Jeff
Appearances
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, a combination of things. It's always a great question in a group to say, hey, what percentage was success and what percent was luck? And it was definitely a combination. I think of it like winning a poker tournament. Sure, it's possible to not even know what you're doing and just go in 20 times in a row and win. I think, one, it was a good idea. It was my co-founder's idea.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was ahead of its time. But it was a good idea and we caught a wave five years in, ten years in, that picked up steam. I would say we had a good division of labor in the startup where my co-founder was a brilliant coder. He was technical, I was sales. So if it had to do with code, it was him. If it had to do with the business, it was me. And we stayed out of each other's way, which was good.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
We didn't go too far too fast. If I would have had an ability to raise venture capital early, I probably would have done it. And that probably would have been a mistake. So again, we took the long view on things, short-term generous, long-term greedy, anything we could do to get the product in the customer's hands and using it, we know we would succeed in the long run. We deferred gratification.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So we didn't have a big fancy office. We had a crummy office for a long time while we were profitable. We didn't get hit by a lightning bolt out of the sky is definitely one. So you didn't get killed. Didn't get killed. Cease and desist letter, sued by a customer, a breach, sued by... I know we never got sued, which is nice.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So really a combination of things, you know, Rob, over the long period of time, I mean... I don't want to shoo away any credit. I think we made more good decisions than bad decisions. I think we recovered quickly from our bad decisions. We weren't afraid to take certain risks that had favorable payoff conditions. And we weren't in a rush. We went, you know, we went, I call it bootstrap.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
We had a small amount of money from outside investors that got us over the line.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I think this is one of the benefits of being a bootstrap company. We didn't have a quarterly number that we needed to make. And that means you don't ever sell the product to someone who's not a good fit. You sure try not to. There could be an occasion where
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
there's a prospect and they really should buy your competitor's product, but you need the money or you need to make your number for the quarter. And we never did that. And then there were occasions where maybe the person we were dealing with had a very low budget authority, including our first sale of $9,920 in December of 2003.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And you think, well, geez, this is a customer that should be $100,000 a year customer, $50,000 a year customer. and the person you're dealing with is enthusiastic about it but they can't convince their management or they don't have the budget and we'd say, what do you got? Can you sign for $5,000? And we would do that. We would do that consistently.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
The way our licensing worked as well was the product did not have a feature that would exclude someone from using the product because they'd exceeded a license count. So we sold on concurrent licenses, there's a number of ways to do it. There was also a generous way to do it was concurrent versus named users, which people liked.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And then if we thought, hey, you're going to need let's say 50 concurrent users and that's whatever it is, 10 grand a month, we would say, I'll tell you what, first year we're going to charge you for five and take advantage of us. I mean, just rip us in half. I hope you get up to 75 because I'll catch up with you next year. And if that's a problem, we'll work with you from there.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So you could be sitting around forever trying to get that 50 concurrent license thing, but I'll sell it to you for cheap for five because I know you're going to like the product. I know we're going to take care of you. I would say also, you know, we had a methodology or a viewpoint that like we never tried to avoid our customers. Like we had a phone number that spelled the company's name.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And you could call that number and one of our people would pick up the phone and help you through a problem. And the idea was always let's try to give great support where no matter what, even if you forgot your password, we're not going to farm you out. to someone else, we're not going to send you through an IVR, we're going to try to get a human to pick up the phone.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And then after we surprise and delight you with some great service, we're going to take an opportunity to say, hey, by the way, is there anyone else in the, in the company, maybe that could use the product? Or, you know, is there are there other things we could do, we could do better than when once you've done a good job serving them.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So that's just another example of being generous and greedy at the same time.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Hey, Rob. Thanks for having me.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, it's a great question. I'd say time moved at different speeds in different parts of our history. So the first couple of years crawling over broken glass, it was like time in the dentist's chair. It couldn't have gone slower. The first few years felt like 100 years. Once we got to profitable and had a pretty good sense that we were going to be okay, that part went fast.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So from 2007 till the time we sold a majority share, that 10 years might have felt like two. Although there were some struggles, of course, along the way. I don't mean to think it was all sunshine and roses during that 10 years. But that time was really good. We had a small team. It was a good team. We worked well together. It was small enough where you knew everybody.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was big enough that you could take a vacation and expect that the company would still be alive when you returned.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I'm happy to walk through the transactions if it's useful, but I think the total was about $88 million. That went to you directly? That went to me from the equity sale in three chunks.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, boy, Rob, I could go hours on this. I'll try to distill it as best I can. Everyone has a number in mind, right? If I could get this amount of money, then I'd be set and I'd be done. Mine was $10 million. And I think most people, when you say my number is 10, you really think of 20. So that was life changing.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I was down there and then first check was 21, second check was about 40, third check was 27, 28. And I remember in vivid detail the day we sold, cashing the check, taking my family out to dinner in a limousine, what we had to eat. I could bring you to the table where I sat. Second time we sold, Rob, $40 million. It closed early in the morning. I was in a conference room by myself.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I don't remember what I did. that day. I don't, I mean, we might've gotten pizza that night. I honest to God, I don't even remember. And I'm not sure how useful this is to your audience, but I mentioned this on another podcast I was on. I think most people have a default perfect amount of spending, meaning like maybe you can afford to, you know, fly first class and stay in a nicer hotel and, um,
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I don't know, have a decent car, you know, whatever it is. Everyone has their sort of ideal amount of spend. And when you have less than that, life is of course painful because you're wanting to rise up to that. There's also another side and I can already...
