TMBA 251: The Entrepreneurial Quest

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This week, we’re talking about the four elements of the “Hero’s Quest” that every entrepreneur embarks on. This episode is all about looking back and understanding the first six months of taking off on a new project or a new business, the struggle that it is, and how valuable that can end up being on the narrative of your life. We also answer some listener questions, including one about cold calling a huge corporation to make a sale.

Listen to this week’s show and learn:

  • The pros and cons of a software business versus a product business as a first entrepreneurial venture.
  • How to find the turning point in your quest and capitalize on it.
  • What you can do to develop your own opportunities that don’t need to be within existing scripts.
  • Why you need to forget about the real world sometimes and build yourself a new one.
  • How to identify and overcome the obstacles on your path to success.

People on this episode:

Mentioned in the episode:

“Friday Afternoon Sunset”

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Dan & Ian

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Published on 07.03.14
  • HUGE TAKEAWAY: your runaway, by default, MUST be on the salt flats. Doing it on a cliff is just a form of resistance/entrepreneurial masturbation. I know this because I tried putting my runway on the cliffs.

    My quest: I was technically homeless for 4+ months in Boston while teaching myself SEO. My morning showers were all at the gym, my meals were all leftovers from various catering events, and my bed was the floor of a conference room. I got to practice my Spanish with the evening janitors and became reallly good friends with the neighborhood baristas. Would I do it again? F**K NO! I was horribly underslept/overworked and, though I learned a skillet, I never made super scary decisions because I could see the water crashing on the rocks below. But hey, it makes for a cool story.

    That was about 20 months ago. This episode is a sign — it’s time for another quest! (see you at DCBKK)

  • Some people need a cliff to motivate them. For me the takeaway is that you can control the runway. Choose one that’s right for you. For me, it’s gotta be salt flats. For others, cliff.

  • Love the “corner office” analogy. Shared this episode with my friend who was the “only smart person” in my office:) Before he quit.

  • Rob

    It’s one thing I wish they taught me in school. They should have taken field trips to offices around town and specifically asked kids “do you want to end up like this guy? he has a corner office, but just look at him…”

  • This is a great episode because it can also help people who are in the beginning of their journeys take a hard look at themselves and see if they’re truly on the road/runway or if they’re just playing around.

    Maybe I’m the odd one out, but I don’t look back on my first six months especially fondly. The good part was the initial surge of enthusiasm that resulted in my producing a phenomenal amount of work – but I was constantly plagued with insecurity as to whether it’d ever go anywhere or pay off. Yet something – some core conviction or certainty very deep down – kept me going.

    If I were to repeat the process and start a new business, I think those early months would be easier because now I have a better idea of what traction looks like, which activities are essential and which are not worth my time, etc. I wouldn’t be navigating through completely uncharted waters.

  • Really dug this episode…have been taking things for granted lately and the was a good reminder of the superhuman feats and torturous months many many years ago that it took to get the biz where it is today, resonated with a lot in this one

  • Ricardo P Aquino

    Thank you guys for another awesome episode! Made me take a hard look at myself, my goals, and aspirations.

  • Thanks bros, nice cast. Don’t agree with the part about giving up surfing but appreciate the intended lesson that there are things that we need to give up in order to succeed. I’d challenge that a bit and suggest that crafting a life worth living also feeds those passions that move deeply within our souls—trading that for mo $ or more “success’ isn’t always the right decision.

  • Ian

    Derek, agreed that giving up your passions for money isn’t necessarily the right decision. I’m back at some of the hobbies I had to give up in the beginning. And truth is I have more time and $$ to enjoy them now vs. then. But the story we were trying to tell there is sometimes you have to give them up at least in the short term to focus your energy and intentions on the longer term. Some people do just fine not giving them up at all – highly situational I’d say.

  • Ian

    Thanks Brendan, good to hear we can still stroke the mind of an OG.

  • Joshua Ebner

    Very cool that you guys are addressing the entrepreneur-as-hero narrative.

    Culturally, it seems obvious that people are searching for something better. Many seem dissatisfied with lives that lack meaning, and also lack personal success that they hoped for in the form of great relationships, control of one’s time, freedom to explore, etc.

    Meanwhile, something new seems to be emerging: an admixture of modern technology and values that are a half-step from classical ones. We have new tools that empower individuals, and also an interest in things like “creating massive value,” and “changing the world.”

