Life, Values & Legacy: Our Chat with Ben Kalkman of Gilbert

Ben Kalkman shared their story and experiences with us recently and you can find our conversation below.

Ben, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What makes you lose track of time—and find yourself again?
Honestly? Playing with AI tools and figuring out how they can actually solve real problems for real people.

I’ll sit down at my computer thinking I’m just going to “quickly test something,” and suddenly my wife is asking why I missed dinner. Again. (She’s learned to text me reminders now.)

Here’s the thing—I wouldn’t call myself an AI expert, not by a long shot. But I know enough to be dangerous, and I’m having way too much fun learning. It’s like getting a new toolbox where every tool can do ten different jobs, and you keep discovering what’s possible.

What really gets me going is when I can take something that’s been a pain point for a business—like spending hours on tasks that could be automated—and show them how to fix it. That moment when someone realizes they can get three hours of their life back every day? That’s when I remember why I love this stuff.

I’m actually starting another company around AI consulting because, frankly, there are too many people out there making this technology sound more complicated than it needs to be. Sometimes the best solution is the simplest one, and I get a kick out of helping people cut through the noise.

The “finding myself again” part happens when I look up from the screen and realize I’ve been completely absorbed in solving a puzzle that actually matters. That’s my sweet spot—when the work doesn’t feel like work.

Can you briefly introduce yourself and share what makes you or your brand unique?
Well, I’m Ben Kalkman—husband, father of nine kids (yes, nine), and serial entrepreneur who’s been building businesses for over two decades. If you’re wondering how someone manages nine kids and multiple companies, the answer is: very carefully, and with an amazing wife who’s definitely the smart one in the family.

I’m the founder of Rocket Media, which started as a web design company back when websites looked like they were built in someone’s garage (because most of them were). Over the years, we’ve evolved into a full-service marketing agency helping businesses actually connect with their customers instead of just throwing marketing spaghetti at the wall and hoping something sticks.

I also own Modern Moments, a wedding and event venue, which taught me a whole lot about the importance of getting details right when people’s big moments are on the line. Nothing like a stressed bride to keep you focused on excellence. And I host a podcast called Guiding Growth, where I get to talk with other business owners about what actually works—and what definitely doesn’t.

I’m also in the process of launching an AI consulting company because, frankly, there’s too much fear and confusion around AI right now. Small businesses think they need to hire a team of data scientists to benefit from these tools, which is like thinking you need to be a mechanic to drive a car. My job is helping people cut through the noise and find the simple solutions that actually move the needle.

Whether it’s marketing, hosting events, sharing insights on the podcast, or helping businesses navigate AI, my approach is pretty much the same across everything I do: treat people well, tell the truth (even when it’s uncomfortable), and focus on solving real problems. No corporate speak, no fancy charts that don’t mean anything, just straight talk about what’s working and what isn’t.

I’ve made plenty of mistakes over the years—enough to write a book—but I’ve learned that people appreciate honesty and competence over flashy presentations and empty promises. At the end of the day, it all comes down to helping people succeed. That’s what gets me up in the morning.

Great, so let’s dive into your journey a bit more. Who taught you the most about work?
Three people shaped everything I know about work, and they couldn’t have been more different.

First, my parents. Dad was an art teacher and wrestling coach—picture someone who could teach you to paint a landscape in the morning and then pin you to a mat in the afternoon. Mom taught English and somehow managed to keep our household running like clockwork. They both worked in public schools, which means they dealt with impossible budgets, difficult kids, and parents who thought they knew better. But they never complained. They just showed up every day and did the work because it mattered.

What they taught me wasn’t complicated: show up, work hard, treat people right, and don’t make excuses. Pretty basic stuff, but you’d be amazed how many people can’t nail those four things.

Then there was Gary Alexander, my first boss out of college. Gary was this veteran entrepreneur who’d had a successful corporate career, retired, and then decided to start a computer networking company with his four sons. When I joined as Marketing Manager, he basically adopted me as son number five.

Gary taught me how business actually works—not the textbook version, but the real version. How to read people, how to solve problems before they become disasters, how to make decisions when you don’t have perfect information. I still use strategies he showed me twenty years ago.

