97. I Lost $500k in Revenue (And Made it Back in 62 Days!)
8 Dec 2025 · 19 min
A founder lost $500k in recurring revenue when a key team member left, then rebuilt it in 62 days. He shares what actually worked: finding mentors, learning specific skills, cutting noise from his feed, and writing daily to stay clear.
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Foreign.
Welcome back to the CFO report. Boy, the last 12 months have been filled with so many blessings for me and my team. We've accomplished so many things. But frankly, I'm not here to talk about that today. Today I want to talk about some of the specific things that have happened to me or for me, depending on what kind of mindset approach you have over the last year. That in a lot of ways, in the moment, I felt like these things were conspiring against to make my year an absolute dumpster fire. And the reason that I think it's so important to talk about this today is there's so many people out in social media and on YouTube and on podcast and in our social circles, they just talk about the win, win, win. You know, like, everything's going great, nothing goes wrong. And it paints this picture of perfection. And if you're anything like me, when you constantly see these messages by people that are just doing great all the time, and then we encounter difficulties in our own lives, we start to think maybe we're the. Maybe I'm the idiot that just doesn't know how to business the right way and that's why I'm losing clients or I'm having struggles with this or whatever the thing might be. I'm gaining weight or I'm not losing weight, or I'm having trouble in my relationships. When we see these pictures of all these other people that are just winning all the time, we can tell ourselves this story that we're not good enough or that we don't belong. And so today I want to share those specific things that were just punches to the face face last year for me in terms of business and in my personal life. And after I kind of go through this list just to give you a sliver of hope that you're not the only one that's facing challenges and problems and missed goals and all the things in life. I also wanna share with you some specific mindsets and actions that I take to help me navigate around or overcome these challenges that inevitably come up in the world. So without further ado, let's dive into hearing about the dumpster fire. Things that happened to me last year, and right out of the gate last, one of the first things that came into my business world was this realization that I had to fire our social media manager. She was a great person. She was liked by the team. But what we realized as a result of eos, the entrepreneurial operating system that we use, is that we had a wrong person on the bus situation. Great person Just not getting it done in that role. And so I had to start off the year by letting somebody go on the team that by and large the team actually liked working with. This was a nice person, great values, great personality, all those things. But it was very clear that she just wasn't right for the team. And so, boom, January 1st, right out of the gates, got to let somebody go. That's never, never easy. In addition to that, throughout the last year, I saw my closing rate for sales tank, I mean absolutely plummet. Historically speaking. Out of every 10 sales calls or so that I get on, you can pretty much bank on me closing 7 or 8. So my close rates around 70 to 80%. Historically. Last year I found that sales rate or that close rate plummet to somewhere between 10 and 20% for the vast majority of the year. And so you start seeing, you know, lead after lead, say no. For various reasons in the man, the self talk, the doubt, the confidence, it really can kind of get inside your head and just the stories that you start telling yourself, I was lucky before, I don't have it anymore. Maybe I'm not the right person for this. Business needs change. You start to wonder, do you have what it takes to bring in new revenue and to not just grow the business, but to sustain the business? Like I said, this was a period of like seven or eight years super, super demoralizing and frankly depressing. A lot of times laying in bed, not able to sleep and just again, the self talk. I don't know if you're one of those people that does the self talk, but man, it was really toug tough for me last year. In addition to struggling to bring in new business for a season, we also had some clients fire us last year. I mean, there's no two ways about it. There were quite a few reasons that that happened. Our onboarding process needs an overhaul. We realized that onboarding was taking entirely too long in some cases. We recognized that we weren't doing a good job of connecting our clients goals to the strategies and the tactics that we were suggesting. And so there was this chasm that started to develop between where they needed to go and what we were telling them. They just couldn't connect those dots. And it resulted us in us fired. And gosh, tens of thousands of dollars went out the door because of poor onboarding and our failure to do a great job of connecting tactics and strategies to their goals. And then as the leader of the organization, I realized that I had done a poor job of setting the expectations and coaching my team. Around how to do that. And so again, the self talk and the stories and all the things, they start to really fill my mind. And it just makes it hard sometimes to get up and come to work every day. And so you take that, the fact that close rates are down, we had some clients fire us. And then, you know, towards the end of the year, I had a team member leave and overnight over $500,000 in recurring revenue walked out the door literally overnight. Half a million dollars, over half a million dollars in recurring revenue was, was just gone. And you have this realization that in a lot of ways a fractional CFO firm is, is kind of like a law firm in that client loyalties in a lot of ways are tied to the fractional CFO and not to the firm. And so, man, I found myself in late Q2, almost into Q3 last year in this situation where revenue dropped almost to the level that the business couldn't sustain. And so, boy, the fear that comes up in that moment, the uncertainty, the doubt, you know, I've got people counting on me to pay their paychecks. Am I the right person to do this? How can I let this happen? Oh my gosh, oh my gosh, oh my gosh. It's hard. It's really, really, really hard. And then on the personal front, a lot of you know that last year my wife and I adopted a 10 year old boy. He's a fifth grader. And shortly after he came into our lives, we realized he really struggles with math. And in a lot of ways, or by a lot of accounts, he's somewhere between a year and a half and two years behind where he should be. And boy, I'm realizing there's this human being that's counting on me