MidLife Kicker
Welcome to Midlife Kicker— the podcast for those that have been moved out of corporate roles, but for various reasons, are not ready to retire. Our audience is made up of experienced individuals seeking inspiration and guidance for the next stage of their professional lives. We'll bring experts to the show with the purpose of helping you to succeed in this next stage in life.
MidLife Kicker
Redefining Retirement in the Modern Age
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In this conversation, we speak with Aaron Smith and Will Simpson about the evolving landscape of midlife, retirement, and entrepreneurship. They explore how individuals in midlife can redefine retirement, the rise of solopreneurship, and the importance of multiple income streams.
The discussion emphasizes the need for a strong understanding of personal finance, market dynamics, and the significance of validating business ideas. The speakers share their experiences transitioning to fractional roles and the challenges faced by those in corporate environments.
They also highlight the importance of understanding one's motivations and the changing realities of work in today's economy.
Welcome to Midlife Kicker, the podcast for professionals who've left the corporate world but aren't ready to slow down. We deliver stories from midlife adventurers who are breaking boundaries, reinventing themselves, and building new careers and businesses on their own terms. Each episode delivers fresh ideas and practical advice to help you launch your own second act with confidence. Your midlife moment isn't an ending. It's your springboard to something even better. So if you're ready to kick open new doors and create your next chapter you're in the right place. Let's get started.
SPEAKER_02:All right. Well, today I'm joined by two men with exceptional business experience and some interesting ideas on midlife and retirement. Aaron Smith. Aaron has performed many roles, mentor, investor, entrepreneur, host of his own podcast. And Aaron and I met at Dell several years ago. And since then, he's been busy with multiple software ventures. And Will Simpson. Will's a fractional, excuse me, COO and executive coach. Will worked with Aaron at Hoover's, the D&B company, and recently gave him some insights into early staging investment and company structures and these two friends have now partnered on several projects and are beginning to ask what happens when people reach a point when they're too young for retirement yet considered a little too seasoned for corporate roles and as a follow-on could midlife be the best time to become a software founder so gents happy to have you here maybe we begin with this question on retirement like how do you define it and then maybe we move on into hearing about your past to the present day
SPEAKER_04:well you want to go or you want me to go Yeah, you know, I'm an opinionated guy on this one. First of all, I'm joining you from Panama City. So that's Ciudad de Panama. And, you know, it's wonderful. It's different, but it allowed me to do some of the things that I wanted to do. You know, When you tell your friends and family that you're about to retire, there's a whole lot of questions that they start hitting you with. Some things you've thought about, some things you haven't. One of them is, obviously, how are you going to pay for that? And I definitely have opinions on that. But the other thing is, what are you going to do? And I know a whole lot of guys who are still working, not because they have to, but because they can't think of what else they would do with the time. I think retirement is what you make it. It's an adventure that's unlike working world if you are like me you choose to get up and do something productive it also affords you the opportunity to focus on the things that are important to you so if you want to devote more time to charities if you want to get up and go golf if you want to go do whatever it is you carve out that time but what you should find out is you still don't have but 24 hours in the day so yeah that dance card gets filled up pretty quickly that's that's kind of what i see the other thing is you know for me personally i've chosen to definitely took about three to four months just to kind of decompress. So before I left the States, I set up a fractional product marketing business, very similar to what Will did. I had a great mentor. I'm not going to say her last name, but her first name is Susie. So if she's watching this, shout out to Susie, who advised me on what I should consider doing as I started making that transition from full-time employee to life outside of the corporate world. And one of the things she said was, hey, approach your current boss, especially if you're killing it. Approach your current boss and give them the proposition of moving you to a fractional role. It's going to save them money, and you can work out a contract from there. I thought she was nuts. I was like, there's no way I'm going to approach my boss, who at the time was the CEO of the company, and say... You know, I'm looking at pivoting and this is my timeline. But what worked for my benefit was I was pretty transparent from the time I joined the company that this was like my last stop. And, you know, it's not like my parents when they retired and there was an announcement in the office and they had cake and they got, you know, cards or whatever. Like, effectively, retirement for Gen Zers, you know, I'm sorry, Gen Xers is what I want to talk about. Retirement for Gen Xers is really... Employment termination. That's how it's treated from an HR perspective. So what we did was we terminated my employment, restarted as a contract. And I did that while we moved our home to a new country. So I did that for about a year and then started poking my head up as Will and friends started bringing new opportunities my way and making a decision on what seems interesting. Because it's a whole lot easier to... to pay for your retirement years with cashflow than to watch your savings, no matter what your savings amount. Like this is not an indictment on did you save enough, but no matter what that number is, when you start seeing the amount go downhill, you start to think, man, you know, even if I was able to bring in a small amount, it would offset that. And so that's the way I start to talk to people who are in my position or saying, hey, I'm thinking about retirement. What would you advise? And I'm like, you know, Number one, be aware that that number starts to get nervous. It's going to make you pucker. But at the same time, we are in an age now where it's easier to work remotely and it's easier to carve out a business that you'll enjoy doing that gives you just enough to live on. That's my feeling. I know that was a little long-winded, but feel free to ask me anything. Will, I know you got an opinion too because you've been at this longer than I have.
SPEAKER_02:Yeah, let's hear from you, Will.