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
feel the eyes rolling in the audience, and my eyes would have been rolling as well, that when you're above that, if you have more money than you can spend, it creates a certain kind of an issue as well. And just some examples of that are feeling the need to maybe go do it again or give it away. And it's just more challenging than you'd think.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I made a lot of the mistakes that I think people who sold their business make. You do what the world tells you you should do. You go to try to work with nonprofits and you realize how frustrating and slow that is if you're a founder. I bought a bunch of stuff. I had four houses and a jet at one point and realized, you know, stuff isn't where it's at.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Experience and community and relationships are much more valuable.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
than uh than that and i also grossly underestimated how much i would miss the structure and the purpose and the identity uh that i had in my in my former life and i know i've been talking a long time i can hear myself talking but i just i just want to say to the audience like if you're rolling your eyes right now or you're saying like what a moron just believe me when i say when i was starting i would have said the same thing like how is it possible you know you have this giant pile of money and you don't just write off into the sunset and
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
and spend the rest of your days with frozen drinks and sunsets and boats?
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I guess the obvious answer would be I must not be that interesting. But perhaps beneath that is I like to keep a low profile just for my own safety and security. And by being anonymous, it also helps me be completely authentic with anything I have to talk about.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Oh, gosh, Rabia, congratulations, by the way, because you have accomplished something a lot of people in my situation or similar have not. Six months is a, you're much smarter than me and a lot of others that I've worked. And I stood up a group called Beyond the Finish Line It's btfl.org if anyone is in the same situation. But I can kind of distill a lot of the conversation is this.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I want you to picture a Venn diagram, two circles. One of them is doing something important with people you know and like and trust, right? It's being back in the trenches. It's going to war with your friends and being an important part and being useful in that. Okay, that's one circle. And the other one is absolute freedom and autonomy and independence to do whatever you want, anytime you want.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And as it turns out, the joke is it's not a Venn diagram, there's two circles. There's no overlap. That's great. And so the key, I believe, is to find something as you did, and I have friends that are in the group that have found something that is worthy of sacrifice of that second circle.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So if there's something that you feel passionate about, or you feel like you're giving back enough, you're useful enough, you're willing to say, I'm a skier. So I'm willing to say, you know what? We've got perfect ski conditions today. I got six inches of powder. It's blue skies. The lines are short. It's 20 degrees and the light's good. And I have to say, I can't do it. I can't go ski today.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So it has to be something that's worthy of sacrificing your independence. So kudos to you for finding that. And the North Star I use now or I try to use now is energy. So if I've got something, like I'm enjoying talking to you, I was looking forward to talking with you today. If it's giving me energy, it's good.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And it doesn't matter how much money you have in the bank, Robin, anyone else listening, it doesn't matter how much money you have in the bank. If you've got low energy, life sucks. It doesn't matter that you can push a button on your phone and have a plane come pick you up somewhere.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
If you're not looking forward to the day and you're not looking forward to what you're doing, your energy is low, life sucks. And if your energy is high, it doesn't, you know, maybe I'm working on a home repair project or something. If my energy is good, life is good. So that's the new scoreboard because it's not money anymore.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, so let me start with the negative response on that, which is the real generic ones I can't help with, like, you know, what kind of business should I start? Those I try to write, and I'll need to spruce up my website before this publishes, but I'll try to write a, you know, very basic response. you know, applies to everyone, answer to a very basic applies to everyone question.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
The ones that are useful are people that have a particular situation or problem that I can help with. If someone does, you know, business to consumer or they're trying to open up, you know, a market in Asia or something, I can't help.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But I've had I don't know how many calls and this brings me energy so I'm so happy to do it which is why I don't need money, I don't have a coaching service, I don't have anything else, it just gives me energy.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I've been I think an authentic ear for the people who are going through it and that's where I think I can provide some good in the world from people who can't make payroll, from people who are thinking about a big partnership, thinking about selling. their spouses telling them to get a real job. I talked to a guy whose co-founder committed suicide in their apartment.