---
title: "Say Yes, Then Figure It Out: The Entrepreneur’s Instinct"
description: Five entrepreneurs share how unexpected opportunities, customer needs, and uncertain decisions shaped their businesses on The Breakout Moment.
---

[Episodes | The Breakout Moment Podcast](https://www.thebreakoutmoment.com/episodes)

# [Say Yes, Then Figure It Out: The Entrepreneur’s Instinct](https://www.thebreakoutmoment.com/episodes/say-yes-then-figure-it-out-the-entrepreneurs-instinct)

 Written by [The Breakout Moment Podcast](https://www.thebreakoutmoment.com/episodes/author/the-breakout-moment-podcast) | Sep 29, 2026, 10:00:00 AM

 

 

The biggest opportunities in business don't always come with a plan.

In this special compilation episode, Christina May revisits conversations with Tony Checchia, Mason Hale, Lacey Snyder, Brendan McCluskey, and Nick Molfino about the unexpected moments that shaped their entrepreneurial journeys.

They share stories of finding a career they never planned for, turning a personal problem into a business, saying yes to a customer's unexpected request, starting a company without having all the resources in place, and building a business in just 32 days. From recognizing an opportunity hiding in plain sight to making a decision without knowing exactly how things will work out, these conversations reveal a common lesson: success isn't always about following the plan. It's about staying open to opportunity, trusting what you know, and being willing to take the next step.

### **COLD OPEN**

**Tony Checchia:** I just feel blessed that I've found something by accident. That was not my game plan.

**Mason Hale:** It found me.

**Lacey Snyder:** We were like, okay, whatever you need, we'll figure it out.

**Brendan McCluskey:** I knew how much money I needed. I didn't have it. I started it anyway.

**Nick Molfino:** Luck, serendipity, you know, higher power, whatever your belief system is, there's a path and opportunity out there, and you really just got to keep your eyes open and make some good decisions.

**Christina May:** And just make a decision.

### **CHAPTER 1: THE PLAN ISN'T SACRED**

Welcome to The Breakout Moment.

Success stories have a way of looking obvious in hindsight: the right idea, the right timing, a lucky break.

But for most, entrepreneurship doesn't start with a perfect plan. What they do have is a willingness to pay attention when the path in front of them starts pointing somewhere unexpected.

Sometimes the instinct is simply to notice what's in front of you, make the call, and move before you know exactly how it ends. That's how Tony C found a career that was never part of the plan.

#### **TBM #14 | Unplug, Recharge Reset: Lessons on Growth with Tony Checchia**

**Tony Checchia:** I just feel blessed that I've found something by accident. That was not my game plan. Coming out of college, I was going to go to law school. I don't know if you know this story or not. I think I've told you the story. And then I got my real estate license as a backup plan. Sister Doctor Mary Nussbaum, my economics professor slash advisor, says to me, "Don't be so hard on yourself. You can go to law school. Maybe someday this real estate thing might work. You might be the owner of your company someday." I'm like, prophetic, right?

**CM:** There it is.

**TC:** Yeah, and here I am, you know, almost 40 years later and still doing it. I love it.

**CM:** I do too. I absolutely love it. I think it's interesting. I don't know about you, but for you, that was the backup plan. For me, I was just in denial for too long. I kept having friction in my jobs because I wanted to go off script. I wanted to go do this, or I wanted to go chase that. I mean, everyone at Illumine8 knows, I always tell people, I like to run into burning buildings, and in corporate, they don't like you to run into burning buildings usually, unless you're a firefighter. Obviously, I wouldn't make the cut. I was just in denial for so long. Then I finally, just out of necessity after being told no so many times, "No, you can't have that," and I was like, "Screw you."

**TC:** Mine was about two years of denial. Coming out of college, my parents had invested in me to get a college degree and aspirations to go to law school, and I got a real estate license as a backup plan just so I'd have something to do after graduating. Started working in real estate, but felt that I had settled. I was like, why did I go to college just to be a realtor? This was such a waste-kind-of-attitude, really arrogant, young and arrogant, and thought way more of myself than I probably should have at that time.

I had a transaction that involved working with a local real estate attorney and experienced firsthand what that attorney brought to it. The friction, the tension, and his whole disposition were very one-sided. He was representing the buyer, and he was advocating only for the buyer. As brokers, we're bringing parties together. We're solving problems. We're resolving issues, and we're making the transaction come together. He just kept fighting me the whole time.

I had that moment where I was like, "That's not my DNA." What the hell was I thinking, going to law school like that? If that's what lawyers do, that's the last thing on earth I want to do.

