You ever get one of those pieces of advice that just sticks with you? Katrina Calderon told me something in this episode that I haven’t stopped thinking about: “If you keep putting part-time energy into your full-time dreams, you’re never gonna get full-time results.” And man, isn’t that the truth. If you’re looking for tips for new entrepreneurs that aren’t all buzzwords and fluff, you’ll want to listen to this one.

Katrina is the CEO of Regal Fierce Media out of Tucson, Arizona, and her story is wild in the best way. We talk about how she got started, from watching reality TV in eighth grade to running her own agency with her husband and best friend. She didn’t come from a business background, didn’t have connections or funding, but she figured it out, one bold move at a time.

We got into the real stuff: what it’s like starting a business right before the pandemic, how scary it gets when the contracts dry up, and how a $10,000 loan changed everything for her team. She also shares how social media and showing up in the local community helped her grow, without relying on cold calls (which, if you know me, is music to my ears).

If you’re just getting started or thinking about making the leap, Katrina lays down some great, practical tips for new entrepreneurs, things like paying yourself first, staying visible, and building something with the right people around you. It’s a good one. Give it a listen.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:45 - Katrina shares how she got started in entrepreneurship

08:17 - When did Katrina know it was time to go full-time with her business

11:14 - Keith and Katrina compare how their families reacted to their business choices

13:09 - The unexpected challenges of sustaining a business

21:23 - Has networking become harder post-COVID?

24:32 - Katrina talks about balancing energy and choosing the right events

26:26 - Katrina’s advice for new entrepreneurs

ABOUT OUR GUEST:

Katrina Calderon is the CEO and co-founder of Regal Fierce Media, a Tucson-based digital marketing agency known for its strong community presence and bold creative work. A first-generation college graduate, Katrina earned a full scholarship to the University of Arizona, where she studied communications and built the foundation for her future in business. With a passion for storytelling, people, and social media, she launched her agency alongside her husband and business partner in 2019. Since then, she’s helped small businesses elevate their brand through strategic marketing, video production, and authentic connection—proving that with resourcefulness and heart, you can build something from the ground up.

CONNECT WITH KATRINA CALDERON:

• LinkedIn https://www.linkedin.com/in/katrina-calderon

• Website https://www.regalfiercemedia.com/

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

Some days, it just hits different. You wake up, stare at your calendar, and wonder if this is still what you want. That’s the part of mental health in business no one really prepares you for.

In this solo episode, I’m just being real with you. I’ve been talking to a lot of entrepreneurs lately, people just like you and me, and the same thing keeps coming up: burnout, frustration, and this feeling of being totally alone in the journey. So I decided to hit record and share what’s been on my heart, because I know how heavy it can get.

I talk about how I’ve learned to take better care of my mental health in business, whether it’s through honest conversations with people I trust, journaling during my quiet time, or even just taking time to go fishing and clear my head. These aren’t groundbreaking ideas, but they’ve changed the game for me. And if you’re in that space where it’s starting to feel like too much, I hope this helps you breathe a little easier.

Mental health in business is something we have to talk about. It’s not always going to be sunshine and success. But with the right support and space to reset, you really can keep showing up; for your business, your family, and yourself.

EPISODE HIGHLIGHTS:

00:00 - Introduction

02:03 - The role of support systems in entrepreneurship

05:02 - Strategies for mental health and recharging

07:04 - The importance of self-care and mental well-being

09:50 - Encouragement to focus on mental health

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

Have you ever had to slow down your business because you didn’t have the cash to keep going, even though your marketing was working and your inventory was flying out the door? I’ve seen it happen more times than I can count. That’s why I wanted to bring Ciaran MacWhite on the show, because so many founders are making one of the most common startup funding mistakes without even realizing it.

In this chat, Ciaran breaks down why giving up equity just to cover short-term expenses is a move that can cost you big; like control of your business, decision-making power, and future profits. He talks through smarter alternatives, including what his company WayFlyer is doing to help brands get fast, unsecured working capital without dealing with banks or handing over a slice of the business. If you’re in eComm, especially apparel, beauty, or health, you’re gonna want to hear this.

We also get into the mindset shift that happens when a side hustle turns into a multi-million dollar operation. You start off doing everything yourself, but there comes a point where bringing in expert help, like a fractional CFO, can save you a lot of headache. And when it comes to money, knowing your options is everything.

So if you’re in that messy middle of growth and debating how to fund your next step, don’t miss this one. We talk through real stories, real numbers, and real lessons to help you avoid the most common startup funding mistakes that trip founders up again and again.

