Lessons from Failure: A Path to Growth

Summary

Business Lunch Podcast: "Lessons from Failure: A Path to Growth"

Host: Roland Frasier with co-host Ryan Deiss
Date: January 29, 2026

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Episode Overview

In this candid and insightful episode, Roland Frasier and Ryan Deiss dive into the invaluable lessons they've learned from failures and setbacks over the previous year. Framed as a "year in review," the conversation is both introspective and actionable, centering on how embracing and analyzing failure has led to substantial business and personal growth. Ryan shares his top five lessons, supported by Roland’s relatable anecdotes and probing questions, offering a practical playbook for entrepreneurs aiming to avoid costly mistakes and accelerate success in the coming year.

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Key Discussion Points & In-Depth Insights

The Value of Reflecting on Failure (00:14–00:56)

• Ryan’s “Annual Ritual”: Ryan describes his process of looking back at the year's failures and regrets, extracting lessons, and then mentally “turning the page.”

  • Quote: “For me, it actually is [cathartic]. I don’t enjoy it, but it’s cathartic. And you learn the most from failure.” (00:47 - Ryan)

• Success vs. Failure as Teachers: Both hosts agree that failure is the best teacher, far surpassing success in the depth of its lessons.

Reality vs. Metrics: When a "Good Year" Feels Hard (01:48–02:09)

• Despite growth in revenue and profitability, the year felt difficult due to layoffs, project closures, and uphill battles—a reminder that outward metrics don’t always match the internal journey.

Lesson 1: Distributions Are the Ultimate Sign of a Healthy Business (02:09–09:19)

• Shifting Focus from Growth to Distributions: In facing stalled growth, Ryan reframed meetings with the question: “What needs to be true to just be able to distribute $50K next month?”

  • This radically changed decision-making, emphasizing financial health over vanity metrics (like revenue or NPS).

• Distribution vs. Reinvestment: Roland probes the tension between distributing profit and “leaving money in for growth.” Ryan explains that businesses find ways to spend whatever is left in, often inefficiently. Taking money out forces rigorous capital allocation.

  • Quote: “The optimistic entrepreneur’s ability to spend will always, always, always outpace our ability to earn.” (05:21 - Ryan)
  • Quote: “If you take that money out... you’re going to think a lot harder about it.” (06:37 - Roland)

• Lessons Learned: The failure was tolerating a lack of profit and not adhering strictly to a “profits first” model.

Lesson 2: You (and Your Team) Can Only Do One Thing at a Time (10:15–13:20)

• Ryan recounts overcommitting to 17 initiatives in one quarter for a single company—with only two completed (and those being “stupid little things”).

  • Quote: “So much of this is just breaking our own rules.” (12:30 - Ryan)

• In the most productive quarter, the team chose five initiatives, completing them sequentially or by delegating to distinct teams.

Lesson 3: Show Me Your Calendar and I’ll Show You Your Priorities (13:20–14:46)

• Personal Productivity Audit: Ryan notes periods where his calendar was “wide open” led to unproductive months, as other people’s priorities filled the void.
  • Quote: “If we don’t claim our calendars, they get taken by somebody else.” (14:41 - Ryan)
• Action Point: Block out time intentionally for key initiatives; otherwise, important projects stall.

Lesson 4: Good Content Compounds—But It Takes Time (14:54–16:20)

• Compounding value from producing high-quality content is a long game. Their content strategy, started at the year’s beginning, only produced notable impact by Q4, at which point they could turn off paid traffic without hurting growth.
  • Quote: “The things that are the most valuable take the longest to build. If it happens quickly, it’s probably not going to be as valuable.” (15:46 - Ryan)

Lesson 5: The Excuse is the Reason (16:20–18:30)

• Ryan identifies a recurring pattern: when he rationalized avoiding hard decisions due to “reasonable” excuses, those were, in fact, the very reasons TO take action.
  • Examples: Not firing a “critical” team member, not sunsetting a legacy product.
  • Quote: "If we’ll flip it and make the excuse the reason... it’s much better advice." (17:45 - Ryan)

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Memorable Quotes & Moments

• On the Psychology of Distributions:
  Roland: “When you take the money out and it’s your money... all of a sudden, we’re asking a lot more questions than we were when it was just leaving it in there.” (08:09)

• On Overcommitting:
  Ryan: "We kind of started all 17, but got none of them to any point of completion. So many half-built bridges, so much wasted time.” (13:18)

