The Happy Engineer Podcast

082: Avoid $1 Million Dollar Management Mistakes! Entrepreneurial Tips for Careers with Dan Cumberland | 3x SaaS Founder

In this episode, we chat with 3x SaaS (Software as a Service) company Founder, Product Strategist with the Venture Studio NineTwoThree, and host of a top 1% podcast, Dan Cumberland.

We cover what every engineering leader who wants to start their own company needs to hear. The cool part is that these ideas will help employees in your leadership just as much as entrepreneurs!

When do you know it’s time to start? How do you accelerate success and avoid huge mistakes? Am I really an entrepreneur? How do I balance business with life outside the company?

Dan and I answer these questions and more.

His work has been featured in Entrepreneur Magazine, Fast Company, and many more. You will see why when you meet him. I loved this conversation!

So press play and let’s chat… it’s time to save yourself $1 million dollars in self management mistakes!

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The Happy Engineer Podcast




081: The 6 Essential Core Values of Leadership with David Valentine | Marketing Madman and $$ Billion Dollar Leader




That was a great conversation with many powerful takeaways! 

There is one line in there that really popped for me. 

Dan said, “You can’t just optimize for the future.

You may have heard that before, and it deserves underscoring. 

You can’t just optimize for the future. Now is the only moment you ever have.

A lot of times people will talk about someone who’s stuck in the past. 

They’re stuck living in the past, you know, reliving the glory days of high school football, the jokes that might be made in movies about, going to Applebee’s and bragging about your high school, varsity football games or whatever.

Maybe you see in yourself some patterns of living in the past. 

Well, here’s what I didn’t know until I became a coach. Just as easily as getting stuck in the past, you can get stuck in the future. 

You can fall into a pattern of living your life in the future, and it’s just as damaging in some cases to the quality of your life as getting stuck in the past. 

Now, let me share with you what that looked like for me. 

I’m a really positive, very optimistic, and very visionary leader.

I love to cast the vision. I love to go out into the future, to dream about what’s possible, to imagine things in a better state the way they could be, the kind of impact that I want to make through OACO or through my life and my marriage, through my family, the things that matter most to me.

I love going out and visioning and dreaming, and imagining how great the future could be and then building plans to go and create that. 

But here’s what happened to me, and I noticed this pattern in working with my coach a few years ago. 

I got caught spending time every single day simply sitting around thinking again, rethinking over and over about my future and about all of the plans that I would need to execute to get to that future. 

And watching all the metrics and measures that would tell me if I was on track or off track and tweaking everything. 

Thinking about how to optimize my future instead of actually doing the work that needed to happen that day. 

Even as a coach, it’s easy to fall into these kinds of mistakes. 

And here’s what I want you to know. There’s nothing wrong with dreaming, envisioning, imagining a great future. 

In fact, there’s a lot of things right about doing that. But the thing about the future that’s so attractive is that the future can always be better than the present.

It’s easy for us to ignore the pain, the struggle, the trials, the tribulations of what’s on your plate in your life right now. 

The things that you’re afraid of, the things that are uncomfortable, the things you don’t want to do because it’s going to be hard.

You might fail the conversations that you don’t want to have because facing that person, it could create conflict and you don’t want to go there.

Well in the future none of those things exist in the future. 

Everything’s going to be better in the future. 

I’m making more money in the future. 

I have a better job in the future. 

I’ve got a better boss in the future. 

I work for a better company in the future. 

I have more vacation time in the future. 

I’m not burned out in the future. 

I’ll be retired and happy in the future.

This is a dangerous pattern that our subconscious mind will latch onto as an escape from facing what needs to be faced in the present. 

Don’t get trapped living in the future because life does not happen in the future. 

Your life is happening right now and now is the only moment you will ever have when you’re thinking about the future, your burning daylight of the now, spending that energy and time of your mind in something that doesn’t actually exist.

The future will never be here. Only now will be here. 

Your life is a continuous flow of now’s visioning, planning, taking intentional strategic action to make the future better. 

Even more importantly, when it becomes an escape from facing the hard things of your present. Then we need to have a tough and honest conversation with ourselves. 

A great life is nothing more than the sum of many great days. 

Live in the present. Execute in the present. Enjoy life in the present. Be happy in the present.

If you need help with that, I want to invite you again to join us in our signature program, the Lifestyle Engineering Blueprint. This is exactly the kind of work that we’re helping our clients to accomplish and achieve in their life. 

Yes, we’re going to cast a vision. We’re going to set smart goals. We’re going to build really strategic plans, and we’re gonna strengthen the confidence and the courage you need to take action and execute those plans to hold you accountable, to follow through, and be at your best.

Those things are all going to happen as part of this powerful community. 

With the support and coaching from me and my team right there beside you every step of the way. 

This Blueprint program is going to help you find that balance of really powerful planning for the future, but then pulling all that energy back to the present and facing the hard things in your life and in your career as an engineering leader.

You get there by taking courageous action today, not by putting more plans in place for tomorrow. If you need help with that, book a call with my team.

Take Dan’s message to heart from this conversation today. You can’t just optimize for the future. The time to live your life is right now.

Keep crushing comfort out there, create courage, and let’s do this.



Dan Cumberland is on a mission to help bootstrapped entrepreneurs avoid burnout. Having hit the bottom before, he’s passionate about helping entrepreneurs get the insights they need to recalibrate their work/life balance so they have energy and motivation to keep going.