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I've talked to people who are in the process of making mistakes that I've made. And I think it's really a relief for a founder to be able to talk to someone who's been through it and can say, yeah, me too. You're not alone and it's going to be okay. While not having to sort of like secretly pitch me for an investment, I make no investments. No investments in anything. That's the trade.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I'll not write a check, but I'll not ask you. I don't want any shares, warrants, options, nothing. I want nothing.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Thanks for having me, Rob. I really appreciate and enjoy your work. Nice to be in touch with you.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Oh man, the first word that comes to mind is relief. And following that, probably enthusiasm. As a bootstrap founder, it's very difficult to take a lot of risk.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So when we sold the business the first time to a private equity firm, and if anyone wants to contact me on Twitter or wherever, I'd be glad to share details about who our banker was, who the private equity firms were, but I'm going to keep those keep those anonymous as well for now.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But I was excited to work with people and actually be able to put money into the business and pursue some of the crazy ideas that I had as a founder. But when you've got 98% of your net worth wrapped up in your business, it's really challenging to say, hey, you know what, this is a crazy idea. And I think it's a 5x payoff if it works. It's hard to pursue those things.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But the first thing was relief, man. If I listened to your latest podcast and your guest talked about sleeping for 14 hours. If anyone gets to retirement, I don't know if this is good news or bad news, but the best thing is the sleep. It's just so great to sleep. It's so peaceful. Oh, it's so peaceful. I went a dozen or more years where I was asleep. I was unconscious, but I was still at work.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
You know, my dreams were all involving work and to be able to actually get to sleep is great. So that was the first thing.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
14 is a great, great multiple.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was a combination of things. I mean, the market was very strong at that moment in time in early 2022. So that can't be disregarded. But the mental model I use when describing this to people considering selling their business is a slot machine. And I didn't know this going in, or I would have had some better numbers. But
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
you know, just excluding market conditions, you take your revenue is sort of the first reel of a four reel slot machine. And then you take your gross margin. And I'd never really calculated our gross margin. I mean, I knew how the business worked, but I'd never really dug into what our gross margins were. And we were about 90% gross margin. So it was a mature product.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was all our own code and open source. We didn't have any licensing costs. So we had high gross margin. That's reel number two. Third is retention. And I knew we took really good care of our customers. It was one of the reasons we had, I think, such a good outcome and took so long was our patience. But we took really good care of our customers. We had 117% net retention.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So it was a- Negative 17% churn. Yeah, negative 17% churn. That's-
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And happy to talk about some of the strategies that helped that. My favorite of which is short-term generous, long-term greedy, which I'm glad to talk about later. But the fourth reel is growth. And at the time we sold, the first time, we got seven times revenue. So seven, not nearly as good as 14, obviously.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But if you think about that slot machine, our growth was only about 20-22% a year when we sold. So if we would have had 100% growth and 90% gross margin... and 117%, that would have been a jackpot. But we were kind of like jackpot, jackpot, potato for that last reel on growth.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But perhaps the private equity company that acquired the majority stake saw that we had a lot of potential because we weren't aggressively spending in sales and marketing at that time.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, we were business-to-business security software. And if anyone wants to find me, I'm not hiding, send me a message online or on Twitter or something. Just like with you, glad to introduce myself. But it was business-to-business SaaS.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was an abject failure to get one-time licenses is the honest answer. That's amazing. I'm a salesman by trade, so of course we were trying to get $100,000 for the software. And then the way it used to work is you'd pick 15%, 20% maintenance ongoing. But we weren't able to do that. We were two guys and a dog, and the dog was a loner. and nobody wanted to give us the money.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It was really Salesforce that I recall as being one of the real earliest pay-as-you-go. The difference in our case, we adopted the pricing model of a subscription, which I think was very healthy for customers and for customers and for the tech companies. But we were still on-prem. So we were shipping servers, still probably shipping on-prem servers to customers.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
But it was really the licensing that was rather novel at that time in 2003. And again, driven out of necessity, not some kind of foresight or wisdom.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, I was not working another job. I was unemployable at the time. And for clarity as well, we did raise $350,000 of an angel round. So mostly bootstrapped is how I should call it. And that was the last capital. Yeah, that was the last capital. And I said, I had a previous company that I sold.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
