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A
Hindsight really is 2020. Today, Scott and I are going to look back at how we both would adjust our retirement planning if we had to start all over today, both at our current ages and if we were 23, spoiler we might have done things a little differently. Hello, hello, hello and welcome to the BiggerPockets Money Podcast. My name is Mindy Jensen and with me as always, is my probably would change some things co host Scott Trench.
B
Thanks Mindy. I look forward to looking back today here on the Bigger Pockets Money podcast with you. I'm super excited about this episode. This is just a fun kind of what if scenario. I think there will be a couple of what ifs. Like what was our journey like? Will we have changed anything in our journeys and then how would we approach it if we were starting over today? And I think that'll be a fun discussion here. So Mindy, can you give us the quick 60 second overview perhaps of your journey to fire for folks who may not be familiar with it?
A
So my husband and I started investing in the late 90s basically because we're saving for retirement. He worked in tech, so our portfolio has always been tech heavy, like up and coming tech heavy stocks. We were also live in flipping. So that's when you move into a house that is unattractive and you make it really beautiful and updated and then you sell it. You have to live there for two of the last five years in order to pay $0 in capital gains taxes. So that is also what we did. I became a real estate agent in 2014 to help us find these properties. I had no intention of being a real est agent but then I started helping friends and then I started helping friends of friends and real estate agents make a lot of money. This is a really great and fun for me way to generate a lot of income. So as Carl left his job we weren't tapping into our retirement funds because I had the real estate agent job that was generating income as well as finding a dream job at this little tiny company called biggerpockets.com so Scott, how did you get to fi?
B
I love it. If I would summarize what you just said there about your journey. There's a frugality component for a long time. There's a handiness in working on live in flips, which is a substantial boost in income over and over and over and over again that is very tax advantaged. There's a good, maybe not incredible top 1% household income from Carl's tech career. And then right as he was leaving his job or in that period there was a little bit of overlap, but. But as he left his job, you had the job at Biggerpockets and this agent income that was more than enough to support your family and that allowed this aggressively invested, well positioned tech portfolio to just balloon to way past your fire number. And that's awesome, right? Is that the story in a nutshell.
A
You think for you it is, except I wouldn't characterize it as top 1% income. I would characterize it as top 10% income.
B
Yeah, yeah, it was not top percent 1% income, but it was good but not incredible. Elite income that drove your journey to fire was these other moves in combination with enough in frugality.
A
Yes.
B
For me to answer your question. You know, I, I, I, I had everything go right, right. I, I graduated from college in 2013 and I had three grand or whatever cash remaining after a trip to Europe. No debt, very fortunate. And I started my career and the playbook was handed to me. You said that there wasn't all these people talking about this. Well, they were by, by 2013. Mr. Money Mustache outlined everything you needed to do to become retire early. And I just had the privilege of learning all of that and learning from bigger pockets about real estate. So I avoided making any really large mistakes with money. I didn't spend aggressively and I was able to accumulate about $20,000 in that first year. I bought a house hack. The market's obviously done really great over when you take the last 10, 11 years in context for that, I bought multiple properties over time. I joined a startup at Biggerpockets, which was a rocket ship and won the lottery as we talked about briefly earlier. And I had the opportunity to just really make pretty good, I think overall decisions on the spending front, on the investing front. Most of my wealth was invested in stocks and real estate and join a business that had incredible opportunity for my career associated with it. So I had all these levers. We talk about spending less, earning more, investing and creating assets. I just got a wonderful 10 year journey of maximizing my learning and opportunity in all of those areas basically. And that made it, relatively speaking, easy and straightforward for me to achieve fire over that period of time.
A
Scott, what I'm hearing you say is you took action. You didn't just sit around, you didn't spend every dime that came into your pocket. You were looking for a different way, you found the different way and then you followed the different way. I think that last point is a point that we cannot beat home enough. You have to take Action. It's one thing to find Mr. Money Mustache, but it's quite another to actually do the things necessary to make it to early retirement.
B
I certainly will give myself credit for acting on a lot of these things and then thinking about them, obsessing over them, learning and trying to optimize or improve in all these areas and stay in tune with stuff. But I also did have the fortune of just like, oh, here's the obviously correct playbook. And then the wherewithal to realize, yes, that is obviously correct. I'm going to do that. I've definitely made mistakes along the way. We'll talk about those. But none of them have been major blunders at a strategic level that have really meaningfully blocked or delayed my journey to fire.
