The Reluctant Entrepreneur Podcast

Most people start a business because they want more freedom, more control, and the opportunity to build something of their own. 

But somewhere along the way, many entrepreneurs discover that they haven’t created freedom at all. They’ve created a demanding job with an unreasonable boss: themselves.

My guest today is Louis Swart, a business builder, coach, author, and founder of Ironbrij. Over a career spanning more than 35 years, Louis has built and sold companies, managed hundreds of employees, and learned firsthand what happens when a business becomes too dependent on its owner.

His f...

Sometimes the career that looks safest is the one quietly taking you in the wrong direction. The résumé gets stronger. The paychecks keep coming. Every outward measure says you’re succeeding. 
But somewhere inside, you realize that each step forward is carrying you farther from the work you were meant to do.

Joshua Lee grew up in a small Alaskan town as the son of Korean immigrants. His family faced physical disabilities, financial hardship, and the kind of uncertainty that teaches you how to become resourceful long before you understand what entrepreneurship means.

Joshua went...

Most people who discover that their building is wasting hundreds of thousands of dollars complain about it.

My guest today helped organize a board takeover, fixed the problem, and accidentally discovered a business opportunity hiding inside the chaos.

Some businesses begin with a carefully researched idea, a detailed plan, and a founder determined to become an entrepreneur. Others begin with a frustrating question: Why do the costs keep going up when no one can explain where the money is going?

My guest today wasn’t searching for a business opportunity. She was trying to un...

Successful business owners rarely ignore exit planning because they don’t care about the future. They postpone it because the business is thriving, customers keep coming, and leaving still feels years away. But waiting too long can reduce a company’s value, limit an owner’s options, and turn an expected transition into a difficult financial and personal crisis.

We’ve explored exit planning with other guests, but this conversation examines it through a very different lens. Matt DiFrancesco is a Financial Advisor and Certified Exit Planner™ who has built his practice around the collision repair industry. These businesses...

Most entrepreneurs spend their time thinking about how to build a business.
How do I find customers?
How do I increase revenue?
How do I grow faster?
'
But far fewer stop to ask a different set of questions.
What happens if my partner and I have a falling-out?
What happens if the business is sued?
What happens if I become seriously ill or die?

And what happens to everything I’ve worked so hard to build if I never created a plan to protect it?
Those aren’t part...

Building a successful business is difficult. Building one, watching it begin to fall apart, and then finding the courage to start again is something entirely different.

Entrepreneurship is often presented as a steady climb. You start with an idea, work hard, gain momentum, and eventually arrive at success. 

But for many entrepreneurs, the real journey looks nothing like that. It includes exhaustion, financial pressure, painful decisions, and moments when the person behind the business begins to disappear beneath the weight of keeping it alive.

My guest today is Joshua Griffin, an award-winning entrepreneur, marketing s...

There’s a dangerous moment in entrepreneurship that doesn’t get talked about nearly enough. It’s the moment when your business starts looking successful from the outside, but inside, you realize you’ve created something that can’t function without you.

The revenue is growing. The customers are coming in. Employees are depending on you. By almost every traditional measure, things are going well.

Except you can’t leave.

Every decision still comes across your desk. Every problem eventually finds its way back to you. And instead of owning a business, the business starts owning...

Some entrepreneurs spend years planning the business they hope to build. Others answer the phone, agree to help one client, then another, and eventually look around and realize they’ve accidentally created a company.

But building a successful business by accident doesn’t mean the lessons come easily.
Sometimes success can hide the underpricing, the wrong opportunities, the inability to say no, and a business that depends too heavily on the person who started it. The real test comes when you have the opportunity to build again.

Do you repeat what worked, or do you fina...

Most entrepreneurs start a business because they want more freedom. But as the company grows, many discover that they haven’t created freedom at all. 

They’ve created a business that depends on them for every decision, every approval, and every solution. Instead of owning the business, the business begins to own them.
At some point, the founder who built the company can become the very person preventing it from reaching the next level.

My guest today has spent much of his career helping entrepreneurs overcome the very challenges I just described. 

He’s built te...

Some entrepreneurs spend their careers becoming experts in one industry. Others keep walking away from what they know, entering unfamiliar territory and betting that the lessons from their last chapter will somehow prepare them for the next one.

But moving from Hollywood to venture capital, and then into one of the most complicated, regulated, and emotionally charged industries in America, isn’t simply a career pivot. 
It’s a decision to build where trust, responsibility, customer uncertainty, and government regulation all collide.

My guest today has spent much of his career betting on ideas, creative peopl...

What if the very thing you spent your life trying to hide eventually became the foundation of your business?

For many people with dyslexia, the challenge isn’t limited to reading, writing, or processing information differently. 