He is a 3x SaaS founder, serial entrepreneur, host of The Meaning Movement Podcast (, and a Product Strategist with the Venture Studio

His work has been featured in Entrepreneur Magazine, Fast Company, and more.

His most recent project is a software for repurposing speech based audio and video into viral ready shorts:

Outside of business he’s a father, husband, avid reader, runner, health and fitness optimizer, and volunteer with the Carbon Almanac. He lives in Seattle with his wife and three kids.





Please note the full transcript is 90-95% accuracy. Reference the podcast audio to confirm exact quotations.

[00:00:00] Zach White: All right! Happy engineer, welcome back! I’m here with Dan Cumberland. Dan, thank you so much for making time, your generosity to be here with us today. Welcome to The Happy Engineer Podcast man. 

[00:00:13] Dan Cumberland: I love it. Thank you so much for the chance to be here. So pumped to, to talk with you and, and share with your audience here today.

Expand to Read Full Transcript

[00:00:20] Zach White: Dan really got me energized and there’s a lot of things that I can’t wait to dig into and I mentioned it to you already, but. One of the reasons this conversation has me jazzed is because a big percentage of the engineering leaders that I work with and that I coach at OACO have a passion or a deep desire inside them to pursue an entrepreneurial journey.

[00:00:46] At some point, you know, they’re building. Building products for amazing companies and they have this desire one day to go do something on their own. And that’s a big part of your story, not, to mention this Gen Z population, the data around Gen Z, the most entrepreneurial generation we’ve seen since.

[00:01:03] Before the Industrial Revolution, when everybody in the way was their own entrepreneur was, this is such an important conversation for that reason. But before we talk, Dan’s success and Seven figure SaaS companies and all of what you’ve learned and the meaning, movement, all these pieces. I actually wanna back the clock way up if you’re open to it.

[00:01:22] Yes. And I want to hear about your time as the pastor of student ministries at Oak Community Church, because I think it’s really amazing that that’s. Everything’s the began for you. Yes. And so would you just tell us, like, I remember how I terrorized my youth pastor back in the day at church. So, so Dan, like, tell us, what’s that craziest or wildest memory from your days?

[00:01:46] Uh, as a pastor 

[00:01:47] Dan Cumberland: at I Church did not expect, I did not expect this. Uh, but this is fantastic, man. my time in youth ministry, I’m just laughing at this question cause it’s so, it’s so great. I so rarely get asked about this, phase of life. youth ministry. It’s a, it’s a wild, it’s a wild ride.

[00:02:02] A lot of, um, dodge ball, a lot of, just fun, retreats. Um, junior high and high school kids are just, They just love having fun and being, being crazy. I’m trying to think of like what some of the highlights are. I mean, there’s plenty of like all nighters, like that’s like a thing that was, I don’t know if that’s, if, if that’s still a thing in, youth ministry, but we would like stack up all these events back to back.

[00:02:24] We’d go like, you know, bowling at 2:00 AM and go to a, arcade at 4:00 AM and like, keep the kids out all night. All you know, supervised. Trans transported on a bus and everything like that. And, everyone crashes hard and the parents come and pick up their kids at, 6:00 AM on a Saturday at a Sunday morning, and they all go to bed for, I I, I always view that hopefully as a, like a gift to the parents that they just.

[00:02:45] The, the kids just get to sleep one night after sleep, the whole, the whole weekend. . Um, I’m trying to think of like what, there’s one thing. So 1 event that we would always do every, Halloween we would have what we’d call a halloweeny roast. Um, okay. as, as an alternative to like, trick or treating or going out partying and, you know, things like that.

[00:03:04] Um, we would have a big bonfire, have a bunch of hotdogs, and we played this game that we called, uh, pumpkin volleyball, where you’d have two teams with a, each one had a, uh, a bedsheet and the team did like five or five, five to seven people, and a bedsheet on each side of a volleyball net, then a pumpkin pipe pumpkin you’d put in the middle of the bed.

[00:03:24] and they had to get the pumpkin over the net by the relaxing the sheet. Sure, sure. Pulling it tot and launching it, and then the other team has to catch it coordinated, like catch it, and then. Go back and forth and it was just hilarious. And, I mean, sometimes kids would get hit with a pumpkin.

[00:03:39] They’re not that heavy, so it wouldn’t hurt. Uh, but like so much just, just fun and chaos. I love that. Organized chaos. I 

[00:03:46] Zach White: love that. Yeah. Not to be insensitive to kids, but you know, getting hit by the occasional pumpkins, probably good for you, you know, build’s character. That’s what my dad would’ve said.

[00:03:54] Build’s character something, it 

[00:03:55] Dan Cumberland: builds character . 

[00:03:57] Zach White: Oh, that’s too fun. And of course, all the engineering leaders. that I know are thinking, okay, we could, calculate this, get this right on how, how hard to pull the sheet we could win this game. Totally problem. It 

[00:04:07] Dan Cumberland: was like one of those things that, like when the, the team first starts, they try to throw a pumpkin and it doesn’t even go anywhere.

[00:04:12] But then by the end, after they’ve had a few reps in, they start to get pretty, I mean, they kind of start to get dangerous. Like the, the height starts increasing and yeah, it gets, it gets pretty crazy. 

[00:04:21] Zach White: That’s so I love it. I love it. Thanks for sharing that. So, so Dan, in those. What was it that actually shifted your focus around what you wanted to do for your vocation?

