe you feel me on this one. I wanted to leave two years ago, but I got pregnant and my husband and I finally faced up to our financial reality. We saw there was no way I could risk it with a baby on the way and almost 90k of non-mortgage debt. We’ve spent the last two years on mission to be CC debt free and only have 2k left! Now we can actually afford for me to leave teaching live on one salary if we need to.

    Why do I read? You have been an inspiration in all of this! When we hit our financial realization (I had just found out I was pregnant in Jan 2008), I scoured the web on a mission to learn as much as possible about debt reduction and found your site. Your story is absolutely intriguing. Having a small child of my own and a mountain of debt, nearly all behind me, I identify strongly with your story and marvel at your ability to make the bold moves you did. You continue to inspire and I am cheering for you that your mission and passion play out just as you want it to!

    Keep on keeping on!

    *sorry for the long post*

  11. Great interview. I like the fact that they say “We work really hard” so many guru’s preach rich quick with no work involved. Lika I always say ‘Do what you love and do it well and you will always succeed” Hopefully we will set up our no cost summit and I will see you in the Philippines soon Dan.

  12. Love the interview- I cried a bit out of envy as I sit here looking out my window at the wind whipping across two feet of snow in my front yard! My next step maybe to move to a warmer climate!
    I’m at a fork in the road and debating my next step: build my emergency fund FAST with my current job OR find a job more fulfilling job at the risk of slowing down my contribution to the emergency fund.

  13. This was an awesome interview man. I hope I can be out there soon giving some interviews too. Every morning I wake up just for this goal. I want to live this amazing live you guys are living. I am starting to believe in myself and finally working the 100 hour workweek to be there soon. Thanks guys really great questions to ask too.

  14. Baker,

    I like your idea for this show and these guys are definitely interesting, but I have no idea what they do outside of doing a business that go with there lifestyle. I watched the entire thing and still haven’t a clue exactly what the sell, why there hire people in south Asia, I mean, I don’t know anything!!! I wanted to know and was eagerly waiting!! It was kind of like have sex and not getting to finish, you know what I mean Baker?

    I think you’re talking to much and not asking the right question to let the guests present their material, or letting the audience in on the who, what, when, how , and where of what is going on. To be a good interviewer you need to ask concise questions, so that viewers like myself get the info we want to hear or the happy ending!!!

    You seem like a chill guy with good intentions, but get over yourself,f and give us some meat bro!!! We will all want to come back to get info.

    Thanks and keep up the good work!

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