So it took a while. Then I had the fortunate opportunity of a seasoned broker agent who had been in the business for a while, got in a car accident, was recovering from his injury, invited me to work on a group of investment properties that he was listing as a portfolio at one time, and he was like, "Do you want to help?"

I'm like, "Yeah, sure. What do you want me to do, wash your car? Change your oil? What do you want?" He's like, "No, no. Work with me on these listings."

And so my experience level and my interaction with higher-level transactions just jumped, and I was able to work with somebody who, as a mentor, mentored me, who gave me that kickstart and accelerated my on-ramp to really get into real estate. That's when I really started to say, "Hey, I'm actually really good at this, and I love what I'm doing, and wow, now I'm getting paid."

I get to settlement, everybody's happy, and I get paid. I'm like, win, win, win, win.

**CM:** Right, right.

**TC:** Things kind of really started to fall in line.

### **CHAPTER 2: WHEN THE IDEA FINDS YOU**

Mason Hale wasn't searching when his business idea showed up right in front of him.

It was dropped in his lap as a problem. He solved it for himself, and simply paid attention when other people wanted the solution too. He acknowledged the opportunity and realized there might be something there that was bigger than he could have ever planned for.

#### **TBM #19 | How a Volunteer Became a Global Business Owner with Mason Hale**

**CM:** That's amazing. You didn't start with SwimTopia?

**Mason Hale:** No, no. So I started with the problem. I was working at a consulting company at the time, traveling about 50% of the time, most of it international. And while I was gone on a business trip, I got home and my wife said, "Hey, honey, I've got good news and bad news. Good news, the kids are signed up for the swim team. Bad news, I volunteered you to run the computers for the team."

And I was like, "What does that mean?" And so then she gave me the number of the current computer person on the team, and I went to her house, and she could not hand me this old, dilapidated team laptop fast enough.

So, you know, the way that swim teams run is surprisingly archaic. That software predated Windows. It started as a DOS program.

**CM:** Oh, my gosh.

**MH:** Almost every swim team runs on, or used to run on, it, and it just wasn't going to work with my travel schedule and things like that. So I quickly put up a site where the parents could tell me if they're going to be at the meet and what events their kids wanted to swim. And by the way, our team had 250 kids, so it was a lot to keep track of.

**CM:** Oh, my, that's a lot. No wonder she wanted to chuck this thing at you as fast as humanly possible. That's always a sign, you notice, like when you get volunteered for something and you're doing the handoff, whether it's a board or a volunteer organization or whatnot. You can always tell. You're like, "Oh, what did I get myself into here?"

**MH:** And the cost of making a mistake was really high because, you know, there's only so many lanes in a swimming pool.

**CM:** Right.

**MH:** And so if I forgot to enter someone in the event, there might not be a lane for them. And so, you know, you have a little girl that shows up and wants to swim the breaststroke, and if she's not in, you've got a crying kid and angry parents, and nobody wants that.

**CM:** Nobody wants that.

**MH:** Yeah, so I really had a problem, and I was able to fix it for myself. And then by summer 2010, by that time I was the computer chair for the whole swim league. We're in Austin, Texas, we're at the University of Texas Natatorium, and I get surrounded by the other teams in the league asking how much it would cost to use this thing that they knew that I had.

And it was at that point that I was like, "I might have to start a business."

**CM:** I might have something on my hands. And you know what? A lot of people talk about that type of genesis of an idea, and it's so funny. So many entrepreneurs, I feel, hunt for that idea. But in your case...

**MH:** It found me.

**CM:** It found you. And I think that's the case more often than not.

**MH:** Right.

### **CHAPTER 3: SAY YES, THEN FIGURE IT OUT**

Recognizing an opportunity is only the first step. You still have to decide what you're going to do with it.

For some entrepreneurs, that means being willing to say yes even before you know exactly how you're going to do it.

When one of Lacey Snyder's customers needed something her company had never offered before, the answer wasn't, "That's not what we do." It was, "We can probably figure that out."

#### **TBM #8 | The Power of Adjacent Markets with Lacey Snyder**

**Lacey Snyder:** We started in the lending space, residential to commercial, added fleet, maritime, aviation eventually. But our big breakout, our big thing we never saw coming, was when a client needed a structural steel building, couldn't find it, couldn't find where to get it from.

And we were like, "Okay, whatever you need, we'll figure it out." And then we were having some issues finding it.

