Trevor Merriden

You Don't Have to Be a Swashbuckling Extrovert to Build a Successful Business (Thank God)

December 26, 202510 min read

You Don't Have to Be a Swashbuckling Extrovert to Build a Successful Business (Thank God)

The entrepreneurial confidence crisis is real, and it's killing great ideas before they even start.

I sat down with Trevor Merriden—executive coach, podcast host, and someone who's spent decades helping entrepreneurs find their confidence and voice—and he absolutely shattered the myth that's keeping talented people from even trying to build businesses:

"A lot of people don't even start because they think they are not the entrepreneurial type of person."

You know that image in your head? The bold, adventurous, extroverted entrepreneur hacking their way through the jungle, doors flying open everywhere they go, never doubting themselves for a second?

That's bullshit. And it's costing you everything.

Trevor put it perfectly: "Everybody has it in them to be an entrepreneurial person. Whether they are introverts, extroverts, ideas people, process people—there are different ways to make money."

But you'll never find your way if you're too busy comparing yourself to some caricature of what you think an entrepreneur should be.

The Manual That Doesn't Exist (And Why That's Both Good and Terrible)

Here's what nobody tells you when you start a business:

There is no manual.

Trevor calls this both a blessing and a curse. The good part? You learn as you go. The best entrepreneurs figure shit out in real-time, adapt, and keep moving.

The bad part? The doors that don't just close but get slammed in your face can make you question everything:

"Maybe I don't have what it takes."

"Maybe I'm not cut out for this."

"Maybe I should just go back to my corporate job where at least I know what I'm doing."

And here's the kicker—these doubts are often premature. You're bailing before you've even given yourself a real chance to figure it out.

This is why so many brilliant ideas die in the "I'm not confident enough" graveyard. Not because the ideas were bad. Not because the founder wasn't capable. But because they bought into the myth that entrepreneurship is for a certain "type" of person, and when they hit their first real obstacle, they assumed that meant they weren't that type.

The 90% You Didn't Know You'd Need to Know

Here's the thing that breaks most first-time entrepreneurs:

You start because you're good at ONE thing. You've got the tech. The science. The product idea. The skill. Whatever it is—that's your 10%.

Then you realize that running a business requires you to be competent at all the other shit you have zero interest in or training for.

Marketing. Sales. Finance. Operations. HR. Legal. Customer service. Supply chain. The list is endless.

And suddenly you're drowning in the realization that being brilliant at your core thing means absolutely nothing if you can't figure out how to sell it, deliver it, price it, and keep the lights on while doing it.

This skill gap is daunting as hell. And it destroys confidence faster than anything else.

But here's what Trevor gets that most people miss: Realizing you have skill gaps isn't a weakness. It's information.

The entrepreneurs who succeed aren't the ones who can do everything themselves. They're the ones who recognize what they're not good at and hire people who are better than them at those things.

Hiring Better Than Yourself Is a Confidence Hack

Trevor dropped this framework that completely reframes how you should think about building a team:

"You hire somebody that's better than yourself. That doesn't just mean you're providing somebody with an income. It means you're helping yourself in terms of finding confidence, because then that liberates you from the things that you're perhaps not so good at."

Read that again.

Hiring isn't a cost burden when you hire the right person. It's a liberation.

It frees you to focus on your strengths. It removes the crushing weight of trying to be everything to everyone. It gives you the breathing room to actually build the business instead of constantly putting out fires in areas where you're incompetent.

This is especially critical for scaling client success teams and building sustainable business expansion strategies. You cannot do it alone. You shouldn't try.

The introverted engineer who's brilliant at their tech but terrible at sales? They don't need to become an extroverted salesperson. They need to hire someone who's great at sales and let them do their thing.

The visionary founder who has a million ideas but can't execute for shit? They don't need to force themselves to become process-oriented. They need to hire someone who loves systems and operations.

Stop trying to be someone you're not. Start building a team that complements who you actually are.

The Leadership Crisis Nobody's Talking About

Trevor broke down two massive challenges in leadership right now:

1. The command-and-control leader is dead (but some people haven't gotten the memo)

The old model—where the boss at the top makes all the decisions and everyone else just executes—doesn't work anymore. The pandemic killed it. AI is burying it.

Why? Because business moves too fast for hierarchical approval chains.

By the time your request goes up three levels, gets reviewed, comes back down with feedback, gets revised, and goes back up for final approval—the opportunity is gone. The market has shifted. Your competitor already launched.

You need empowered teams who can make decisions in real-time. You need autonomous workers who understand the vision and can execute without waiting for permission from five layers of management.

This requires a completely different leadership style. One based on trust, clarity, and communication rather than control.

2. AI is forcing leaders to be more human, not less

Here's the paradox: AI is a triumph of human curiosity. We built this incredibly intelligent tool that can help us work faster, think bigger, and solve harder problems.

But Trevor's concern (and it's a valid one) is this: "Will it tempt us to outsource part of our critical reasoning and problem-solving?"

Will leaders become lazy? Will they stop asking hard questions because AI can just give them an answer? Will they lose their curiosity?

Or will they use AI to free up brain space so they can be more human, more curious, and more connected than ever before?

