Leadership Podcast 41 How I Almost Bankrupted My Business and Turned It Around

How I Almost Bankrupted My Business and Turned It Around

You've got a money problem in your business that you haven't told your spouse or your team about, and every new sale convinces you it will fix itself. Eric tells how he stopped his weekly budget meeting, leaned on a line of credit and then a credit card while telling no one, and what he did to recover: confessing to his wife and team, a pay cut and staff cuts, a return to OP3, a $3,000 a week critical mission, and a pipeline worked with urgency again. You'll leave knowing how to catch the drift early and what to do first if you're already in it.

65 MIN March 30

Notes

This is the most personal episode Eric has recorded. In the fall of 2023 the business was growing every week, and he and his wife met weekly to ask whether they were on track to make budget. Success became routine, Eric got bored with routine, and the meeting stopped. Over the next year he dipped into a business line of credit, maxed it out, moved to a credit card, and told no one, because every $20,000 website or $1,500 a month client felt like the turnaround. Meanwhile clients left for ordinary reasons, like a new general manager bringing in her own vendor.

Eric walks through the road back. He came clean with his wife and his team, which he calls the hardest thing he has faced as an owner. He triaged right away: a pay cut, moving some staff to part time and filling the gap himself, letting go of freelancers he cares about, and cutting every recurring expense that wasn’t a necessity. He went back to his own OP3 framework (one person, one problem, one product, one pathway) after admitting he had been plowing new fields instead of tending the garden he harvests from. He set a critical mission of $3,000 a week in new sales, four direct offers a week, and one conversation a week with a strategic partner candidate, and he filters every task with one question: what’s the cost if I don’t do this? Then he worked the pipeline again with three referral calls a week, calls into a partner association’s member list, and outreach to twenty strategic partner contacts a week.

Two weeks of making budget later, Eric explains why he never panicked: when you know how something works, you know how to fix it when it stops working. The leadership tip of the week is the one he had to relearn himself: practice what you preach.

Key Highlights

  • Bad things grow in the dark, so it’s okay to have surprises but never secrets.
  • When you know how something works, you know how to fix it when it stops working.
  • Don’t wait until day twenty-five to find out you’re behind on budget; know on day five and adjust.
  • Before a task goes on your list, ask what it costs you if you don’t do it.
  • Your leadership capacity is the capacity of your business, so when you stop leading, the business stops growing.

Key Takeaways

Q: Should I tell my team and spouse about money problems in my business? A: Yes, and sooner than feels comfortable. Eric carried growing debt alone for about a year, and every new sale gave him another reason to stay quiet while the hole got deeper. Bad things grow in the dark, and telling the people it affects is what makes a real fix possible.
Q: What should a business owner do first in a cash flow crisis? A: After getting honest with the people affected, triage the worst of it right away. Eric took a pay cut, moved some staff to part time and covered the work himself, let go of freelancers, and cut every recurring expense that wasn't a necessity. They were hard conversations, but waiting would have made every one of them worse.
Q: How do I know if my small business is on track to make budget? A: Set one weekly number and check it every week. Eric knows his monthly recurring revenue, his expenses, and the gap, so his critical mission is $3,000 a week in new sales, supported by four direct offers a week. Checking weekly means you know on day five, not day twenty-five, when you need to adjust.
Q: How do I decide which tasks to work on when sales are down? A: Ask whether the task directly gets you to this week's sales number. If it does, it goes to the top of the list. If it doesn't, ask what it costs you if you don't do it, and if that's a cost you're willing to pay, drop the task.
Q: How do you ask a client for a referral? A: Call, don't email. Eric reviews a client's results before the call, asks if they're happy with them, and then asks who they know that would want results like that. Asking who do you know gets far better answers than asking do you know anybody.

I’m going to share with you today how I about ruined everything. And I mean everything. Almost drove my business and my family into bankruptcy. This is probably going to be a link I can give to people when they ask me about my most embarrassing moment, because it is embarrassing. This has been a humbling and humiliating experience, and I’ve decided today to open up the curtains and share it with you through this podcast.

In today’s episode, you’ll discover what I did, how I almost ruined everything, but also how I turned things around and what you can do when you need to make things right in your business right away. It doesn’t change the fact that I wish we would have never gone through this experience. So listen in. I’m going to ask you to listen with ears of grace, and that you would not judge, but that you would learn.

Welcome to the podcast, everyone. My name is Eric. I am a digital nomad entrepreneur. I’ve been traveling around the world with my wife and our four teenagers for over three and a half years now. We’re currently in the United Kingdom, having a great time as a family, learning a lot, growing a lot. We still love the location independent lifestyle very much. But I almost ruined it. I almost ruined it.