SPEAKER_01:Yeah, so for me, I never ever planned on retiring, I still don't. I don't know what that word means. However, I left corporate America in 2018. My wife actually left in 2015 and she's a fractional as well. And so, you know, I kind of use the learnings of her going fractional to help me. And I did that for a while and it was fun, you know, and I went and did some, you know, some big fun things, right? You know, setting up, helping bigger companies set up companies overseas or smaller companies just being their fractional COO. So, you know, that was fun. And then in the last three years, I inadvertently entered into what other people were calling retirement. It wasn't what I was calling retirement. It was what they were calling retirement. You know, I took some time. I wrote a fiction novel. I took some time and I worked for some nonprofits where I didn't get paid. And I did some pro bono things and some things like that. And then what I realized when it was like, okay, well, let me lean back into picking up some paying clients. The response was, oh, I thought you retired. And I was like, what is that retire word again? And so for me, it's like, I don't, I'm going to pile on to what Aaron said. I'm always going to wake up and do something and be productive. I don't, I mean, my golf game is never going to get any better. I'm terrible. I go golfing every once in a while, right? But it's not something I want to, do most of the time. I need to build or do something. Through working with Aaron and talking to some other mentors and people that I worked with for a long time, what I realized is that leaning back into entrepreneurship is really what is going to bring me and has been bringing me the most joy. And I've just recently started to find out this, that if I look back, I've always had that gene. And so now I'm just stretching it and building it. And so for me, that's what retirement is. It's stretching it and learning to build a muscle mass around my entrepreneurship gene. And, you know, still doing fractional work. I'm still doing all the things. But like Aaron also said, working remote and multiple streams of income is the new way, especially for us in mid-journey. You know, I'll be 60 this year, so I'm not over the hill yet. But, you know, this is something that I think that I can do. So that's where I'm at. That's actually
SPEAKER_04:the key thing. I want to go back to something Will talked about, like multiple streams and living remotely. Like right now, you see a lot of offices telling their employees that they had told just three or four years ago that they could live wherever they want to and be productive at work. And we know the productivity hasn't gone down, but they're now being told they have to come back to the office. So if you're in a position, and I always start off by saying this, if you're in a position where you are already killing it on the job, right? Listen, nobody's indispensable. But you always want to come from a position of knowing what your worth is at that point in time. If you can leverage that and say, you know what, I'm willing to give up something to get something. And for a lot of people that giving up something is, I can give up the FTU world. The kids are already on their way. You know, real estate being what real estate is, you never know. Depends on what market you're in, but maybe you can sell. And that becomes a nest egg. And you can live remotely. And oftentimes, if you don't focus in on one specific place, but if you look at the geography of all your options, right? You take into consideration proximity to family or working hours or who your clients want to be. I'm sorry, who you want your clients to be. All of a sudden, the playing field becomes larger and the expenses to live that life start going south so now you're like instead of instead of needing you know 250 000 a year to live on now you're talking about why i can still look like a king on 60. the math starts working in your favors you know i think especially when you're talking about knowledge workers that we all were you know all are. We are adept at looking and surveying strategy and making calculated bets on what makes the most sense. Why wouldn't you apply that to where you live? Why wouldn't you apply that to how many enterprises that you choose to work
SPEAKER_02:with? You guys have mentioned ways that you got into these fractional roles, but for those that maybe are looking for a way to engage with others that are maybe in the same boat, they're considering this thing, you Any recommendations on that?
SPEAKER_04:Sure. Will's more of a coach, so I'm going to let him fire first on this one.
SPEAKER_01:And, you know, and I'll make a quick clarification. You know, people say, coach, I'm more of an advisor than coach, right? So I'm not your therapist, right? So I'm not the kind of therapist. I'm not your business therapist, right? That's not me. But on advisory, I met with a group of women and technology people just a week ago. We talked about this very thing, right? This very, very thing. And it's like, these people are like, hey, we're ready to make this move. How do I do it? Right? And that's a question that we can dive in. I've got an hour presentation I do. I talk about it. There's some basic blocking and tackling that everybody should think about, right? And we've already hit on some of them. And if you think about, hey, all businesses are three things. They're finance, they're operations, and they're sales. All businesses are that way. Operations in the, hey, I'm going to do it myself. That's you. You have to have that in spades. I'm not going to advise you how to do your craft. We're going to assume that you are your craft and you're good at it. Finances, don't go crazy spending money coming out of the gate. You don't need the best website in the world. You don't You don't need to buy and spend all those things. I recently got my real estate license. Think like a realtor. They don't spend no money. And that's the way to do it. It really is. And then think about the other thing that Aaron said on the finance side. Think about your runway. That's what you do in your first year to 18 months. Consider that your job is to extend your runway and nothing else. It's not to hit those big numbers. It's to extend your runway. And then think about your sales. You've got to have a plan and you've got to have something written down. You can't just, well, I know a lot of people. Build it and they will come has never been a thing. It's not going to be a thing today. And if you're the it, you can't just wave your arms and have people come and sign up. Well, I'd love to pay you 250 bucks an hour to do this thing. But do like Aaron said, leverage your relationships. You have to get started in that runway while you're building a plan. That's what you want to do. Start small. So the end of that conversation is start small.
SPEAKER_02:Yeah, fantastic. I couldn't agree with that more. So let's maybe we move into what are you guys working on now? What do you want moving into next.
