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This is your destination for feeling empowered in building your business.
These are the real, raw stories of entrepreneurs and business owners who have built their businesses through the messy middle of $1-20 Million, hosted by serial entrepreneur Matt Tait.
Matt knows what it’s like to scale past the first million, and on this show he’ll be bringing on other serial entrepreneurs and business owners who have been there, done that (or, are currently in it) to share what’s worked, what hasn’t, and what’s next.
Adam Weber [00:00:00]:
I love coaching. Like, I think just as I was leading people, I realized that it's something that I truly loved. Like watching those moments for CEO's realize that how they show up changes the culture and then creating that change like that is powerful. My work is really like helping unlock other people and like, that is the thing that really brings me to life is that. And so they've all been different versions of a similar story, I guess.
Matt Tait [00:00:28]:
I'm Matt Tait, founder of Decimal and fellow entrepreneur. Yes, I'm one of the crazy ones. I've chosen time and time again to hustle my way through that first million. Now I'm scaling to the next 50. So I know firsthand what the messy middle is really like. And I know that entrepreneurs and leaders like us need a destination for empowerment, community and encouragement. This is our place. This is After the First Million.
Matt Tait [00:00:57]:
All right, welcome to After the First Million. I'm your host, Matt Tait, and I am excited today to be spending time with Adam Weber. Adam is a multiple time founder, co founder, founded some really awesome businesses. He's a podcaster, executive coach and author. So bottom line, he's an expert at the messy middle, something that he actually calls the tween stage. So I'm really excited. Adam, welcome. Thank you so much for joining today.
Adam Weber [00:01:26]:
Thanks, Matt. I'm excited to be here.
Matt Tait [00:01:29]:
So before we get started, I like to ask everybody, I think as you know, to run and start your own business, you've got to be a little bit crazy. So when did you know you were one of the crazy ones?
Adam Weber [00:01:41]:
Oh, man, that's a great question. It was about 13 years ago. This isn't something I knew I was going to do. Like, I didn't have set out to be an entrepreneur. I actually thought I was going to do nonprofit work my whole career. Started out as a pastor, I was a musician for a while. Then I got into, like, nonprofit work, was working as an academic advisor, like genuinely entry level job, bouncing around for ten years. I had kids, kind of had a moment where I was like, I kind of want to, like, figure out how to provide for my family a little bit more.
Adam Weber [00:02:10]:
I was putting a lot of pressure on my wife and I got a random sales job and it was for a small business, like 1012 people. And kind of the first day I was like, I'm going to crack the code on this. Like, I'm going to take this one seriously and just kind of set my mind to it. Really kind of initially started with, like, trying to master sales, and first year I had the best year that company had ever had, you know, a small business. But still, it was, like, significant to them. Second year, doubled the revenue, and they were like, this is awesome. And I was like, I wonder how long I'm gonna make money for somebody else. Like, I wonder if I should do this for myself.
Adam Weber [00:02:45]:
Total happenstance. How I got into entrepreneurship, though, is I wrote a blog with that sales job about my first hundred thousand dollars deal I closed, and this kid in college read it. Santiago is his name. And he sent me a cold message on Twitter. He was just like, hey, can I grab coffee? I'd love to learn sales from you. And, you know, it's wild, that first coffee. I think we both just, like, knew that there was some natural connection between us. We were joking.
Adam Weber [00:03:10]:
He and I were actually on a podcast together yesterday, and we haven't worked together for almost three, four years. But it was like co founders at First Sight. Talk about being crazy. Imagine having two kids, having already had that ten year start to your career, and now you got a 21 year old in your family room who has one, one or two clients selling you and your wife on why you should join him. Right? He walked out of the house that day and kind of pitching the business plan, and my wife was like, if you don't do this, you're going to regret it for the rest of your life, you know? And so we just took a huge leap of faith when our boys were three and four. That's basically how I got into entrepreneurship.
Matt Tait [00:03:46]:
I really like that story for a couple of reasons that really resonate with me. Number one, I think so many times people think that to be a first time entrepreneur, you have to be in the, like, de risked phase of life. You have to not have kids. This is the time to do it. But you did it the other way around. To be fair, I did, too. It wasn't until I had kids that I decided to be an idiot and start my first business. But I really like that because it's very different from the way people think.
Matt Tait [00:04:15]:
Although statistically it's about equal. People start their first business at various phases in life. The other thing that I find is hilarious. My co founder, Jacob, and I have worked together, and I'm now 40, and we first started working together after he spent a year at IU and dropped out. I also have a co founder, a long time second business that we've worked together with who is, well, keeps me young. So I think that's really cool. So you and Santiago started a business. Tell us about that.