in a dot-com company that we, let's not venture into to waste time in the interview here, but I had a little bit of money left over from that after failing at a couple of things in between. So we were burning money at home for a long time. It was a tough first five years.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, it was the first year we did a million dollars of revenue was 2007. I think we were at about seven employees then. So it was just the two of us for a year. We did $9,920 of revenue our first year in 2003. Yes, I remember, and I have a copy of the purchase order I could put my hands on right now. That's cool. That was a big day. Yeah, a million dollars of recurring revenue.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, I'll give you one early and I'll give you one late. The one early is sort of a combination of stories, but I remember a year in, two years in, something like that. I mean, we're doing almost no revenue and it's just not working. I think we were a little bit early.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
for the market we were in and it's security software so it's difficult to get a beach head and just thinking, man, if I had any other opportunity, I mean any opportunity, like three grand a month and a dental plan and just like relief from the pain I'm going through, I would have jumped on it.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And I remember a particular moment where I was fighting with the printer or something like that and I was just really angry and frustrated and I think that's one of the things, I mean I hope your audience takes from me and from each other is that it's hard. Man, it's hard and it's lonely.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
And having somebody to talk to authentically where you're not in pitch mode and talking about how great it is and feeling like everybody else is doing great and you're not. But it's really hard. It was hard and it was lonely. The second one I'll give you was late in the process and was a contributor to deciding to sell the business. And this was 2015, I believe.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
where we were doing well, and I had taken a loan. I built an office building for the company, and I took a loan of $6 million with a personal guarantee. I didn't have that kind of money, but the company had cash flow at that point to support that. And we had a security breach. Nothing was lost. but someone got through the first level of our security.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
It wasn't our software, it was a piece of open source code. I don't remember what it was, but we were stuck. And one of our customers said, hey, we've got a red light on the dashboard here. Somebody broke through the front line of security here and they're checking the doors to the vault. Then another customer, same thing. We were under attack at that moment in time.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
I just signed a loan for $6 million to build this. In security software, one bad line of code could ruin you. It wasn't our code, couldn't fix it, totally out of our hands. That's a moment I won't forget. That's a moment that all the ships were down and we didn't really have any ability to play the hand. Our team came together and when a fix was available, we fixed it.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
That's one that I won't forget.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Yeah, I've got plenty of weaknesses, but panic is not one of them. Equanimity, I think, is one of my strong suits. But this was a case, I'm a salesman by trade, so I didn't have any ability to understand really what was going on and had to rely on the team. And I believe it was a Friday night and we just got to the point where there wasn't anything else we could do.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So I think we approached it rationally and then... You talk about the events that just sort of happened to you, there's just a big wheel in the sky that spins and sometimes your number comes up and that could be getting a disease or getting in a car wreck or in this case having a piece of software that you were using that had a vulnerability. Fortunately, we were able to work through it.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
Fortunately, the other safeguards that were present in our software held strong. I don't know if it's interesting, but a lot of security software you could say is like it's an alarm or it's a fence or a moat or a gate or something. We were a vault. We protected the vault. of some very important customer information, casinos, law firms, banks, hospitals, things like that.
Startups For the Rest of Us
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit
So it was not a system that could fail without massive repercussions for everyone. So anyway, glad to have that behind.
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Where? Where? Right behind. Right in front of Jeff. Look straight up the hill. You got to look real easy. You got to turn away and look.
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Keep with him, Jeff. Keep with him. I'm going to keep an eye on him.
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I could not have said it better myself, coach. Your dad is a loser indeed. Let's take a quick commercial break and we'll be back with the game.
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Touchdown, Jim, that's me, ran 72 yards in the wrong direction, confused by the bright lights, only to be carried back by my quarterback to the opposing end zone where the final touchdown was scored. And while I had not even made the team that year, we were six players short that day because the opposing team failed to show up and the coach made the call.