So in today’s episode, I’ve got three things I want to walk through with you. First, we’re going to dig into the road back from disaster, is what I’m calling it. I’m going to tell you where we almost were, and then how we’ve got things turned around. Then I’m going to share with you this week’s leadership tip of the week. And then I’ll give a travel update for those of you that listen because you like the travel side of things.

Now, before I get into the story of what happened, if we have never connected on LinkedIn, I would really appreciate connecting with you and having you as part of my network over there. I’ve made it very simple for a season. My personal vanity URL, ericdingler.com, just forwards right to my LinkedIn. So make sure you go to ericdingler.com, connect with me, send me a message, and let me know when you send that request that you’ve been a listener of the podcast.

All right, so let’s just get into this. Is it as bad as I made it sound at the beginning? Yeah, it is as bad as it was. I made a massive mistake. Basically I didn’t practice what I preach. I took my eyes off the ball and I had gotten complacent. To be honest, I’m not surprised. When I look back over my life and my experience, this is somewhat par for the course. When I get complacent, when I get a little bored with things, I start searching out the new thing, or I want to start playing with the systems and not staying on mission critical tasks.

So in the fall of 2023, things were going great with the business. The numbers were great, moving up and to the right every week. My wife and I would sit down and have a business meeting, and we’d look at things like: are we on track to make budget, yes or no? How are expenses doing? If we’re not on track to make budget, what do we need to do? What’s in the pipeline? We had this meeting every week where we were working the numbers, keeping an eye on things, and setting priorities and tasks. The business was doing great. I was happy, and it just became very routine. Success became routine. And I get bored with routine. I get bored with routine.

So as we pivoted out of El Salvador and into Costa Rica, we stopped having this meeting. That was okay for a while. Things went along well, and we’d check in every once in a while, but I no longer had that regular weekly rhythm.

And last January, January of 2024, all of a sudden I had to tap into a business line of credit. I wasn’t worried, because I knew about a project we had just closed, and sure enough in February that money came in and I paid back the line of credit. It was no big deal. But that should have been a big deal. That should have been a red flag. February was fine. March was fine. In April I dipped in again, and I wasn’t able to pay it back right away. But then something else came up. January, February, March, April, I dipped back in. May, I carried the line of credit. In June it cleared to zero. And then in July I started dipping into it again, and I’m telling you, it didn’t take any time at all before I was sitting there with a massive amount of debt, maxed out the line of credit, and had stepped into a credit card. And the entire time, never said a word to anybody. I just kept plugging along, because every single time we’d land a project, land a sale, I was like, yes, this is the thing, I don’t have to worry, look at this, we just did a $20,000 website, everything’s turning around. Oh, just landed this new client, $1,500 a month recurring revenue, no big deal.

And the thing is, all along I knew I should have been saying something to the team, to my wife, because here’s the thing: bad things grow in the dark. Bad things grow in the dark. I know this. I teach this. We tell our kids this. It’s okay to have surprises, but we shouldn’t have secrets, because bad things grow in the dark. This is a leadership lesson, and I know it. I know it. It’s a leadership law. But I violated it. I violated it. I was the only one who knew the numbers, and I just got cocky and arrogant and overconfident.

A sale would come in and I’d think, this is great, we’re in the clear. And then a couple of weeks later we’d have a client leave, taking that same $1,500 a month with them. And people weren’t leaving because they were mad or upset. One client left because they hired a new general manager, and the manager already had a working relationship with someone else and wanted to bring them in instead. The owner told her it was her call to make, so they left. That happens. I’m not mad, I can’t fault them, but those things just kept happening, over and over.

We got into the first part of this year, 2025, and I’m screwed. I’m stressed out, I’m not sleeping well, I’ve got this big secret, I’m dealing with all of these negative emotions, feeling like it’s an apocalypse, to the point that I didn’t know what to do. And here’s why that statement is so stupid: I knew what to do. I just didn’t want to do it. I would pray every morning, I would beg God, plead with God, to fix this. And all along I just kept hearing in my head: bad things grow in the dark, why do you keep secrets? But I didn’t want to tell my wife. I didn’t want to tell the team. It was embarrassing. It was humiliating. I was coaching people in their businesses. I was recording podcast episodes about how to run your business. And here I am thinking, I have driven the bus off a cliff.

So I had to turn it around. Here’s what I did.

Number one: I had to get right with God. I wasn’t praying right, I was praying without wanting to actually do the right thing. I had to start praying for the strength to do it.