**CM:** Oh, wow.

**LS:** So what we ended up doing was doing the research, finding somewhere where we could wholesale from. There's plenty of dealers, but there's no wholesalers. We basically created a partnership, and now we can provide those buildings.

**CM:** Wow. And, you know, that inspiration came from a customer. A customer need.

**LS:** Absolutely. A customer. Absolutely. As does everything.

I think that with every good business, you have to be open-minded. So if you hear something and you're like, "Wait a minute. I think I can do that. I can fill that need. I can figure that out," adding it certainly doesn't hurt.

And then by happenstance, we started a structural steel arm. And right now this is kind of top secret. This is an exclusive.

**CM:** Oh, look at you.

**LS:** Breaking news. We are going into the metal roofing business because someone needed a metal roof and we can wholesale that. And so now we have started adding that to our portfolio.

**CM:** Portfolio of work.

### **CHAPTER 4: GO BEFORE YOU'RE READY**

Of course, saying yes gets harder when the opportunity comes with real risk.

There is usually a point where more planning won't give you certainty. You either make the move or you don't.

Brendan McCluskey knew exactly what the business plan said he needed before starting his company. He didn't have it... but he saw the opportunity and started anyway.

#### **TBM #12 | Leadership Lessons from the Housing Crisis with Brendan McCluskey**

**Brendan McCluskey:** Every time I felt as if I had a plan laid out and I saw things kind of going the way that they want, I felt as if my entire world was like a snow globe and just got shook up. I was very much humbled, and I feel as if everything that I'm working on right now is literally the consequence of my journey from '08, '09. I was a young man, late 20s, just living very, very well.

**CM:** Living the dream.

**BM:** Yeah.

**CM:** Weren't we all?

**BM:** I was living rent-free in a ski-in, ski-out chalet in Aspen, Colorado, with three other knuckleheads. It was like a year-and-a-half-long bachelor party to myself. It was crazy. I was getting paid very, very well. But then the music stopped real hard. And, you know, I felt as if, especially in commercial construction, unemployment was every bit of 65, 75 percent. I mean, I didn't really know too many people that had jobs.

I was somewhat humbled. I went back to business school. When you're in business school, you're thinking about becoming an entrepreneur. That's what you do when you're in business school. So I was getting my MBA. I was messing with the energy markets. I learned about that. Then I eventually migrated back into the construction industry, started doing high-end work again, saw an opportunity to go out on my own, and again was just thoroughly humbled.

I thought I had it all figured out. I was ready to go. I'm a year and a half into this thing, and I'm like negative $300,000 in equity. I went out and just got crushed. I quit my job on April Fool's Day 2015.

**CM:** April Fool's Day?

**BM:** Yeah. Oh, yeah.

**CM:** Oh my gosh. I love that.

**BM:** I quit my job on April Fool's Day, pretty much. But what was sad in Baltimore was my first day of working was literally the week that led up to Freddie Gray. I had been tracking about $6 million of potential backlog, thinking that if I win a third of this, I'll be coasted for the first year of a startup, right?

**CM:** Right.

**BM:** But I started this company undercapitalized knowingly. I wrote a business plan. I knew how much money I needed. I didn't have it. I started it anyway.

**CM:** What else are you going to do?

**BM:** Exactly. And so, in the wake of Freddie Gray, all that work disappeared. All the investors from Philadelphia and DC were like, "We can make enough money in our own markets. Baltimore, you have too many problems." So getting the company up and going was a real slog. I'm dealing with it now to a degree. I made bad decisions.

**CM:** We all do.

**BM:** Right. Yeah. We're all entrepreneurs. We're all trying to figure this out.

**CM:** You're hiring me for all the mistakes I've made that I now know not to make. That's what you're hiring me for.

**BM:** All this gray hair is what you're hiring me for, yeah.

Over the course of my career, working in Baltimore, there have been times where I felt as if I've been tapped on the shoulder and a problem has been addressed to me and is like, work on this. I've done this time and time again.

In fact, when my company was early, on the ropes, my wife and I hated the company. It felt like a disaster and everything else.

**CM:** And it'll ruin a relationship.

**BM:** Oh yeah. A lot of stress. I mean, it was not going to plan at all. But it was the first project that someone came up to me and was like, "Hey, there's this project called Fade Street Outreach."

And so I got tapped on the shoulder, and I was like, "All right, I'll take this on." And again, we were basically hardly making payroll. But this job presented itself, okay, and I had to use every bit of piracy and leverage and skill to get that project across the finish line.