Matt Tait [00:04:48]:
Because it actually became more than one business, didn't it?
Adam Weber [00:04:51]:
It did, yeah. Our first business was called Bluebridge. It was a mobile app development company. I remember we built this business plan our first year. Our goal was to have 32 customers. And at the time, think of it like squarespace or Wix, like an easy way to build, but it was an easy way to build mobile apps, and it just grew fast. Like, we went from those two customers to over 100 customers in our first year, and the team scaled really quickly. We were up to probably close to 30, 25, 30 employees at the end of our first year.
Adam Weber [00:05:20]:
And that was also where I started to realize all my own kind of leadership gaps. And there's aspects of it that was like, I am thriving. Like, finally I'm challenged. Finally I'm stretched. I'm not just passing time at work. I'm, like, recognizing some of my own abilities that I just hadn't really had to use before. And they all started to come out, and that part was a blast. Then the flip side was, like, I was just a super clunky leader as a people leader and how to really motivate people or how to guide them, because to get to that spot, I'd been so used to just, I'll do everything I can figure this out.
Adam Weber [00:05:56]:
And then you have to go from that to leading people, that sort of thing.
Matt Tait [00:05:59]:
Most of the time, businesses have time in that startup phase, and that's also where you grow a little bit. But you guys basically accelerated through the startup phase into the, like, we got to build a business into that messy middle pretty much overnight.
Adam Weber [00:06:16]:
It sounds like overnight now that it's been years later. At the time, it felt like an eternity. You know, those first six months where I was cold calling by myself every day and, like, trying to figure out how to get customers. But it would have been, like, three or four months before I got my first yes. And I remember I would make 50 cold calls a day, every single day. I made my wife. Cause there's, like, nobody to hold me accountable. At the beginning, I said, I need you.
Adam Weber [00:06:39]:
I want this so badly. Like, I don't want to go back to this entry level job world again. Like, I want this. And so I was like, every night at dinner in front of the kids, ask me how many calls I made. I can't guarantee this is gonna work, but if it doesn't work, I don't want it to be because of my lack of effort. It was like that for a little while, but then once it got rolling, it really kind of took off pretty quickly.
Matt Tait [00:07:00]:
You mentioned that you were a clunky leader. It was also your first kind of managing people job. You're also in that balancing of, I have to do things, it's my job to sell, it's my job to make money, but also manage. So you're in the and world of startups as well as, you know, at some point you looked and you had 30 employees and you're like, okay, we should probably have like HR processes. Payroll is a good thing. How did you kind of balance that? You mentioned clunky. Why unpack that a little bit?
Adam Weber [00:07:32]:
I think the clunky part was a combination of two things. One was not having my own sure footing and who I was as a leader. And so then I would just like take advice from other people and try to apply it. Exactly. Especially the sales side, which is where I started. That was one part of it was kind of like trying to apply these like either tactics from a bad manager I'd had in the past or just some training that I didn't do what I call the work of translation and like make it my own and like do it in a way that is like my way instead of trying to just follow a textbook. And then the other is that I just wanted it so badly that at times the pressure and stress of it got to me and then sort of manifested itself toward my team. And I would say those were some of my moments where it's amazing that original team of four or five who I like, dedicated my book to, they taught me how to lead, you know, and they're so great.
Adam Weber [00:08:28]:
I'm still great friends with all of them, but they all saw that other version of me as a leader and then helped me grow and become a leader, too. But, you know, there'd be moments where the one that stands out the most was like, end of the day on a Friday, everybody. We did a stand up to kind of share our work for the week I came in. Triggered before it started, I was like in a bad place. I was stressed about probably like the business's finances or whatever, and I wasn't impressed with how people did for the week. I'm sure they were probably all trying super hard, you know, but at the time, it just didn't land with me and I like lost it and I stormed out of this meeting and we had concrete floors and I had to walk like 40ft, so it echoed. It was like the most long form, embarrassing stomp out of a meeting ever. By the time I got to that door, it was so far away, I'm trying to storm out of this room.