It can shape confidence, career choices, relationships, and the way they measure themselves against everyone around them. When the world repeatedly tells you that your mind doesn’t work the “right” way, it’s easy to assume the problem is you.

But what happens when you stop trying to think like everyone else? What happens when you begin building ar...

Most entrepreneurs are hunting for something. Some are hunting for money. Some are hunting for freedom. Some are hunting for purpose, identity, or a second chance to build a life that actually feels like their own.

But today’s guest took that idea a little more literally.

After building and franchising a chain of retail stores, my Guest reached a point in life where a lot of people might have chosen comfort, predictability, and the safety of what they already knew. 

Instead, he made a different choice. He stepped away from one version of suc...

Most business owners are told that growth comes from doing more. More advertising. More content. More technology. More leads. More tactics.

But what if a company’s growth problem isn’t a lack of activity? What if the real problem is that no one truly understands why customers make the decisions they make?

Today’s guest, Rich Smith has spent more than 30 years answering that question from inside some very high-stakes organizations. 

He helped lead AIG Bank’s marketing transformation during the 2008 financial crisis, rebuilt Ditech into a top-10 mortgage originator, helped scale Recovery Centers of...

Reliability Matters at 200: 
The Conversations, Lessons, and People Behind the Podcast

Reliability Matters has reached its 200th episode.

In this special solo episode, host Mike Konrad looks back at the conversations, ideas, and people who have helped shape the podcast. Rather than focusing on a single guest or technical subject, this episode celebrates the broad range of reliability topics explored throughout the program.

Over the years, Reliability Matters has examined printed circuit board design, electronics assembly, soldering, cleaning, contamination, conformal coating, inspection, testing, failure analysis, harsh-environment reliability, artificial intelligence, cybersecurity, supply-chain challenges, industry s...

Have you ever met a successful business owner who says, “I love spreadsheets and financial reports”? Probably not. 

For most entrepreneurs, the financial side of the business is often the most confusing, intimidating, and sometimes even avoided part of running a company.

But here’s the reality: if you don’t understand your numbers, you’re essentially flying blind.

My guest today, Justin Boyd, has spent more than two decades in finance and accounting helping businesses make sense of their numbers and use them to make smarter decisions. 

Today he works with entrepreneur...

Most entrepreneurs spend an enormous amount of time thinking about their products, customers, competition, revenue, and expenses. But there's another force operating inside every company. It influences who stays, who leaves, how decisions are made, how customers are treated, and whether success energizes people or slowly burns them out.

What's that force? Culture. Every business has one, whether the founder creates it intentionally or simply allows it to develop on its own. And while culture can sometimes sound like a vague collection of mission statements, employee perks, and motivational slogans, today's guest believes it's something far more consequential...

What happens when the dream you risked everything to build is no longer the business you’re meant to lead? Do you hold on because of the time, energy, and identity you’ve invested in it? Or do you accept that entrepreneurship sometimes requires you to reinvent not only your company, but yourself?

Today’s guest left the security of a conventional career to pursue his dream of working in sports. 
That decision led him into sports media, content creation, podcasting, coaching, leadership, and eventually the rapidly changing world of artificial intelligence.

His journey demonstrates that ent...

Most entrepreneurs start a business because they want more freedom. But somewhere along the way, many of them build a company that can’t make a decision, serve a customer, or solve a problem without them.

They’ve become the founder, the manager, the troubleshooter, and sometimes even the administrative assistant.

So how do you begin letting go without losing control? How do you delegate when explaining the work feels harder than doing it yourself? 

And how do you build simple systems that allow the business to operate without the founder sitting in the middle...

Entrepreneurs are taught that nearly every business problem can be solved with more effort, a better strategy, or another expert telling us what we should do next. 

But what happens when the business is growing, the strategy appears sound, and you’re still exhausted, hesitant, or unable to move forward?

Sometimes the obstacle isn’t in the business plan. It’s buried beneath years of pressure, fear, disappointment, and beliefs we may not even realize we’re carrying.

Today’s guest believes that many successful entrepreneurs aren’t suffering from a lack of ambition or informatio...

Growth is usually treated as proof that a business is working. But growth has a way of exposing every weakness a smaller company can hide. The founder becomes the answer to every question. Follow-up starts falling through the cracks. 
'
Systems bend under the pressure. And the business that was supposed to create freedom begins demanding more and more from its owner.

So, what happens after the breakthrough, when success forces you to rebuild the way the business actually works?

My guest today is Bennett Maxwell, and, if he looks familiar, this is his se...

A lot of entrepreneurs don’t begin with a grand business plan. 

Sometimes they begin with a layoff, a book idea, a little fear, a little curiosity, and the need to figure things out before the rent comes due.