SPEAKER_04:So I'm going to start off on this one. So we are working on something that really, I think, lends itself to the question that we ended with, which was, how do I get started? So Will and I have been working on a couple of enterprises for the last, I don't know, six or seven months. But what we've seen is an acute need and a very specific need area and it really comes down to people who they have it in them that they want to go and do something on their own whether they whether they have it innately genetically like we'll talk about or whether it's been thrust upon them listen the white collar market has been a recession for a couple of years now if you've been laid off chances are you know that it's it's been a longer period without a job than you ever thought. I've had people who've been laid off and they thought it was going to be three, four, five, six months, and they're going on a year to year and a half. So a lot of times, starting to think like an entrepreneur is coming because it was just thrown in action. But then we've had this marvelous thing called AI thrown at us too. You know, I shared a couple of articles late last night with both of you, but in summary, it went something like this. You've got some big companies who are hedging their hiring going into 2025, 2026. I'm not going to mention any specific names, but you can Google it, find out. And they're saying, yeah, we're not going to hire the HR headcount. We're not going to hire the engineering headcount because we think AI is going to be able to solve for that. Then you've got other companies who are saying that they already went all in on AI and Now they're bringing the humans back because they're seeing the limitations of AI. So what does that mean? That means it's all over the place, but you do need to start taking some bets right now. And if you're someone who is kind of playing around with AI and saying, you know what, there might be something here, then you probably are going to be interested in what we're putting together. And so it's not named yet, but here's some things to start to consider. If you're someone who says, you know what, I want to do consulting or fractional at some point. Well, the easiest thing to do is to talk to your immediate network, your immediate contacts, and see, you know, do some market research and see if there's any demand, right? And for me, at the time that we did it, it was 2023. You know, a lot of people had just taken part in the Great Recession. They had gotten new high-paying jobs, and a lot of companies were like, I don't have a lot of money to spend, but I need help. So being a fractional kind of off the books made sense. I don't know where we're at right now. But what I do know is whether you want to be a fractional, whether you want to, whether you've got an idea for a cool software thing, there's a discipline around it that a lot of people don't know what it is. And so a little bit more about our background, you know, Will and I have a combined 40 plus years in technology. He was my technology partner. at the New Branch. But I didn't tell you what I did there. So I was a product manager. And a product manager is not a known field outside of technology companies. So assuming that you're someone who's coming from a dental or healthcare practice, you may not have ever known what a product manager does. In brief, we would write the business plan for any new product, maybe 60 pages or so. half of which never got read. I tell people, writing the business plan isn't so you can show somebody your business plan. It's for you. It's for the author to think through all the things that you need to consider. Same thing happens when you are building your enterprise of being. When you're doing that, You have to have a business plan. And it's not so that you can go to the bank and ask for financing. I need$100,000 so I have a runway to get my first client. No, that's not the point. The point is, so you know, is there actually demand for the skill sets that you bring? And if there's not, can you augment your skill sets so that you are in demand? Or do you pivot into something that is more aligned to what your interests are? A quick couple of statistics, right? So when I got started working with Will at the beginning of... Well, actually... towards the mid-20s. If you were interested in a software startup, you had to have a certain background. You were a technology person. You were a coder. So between the two of us, we'll have more likelihood of getting funded. Well, for a whole lot of reasons, but we'll go into those later. The other thing is, you were likely to get between$500,000 and a million dollars of seed money to get that idea off the ground. By 2014, that went up to about... 2 million, 2 million to 3 million. Why? There was more excitement, more VCs competing, looking for more of those unicorns. All right, now as we enter in 2024, 2025, it's still where they're looking for someone with a business background or a strong technology background. But now the market has started to pivot to say, there's something happening with the individual, the solopreneur, who has an idea to bring to market And the investment amount isn't what it took in the past. The investment amount for seed round could be anywhere from$50,000 up to 500. Are they looking for unicorns? Probably not. So if you're the person who has an idea that you want to bring to market, you need some business discipline. You need to prove that there's actually a market there. But you also don't have to look for something that's going to require$3 million of funding just to get built. that those days are fast going behind us. Are there still always going to be need for big platforms? I'm not necessarily sold on that, but I do know that for people who were previously shut out of that space, the world is a whole lot more federated now. It's democratized. If you have the idea and you're willing to get the guidance on proving there's a market and be willing to build a working prototype that may not be what your entire vision is, but has parts of it, you could probably get funding today. And maybe it only makes you$100,000 a year. Could you retire on$100,000 ARR? Probably. And you probably do so in a lot of different geos. So that's my opening salvo. We'll take it over. I'm
SPEAKER_01:going to jump in on some of that, and I'm going to roll the clock back a little further than Aaron did, because I've seen part of this movie before. In the mid to late 90s, You know, there was this new disruptive technology called the World Wide Web that no one had ever heard of, right? It was becoming, you know, an enterprise-level thing. And the answer was similar to what we just said here. Look, individuals can now have their own marketplace, right? That was what everybody was talking about, right? We can have your own store, brick and mortar. Remember those terms that were out there? We're going to compete with the brick and mortars. And there was a lot of things. And what happened was that a lot of the individuals who were tech professionals savvy people came out there and stupid money was being thrown at them. And I call it stupid money because there was no business money. It was just the technology. It was just this one piece. And just like I talked about in the very beginning, all businesses have three things. If you only get operations and no finance and no sales, you do not have a business, right? It was the same true then. It was there now. We all know what happened. You know, let's just fast forward a little bit. We have been a bit of hindsight. 2000, 2001 came along, dot com, boom. We all, we remember it. You either lived it or you know about it. happened because we had so many businesses built on houses of cards that hadn't done their due diligence, hadn't really gone out there to make sure that they were coming up with something that wasn't a science project, but actually was going to be viable in the marketplace. And so we're trying to take those lessons, part of what Aaron and I are bringing with our experience, including that is, hey, we want to help you win, right? We want to help you not make some of those same mistakes that we, in fact, have lived through before. We're not guessing. We didn't read a book about them. We felt the pain, you know, So all of those things combined is like, hey, you know what? This is a cool new technology. We're not taking anything away, but let's take advantage of it the correct way with also, also, and also. It's not, cool, I can build an app with AI in six hours. There it is. How come nobody's buying it? Where's all my money? I was counting on this. I could be$200,000 a year. And it's because you built an app that nobody knows about it. Nobody, even if they do, then they're like, I don't need this. I can do this myself for free. So all of those things have to be vetted. And that's what we're going to bring as part of our solution, name solution, as it were. And the other thing that we're going to put out there, and I hope I'm not dropping it out of the bag too soon, but we're entering into it purposely on the global market. you're focused in saying, look, this is a global company from day one. So we're not saying, oh, we're only going to go here, we're only going to go there. We're not geographically limiting this. This is a global endeavor for all peoples that want to show up and be in the solopreneur world and move it forward, right? It's disruption at its finest.
SPEAKER_04:Let's clarify a couple of things. So solopreneur has a lot of different meanings, right? So a solopreneur can just be one guy who's doing consulting work. And we're not saying that that they don't have value in what we're talking about. But really, the focus is on people who have an idea that they want to build into a software business, and they want to do so in a smart way. They don't know about, you know, how to start up, how do you get funding for your first startup? But I can guarantee you, it costs more money than you think it does, but it doesn't cost as much money as it used to. So somewhere in between those two extremes.
SPEAKER_01:How do you- Yeah,
SPEAKER_04:solopreneur are not
SPEAKER_01:services, right? So not human-delivered services is, you know, is what we're doing. And there's nothing wrong with you. I mean, hello, I made a living off of Soul Opener Human Services. I'm not discounting it at all. But that's just not necessarily our target market.