Adam Weber [00:09:18]:
I was really embarrassed. And I also realized that something wasn't working with how I was, like, leading people. And so that weekend, I kind of had a bit of a heart to heart with myself, and then came in that Monday and had a heart to heart with my team. And I do think that was kind of the very start of me leading people in, like, a way that was more true to who I was and just kind of finding that balance of, like, you're this person who sits with people and who makes people come alive, and you're really gracious and friendly and funny and all that. And then for some reason, inside of the confines of management, you're flipping into this other person. And so I kind of, like, just shared all that and said, hey, I want to be my regular self with all of you and be the best leader I can, but also do it in a way that's me. I feel like they saw that, like, 50% of the time, and, like, they knew that that's who I was, too. And in some ways, I think part of why it worked was they were all like, we're going to hold you to it.
Adam Weber [00:10:08]:
And I think they did. And I think that's probably why I'm so close with so many of them to this day.
Matt Tait [00:10:13]:
So that first year was kind of your figure it out kind of rough. Tell us the Bluebridge story.
Adam Weber [00:10:19]:
I don't think we knew we were exactly at the time, but we were kind of growing two separate companies at the exact same time because we had two markets, we were selling to cities who would buy the app. It was kind of like a yelp, but the city paid for it, and it'd tell you where to eat, what was on the calendar of events, that sort of thing. And then we also sold to these, like, churches that had, like, a calendar of events, et cetera. It was the same product, but we had two markets and all that. And as we started to grow, the business started to get a lot more complex because how you sold to each of those markets was very different. So then we had to start splitting the branding, and then we had to start splitting the sales team, and then we had to start splitting the territories. And, like, everything as it started to grow, and they were each growing at, like, the exact same pace, I mean, almost identical. It created a little bit of complexity because we were kind of growing two separate companies at the same time with shared services, I guess, in the middle.
Adam Weber [00:11:09]:
So we did that for a couple years, and we had some pretty decent success with both. We had ambitions to grow a really big company. Like when we started, we really wanted to grow like a huge company. And we kind of ran into this issue with both of those two products. There's only 1500 cities over x number of people and there's only 800 churches over 1000 or what? You know what, I can't remember the exact numbers, but basically like, and we'd already taken up 20% of the market in our 1st 18 months. And we're like, where to? And that was part of it is we just, we picked, maybe a good lesson for us was like, we just picked too small of markets really originally.
Matt Tait [00:11:49]:
So you're growing two companies. What was the end, end of the story for Bluebridge?
Adam Weber [00:11:54]:
Yeah, well, it actually ties into Emplify because those two companies, we'd been like, well, we want to get bigger than these are going to allow us. So what's a third one we can start that will get bigger? And originally it was like, well, let's just take this exact same product and sell it to companies. And keep in mind, this is before slack. Honestly, it wasn't even that good of an idea then, but now you're like, that's the worst idea. But it was basically like a custom branded mobile app for companies that held the company core values, where they could send push notifications to employees for like the most critical stuff, an employee directory, that sort of thing. We kind of built that as the third product. The wild thing is it did great. Those first two products got to a million in recurring revenue.
Adam Weber [00:12:38]:
It took two and a half years, maybe roughly that 118 months. Like, it was fast. Like, it happened like really quickly. And at the same time, I guess just to kind of close the Bluebridge chapter, we started to realize that that's kind of an endless market. It's a big market and big opportunity, and now we're accidentally running three companies at the same time with a different logo and a different brand and all that. And so what we did then was we sold Bluebridge Tourism to one company and we sold Bluebridge churches to a separate company, both on the same day. Then we were kind of off to the races with Emplify.
Matt Tait [00:13:17]:
Part of you is focusing on Emplify. It had to feel good to sell the other two just to be able to give you the chance to focus. But at the same time, those are your first two babies. How did it feel to kind of go through that multiple acquisition phase? Or were you even able to actually experience it because you were still pushing hard at the. The third one, Emplify.
Adam Weber [00:13:40]:
That's a great question, because I feel like my, like, acquisition let down moment or, like, processing all took place with the Emplify acquisition more than the Bluebridge one, because with Bluebridge, it was interesting because it was like, we sold them, and then the next day, we kept all the employees. So we basically had this smaller startup, but we kept our employees. We could grow really quickly, and we were just more focused, you know? And so, I mean, there was, like, a sense of accomplishment. It was one of those things where you're like, this is, like a notch that we'll get to have and keep and, like, know that we did something, you know, something of value in the universe that, like, meant something to people. And so it was that. But it definitely also was like, we did it because there was a bigger opportunity in front of us, and it was, like, time to go. There wasn't a lot of recovery time. The next day, it was like, no days off, no weekend.
Adam Weber [00:14:28]:
It was just kind of like, and we're back the next Monday.