to guide him and lead him and love on him and getting caught up to speed on math. And I haven't even looked at math in like, I don't know, 20 or 30 years, much less. Like I've never tutored math before. And I don't know how old you are when you went to fifth grade, but I'll tell you, like, math today in fifth grade looks nothing like it did when I was in fifth grade to however many years ago that was. And so again, like I find myself in this situation asking myself the question, do I belong here? Am I the right person for this? How am I going to help this, this person that needs my help out of this problem that he's in, this situation that he's in. So you know, on the business side, on the personal side, Lots of things, lots of things happened last year. And I, again, I share this with you to let you know that if you're somebody that's struggling in business, in life, if you've got the self doubt and the self talk and you're convincing yourself you don't belong, the fact that these things are going wrong doesn't mean that you don't belong. It just means that you're human and you're in the game. What I'd like to do now is share with you some ideas on how I work around and work through the challenges that inevitably come up in life. My hope is that you can apply some of these when you find yourself facing similar challenges. Maybe you're in a season right now when you're facing some of these. So let's just dive in. Number one, I am really, really intentional about reading very specific books, taking specific courses, consuming certain specific content around whatever season I'm in. One of the questions that I get asked a lot is, hey, Mike, what books do you recommend that I read? And my answer is always the same, like, what season are you in right now? What specific goals do you, what specific problems do you have? And focus your attention on resources that are going to level you up on those things rather than just arbitrarily reading. So as I realized that in the case of my son, that I had no idea how to teach a fifth grader how to divide fractions, I went to YouTube and I spent an entire afternoon and well into the evening watching hours of YouTube videos on fifth grade math, how to teach fifth graders fractions, on how to teach fifth graders how to divide fractions. And I'm watching all these things and spending time to kind of figure out, how do I do this? And then it's, let me go and try two or three of these things tomorrow. Well, you know, when I tried those three things, he ended up storming off to his room crying and slamming the door. I'm like, okay, maybe those aren't the right ways to teach him. And so then the next day I'm back and I'm reading a book or finding some kind of course on how to do it. And, and this is this application or this process of application. Let's try a couple things. And gosh, at the end of the day, most of them didn't work. But we did find one or two things that worked tremendously well. So if you find yourself in a season where sales are down or you're having a part time with managing people or leading people on your team, or your fifth grade kiddo struggling with math. Go and read specific books. Find videos that are kind of specific to that. Ask yourself, like, what season am I in? And just find some books that. Or other resources that help you. Number two, I think this is, gosh, I think this is one of the things I do really well in life and that is seeking mentorship and guidance from people in my life when I'm faced with a big goal or a big challenge or uncertainty. And I think this is why it's so important to have people around you that know you, that see you for who you really are and that aren't afraid to speak into you. That not only are they not afraid, but they're willing to speak into you from a place of truth. And so when I find that I'm really struggling with something, I'm texting those people, I'm calling those people up, I'm asking them to go to coffee with me or to go to dinner with me or to go out for a walk with me. Find those people that know you and see you and truly are willing to love on you and seek out mentorship from them. I'll give you a word of advice when it comes to this. Be as clear and specific as you possibly can about what you need from those mentors when you sit down with them. Because if you're unclear about the question that you have or the help that you need, it's going to be really hard for them to give you what you want. And so before you set those meetings or at a minimum, before you show up, really think through, like, what help do I need from them today? Maybe journal on it or write some notes down ahead of time so that when you get there, you can say, listen, this is the situation I'm in. And what I would love from you today is can you connect me with somebody that can help me with the problem? Can you push back on me and challenge the way that I'm thinking? Or maybe you just need them to listen and just like, look, I don't want you to help me, I just want you to listen. But whatever your thing is, be really clear with those mentors about what you need from them so that they can deliver what you need. In a similar vein, I would really encourage you to be extremely careful about who you surround yourself and what content you consume. You probably know these people in your life and I hope this isn't you, but you know the people that are just like all the time watching the news and I don't care if it's Fox News or CNN News or some other news thing in between. The people are just constantly watching the news all the time. They get these crazy ideas in their head about how the, you know, the world is ending. Maybe you've got the Uncle Tito that thinks that, you know, everything is a government conspiracy and you know, In N Out Burger is really just a front for the CIA and they're listening to you at the drive thru. You know who I'm talking about. You know who Uncle Tito is. If you're constantly consuming the news and you're constantly surrounding your with people that have just negative mindsets, these toxic mindsets that's going to bleed into your brain and into your life, it's going to infect you and you're going to see a tangible change in the way that you see things, the way that you approach solutions to things, the way that you just approach the world. And so be really, really protective around what kind of content you let into your life. Be careful and protective around who you let speak into your world. And the good news is the converse of that is true as well. If you're surrounding yourself with people that are spe positivity into you, that are speaking truth into you, that are taking things from this mindset that, look, these aren't just problems. These problems are actually the roadmap that you need to think through to get to the next side, then that mindset is going to permeate and really impact the way that you show up and the way that