SPEAKER_04:For a lot of people, that's going to be the first thing that they step into. And to be honest with you, it's a great opening place. And for very many people, they'll probably go into that and stay there. But at the same time, there's an opportunity, and we see it happening. You see people saying, oh, I built this cool new thing using AI. eye prompts, you know, it does X, Y, Z. And you're like, okay, that's great. Where's the revenue? How are you marketing it? What do you think about in terms of partnership? Who is this thing actually compete with? Are there other competitors out there that do the same thing? You never know. Well, Roy, we're going to turn it back over to you.
SPEAKER_02:Yeah, well, you know, you hit on a number of things there. And you think about, like, the market. What's the size of the market? The competitors, right? Is there anybody else out there doing the same thing? And a lot of times there are, and that's okay in many cases. Not all, but, you know, but there are... That means
SPEAKER_04:you have a market.
SPEAKER_02:At least you know, yeah, right? And so how many CRMs are out there. I mean, there's a jillion, right? And then there's more every day, it seems like. And then with regard to services, you know, sometimes I think that people who may start there end up realizing that there's a consistent problem that they see. And that problem could evolve into an application that essentially solves the problem.
SPEAKER_04:I've got a guy here, to be honest with you. I've got a guy here, young guy, one of my youngest prospects, we'll call him. His challenge isn't creating business. He's a services guy. He's a digital marketer. And he's decided that right now he wants to start disrupting himself because he knows that he can't man all the different pieces of his solution by himself. So he's coming to us saying, How can we automate this? Can you build me a system that automates what I do and very smartly going after one specific vertical? So sometimes saying no to a whole lot of things but saying yes to one thing will be your saving grace here.
SPEAKER_01:The other thing, Bert, these service solopreneurs that are going in and some of the solopreneur communities that I'm a member of, we talk about this, is that The revenue looks like this. All the services people, we love it when we're working, so we quit networking and doing all the things that you need to do to get clients,
SPEAKER_03:right?
SPEAKER_01:And then you lose a client. And so what we're saying is, hey, but you know what? I guarantee you, you felt the pain, just like you said, Roy. You come up with a need. And what if you could augment? Okay, let's just say you're not looking to build a unicorn, but if you were looking at something that even brought in half of what Aaron said, let's just say it only brings in$50,000 a year. So now you're It doesn't look like this, it looks like this, right? You're much less. And you just got this, you start to extend that runway, start to build that little base. And this way you're still doing the services that you may love and you're being a fractional COO and you know I love it, but I've got this other revenue stream from the software business that I started that made sense and had customers and had need in the marketplace. And now I can count on that baseline revenue so that I'm not so feast and famine. So there's lots of ways to look at this and make that, you know, when you combine the place that we, you know, we kind of said this already in the start, those of us entering this midlife, retirement, whatever you want to do phase, we're not billionaires, right? We don't have unlimited funds, so we do have to watch, you know, income and outgo. We don't like the feast and famine of only doing services, so we lean into the multi-streams of income, and it can be, it might be multiple services, but it can also be things that aren't services, and that's where we're playing. Like, look, we can help you. We can help.
SPEAKER_02:Yeah, no, I like it. You know, one of the other things is that for some of the, I'll say service providers, right? AI can certainly augment some of what they do. Not all of them, right? If you're out there, you know, cleaning a pool, well, but it may be it helps you with your funnel, right? Your sales funnel, right? Lead generation, things of that nature, right? So there's a lot of places where it can play to help smooth out that curve, right? Because we all need that funnel loaded, you know? Oh, that's excellent. Well, you know, you started to bring up the midlife thing. And so maybe we talk a little bit about that because, you know, You know, there's recent, I mean, just reading about, you know, Microsoft the other day, right? Laying off 7,000 people. And, you know, a lot of them were in the, really in the software engineering area, right? You know, the devs and program managers, a lot of what I've done over the years, and some product managers, things of that nature. And that's just one company, right? A big company. But many of these people had, you know, 20 years there, 25 years. And so now they're at that point where it's like, just like what we talked about at the very beginning of this, right? They reached a point where they're too young to, stop and maybe they're not able to. Corporate is not that crazy about keeping them around. So maybe we get into the midlife topic and how people are embracing some of these ideas and maybe some of the things that are impacting them and causing these changes that we see in corporate America.
SPEAKER_04:So I want to jump on this one first, right? Because the thing about... losing your job from a company like microsoft if you've been there for 20 years chances are you're still leaving with a relatively robust stock portfolio made up of microsoft who are doing wonderful right so my heart still goes out because you never know what somebody's personal finances but When you think about people who aren't in that, if they don't work for a Meta or an Alphabet or Microsoft and they're still getting impacted, you know, the average 401k balance is about$192,000 for somebody who's in their, you know, born between 1965 and 1980. So I always refer to the Gen Xers. I don't typically talk about boomers because by and large, they have something that a lot of Gen Xers missed out, and that's the pension. We can make an argument that everybody who's a boomer has a pension. I get that. But when we're talking about just overall markets, that's the last group that benefited from having a combined pension along with a 401k program of some sort, right? So they were set up differently. I remember growing up and everyone telling me from the time I was an undergrad, you just got to make sure you put some money in your 401k. It's going to be great. Well,$192,000 does not add up to a great retirement. So my thesis is really, you know, if you go right now to bizbuysale.com, there are any number of small businesses that are for sale by the previous generation. Matter of fact, they're trying to unload their businesses so they can retire. And that's great. And if that's something that interests you, you're probably not our target market anyway. But, and I would even say that even if you own a small business, you probably have an idea for something that you wish that you created or something that would just make life easier for not just you, but for people who do the same work as you. If you're not in that group, if you work in tech, but not one of the majors, you don't have a huge stock portfolio that's going to carry you for the next 10 to 15 or 20 years. What do you do? What we do know, and I don't care what your beliefs are politically, your social security check is either going to do one of two things. It's either going to give you just enough to live on, or it's not going to be there at all. Those are the two options. You can argue about how much more it could be, but right now, it's not set up to give you a standard of living that most people are going to be comfortable with. What are you going to do? You have to come up with a plan. And when I see the various companies right now, the early movers, the first movers who are promoting, hey, you be your own software startup and you can make a gazillion dollars. In some ways, they're being disingenuous, right? If you actually look at the case studies of the people who are being successful, they're people who already have started a business or two, or they were already coders for small companies and they were selling to people who code just like them. So they knew the market very well. What about the next group? So I'm surprised that it's not as urgent as an issue for a great majority of people. One of the things that Will had mentioned early on, we said we're going to start an international company day one. Without disclosing where we're setting up, there are grants being made available to companies who are willing to help individuals to become self-sufficient and become startup founders. They're not necessarily self-sufficient. They're not always in the U.S. They're in other geos. So it's part of what we do, which is really a combination of advising and software development. It's that intersection. So we can take a person who has an idea and help them refine it before they go spending money. And then once we validate it, that there's a there there, then we hand it over to really low cost software development. so they can get to the next phase. And we know in software development, there's always a next phase, whether it's the next round of funding or what have you. But it's nicer to know that you can work with someone who's going to do this on your behalf without asking for a percentage of your company, which is what a lot of outfits who offer advising as a VC do. would do, they're gonna do it for a percentage. We are saying, we'll do it with you for a fixed amount that's transparent. So, you know, there's always gonna be opportunities to partner, but there's always gonna be opportunities to say, you know what, we're here to help you. We're your virtual CTO and virtual advisor.