A
Okay, Scott, so that is how you got there. Starting at age 23, let's pretend that all of your wealth has been wiped out or you never had any to begin with. And now here you are at age 35. What would you do different?
B
Yeah. And I think context matters. Right. Because I was single in 35, I'd repeat a lot of the same things in the same way. Right. I know some folks who, for example, have been divorced and are starting over. And there's a lot of parallels between that journey and the journey I could take as a 23 year old at that point in time. But as a married man with two children right now, I would say I would not be as aggressive about the pursuit of fire. Right. There's things that are more important than the pursuit of fire. And I would recognize that living in a more safe or more, you know, welcoming or more nurturing environment where family memories are going to be made than a house hack in the up and coming part of town would probably be higher on the list. I'd probably be more cautious to leave a career. I'd be more dependent, I guess, or more willing to depend on the benefits that come with a career. I'd be more focused on that. And so I think there'd be less of an entrepreneurial itch and a bit more. And I think I would just extend the timeline. I think I would still make frugal decisions on the car purchase. I'd look for a live in flip, maybe something light or those types of opportunities, or maybe like a higher end house hack certainly would consider those. We did, of course, live in one of my duplexes just like that for a year before moving into our permanent home here down in the suburbs. So I think I would do some of those things and I think I would still follow most of the other playbook items like the order of operations, but I wouldn't be saying, oh, I'm starting from scratch with maybe 100, 135,000 household income, perhaps situation. I'm starting from that situation. I wouldn't be like, oh, I'm going to fire in 10 years. In that situation, I'd be like, the timeline is going to be a little longer if I'm starting from scratch and I'm going to have to really keep my core expenses low, but also balance the need to take that income and provide a good quality of life. Now, in combination with you're trying to get ahead for more traditional retirement. So I'd be aiming for something more in like my late fifth, my mid to late 50s than my 40s. If I was starting over at 35 and trying to build wealth. Lindy, what would you do if you were starting over today here at your current age and with your current family dynamic?
A
So my age, I am 53. My family dynamic is my oldest daughter is in college and my youngest daughter is in high school. With our family dynamic, I am paying for my oldest daughter's college degree. And if I was Starting out at 53 with essentially a $0 net worth, I would not be paying for her college. I would have her get student loans that hopefully I could help her pay for later. But right now I would focusing on getting myself to retirement age. Traditional retirement age with enough money to retire or close to it, that's 12 years from now is traditional retirement age for me. So I would be getting my real estate license. I've had my license for 13 years now. I would, if I wasn't already an agent, I would get an get a license and I would be doing everything I possibly could to find new clients to help buy and sell real estate. My real estate partner, Libby Earthman, has a really unique way to approach open houses that generates a lot of leads for her. I would also emulate that because without the unfair advantage that I have of being a podcast host and my husband has a blog, you know, I live in Longmont, Colorado and a lot of fire people want to move to Longmont, Colorado. I get a lot of leads that way. But if I didn't have that, I would go and listen to episode 64 of the Agent Goldmine podcast and see how my friend Libby does her open houses because she has generated so many leads from her open house strategy that she now can't take my extra leads. So now I have to look for another partner. But but getting a real estate license I think would be key to generating extra income. There's a lot of different side hustles that people can do. I think real estate agent is an excellent side hustle or even could be your full time job if you are, you know, generating enough money from it. And now a quick word from our sponsors. I love math said no one ever. Nobody starts a business thinking you know what would make this more fun? Calculating quarterly estimated taxes. But somehow every small business owner ends up doing it. Your dreams of creating, selling and growing get replaced by late nights chasing receipts, juggling invoices, and wondering if that bad sushi lunch with Scott counts as a write off. Change all that with Found. Found is a business banking platform built to take the pain out of managing money. It automatically tracks expenses, organizes invoices, and even preps you for tax season without you doing the heavy lifting. You can set aside money for business goals, control spending with virtual cards, and find tax write offs you didn't even know existed. It saves time, money and probably a few years of life expectancy. Found has over 30,000 5 star reviews from owners who say Found makes everything easier. Expenses, income, profits, taxes, invoices even. So reclaim your time and your sanity. Open a Found account for free@found.com that's f o u n d com. Found is a financial technology company, not a bank. Banking services are provided by lead bank member fdic. Don't put this one off. Join thousands of small business owners who have streamlined their finances with foundation.