[00:04:31] Yeah. Into what would become SAS tech company. entrepreneurship. Yes. Where was the point where that actually entered your 

[00:04:39] Dan Cumberland: world? Yeah. Right. Because it’s not a straight line. And that’s one, one of the things that I’m always passionate about is sharing, like that our career paths are often, I’d say even, usually not, uh, not a straight line.

[00:04:50] Um, yeah. In today’s day and age, Youth Finishy was the stories I was telling. And many of those kids I’m still friends with and connect with. And it’s just like, that’s the best part is just the relationships that came out of it. And that was the best part while I was there.

[00:05:01] But there were a lot of other parts of the, just, I was a bit of a square, peg in a round hole. for people in the audience who might have a faith background, this might make, more sense than than others. , I thought I was like capital C called to be a youth pastor.

[00:05:15] And then I got into it and it didn’t, it didn’t work. And so then I had these just major questions, this existential question of what, what now? And really, instead of the question being like, okay, that’s not a good fit for me. You know, what else should I, should I try? It’s like I. Supposed to be, this was supposed to be what I was gonna do with my life.

[00:05:34] This is what I’m supposed to be doing. And so then I was the problem and so that question kind of turned inwardly on myself, which results in a lot of, lot of just. Depression. I was struggling with, I would have like, I don’t know, these kind of like emotional breakdowns before, before big events and things where I would just like, have a hard time feeling excited.

[00:05:53] Sure. Hard time being motivated. Sometimes just like in, literally in tears at, at times. but didn’t, didn’t know where to turn. , eventually got into therapy, got some good coaching, and started getting some guidance around we could ask better, questions to get the kind of answers that we’re mm-hmm.

[00:06:09] we’re, we’re, we’re seeking here. Mm-hmm. . Um, and so it had some help finding, finding those questions. and through that I mean there was this, one very palpable moment when I was on a retreat with a, uh, leadership coach and we were taking turns about four or five people on this retreat. It was very, Sharing what has been going on in our, you know, our lives over the last year or so, and, um, with the group.

[00:06:30] And the group would give feedback. So I would like to talk to all about what we’re doing in the youth ministry and blah, blah, blah, all this stuff. And then just kind of open it up for questions. And the coach who said he, he said, Dan, who told you you needed to be a youth pastor? Yeah. Uh, like that was the very first question that he asked.

[00:06:44] And like, it was such a good and powerful question. It kind of made me mad at first. I was like, well, God told me, you know, um, , but I, I, I began to have better questions like that, that began to help me unwind this ball of, of, thread in in my life and start following that thread into the future of like, where, where do I feel alive?

[00:07:01] where do I find, Myself, being curious and really started connecting the dots that I get really excited about these existential questions I love, like the human experience. Why are we here? like, what gets us excited? and decided to follow that to, to grad school and um, did an interdisciplinary degree around.

[00:07:18] Dan Cumberland: Theology, psychology and Culture, which is gonna get to the entrepreneurial part, I promise. I’m gonna get there. Okay. Okay. Um, but then outta that program also, I just felt like I, I think I, I discovered for the first time some permission to let myself be, I think who I, who I am, who I’m made to be. 

[00:07:33] Zach White: Ooh.

[00:07:34] Which is, uh, I love that word. Permission, Dan. Yes. That’s permission is so huge. Powerful. Yeah. 

[00:07:40] Dan Cumberland: Yes. Yes. And I think part of that permission for me manifested itself in like just realizing and accepting that I like to have a lot of things going on. I like to go where there is no map. I like to figure things out as I, as I go.

[00:07:53] And, um, and so out of that program, two things happened. One is, you know, this entrepreneurial, I gave some, some space for the entrepreneur inside of me to. And secondly, I started the Meaning Movement, which is a podcast and a, business all around, more recently focused on helping entrepreneurs find balance between the life that we want to live.

[00:08:13] And the business that we’re, we’re building started really more focused on kind of the same questions, but really focused at careers and career transitions. And so I started this business and I had no idea how to, how to be an entrepreneur, how to run a business. So I started like looking for ways to, to educate myself and, um, Found, started doing like externships, I guess you could call them her internships.

[00:08:35] Um, and one of those ended up being the guy who was at a PE firm who bought a software platform. He asked me to step in to run it, and so I just jumped into the deep end of, running a, running a software company. Okay. Okay. And, I’m taking a very long, probably giving more context 

[00:08:50] Zach White: context than, but, but I love, I love the arc of this, Dan.

[00:08:53] Yes. Let’s pause right there for a second because I think what you. That’s so important, what I wanna build on. Yes. I love how. Question of who told you That you should be fill in the blank. Mm-hmm. Yeah. And And sometimes you think it was yourself. Yeah. Sometimes you feel capital C called. And I, I think whether you have a religious or faith background or not, everybody can connect to that same idea that somehow I ended up with this deep faith or belief Yes.

[00:09:24] That this is where I ought to go. Yes. You know, Dan, I’ve got a lot of engineering leaders I work with who’ll tell me things like, well, in my family you only had three choices. You could be an engineer, a doctor, or a lawyer. And I was good at math and science, so I became an engineer. Yes. You know, and you could say, well, so who told you?

[00:09:42] to be an engineer. Well, was it really you or was it your parents? Yes. Was it really you or was it culture? Yes, or you know, I really wanted to be in a high income occupation and engineering was at the top of the list in high school for our occupations, so I went to engineering school. A lot of people end up that way and then 10 years into their career they’re asking the same questions that you just described, like, yes, I don’t feel truly connected to this or, Even when they love engineering, they still find themselves lost or losing the plot of what this is all about along the way.