• On Calendar Management:
  Ryan: "If you say you don’t have time for something... is it on your calendar? If it’s not, you have to acknowledge it simply isn’t as important...” (19:16–20:03)

• Summary Laugh:
  Ryan: “At some point, mistakes start being worth millions of dollars.” (21:12)

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Timestamps for Key Segments

• 00:14: Ryan describes his annual “failure and regret” review
• 02:09: Shift from growth thinking to focus on distributions
• 04:34: Roland challenges the distribution vs. reinvestment mindset
• 10:15: The consequences of trying to do too many things at once
• 14:46: How priorities are revealed and hijacked through calendar audits
• 15:46: The long, slow payoff of good content
• 16:20: The practice of flipping excuses into reasons for action
• 18:38–20:26: Quick review of all five key lessons

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Actionable Summary of the Five Lessons

1. Distributions = Health: Focus on building a business that can generate and distribute real profit, not just grow revenue.
2. Single-tasking Wins: Limit priorities for yourself and your company to maximize impact—do fewer, bigger things sequentially.
3. Calendar = Priorities: Your calendar is a mirror of what truly matters. If it’s not scheduled, it won’t get done.
4. Content Compounds (Slowly): High-value content efforts pay off, but only with patience and consistency.
5. Excuses Reveal the Path: The reason you’re avoiding an action is often the very reason you need to do it. Invert your excuses into action steps.

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Final Thoughts

Roland and Ryan’s honest review of failure reframes it as an essential part of achieving lasting business growth. Their five distilled lessons, drawn from real setbacks, serve as a potent checklist for anyone hoping to convert last year’s regrets into next year’s breakthroughs.

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Key Takeaway:
"Every million dollars helps." (21:33 – Roland) — Don’t let learned lessons go unheeded; each one has the potential to save or make millions.

Transcript

[A]

Hey, everybody.

[B]

Welcome to another episode of the Business Lunch Podcast with your hosts, Ryan Deiss and me, Roland Frazier, talking about all the cool things that we talk about over lunch. Ryan, what is today's topic for discussion?

[A]

So I just finished my annual ritual where I look back and I just simmer in all of my failure and regret for the year. That was nice. It sounds fun, doesn't it?

[B]

It sounds really cool. I just can't wait to do it tonight.

[A]

No, you know what I'm going to do?

[B]

I'm going to do it from a personal standpoint. I'm going to ask my kids over and my wife and say, hey, guys, tell me all the times that I let you down over the past 12 months. I like that. That sounds.

[A]

I think that's good.

[B]

It sounds invigorating.

[A]

I'll tell you, for me, it actually is. I don't enjoy it, but it is cathartic. And you learn the most from failure.

[B]

You learn way more from failure than success.

[A]

So success is a terrible teacher. Failure is the best. And so that's kind of the basic ideas I go through. And I look at what were all the failures, I list them out. What are all my low lights, and then I try to extract the lessons from them. And then that I just say, okay, I'm now going to literally turn the page. And I don't think about the failures and regrets anymore. I only think about the lessons. And so this is great, though, because.

[B]

Having it in a recorded form where I can refer back to it time and time again to bring up to you, anytime that, you know, I've done something maybe that's not perfect, I can be like, yeah, but remember last year when you blinked blank, blank, and I'll have a whole list of things. It's really going to be helpful to me, I think, for the coming year.

[A]

Well, some of these were lessons that I've had to learn, it seems like, every single year. So, yeah, I'm going to encourage you to bring some of these into. Remind me of some of these things. But it.

[C]

All right.

[A]

Which. This was an interesting year because, as you know, it was a hard year, Right? I mean, it was. It was. It was kind of cool because going and looking back, we were actually up revenue wise, we were up profitability wise, but it didn't feel that way.

[B]

I was thinking, like it was a hard 3/4 and then a hard month, and then the last two months, it just seemed like it finally all came together.

