Failing Forward: The Mistakes Behind the Breakout Moments

Some of the most important breakout moments start with something going wrong.

In this special compilation episode, Christina May revisits conversations with Buddy Henley, Mason Hale, Terry Egley, Brett Snyder, Jeff Schwartz, and Aaron Shapiro about failure, mistakes, and the lessons that come from both.

They share stories of plans that did not work, jobs lost, risks taken, mistakes owned, and the ways those experiences changed how they lead today. From learning what you can control to creating a culture where people feel safe admitting when something went wrong, these conversations reveal a common lesson: failure is not the opposite of progress. Sometimes, it is how you get there.

TBM #2 | AI. Cohorts, and Tipping Points: Our 2025 Breakout Moments

Christina May: Your breakout moment could be a mistake. Some of my best breakout moments have been failures.

Intro:

Welcome to The Breakout Moment. In this episode, we're doing things just a little differently. When we talk about breakout moments, we're usually focusing on what went right.

But after so many conversations with business owners and operators, something else has come up again and again. The mistakes, the wrong turns, the risks we took, and the moments we thought everything had fallen apart.

I know I've had a few of those.

So, sometimes the thing that changes your business isn't the win. It's what you learn when something goes wrong.

The Fear of Getting it Wrong

Buddy Henley's story starts with the fear of making mistakes. But sometimes the mistakes are inevitable. And the best learning comes from taking responsibility and moving forward.

TBM #15 | Mentorship, Mistakes, and Better Leaders with Buddy Henley

Christina May: We have just been chatting about all the mistakes that we have made and all the things that we have learned from those mistakes, and I kind of want to start there because, like many people who come on the show, we talk about lots of breakout moments.

It wasn't just one breakout moment, but I think the mistakes we make along the way are what lead to a lot of breakout moments. So I thought I would kind of kick you off with that and continue the conversation there.

Buddy Henley: Well, first of all, thank you for having me here, Christina. It's truly an honor to be here.

So yeah, we do make a lot of mistakes, and I've made a lot myself. As we were talking about earlier, one of the first mistakes—I was a young superintendent, very early in my career, and I was very concerned about making a mistake. I thought it'd end my career right there.

I had one job in particular, and the layout was complicated, trying to get this right. I was paired up with a seasoned superintendent at the job, and he was pushing me and said, “Why don't you go out there and do the footings of the media center?”

And I'm like, “Because I'm scared to make a mistake, Pete. I can't figure this out.”

And he is a German guy, very heavy German accent. He started chuckling and he says, “Just go out there and do it.”

And he said, “If you never screw anything up in life, you've never done anything.” But then he had a very serious face. He says, “But if you screw it up, you gotta be able to fix it.”

So I was like, “That's so true.” So I did go out there and do it, and that's really been my motto ever since.

If you don't take a risk in life, you're never going to get anywhere. You have to make mistakes—as long as they're not huge, right? But yeah, trial and error, and push things a little bit. That's really how you're going to move forward in life.

CM: I agree 100%. I feel like the big lessons I've learned didn't really necessarily come out of a book. It was more so, “Oh, I didn't quite do that right,” and I have to go back, retrace my steps, redo it.

I find when I do that, I learn so much more and consequently usually don't make the mistake again.

But how do you take that idea as a leader and make a space for people to feel safe within your company to make mistakes? Because I know that is something you felt as a young superintendent. Now that you have young superintendents and people that work for you, how do you reassure them that it's going to be okay if you make a mistake?

BH: So I really try to reinforce to them what the end product needs to look like. I said, “When we finish, it needs to look like this.” I said, “Here's how I would do it, but if you have another way, we can try it. If you have another idea, because I'm not the only one with good ideas.”

So they might come up with something and we try it. And I don't let them fail. I'll go around like, “Looks like you're having trouble,” or something, but really support them along the way because it gives them better job satisfaction, too, if they can take ownership in something and know that their way got us there.

And sometimes it does happen where they make a mistake. We had an incident probably 20 years ago where one of the young superintendents—I told him how to get there, and he totally deviated.

CM: See, we almost made a mistake.

BH: I almost did, absolutely. And we saved it.