your energy is and your positivity and just the way that you are in the world. So be really, really specific and careful around the content and the people that you let into your life. I'll give you a really specific example of how I kind of leveraged all of this in that season when half a million dollars walked out. The number one is I called up a bunch of my mentors and asked them to sit down and I said, hey, if this happened to you, how would you approach it? I got some great advice. In addition to that, I went out and bought, I don't know, half a dozen Kindle books and audiobooks and physical books on prospecting and on sales. I got podcasts on prospecting in sales and I started consuming those on the drive to work. I'm listening to Audible Books. As soon as I get to work, I'm sitting down in my chair on the other side of my office and I'm reading the physical books and taking notes and I'm reading things like fanatical prospecting. Affecting by Jeb Blunt. I'm reading things like Buyer first by Carol Maloney. I'm just surrounding myself with positive people that are speaking into me, and I'm surrounding myself with content that's helping me through that season. And the reality was that really scary season where I lost over $500,000 because of those things that I was doing. We ended up making literally all of that $500,000 back and more in just 62 days. And I know that it isn't coincidence that in that season where I need a lot of help, I was surrounding myself with great people that were speaking into me and I was consuming content that was helping me through those problems. So again, like, just can't encourage you enough. Be really, really intentional around who you're letting speak into you, the content that you're consuming, and be deliberate about it. If you're in a particular season, consume content that's going to help get you through that season or help you accomplish that goal. Don't just start consuming any old thing. Be really intentional about it. Last thing that I'll share with you that really helps me through those difficult seasons is I try to journal a lot when I find myself in those seasons. For me, when I get into challenges or problems or I miss the goal, I get a ton of self talk. And the time of day that the vast majority of that self talk comes in is when I'm laying in bed at night. You know, I'm laying there and the wheels start turning and the voices, they start coming in and then I can't sleep. Gosh, the bad sleep is just a catalyst for me anyway. For a lot of other things, I'm not getting enough sleep at night. That means I wake up tired the next day. I'm groggy. When I'm tired and groggy, I tend to eat a lot less healthy food. When I'm tired and groggy and I'm not eating right, I tend to not work out as much. It's a really dangerous place for me to be because of the downhill consequences of me not sleeping well. And so then the question becomes, all right, what do you you do about the voices? What do you do about the self talk? The number one thing that helps me get that out of my head is journaling. I use a remarkable tablet because it syncs to the cloud and all the things and it goes anywhere I want with me. But I try to double or triple down when I'm really struggling in life with the journaling and what I found to be true for me, I don't know if this was true for you or not. When I journal, it's almost like I create another parking lot for the self talk and the doubt and all the things. I'm able to park those ideas in the journal instead of having them just take up a ton of really valuable real estate in my head. And I find that two or three days of just journaling hard really starts to get my sleep back on track. Now, if you're like me, one of the things you're like, I don't know how to journal. I don't know what to say. Sometimes I just sit down and start writing. I don't have necessarily prompts that I follow or a template or anything like that. I just sit down and start jamming. Like, whatever's in my head, I write it down. If it's self talk, I write the self talk down. If it's I have ideas, I write the ideas down. If I have problems, I don't know the answer, I write the problems down. And a lot of times the answers just start to kind of come out as I'm sitting there. But I'm like, block time off to journal first thing in the morning. If that's you, maybe you're somebody that likes to journal at night. And so you get the self talk, you just roll over and you pick up your notebook and you start writing things down. But the journaling I have found just creates this other piece of real estate where those ideas, positive or negative, can kind of live. And it helps free my mind so I can get back into sleep and get my routine back on track. Listen, the last thing I want to leave with you today is comfort in knowing that you're not alone. You missed the goal, the client fired you, sales are down, team member quit, revenue walked out the door, your kids are struggling, you're not losing weight, you're gaining weight. All those things are normal. Those things are not signs that you don't belong. They're not signs that you're not good enough. They're not signs that you should throw in the towel and quit. Those are all just signs that you're in the game. Anyone that's in the game is having those same kinds of struggles that you are. They either just finished having a season of challenge, they're in the middle of a season of challenge, or they're getting ready to be in a season of challenge. That's true for everybody. Be really careful about watching social media or reading books or podcasts with people that just say that they're winning all the time because it's really, really dangerous, in my humble opinion, for your mental health to just be around that all the time. Find people that are willing to be transparent and vulnerable with you. I would also just really encourage you to be transparent and vulnerable with other people as well. You just sit down with a mentor and ask for help. If you're not willing to be transparent and vulnerable with them, you're never going to be able to get to a place where they're able to help you. So just remember, bad things don't mean that you don't belong. Bad things don't mean that you're a bad person or a bad CEO. Just means that you're in the game. It's the cost of admission for trying to do big things in life. And I would say that it's a sign that you do belong. It's a sign that you are willing to do hard things. So stay in the game. I hope this episode was helpful for you today. Can't wait to see you back here next week, my friends. I'll see you then. All right, my friends. I hope you found this episode helpful. If you did, it would mean the world to me if you would leave a five star review on Apple Podcasts, Google podcasts, Spotify, wherever you're listening to this episode. In the meantime, I can't wait to see you back right here next week. I'll see you then.