[A]

Yeah. I mean, before that, though, it was like, you know, layoffs. It was shuttering of projects. It was. I mean, it was just. It was like running in sand uphill. And so I guess what I'm saying is lots of lessons to be learned, and so I thought it'd be fun to. To share some of them. So I'm gonna kind of just throw out what they are, maybe give some context, and I'd love to get. Get your thoughts. So lesson number one. Distributions are the ultimate sign of a healthy business. And this lesson was learned. And I know you remember this, but we had one of our companies where going into the second quarter, this business had basically been flat year over year. And I was actually sitting in. In a meeting where they were talking about, okay, how are we going to grow? How are we going to break out of this fung. How are we going to start growing again? And everybody's throwing out kind of all the usual ideas, all the random acts of marketing and things that I know weren't going to work because it's all the same stuff we've talked about 50,000 times that didn't work the 50,000 times before. And so I just said, like, look, let's ask a different question. What needs to be true to just be able to distribute 50 grand next month? Now, for context, this business is doing about half a million dollars a month. That's about 10% of, you know, of its revenue. It's targeting 24%. So that shouldn't. It's not unreasonable, but it wasn't doing that. And I'll tell you, when it shifted from how do we grow to how do we distribute? The conversation completely changed, and it was a harder conversation. We talked about different parts of the business. It made for a. A really difficult next month. But within two months, the business was healthier. The business was actually growing. And that next quarter, we were able to make a much larger distribution than we had the previous two years. And so I would just. I think the takeaway is sometimes if you want to grow instead of focusing on growth, instead of focusing on sales, you might just be better off focusing on distributions. Because I continue to believe that the ultimate sign of a healthy business isn't revenue. It's not nps. It's the ability to distribute large chunks of profit. What say you?

[B]

I like it a lot. Yeah, I think. I think that it's interesting because I've always leaned towards distribution as an important thing, and I'd say that you and I, who, you know, we're aligned on that, but I think that most people are like, yeah, but I should be Putting that money back into the business so the business can grow. Because if I don't feed it, then, you know, it won't be able to grow. How, how do you answer that?

[A]

If the business needs it to grow, then you can put it back in. And so, I mean, what. And I learned this from you because you're being very gracious to me right now because there have been times when you and I in the past have butt head over this. So I'm like, we need to leave it in. And, and in reality, when we did leave it in the business, it just had a way of getting spent. Because if there's one thing I just. Yeah, it just gets spent because the optimistic entrepreneur's ability to spend will always, always, always outpace our ability to earn. Like, we can always come up with new and exciting ways to spend the money that we have. And so I think, yeah, I think you either need to say, okay, we're going to leave it in because here's the specific budgetary line item that we have for it. And everybody's agreed that this is how much we're going to invest. So it has, it's been budgeted for and it's been approved and this is what it's for and everybody's agreed to it. Or you take the money out and if the money needs, and if the business does need the money, then, then you do a capital call. And what's nice there is it gives you an opportunity to find out who really believes in this business. Because if some people, if somebody wants to put money back in the business, cool, they can do it then. And that gives you an opportunity to restructure the cap table if necessary. Yeah, yeah, that's my experience. When the money's out, people don't want to put it back in.

[B]

Yeah, that's what I was going to say is that, that, that when it is in the business and you're leaving it in, it's very easy to make an investment with absolutely no information, no due diligence, and very little if any accountability. If you take that money out and it's in your bank account and then you have to make a decision as an investor to take money out of your bank account and put it back into the business, you're going to think a lot harder about it. It's funny that it's as simple as that, but it absolutely is because you're looking at the, you're looking at it differently when you start and leave it in, you don't think of it as your money you think of it as the business's working capital or the business's money. When it's in your bank account, you think about it as, okay, business, I'm going to give you this, and if I do, what am I going to get and when am I going to get it, and what are you going to do with it? And how sure are we that what.

[A]

You'Re going to do is.

[B]

Right. Right. I love the mental change that happens just like that, when you take the money out and it's your money.

[A]

And that's ultimately what. Because again, and granted, you and I've been business partners for a long time. I've. I've evolved and changed my mind in a number of areas, this being one of the. One of the biggies, because I did used to feel like, oh, you need to leave a lot of money in. And when you were like, let's take it out, and if it needs to go back in, we can put it back in. And I remember thinking, well, that's reasonable. Let's do that.

[B]

It's so simple.

[A]

But the reality is, is, you know, if it said, like, we're going to take $100,000 out of the business, oh, I don't. I don't know. No, we should do that. The company needs it. Right. We'll say the company needs it. And yet if you take the hundred thousand out to your point, now the company says we could really use $100,000 because we want to go and do well, actually, we could really use $100,000. Now, I've got my. I've got my 50. You've got your 50, right. What do you need it for? All of a sudden, we're asking a lot more questions than we were when it was just leaving it in there.

[B]

Exactly.