So he deviated from what I told him, and then he called me that evening very upset. And he goes, “You know what? I screwed up royally.” He goes, “I didn't hit the mark that you said to hit. I'll bring back the truck. I'll turn my tools in.”

He thought he was fired.

I was like, “Did you learn anything from this?”

He goes, “Oh, absolutely.”

I said, “So you would never do that again, right?”

He goes, “No, I won't.”

And now he's one of our senior superintendents 20 years later, and he reinforces the same thing to the young people he's mentoring. So we really try to be supportive of it. It helps people develop.

We want to have people grow with us.

When the Plan Breaks

For Mason Hale, it should have been perfect, but it wasn't. So many of us believe there are the correct way to do things. When the right path failed, he had to rethink his entire approach.

And then there's Terry Egley. She knew that everything was figure-outable.

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

Mason Hale: I think the fundraising route also sort of masks success. People will celebrate raising big rounds, and that's not really success. And so it can actually put you on the wrong track.

There's a lot more options out there. I'd say the big lesson I've learned is that if you assume that you need a lot of money to go do things, sometimes you can find another way to achieve the same objective without cash or with other—

You have a lot more at your disposal as an entrepreneur than you maybe see at first.

So I was going through as a solo founder. Multiple people told me I was absolutely crazy for doing that, that trying to do this alone was really—

CM: Really interesting.

MH: So I found a co-founder. There's a whole story there that I won't get into, but it should've been perfect. But it wasn't.

And so we did raise a small angel round. That demo day that I mentioned, we actually won the Audience Choice Award. I have a nice plaque from that.

But a little more than a year later, the co-founder relationship wasn't working, and we burned through most of the money that we'd raised.

We only had three months to go, and I was faced with, like, “What do I do now?”

And at this point, we had customers. They loved what we were doing. We weren't making that much money. We didn't have employees at that point. We had some contractors, but I had to pull the plug on that, and I stretched that three months of runway for six years, up to 2017.

So I basically got back into side-project mode. I was doing other jobs, doing consulting gigs, not paying myself with SwimTopia.

CM: Man, that sounds familiar to me.

MH: Yep, yep. And those are the things that no one understands.

But by 2017, I did have a full-time employee and three part-time employees, but I still wasn't on the payroll.

And then I went to Atlanta, and there was another competing software out there that was ad-based. So it was a free product that was completely ad-supported, but was very popular in the Southeast.

And I talked to the founder of that early on when I was just starting to see, like, maybe we could work together. He wasn't really interested, but by March of 2017, I'd grown enough to where I had just passed him in terms of number of customers.

He was at the same league meeting that I was at, and so we went and grabbed a beer afterwards. And he told me that his kids had graduated and weren't doing swimming anymore, and he was looking for a way to hand off his customers in some way.

And at this point, I'm not even paying myself a salary, so I don't have money to go buy a company.

And so my first reaction was, “Yeah, cool story. But what am I going to do?”

CM: Yeah, nothing I can do with this.

MH: But I kept thinking about it, like, “Is there something we could do?”

So we were able to work out a structure where he vested stock options in my company based on the number of customers of his that converted to paying customers of mine.

And that's another risk for me, because we charged for our product and he didn't. So there was a risk of how many people would switch from a free product to a paid product. And we didn't know.

So that way, that structure, we shared that risk together. And it also motivated him to sort of be a salesperson for me, to encourage his existing customers to move over. And that almost doubled our customer base overnight.

CM: Wow.

MH: But he had about 200 customers that were using his product. And so this would give us a way to start with 200 customers instead of zero.

So, sort of a boost in two ways that helped us accelerate launching a new product and also increasing the customer base.

And I got to start paying myself a reasonable salary.

CM: That's amazing. So that was then. Fast-forward to now.

MH: Yeah. I mean, now we have 16 employees.

CM: Wow.

MH: And I'm paying myself a reasonable—more than a living salary.

And we have customers all over the country. Actually, we have customers in 20 countries.

CM: That's amazing.

MH: Customers all over the country. I'd love to go visit them. We have a full engineering team and things like that.