Matt Tait [00:14:31]:
Decimal is my third company. Every time I've turned the page on one company, it's given me the ability to actually stop, think, learn, apply. Were you able to do any of that? You mentioned initially with Bluebridge, you were a clunky manager. Did you have the ability to apply things and be different with Emplify, or was it really just an extension of Bluebridge?
Adam Weber [00:14:57]:
It. It.
Matt Tait [00:16:34]:
I like to focus on culture and having a remote company as a different beast. When you focus on culture, I always joke with friends of mine that are running growing companies with an office that you can lazily build a great culture. When you have an office and are around everybody, when you're remote, you have to be much, much more intentional. But I can't imagine how much more that's true. When you're running a culture company, you have to be that kind of glass house on the hill, don't you?
Adam Weber [00:17:03]:
I think rightfully so. Like, it was a bar that I liked to set. I liked that myself. Like, I want to be a world class culture that. And I started sharing all the things we were doing, like, openly. That was, you know, on LinkedIn. I'd be like, here's a new thing we're working on. And I started to get into the world of, like, I have to be super transparent.
Adam Weber [00:17:20]:
It's just the nature of what we're doing right now. And there are certainly moments that were really hard. If employees wanted to make a statement, it's like they just have a lot of power, because it's like, hey, this is what we say to other companies. How are we not living this out ourselves? You know, that sort of thing.
Matt Tait [00:17:35]:
You know, one of the things I've found in going through the phases of business, and I'm interested in your thoughts as you think of the. The beginning of Emplify. You mentioned I each company, you were able to kind of speed it up a little bit at the beginning. What I found in going through it multiple times is part of that is because as I've gotten deeper into that messy middle of having to actually build processes and efficiencies, it's helped me pull them forward quicker. When my first time, it was just kind of go do learn, kind of clean up the road behind you a little bit. But is that kind of what you all learned and did a little bit with Emplify, was able to pull some of that scaling, that ability to scale forward and apply it quicker to help you grow faster?
Adam Weber [00:18:21]:
That's a perfect way to summarize it. There's a learning tax where you're kind of learning how to do the thing yourself, and it takes you a long time to even figure out what the answer is. There are things that I figured out on my own, only to find out later is like, this is an industry standard best practice. Just spent three months trying to figure out how to crack the code on outbound cadences or, you know, whatever it may be. It could be anything. But we already have some systems in place that are just working, and so let's just, like, change the language and then put the new system in place, that sort of thing.
Matt Tait [00:18:53]:
The amplified journey doesn't end after that first year. Tell us a little bit more about that journey in that company.
Adam Weber [00:19:01]:
As I mentioned, it kind of started as that mobile app. We wanted to get into this employee engagement market, which was really a growing market at the time. And simultaneously, we're realizing, like, wow, we all really are good fits for this market. Like, this topic. Like, we have a great culture. We're really passionate about engagement. One caveat is that our product actually doesn't help the industry we're trying to break into. And so we were like, what if we actually could meaningfully make a difference to create better cultures for people? Like, highly engaged cultures? And so while we were selling that mobile app, we kind of had a little tiger team spin off, like, kind of demystify what engagement was, did a lot of research, built our own survey, and then originally it was just like this survey on surveymonkey that somebody would read the results to.
Adam Weber [00:19:49]:
And we kind of demystified what it meant to create a highly engaged culture, what made people motivated. And then we'd meet with the CEO and just talk them through it. That was the moment where it's like, this is actually how you build great high performance cultures. And so from the get go, our very first idea been the one that was our last idea, we would have had a very different outcome. Right. That's not how it worked for us. We started, we stopped, we started, we stopped. You know, at that point, we realized we were really onto something that lived out the promise that we were after, which was, like, to help improve employee engagement.
Adam Weber [00:20:19]:
And so we turned that into a product. Right. An easy way for employees to give feedback, a dashboard that people could, like, actually understand their culture, and then this kind of real time coaching for executives to tell them with data what's going on inside their culture. So basically sunsetted the mobile app, moved everybody over to the measurement tool, and then the measurement tool is the thing we did the very longest. We did this employee engagement measurement concept for probably three and a half, four years before the exit.
Matt Tait [00:20:50]:
Let's fast forward to the exit. So you built the company for three or four or five years. It's growing. What made you guys kind of reach a point where it was like, all right, time to be done?
