loader from loading.io

The #1 Reason People Never Start Their Dream Business

Entrepreneurship Simplified

Release Date: 04/23/2025

The #1 Reason People Never Start Their Dream Business show art The #1 Reason People Never Start Their Dream Business

Entrepreneurship Simplified

If you’ve been sitting on an idea, waiting to feel confident before you start your business, I get it. I’ve been there. But I’m telling you right now, confidence isn’t the thing that’s holding you back. It’s clarity. In this episode, let’s talk about why I believe clarity beats confidence every time; especially when you’re starting out. I wasn’t super confident when I launched my first business (or my second, or third, for that matter). But what kept me moving forward was knowing what I was doing, who I was doing it for, and how I was going to make money doing it. That’s...

info_outline Why Most Startups Fail—and What Real Entrepreneurs Do Next show art Why Most Startups Fail—and What Real Entrepreneurs Do Next

Entrepreneurship Simplified

So here’s the thing... Most people talk about entrepreneurship like it’s this glamorous, straight shot to success. But if you’ve ever actually started something, you know it’s more like a rollercoaster with no seatbelt.  In this episode, I sat down with my friend Doug Milbauer, who’s been through it all: 11 startups, multiple industries, wins, losses, pivots, and plenty of “What was I thinking?” moments.  Doug shares how he went from dropping out of college to jumping into real estate in Austin during a boom, then starting businesses in places he didn’t even fully...

info_outline Are You Hiring Too Fast and Firing Too Late? show art Are You Hiring Too Fast and Firing Too Late?

Entrepreneurship Simplified

Ever felt like you hired someone just to fill a gap and then paid for it later? Yeah, me too. I’ve been there more times than I care to admit. In this episode, I wanted to speak directly to business owners and entrepreneurs who feel the pressure to hire fast but aren’t always confident they’re making the right call. I recorded this one pretty spontaneously, but it’s something that’s been on my mind a lot lately, especially with the work I’ve been doing at Boxed Business Solutions. Hiring used to be something I dreaded because, truthfully, I wasn’t very good at it. I’d hire...

info_outline My 10 Year Old Got Punished at School for Doing Exactly What I Get Paid to Do show art My 10 Year Old Got Punished at School for Doing Exactly What I Get Paid to Do

Entrepreneurship Simplified

So this episode wasn’t planned. But I had to hit record and talk about what just happened with my 10-year-old. He got in trouble at school… for doing something I literally get paid to do. The kid launched his first little business. Saw a gap in the market — the school store didn’t have stickers — so he convinced my wife to buy a bunch on Amazon, then turned around and started selling them to the third and fourth graders for bluff bucks. He even brought in a couple friends, gave them a handful of stickers, told them they could keep part of what they made, and boom — he built a sales...

info_outline 3 Cafes, 5 Years, and One Big Lesson in Entrepreneurship show art 3 Cafes, 5 Years, and One Big Lesson in Entrepreneurship

Entrepreneurship Simplified

Starting a business is never easy—and if we’re being honest, most of us just figure it out as we go. In this episode, I sat down with Joel and Dexter from Hemispheres Cafe, and man, this conversation hit home. These guys opened up about what it’s really like to start something from scratch—not just the Instagram version of entrepreneurship, but the real stuff. Like sitting in a backyard wondering if coffee could be more than just something you drink, and then making a decision that changes everything. We got into the messy parts—trying to launch in the middle of COVID, pivoting into...

info_outline Launching a Business with Less Than $1,000 — Is it Possible? show art Launching a Business with Less Than $1,000 — Is it Possible?