[00:10:15] And so, yep. Yep. I think what you shared is so important. Everybody needs to ask themselves at multiple points in their journey, who told me that this is where I need to be, and have I a hundred percent made an intentional choice for where I want to go next? And it doesn’t have to be a. Line. So Yes, yes.

[00:10:34] Here you are. You get asked. Love that. To jump in, well just to, just to answer Oh, go 

[00:10:38] Dan Cumberland: ahead. That just a little bit please. Just one, one more layer is like, uh, the answer to that question is my youth pastor, which probably isn’t a sur surprise for someone who’s been in youth ministry, but like totally my youth pastor told me I needed to, to be a youth pastor cuz that’s what was important to him and he was an important figure in my life at that really pivotal moment.

[00:10:55] And I say that as just an example of, we have these stories or, Narratives about ourselves. Mm-hmm. , about the world, about the choices that we, should and shouldn’t be making. Yeah. That just, we absorb. And I, my youth pastor is a great, a great guy. had great intentions and had a great impact on my life in a lot of good ways.

[00:11:13] That was one way that didn’t serve me the best. Right. That wasn’t his, fault. He didn’t do it on purpose. Right, but just being in his, in, in his orbit, that’s like one of his values that I, I inherited. And I think that, Is a case in point of what you’re saying of like, we just absorb from culture, from families, from the institutions, the schools we go to, all these things that just then end up dictating how we think about what’s possible for us and the choices that we make.

[00:11:39] And so I just love that you’re inviting people to just become more conscious of, of yeah. who are the other voices in the room when you’re thinking about, and talking about who you are and what you. . 

[00:11:50] Zach White: So Dan, I know we don’t have time today to unpack all of your history. I know, right.

[00:11:54] In SaaS, in uh, entrepreneurship, but Yeah. You know, a couple of the, brief things I saw about you and some really amazing success, built three companies, seven figure revenue companies in SaaS, software as a service technologies. Yeah. Tell us, where do you think the most important moment of, either the pinnacle of that, or maybe it’s the opposite, like the really challenging bits.

[00:12:16] Yes. But for that aspiring entrepreneur out there who might want to understand what a pivot in their career or life could look like to do it. Yeah. Tell us a little bit about, you know, how did that flow? What were the highlights for you in entrepreneurship? . 

[00:12:30] Yeah, for me, I mean, it takes me to, to a couple places.

[00:12:33] I got lucky in some, I mean, that’s always, always a part of it. Um, and I feel really, really blessed by the opportunities that the doors, doors that opened, but the doors only opened. because you say yes to them and because you have the have the eyes to see them, and you make yourself, available.

[00:12:47] Dan Cumberland: And so I think that’s a big part of my story. As I look back, everything that I’ve been able to do has been accomplished through two things. One is just saying yes even when you don’t know what the outcome’s gonna be. Ooh. And then secondly, , through people. so investing in the people, being available, um, you know, giving back as much as I can, to the people of my life.

[00:13:07] And that just has led to opportunities. That’s what led to the opportunity at that private equity firm to step in and, and join the world of software. and then from that, a partnership led to, what was a sales agency that pivoted into, a SaaS studio, launching software, seeing, seeing what sticks.

[00:13:23] which has led to, to other opportunities. and so I don’t know if that’s, this totally answers the question, but those are like two of the ideas that really stand out to me and look at my, at my 

[00:13:32] Zach White: journey. Let’s talk about that. Doors are open when you say yes idea, because yeah, this is something if I’m being.

[00:13:43] Broad brush where I see engineering leaders struggle and where I have struggled in my own journey as an engineer. Yeah. In my original, career path, the idea of. Hey, I can do a hundred different things for my first business. Yes, yes. And I don’t know which one I want. Yes. And so I’m stuck continuing in my career path.

[00:14:06] Uhhuh , which is the morphine drip of a nice, steady, big paycheck and that annual bonus and you know, all the accolades and the significance and recognition that come with doing it. Yes. But I can give lip service to the idea that one day I wanna be an entrepreneur, but I just don’t know. what I wanna do yet I’m not sure which company I want to start.

[00:14:28] Yes, and I’ve, I’ve heard so many people in that kind of situation, and so I would’ve described it then Dan as well. All the doors are currently closed for me. I don’t, I don’t see the open door. Yes, I can tell you now. They were all open and I just said, I was saying no. Yeah. Yeah. But it didn’t feel that way at the time.

[00:14:52] So can you just tell us for yourself, what was that like, a little deeper? Or maybe how would you coach someone like Zach who’s stuck in that place of, yeah. Well, Dan, I wanna do what you’re doing. I just don’t know. And it feels like all the doors are closed. What would you say to that? 

[00:15:05] Dan Cumberland: Yeah, I’ve got so many things to say.

[00:15:07] This is such a good, such a good question. So I think of,when I hear that and think of people that are in that space, it’s like you’re trying to drive across the country. Not hit any red lights in your car as you drive, which like, as the engineers listening, there might be like, oh, I could figure this out and I could time it just for you.

[00:15:25] Like, but, but it’s like, you know, you don’t know. you don’t know what’s gonna come. Yeah. You don’t know what’s around the corner and you can’t, plan it all out, so you don’t, there’s like, even the ideas for businesses that you have right now, what might be the perfect business you might not have even thought of, or you get three steps into it and you realize that you’re thinking about it in the wrong.

[00:15:44] The product market fit is off. There’s, if you just change this product just a little bit, you’ll find whole, whole new realm of possibility. And so that’s one piece is like, it’s impossible. It’s impossible to know. Yeah. And I think related to that, we wanna have the perfect.