Number two: I had to get right with others. I had to confess my sins to my wife, and I had to confess my sins to my team. Those were not comfortable conversations. It hurt them. I hurt them. I had to deal with the fact that I had caused this hurt, this betrayal of trust. It was the worst thing I’ve ever been through as a business owner, and one of the worst things we’ve ever walked through as a family, right up there with a miscarriage we went through in our first pregnancy and the loss of family members. It was really bad. I had to give myself a lot of grace. My wife gave me a lot of grace. I started counseling to help deal with all of it.

I couldn’t just lay in bed and cry about it. I had to put my big boy pants on and get back to work. And the thing is, all along I knew what I had to do. I just kept refusing to admit it, because admitting it meant admitting reality, which was that I was dropping the ball. It was easier to work on something new than to work on reality. I explained it to my wife and my team like this: I kept going out and plowing new fields, thinking if I just created enough new opportunities, enough activity, that was the key. All along I knew that was stupid. What I actually needed to do was focus on my garden. A storm came through, and I was the storm. It knocked the shed over, scattered the tools, left debris everywhere, and I lost some plants. That garden is where I harvest, where our resources come from, and I’d let the weeds grow up in it. I had to let the fields go fallow and focus on the garden.

Number three: I had to triage the worst of it, right away. Four things. One, I took a pay cut. Two, I had to cut some of my staff down to part time, which meant stepping in myself to fill the gap of the work they’d been doing. Those were hard, embarrassing, humiliating conversations that I desperately didn’t want to have, but I had no choice. Three, I had to lay off freelancers I care deeply about. They weren’t on payroll, weren’t quite on the team, but I care about these people, and it hurt that I couldn’t keep giving them work. Four, I went through the budget and cut every recurring expense that wasn’t a necessity, things that had built up that just made life a little easier but weren’t essential.

Number four: I had to get back to the basics, and practice what I preach. Here’s the thing: I knew exactly what to do. I never panicked. I never sat there thinking I don’t know what to do, I don’t know how to make a sale. I always knew what to do. I just denied it, and kept working on the wrong things even though I knew better. The basics are simple. I had to focus on the one person with the one problem we solve, the one product that solves it, and the one pathway to sell it. I was going out trying to create additional pathways, turning over new fields, trying new products, different things. I had completely violated OP3, my own framework: one person, one product, one pathway. I was teaching it and not doing it. But a few weeks ago I sat down and said, that’s it, going back to basics. I already had my OP3 document. I just went back to it.

Number five: I had to reestablish my critical mission and my daily reading script. My critical mission is this: I had to sell $3,000 a week in new sales. That’s it. I know what my monthly recurring revenue is, I know what my expenses are, I know the gap, and I know how I’m going to close it. That’s what my wife and I used to sit down and check every week: are we on track to make budget? You don’t wait until day twenty-five of the month to figure out you’re behind. You know on day five, and you make adjustments then. We really only need $2,000 a week bare minimum, but I set the target at $3,000, because I’ve got a little debt to eliminate and want to build reserves back up.

To hit that, I know I need to make four direct offers a week. I also wanted to start having one initial conversation a week with a strategic partner candidate, which is new starting this quarter. And I wrote down the ruthless elimination of distraction. Before I organize my task list now, I ask myself: is this task mission critical? Is it directly going to get me to that $3,000 this week? If yes, it goes to the top of the list. If no, I ask a different question: what’s the cost if I don’t do this? Not is it important, not is it urgent. If the task doesn’t have a cost I’m willing to pay by not doing it, it goes away.

Then finally, I worked my pipeline, with a renewed sense of urgency. This is the very first thing I teach in almost everything I do: create a pipeline and work the pipeline. I had stopped doing that, and it hurt us badly. I’d gotten complacent, gotten lazy, stopped reaching out, stopped being bold with prospects and cold leads, stopped making sure we touched base with people at least six times. So I immediately went back to working it. Every week I fill the front of my referral request pipeline with people I can call, not email, actually call, and I pick three people a week to move from opportunity to call. I check their metrics before I call, ask if they’re happy with the results, and ask who they know that would want results like that. Not “do you know anybody,” but “who do you know.” That’s how you ask for a referral.

We also have a business association we partner with, and instead of dabbling with it like we did last fall, we’re now making real calls into their list. I’ve got someone on my team making calls as an appointment setter, and my wife has been making calls too. I found the best wife out there. After we worked through the hurt of what I’d done, the first thing she said was, “How can I help?” She’s been making calls, offering a free member benefit report that shows people how their business ranks locally, and following it with a three-month local SEO offer we guarantee results on or keep working for free until we do. It’s a clear foot-in-the-door offer that naturally leads people to want more. That’s OP3, and I’m working it.

We’ve also started reaching out to twenty pre-identified strategic partner contacts a week, people we could refer work to and who could refer work to us. We just need one meeting a week out of that, because I only need to sell $3,000 a week.