[A]

I think, I think businesses would be a lot healthier. Um, I think that entrepreneurs would be much better capital allocators. They would think more like investors if they would take more money out of their business. So a. A hard lesson learned. And it's. It again, it's a lesson that we have to relearn. It's something that we teach, but it came out of a need to, to spark growth in a company. And that's. That's something that was unique in this area. It didn't come out of a what do we do with all this pesky extra cash? It came out of a, can we use this to spark growth? And the answer is yes.

[B]

So what was the failure in that, that you didn't do that sooner?

[A]

What do you the failure was tolerating. We said, I mean, we believe in a profits first model. And the failure was tolerating a lack of profits from the company.

[C]

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[A]

I mean, it really is just as simple as that. If we say that we're going to budget for a certain amount of profit and if that profit isn't there, that's not okay. And we have to agree that that's not okay. Yeah, it's just as simple as that. And so that's the failure number two. I can only do one thing at a time. And the same is true for everyone else. So I went back and I looked at and this is aligned with my lesson number three, which is show me your calendar and I'll show you your priorities. So lesson number two is related to the company. Lesson number three was related to me. So for the company, I went back and I looked at which quarter were we most productive and which quarter were we least productive.

[B]

Define productive.

[A]

We got the most key initiatives done that we set out to do and they were actually things that, that, that moved, that impacted our North Star metrics. So if you don't know anything about our how we do our strategic planning, every 90 days, it's generally three five one. We select three North Star metrics and it's like these are the three metrics that we believe we can optimize these three metrics, these are the three critical metrics that if optimized, are going to get us close to our goals. Five, five key initiatives. If we can execute these five key initiatives in the next 90 days, that's going to allow us to optimize those three North Star metrics. And then what's kind of the one big theme or rallying cry that's going to keep us focused? That's kind of the three five one that we do and that we teach and we say five, but really eight. If you want to stretch it to seven, you can kind of stretch it to seven. Well, in Q2 we had, wait for it, 17. 17.

[B]

But that was because you had seven companies, right?

[A]

No, it was just for one. Guess how many we got done.

[B]

None.

[A]

Two.

[B]

Nice. Okay, win two. That's almost 10%. No, that's, that's even more than 10% too.

[A]

I mean, and of course. Right. I mean, so much of this is.

[B]

Just.

[A]

Breaking our own, breaking our own rules. And it was the same like the next quarter Q3, one of our most productive picked five. The, the other thing is when you pick less things, you pick bigger things, you pick higher impact things because like the two things that we got done were like two stupid little things. I. So it really was just that simple. And, and when you have less things, then you allow yourselves to just do one of them at a time and actually get it finished. Whereas if you have a billion things, you feel the need to do all of them simultaneously. And while we only finished two things, we kind of started all 17, but got none of them to any point of completion. And so it was just so many half built bridges, so much, you know, wasted time.

[B]

Was it just fewer distributed focus that that caused it to be done or was it something else? Was it just there were not as many?

[A]

Yeah, it, I mean, we, we picked, yeah. When, when we picked the five, we knew that we actually had the capacity to do those five. And then we did one and got it done, and then we did the second one and got it done. Now some of them happened simultaneously, but they happened simultaneously because they were taken on by different teams. And so that was the distinction. And then, you know, lesson three, show me your calendar, I'll show you your priorities. I did the same thing for me personally. Normally what I do is I'm really good at keeping my calendar and like, I'll set meetings for myself and decide what I'm gonna like what I'm gonna do. So it doesn't have to be a meeting with somebody else. I'm just for this time, I'm gonna do this thing. It also allows me to go back and audit. There were times when I just couldn't remember what I did. You know, for example, like, you know, in the month of May, just. It's a blur. Like there are just some months that were a blur. When I go back and look at my calendar, it's just wide open. And so I can guarantee you if it was wide open, it got consumed by Somebody else's priorities. And I think that's the thing that we don't realize. If we don't claim our calendars, they get taken by somebody else.

[B]

Yeah, I like it. I like it. I think that's true. Makes sense. What's for. For.

[A]

This is one we talked about on a previous podcast. But good content takes time to compound. I was really shocked, and I shouldn't have been how long it took for our content efforts to actually pay off, because we basically started it at the beginning, and we really didn't start to see it have an impact until the fourth quarter. But by the fourth quarter, we were able to turn off paid traffic as a test. We still haven't really turned it back on, and leads and sales are continuing to accelerate. And so that was.

[B]

It.