EPISODE HIGHLIGHTS:

00:00 - Introduction

01:22 - What does Wayflyer do and how does it support eCommerce brands?

04:32 - What are the biggest mistakes founders make with funding?

07:18 - Why is negotiating supplier terms so important for cash flow?

10:05 - Why using equity for short-term expenses is a bad move

12:04 - When should founders bring in fractional experts like CFOs or CMOs?

15:32 - What are the warning signs that a business might be in financial trouble?

17:32 - What does the average WayFlyer client look like?

19:32 - How Wayflyer helped brands like True Classic and Daniel Patrick scale

21:28 - What trends are shaping the future of eCommerce funding?

ABOUT OUR GUEST:

Ciaran MacWhite is a Funding Manager at WayFlyer, where he partners with eCommerce founders to provide non-dilutive capital solutions that support business growth without sacrificing equity. Specializing in bridging cash flow gaps and enabling inventory scaling, Ciaran works closely with brands to tailor financing strategies that align with their unique needs. His approach emphasizes flexibility and speed, helping clients overcome traditional funding hurdles and achieve sustainable expansion. Through his role, Ciaran contributes to WayFlyer’s mission of empowering consumer brands with purpose-built financing solutions.

CONNECT WITH CIARAN MACWHITE:

• LinkedIn https://uk.linkedin.com/in/ciaran-macwhite-826093bb

• Website https://wayflyer.com/

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

Think starting a side hustle is hard? I just don’t buy that anymore. Not when I can get a 10-year-old boy and an 11-year-old girl; my kids, to launch their own little businesses in a single weekend using tools like ChatGPT, Gemini, and Claude. In this episode, I’m breaking down exactly how we’re doing it and why I truly believe this might be the easiest side hustle to start in 2025 (with a little help from AI.)

My son’s working on a lemonade stand to raise money for our church. My daughter? She’s starting a jewelry business to earn some spending money. And we’re letting AI help us with everything, coming up with business names, designing logos, even getting a basic website layout. We’re not overthinking it. We’re just taking action, and AI is going to help us speed everything up.

I also talk a bit about my own journey; how I started selling painted rocks as a five-year-old (don’t ask me why anyone bought them), to building businesses like Gelatin Digital and Boxed Business Solutions. Some started as side hustles, and some fizzled out, but every one of them taught me something. Now with AI, what used to take me weeks takes a couple of hours.

So if you’re someone who’s been sitting on a business idea, wondering how or when to start—here’s your sign.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:38 - My kids wanted to start summer side hustles

01:17 - Childhood hustles and early business attempts

01:50 - Using AI to build the kids’ businesses

04:20 - How ChatGPT helped name Keith’s own companies

04:52 - The origin of Boxed Business Solutions

05:36 - Why starting a side hustle is easier than ever

07:03 - Free tools vs. hiring help

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

I’ve had a lot of conversations on this show about starting a business, but today’s episode is a little different. I sat down with my good friend and neighbor, Josh Dale, who, by the way, also happens to be my son’s baseball coach, to talk about why he hasn’t taken that leap into entrepreneurship yet.

Josh recently retired after over 20 years in the Navy, and now he’s standing at a bit of a crossroads. The desire to start something is there. The work ethic? Rock solid. But like a lot of smart, capable people, he’s stuck in that space between wanting to build something and not knowing exactly what that “something” is. And more than anything, he doesn’t want to fail.

We talked a lot about what makes people hesitate, how it’s not always about the money or fear of hard work. Sometimes it’s the unknown, the risk to your time, your energy, your confidence. Josh was super honest about where he’s at right now, how having that military retirement gives him peace and security, but maybe also gives him just enough comfort to not feel the urgency to pull the trigger.

If you’ve ever found yourself in a season where you know you’re built for more, but you’re not quite sure what “more” looks like, or how to get there, this conversation might sound familiar. Josh may not have all the answers right now, but his story is one a lot of folks can relate to.

EPISODE HIGHLIGHTS:

00:00 - Introduction

01:17 - What’s holding you back from starting a business?

06:05 - From navy life to civilian questions: What’s next?

08:35 - Should I take the leap or play it safe?

12:29 - The real reasons people don’t start: Doubt, comfort, and waiting for the perfect idea

16:47 - What does success really look like for Josh?