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B
Right? Welcome back to the show. I think that what's interesting there is what I did is I went all out on financial independence when I was 23. And what I'm hearing you say is you would do the same at 53. And I think that that's right. We talked about Barb, this fictional Persona we created a while back called broke at 50. On an episode called broke at 50, retired at 60. You know Barb is broke at 53 and starting over. What do you do? Well, now that it's, the context has again changed and now there's a very real risk of not being able to live a comfortable retirement. And that fear, I think would change everything about what I just said and make me want to go all out to build wealth and really build a strong, fortified financial position in whatever capacity I could. And then I'd be forced to be very frugal once again and I'd be forced to look for all these entrepreneurial opportunities to make more money, perhaps as an agent, perhaps as some other sales role. And I'd be forced to consider serial house tax and real estate. And my family's comfort, I think would then come second again because you're not, you're thinking more time than you know you have less time. Right. And I would, I would not want to put myself in a position where my adult children would then maybe potentially have to support me later in life. I'd want to take care of that now. And that would be worth the trade off of the less stability or less, you know, consistency in that, in that environment. That's how to imagine things are. Is that what you're saying to a certain degree here, Mindy, with this?
A
That's exactly what I'm saying. And the reason is, Scott, look at your single self and my current self. You were single instead of married, but you didn't have any kids. I have a daughter in college in California, so she doesn't live in my house. I have another daughter who can drive herself who honestly doesn't want to hang out with mom because I'm not cool anymore. So while I would prioritize still connecting with her, I'll have a lot of free time to do things to generate side income and, and you know, the hustle because she's out with her friends. You as a married 35 year old father of two small children, have a very different family dynam than I do right now. So, you know, you want to prioritize spending time with your two year old and not quite one year old and that's great. When, when I was 35 I also did that. But now that essentially my kids are almost out of the house or one of them is out of the house, I have a lot more free time to do this hustle. I don't think I would house hack, but the live and flip I might continue to do.
B
I think the times to pull all those levers and go really hardcore are when you're young and single. And then when you're, you know, maybe, maybe a little older and the kids, you're starting to get close to that empty nest, or even if you're not quite there yet, is there a way for your kid to go to the same high school at least and for you to house hack or find those opportunities to, to build wealth in every lever you possibly can to get ahead if you're, you know, broke and starting over. Like that's the context we have here. Now there's a whole sliding scale here. If you're close to fire and you're, you know, 33 and you have a little one like finish the play and go do it right if it's a year or two on there. But if it's, if it's, if it's going to be a consequence to your family for a very prolonged period of time to defer the life you really want, just to retire a few years earlier, maybe I wouldn't make those trade offs. And I think that's the nuance that's come into the discussion for me in the last 10 years. When I wrote Set for Life, for example, the first time, I had no room for that nuance at all because I was right and 26 at that point in time. And when I revised it a few years later, five years later when I was 30, 31, I was able to put that nuance back in to the revision of it because there is that nuance. But I do stand by and think that it's so valuable to go all out in those first years, out of college in particular, because college and the lifestyle you want when you're like in your early 20s is not that expensive. And as long as you don't just assume this overhead of the car and the fancy apartment or the house, I mean, you can just have all the fun and build all the wealth. Just don't make those big mistakes and go all out for those couple of years. You're going all out anyways at your career, almost certainly, and regardless which direction you choose. So why not do it in a way that sets you up to become financially independent? Because it's so great to get to that point in your 30s, if you choose to. And when you start a family, I.
A
Think going all out when your family dynamic allows for it is going to be the difference between really, really generating that wealth and that income or kind of just bumping along.
B
What would you do if you're starting over at 23? So not this time you're not, you're not 53, you are 23. You're starting over today here in 2025.
A
Okay, if I was 23 and starting over in 2025, I would again get my real estate license because there is just so many opportunities available to generate a lot of income as a real estate agent. I would invest in the stock market and I would create the habit of investing in the stock market. Starting today I only have five extra dollars. This month I'm going to throw that in the stock market. I only have 25 extra dollars. Next month I'm going to throw that in the stock market and then I' going to look for side hustles that I can do to generate more income that I can put towards my retirement. I want to be able to max out my Roth IRA. I want to be able to Max out my HSA. I want to be able to max out my 401k, assuming that I have a traditional job that provides me with a 401k. If I don't, then I'm going to look to the Roth IRA for that opportunity. But also if I can generate some self employment income, I have the opportunity to contribute to a solo 401k and that opens up even more amounts of money that I can contribute to my retirement accounts. I'm going to look at investing in after tax stocks so that I can generate ways to create income after I retire that are outside of my traditional retirement accounts so that I'm not falling victim to the middle class trap that I learned about on the this podcast called Bigger Pockets Money. How about you Scott? Today 2025, you are blessed with only being 23 years old. What would you do?