Today’s guest, Liz H. Kelly, knows that path well. After writing and promoting her own dating book, Liz discovered the power of publicity firsthand. 

Later, after leaving the corporate world, including a role at MySpace, she took the leap into entrepreneurship and built Goody PR, an agency focused on helping people magnify their good throug...

Most entrepreneurs start a business because they want more freedom. Then, somewhere along the way, they become the person who must approve every decision, answer every question, and solve every problem. The business may be growing, but the owner is trapped inside it.

My Guest today, Jennifer Staats understands that problem because she lived it. 

After beginning her career in real estate, she discovered that her real talent wasn’t simply selling properties. It was building the systems, workflows, and teams that allowed other people to perform at their best. 

After becoming a mother, Jenni...

A lot of entrepreneurs think branding starts with a logo, a color palette, a website, or maybe a clever tagline. 

But today’s guest would probably argue that’s where branding shows up, not where branding begins.
Solveig Petch, also known as Petchy, is a strategic brandsmith who helps businesses become brands and brands become legacies. Her work sits at the intersection of strategy, identity, values, positioning, and long-term business growth.

But her story is not just about helping other people build brands. It’s also about what happens when the business you helped build no long...

Most business owners think they have a marketing problem. They need a better website, more social media, better SEO, maybe a few videos, maybe some paid ads.

But today’s guest would probably say, “Not so fast.”

Because very often, what looks like a marketing problem is really a positioning problem, a messaging problem, a customer understanding problem, or maybe even a business model problem.

Gee Ranasinha is the Founder and CEO of KEXINO, a marketing agency working with startups and small-to-medium-sized B2B businesses. But his path didn’t begin in a marketing departme...

A lot of entrepreneurs think they have a marketing problem. They think they need a better website, more social media, a sharper logo, more ads, better SEO, or maybe just more content. And sometimes, sure, those things help. But what if the real problem isn’t the tactic? 

What if the real problem is that the business owner can’t clearly explain what they do, who they help, why it matters, and why anyone should care?

That’s where today’s guest comes in.

Lisa is the founder of Rebel Girl Marketing, a revenue clarity s...

Entrepreneurs are naturally optimistic. We start businesses because we see opportunity. 
We see what something could become. We move fast, make decisions quickly, shake hands, trust people, and often assume that if everyone has good intentions, everything will work out.

And sometimes it does... Until it doesn’t.

The partnership that started with excitement becomes a dispute. 

The contract you barely read becomes a problem. 

The agreement you never put in writing becomes a memory contest. 

The business name you loved turns out to belong to someone else. 

The...

A lot of entrepreneurs think the scariest number in business is zero. Zero sales. Zero customers. Zero cash in the bank. But sometimes, the scarier number is much bigger. It’s the big revenue number that makes the business look healthy, while cash flow is quietly breaking underneath. 

It’s the impressive sales number that hides shrinking margins. It’s the tax bill nobody planned for. 
It’s the profit that looked good on paper but somehow never made it into the bank account.

That’s where a lot of business owners get blindsided. They’re working harde...

In Episode 4 of Lessons From a Reluctant Entrepreneur, Mike Konrad shares the awkward, funny, and very real story of what happened after launching his company. He had the logo, the business cards, the office supplies, the used desk, and the company name.

What he didn’t have was a finished product, a brochure, specifications, photos, pricing, or anything resembling a polished sales presentation.

So naturally, he got on an airplane to meet his first prospective customer.

This episode explores one of the most important lessons of entrepreneurship: starting a business doesn’t mean you’re rea...

Some businesses sell a product. Some businesses sell a service. But hospitality sells something harder to define.

It sells a feeling. It sells the way a room looks when someone walks in. The way a guest is greeted. The way an event flows without anyone noticing all the work happening behind the scenes.
And that raises a really interesting entrepreneurial question: how do you scale something that is so personal?

My guest today is Nikita Khandheria, Founder and CEO of ERIA (long e) Hospitality. 

Nikita started her entrepreneurial journey at a very young a...

In Episode 4 of Lessons From a Reluctant Entrepreneur, Mike Konrad shares the awkward, funny, and very real story of what happened after launching his company. He had the logo, the business cards, the office supplies, the used desk, and the company name.

What he didn’t have was a finished product, a brochure, specifications, photos, pricing, or anything resembling a polished sales presentation.

So naturally, he got on an airplane to meet his first prospective customer.

This episode explores one of the most important lessons of entrepreneurship: starting a business doesn’t mean you’re rea...

One word can change the direction of a life.

In Episode 3 of Lessons From a Reluctant Entrepreneur, Mike Konrad shares the story behind the dismissive four-letter word that became the catalyst for starting his company. 