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Small Changes Now Mean Big Wins Later
And of course, I learned everything from Dr. Deloney.
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Small Changes Now Mean Big Wins Later
Well, it's really just truly a gift that my parents have prayed for. They've always prayed for wisdom and discernment over my life. And I learned to communicate well at an early age. So my mom can tell you I probably spoke too much. But being a trial lawyer certainly honed that skill of just dealing with conflict. Yeah. Okay.
The Ramsey Show
Small Changes Now Mean Big Wins Later
I teach that arguments are not something to win. You never want to win an argument because you start to lose the relationship. Instead, you want to see arguments as something to unravel, find the knot in the conversation and start to unravel it rather than tugging your way and me tugging mine.
The Ramsey Show
Small Changes Now Mean Big Wins Later
And so when you go into the conversation with something to learn rather than something to prove, you're going to walk away with a much better communication. All right, I'm going to use that tonight when I get home.
The Ramsey Show
Small Changes Now Mean Big Wins Later
Yeah, absolutely. And at the same time, we are trying to replace connection with transaction. Like you're meant to feel the warmth of a smile, not read it in an emoji. And so too often we replace one for the other when all you have to do is just pick up the phone. And most people don't want to do that nowadays. Why not?
The Ramsey Show
Small Changes Now Mean Big Wins Later
I think it's much easier to stay safe and not feel like you can be direct or aggressive or say what you need to say. You'd much rather kind of stand in the back. But if you really want to level up your life, you have to practice the skill of disappointing people. You have to practice the skill of being direct and saying what you need to say. You can still be kind. You can still show grace.
The Ramsey Show
Small Changes Now Mean Big Wins Later
But at the same time, to avoid clarity is to create confusion.
The Ramsey Show
Small Changes Now Mean Big Wins Later
what are some tips you could give a guy like me on how to honor and respect the person that i work for but also challenge well you want to make sure that you say what you need to say right up front people believe that confidence is something that you need to say everything all at once Confidence is very quiet. Insecurities are very loud.
The Ramsey Show
Small Changes Now Mean Big Wins Later
And so when you're always just holding it in or feeling like you know better and you only wish I could only just say, people that are in positions of power or positions of superiority, they will appreciate the more transparent, honest conversation every time rather than you trying to be
The Ramsey Show
Small Changes Now Mean Big Wins Later
a wallflower and just be a yes man every time so you you have to be able to get out front of it and say what you need to say put it up put it out there yeah every every time or else you're really doing yourself a disservice yeah
The Ramsey Show
Small Changes Now Mean Big Wins Later
Yes, yeah. I think that when you come at it from a position of making them feel good and close to you, Also being very firm. My dad would say this. I would come with him with something that I didn't like and I needed to vent. He'd say, well, that's fine. You don't have to like it, but you need to understand it. And it was this idea of you can connect with somebody and still be mad at them.
The Ramsey Show
Small Changes Now Mean Big Wins Later
I can still love you and still be upset. And so he would always say, well, you don't have to. That's fine. You don't have to like it. You just need to understand it. And that allowed me, I mean, I didn't like it when I was young. I didn't feel that great. But now I'm seeing the wisdom in it, that he was allowing me the time to connect with him and truly be on the same page.
The Ramsey Show
Small Changes Now Mean Big Wins Later
At the same time, say, oh, then the breaks. This is what it's going to be. You don't have to like it. It's fine. We're doing it. Yeah. You don't have to like it.
The Ramsey Show
Small Changes Now Mean Big Wins Later
Yeah, I like to teach that when you set out to win an argument, you begin to lose the relationship. So if you and I were in an argument, and I, as intelligent people do, we like to send that zinger, that thing that's really going to make the point hit home and zing and hurt them. Congrats, what have you done? You still have to live with this person.
The Ramsey Show
Small Changes Now Mean Big Wins Later
You probably still have to work with this person. You've now just won to be first up to apologize, most likely. I mean, you've now just had to, you've earned that awkward silence when you still have to pass them in the hallway. When you set out to win an argument, you only win contempt. You have to see things as something to learn rather than something to prove.
The Ramsey Show
Small Changes Now Mean Big Wins Later
Rather than pushing my point, I want to learn more about why you believe what you believe. If I have my glass full and you have your pitcher full, I got to let you pour it all out before I can ever pour anything of what I have into you. And so it's being curious before you start just pushing my way, my way, the highway.