B
I'm in agreement with you and on every level I'll just frame it differently at the strategic lens and I'd say the next 30 years is going to result in something really interesting. And I think for some people, very wonderful outcome here, right? AI is there's every reason to believe that AI is going to increase crop yields per, you know, per acre. It's going to make efficiencies come down and distribute distributing scarce resources and goods so that real costs fall over time on there. And I think that it's going to enable this fire community. I think that if anything the stakes are so much higher to get on the other side of the capitalism equation early in life than they ever have been. Because the bifurcation between the life you're going to have at 30, 35 if you build wealth and participate in the growth of the economy is going to be so Much greater. So incredibly bifurcated from the people who don't focus on those skill sets and kind of spend every dollar they have and don't really see their careers blossom. I think it's going to be so incredibly different that the stakes could not be higher. It's the difference between basically doing everything you want and having the world as your oyster and not having a lot of options later in life and being kind of stuck and trapped into a place that's really hard to get out of, treading water. I think it's the same situation that I kind of unfold in the last 10 years, but maybe with even a little bit higher stakes now. And so I think that the strategy is really keep those expenses low, invest in ways that will participate in that economy. I think there's every reason to believe that companies are going to grow over the next 10 to 20 years. And I would be having fear in a way I maybe didn't have or wasn't as acute when I was 23 back in 2014, around the valuations of the stock market. So I might be even more inclined to really make that house hack a priority before those stock investments for the first year or two. I'd probably be saving that in cash and getting ready to do that. There's a little bit of market timing that I'll get poo pooed on, but. But that would be probably how I'd be thinking about things in the current market. At least you're not buying at the top of the real estate market in a lot of these metros. And I think that I would be really interested in entrepreneurship. I'd be thinking AI is a real threat to the types of work that used to be rewarded by 10 years of experience in a company like doing financial analysis. That's going to be really hard. The guys who are already experienced at financial analysis probably fine. But the new guys trying to get into it are going to have a really hard learning curve to get good enough where their skill set is more advanced than what an AI can produce. And so I'd really be thinking about entrepreneurship and becoming a jack of all trades in all these different categories. Because those opportunities I think are going to move quickly. There's going to be a really big opportunity. You're going to make a lot of money really quickly if you're an entrepreneur skilled in AI in this area. And then it's going to close after six months or a year and then the next one's going to open up and that's going to close. And I think that's the kind of skillset that I would be developing, is how do I really get good at trying? Lots of experiments very quickly with this entrepreneurial hat on in order to get there. So I think low expenses investing like we talked about and entrepreneurship, all underscored by the sense of urgency about the stakes being very high for getting the other side of the capitalism equation and building a financially independent portfolio early in life.
A
I like that, Scott. I like the urgency because I want to encourage younger people to be focused on where they're putting their efforts instead of just letting life drag them along.
B
In a more practical sense, I'll put it this way, right. It's the playbook we've talked about. We talked about this for Joe Million Times. For Barb, it's keep your expenses low, work your job, make sure that there's a baseline there. Don't depend on it. I wouldn't model out my career growth the same way I would 10 years ago. Maybe it'll be better, maybe it'll be worse, but I'd measure it in a much more volatile fashion. Boom and bust for a lot of folks that are starting their careers now. And it's about keeping your expenses low and saving the booms if that comes to pass, and making sure that your expenses are lower than even the really lean times in there. And I think that if you do that, there's a really good chance you become very, very wealthy very, very quickly if you play your cards right and look for those opportunities. So that's the kind of core underpinning of the playbook. And then house hacking always helps. That's a great steady flow of income. Keeps your high probability flow of income or lower expenses. And then of course, broad based diversification across companies and participating in the growth of the economy.
A
I think that we can't discount that too much. Participating in the growth of the economy? Yeah, we're probably heading for a bit of a dip in the stock market, but overall, I have faith in the long term viability of the American stock market in the American economy. So I would continue to invest in that.