Adam Weber [00:21:03]:
So three or four years, that measurement part, but everything I just shared total, just to give everybody some anchor on time. That was ten years, maybe nine and a half. So from that Bluebridge conversation to that. Right. So it's just a lot of start, stop, start, stop, but same. Sansi and I did the whole thing together. Two things happened. One, COVID happened.
Adam Weber [00:21:21]:
And when COVID hit the kind of employee engagement measurement space, started to get gobbled up by hub solutions. So we were in a really tricky spot. Like, basically, we had to decide, were we going to create a kind of industry specific niche product, which we haven't been so far, or are we going to exit? Did we have the energy to keep doing this? And I think we ran out of gas, and we kind of had this perfect scenario that played out for us, which is just so grateful for that. One of our customers who used our product forever and, like, loved our product a couple years before, they'd called us and been like, hey, would you ever consider joining us? And we're like, we threw out a ridiculous number. And they're like, nope. And it was so cool. Imagine a CEO calling you to ask that and then saying, I just want to be straightforward with you. We're going to build a competitive product.
Adam Weber [00:22:08]:
So we had a ton of respect for them all along. They went and tried and realized how hard it was to build this product. It was really hard. Right? And then they came back to us. We'd been using their product, they used ours. We always kind of considered ourselves brother and sister companies, and so it really worked out. It was just really fortuitous, I guess. Like, our energy was fading, our path to, like, victory wasn't super clear.
Adam Weber [00:22:30]:
And then this kind of soft landing for us came and we jumped at it.
Matt Tait [00:22:34]:
You just mentioned that a big piece of what Emplify became involved, kind of executive and CEO coaching. You kind of started your career in the nonprofit world. You then went into sales, but ultimately, did you kind of find your personal fit in executive coaching? Is that what led to where you are today, or was that just kind of a seed that was planted that took some time to grow?
Adam Weber [00:23:03]:
It's somewhere between I've been quietly building toward this, not realizing it my whole career, and something that, like, it's happened. Like, I think just as I was leading people, I realized that it's something that I truly loved and part of implify, like, watching those moments for CEO's realize that how they show up changes the culture. And then creating that change like that is powerful. I also think in my own personal life, I love helping people become the best version of themselves, see what they're great at, find that thing that maybe they don't even see in themselves, and then help them, like, bring it to life. Like, practically, not just all kind of up in the clouds, like, actually, how can you do this? And so it's been some combination of that. And that was what was so beautiful about, I guess, the end of implify. And then even the 15 five acquisition was like the last two years of emplify. I had this moment.
Adam Weber [00:23:58]:
I went on a founder retreat. It sounds as foundry as you can imagine. It was out in the middle of the woods. And I kind of realized though, out there I was like, my work is really, like, helping unlock other people. That is the thing that really brings me to life is that. And so they've all been different versions of a similar story.
Matt Tait [00:24:14]:
I guess it's interesting for me because I empathize a lot with what you're talking about. One of the joys I find in my role as CEO is unlocking my team and being able to help them grow towards and even exceed their ceiling. And one of the things that really unlocked it for me and you've seen this during the time those of us that led through the pandemic. That's in some ways a trauma that we're going to spend decades unwinding from. But one of the things that it really unlocked for me, and I think for a lot of people, particularly those of us, like kids of the eighties, particularly menta, I wouldn't say that, like, vulnerability and emotions were something that I grew up thinking about or doing very much at all. But in the pandemic, there was something that just got that veil removed, and it was that CEO that who you show up as doesn't always have to be happy, but authentic. And if you're feeling bad, if you're having a rough day, if you're struggling with something, it's okay to talk about that. It's okay to be who you are.
Matt Tait [00:25:24]:
And you have to be careful on how you deal with that outwardly and how you're transparent, but you can still be transparent versus you don't have to hide from that. Is that something that you kind of found in either your personal leadership or in your coaching as well?
Adam Weber [00:25:42]:
Yeah. So in my book, there's a whole chapter on this concept of centeredness. Right. The whole concept of the book is, like, how do you lead as your authentic self, but in a way that drives performance for the team? Executives live in this tension of, like, I wanna build a great culture. This isn't a nonprofit. We need the company to perform. Yeah, we gotta win. And so we live in that duality.