SPEAKER_01:And, you know, going back a little bit on the midlife is that, you know, I'm gonna pile on to what Aaron said about, you know, I'll just put in your 401k. I've never been a performance. I guess that's a fair word. You know, I didn't finish college. I don't have a degree, right? I didn't. And I came up through technology and made it all the way to the C-suite without it. And generation, that's very unlikely, right? I mean, if you tell people that today, they're like, what? How do you not have a degree? You were the COO at blah, blah, blah, blah company, right? And so, you know, things have changed. And And looking at that and not going, well, I need to put a little bit in the 401k, I need to make sure that I pay an extra$100 a month on my mortgage and keep that car an extra two or three years and all of the sage advice that I'm not discounting, but it also isn't going to get you to pass that average 192 that we're talking about, which I'm just going to tell you, that is not going to get you anywhere. It's like, especially if you're trying to stay and live in the States. But even if you're not and you really cut it down, what are you going to do in retirement? You know, the other thing is, is that the retirement age to the time we're not wandering around on the earth is also longer. So what are you going to do? You're going to sit in a chair and do nothing? If that's your goal, hey, good for you. I'm glad that you can be happy doing that. And so my advice, my thing is, is that we talk about mid-journey. Yeah, let's... The 30-somethings need to be thinking about this too. We need to get deeper in there. This is not just for the, you know, 50 and 60-year-old people that we're talking about. We're talking about the 30-somethings. Think about it now. Even if you look at the way that we've engaged with companies throughout careers, there was a day when, you know, a decent tenure was, you know, 15 years or so, right? And if you're in technology space and you stay with a company more than four or five years ago, man, what are you doing? Why are you still there? So their notion of stability has changed. And so again, back to thinking in multiple streams, thinking about disrupting yourself and thinking about what is, what am I going to do? It's like, okay, I still got kids at home. I'm not ready to retire. I'm not ready, but what am I going to do? Okay. It's not a viable thing. I know social security is rickety bet at best, right? I've got to put into it and that's all good. And I understand, but I can't really count on that. And even if I put those two together, I can't start Start thinking now about something other than. As you're entering midlife, talk to some people that have been there, done that. And make some differences now.
SPEAKER_02:You know, some of your experience, I mean, experience I've had, my experience has been is that these things, for me anyway, have always taken longer than I thought they would. I can get development done like that. I can go and create something quickly. And it, you know, it works and all that. But there's a lot more to it, you know, to your point than that, right? Is it a real thing, right? Is it something that people want? Again, to your point, you can't just build it and they will come because they won't. You got to go make some noise. And the thing is, a lot of the, I'll say that there's a, there's a A set of folks, an age group, tend to be at the younger end. They're used to seeing people with, you know, in these YouTube videos, right, on private planes and Porsches and all this kind of stuff like that, you know, Lamborghinis. And it's not always real, right? There's a lot of fakery to that. But, you know, they want to move fast. And I don't blame them. I like the energy. I've never been that patient myself, and I like that. But there are some of these things that it certainly behooves you to take a little time and have a little thought, you know, and maybe get some thought leadership. Right. And, you know, be better prepared as you go into these things, because it doesn't always turn out the way that you think it might. And, you know, there's been a lot of pivots that have happened. Right. Pretty, pretty incredible ones just recently. I mean, like, you know, just the other day, Windsurf, right? OpenAI, you know, wants, you know, three billion for Windsurf. They pivoted. Windsurf pivoted a year or so ago. And so anyway, there's a lot of that. And so, again, I'm thinking, you know, where you understand what... what the idea is, what the market is, and get some input from others. Again, things that I think are a great idea, I go talk just to my wife, and she was like, yeah, what are you thinking? Are you nuts?
SPEAKER_04:So here's the thing. So in terms of technology and ideas, most people that I come across... they're going to be in one of two camps. Either they know that they just are not that creative and they can't come up with a lot of ideas, or they're the kind of person who can throw off three ideas between the time they get up in the morning and the time they go to bed. Their issue is, how do I qualify which one is worth my time to pursue? And so having somebody who's a sounding board can definitely help to filter all that. The thing is, no matter what the idea is, right? Someone came to me the other day with an idea about a music player that could be, you could crowdsource the playlist and it would automatically sequence it based on not just the BPMs, but the vibe. So I'm also a part-time DJ. We'll say a bedroom DJ. That's what they refer to us as. And so you could feed that into a software and it will auto mix to create a party. And that was interesting. But by the end of the day, she had another idea, right? And so, but here's the thing, right? The thing is, is while the technology and the ideas may change, the discipline required to validate the idea stays consistent, right? And it doesn't have to take a long time. It can. And it also doesn't have to take a lot of money. It can. And I'm always in favor of providing a person, and I did this as a product manager, you know, I would give basically three scenarios and three levels of investment to make a decision on what to do to get to the next gate, right? Those are things that we are trained to do. Roy, you've done this throughout your career. So we have the benefit of knowing how to think of getting something from an idea to product that is not necessarily known to a lot of people unless they go through basically learning school of hard knocks. They try a couple of ideas, they fail and they figure it out. Oh, I need to do more research in the front end. But I think... that having one or two people near you in terms of being able to flesh out ideas, in some ways it's a benefit, but it's also a problem. Because remember, when you come up with an idea, you also have a target market, and the people around you may not be the target market. Exactly. Right? And so the conversation that I have with my friends and family when I have an idea is they'll say, well, that doesn't make any sense to me. And I'm thinking to myself, that's because you're not the target market. But if you were, because we talked to so many people. So I posted this on LinkedIn a while back, and I think you may have seen it, that right now, if I were investing in a software startup or a startup of anything, I would focus the majority of my energy on how to get to know the market better. and get their participation even more than building the product itself. 100%. If you can get them to have a conversation and engage with you, your target market, then building the product is actually much easier.