The Ramsey Show
Small Changes Now Mean Big Wins Later
You got it. I mean, and that's why in the book I set up this framework of how I teach communication is that when you say things, you're going to say it first with control, and you're going to say it with confidence, and you're going to say it to connect. When you really have those three main pillars to communication, it's going to set you up much better for success.
The Ramsey Show
Small Changes Now Mean Big Wins Later
I like to say that most people don't know what they're saying until they're already talking. And so what this book allows them to do is have a GPS and point true north.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
Yep. Listening and, uh, have been a, uh, been a student and, and followed David's principles pretty well. So, um, you know, I'm pretty happy today. I've got a lot of peace and contentment, a lot of blessings in my, in my life. And that kind of leads me to the call today. Um, so a little backstory.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
So I, you know, I live, uh, I'm retired, um, about two years ago and, um, I mean, I've done well in the market and I was in business for 30 years and, um, situation I have is, is on behalf of my daughter. So, My daughter has been married for two years and a beautiful family. They have two little babies.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
Um, and uh, my son in law, um, very bright, intelligent young man, a daughter's very strong willed and independent. Um, is some of the principles that are laid out, you know, they haven't followed to it. The combining, you know, finances, et cetera, is one of them, which I was always very vocal. I kind of taught my daughter baby steps. Um, and so she's been a disciple. She's getting there.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
She's got her, She's got an IRA. She's got her emergency fund. She follows a very strict budget. But then not having joint finances, we just found out this week, my son-in-law came to confession to all of us and had been day trading. And essentially was financing some of this through credit cards. And he stacked up about $60,000 in debt and lost all of his savings.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
Day trading. And so that number doesn't scare me so much because I'm confident that they can work their way through the debt. The part that I'm struggling with as a father and a grandfather is I'm trying to stay in my lane to give my daughter as much support as I can. She's never asked anything from me since she's graduated from college. She does well at her job.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
In fact, she starts back to work from maternity leave this coming Monday.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
Yeah, born in October. Beautiful little girl. So the challenge is, for her and for me, is all of this was hidden. She had no idea until she stumbled across some information looking at her credit score that had dropped.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
and found out that one of the her card he had used and stacked and maxed that out and that's how she found out and got it so it's a truck so he used her card without her knowing it so they they are very the best way i can put it their family's very close as far as the kids they don't do anything other than take care of the kids and activities are great parents um
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
And unbeknownst to her, yeah, he used her card, and they do that. They might use each other's cards at times. But then he maxed it out, and when her credit score dropped by 20 points, she started digging.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
Yes. So he confessed to her and then the day after called me because, again, we're very close. I mean, we talk consistently. I talk to my daughter or text almost every day or we FaceTime. Yeah.
The Ramsey Show
Don’t Let Toxic Money Situations Keep You Trapped
She's about to go through divorce, right?
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
Hey, guys. Thanks for taking my call.
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
So I'm powering through the baby steps. I'm about halfway through baby step two. I'm paying off all my debts. And I've gotten to my next smallest debt, which is my wife's student loans. There, uh, the balance is about $8,500 and with our debt snowball, we can kill this in about four months and I'm ready to do so. But there's a caveat that I can't find the answer to.
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
So it went into default before we were married and we have now entered a loan rehabilitation program with the department of education. And the deal is if we make nine months of consecutive payments, They'll remove the default status from the loans and transfer it back out to a normal servicer.
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
So unless with two options, either a, I can get snowball this and kill it in four months, but I'm stuck with that word default on my credit history, even though it's a paid in full account. Or I stretch it out, keep accruing that interest, and go through the program to remove the word default from my credit history and just do it that way.
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
And I really don't know which one's more, or I should say less harmful to me.
The Ramsey Show
The Road to Financial Freedom Is Paved With Grit
Okay, you don't think it'll haunt me when I try to get a mortgage in a couple years?