Adam Weber [00:26:04]:
And, like, part of that stomping out of the room moment, right, that I was shared earlier, it's like, I realize, like, what are the disciplines? What are the habits? What are the changes I need to make in my life that allows me to show up in a calm, steady, consistent way, because I do think authenticity is really important. But I also don't think just showing up however you want to show up is super valuable. Like, having agency over how you show up to your team is a learned skill as well. So if you're heightened and super stressed and all that, and then your employee talks to you and it's, like, natural for you to lash out at them, that doesn't mean it's the best thing for the team, right? Like, what creates psychological safety and, like, a great team is someone who has an emotional regulator who can be real but who also can be consistent. And so, yeah, I'm the middle of starting my own thing again right now. Like, from scratch as this is coming out. Like, I'm still in the early. This is my first full week, kind of expanding my executive coaching practice.
Adam Weber [00:26:58]:
Right. And, like, it's interesting. Like, I've done all that stuff in the past, and yet still I woke up this morning just, like, feeling that anxiety of, like, what if nobody believes in this? It's all the same stuff that I was telling myself ten years ago. Right. So I go back to those same disciplines, and I know everybody's different, so I'm nothing. I don't want to speak for everybody, but it's like, I journal. I sit down in the morning, I try to write out, like, how I'm feeling. I try to read something timelessly true that kind of roots me in a moment that's bigger than, like, this one moment to remind me, like, you've done this before, like, you were meant to do this work, those type of things.
Adam Weber [00:27:30]:
And then I go on a walk. It's nothing overly complicated, but it's amazing that, like, it's a discipline. I put that in place because what you're doing right now is not easy. You're carrying a constant weight. It's hard work. And so those disciplines, for me at least, have been super helpful.
Matt Tait [00:27:46]:
I'm a big proponent that if you are the leader or CEO of a growing or big company, I think you need three things to be successful. Number one is focus on your own personal and mental health. And that looks different for you. It's the journaling, it's the reading. Something that's timeless. It's the walk. For me, it's a workout. It's meditation.
Matt Tait [00:28:08]:
It's some other things, but having whatever your own personal and mental health, having that locked in, also understanding that as time goes on, things will change and being willing to adapt. Number two is finding a peer group, some group of people where you can learn and talk and be free to do it, because as your team grows, your ability to have some of those conversations about your own inadequacies, about your own anxieties, about even some of your joys, you stop being able to do that entirely, even with your co founder. And then the third is a paid coach, somebody that you actually pay to talk to and give advice. And I have one. You are one. But I think that that encapsulates to me all the things you need to be successful as a CEO. Yeah.
Adam Weber [00:29:00]:
And when you said that on the first call, I was like, that's, like, really, really good. Like, I really think that you nailed it. On that peer group, it's really easy to think that the stressors you're facing are unique to you. And there's something that happens with the peer group that normalizes the challenges. And as soon as you normalize the challenge, it sort of deflates the stress balloon a little bit. I'm not the only person in the world who's dealt with this or sometimes that learning tax that you're paying as you're growing. Like, the person's like, hey, I just did that. Here, let me just share it with you.
Adam Weber [00:29:30]:
Part of why I knew that I wanted to be a coach was because of the impact that coaching had on me. There's this component of, like, having a person who will tell you the truth, having a person who will kind of be real with you about how. How you might be showing up or where you can explore these aspects of yourself, like leadership. The part that doesn't get talked about enough is how, like, it basically brings up all your childhood trauma. Like, all the stuff you hid away. Like, there's a reason why you got an entrepreneurship, and it was to basically block yourself from whatever you were scared of as a kid. You know, it's always there under the surface, and it's valuable to explore, to, like, actually grow, and it makes you a better person, which is what's so cool. I feel like I'm a much better person because of how I got pushed through the growth and stress of entrepreneurship, but then also through coaching.
Adam Weber [00:30:21]:
And the other one, though, for, like, a CEO, is that it's amazing what happens when you give a CEO an hour for themselves. Like, that's why I love coaching, because I've been on the other side. I've been taking in all these inputs. You have to make these decisions. You start to spin and swirl a little bit. You almost can get paralyzed on what's next. For me, it's like, I meet an hour every other week with my clients, and it's like, it's borderline sacred. What happens when you just let a CEO talk or an executive talk and just, like, listen and then summarize back? And, of course, there's other moments where there's challenging or collaborating, but, like, sometimes you just need space to explore.
Matt Tait [00:31:00]:
Well, and I think a big part is when you're constantly fighting through a problem. You don't have the ability to rise above the problem and look at it from a different perspective. And the peer groups, the coaches, they give you the ability to just kind of rise above it and look at the problem from a different perspective. And that, I think, is such a key thing in being a CEO. And if you start a business you're the type of person that always sees the light at the end of the tunnel. You think, I will do it. I can do it. But sometimes that light feels very small and very far away.