ABOUT OUR GUEST:

Joshua Dale is a recently retired Navy veteran who served over 20 years as a hospital corpsman. With a strong background in discipline, leadership, and service, Josh is now navigating the transition to civilian life and exploring what’s next; whether that’s entrepreneurship, a new career path, or meaningful community involvement. Known for his integrity, work ethic, and commitment to others, Josh brings a thoughtful and honest perspective to conversations about risk, purpose, and redefining success after military service.

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

You’ve hit your revenue targets. Your team seems productive. On paper, everything’s working... So why does it feel like the wheels are about to fall off? Let me tell you, I’ve been there. I’ve sat in that CEO chair, patting myself on the back for “crushing it,” only to realize later I was inches away from disaster. And honestly? It’s terrifying how easy it is to miss the cracks until they swallow you whole.

I’ll never forget the day I hired a consultant who ripped off the blindfold. I thought I ran a tight ship: great culture, clear goals, everyone aligned. Turns out? My employees were frustrated, my mid-level managers were borderline toxic, and half the processes I bragged about? Pure fiction. It was embarrassing. But here’s the kicker: every entrepreneur does this. We get so obsessed with looking successful that we stop asking the hard questions. We ignore the whispers (or outright warnings) from our teams. We confuse motion for progress.

But here’s what I learned the hard way: “success” is a trap if you’re not willing to get real. In this episode, I’m spilling the unfiltered truth about the red flags I missed, the ego that nearly sank me, and the moment I had to admit, “Man, I don’t have a clue.” I’ll walk you through the exact steps I took to rebuild trust, fix my leadership blind spots, and turn a stagnant business into one that actually thrives.

Spoiler: It starts with swallowing your pride. If you’re ready to stop pretending and start growing, this one’s for you.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:52 - Why people dread starting businesses

02:37 - Keith’s personal experiences with coaching and consulting

04:58 - The impact of coaching and consulting on business growth

07:30 - The common misconception that big businesses have everything figured out

09:17 - Let’s talk about company culture and employee engagement

11:12 - The role of coaching and consulting in personal and professional development

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

You know what’s wild? Most startups don’t fail at getting funding because they’re a bad idea or don’t have potential, it’s because they’re not prepared. In this episode, I sit down with Zac Smith from LendingWISE to break down why so many business owners struggle to get the money they need.

Zac’s been in the trenches with business owners all over the country, and he breaks down the biggest mistakes people make; from not having a clear use of funds (he uses a grocery store analogy that totally nails it) to waiting until they’re in a crisis before reaching out for help. And if you’ve ever tried going the traditional bank route and ended up frustrated, trust me, you’re not alone. Zac explains exactly why most banks say no, and what options you do have.

We got into some real talk about using credit cards to fund businesses, hard money loans, SBA programs, and how the whole lending process actually works. Zac even shared stories of clients who were drowning in debt with $80k a month in payments, and how his team helped cut that by more than half. That’s the kind of behind-the-scenes stuff you don’t hear often.

So if you’re growing fast, trying to scale, or just feeling stuck, this episode’s going to hit home. Zac’s not here to sell magic solutions...he’s giving the real, practical advice that could literally save your business. Give it a listen. You’ll be glad you did.

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:47 - What LendingWISE actually does for small businesses

01:40 - Who are LendingWISE’s ideal customers?

02:46 - Can you get capital from LendingWISE no matter where you are?

03:37 - The most common funding mistakes business owners make

08:40 - Can you get funding if you’re just starting out?

13:44 - SBA Loans: Everyone talks about them, but who actually qualifies?

17:08 - If you’re scaling fast, you’re probably getting rejected

23:21 - What’s next for business lending? (and how AI changes the game)

ABOUT OUR GUEST:

Zac Smith is the Owner and Managing Partner of LendingWISE, LLC, bringing over 15 years of experience in non-bank finance and leasing. For the past six years, he has worked directly with small business owners, focusing on expanding access to capital and helping them become bankable. Zac specializes in assisting businesses in the restaurant, trades, and retail sectors. At LendingWISE, Zac is committed to providing small business owners with the support they need to secure funding, offering services that include small business loans and tax incentives. His mission centers on helping entrepreneurs navigate the complexities of business financing and achieve their growth objectives. 

CONNECT WITH ZAC SMITH:

• LinkedIn https://www.linkedin.com/in/zac-smith-small-business-loans-made-simple

• Website https://teamlendingwise.com/meet-the-team

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

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:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

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 understand yet. Some of them took off. Others? Crashed hard. We talk about what happens when a business looks good on paper but completely falls apart in real life. And more importantly, what you do next. 