[00:15:59] thing to do. And I remember hearing, um, Seth Goden, He’s, he’s an Olympic author and, and, marketer. we were talking about the problems of the environment, uh, environmental change, climate change, all these things and, all the many big problems in the world.

[00:16:12] Dan Cumberland: And someone asked him, how do, how do you choose which problem to focus on when there’s so many, so many big problem? what he said has stuck with me. Cause it applies so well to this, this quandary that we’re we’re talking about right now, which is that you have to forgive yourself for not being able to do the perfect.

[00:16:30] in order to free yourself to do the good. And so when I hear what you’re, you’re presenting as like, oh, I have all these ideas, I don’t like, I don’t know which one to choose. I hear in that like, this stuckness of, I want to choose the perfect one when like, really probably any of them are great place to start because all of them are gonna change as you go and create more opportunity, for you.

[00:16:51] So I want to invite people, to. To that as well. And then the third thing, is I think about, um, the golden hand handcuff you said like the, the morphine drip of the, of the great salary.

[00:17:01] Yes. Which is like a real thing for, you know, engineer. A lot of the folks in the audience I’m sure making really, absolutely great salaries. I think if you could map. , on two ax axis. So on one ax axis you’ll have self-actualization or, meaning purpose, however you wanna think about that.

[00:17:17] Mm-hmm. . Mm-hmm. On the other a axis you’ll have, Profit, which could be, you know, your paycheck, it could be the benefits, all those kinds of things, which then divides into, you know, four, four quadrants that are high in one and, and low, low in the other. So let’s say that engineering, like maybe it’s not, you know, the highest as far as self-actualization.

[00:17:34] Maybe it’s even on the low side for some folks here and they, they feel like, I really don’t love this, but it’s really high on the, that paying side. The dream job would be, you’re, you’re making, you know, making millions, doing work you love, benefiting lots of people. All all those things.

[00:17:50] And we want to go from wherever we are straight to there. But the problem is we wouldn’t have the ice to see it if it was right there in front of us. Mm-hmm. And so The framework I wanna invite people to is, you know, maybe draw this out on a piece of paper, mark where you are right now, and then think about what would it look like to go.

[00:18:09] a smidge. towards more self-actualization or, uh, you know, however we wanna talk about that more meaning, more purpose in your work, what does it look like to just take one step and what might that next step be? Instead of trying to just go, okay, I need to quit my job, but then what about my family and what about the mortgage and all of these things, which then just get you, they convince you that it’s not possible for you to make change.

[00:18:33] So that’s just another concept 

[00:18:35] Zach White: of wanna offer a hundred percent. Yeah. I. It’s really common in my own journey as an engineer to want to map out the whole problem because a lot of our projects that we do in our careers involve planning from start to finish. It involves doing a level of prediction. And of course, to your point, we’re not gonna be right.

[00:18:54] We’re not gonna get all the green lights. Yes. But a lot of times those problems are plantable and solvable in some capacity. Yep. You know, as, as this Y equals Zev X formula. Yes. Type of approach. And when we enter into our life, which is this infinite game, this idea where it’s all unpredictable, it can be a bit overwhelming.

[00:19:14] And so I love the smallest next step. What’s the simplest Yes, smallest. And I give my clients ideas like, Hey, look, you don’t know which business you wanna start. In the next 30 days, how many people could you talk to who own a business and learn a little more? Hey, you’re not sure if you wanna do software or, fulfilled by Amazon products?

[00:19:34] Cool. let’s go read a few blogs or get some information about both in the next week and then come back. We’ll, tell me what you learned. Yes. Let’s just keep putting one foot in front of the other. Love that along the journey. And I think it’s important, Dan, too, and I’d love your thoughts on.

[00:19:48] as we unpack the entrepreneurial journey. I don’t want someone who says, but I like being a W2 engineer. I wanna build on that access. Mm. To feel. That that’s not acceptable or that that’s a bad hundred thing percent. so if you’re in that boat, maybe you hear that person saying, Hey, well, this isn’t for me.

[00:20:05] Then if it’s all about entrepreneurship, what would you say in response to that? Yeah. 

[00:20:10] Dan Cumberland: Well, I, I would say first. That’s totally, that’s totally fine. Not everyone’s meant to be an entrepreneur. It’s not the path for everyone. But I would say, I think about entrepreneurship as a, it’s a.

[00:20:21] It’s a really fun lens, and this is, you know, because I’m an entrepreneur, It’s a really fun lens to look at the human experience. Yeah. Through, because it, because in order to be an entrepreneur, you’re always having to, to grow. You’re always having to become the next version of yourself in order to take your company where, it needs to go, but, , that experience of growth, that experience of becoming the next, the next iteration of yourself is true of all people.

[00:20:43] Even though it’s easier to point at an entrepreneur and show yes, like here’s where you’re growing, here’s how you know, you’re learning a advertising, you’re learning marketing, you’re learning part, like all these things. But the same is true of someone who’s got their W2 and in their job.

[00:20:56] So the invitation I would offer to that person is to think about where’s their growth edge in their current. and how can they become the next iteration of themselves? What is it that’s being, uh, uh, this is gonna sound very woo woo, but for, for, for engineers. But like, what, what is it that’s emerging or being birthed inside of them?

[00:21:15] What’s the next version of themselves that’s trying to come out and find some expression in the world, and how can they give expression to that? in their job, as a hobby or as a side project or whatever, it might be. Mm-hmm. . And so that’s mm-hmm. , that’s where mm-hmm. . I, I take that, 

[00:21:27] Zach White: that idea.