SPEAKER_02:For sure. Yeah, I'm actually going through some of that right now. I mean, I'm going to have webinars with people that are in the commercial construction business, right? Schools, hospitals, hotels, you name it, right? And I know a little bit about that field, but not as much as they do. And so I'm essentially looking to pick their brains, right? And how AI might be able to help them, right? How they can use that in some of what they do. But the key is understanding, you know, essentially their day-to-day and what's, you You know, all those questions and pseudo cliches, you know, that we've heard for years and years and years. But basically, understanding that market a little better, a little deeper. And, you know, frankly, one of the things I ask people all the time is like, hey, what's a task that you have to do day in, day out, week in, week out that you would love to hand off to somebody else? And when I hear that, I always write that down because that's an idea that, you know, that's a problem, right? Potentially, right? Again, you got to go and dig in a little farther. But
SPEAKER_04:anyway. The beauty of being... someone who's midlife is, especially if you're somebody who's been in construction for 15, 20 years, or you're somebody who been in healthcare 15, 20, or something that you have. So the way I view AI now, and my wife and I was having this conversation last night. Right now, a lot of ways that ChatGPT and tools like that are being used is like the ultimate virtual assistant that you can ask it a bunch of questions and it streamlines the work that you would have done. That's tip of the iceberg still.
SPEAKER_02:Right? Right.
SPEAKER_04:Now you can do agents to go out and do tasks. So the things that you were talking about in terms of doing the market research or standing up the landing page or all. So, you know, you can deploy agents to go do that. Nothing beats being able to have a real conversation with real humans until you start selling to the machines, right? So as long as you're still transacting and expecting money from a real human, nothing is ever going to replace having that interaction to find out if they're there. But to bring this back to home with someone who's, you know, 40, 30, 40, 50 years old, you already are a subject matter expert
SPEAKER_02:in
SPEAKER_04:something. So you don't, when I see people saying, you know, and I'll be guilty of this too, but when I see people saying, I'm out of work, I'm going to go pay to go get my resume updated, my LinkedIn profile updated, I'm going to go back to school, get this certification, blah, blah, blah. What my brain starts going to is, okay, so now you're competing with on many different variables, right? You already are a subject matter expert. What we need to do is pull out the problems that you already know about that need to be solved. And would you rather, and this is hypothetical obviously, would you rather spend$10,000 getting a new certification and your resume and your LinkedIn profile? Or would you rather put that money towards building a business for you that could throw off$50,000 to$60,000 a year? It should be a no-brainer, but it's a mindset change that most people aren't... They're not convinced that they can trust themselves to make that commitment. And that's a lot of what we have to...
SPEAKER_01:That's it. Most humans don't like change. As I was saying in the tech world, you want to keep an engineer in their seat longer to throw nickels, dimes, and quarters behind them because they're afraid of change. They won't back up. And so with that notion that people are afraid of change is that they see it. from their perspective as a risk, as something crazy, as something scary. And so they'll double down on their commodity. It's literally the same commodity that got them pushed out of the marketplace to start with. The reason that you're 55 years and can't get another job is because ageism is real. And doubling down on a new cert and getting the best resume on the planet and the best LinkedIn profile on the planet are going to do you zero good. I've spent those thousands that Aaron talks about. I'm not guessing, right? And so... The thing that I want people that are listening to this to take care of You don't have to wait until you're 50 or 60, because even at 30, you've already got something. Got us. You're an SME. You're a subject matter expert on something. Do you like that something? That's the first question you should ask. And if not, great. Then become, you've got a little time, become a service matter expert between now and the time, so that when you're ready to pull that trigger, you can go, okay, this is where my next happy place can come here without depending on... This very fickle and not on your side corporate machine. But America is not there for you. This is not the way it works. It's not reality. And so helping people to see a new reality. I mean, look, in a lot of ways, you know, I say we're not therapists. You know, in a lot of ways, that's not necessarily true in some ways.
SPEAKER_02:Well, you know, and I was just thinking as you were saying that, somebody would have said that to me when I was 30 or 35, you know, and really kind of pushed me on that. But, yeah, no doubt now, you know, there's so many of these folks that aren't in tech, right? I think one of the issues I have is a bit of a bias because I've been in tech all my adult life. And so I tend to think that way. But there's so many people that are not, right? Again, healthcare and not necessarily the tech side of healthcare because there's a little bit of that. But they could be in virtually any field and when this happens to them, it's a shock to the system, obviously. And then it's like, well, what do I do? And they do fall into these kind of, I don't want to say trap, but these common steps of updating the resume and such. And I think that Entrepreneurship really has to be the answer. I don't see too many other options. And so if that's the case, let's just assume that that's a valid thesis here. So if they're going to go off and do this, they need to understand the market and competition and such. But how do they really start? Because I see people that say, I'm going to go out to Upwork or whatever and post something out there. And they don't necessarily know what they're going to get. They don't necessarily know the questions to ask, right? So I'm
SPEAKER_04:going to serve this one up to Will. But here's the thing, Mike. Look, I was there. And what we know is that the employer-employee relationship is changing once again. It changes in every age. And we're upon that change again where... And I actually think the younger people, like my sons who are in their 20s, already have a notion that they don't expect any particular job to be meaningful. Other than providing them a paycheck to live on, that's the full extent of the agreement. Whereas if I talk to my mother, who was a state worker for most of her career, like she expected to be taken care of. That was part of the contract. So what we're really saying is how do we start to rewire ourselves so that we're prepared to be self-sufficient And I think that doing things like side hustles or, you know, Upwork or whatever, it is a good opportunity just to get your toes in the water. But realize what it is. Just because you're doing that in year one, know what you're doing it for. Maybe it's for some extra cash, but maybe what it's really doing is teaching you how to budget, how to think about yourself as a business owner, even if it's a small business at the time. One of the things... that Will kind of touched on. We talked about the three things that every business has. Here's what I know. I know that a lot of people are okay with a lot of the idea of being a business owner. And even if, you know, especially if they're married, because they can say, well, I'm not that great with money. My wife is, so she can have the accounting. I'll handle this other stuff. But universally, there's one area that everyone seems to want to fall down on, and that's sales. Nobody things that they're a seller.
