dylan’s Podcast explores entrepreneurship through the lenses of finance, faith, and the future. Drawing on real-world experience, he blends economic insight, personal stories, and quiet spiritual themes to challenge how we think about work and wealth. With a thoughtful, sometimes contrarian tone, each episode offers clarity and reflection—less about hustle, more about what’s worth building and why.
Episodes
Tuesday Jun 28, 2022
Tuesday Jun 28, 2022
Tune in for dylan's updates including:
[0:26] On-demand labour service update
[2:25] How do I hand my business over to someone?
[3:16] Blindspots we have as owners
[6:52] Who is your perfect customer?
[13:49] What value does your business offer customers?
[15:27] How is your product/service best made for?
[16:35] Why do customers use your business?
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Want to chat? Book a time: http://bit.ly/2rdDto2
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
Tuesday Jun 21, 2022
Tuesday Jun 21, 2022
Tune in for dylan's updates including:
[1:05] On-demand labour service update
[2:27] I am glad I spent time on a plan
[7:20] Moving from Struggling to Adjusting on the CFQ
[8:20] Cash in the bank does not mean you are profitable
[9:36] My experience with cash in the bank
How to get back on track:
[11:07] Why is your business not profitable?
[14:07] What do we need to do to correct what went wrong?
[17:38] How long is it going to take?
[18:27] What resources do we have/need?
[19:50] What are our next steps?
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Want to chat? Book a time: http://bit.ly/2rdDto2
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
Tuesday Jun 14, 2022
Tuesday Jun 14, 2022
Tune in for dylan's updates including:
[1:39] Coin laying off 18% of its workforce
[5:19] Don’t be “that” entrepreneur or business owner
[8:48] Netflix down 70% - uniqueness doesn’t last forever
[12:12] What is your unique competitive advantage?
[15:03] 80/20 rule for entrepreneurs and business owners
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
Tuesday Jun 07, 2022
Tuesday Jun 07, 2022
Tune in for dylan's updates including:
[1:16] Tweet - I could have made more money working for someone else
[3:00] Cash flow quadrant for business owners
[4:19] It’s hard to run a business
[4:48] Why bother having a business?
[6:11] Why I started a business
[10:47] What is an entrepreneur’s job?
[12:52] Why own a business?
[18:32] Why wake up every morning and go to work?
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
Tuesday May 31, 2022
Tuesday May 31, 2022
Tune in for dylan's updates including:
[2:03] Creating value versus consuming value
Tweet
[15:40] “what happens if we can make payroll?”
Market
[19:55] 18-24 months of needing to be careful
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
Tuesday May 24, 2022
Tuesday May 24, 2022
Tune in for dylan's updates including:
[00:53] Cash Flow Quadrant recap
[4:58] Multiple sources for revenue
[9:15] I stopped learning
Tweet
[14:39] Marshmallow experiment
[20:58] Don’t bury your head in the sand
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
https://wp.me/p2Ckbx-1BD
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
Tuesday May 17, 2022
Tuesday May 17, 2022
Tune in for dylan's updates including:
[1:15] Cash Flow Quadrant for Business Owners
[3:46] Managing personal burn rate
[5:26] Planning cash for our busy season
[6:56] On demand labour platform update
[8:56] Law of small numbers and maximizing what you have
Market News
[13:19] Layoffs and more jobs than ever are available
[15:54] US to raise rates to force inflation down
[19:09] Money doesn’t disappear - it moves
Tweet
[21:57] Wishful thinking
Watch this episode on YouTube:
Cash Flow Quadrant for Business Owners
https://wp.me/p2Ckbx-1BD
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
Tuesday May 10, 2022
Tuesday May 10, 2022
Tune in for dylan's updates including:
[00:58] Working on measured growth opportunities
[4:02] Managing tight cash flow
[7:21] Creating versus managing value
Market News
[9:29] Inflation is real and silent
[14:03] Crypto is unraveling
[19:24] Labour unionization strategy for Starbucks
Tweets
[24:52] Your business is not (most times) an ATM machine
[27:55] Use this time to build skills, solve problems
[30:54] Conflict delayed is conflict multiplied
Watch this episode on YouTube:
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
dylan's blog:
dylan's vlog:
Tuesday May 03, 2022
Tuesday May 03, 2022
Tune in for dylan's updates including:
[1:44] Real estate deal update
[3:42] On demand labour update
[6:52] Because of COVID we are lean and now need to grow
Market News
[8:38] Elon Musk / Twitter
[11:13] Amazon Netflix 1 month charts
[14:34] Unionization for Starbucks and Amazon
Tweets
[18:24] The further you are from the last bottom…
[21:06] There is no way around it - every win requires a certain *volume* of failure
[26:10] What you're currently trying to solve with process and policy is probably better solved by hiring better people
Watch this episode on YouTube:
Follow Dylan on Twitter:
@dylangallagher
Connect with dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
dylan's blog and podcast:
Tuesday Apr 26, 2022
Tuesday Apr 26, 2022
Tune in today as Dylan goes through his recent tweets about:
- limited time, limited resources
- getting the *right* people on your team
- competing on price
Follow Dylan on Twitter:
@dylangallagher
Watch the video for this episode:
Get your free instant business evaluation at:
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Connect with Dylan on LinkedIn at:
https://www.linkedin.com/in/gallagherdylan
dylan's blog:
dylan's vlog:
https://www.youtube.com/c/DylanGallagherVlog