TBM #9 | Everything is Figure-Outable: Building a Construction Business with Terry Egley

CM: What do you remind yourself on days where it gets tough? Because we all have those.

I think those are the moments—we all talk about the end of it, right? Like, we're still here. We're still in business. We're employing people. We're, I hate to say, eye roll, living the dream. The dream some days will kill you.

Terry Egley: Yeah. Right, right.

CM: Well, what are some of the things that you work through? Usually it's those tough moments right before things really start to push through.

And even you mentioned, like, “I'm sitting on my porch swing at my new house with my brand-new mortgage. I don't have a job. I'm single, and I got two kids.”

TE: Right.

CM: Let's start a business. Let's go work somewhere else.

Yeah, it's that adversity that I feel like sometimes is that moment. What do you use to kind of get yourself through?

TE: I think what comes to mind, honestly, I have a sign behind my desk that says, “Everything is figure-outable.”

CM: I love that.

TE: And it is. It's true.

When things are slow, I'm like, “Oh gosh, which hat do I have to put on right now to ramp things back up? What is it that I have to do to make sure that the billings are coming in for this month? What do I have to do to make sure that this job runs smoothly?”

I think it's just everything is figure-outable. You can't give up. You just have to plug away and figure out how to pivot.

Prior to COVID, we did mostly office spaces.

CM: COVID changed that for you.

TE: It did change that. But fortunately, before that—and I would love to say this was my major brainstorm—I had somebody come to me and ask about doing a lab, and I'm like, “Yeah, we can do that.”

Little did I know what was entailed in a lab, but we figured it out. It wasn't the smoothest job. We made mistakes, but we owned our mistakes and we corrected them, which enabled us to continue doing work for the person.

We started getting into some restaurant builds, minor little ones, this and that. And had that not happened, and I guess been brave enough to take it on at that point in time, we wouldn't be in business today.

Office spaces, they're starting to come back, thank God, but—

CM: But everything has a cycle.

TE: It does have a cycle.

CM: Yeah.

TE: When they come back full force, we'll be ready for them because we've done them.

But in the meantime, we've got the other past experience under our belt. We love restaurants and retailers and small businesses. Anything that comes our way, we're willing to tackle it.

So I think that's definitely helped sustain us for the long run.

Control What You Can

Of course, not every setback comes from a bad decision. The market changes, a company closes, a job disappears. We've all experienced some of these things. There are things in business that you just simply can't control.

And our guest, Brett Snyder, has lived through this more than once. Eventually, experience with failure changes the question. It's no longer just, "How do I recover when something goes wrong?”, it becomes, "How do I lead when someone else gets something wrong?"

And for Brett and Jeff Schwartz, the answer to that question has become part of the company culture.

TBM #5 | No Big Bang: How Small Business Decisions Create Big Business Shifts With Brett Snyder

CM: Can you share a failure that you use maybe as an example, or maybe even whatever you're comfortable with—something recent that you share with your team?

Brett Snyder: Yeah. I think I say to my team—and it's funny, I had this conversation with someone the other day who was at risk of losing their job and that kind of thing.

And they said there's a certain amount of fear, fear of failure, and all that kind of stuff that goes with that.

And I said to him—and I've said to my team—“I've been at three companies that have closed their doors.”

Not because of what I've done, but the economy, the real estate crash—

CM: A lot of people lost it then.

BS: A lot of people have lost their jobs, including me, multiple times.

And I'm here, ten years being a partner in a company, ten years of owning a brewery. All those things.

I think the biggest one I use is, “Listen, this might not be here tomorrow, but only work on those things that you can control.”

I view the '08 economy as weather.

CM: Yeah.

BS: It might happen. There's nothing I should worry about because I can't control it. I can't change it.

We're going to get ice. We're going to get ice. I can't do anything about that.

You couldn't do anything about those things. Work on what you can control.

Because at any moment, you might lose your job. And I tell them all the time, that's why you need to have a network of people.

CM: Right.

BS: Because who are you going to call? Who is your counsel? Who do you know? Who are you going to when that call happens that we're shutting down operations?

CM: Where are you going to pick up the phone?

BS: Where are you picking up the phone? So have that list. Have the people around. Know who they are and be able to call.

