Trust the Crazy

Trust the Crazy

Trust the Crazy! The Podcast for Fearless Entrepreneurs Trust the Crazy Podcast is a weekly podcast where Greg Dunkailo Davis walks you through multiple business topics and marketing topics as they relate to entrepreneurism. As entrepreneurs, our confidence can swing up and down as fast as the tempo of our favorite song - and sometimes it feels like we're losing our minds in the process. We wonder if we're crazy for starting the business. Crazy for believing in our vision. Crazy for working 80 hours for ourselves just to avoid working 40 hours for someone else. As a mentee of the late Dan Miller of 48 Days to the Work You Love, Greg continues the legacy of Dan's entrepreneurial inspiration with his own brand of storytelling, inspiration, and business strategy. Visit https://trustthecrazy.com/framework to get started.

Episodes

August 18, 2026 32 mins

No matter what age we are, we get stuck sometimes believing that we've done all we can do.  When faced with how to make a change, we have to look at the doors that are not necessarily closing but are tightening in on us.  What is happening for us that we can focus on bigger ideas?

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We're often caught up in looking for big opportunities.  We feel like we need to do something big and bigger instead of looking within the weeds for the small things we do that have a big impact.  This week, we'll focus on ways to better understand what wealth we're leaving in the weeds.

Resource:
Trust the Crazy Community

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August 4, 2026 32 mins

It's so easy for aspiring, launching, and growing entrepreneurs to overlook their personal experiences instead of seeing them as transferable skills to drive their entrepreneurial success.  I love the book, "Oh, the Places You'll Go" by Dr. Seuss.  But I think the older we get, the more we can look at our own experiences and realize it's all the places we've been that will drive our entrepreneurial success.

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July 28, 2026 32 mins

You may have encountered someone saying "Don't forget where you came from" as a way of keeping you from believing you're special.  Remembering where you came from can be looked at in two different ways.  You can choose to limit your success because of where you came from, or you can choose to be more than you ever dreamed of because of how you grew up.  Today we're going to talk about how to overcome limitations base...

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July 21, 2026 32 mins

Many people are afraid to ask for the opportunity.  They won't ask for the sale.  They won't ask for the favor.  The issue is that we've developed this mentality of creating an entire story of why someone will likely say no because of all sorts of reasons.  The issue is that we should all be focused on letting THEM say no instead of saying no for them.

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July 14, 2026 32 mins

When it comes to entrepreneurship, a decision to make is whether you can handle the uncertainty or if you need more perceived stability.  When we're thinking about entrepreneurship, we think about how uncertain it can be, but regardless of what we're doing as an entrepreneur, building stability is the true game plan.  The question is whether you're looking for stability through an employer or are you ready to build your o...

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July 7, 2026 32 mins

Certifications are excellent for gaining more tools in your toolbox, but they are not your primary value.  I see a lot of entrepreneurs hide behind their certifications.  They talk more about their credentials than they do the benefit of someone working with them.  In order to grow your business, you need to be sure you're explaining the change and impact you have more than the credentials that got you here.

Resource...

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June 30, 2026 32 mins

It's fairly safe to say that we all want to make a change, always.  Sometimes it's a small change, like ordering something other than our usual at our favorite restaurant.  Other times, it's significant, our career, our relationship with someone, our life goals.  Which comes first? Making the change or believing in the change?

Resources

Trust the Crazy Ask Greg

Trust the Crazy Community

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June 23, 2026 32 mins

Today, we're going to have an illustrated musical demonstration of how your business idea, products, and services evolve like a song.  Using my own song, "I Do Believe", which I also use as bumper music for the podcast, I demonstrate the way a song evolves from an idea to the fully produced version you hear.  Much like a song, your business idea and the way you talk about it need to be rehearsed and developed.  

...

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We all have struggled with elements of imposter syndrome.  Regardless of where it stems from, the issue is that we're giving an unknown body of people or someone close to dictate our level of confidence.  We worry about what someone will think of us instead of believing that people out there can benefit from our experience and passion.

Resources: 

Trust the Crazy Framework

Trust the Crazy Community

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June 9, 2026 32 mins

Looking for perfectionsim before we launch is holding us back more than it helps us.  Most growing entrepreneurs get this already, but for aspiring and launching entrepreneurs, there's a great deal of hesitation in making changes.  It's overworked, overthought and ultimately underdone.  In life, we're handed messes or create our own, but we work through them.  The same is true in entrepreneurship.  The soon...

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June 2, 2026 32 mins

Sometimes we are too complicated in our offer and we make it harder for someone to buy from us.  There's a time and place for telling stories, but when it comes to the sales process, we need to be really clear in what we want our prospective customer to do.

Resources:
Trust the Crazy Framework
Trust the Crazy Community

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May 26, 2026 32 mins

With summer upon us, it's easy to become distracted.  Whether it's vacations or the common issues of your prospects being on vacation and tuning out decisions during the summer, this is not the time to be complacent.  Let's focus on the things we can do this summer to make our business grow...or be ready to grow when your prospects are back in action.

Resource:
Trust the Crazy Framework
Trust the Crazy Community

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It can be hard in entrepreneurship to overcome the all-or-nothing attitude.  We want things to be all ironed out, perfectally lined up to meet 100% of our vision, our interest, or growth.  The reality is that 50% of something is better than 100% of nothing.  Most success comes from making small deposits over time and the more and more you contribute 50% of the way vs. waiting for the 100%, you get farther, faster.

Re...

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May 12, 2026 32 mins

When it comes to developing our services or product offers, we often overdo it by adding on too many benefits.  We feel like we need to just keep adding on the features in order for it to have value.  But, that's not often the case.  When we niche down, we create more value.  But, then the issue becomes, what to niche down to?  That's where we have to be good listeners and pay attention to the questions tha...

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May 5, 2026 32 mins

When it comes to understanding what type of service or product we may want to offer, sometimes we need to look at our story.  What did we go through that if we could do it differently now, we would.  That might just be a clue as to what type of service we should consider offering to others.  When we understand that, we can begin to build our story as to why we offer what we do.  Brand is the product we sell plus...

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April 28, 2026 32 mins

If we don't have new problems, we're likely not growing.  The good things about problems are that once they're solved, they can serve as inspiration to others.  You may just have a solution to someone else's problem because you've gone through it before.  When we're trying to decide what to do or be in our entrepreneurial journey, it may not be a continuation of what our career was as an employee, but instead it may ...

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April 21, 2026 32 mins

It's estimated that there are 73 million Americans who will retire by 2030.   A lot of people who are looking at retirement don't necessarily want to stop work as much as they just want more indepedence with their work.  They don't want to be in the 9-5 grind anymore, but don't want to simply sit around doing odd jobs.

This week, we'll talk about how to address the transition from retiree to entrepreneur.

Resources:<...

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April 14, 2026 32 mins

Our ability to prioritize profitable work vs. busywork greatly depends on our ability to make profitable decisions.  Ones that are strategically aligned with our business' growth vs. busywork that leaves us feeling burnout.  This week, we tackle some strategies and culprits that attack our ability to be profitable entrepreneurs when we're wearing multiple hats.

This week's Resources:

Thought Leader Sales & Marketing F...

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April 7, 2026 32 mins

Are you getting stuck in comparison mode?

Theodore Roosevelt said "Comparison is the thief of joy."  When we focus too much on what's outside of us, how our competitors are doing, the way we perceive if we're ahead or behind them, it steals the joy of what we do as entrepreneurs.

Today, we discuss the importance of knowing when we're in the right place for ourselves.  We'll tackle ways to not let ourselves get caught up i...

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