SPEAKER_02:Right.
SPEAKER_04:The good thing about technology today is it can do most of that. You know, there's online platforms that you never actually have to sell, right? But you still have to think about the customer and how you position things to them so they will buy. The funny thing for me is most people who approach me and say that they're not a seller are some of the biggest salespeople I've ever come across because they have sold themselves on the notion that they can't sell. My wife... has an affinity for working out. So if she had ever gotten a chance to work for this particular vendor who took off during the COVID era, who does exercise equipment remotely, if she had ever gotten hired, she probably would have been their top salesperson. This from the same person who says that they hate selling, they can't sell. So what I tell people is it's not that you can't sell, it's that you don't, you haven't found a thing that you're passionate about yet. And so as Will was talking about, you know, finding things, trying things that, you know, if you're 30, if you find something and you're not really excited about it, go on to the next thing. That's really what we're talking about is finding something that you can be passionate about. There used to be a TV show. It might still be on. Like I said, I'm in another country, so I don't get the same channels. But it was called Dirty Jobs. And I used to tell people all the time, there's a lot of money to be made doing dirty jobs. A dirty job is a job that nobody else wants to do. We all look at it and we all say, I ain't doing that. But even garbage men... in New York City can make$100,000 plus a year. So it may not be a lot of money, but it's all in changing the way you think about the problem. So, Will, I know I was long-winded. I know you talked to a lot of people who are at that point or you have spoken to a lot of people who are at that point that they don't know if they're ready to be a business person. What do you say to them?
SPEAKER_01:And so what I say is, one, understand your why. Why are you going off on your solopreneur journey? Whether it's solopreneur in services like we talked about or whether it's solopreneur to start a business of some sort or both, right? Understand your why because it needs to be strong enough to help you to do the parts of your business, at least initially, that you do not want to do. You want to do the operations part, because if you don't want to do that, well, don't even start, because that's you. So you want to do the operations part. You have to do the financial part, and everybody seems to understand that you have to do the financial part. There are some good resources, and you can tap your network and get the very minimal part done, form an LLC, all of those basic blocking and tackling things, and those tend to be one-off endeavors. So that also tends to get done. It tends to get overdone, actually, but that's okay. When people fall down, It's for people, especially people that didn't come up through sales, didn't come up through marketing, didn't come up through product promotion, right? Or Marcom, as it was called in the day. If you didn't or not experience in that area, people look at it and say, well, you know, I'll just make some posts on LinkedIn or I'll just have a, you know. And so what I'll say is your why needs to be strong enough to get you across the line to the basics of marketing you. or your product. Do you know your niche? Oh, no, there's no such thing. Yes, there is. You're just not, you don't, you need to talk to somebody or something that can ask the right questions. What is your brand authority? Right? That is... Why does your niche, why are you an expert, right? What is your SME, right? What is your there? It's like, I don't know. It's like, okay, well, again, talk to somebody or something and get that done. And then you take it the next, after that, it's like, okay, well, I got a brand authority. It's like, okay, that's cool. What's my proprietary or unique method to me, right, to what I'm doing or my company? What's special? One method that makes this different from all of the other fractional COOs out there or whatever it is you're doing or from software that, develops colors, or whatever it is that you've got. What is special? And then finally, we get to the crux of it, because we don't get all four of the primaries. The fourth thing is, what is your lead generation system? System, plan, not, well, I'm going to post it on LinkedIn twice a day. That's not enough, right? It's like you need to have a system, and you need to figure out a way to work and go with that system progressively over time, balanced against your finances, right? In addition to all of the human interactions and yes building a network and shaking hands and kissing babies it's all important referral networks very important but they cannot be the only if your why isn't strong enough to help you get through whichever one of those two humps really says oh my god that's so hard some people do that over finance right and again my wife and i she hates the finance part so we partnered right i did all of that right you got to make real investment in the the marketing sales side of things. And your why has to be strong enough to get you past that. If you go, well, that's okay. I'll get two out of three. I'll be good enough. My advice to people when they say that, I'm like, stay home, right? Go out there and stay on the grind, stay on the thing. You're not going to make it, right? I mean, you might get lucky, but that's not a plan either. And so, you know, part of what we will do is develop tools to help those people not have to experience the length of pain that they're feeling going through the marketing, arguing with themselves as to whether they're a salesperson or not, right? I'm very much guilty. I don't like sales. I don't like that thing. But something I believe in, like this company that Aaron and I are building or the products that are putting out there or a product that I have built that solves a need of mine when I am my own customer, I can sell the crap out of that.
SPEAKER_02:Sure.