B
Mindy, what are some other things that you'd be thinking about if you're starting over and you're 23 right now? In today's economy, what are some of the things that you'd be looking at or telling yourself to explore as trends to bet on with your time and energy over the next 10 years?
A
Ooh, trends to bet on. You touched on it, Scott. AI. So I would be looking at AI companies to invest in. And I would be looking for jobs that are AI proof. So I don't think that AI is going to be taking over health care in the foreseeable future. You need a doctor to take your information and process it. Yeah, you can throw it into AI. But right now AI has a lot of mistakes. Other jobs that can't be replicated by AI, I think again, the real estate agent. I keep coming back to this because I think it's really, really valid. Scott, what are some other jobs that are AI proof?
B
I don't think any, any job is going to be AI proof or whatever. I think, I think that people forget, you know, there's no more horse and buggy drivers and that's a good thing. Right. For the most part. Right. Like that. Like those jobs got moved into other parts of the economy and, and change is always, it's going to, there's going to be losers and it's going to be very acute and very painful here. And I'm not trying to take away any of that pain that is going to be real. When jobs are displaced by new technology and opportunities emerge from that. And that's where my theme is, the Jack of all trades mentality of using this new technology, looking for those opportunities and pioneering them and being ready to move and evolve very quickly. That is what's going to get rewarded over the next 10 years. Over the attempt to master hard skills in one or two years. Right. Two years of experience is not going to cut it in something like drafting HR policy or financial modeling. 15 years of experience might. That's different. That's where real experience and real pain and wisdom and understanding long term trends to bet on and what to prompt the AI with and challenge the assumptions underlying things is going to, to be in there. But the mechanics of building a spreadsheet, those are not going to be rewarded over time. The mechanics of being able to learn AI quickly enough to then help you master building a spreadsheet are. That's what I think is the difference from a nuanced perspective. I'll also challenge like you're talking about. AI is not going to replace doctor. AI has not replaced my doctor, but kind of has also replaced my doctor. Like I have this whole like document that I've built because I'm a true nerd. This is surprise no. 1. It's called my late 30s health and fitness protocol. I have my goals, I have my weightlifting regimen, I have my running regimen, I have my diet, I have my recovery, I have my supplementation, I have My skin and healthcare routine. I've got my preventative screening and labs that I'm gonna get and all that. And this is all developed through self education and AI and I post put it in there and ask it for tweaks. And sometimes it gives me right answers, sometimes it gives me wrong answers, but always gives me more things to research. And that's a really big benefit. I don't know if I could go to the doctor and get something as helpful as that because it combines these goals of powerlifting and supplementation with best practices from a healthcare perspective. That's a real threat to a doctor or healthcare provider, I think.
A
Yes, but that's not what I'm talking about. I'm talking about, oh, do I have strep throat? Am I having a heart attack right now? Your AI can be like, okay, yes you are. What is AI going to do about it?
B
I stubbed my toe really badly last week, like two weeks ago. Yeah. And like it was black and blue.
A
I'm not laughing that you stubbed your toe. I'm laughing that you comparing a stubbed toe to a heart attack.
B
So I took a picture of my toe and I sent it to Grok. Right. The AI and Virginia made fun of me. You know, this is this. And I also sent it to my doctor and they both told me the same thing. That's pretty black and blue. That's not looking good. But I don't think it's broken. Come back in two weeks, see if it's feeling. Phillip flies now. Feels so like, I don't know, you know, that's a tough, like this is all real, like what's going on with it. And I think that there's a fear and apprehension for the unknown and I think there also should be really big excitement. Somebody's going to win on that and it's going to be the 23 year old who is always looking for the opportunities to get better with it, learn from it and master it. I submit investment ideas to the AI all the time to beat them up before I talk about them with other humans because that gets me my most stupid mistakes out of the way quickly.
A
What about skilled trades, Scott? We're talking about electricians, plumbers, roofers, H vac technicians.