Matt Tait [00:31:35]:
And what I like to tell people is coaching and peer groups. Those are the types of things that can make the light bigger, bring it closer to you in ways that you couldn't or would do slower yourself.
Adam Weber [00:31:47]:
You're the host here. But I am curious, though, because you've done coaching, like for yourself, like, how do you think you've grown the most yourself since you've done coaching?
Matt Tait [00:31:56]:
I had a coach, and my coach has been doing it since 1980, since before I was born. He has been coaching people that are way cooler than me, and I really like that. He has a database program that we started with a full 360 degree analysis of me from my own perspective and people that had been in my career dating back ten years. I mean, people were amazing. They went through a 45 minutes test and analysis about me. And what that did was that helped him understand what some of my flaws were that I wasn't seeing. Also some of the things that I was really good at that I struggled to recognize having rich, my coach, having that type of center point to help understand my flaws. There's one good example.
Matt Tait [00:32:46]:
I had a coaching session yesterday, and we were talking about how personally on my one on one, I am very much the opposite of a conflict avoider. If you and I have a problem, I am going to sit there, I'm going to talk to you about it. We're going to figure it out. We're going to move on. But when it comes to other people and other people's conflicts, I am a conflict avoider. If two people on my team are having a. An issue, I had a tendency to say, go figure it out. Well, go figure it out is code for I'm avoiding this conflict and don't want to deal with it.
Matt Tait [00:33:20]:
Go do it. And realistically, people on your team don't do it. And so you've just avoided everybody's conflict rather than stepping back, creating a safe space, giving them a chance to solve the conflict themselves, but then also being willing to create that safe place to solve it. And that was something that was just mind blowing for me because to think that I am was just kind of earth shattering for me. And then it made me seriously sit down and rethink who I was. And I think some parts of being a good leader, it's not just being transparent with other people, but it's being transparent with yourself, see who you are, what your flaws are, what your good parts are, and recognize and be willing to talk about all of them. And that's what I found rich has been very helpful in, is that he's been coaching me for over two years. And so it's a, it is a well worn shoe at this point.
Adam Weber [00:34:19]:
What a great example, too, of like, how you've kind of identified these aspects of yourself and then shown up, too. That's awesome.
Matt Tait [00:34:26]:
Let me flip it on to you. You now coach and have been coaching people for a while. What are some of the things and some of the stories that you've learned in not just your dealing with the messy middle, but coaching people in that messy middle?
Adam Weber [00:34:42]:
What's interesting is how many have naturally come up with what we've just shared today. There's one that I think I see time and time again, which is a lot of people who start businesses are starting it because they have this dream of the future, of what their life will be like when it's over and how many of those things you can actually pull forward right now and start living the life that you want to live. So I would say that's one is like, what are you delaying? Like, what is that thing that you're working for down the road and how can you begin to live that life today? I think that comes up a lot. You know, it's interesting. Like you said, you're like, not a conflict avoider. There are a lot of conflict avoiders. Maybe there's a known conflict, but it's like the second biggest conflict. And so it's kind of like, eh, that one's for later.
Adam Weber [00:35:28]:
And so there's kind of like the two ends of the spectrum. There's the people who lean in too much to conflict and it stifles progress. And then there's the people who are avoiding conflict. And it's like just a problem that needs to be, you know, something that needs to be said today. Oh, yeah. I do think the very most common thing is when a problem feels so big, it makes your world feel small, like you can't see outside of that problem. The stress supersedes your judgment. That is like something that is very common for someone that's, that's just leading.
Adam Weber [00:35:58]:
It's not unique to someone in coaching. It's unique to human beings who are trying to lead companies. One other one I was just thinking about before this call is that I think oftentimes CEO's and leaders of companies forget when they're making a big decision. That they've had, like months to ruminate on the decision, and then they enact it and then immediately are frustrated that everybody else isn't, like just jumping out of their seat, super excited about it, even though they had no time to ruminate. And, like, that's really common where it's like, I'm really frustrated at my team because this thing, that's obviously the right decision, and it probably is. It's just that how do you actually get people on board with your vision, with this thing that you've really thought about? And how do you give them space to process, too?
Matt Tait [00:36:43]:
You know, it's funny you bring up two things. I've been talking a lot about socializing decisions before you make them. We're getting ready to go through some changes at decimal, and luckily, by the time this podcast comes out, we'll be deep in them, so this won't shock anybody. But I talked to the team and I talked to the managers that are going through, and I say, I want you to go have one on ones about people, with people, about this topic. And once you spitball it, give some ideas, socialize it. I've already done that with my direct reports, with the people, even below them. But socializing a decision and getting people's input before it becomes final, before that presentation, it was something I talked to our director of Ops, Nicole, about. I said, look, big presentations are really a terrible place for people to hear about things.