Entrepreneurship Simplified

Starting a business without a lot of money sounds impossible, right? You hear people talk about getting loans, finding investors, and having to drop serious cash on inventory. It can feel like you need a mountain of money just to get started. But what if you could launch a business with less than $1,000? Is that really possible, or just a pipe dream?   In this episode, I share what it’s really like to bootstrap a business — to make it work with what you have. I talk about my own experience of trying to start a business from scratch and the struggles of getting traditional funding. Let...

info_outline Hiring, Pricing, and Scaling: Lessons from a Small Business Owner show art Hiring, Pricing, and Scaling: Lessons from a Small Business Owner

Entrepreneurship Simplified

Leaving a stable six-figure job to start a business from scratch isn’t for the faint of heart—but for Brian Owens, it was the only way forward. In this episode, Brian shares his journey from being an electrician in the oil field to building his own electrical contracting business in Corpus Christi. He talks about the tough early months, the challenges of finding reliable employees, and the lessons learned from setting up the business structure. We also discuss what it really takes to stand out in a competitive industry—hint: answering the phone and showing up go a long way! If you’re...

info_outline The 3 Fatal Mistakes That Sink New Businesses—And How to Avoid Them show art The 3 Fatal Mistakes That Sink New Businesses—And How to Avoid Them

Entrepreneurship Simplified

A lot of new businesses don’t fail because the idea is bad—it’s because of a few key mistakes that could’ve been avoided. In this episode, I’m breaking down the three biggest ones I see all the time so you don’t have to learn the hard way. First, just having a great skill or product isn’t enough. If you don’t have a plan to actually get customers, your business won’t last. Then there’s the issue of money—too many people jump in without enough cash to keep things going long enough to get off the ground. And finally, trying to do everything yourself? That’s a fast track...

info_outline Is Your Business Stuck? Here’s Why Most Entrepreneurs Struggle to Grow show art Is Your Business Stuck? Here’s Why Most Entrepreneurs Struggle to Grow

Entrepreneurship Simplified

Is your business feeling stuck, like no matter what you do, growth just seems out of reach? Many entrepreneurs struggle to take their business to the next level, often falling into common pitfalls without even realizing it. So today, I’ve invited my good friend Neal Maier from Tread Partners to talk about why. Neal has seen firsthand where business owners can go wrong—especially when it comes to digital marketing—and he shares the biggest mistakes he has seen and what you can do differently. We talk about everything from go-to-market strategies to budgeting mistakes and why so many new...

info_outline Welcome to Entrepreneurship Simplified—This Is Not Your Average Business Podcast show art Welcome to Entrepreneurship Simplified—This Is Not Your Average Business Podcast

Entrepreneurship Simplified

This is it—the launch of Entrepreneurship Simplified. Not just another business podcast. Not a bunch of fluff. Just real talk about what it actually takes to start and grow a business. In our very first episode, let me share my personal story—how I dropped out of college to start my first real business, the wins, the losses, and everything in between. Entrepreneurship isn’t easy, but it’s possible. And if you’ve been sitting on an idea, waiting for the right time, maybe this is your sign. I’ll be sharing what I’ve learned over the years, bringing on guests who’ve built...

info_outline
 
More Episodes

If you’ve been sitting on an idea, waiting to feel confident before you start your business, I get it. I’ve been there. But I’m telling you right now, confidence isn’t the thing that’s holding you back. It’s clarity.

In this episode, let’s talk about why I believe clarity beats confidence every time; especially when you’re starting out. I wasn’t super confident when I launched my first business (or my second, or third, for that matter). But what kept me moving forward was knowing what I was doing, who I was doing it for, and how I was going to make money doing it.

That’s what clarity gives you: direction.

It calms the nerves.

It doesn’t mean the fear goes away, but it does mean you’ve got a plan to come back to.

I also share a real-life example from when my wife opened her lash lounge, and how her prep and planning gave us the clarity we needed to say yes, even though the business was in a completely different state. We didn’t wait to feel 100% ready. We just had a solid plan, and that was enough to take the leap.

So if you’ve got a dream, but you’re stuck in perfection mode or just feeling paralyzed by the “what ifs,” this episode is for you. I hope it helps you reframe the way you think about confidence and gives you the push to finally get started.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:19 - The mindset shift that changes everything when you’re starting out

01:32 - The role of clarity in business planning

02:58 - Overcoming fear and analysis paralysis

04:45 - Defining your market and your customer

08:14 - Clarity in action: The eyelash lounge example

10:01 - Three ways to get clarity

13:25 - Final thoughts on confidence vs clarity when starting a business

RESOURCES:

If you enjoyed today’s podcast, don’t forget to subscribe, rate, and share the show! There’s more to come, so we hope to have you along with us on this journey!