[00:21:28] So glad you said that. I, I couldn’t agree more. And I think it’s a powerful thing for every engineering leader, no matter what you aspire for your vocation. Yes. If you don’t wanna start a company, or you, do, doesn’t matter. Yeah. You are. Lifestyle engineer, as we call it at OACO, in your journey, you are the ceo, you’re the entrepreneur who’s creating value within the framework of what you want to see your life look like.

[00:21:53] Yes. So if that’s in your health, if that’s in your marriage, if that’s for your kids, if that’s for yes. You know your hobbies. . Mm-hmm. , you are entrepreneurially creating value in your universe, . Yes. That you can influence. Yes. No matter what your job 

[00:22:06] Dan Cumberland: is. hundred percent agree. And I’ll sign my name on that, on that statement.

[00:22:11] And I think that it’s an invitation and, and maybe entrepreneur again, I think it’s kind of like this place, this placeholder for this idea of you’re taking owner. And you’re taking responsibility. And so the invitation to the W two, engineer is, yeah, sure. You’re, maybe you’re not an entrepreneur, but what does it look like for you to take full and extreme ownership over your life?

[00:22:31] Yeah. And have that mindset. As the way you view yourself and your, your world. to know that like whatever’s gonna happen to you is you’re not in a place where you just need to wait for it to happen, but you need to proactively make it happen. And what does it look like for you to take that mindset to your W2 job and to the rest of your life?

[00:22:48] Awesome. So 

[00:22:49] Zach White: good. Dan, one of the things in. Story in your bio that I just wanted to quickly touch while we’re on the topic of the SaaS companies Yes. Was Million Dollar Mistakes Okay. That Entrepreneurs make. Okay. And I feel like it would be unfair to the engineering leader listening who’s getting a chance to gain wisdom from Dan.

[00:23:08] Not to quickly say, what’s that number one? Million dollar mistake that new entrepreneurs or even seasoned to veteran entrepreneurs make that you’ve learned from your, your journey 

[00:23:19] Dan Cumberland: through building sales companies. I, I love, I love the topic of million dollar mistakes, cuz there, there are a few that I think many entrepreneurs make and they’re not the ones that we usually think they are.

[00:23:28] so we, we think a million dollar mistakes we think of, bad partnerships we think of, of, you know, campaigns that went. You know, failed launches or whatever, it might be. Mm-hmm. , I think the biggest mistake, and this is, you know, from my point of view, I’m not a VC backed entrepreneur.

[00:23:41] I’m not going down that path. I’m bootstrapped, I’m building businesses, you know, the long and slow way in some, in some ways, and I look around me at other entrepreneurs that are doing similar, similar work. Most of, even though the VC backed Silicon Valley entrepreneur gets the most airtime in, in sure in the press, that’s not, uh, the majority and the majority are absolutely are people like, you and me, who are, who are out there doing, doing the work.

[00:24:04] And the million dollar mistake that we make is around pace and it’s around sustainability and it’s. Not what we’re doing, not why we’re doing it, but how we’re going about doing it, and to put it bluntly, is that we burn ourselves out, chasing after, you know, we, we burn ourselves out, for a life that we, we don’t.

[00:24:23] Love because we’re just sacrificing it all for the business in order to gain a future that may never come because the business may never find that hockey stick growth curve. And that day when we can, take that six months off and travel the world while the business runs without us, may never, may never come.

[00:24:42] And so the mistakes, the way that it manifests itself is by burning ourselves out so that we. So that we sell, so that some other aspect of life gets sacrificed, particularly relationships, friendships, partnerships, marriages, all of those things, because we’ve sold ourselves, tied ourselves to this, this business that we’re creating, we become entrepreneurs typically for, for three, three reasons.

[00:25:05] We want a life that has less stress. . We want more freedom and we want to make more money. Yes. And often we get into it and then we find that we’re not doing any of those things. We’re not getting any of those things. And instead we, we quit one job and now we have 20, and like in a bit of a prison of our own making and, and have to feed the monster.

[00:25:24] It’s like Frankenstein monster. We built this thing and it will literally kill us unless we put some boundaries around how we go about spending our time and the. Day out of our business. And so that’s how I think about these million dollar mistakes. And I think a simple, question that we can ask to say, are we on a, are we on a path?

[00:25:42] Are you on a path towards a million dollar mistake Is to, to ask the question, if you had to live your last 90 days on repeat. How happy would you be? 

[00:25:54] Zach White: Ooh, 

[00:25:55] Dan Cumberland: say that again. And I think for a lot of us, we’re like, yeah, I’m not, I’m, I’m optimizing for the future. I’m, and I’m really good at optimizing for the future.

[00:26:03] I’m really good at delayed gratification, but you can’t. Just have delayed gratification. You can’t just optimize for the future because all you have is right now, and I have three kids, seven, four, and two, and their lives are, their childhood is passing me by, and if I’m not available and present for that, then why am I doing this in the first place?

[00:26:24] Zach White: Hmm. That is such a good question. And Dan, I love it because one of the things I share with clients is I, I generally don’t care for the advice about. You know, if you died tomorrow, what would you do? You wouldn’t be doing this because Yeah, statistically speaking, you’re probably not going to, and none of us would, I mean, you and I would not be having this conversation if I knew I was gonna die tomorrow.