Trevor's challenge is simple: "How can we use AI to become more and not less curious? Use AI as a chance to ask more questions."

This is the inflection point we're at right now. You have a choice:

Option A: Use AI as a crutch. Outsource your thinking. Stop being curious. Let the machine tell you what to do.

Option B: Use AI to automate the busywork that's been clogging your brain. Free yourself to ask better questions, build stronger relationships, and lead with more humanity than you've ever had time for before.

One of these paths leads to competitive advantage and relationship-driven revenue growth. The other leads to obsolescence.

Choose wisely.

Your Leadership Style Doesn't Need to Look Like Anyone Else's

Trevor works with a lot of fledgling leaders who are trying to figure out what "leadership" is supposed to look like.

And here's what he tells them: "There isn't a manual and whichever way works, works. But it's got to be true to you and the way you lead."

Stop trying to imitate what you think leadership means.

Stop copying the style of the CEO you admire who's nothing like you.

Stop forcing yourself into a mold that doesn't fit because you think that's what "professional leadership" requires.

Just like there isn't one "type" of successful entrepreneur, there isn't one style of effective leadership.

The introvert who leads through thoughtful questions and deep listening? That works.

The extrovert who energizes teams through enthusiasm and connection? That works too.

The process-driven leader who creates systems and structure? Absolutely.

The visionary who paints the big picture and inspires people to chase it? Hell yes.

What doesn't work is trying to be someone you're not.

Your team can smell inauthenticity from a mile away. They know when you're performing "leadership" instead of actually leading. And that disconnect destroys authentic client connections both internally with your team and externally with your customers.

The Question Economy Is Here (Are You Ready?)

Here's Trevor's optimistic take on the AI future, and I'm here for it:

"The more we use AI, the more the yearning for humanity and human connection will grow."

Think about it: When AI can give you instant answers, what becomes valuable?

Asking the right questions.

When AI can automate tasks, what matters?

The ability to think critically and creatively.

When AI can process data, what's irreplaceable?

Human judgment, empathy, and connection.

This is actually great news for leaders who are willing to lean into their humanity instead of trying to out-robot the robots.

The leaders who will thrive in the next decade aren't the ones with all the answers. They're the ones asking better questions:

  • What are we actually trying to accomplish here?

  • Who are we serving and what do they really need?

  • What assumptions are we making that might be wrong?

  • How do we balance efficiency with humanity?

  • What does success look like beyond the metrics?

These are questions AI can't answer for you. These require human connection, critical thinking, and the kind of curiosity that only comes from actually giving a shit about people.

The Confidence to Ask for Help

Let's bring this full circle:

The entrepreneurs and leaders who succeed aren't the ones who have it all figured out. They're not the swashbuckling extroverts with unshakeable confidence.

They're the ones who have the confidence to admit what they don't know and ask for help.

They hire people better than themselves.

They ask questions instead of pretending to have all the answers.

They build trusted advisor relationships with mentors, coaches, and peers who can help them navigate the things they've never done before.

They embrace their authentic style instead of trying to copy someone else's playbook.

And they use tools like AI to become more human, not less—to free up the mental bandwidth to actually connect, communicate, and lead effectively.

Watch the Damn Episode

This conversation with Trevor went deep into finding your authentic voice, building confidence through the right team, and why the human skills are becoming more valuable than ever in the age of AI.

If you're an entrepreneur questioning whether you have what it takes, or a leader trying to figure out how to lead authentically in a rapidly changing world—this episode is your reality check.

Watch the full episode here because Trevor's frameworks for building business relationships and leadership communication are the difference between faking it and making it.


P.S. If you're sitting on a business idea right now thinking "I'm not the entrepreneurial type," let me be very clear:

You're using that as an excuse to avoid trying.

Trevor's entire point is that there IS no "entrepreneurial type." Introverts build billion-dollar companies. Process people create innovative products. Quiet, methodical thinkers change industries.

The only way you're not the "entrepreneurial type" is if you're not willing to learn, adapt, and ask for help when you need it. And if that's the case, then yeah, maybe entrepreneurship isn't for you.

But if you're avoiding it because you think you need to be someone you're not? That's just fear dressed up as self-awareness.

P.P.S. That command-and-control leadership style some of you are clinging to? The one where you need to approve every decision and micromanage every detail?

It's not making you a strong leader. It's making you a bottleneck.

Your team is slower because of you. Your company is less agile because of you. Your best people are leaving because of you.

AI isn't going to save this leadership style. It's going to make it even more obviously obsolete.

The leaders who win are the ones who empower their teams, ask better questions, and have the confidence to admit they don't need to control everything.

Go watch the episode. Learn from Trevor. And for god's sake, stop pretending you need to be someone you're not to build something great.


Karl Pontau hosts The Human Connection Podcast, where we talk about the stuff that actually matters in business: the humans running it. Because whether you're B2B or B2C, it's really H2H—human to human. Subscribe so you don't miss the next episode where we probably say something that'll make your HR department uncomfortable.


#KarlTheBridge Find me on LinkedIn! I'm the host and creator of The Human Connection Podcast.

Karl Pontau

#KarlTheBridge Find me on LinkedIn! I'm the host and creator of The Human Connection Podcast.

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