TMBA 427: Dan and Ian's Consulting Corner

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Dan and Ian love receiving emails from listeners of this show. They don’t always have time to respond :( but one recently caught their attention.

The message was from listener Jay Clouse.

Jay wrote that he was struggling with some of the common issues that early-stage entrepreneurs face. Jay recently left his position at a tech startup and has started a new business facilitating mastermind groups.

Rather than email him back, Dan and Ian decided it might be fun to call Jay and talk about some of his challenges ‘live’ on the show.

This episode might be useful for those who are just starting a business. For more experienced entrepreneurs, we hope you’ll stick around and maybe share some of your own advice for Jay, and people like him, in the comments section.


Listen to this week’s show and learn:

  • Why Jay decided to leave a product management role to pursue his own business. (3:25)
  • Some of the bigger problems that Jay is facing in his business today. (5:50)
  • Why you need to consider the needs of the market if you are trying to create a lifestyle business. (19:10)
  • The benefits of building an organization rather than raising your rates as a freelancer. (27:20)
  • Why being honest with yourself is the most important part of this process. (38:37)

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This week’s sponsor:

This week’s episode is brought to you by Empire Flippers. Empire Flippers are the leading specialists in helping entrepreneurs buy, sell, and invest in online businesses. Whether you are looking to buy or sell, Empire Flippers’ dedicated team will make sure you are supported at every step of the process. As a very special gift, the Empire Flippers are offering a free business valuation (A $300 value) exclusively to listeners of this show. All you have to do is visit for more details.

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST. Cheers, Dan & Ian

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Published on 02.08.18
  • Had a blast talking with you guys — thank you for all the insight. If anyone has any thoughts or input, I’m all ears!

  • ww

    What is the Taylor Pearson product where you can lock yourself into deadlines? I need to buy this! Mentioned at 30:30

  • PS: I offloaded my freelance work at the beginning of this month (February). Full steam ahead.

  • Thanks for asking!

    You can enroll here:

  • Loved it. Especially the idea of breaking things as soon as possible to test limits of what’s possible/probable.

    HATE Disqus still.

  • Seán Feehan

    Jay Man, you’ve overcome inertia and you’re riding the horse. Go for it and see if you can canter, try a jump and go for a gallop!

  • DT is one of those whiny old man customers you should ignore – they’ll happily use your product but will find something to whine about regardless

    +1000 for disqus, big fan

  • Great episode. Really like these kind of episodes where starting/smaller businesses are analysed and feedback is given.
    There’s always the question: Is this business a good opportunity for YOU (and not a good opportunity in general).

  • cheers Marc

  • Recently joined the podcast-listener community, stumbled upon this while looking for a good travel-themed series for those of us in the business or personal interest of travel. Thanks for being among the first series I’ve discovered that actually talks not just about concepts in sweeping, vague non-context, but in actually discussing gritty detail!

    What struck me as a listener in this episode, was perhaps something of a matter of perspectives and the black-hole from which bachelors sometimes cannot escape – a similar issue to those in the digital nomad community, I feel.

    The conversation quickly went to being ‘lean’ and I can’t help but wonder if there’s a personal life priority that needs to change and which might accelerate the guest’s problem solving:

    From the top, if he owns his car and has no debts, how is it that he can’t get below $2000? Ohio studio apartment, owns his car, has income… might be able to dress his income:spending issues down with a ‘lean’ lifestyle at home…

    Here’s where I think the use of time priority can be revisited and how it’s relevant to both staying ‘lean’ and encouraging growth in the business by finding the time or better balance of opportunity-cost of time, alongside some personal growth for that time in the future when there are other business supporters, eg a partner or more personal responsibilities; something to which the hosts alluded during the latter part of the session:

    Our guest quickly described how he was no good at cooking and could foresee cutting back on coffee meetings. This to me is an explosive, poisonous NO!

    No one ever met a client by cooking at home, sure. Equally, however, no one ever met a client by having a meal ordered on uber-eats.

    He’s currently retrieving roughly $50/hour in remuneration for his efforts from clients, based on his $100/month with ‘about an hour every two weeks’ of commitment. So his time is currently worth $50/hour (more or less). I could see the balance being in favour of dropping the coffee meetings when a meet is
    – 15 minutes of travel time in both directions
    – price of a coffee
    – 60 minutes of meeting time

    That’s 90 minutes and a coffee = 1.5 x $50 + coffee = $82 (Starbucks latte?)