The funny thing is, both my parents and Gary taught me the same lesson in different ways: good work isn’t about being the smartest person in the room. It’s about caring enough to do the job right and sticking with it when things get tough.

What fear has held you back the most in your life?
Self-doubt. Which is probably not what you’d expect if you know me.

Look, I’ve got what people call a “high-D” personality—I’m the guy who walks into a room, takes charge, and gets straight to the point. Most people see confidence. But for the longest time, that was basically performance art.

Inside, I was constantly thinking everyone else had it figured out and I was just faking my way through. Classic imposter syndrome, right? I’d be in meetings thinking, “When are they going to realize I don’t actually know what I’m talking about?” It was exhausting.

The crazy part is, this fear of being “found out” kept me from being who I actually was. I’d hold back ideas, second-guess decisions, and play it safe because I was terrified someone would discover I wasn’t as smart or capable as they thought.
Here’s what I finally realized: everybody’s making it up as they go along. The difference between successful people and everyone else isn’t that they have all the answers—it’s that they’re willing to figure it out along the way and not let the fear of being wrong paralyze them.

Once I gave myself permission to just be me—mistakes, learning curves, and all—everything changed. It’s like I’d been driving with the parking brake on for years and finally let it go. The confidence became real instead of performed, and suddenly, the right opportunities and people started showing up.

Turns out, people can sense authentic confidence from a mile away. And they’re attracted to it, not because you’re perfect, but because you’re genuinely comfortable with who you are.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What’s a cultural value you protect at all costs?
Family. And I mean that in every sense of the word.

Obviously, with nine kids and an amazing wife, my actual family comes first—no meeting is more important than my daughter’s soccer game, and no deadline is worth missing dinner with everyone. But here’s where it gets interesting: I genuinely believe you can create a family culture at work too.

I know, I know—everybody says “don’t call your employees family, it’s just business.” And sure, if you’re using “family” as an excuse to underpay people or guilt them into working weekends, then yeah, that’s garbage.

But if your intentions are real? If you actually care about the people who work with you, celebrate their wins, support them through tough times, and treat everyone with respect—even the ones who drive you a little crazy—then you can absolutely build something that feels like family.

Think about it: we spend more waking hours with our work people than we do with our actual family, some weeks. Why wouldn’t we want those relationships to be meaningful?

Here’s my test: Would I invite this person to my kid’s birthday party? Not because I have to, but because I genuinely like them and want them there. If the answer is no, then we’ve got work to do on that relationship.

At the end of the day, whether it’s my nine kids around the dinner table or my team around the conference table, I want people to feel valued, heard, and cared for. That’s non-negotiable for me.

Life’s too short to spend it with people who don’t have your back.

Okay, so before we go, let’s tackle one more area. What do you understand deeply that most people don’t?
Two things, and I’ll be honest—they’re both deeply personal, so take them for what they’re worth.

First, that faith matters more than we want to admit. I’m not talking about religion or going to church every Sunday, though that’s part of it for me. I’m talking about believing there’s something bigger than yourself, something that gives your life meaning beyond just getting through the day.

I’ve watched people chase success, money, recognition—all good things—but never find peace because they’re missing that foundation. My faith in Jesus Christ anchors everything I do, even when I mess up, which happens more than I’d like to admit. It’s not about being perfect; it’s about knowing you’re loved regardless.

Second, your real legacy isn’t your business or your bank account—it’s the people you leave behind who carry a piece of you forward. For me, that’s my nine kids and my wife. But I’ve seen this with mentors who shaped young entrepreneurs, teachers who changed students’ lives, even folks who never had kids but poured themselves into nieces, nephews, or kids in their community.

The question isn’t whether you have children—it’s whether you’ve invested in people who will be better because they knew you. That’s what lasts. Everything else is just stuff that gets sold at estate sales.

I know these aren’t popular truths in our culture, but they’re what I’ve learned matter most when everything else falls away.

Contact Info:

• Website: https://rocketmedia.com & https://modernmoments.com
• Linkedin: https://www.linkedin.com/in/kalkman/