Because they're not going to judge you. That group, they're not judging you because of the weather.

CM: No, absolutely not.

BS: And I'm a big believer that you fail forward. We talk about it a lot.

You have to get your people—you can't be the person who holds it up. I'd rather have you make a bad decision that we could talk about—

CM: Than wait on me.

BS: Than you wait. If you're waiting, in real estate and construction, you're losing. You're losing, you're falling behind.

CM: That's almost, I think, any industry sector.

BS: Yeah. I think it's universal.

We talk about “fail forward.” Yes, it might be a failure. Yes, we'll have a long conversation about how you got to that decision in your own mind, whether it was the right decision, or did you not have the right information, however that worked.

But I'd much rather have that conversation with you than, “We haven't done anything in two weeks because I couldn't decide.”

CM: How do you—because I think a lot of times what's really hard for teams is to feel comfortable with failure.

How do you bring that back to your team and make them feel comfortable with, “Okay, yeah, I know this is going to come with a conversation, but I know I'm safe to make the decision”?

BS: Yeah, I think, one, saying it out loud. You got to say it out loud and say, “I'd rather have you fail.” And then we can talk about the why.

And I think the other thing is you have to be willing to—I just had this conversation today on a completely different matter—you have to be able to show your failures.

I think you have to be able to walk through it so they understand. They might look at you and say, “She's the owner of a business that's been around for 13 years. She's never failed.”

CM: I fail at something every day.

BS: Right. But are you saying enough? Showing them, “Listen, I was in this situation, and this was a complete failure. When I look at it, I was missing this piece of information. My gut was off on this.”

I think you have to be able to show those vulnerabilities to your people and to your team for them to be able to know that they can take the same risk.

We talk a lot about being entrepreneurial, and we want our people to be entrepreneurial. If you have a great business idea, we want to hear it, because if that's where your passion lies—

CM: Let's do it.

BS: We'll help you set this up. We'll help you launch. But don't have a failure to launch just because you think we might not want to hear the idea.

TBM #11 | Building Culture and Creating Community with Jeff Schwartz

Jeff Schwartz: We get feedback from our clients. It's on every email that goes out.

CM: We've seen it.

JS: If we've dropped the ball or something, oftentimes the clients will read our fundamental of the week and remind us that we missed it.

And we like that. We want our clients to help hold us accountable when we make a mistake.

Another thing, speaking of mistakes, we have a mistake policy that's sort of everywhere, ingrained in the company. And it's really simple and basic, and we share it with our clients all the time.

Rather than try and pretend that everything we do is going to be perfect, every project is going to go swimmingly, perfectly—

CM: That doesn't exist.

JS: I want people to make mistakes. I want people to fail forward and learn from those mistakes.

CM: Now, how do you encourage your team to make— I mean, we all say, “Create a safe space,” but it's one thing to say it. It's another thing to actually do it.

JS: I mean, I think this notion of a psychologically safe workspace right now is a buzzword. It's very popular.

And I think, at a minimum, what we do is it's posted throughout the company. It's referred to. It's talked about.

I think that you need to constantly pay attention to that, and you need to constantly find and recognize examples. Just like you want to positively praise and encourage certain behaviors, how do you respond, react to mistakes?

One of our fundamentals also is blameless problem-solving. They sort of go hand in hand, but they also can conflict a little bit.

CM: But I think there's a difference between blame and accountability.

JS: Right. And also part of this mistake policy is just: don't deny it and don't dwell on it.

A mistake has happened. We don't want to waste more time and energy worrying about what happened, the problem, who did it.

But truly, in our business, it happens regularly. A wrong tree shows up. We make a mistake. A near-miss accident. You name it.

What Leaders Do With Failure

Behind great leaders are the amazing people who keep companies moving in the day to day. Aaron Shapiro and Terry Egley trust the teams that they've built. They understand that nobody has all the answers, but through the ups and downs, everyone is working towards the same goal.

We all want success. You don't stop making mistakes, but you get better at recognizing them, talking about them, fixing them, and helping the people around you do the same.