[00:26:45] And so I, yes. I don’t find that to be productive, in insightful. In many cases it can be, but generally I don’t like it. But this idea of looking at a 90 day in the rear view mirror mm-hmm. and asking, put that part of your life on. Yeah. What do you think? That’s a really great question. Yes. Because it covers a span of time big enough that really does look at what are the habits you’ve built, what’s the lifestyle you’ve built?

[00:27:08] Yes. And how are you approaching that journey? Yes. And I’ll, I’ll agree with your comments about pace. The other challenge I’ve seen, Dan, is, you know, even once you reach a certain level of success, you, you think that that’s when you’ll slow down. great entrepreneurs, you know, people who are achievement and success wired like you and me and everybody who’s listening that wants to do this, you’re just gonna set another goal at a higher benchmark.

[00:27:31] Yes. And my wife and I kid about this same thing. You know, I make more money now than I did as an engineering leader, and I have. The opportunity to take more time off now than I ever did in terms of being CEO of my own company. But I often forget that it’s true and I’m I I’ll come home and say, oh, we didn’t hit this milestone, or We’re late on this thing, or, I wanted accomplish this, or We wanna get to this next place.

[00:27:53] And it’s like, whoa, where am I in such a hurry to get to? Mm-hmm. , this is already the life I dreamed about five years ago. I don’t need tomorrow to live the life I dream about for five years from now. I love it. 

[00:28:08] Dan Cumberland: So good. Yeah, so good. When I think, and when you level up, when you reach that place, you also have so many more opportunities the further you go in entrepreneurship, the more you see how much more there is to do.

[00:28:18] Right. And so you have to like, create the habit and again, the mindset of like, , I need to stop. I need to enjoy my time right now. And one, you know, very practical way that I’m working on that is when I tell my wife and kids that I’m gonna be done with work and we’re gonna, and I’m gonna hang out with them, you know, four, four or five o’clock, we’re gonna go do something before dinner.

[00:28:36] Just have dinner together. I need to show up. And I don’t wanna be like, oh, I’m 15 minutes late because I got tied into answering more emails or like whatever else. Like, there’s like one small, one small activity that I’m committing to and working on in my own life and saying, I wanna be there for my kids when I say that I’m gonna be there for my kids and I wanna be the kind of dad that shows up when I say I’m gonna be there.

[00:28:56] Zach White: Love that. So I can’t let you get off the conversation without sharing with us the work that you do now. Yes. That is really a part of the solution to not falling into this trap in the pursuit of simply going after money or flexibility or these things that entrepreneurs dream about. But really connecting deeply to Meaning.

[00:29:18] Yes. And the Meaning movement. Yes. And all of the work that has changed so many lives that you’re doing now. So Dan, tell. You know, what is that meaning movement all about? Yeah. What’s the foundational pieces? And I know we won’t get into all of it today. Totally. We’re gonna need to follow up with you. But yeah.

[00:29:35] I love that. Meaning, where did that come from? And just tell us about it. 

[00:29:39] Dan Cumberland: Totally. Yeah. So the meaning movement came out of, as you sharing some of my story of going to grad school and wanting to like work with people around, like, where are we going? why are we, why am I here? and so, Kind of started in like the, the career space, but more recently it’s focused on entrepreneurs and these questions, you know, avoiding these million dollar mistakes as, as we’ve already talked about.

[00:29:57] So I help help with the meaning movement, the access points, the meaning movement. You go meeting, you’ll find resources there. The podcast is probably the main, the main offering at this point, which, wherever you’re listening to this, you can find the meaning movement. It’s really focused to give entrepreneurs the.

[00:30:11] that we need to recalibrate our work life balance so that we have the energy and motivation to keep going, to avoid those million dollar mistakes, to be able to build a business and a life that we love. I’m trying to like kind of make this Venn diagram of like, , personal support and like business and like, it’s both.

[00:30:28] Dan Cumberland: And that’s some of my lens on life is that it’s always both. And like, we’re not ever, it’s never just business. and so as I’ve been stepping into this and building this building, you know, recalibrating the meaning movement really focused on this demographic, an accelerator that I’m, designing, that’ll be launching, um, in January.

[00:30:46] the, the working title is called Bootstrap Without Burnout. Um, to really help folks, on this path. I’ve got a couple people already committed to this. One’s a, a restaurant owner. One is, owns a, design and strategy. and I’m looking for more people to, to come and, and be a part of this cohort where we get to list these questions together, recalibrate our lives together and have company along the way.

[00:31:08] Dan Cumberland: Yes, yes. That’s a big thing that I’ve seen in these conversations with folks is that often we don’t have the place to, to talk about like this side of entrepreneurship instead. Totally. We have a lot of the strategy, a lot of the business stuff, what about. The, the personal cost and like, who’s gonna help me determine when is enough?

[00:31:26] when have I worked enough and what are the metrics that I need to personally use to measure that in my own life? And so that’s, that’s some of the work that, I’m helping people with through, I love that through the meaning movement and through this accelerator. 

[00:31:36] Zach White: One thing that I share with all of my engineering leaders who I coach Dan, and I.

[00:31:40] It’s so important for people who hear this and they’re interested in what you’re talking about, and they may wanna be a part of the meaning movement with you and join your accelerator. Your mind is a meaning making machine. Yes, and, and you are in the process even as you’re listening to Dan and i’s conversation right now.

[00:31:59] So, engineering leader, I’m calling you out as you’re listening right here, right now, your mind is in the process of making meaning of what we’re saying. You’re deciding if what we’re saying is true or false. You’re deciding if you, if it aligns with your values or not. What you’re gonna do in terms of action or.