And it made me reaffirm that, you know what? No, I'm good at this. I'm good at my job. I'm better than a lot of my competitors. Who the hell else would have pulled this off with the resources that we had? And I did it.

So it kind of reconstituted a belief. It's like, okay, this is something I've got to pay attention to. When these projects come across my path, I don't have the luxury to say no. It's like when the man lays a job at your feet. Do you get to say no? You don't get to say no.

**CM:** No, you don't. You're just going to keep tripping over it.

**BM:** It sucks to be Catholic, right?

**CM:** Yes.

**BM:** Right. It's like we're leaning in on this. So fast forward, I've done a bunch of these at this point.

**CM:** Yes, you have.

**BM:** Yeah. And I got tapped on again.

**BM:** I had just had a personal journey that allowed me to see it. People say, "Oh, this is a phenomenal idea, Brendan." I actually really feel as if I'm not the genesis. I'm just seeing, and I just lived the path that let me see all the pieces come together.

**CM:** That's exactly it. That's exactly it.

### **CHAPTER 5: WHAT LOOKS LIKE LUCK**

When these stories are told years later, it's easy to call them luck. The right client appeared. The timing worked out. The right people happened to be there.

But luck only becomes an opportunity if someone is willing to do something with it.

Nick Molfino had 32 days to turn a "what if" into a real company. His story gets at the instinct behind all of these moments: keep your eyes open, make the best decision you can with what you know, and move.

#### **TBM #17 | From Employee to Business Owner in 32 Days with Nick Molfino**

**Nick Molfino:** I mean, I went from employed for almost 12 years to unemployed and a business owner in 32 days because Inova was willing to give us work.

**NM:** Fast forward to 2015. There's a second generation of owners at Twin who had run the company for about 10 years. Things didn't work out, we'll leave it at that. They went bankrupt. Inova reached out to me and said, "Hey, wherever you land, keep your team and we'll give you all this work."

And so I went from about to be unemployed, had just built a house a year before, my wife's been home with the kids, not really sure how we're going to make ends meet, to going, you know, I don't want to go work for somebody else. I don't want to start over and do the climbing the chain.

**CM:** Right.

**NM:** I had tons of respect for the DPRs and the HITTs and the Clarkes. I mean, they're amazing outfits, but they're not me.

**CM:** Right.

**NM:** And going to an organization that size as the new guy fighting for client share, I just knew that wasn't it. And when Inova approached me, Mark, again, huge person I want to shout out to. There's a logic. I'm going to tie this all back together. All these people that I owe a debt of gratitude to.

Mark, who used to run IDC, brilliant man. We had operating rooms under construction. I don't know how much money those rooms produce in revenue, but he knew Twin was not bonded. They would have had months long and who knows how much cost in getting another GC involved to scrub the job, figure out what's going on, re-contract it and start it up.

He knew that we had the right team because I'd been doing work for them for years, and basically he said, "Hey, wherever you land, take the work with you," with the intention being that we would land at another GC and the job would keep going.

Crazy idea. Sitting on the tailgate of my pickup truck on my driveway with my now-retired partner, who was also my neighbor. So we're sitting on the tailgate drinking beers, and I was like, "You know, neither of us wants to start over. Neither of us wants to go anywhere. What if?"

**CM:** Okay.

**NM:** And the what if became, we need money. Went out and did a quick cap raise, brought in a couple outside shareholders, family, friends.

But literally, conversation happened, went to Inova and said, "What if?" And they said, "You have 32 days. Make a decision. If in 32 days you're not somewhere that can be assigned this contract, we don't have a conversation."

In 32 days, we secured Class A licenses, all of the special BLD designations, everything we needed, had a banking program, had a line of credit, had a surety.

**CM:** It's amazing.

**NM:** I tell everybody, luck, serendipity, you know, higher power, whatever your belief system is, there's a path and opportunity out there, and you really just got to keep your eyes open and make some good decisions.

**CM:** And just make a decision.

**NM:** Make the best decision with the information you have at the time and realize that, you know, if it doesn't work out, you're still moving forward.

### **OUTRO: MOVE WHEN IT SHOWS UP**

None of these entrepreneurs knew exactly where the opportunity would take them when they said yes.

They noticed something worth pursuing, trusted what they knew, accepted what they didn't know yet, and moved anyway.

Success can look a lot like luck from the outside. But sometimes it is simply being able to recognize the opportunity when it shows up, and having the nerve to do something about it.

[View full post](https://www.thebreakoutmoment.com/episodes/say-yes-then-figure-it-out-the-entrepreneurs-instinct)

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