We hit on some real stuff here. Like why educating the market is so expensive (and risky), how most people aren’t actually willing to do the work, and why you should not compete on price unless you own the whole supply chain. Doug also opens up about the times he should’ve walked away sooner, but didn’t, and the cost of holding on too long.

If you’ve ever felt the sting of a failed idea or the pressure of making your business work because your identity is wrapped up in it, you’ll feel this one. This conversation isn’t just for entrepreneurs, it’s for anyone who’s ever taken a big risk, fallen flat, and had to ask, “Now what?”

💥 What happens when the dream doesn’t work

📉 Learning to say “no-go” before wasting time and money

💡 Ideas are great, but only if people actually want them

🚫 Stop giving CPR to dead business ideas

EPISODE HIGHLIGHTS:

00:00 - Introduction

00:58 - Doug’s background and entrepreneurial experience

02:45 - Starting, scaling, and losing two businesses

06:47 - "How hard could it be?” – Starting a construction company

09:04 - Hitting the jackpot: The dream business model

10:36 - Reflections on emotional and financial resilience as serial entrepreneurs

15:36 - The risks of spending your whole runway teaching customers they have a problem

20:58 - Why product-based startups, especially without funding, are incredibly risky

24:13 - Doug and Keith share personal experiences of clinging too long to a failing idea

26:40 - How entrepreneurs can detach their self-worth from their ventures

27:52 - Doug’s biggest lesson in entrepreneurship

ABOUT OUR GUEST:

Doug Milbauer is the Director of the Coastal Bend Business Innovation Center and an Assistant Professional Professor at Texas A&M University–Corpus Christi. With over 35 years of experience in entrepreneurship, sales, marketing, and management, he has founded ten startups across various industries and led two intrapreneurial ventures, including one with a NYSE-traded company. Milbauer holds a BBA in Marketing from the University of Texas at Austin and both an MBA and an MS in Entrepreneurship and Organizational Behavior from the University of Texas at Dallas. He is currently pursuing a PhD in Entrepreneurship. Before joining TAMU-CC, he taught at institutions such as Stephen F. Austin State University, UT Dallas, Texas Christian University, and the University of North Texas. His vision for the CBBIC is to foster entrepreneurship and venture creation among students, faculty, and the Coastal Bend communities.

CONNECT WITH DOUG MILBAUER:

• LinkedIn https://www.linkedin.com/in/dougmilbauer/

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified

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 based on instinct or likeability, and that only works for so long. Over time, I’ve figured out a more systematized approach: mixing in things like behavioral assessments and even a little AI to help clients (and myself) make better decisions. It’s not about being perfect, but it is about being intentional. And once you start tracking what works and what doesn’t, you begin to see patterns that really help.

But the part we don’t talk about enough is firing. It’s uncomfortable. It feels personal. Even when someone’s clearly not a good fit, letting them go can be gut-wrenching. I walk through the process I use now, one that’s respectful, clear, and keeps things from dragging on way too long. It’s about setting expectations early, giving people a chance to improve, and being firm when it’s time to move on.

If you’ve ever hired someone because you were desperate or kept someone way past the point you should’ve, this episode will speak to you. I’m sharing what I’ve learned the hard way, in hopes it saves you some stress (and maybe even your company culture). And hey, if you’ve got questions or want to talk more about how to get better at this stuff, I’m always up for that conversation.

EPISODE HIGHLIGHTS:

00:00 - Introduction

01:17 - The trap of hiring too fast

02:36 - The benefits of systematizing your hiring process

04:50 - The power of behavioral assessments

06:19 - Why firing still sucks

07:32 - The 3-strike system I use

11:42 - Keeping it fair but firm

RESOURCES:

• Visit our website: https://www.boxedbiz.us

• Are you ready to start your own business? Take our assessment test to find out now: https://boxedbiz.us/assessment-quiz/

• Follow us on Facebook https://www.facebook.com/profile.php?id=61572485474163

• Follow us on Instagram https://www.instagram.com/boxedbusinesssolutions/

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!

• Subscribe on Apple Podcasts https://podcasts.apple.com/us/podcast/entrepreneurship-simplified/id1795820700

• Subscribe on Spotify https://open.spotify.com/show/5UPcoSEh2nmjfJWc4doXfc?si=247bfe2c43c44afa

• Subscribe on YouTube: https://www.youtube.com/@entrepreneurshipsimplified