After designing a successful first-generation machine that helped solve an important environmental problem in the electronics industry, Mike believed the next step was obvious: a zero-discharge machine that eliminated wastewater discharge, reduced regulatory concerns for customers, and added valuable process data logging.

His boss didn’t agree.
The response was one word.
One syllable.
Four letters.

Entrepreneurs are often celebrated as risk-takers, but what if some of those risks don’t actually make sense?

In Episode 2 of Lessons From a Reluctant Entrepreneur, Mike Konrad looks back at the strange math of entrepreneurship, where founders can risk nearly everything for a return that may be far smaller than the danger they’re taking on.

Using the image of a Las Vegas roulette table, Mike explores how business owners often personally guarantee loans, leases, credit cards, vendor accounts, payroll, and sometimes even their homes, all in pursuit of a reward that may not justify the...

Have you ever looked at someone else’s success and thought, “I could do that,” only to immediately follow it with, “But not yet. I’m not ready. I don’t know enough. I need a better plan.”

That space between knowing you’re capable of more and actually taking the leap is where so many reluctant entrepreneurs live. It’s not always a lack of talent. 

It’s often perfectionism, fear, overthinking, or waiting for confidence to show up before taking action.
My guest today, Jennie Blackwood, understands that space well.

Jennie walked away from a de...

A lot of entrepreneurs dream about success. They dream about freedom, control, growth, income, and building something they can call their own. But very few dream about the part where the business fails. Very few dream about bankruptcy. Very few dream about rebuilding from the wreckage of a company they once believed would define their future.

My guest today has lived that story.

Max Emma is a Certified Franchise Executive, franchisor, franchise consultant, and co-founder of BooXkeeping. 

His journey began with immigrating to the United States from the former Soviet Union. From there, he b...

A lot of entrepreneurs leave corporate life because they’re chasing freedom. Some are chasing money. Some are chasing control. But for many entrepreneurs, the real story is more complicated. They leave because something inside them says, “There has to be another way to work, lead, build, and live.”

Today’s guest, Justin Ricklefs, knows that tension well. 

Justin spent years in the front office of the Kansas City Chiefs, building relationships, partnerships, and revenue inside one of the most recognized sports organizations in the country. 
But eventually, he stepped away from that familiar world and took h...

Most business owners dream of growth. But growth can become a trap. More locations, more employees, more customers, more complexity. 

Before long, the business that was supposed to create freedom can start consuming every available hour. So the real question is not just, “How do I grow?” It is, “How do I grow without building a business that depends entirely on me?”

My guest today is Dr. Tom DuFore, founder and CEO of Big Sky Franchise Team. 
Tom has spent more than two decades helping business owners think beyond the single-location, owner-dependent model and explore whether fra...

I’m launching a new series from The Reluctant Entrepreneur Podcast called Lessons From a Reluctant Entrepreneur.

This series is based on stories and lessons from my book, The Reluctant Entrepreneur: Anatomy of a Business Startup, From Uncertainty to Unstoppable.

Episode 1 is titled The Myth of Being Your Own Boss.

People often say, “It must be great being your own boss.” And I get it. From the outside, entrepreneurship can look like freedom. No boss. No time clock. No one approving your vacation. No one telling you what to do. But once you start a busin...

Some entrepreneurs build one business and stay in that lane forever. My Guest today is not one of those entrepreneurs.

His journey started on the tennis court, eventually led to building a tennis business in Beverly Hills, and later moved through real estate, franchise ownership, recruiting technology, and now coaching coaches.

Along the way, he built businesses, led teams, helped support hundreds of real estate agents, created tools that impacted recruiting across North America, and learned that entrepreneurship is rarely a straight line.

It’s a series of transitions. Some planned. Some unexpected. Some exc...

What happens when you finally build the business you dreamed of, grow it, sell it, and then discover that freedom doesn’t feel quite the way you expected?

My guest today is Alane Boyd. She’s a serial entrepreneur, growth strategist, keynote speaker, AI and automation expert, and co-founder and CEO of Biggest Goal. 

She’s built and led multiple SaaS companies, grown a tech company into an 8-figure business, and successfully exited two companies. On paper, that sounds like the entrepreneurial dream. But as we’ll talk about today, the dream has a second side. 

What do you do when life gives you every reason to stop, but something inside you refuses to quit?

My guest today is Jay Setchell, a Marine Corps veteran, serial entrepreneur, inventor, author, and the voice behind Never Quit Trying. Jay’s life story is not theoretical inspiration. It is lived experience.
He grew up on a working farm, served in the Marine Corps, survived multiple near-death experiences, and has endured more than seventy surgeries. 

His book, The Strength Within You: It’s Always Too Soon to Quit, explores the power of mindset, preparation, faith, resil...