[A]

It's a reminder that the things that are the most valuable take the longest to build. And if it happens quickly, it's probably not going to be as valuable. I don't know. Has that been your. I mean, again, we talked about this before, but has that kind of been your experience as well?

[B]

Yeah, I. I think it makes sense. I. I think it takes more time to build the things that are gonna have the most impact.

[A]

Lesson number five, and this was one that I'm just calling this. This is kind of going to be my theme going into next year, and it is across everything. And I'm calling it the excuse is the reason. Because I noticed something when I looked back on all of my biggest failures in 2025. In each case, there was something that I knew that I needed to do, but I had a reasonable excuse for not doing it, and so I didn't.

[B]

Nice.

[A]

And I think this is true for most of us. Right. It. I can't let that person go because they're just, you know, too critical. Right. We can't retire that product line. There's just too many legacy customers. Right. If we'll flip that and just in. I mean, it's just inversion. Right.

[B]

If.

[A]

If we'll flip it and we'll make the excuse. The reason I have to let this person go. They're too critical. We have to sunset this product line. There are so many legacy customers that are kind of holding the brand back.

[B]

Mm.

[A]

It's amazing how often the things that are difficult to do. If you'll take the excuse and invert it, it's much better advice than the actual excuses. And so when I. When I just go back and I look at all the things that I didn't do, had I done that, the Answer would have been a lot clearer. And so that's kind of something that I definitely want to make sure that I, that I bring in and that I'm, I've asked my wife, I'm asking you, I've asked Richard, when you hear me make an excuse, just to remind me like, hey, is there a chance that maybe the excuse is the reason? Because I think more times than not, that's the case.

[B]

Nice. All right, and you got one more.

[A]

No, that's five.

[B]

No, that was five. Okay, so let's review them.

[A]

So lesson number one, Distributions are the ultimate sign of a healthy business. Lesson number two, I can only do one thing at a time. And the same is true for everyone else.

[B]

And so just a couple people there because I, because I get number one is pretty easy. So if I'm listening or watching, it's okay, I gotta, my, my North Star, there's distributions. I, I don't understand it as well. For the second one.

[A]

Just, I mean, lesson two, limit your, limit your activities, limit your priorities. Just figure out what your right next thing is and just do one thing at a time. Okay, so have, I mean, it's obvious.

[B]

Like fewer things that are bigger that move the needle more. Sequentially executed.

[A]

Yeah, sequentially executed. It's again, not, not nothing there that you haven't heard a hundred thousand times. It's just something that when I looked back on why didn't stuff get done and where did we have a lot of wasted resources. It was that same mistake again. Lesson three, show me your calendar and I'll show you your priorities. Okay, so if I look at your calendar, if you say you don't have time for something, my ask is, is it on your calendar? And so if you're not willing to block it onto your calendar, you have to acknowledge that it simply isn't as important to you as the things that are on your calendar.

[B]

Yeah.

[A]

So if you want to get some of these forward moving things done, you know, in the business and stuff like that, then you have to, you have to put it on, on your calendar and you have to be intentional about it. And when I was intentional, those things got done. And when I wasn't intentional, other people's priorities got done for me.

[B]

Yeah.

[A]

Okay. Lesson four, Good content compounds. It just takes time. And so that's, I think content around brands is essential, but oh my gosh, it's going to take a while for it to build. And then lesson five, the excuse is the reason I like it. That's awesome. Those were my big, big lessons, big takeaways. Had I applied each and every one of those lessons in 2025, I estimate that I would have an extra, I don't know, billion, at least. Million. Couple, maybe.

[B]

Couple.

[A]

I'm not kidding. I mean, at some point, mistakes start being worth millions of dollars. And I think it's safe to say that some of these mistakes, you know, cost us at least that much this last year. And so I'm hoping that, yeah, this year, if we can implement some of these things, they can save us or make us that much. And maybe they save or make some of our listeners even more.

[B]

And if you take nothing else from this episode, remember, every million dollars helps.

[A]

I've always said it, always said it.

[B]

Ever since I've known you.

[A]

Yeah.

[B]

Well, guys, I think that's great. Ryan, thank you for sharing that. It's really nice. I think that that will help a lot of people. Those are five very, very good things to focus on. If you guys found it helpful, please share the episode. Feel free to give us a, like a review, distribute us to all your friends and take some of this stuff and actually do it would make us very, very happy. We're available on socials.

[A]

Love your feedback.

[B]

And we'll see you next time on the next Business lunch.