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
We helped him work out a structured repayment plan as a condition to him coming back and getting into insurance, and that's been paid through wage garnishments since then. I discussed with him before he came back the need to stay on top of his taxes and finances because he's never been good with money.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
During that period of time, many times I'd ask him if he was on this and he'd just blow up and wouldn't talk to me about it. Three months ago he called us and told us that he was in tax debt to the IRS again and wanted his mom and I to bail him out basically using our share of our estate when we die. We thought he probably owed about $50,000 or $60,000.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Turns out he hasn't filed any state or federal tax returns for the past four years, nor has he paid any estimated taxes for 2023. We're meeting with our accountant next Thursday to go over all this to get specific numbers, but I'm guessing from what I've seen, it's going to be over $200,000, and about half of that is just interest and penalties.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
He also hasn't paid any 941 withholding or state unemployment tax. He has no business being self-employed, obviously. So my question is, we have the assets to do that, but we would have to sell off property and mutual funds. I don't know if you need our income or what exactly.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Net worth is probably about $2.3 million. And about roughly half of that is in two pieces of real estate, our residence here in Indiana and another home we own in Florida. I'm sorry, Jeff. Including the real estate, the majority of our assets are in IRAs, Roths, and 403Bs from what my wife taught. We've got about $130,000 in a money market fund.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Well, he just resigned from that position because after he took it over, he ran it into the ground. He couldn't make a go of it. Right now he's doing a sales job, and it seems to be going pretty well, but he's only been doing it a couple of months. He's making about $75,000 a year plus bonuses.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
He's not married. He has an 8-year-old granddaughter that we absolutely love and spends a lot of time with us. He was going to get married, but they did it kind of reverse. They got pregnant first, and then they didn't get along, so they didn't get married. So both of them are here in town, and both of them have jobs or own businesses. And they get along fine. We all get along fine.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
I actually worked for a captive company, so they actually owned it. And when I left, they paid me a percentage of my renewals, and that's one of the cornerstones of my retirement now. So I didn't have a say in where the policy was.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Not all of it, because it was a big agency, so they split it up among other agents. They gave him about half of it.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
I don't think he owes. He rents. He doesn't own a home. I don't think he owes anything else. He doesn't have credit card debts. The tax debt's the only one that I'm aware of.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Yeah. The thing is, Dave, this has happened so many times, I can't count them. But you've been there to bail him out every time. Yeah, and we had to take him out of high school because of his behavior. We had to send him out to a survival camp in Idaho. Then we put him in a private school in California, and all that required a second mortgage on our house at the time.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
We bailed him out of a car loan that he didn't keep up with that I co-signed for. It's just been one thing after another.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
If it were me, I wouldn't do it. Here's what I'm going to suggest. He got a severance package from the insurance company that's going to pay out about $30,000 over the next five years, about $6,000 a year. I told him that we would help him out if he would sign that over to me to pay back what we're going to advance him, but I initially thought we could do the whole amount.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Thank you. There's one other question to kind of take this out a little further because I don't think my son realizes how bad a position he's in. If he pays this over the next 20 or 30 years, he still may not have it paid off and we die. And that's all right. Yeah, but we have all of our assets and our real estate is in trust. And my daughter is the trustee and the executor.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
And we currently put a clause in our will that allowed my son to take our house here as part of his settlement of the estate because he loves our home. but I'm concerned that if he doesn't have this paid off, I don't even know that I want to leave that share of the estate to him because I think the IRS could put a lien on that.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
Yeah, and I want to make sure that, I mean, ultimately it was for him, but it's ultimately also to go to our granddaughter, and I don't want to... eat up our share of that estate.
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
my wife and I are in our early seventies. Uh, my son lives about a mile from us. He's in his early forties. He relocated back here to Indiana from California about 11 years ago from LA where he was working in a music business. And, uh, he was going to take over my insurance agency a few years, uh, retired about nine years ago. So he did take that over. Um,
The Ramsey Show
Debt Isn't The Problem - Your Mindset Is
He got into tax problems when he was in California because he was working for a music composer that actually treated him as an employee but paid him as an independent contractor, so he didn't know anything about paying taxes. Got behind with the state and the IRS. Ended up owing them $30,000 or $40,000, I think.
The Ramsey Show
Money Is a Tool To Create a Life You Love
Thank you. Thank you. Thank you. Thank you.
The Ramsey Show
Money Is a Tool To Create a Life You Love
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The Ramsey Show
Money Is a Tool To Create a Life You Love
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The Ramsey Show
Money Is a Tool To Create a Life You Love
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The Ramsey Show
Money Is a Tool To Create a Life You Love
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The Ramsey Show
Money Is a Tool To Create a Life You Love
Well, the kids, I will say the kids... do not want for anything, but they also have got reasonable expectations as well because we've tried to, you know, raise them to not want what everybody else has.