SPEAKER_01:No problem. I got no problem. I'm an extrovert,
SPEAKER_04:right? No problem. So I was just going to interrupt. So one of the things that we wanted to accomplish in this conversation, even though we're not announcing the name of the company, is what are we actually delivering, right? And so you've heard Will and I talk about things from different perspectives. They're both unified in talking about what is necessary for a company. Will, who's not a marketer, has faced a lot of challenges in marketing. And so he has led the development of one of our first products that we'll bring to market that helps people to figure out what their brand authority is, how they go to market, what's the most effective story for them to tell. And it's good for someone because if I were to do it, it might be a little bit more clinical. I've been in marketing like my whole career. For him to do it, it really addresses the pains that he sees founders face. Whereas I'm more on the front end of how do you validate whether or not the idea that's in your head is the one to focus on. If you've got 20 ideas for a business that you could devote your time to, how do you decide which one is actually worth your effort? Or even which four? Because if you've got 20, chances are you're not going to devote all your energy to one. Do you have a systematic way to be able to say, okay, I need something, a system that to go out and validate these ideas for me such that when I wake up in the morning or look at it in a couple of hours, it's telling me, okay, of your 20 ideas, these are the subset that you probably have a real shot at winning. Now, you can. You can take that and run with it, or you can do the additional homework of going out and talking to real people, getting their input, refining it, and then now you're taking that four down to two or one. A lot of people need that. They feel like they need kind of an outside, unbiased opinion to know where they should invest their time and efforts if they're going to do this and be serious about it.
SPEAKER_02:Yeah, you know, one thing I'm thinking, and I'm just going to ask you as right now, but would you be willing to come back for another episode and we dive into that a bit deeper, maybe even show something that you've been working on if you're willing to, and maybe step through the process that people might go through. From the very beginning, I have an idea. I want to do this. And so begin to work their way through this and what it might look like. And I mean, I have a gazillion of them. But I also know that some of them are like, yeah, I don't think I'll fool with that. But, you know, I write them all down because I never know. But I think if we did that, it would it would be helpful for it could be helpful for a lot of people and certainly be helpful for me.
SPEAKER_04:There are two inputs that are required for for validating whether or not it's a good idea. One is, can you describe what the problem is you're trying to solve
SPEAKER_02:there? Here we go.
SPEAKER_04:And who are you trying to solve it for? And the more detail you can provide on those two questions, the better the outcomes.
SPEAKER_02:Yeah, that is outstanding. You just kind of went right to my heart here because I just went through this. I had this conversation with myself about a week ago and adjusting really my target a bit, you know, because I realized I was aiming a bit low. And once I up-leveled my target, I realized that the conversations were far different and far more advantageous for both of us. sides
SPEAKER_04:isn't that interesting too i find that that happens where first-time entrepreneurs tend to shoot low i remember when i first started doing the fractional work and i was thinking okay chances are my target by target customer, if you will, was going to be like the VP of marketing. Because I was thinking big corporations, whereas the person who actually found the most value was straight to the CEO's office.
SPEAKER_02:There you go.
SPEAKER_01:I do want to jump in and answer your question directly, Roy, is that absolutely we'll come back and play show and tell. I want to get that part on the record. And we can show you the path from idea that we're talking about. We'll start with the pain. from the pain to the ideation to the, I'm thinking about doing this for me, to let's validate it in the market and how we did it and who got to use it and test it and play with it, to, cool, I need to iterate and shift and pivot, and this is now what we've ended up with that we think is there. And then to the next possible steps, right, is, oh, okay, so here's how these two ideas that we have can dovetail and become reality. something even greater. So we definitely have a story that we can tell to those ends.
SPEAKER_02:Well, that's great. I think if we do that, that'd be beneficial. And we can talk about some of the other things that come up in that because, you know, we don't have to dive into this right now. Maybe save it for the next one. But, you know, the whole vibe coding thing, you know, people, again, right, jumping in with an idea and knocking something out. There's a whole lot of issues with it. Let
SPEAKER_04:me just say this. I love vibe coding. We are not anti-vibe coding. We're just pro software business. And my coding does not always mean you've got a business idea. That's it. That's it.
SPEAKER_02:That's for sure. Well, there's those issues. And then you get into some of the technical pitfalls as well. I'm on a couple of online boards, right? And basically I see people that are, I'll refer to them as newbies. And I don't mean that in a disparaging way, but they're new to software development. And they're finding that it ain't quite as easy as they thought it might be. You can get to 90%, 95% and then it's like, I'm stuck and I'm in the death spiral here, eating up all my tokens and I can't get out.
SPEAKER_04:And that's where having a seasoned team of actual technologists, sometimes you're going to be able to go forward with your no-code stack. In some cases, that will be the case. It may even be a lot of the cases. But in some cases, there's enough complexity that having real humans who've built real software products is going to be the answer. And for that, even if you've ever been in product, which I know both of you have, one of the hardest things to do is to translate the idea of the visionary product guy or even CEO to the developer who has to go create it. Even if you can give that working prototype to the development team and say, this is what I had in mind, You cut so much time and frustration out of the development process.
SPEAKER_02:It's phenomenal. I totally agree with you. Because, you know, a picture is worth a thousand words. Go ahead, Will.
SPEAKER_01:Back to the vibe coding, and we'll just talk about chatbots in general, right? Chatbots, they want to please the person asking questions. This is the way they're set up. They will lie to you. And then they will admit they lied to you. If you say, is this based in fact? It's like, oh, oh, well, you want a different answer then. And your dev partner vibe coding thing, the solution that it offers is the one that's at the top of whatever priority it came up with has nothing to do with the logic of what you're trying to build. And so this is where, like Aaron said, having the skills, even my skills as a coder, which are greatly atrophied, have already shown to be beneficial with vibe coding. And then you take it to the next level with someone who's still active, it does make a difference. But like you say, not anti-bind coding at all. Very, very high and positive on there because there's lots of benefits as long as you're going to properly balance it with a
SPEAKER_02:company. Yep. Good. All right. Well, look, let's go ahead and we end here and then we'll come back and really get into this process of taking an idea and working our way through that. And we'll see what some of what you guys are working on. But I think this is a great, great introduction to not only the topic, but then helping people to move along because this is a real thing. It's a real problem now that people are facing and anything that we can do and whether it's even some small way to help folks would be a fantastic thing. So I thank the two of you for your time and your energy in this and we'll get back together soon and we'll knock out this next episode and who knows where that will lead.
SPEAKER_04:Roy, thanks for making your platform available to us. We really appreciate it. Thank you. We do appreciate it.
SPEAKER_00:All right, guys. Thanks. Bye-bye. Thanks for listening to Midlife if you enjoyed today's episode share it with someone ready for their next chapter make sure to subscribe for more inspiring stories and practical advice want to connect or share your journey visit us at midlifekicker.com remember it's never too late to kick open a new door see you next time