[00:32:15] You’re constantly in this process of making meaning, filtering that through your belief systems and your experiences and all of this, and you know, we dig into that really deeply in coaching with our, our clients. Well, the key of what I love about the work you’re doing, Dan, and why I encourage anybody who wants to, pursue this, to work with you and join up with this is you can either let that happen on a.

[00:32:36] On what I would call by default, yes, through a set of filters and lenses that you’re unaware of, and that may steer you right into a brick wall. Yep. Or you can get intentional about creating the meaning that’s aligned with what you want and work with someone like Dan and actually use that as an asset, as a, a tailwind, a catalyst to growth and actually be your superpower rather than.

[00:32:57] S uh, subconscious barrier. Hundred percent. And so, so that said, I was curious, do you have to be a full-time entrepreneur, like running your own company to join your accelerator? Or if an engineering leader is currently employed, but they would love to do this as a side hustle or Yes. Start building their path, is that something they could still do?

[00:33:14] Yes. That is such, that is such 

[00:33:16] Dan Cumberland: a good question. I have not actually thought of it, uh, about it before. I think if, um, if the theme resonates and if this is an area of growth, then anyone, would be welcome. If so, I think it’s like if, if as I’m talking about it, if you said, yes, this is, this is me and something that I could benefit from, would love to have you as a part of it, regardless of your employment status.

[00:33:34] Zach White: Brilliant. Well, I think they need to reach out to you regardless, Dan, cuz you know the meaning method framework, your four pillars. There’s so much meat that we don’t have time to unpack today. And yes, um, so please, please, I encourage everybody listening, go connect with Dan. We’ll put all the links in the show notes and go check out if nothing else, subscribe to his, blog and start consuming this content cuz it’s transformational.

[00:33:55] I had such a fun time going through it in preparation to chat with you today, Dan. So love the work you’re doing. Uh, thank you so much. . Amazing. Well, Dan, you actually alluded to this earlier in our conversation and you know, believe it wholeheartedly that if yes, we wanna get better answers in our life.

[00:34:14] Mm-hmm. . Mm-hmm. , you know, questions lead, answers follow. That’s true. Yes. For great engineering. It’s true for great coaching. The work that you do, you know, this is something that’s a theme in life. So for that engineering leader who’s been with us today listening to this conversation, who really. Better answers in their life, maybe for their entrepreneurial journey or just to get that 90 day window of their life leveled up Yes.

[00:34:38] To that next version of themselves. Yes. What would be the question you would lead them with today? Yes. Yeah. Can I 

[00:34:44] Dan Cumberland: give two answers to this? Absolutely. Absolutely. Because I’ve already already given one question. That question is, if you had to live your last 90 days on repeat, how, how happy would you be?

[00:34:53] And so if that takes you places, and if your answer is like that, I don’t want to like, face that reality, then, definitely, reach out to, to Zach get the support you need. And so that, I feel like has already assumed. So I, I, I’m hoping I get a bye for a second question.

[00:35:04] The second question, which I think is, you know, definitely ties into everything that we’re talking about here, is that. I, the many identities that we, wear, you know, between being, engineer, being, um, mothers, fathers, husbands, wives, all of it. and then we add on top of that, this idea that we’re always growing and like there’s always a new identity that’s emerging in us.

[00:35:26] And so I want to just, again, go back to maybe that, little bit of a woowoo moment I had earlier. Like what. Emerging in you, what is that next identity that might be, forming and wanting to be, to find some expression in the world? And whether that’s entrepreneurship, whether that’s, leveling up your, personal, your mindset you know, and many of the, fantastic things that, that Zach, helps you with whatever.

[00:35:51] Like, inviting people to just do that reflective work of thinking about. , where, where is your growth edge what’s bubbling up and how can you lean into that and get the support you need to go to, uh, wherever that next, version of yourself, is taking you.

[00:36:06] Zach White: Ooh, so good. That is so good. And Dan, I actually think that concept of emergence is not just woohoo. I mean, that’s a very. technology driven concept as well. When we think about AI and machine learning Yes. And how all of the work that so true we’re doing in life creates an unexpected new outcome that emerges Yes.

[00:36:27] From all those interactions, and that is happening in our lives all the time. That’s so great. Thank you for that pause. Yeah, no, I mean, it’s both of, I, I also share a, a strong faith background and as a Christian, I, I love asking that question, you know, from a spiritual sense, yes, but it doesn’t. What background you bring to that question.

[00:36:45] Yes. I think it’s super important to look at all these things on the surface that are happening in your life. Well, as those, bubble up and interact and, and you learn, and this, there’s all these things happening, well, what is being born as a result? that takes some intention. So great question. Yes, great question.

[00:37:02] Thank you, Dan. I just wanna acknowledge you, man. Thank you so much for your generosity. I love, love, love the meaning movement, the work that you’re doing, your podcast. Uh, thank you for your faith. Thank you for your, your willingness to persist through challenging times to be a man who’s, who’s worthy of role modeling and being a mentor and your accelerator, and just keep, keep doing the work.

[00:37:24] It’s so awesome to spend this time with you today, Dan. I love. 

[00:37:27] Dan Cumberland: Thank you so much and I just wanna echo back all of that, and I’m just so grateful that you’re out there helping, folks in your audience, you know, level up their lives and their, their engineering, um, path. Um, so thank you for the work that you do and, uh, all the wisdom you’re putting out into the world.

[00:37:41] So it’s been so fun being with you here today.