The Ramsey Show
Money Is a Tool To Create a Life You Love
Well, you know, the oldest one, the 17-year-old, you know, it depends on the day. But the other two, you know, they're under 12. So mom and dad are still pretty awesome.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Hello. So my question is, first of all, thanks for having me on the show.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
I have a question that I don't think has been asked before. So I can't invest in the S&P 500 and other similar ETFs because of religion reasons. So should I create my own diversified portfolio?
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
So the reason is I'm Muslim, and I'm not allowed to invest in any companies that involve alcohol, gambling, adult entertainment, all those things.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
So first, I found another ETF that pretty much is like, pulls from the S&P 500, but excludes the company that do the gambling and alcohol and all that stuff. But the problem with that is the expense ratio is so much more higher than it would be for investing in the S&P 500. Is this in a retirement account? No, this is personal.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Yes, but through work, like 401k and stuff like that.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
I believe it's 6% match, and I'm doing 100% of whatever 6% is.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Yes. I contributed one time, but then I stopped because I really wanted to take advantage of tax reduction.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Well, really the 401k is something that I was contributing to already unknowingly. And I just realized how much I had in it. Right. I still haven't made a decision whether I want to stop contributing and like go full on the other direction. But right now I know since it's like my only option at work and it was already automatically being contributed. Right.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
That's not something that would be hold against me religiously.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Yes, they start at like 2.5 or 2.0. It's really high.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Well, do you think if I decided pretty much to actively, so I create my own portfolio that operates as a passive ETF kind of thing, right? I only pull from the companies that I do align with from the S&P 500, NASDAQ, and all that.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
I would only pick enough to have my portfolio diversified. I wouldn't go all the way into like presenting those 1% companies and stuff like that. I would worry about the top 10 and then the ones that come underneath. But when it gets to like that company that's like 0.5% of the S&P 500, I won't worry too much about it.
The Ramsey Show
It’s Time To Cut Debt out of Your Life!
Even if I'm picking the stocks, not based on what I believe are good investments, but based on what the S&P 500 is picking.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Is Rachel on the line, too? She's not. We just had our second son, so she's taking care of the baby right now.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
$1,020,000. So just right over that mark.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, so it's about $400,000 of real estate. We actually just paid off our house in October of last year, so we just paid that off. Way to go. Yeah, and thank you.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, and then we have about $500,000 in just investments, like different types of retirement funds, and then about $100,000 split into other assets, like $50,000 in cash for emergency funds, and then cars and other things like that as well.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
We're 33. Both of us are 33.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Thank you. So last year was one of our best years. We just made $330,000. Whoa.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
It was right out of college, about a little less than $80,000.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, I'm a sales rep for a software company, and my wife is a stay-at-home mom, but she also has her master's degree in marriage and family therapy.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Did you get a college degree, four-year? I did, yep. What was it in? Mine was in business finance.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, mine was about 3.3. Okay. And your wife? She she's got her master's and she's got a 4.0 in her master's. I had a feeling 3.4.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, so it's funny. It's always been a focus of mine, but we weren't really super intentional about it until about two years ago when our first son was born and my wife stopped working and things got really tight. We had a car.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
payment we had the house and all these different things and my wife and i we found ramsey while we were going through church and we got really intentional we combined everything we paid off our car quickly we and then we got really diligently focused on paying off the house and we paid off about 270 000 in two years whoa just really focused on intensity of you know making sure that we got that house payment done so this way
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
If we want to have more kids and my wife wants to stay at home, we've got that flexibility to do so.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
It was about 3.5%. Wait a minute.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Yeah, we've heard it all. We've heard it from a lot of coworkers, friends saying, you know, you're crazy for doing that. But the peace that we have, you know, now that we have our second son here and we don't have to worry about things, we can just choose to do whatever we want to do with our money and, you know, choose to do whatever we want to do with our life. It brings a lot of peace to us.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Absolutely. Absolutely, we do. What do you tell them? We also... Well, we just tell them the piece that, you know, that we have, um, about, you know, having a paid for house, being able to make decisions about what we want our life to look like in the future just brings us so much joy and that it's not about the, like, it's about the money of course, but it's not, it's not about the interest rate.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
It's not about that tax deduction. It's about the piece that comes with our house and the ability to make the decisions that we want to make for our family. Yeah.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Couldn't have said it better myself.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
We got a small gift from my parents to help pay for the down payment of the house. It was like $23,000, but that's it. Okay.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Thank you. Thank you.
The Ramsey Show
The Baby Steps Break You out of the Paycheck-to-Paycheck Cycle
Thank you. Thank you.