The last two weeks, we’ve made budget with no problem. This coming week we’re already going to be above budget. I know who I’m calling, I’ve got the right meetings on the calendar, and I created three ranking reports today for people who already said yes, they want to see it. I think we’re going to be completely out of this mess in about eight weeks. And I can’t take credit for it. It’s my team, it’s our system, it’s my wife, it’s my friends, it’s my God. I’m not left alone to myself, and that’s not good.

This is why I never panicked. When you know how something works, you know how to fix it when it stops working. And it stopped working because I stopped working it. I took my foot off the accelerator, got distracted with new things, and started working on things we might need one day but didn’t need yet, things I wasn’t even the right person to be working on.

So we fixed it. And you can fix it too. But let me just tell you: I never want you to have to fix it. I want you to stay in your lane, stay focused, know your numbers, look at the data, have transparency. Bad things grow in the dark.

It’s been a month since I released a podcast episode, because it wasn’t mission critical. I love doing this, but the last several weeks it had to wait. I almost didn’t record this one either, because of the humiliation. I’m turning fifty this month, and I acted childish, and it’s embarrassing to admit that. But I thought, somebody needs to hear this. Somebody needs to hear that bad things grow in the dark. Somebody needs to hear that the system works, not just when things are going well, but when it’s critical, when it’s an emergency. Get a system, work the system, know why it works. Do less, with more focus, more energy, more excellence, and the results multiply.

If you’d like crystal clarity on your OP3, on who your person is, what problem you solve, what product solves it, and what pathway sells it, I’d love to help. I’m running another ninety-day accelerator, recording this on March 30th, 2025, releasing April 8th. I just wrapped a cohort, and it was funny, at the start of it I was telling them what to do and not doing it myself, and things weren’t working for me either. As I dug back into my own OP3 and started following my own system again, the exact same thing happened for them, because I was finally doing exactly what I was teaching. The promise is this: you sign up, and at the end of ninety days you’ll have a profitable business model built on OP3, guaranteed, or I’ll work with you one on one until you do. Then ninety days after you deploy it, you’ll have doubled your investment in the accelerator, or again, I’ll work with you until you do. If you’re interested, reach out on LinkedIn through ericdingler.com, email me at eric at dnepodcast.com, or go to dnepodcast.com and schedule a twenty-five minute strategy session. I’m only doing two of those a week right now.

That was the road back from disaster. I’ll keep you updated in the next several episodes.

Now, this week’s leadership tip of the week. I had something else planned, but I scrapped it, because this one needed to be more on the nose today. Your leadership capacity is the capacity of your business. You’ll never grow beyond your capacity to lead. I stopped leading. We stopped growing. In fact, we went backward. This week’s tip: practice what you preach. I know, that’s the pot calling the kettle black. But I’m back to it, and I’ve got to keep it in front of me. When I practice what I preach, life is good. When I don’t, life isn’t good.

For those of you still here, thank you. If you like travel updates, we’re having a great time, still in Liverpool for a bit over a month. The last couple of weeks, I’d been so stressed about the business and carrying all of that darkness that I hadn’t realized I’d also stopped doing anything to bring joy into our household. That bummed me out. My wife and I talked about it, and the last couple of weeks I’ve been working hard at bringing joy back in. We painted portraits of each other. I got my butt kicked in Monopoly by my twelve year old. And last weekend the kids each picked numbers within ranges we gave them, and we averaged one number, then used the others to pick a bus, count stops, walk blocks, and land on a restaurant, with the final number as our per-person budget. We ended up at a place with ramen and udon we never would have found on our own, and had a blast. The kids loved it so much they came up with an idea for an Uber Eats roulette, where everyone draws a name and orders that person a surprise meal within a set budget. We’re doing that in a couple of weeks.

I kind of lost track of things there for a bit. I got complacent, and I wasn’t being the leader, the husband, or the father I wanted to be, and it wasn’t good enough. I feel like I’m coming out of a fog I never knew I was in. Most years I pick a season to pray and fast for twenty-one days, and every time I do, I feel that same way coming out of it, even though I never notice walking in. I didn’t do it last year. That’s part of why I had to get right with God first.

Dear listener, podcast friend, thank you for listening this far. Would you do me a favor? Let me know you made it this far, comment on Spotify, send me an email, leave a review, subscribe. It would mean the world to me and let me know this was helpful. This is a small podcast, it’s niche, and I don’t have thousands of people listening to every episode, so please don’t assume somebody else will tell me. You let me know. And if you think somebody would benefit from this, share it.

Until next time, I want you to chase the big dream, lead with courage, and safe travels.

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