B
Yeah, that I think is safer, relatively speaking, at least for longer until Elon Musk builds his 1 million robots that he's promised with his trillion dollar pay package. So I think that that's there. But one of the things that's been bugging me about the trades is if you asked me two or three years ago, what's that going to look like? I would have said it's going to be a big boom for the next two or three years. Like they're, they're going to make a killing. It's going to look like the best thing in the world because he had so much construction going on. We just delivered record new supply of multifamily. There were cranes everywhere two or three years ago and now that is stopping and slowing. And so I would have said, you know, when that slows, what's going to happen to all these people? Right? That's the nature of some of these industries is they boom and you can't hire a worker, you cannot get a contractor and then that slows and contracts and then what do these people do? They're going to fizzle out. It's actually a huge problem in the construction industry in a general sense because it's very hard to find very long tenured construction workers who have been buildings because the developers build and they bust. And then these people stop working in those trades because they want something more stable. And there's very few really skilled contract supervisors, contractor supervisors who can build these large projects. So that's actually a well known problem in the space. But what's weird is this year that hasn't been happening as these projects have slowed. You're not finding those costs in labor savings to be there. I mean, I'm getting mixed bag from local developers in Denver when I talk to them. But you're not really seeing that in the same way. And I think a big piece of that has to do with the changes in immigration policy at the national level that have been maybe impacting the pool of construction labor to a certain degree. So I think that's a real risk in those trades that that's going to happen is there's a boom and bust cycle that you're subject to that's not really related to AI. So I don't love it. I think there's a lot of oh, just go to the trade school and do that. And that's great. That was great two years ago it seemed awesome. But I'm not sure if I really ever fully bought into that mentality. I think that the college education is still king for me and it's just the degree matters more than the school from what we talked about with Preston Cooper. So I'm not really go get into the trades as much as some people are.
A
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A
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B
I think it's awesome to just do this show with you because of the differences between us and our experience set. And I think, you know, reflecting on your journey, you went to school, you've said this many times for fashion design, right? And do not believe that was a high ROI choice. It did not lead to good opportunities directly. I studied economics, corporate strategy and finance. Finance at Vanderbilt, Right. And no question did that set me up for a good set of opportunities, a large number of potential job opportunities, and made me more attractive candidate to Josh Dworkin when I joined BiggerPockets initially and provided a lot of background knowledge that was helpful. Also a good network of people like my business partner on my rentals went to Vanderbilt with me. Right. And he's one of my best friends. And that's, that's an advantage there that I wouldn't have had if I had gone to school for fashion design. And I think that there's almost no way that it could have gone a different way, but there's almost no way. You go to a good skate school or a good private school like a Vanderbilt or University of Maryland in there and study one of these professions and don't have some kind of subset of better opportunities if you go after them than going into trade school. I think to a large degree not to say that trade school is bad. I just think, and I get that college is not always jam like you said. But I'm not sold on the college is dead yet. I'm sold on college as an ROI based decision. And for the people who it is for, it can be very ROI and the best choice by far if they apply themselves and then pursue the opportunities that come from it and actually get a high ROI degree. Agree.
A
Absolutely agree with that. I was not saying the college is dead. I do not believe the college is dead. I just, I come from the time period where we told everybody after you graduate high school, you go to college. There's no other option. So the people who didn't go to college were like, look down upon and oh, you're not going to college. Really? You're going to ruin your life. And Tinian Crawford is a great example of college is not for everyone. And that's okay that it's not for everyone. You can still make a good living even if you don't go to college. But yes, their college is a great choice for a lot of people. I'm definitely not saying that. I can only imagine your clothing design. Scott, you should have gone to school. Hey, you can go back now. Go to go to school for fashion design.
B
Mindy, I'm now doing a lot of design for the BiggerPockets money website. I'm having a blast doing it. This is always something that I never could get my head around. When I was CEO at BiggerPockets. I had a lot of fun doing that on BiggerPocketsMoney.com so go check that out if anybody wants to see my handy. My design skills at work to a certain degree on portions of that site. So I have fun with that now. But that's not been my. No, no, I would. That would not have been a good skill coming out of college.
A
Scott, are you looking for feedback?
B
Yes, I am.
A
How can somebody give you feedback on the website?
B
Oh, just email me@scottabickerpocketsmoney.com so I, I put that on almost every page that if you see something you don't like, let me know.
A
Scott, I thought this was a really fun conversation. I love that you would could do some things differently and some things the same. I really, really love that you would slow down your approach if you were starting now so that you could spend time with your family and give your kids yourself. I think that's an amazing suggestion and I hope that everybody listening who has small children is listening hard to that part of it.