    You’re going to save the time (and money) in ordering in or just microwaving a meal, sure…

    Cooking can suck. It can eat a bit of time when you’ve no clue what you’re doing, but eating out or even ordering in – well, two uber-eats charges = 1 x coffee at a local starbucks. You’re never EVER going to get a $1000 out of your uber-eats delivery driver as a client (or whatever other perceived time-saving service is being used).

    I’m not going to delve into the logistics of cooking, but my point sticks. Even at an opportunity cost savings or real cost savings, you need to be having coffee with real humans so you can grow your client list and find a way to escape that limited size email list. Meeting people, even random people, is a sure-fire way to grow your client list or even just your referrals.

    Maybe even change those coffee meetings to attendance at a monthly or even bi-monthly event?

    Second up, at some point we all escape the bachelor life, unless you’ve really set in for a Peter Pan session to end all sessions. At some point you will grow personally or even find that you have people growing close to you. Let them! They are your biggest supporters, a wealth of positivity, and a fountain of practical ideas you might never know.


    If you can’t reciprocate and simply make the excuse of being ‘bad at cooking’ – you’re already your own barrier to that success. Your body will thank you, your future partner will thank you, those clients you never would have met by skipping the coffee meetings – they won’t even know how they were one frozen pizza away from going to your competitor so they might not thank you!

  • cheers Shy welcome to the fold. Glad you dig the show. Appreciate your thoughts.

  • Hey Shy, thanks for the feedback! You’re right — my major cost drivers are 1.) rent 2.) car insurance 3.) health insurance 4.) gasoline and 5.) food/bev. With some changes (continuing to reduce alcohol consumption for example, or cooking a larger percentage of my meals at home) I could get under $2000. But it’s worth noting, though I’m in Ohio, the cost of living in Columbus is rising (especially in neighborhoods adjacent to mine).

    My coffee comment came with some missing context — I work out of a coworking space that has a public coffee shop in the bottom of the space. What I’ve been trying to do lately is push more meetings to *that* coffee shop where I can offer them a beverage, without needing to purchase one of my own. I certainly agree — cutting out meetings would be a big no no for my business which is based around people!

    Thanks for listening and for your insight.

  • My pleasure, thanks for your considerations and returning the insight!

    You’re right in that there’s always some balance to be played, reducing alcohol consumption was a HUGE bounty for me. There are other expenses that accumulate with the social aspect, too – how to get home, how to keep from eating delicious street foods at higher-than normal / necessary rate, opportunity cost of productivity, etc…

    Again, like the coffee meetings, a necessary component – I was in China for a number of years and the business culture pretty much wants to strike your liver and wallet haha

    You’re certainly on the right track, keep experimenting with what does and doesn’t work for you – have you considered a home office and reducing the number of days a week you spend at the co-share to maximise both savings and productivity on the days you are there? Check Ohio’s zoning and see what positive things this might do for your taxes.

  • What’s the newest news round Ohio, Jay? Did you get to try out or implement anything from the show???

  • hey @TravelShy:disqus, thanks for asking! I’m moving forward pretty quickly here. A few updates…

    1. I’ve revamped how Unreal Collective operates. I’ve raised my prices and added new product options:

    2. I launched a podcast of my own! It’s been getting a great reception so far. It’s called upside, and it’s about startups outside of silicon valley.

    3. I have a publishing agreement with Linkedin and their Learning (courses) platform. So on the side I’m creating some courses for them. Different than a Udemy — they contract all of their authors in publishing deals.

    It’s been fun times!

  • That’s great, glad to read your updated comment! Congratulations and well done in maintaining your momentum!

    Did you find anything particularly helpful from the TMBA segment or from any of the subsequent conversations?

    Outside of the obvious masterminding you must have done, what did you change to overcome the obstacles you were facing in your original query?

  • I think the most useful things were:

    1.) the nudge to say, “you know what you’re doing, just rip the band-aid off and move forward” and

    2.) “increase the velocity of exhausting your options”

    I don’t know that I did anything to overcome the initial obstacles other than get myself to start knocking over what I think of as “the first domino.” I have gotten better and better at forcing myself to make the first move that naturally sets a chain effect in motion. Dropping a freelance client was the first domino to needing to ramp up my velocity. Telling *a lot* of people I’m launching a podcast was the first domino to publishing it, etc.

  • Guessing you’re an efficient man, someone who really likes lists perhaps? haha

    It’s great to hear (*read) a success story based on something actionable from the content, even if it is simply finding a “nudge”!

  • haha, absolutely love lists. actually, I just love formatting and economy of language. the more concise, the better ;)

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