    I’m not sure what will become of this mix, but it’s awesome that you guys are subtly addressing it, and giving people some tools to move towards whatever this modern heroism might become.

  • Hey Dan,

    Great episode!

    There were two turning points for me:

    1) Reading the Four Hour Work Week and realizing that a life of travel, adventure and freedom was even possible.

    2) Meeting you and working for you. You helped me realize that
    * building a location independent income stream was not THAT hard.
    * it’s possible to run ‘legitimate’ businesses while on the road, not just niche sites.


  • JanBuss

    Fantastic episode guys, thanks a ton. I have a few thoughts on SaaS versus physical products, being a software guy myself. First of, software is both harder and easier than products at the same time, in the sense that the software world is very forgiving, when it comes to failed businesses and products, you can always, always leverage what you created into new opportunities and starting a software business as a developer will in most cases not set you back. With products on the other hand you might end up with a sunk sum of money and a storage full of junk and nothing to show for it.
    No one applauds the guy (except for us fellow souls in the trenches) who designed a new type sippy cup noone wants, on the other the CTO of a failed social dreck sharing site walks away with having demostrated a valuable skill.

    But therein also lies the way in which software is harder, you can from daily use gauge fairly well whether a physical product meets a need or is desirable in some way, with abstract information systems on the other hand you havent got the faintest idea, the experience of a need is not as immediate, there are too many variables to consider in oder to determine its usefulness etc.

    For this reason customer development (a la lean startup) is flawed and highly unreliable at best, explain to me in the abstract the problem you are solving for me and I might profess to love it, but still end up having no use for the software endproduct.

    Ideally a software developer looking into starting a SaaS company partners with someone in the industry they are targeting,and additional benefit is that if you have an idea and you can find someone within the industry so convinced that yours is a good one to partner with you, you might really be on to something.



  • Just stumbled across your podcast and loved this episode! I’ll definitely be back for more. I’m just getting started out and am finding it is the mindset obstacles that are the hardest part of “building your own world”. Great tips on how to work through that.

  • yo ! thanks Nate appreciate that

  • haha :D

  • hey Joe thank you so much for that! Wish you the best in your journey.

  • I agree with the general frame up here– I was listening to Peter Keller on Mixergy recently and he said the motivation walking past his inventory in his garage gave him. He needed to sell that stock! Whereas with software you might not have that risk but you can keep moving the target. That said, many dev/founders don’t properly cost their *time* input, whereas almost all manufacturing startups outsource production so can be at some risk advantage there– at least they aren’t spending their time on the wrong things, one might say (or have some insurance there)

  • hey David love the kind words. You defo don’t need to be Bill Gates to make it happen, you just need to keep pluggin’ away! :D

  • yeah it’s interesting to see this culture of “purpose cultivation” and experience gathering emerge. just riding the waves !!!

  • I agree with that ! I think for me Golf wasn’t going to be that passion and I was willing to drop the time expensive hobby that I might not have even considered before I started a business. I retained things like reading that might be more like surfing for others.

  • thanks Ricardo!

  • yeah totally!

  • I think I was plagued by the same sorts of misgivings but I think that’s part of the reason I look back and lionize that time– i overcame those things.. maybe you are waiting for more hindsight? or maybe you aren’t as much of a masochist as me! :D

  • Yeah this is interesting guys, could easily go both ways. Many people seem to mix them. Like a cliff but a parachute, I’m thinking again of Peter Keller’s interview on mixergy where he put his back up against the wall with his inventory purchasing but kept his day job for a year as a parachute.

  • JanBuss

    Very good point, thanks for your reply. I definitely agree with the time valuing part, that is an issue that relates to contract work and overtime aswell and especially with people who blur the lines between hobby and work.
    On the other hand a friend of mine started producing his own handbags a few years ago, and he was working constantly as well, travelling, taking calls at night and being a general nervous wreck :) but at least you have the excitement of that physical thing in the end that you made come into existence.

  • ah the nervous wreck part rings a bell! :D

  • Hey buddy just catching up on my reading and saw your cover pic…the entrance to the W Hotel in Seminyak. I was just there 3-weeks ago. Sorry I missed you my man. Back in the States now. Checkout the sunset pic on the beach at the W.

  • Niiiiice!!! Yeah I was following your journey on your blog, think I just missed ya. Hope you had a blast! Thanks for the pic, fantastic!

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