TBM #7 | Succession by Fire: What Happens When Leadership Changes Overnight with Aaron Shapiro

Aaron Shapiro: One thing that is important is letting go of responsibility, trusting the people below you and letting them take that risk, and truly letting go.

Letting people do their job and getting out of their way, which I think is a really hard thing for managers and leaders to do.

CM: And business owners.

AS: Yeah. You want to see everything.

For someone to learn, you have to let them fail. And that's a hard thing to do because, if you would've done it, you probably wouldn't have failed—or not to that level.

So trust them, train them, and then just get out of their way.

CM: How do you deal with the failure side of it? I think that's the thing that's hardest for experienced operators and owners, because failure means the company fails. It's as if the company has to take a hit, right? And you have to let it happen.

AS: Yeah.

CM: And I believe it's so hard.

AS: I wish there was a better way, but I've tried to learn from other people's mistakes. It's just, when you make a mistake, you never forget it.

So it's just the best way to learn.

We say, in 50 years, we've made a lot of mistakes, so we're starting to get good at this.

CM: Okay, over 50 years.

I always tell people, you're not hiring me because of anything other than all the mistakes I've ever made. So you're not making them—you get the benefit of every mistake I have ever made.

Creating a culture around “it's okay to fail” is also tough.

AS: Yeah. And the one thing we say is, “Bad news early is good news.”

CM: Okay.

AS: If you made a mistake, let us know. And we're not going to scold you for that. We're going to embrace that.

And now you have a team to work together and fix your mistake.

Where it starts to get out of hand is when you make a mistake and you hide it, and then it snowballs into something that no one can fix.

CM: And it's at the eleventh-and-a-half hour.

If you'd been proactive—I always tell people time is options. If you tell me sooner, I have more options. If you wait to the very end, I am suddenly completely out of options, and we're going to be in trouble.

Please tell me in the beginning.

AS: Right. So that's something as a leader, too.

When you get bad news, your blood is going to boil and your natural reaction is to get upset. But you have to think of that person and be like, “Thank you for telling me. Thank you for coming to me.”

Because if you were to hear it from a client, that's a lot worse than the person coming to you with a mistake.

CM: Absolutely. Absolutely. Couldn't agree more with that.

TBM #9 | Everything is Figure-Outable: Building a Construction Business with Terry Egley

CM: How do you encourage your team to kind of run along with you?

Terry Egley: Well, fortunately, I have a very versatile team. They trust me. They know that if I'm saying, “Look, we need to do this,” then it's the right decision for us as a company and for them as employees, and they back me up.

I think they have the same mentality. I've built a strong enough team that they agree with: everything's figure-outable.

You can never be afraid to ask questions. I don't know everything. Nobody knows everything.

So you bring in people around you who know more.

For the lab, I hired some subcontractors who knew what they were doing.

CM: The lab.

TE: I brought in the best of the best that I had and asked all the questions in the world, like, “Wait, how does this work? What are we supposed to do here?”

Those kinds of things enabled us to do it.

And I think just building a team that can see your vision and participate in it is extremely helpful to scaling.

CM: I agree with you on that, being able to articulate that vision.

Sometimes I don't have it all figured out. I'm never going to have it all figured out.

TE: Right, right. We're going to wing it.

CM: We're going to wing it. It's going to be fun.

TE: Right? We're going to figure it out.

CM: We're going to order pizza.

TE: Exactly.

CM: We're going to make mistakes.

You know what I've mentioned here in the office many, many times? We don't do heart surgery. Just keep that in mind. No one's going to die.

TE: I use that a lot.

CM: It's everything—to your point, everything is figure-outable.

And you know what? So what if you make a mistake? We made a mistake. That means I learned something.

TE: Exactly. So if you don't make mistakes, you're not learning. That's for sure. I've learned a lot through the years.

CM: We've made a lot of mistakes.

TE: Yeah, it's just part of it. You have to be brave enough to make the mistakes, though.

CM: Yes, you do.

TE: And some failure brings out good results in the end sometimes. So I don't know if failure is the right word.

Mistakes bring out good results in the end.

CM: Failure is a wonderful teacher.

TE: It definitely will teach you lots of things.

CM: Absolutely.