Matt Tait [00:37:27]:
The first time. You should go into any room and put yourself in a position where everybody has heard about this beforehand and give them the space to then process it together because they've also had the space to process it separately. The other thing that I think is really important, that in a growing organization, and this is my big kind of q two Q three theme right now, is creating space. And I think space is such an important thing in that messy middle that you can struggle with where you have to create space for you to relax. You have to be able to take time off. I, for the first time in embarrassingly long, turned off my phone during spring break for two days, creating mental space for me to just detox. But the other thing is creating space for people to do things. When you grow an organization so fast, people are so busy and you assume that they can continue to do their jobs while also institute change.
Matt Tait [00:38:24]:
And if they don't have the space to do it, it's never going to happen. And you have to just think of space as a moving part of any organization.
Adam Weber [00:38:33]:
I think that's so good. It's interesting like this. How do you rise above, right? Like, how do you kind of get that higher order thinking? This is why I go on walks. It's the same thing. I don't bring my phone on walks with me. And I know it's not two days, but it's like 30 minutes walk with no access to technology. Like somehow in the middle of it, this problem that I've been ruminating on forever just disappear. It's like, oh, okay, I see it differently, you know, or, you know, you can just, just simply being overstressed can make simple things feel hard as well.
Adam Weber [00:39:03]:
But that's great. And I also want to go back to your comment on, like, a big company meeting is like the worst place to learn something new. I love that so much because human beings are just averse to change, period, right? It's like, it's hard and your natural reaction is to resist. And so it's like I'm always like, nope, I'm just going to trickle stuff out, float it out, get some advocates. I had a couple people that were like, people that have naturally adverse reactions or who are really critical. Instead of viewing that as a negative, I go, they definitely are going to see something that I'm not seeing right now. And so I want to go to them first and I want to get their feedback about what's wrong, about what I'm about to share with the.
Matt Tait [00:39:41]:
They will probably improve what you're going to do, right?
Adam Weber [00:39:45]:
They do improve it. And then when I roll it out too, I also reference them knowing that everybody already knows these are some of the biggest blood, you know? So now that person's on board and it just, it makes the whole thing so much smoother. One other thing just thinking about too, just like, came to me with what we were talking about. Like, the reality of, like, growing a business, especially if you have a family like, you and I are both dads in the middle of, like, raising kids and everything too, is that it does take discipline. Physically being present at home versus mentally being present at home is like a really important aspect, too. That's like worth a conversation, you know? I remember when I allowed myself to get overstressed. Yes, I'd be at dinner with my kids or I'd be at the soccer game, but was I there? And I do think when I'm really there, it's like, who, what I want my life to be, you know? But it can take some discipline with when you're in those really either heightened stress times and also honestly, the really exciting times too.
Matt Tait [00:40:39]:
I really appreciate you coming on. I have one last question. This is going to be a great tag for your coaching business as you think about all the coaching you've done, as you think about your experiences. If you could give one piece of advice to CEO's and leaders going through this messy middle, what would it be?
Adam Weber [00:41:00]:
I think, like, what used to be organic and what used to happen really naturally for you. It's okay to take the goodness of that and put some scalable processes around it as well. But just because you're adding those processes doesn't mean you're like losing that goodness of like what you'd originally created. You're simply allowing that vision that really come to life. I think that's like, tactically what I'd say to somebody who's in the messy middle, like as far as like for their company, I think for themselves. Whether it's a walk, whether it's two days, whatever it may be, don't delay the life that you want in your personal life. There's nothing that is worth sacrificing your very being with. Because once the business ends, you are still with yourself.
Adam Weber [00:41:43]:
And so just make sure you're like good to yourself as you're on this journey too.
Matt Tait [00:41:47]:
I love it. Well, Adam, this has been an awesome conversation. I really appreciate you taking the time.
Adam Weber [00:41:53]:
Yeah, thanks, Matt. That was great. Thank you so much for having me.
Matt Tait [00:41:57]:
Thanks so much for listening. After the First Million is presented by decimal, to listen to more episodes and find tips to help make running a business easier, visit decimal.com/afm. Want to join the conversation? Reach out to me on LinkedIn and let's explore the messy middle.