B
I would even, you know, build on that, what you just said there and say I would say I would do a lot of the same things I did last time my time in my 20s. If I was starting over again in my 20s. I think the situation is actually quite parallel in some ways with the relative opportunities that were there. I don't think it's changed fundamentally in terms of what to do. I just think there's an even greater emphasis on flexibility and exploiting the new opportunities that technology brings, and that's going to really channel rewards disproportionately to the people who are able to spot and find those opportunities and get comfortable with the AI and comfortable with the idea of long stretches of low income with huge booms opportunities when they come up. So I think that's one. The other thing that I would say is there's a stratification of opportunity for this. Right. And I wouldn't be going all out with a family. I think that's one thing we've learned here is it's just not practical to put your family through a terrible grind. A death march defy is, I think, what we've learned, but it is so still valuable to put yourself through that in your 20s because you can still have fun and balance all these other things, things healthily at that point in time, or the stakes are just so high for not doing it in your 50s that you want to do it. So I think that's the really interesting nuance that we unpacked today on it. What about you? Is that. Is that the right summary for you in terms of how you'd redo things? It sounds like you would not go through that death march to Fi quite the same way.
A
Not when I have small kids at home, when I don't have any kids, or when my kids are older and either out of the house or, you know, don't think I'm cool anymore and don't really want to spend all their extra time with me, then. Then those are the two time periods that you can, you know, if it's not a death march to Fi, it's a very focused journey to Fi. Um, I still think the death march to Fi is really not the best choice. I want to have fun in my life.
B
Well, I had fun, Mindy. It sounds like you did, too. And thank you so much for a great conversation today.
A
Yes, thank you for always providing a slightly different point of view than my own. I love hearing where you're coming from.
B
From.
A
All right, Scott, should we get out of here?
B
Let's do it.
A
That wraps up this episode of the Bigger Pockets Money podcast. He is Scott Trench. I am Mindy Jensen saying Cheerio, Deario.
In this insightful episode, Mindy Jensen and Scott Trench, co-hosts of the BiggerPockets Money Podcast, reflect on their respective journeys to Financial Independence, Retire Early (FIRE), and discuss what actions they'd take if they had to start over in 2025. They break down their strategies for beginning again at different life stages (23, 35, 53) and candidly examine how family responsibilities, evolving markets, and emerging technologies—especially AI—impact their approach. The conversation offers nuanced, actionable advice for both young adults and those starting over later in life.
Mindy’s Story (00:56–02:01)
Scott’s Story (03:00–04:29)
Scott at Age 35 (05:23–07:33)
Mindy at Age 53 (07:33–11:13)
Both Agree
Mindy’s Playbook (16:07–17:45)
Scott’s Playbook (17:45–21:01)
Practical Takeaway
AI's Dual Impact (22:10–25:28)
Trades vs. College (26:35–36:59)
Emerging Theme:
Intensity in Early Years: Go “all out” in your 20s or when family and life responsibilities allow it.
Nuance for Parents: Avoid putting your family through extreme deprivation for the sake of early retirement. Strive for balance.
Urgency Later in Life: If starting over at 50+, urgency and prioritizing your future well-being (over funding children's expenses, for example) is essential.
Quote: “It is so valuable to put yourself through that [rigorous pursuit of FIRE] in your 20s... or the stakes are just so high for not doing it in your 50s.” – Scott (38:00)
Mindy adds: “I want to have fun in my life.” (39:26), underscoring the importance of balance over a “death march to FI.”
| Age/Stage | Key Moves | Mindset/Considerations | |------------------------|-------------------------------------------------------|---------------------------------------| | 23 (2025) | Get RE license, invest early/often, side hustles | Go all out, leverage low expenses, AI/tech shifting job market | | 35 (w/ family) | Balance stability & FIRE, career focus, moderate frugality | Timeline less aggressive, prioritize kids/spouse comfort | | 53 (kids older/indep.) | High urgency, maximize income (RE license/agent), frugality | Prioritize your retirement, may pause family support (e.g., college) |
The hosts agree: Life stage and responsibilities should steer your FIRE journey, not just numbers and spreadsheets. When you’re footloose or your nest is emptying, push hard toward FIRE. But when family needs are paramount, embrace a slower and more balanced approach.
Scott: “There’s an even greater emphasis on flexibility and exploiting the new opportunities that technology brings...” (38:00)
Mindy: “I want to have fun in my life.” (39:26)
For listeners serious about FIRE, this episode marks an essential listen, blending practical strategy with hard-won wisdom—and a reminder that adaptability, action, and context will always be more important than any one-size-fits-all FI formula.