Running Your Own Business at Any Age: From Making the Initial Leap to Growing From Me to We

Join Arsenal Financial advisors Doug Orifice and Jeremy Vaille as they open up their relaxed office conversations about various financial topics for everybody to hear. This episode they get together to discuss the realities of being an entrepreneur.  Listen to learn about:

• Doug and Jeremy's own journeys from corporate jobs to the entrepreneurial world
• The traits and habits that can drive small business owners --- and hold them back
• Learning to trust others with a piece of your business pie
• The importance of having a realistic timeline for your business
• The average age of a business founder (the answer might surprise you!)
• Then finish up with some dad jokes from Jeremy.

Learn more about Doug, Jeremy, and Arsenal Financial at arsenalfinancial.com or call (781) 335-9100.

Securities and advisory services offered through LPL Financial, a registered investment advisor. Member FINRA/SIPC. The information in this podcast is educational and general in nature and does not take into consideration the listener’s personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice. To determine which strategies or investments may be suitable for you, consult the appropriate qualified professional prior to making a final decision.

Transcript

Doug: 0:04

All right. Well, thank you everybody so much for tuning into yet another episode of the Arsenal Money Clip. It's a gorgeous Friday here. My name is Doug Orfice. I'm a financial advisor here in Watertown, Massachusetts, with my pal and partner, Jeremy Vaille, who's hanging out in Norwell, Mass. We are investment advisors with a firm called Arsenal Financial, co-headquartered in Watertown and Norwell. Jeremy, TGIF. Thank God it's Friday. It's mid-March and we're in a turbulent market right now, right.

Jeremy: 0:33

Yeah, yeah, I love almost spring Fridays. Ball's starting to ramp up. I'm looking forward to that for the first time. How are you doing?

Doug: 0:41

I'm doing good. I'm doing good. You talk about youth sports and baseball starting to ramp up and everything, and soccer and getting out in the field. I got to tell you, man, the last couple of months, I think you and I would agree we've delivered a lot of financial therapy to folks since January 2nd. You know, holidays were nice this year, but it's been a stretch. It's been a stretch.

Jeremy: 1:03

It sure has yeah.

Doug: 1:05

But when we get back to our coaching roles for youth sports, you know it's pretty cathartic, isn't it? (Jeremy: Yes) We leave this stuff on the sidelines, literally, and kind of just focus on the kids. It's good stuff.

Jeremy: 1:15 

Looking forward to it, yeah that's for sure. 

Doug: 1:18

So but you know what? This is a listenable podcast about money. We try to make it a listenable podcast and we're not really going to talk much about markets today, despite the fact that we are in a turbulent stock market environment right now.

Jeremy: 1:30

We're in a correction now.

Doug: 1:31

We are officially.

Jeremy: 1:33

When we were recording this podcast last month, we were at an all-time market high. Just like that.

Doug: 1:38

Just like that. 10% in a month. This is being recorded on Friday, March the 14th, 2025. And you'll probably listen to this sometime thereafter. But we're going to take markets, we're also going to put that mostly on the sidelines today. Dude, what are we going to talk about today?

Jeremy: 1:54

Small business owners.

Doug: 1:58

Small business owners, entrepreneurs. This one is near and dear to your heart and mine. It's really you know what we wake up and do every single day. So I think what we'd like to do is just take the next 40, 45 minutes, maybe talk a little bit about our journey as entrepreneurs, very briefly. Talk about entrepreneurs at large around the world, but mostly here in the US, right, and some of the things that entrepreneurs and business owners have in common, some of their struggles, maybe some of the things that you need to do, especially when you're a new entrepreneur. And then also some interesting statistics about what an entrepreneur in America kind of looks like. But this one's near and dear to us, so you know, if you're randomly listening to this podcast and you're in Wyoming, or if you're one of our clients, you may or may not know our story.

Doug: 2:42

Both Jeremy and myself used to work for really large companies before we decided to go and work for ourselves. On my side of the coin, I was a financial advisor for larger institutions American Express, Bank of America, Merrill Lynch for 12 years. And JV, you've heard me tell this story and you've gone through it yourself. I got kind of tired of it, right?

Doug: 3:06

Really understood that I enjoyed core aspects of what we do over 12 years. Helping people working their way through the difficulties of markets, putting together the puzzles that are individuals' financial plans. I didn't necessarily love being told how to do that. A big bank or a big brokerage's rules didn't exactly suit either me or my client. So, anyways, in 2010, on a Friday the 13th, nonetheless, that was the day that I decided I was going to be one of America's entrepreneurs. 

Jeremy: 3:40

How old were you at the time? 

Doug: 3:41

Oh my God, how old was I? Let's see. That was 2010. I was 32. I was 32. And, yeah, at one in the afternoon, Friday the 13th, August 13th, 2010, I quit.

Jeremy: 3:53

Just cold turkey, no plan?

Doug: 3:55

I came in in like a t-shirt and shorts which was the first time I had ever done that at Merrill Lynch and it was a hot August day and I knew I was going to be making phone calls and putting together furniture and whatever over the next like 72 hours. So I was ready to get in the trenches. Walked in, I quit. But I had planned ahead, knowing that at that point I had a client base that I was fortunate enough to build a relationship with over a number of years and I had really decided to build a business around these families, creating a financial planning business and developing investment strategies around those individuals and those financial plans. So I quit, man. And then that day a 1.3 person business was started. I had one of my best buddies who runs a brewery who wasn't running a brewery at that time came on to help me because he used to also be a financial planner as well in a prior life and helped me set up a business.

Doug: 4:49

But anyways, it's 2010 that I decided to be an entrepreneur and then I'm going to kind of fast forward the story because we want to, we want to get beyond you and me, right. Five years later, I was a one man show and I realized being a one man show entrepreneur can be lonely, can be frustrating. You realize you're wearing a million different hats and I think that's where I decided that I needed at least somebody else in the room. And we needed an operations pro. And this is going to be year number 10 that you and I have had Heather Harris, our operations MVP, in our business, right? So Heather came on that year.

Doug: 5:25

But long story short, that was the first puzzle piece of starting to de-me the business and start to make it into a we. We brought on Chris, one of our advisors. You came on in 2019, you'll tell us a little bit of your story. But I think one of my greatest lessons in the last 15 years of running this business is that it needs to be more than you. It is too hard generally in most businesses to just go it alone, even if you are a one person business where you do all the work, man, to have a network is helpful. To have vendors to do some things is helpful. To have tech that can take some of the work off your back is helpful.

Jeremy: 6:02

I mean to break into your monologue there, though that's what our conversations that started this podcast are all about. Right, having each other to bounce the ideas off, of having each other to talk through things. Right, because, like you said, that lonely element, especially here, right, when things are out of your control and you're wearing the weight of a lot of clients on your shoulders, it can be rough by yourself.

Doug: 6:22

I think you bring me to one of my biggest points too is in this from going to me to we sort of journey, one thing I didn't really have was like a partner and equal right, and then somehow I forest gumped into you through a client. And JV, why don't you tell the random person in Wyoming listening to this podcast how the heck you got into this business.

Jeremy: 6:43

Totally atypical is what I'd like to say, and I think my entrepreneurial story is kind of bookended hopefully. Hopefully this is the last of a long bookend. But my parents started a small landscape company probably in the late 70s when they started it. I mean it's been successful for 40 years, but it's ranged from one person to probably its peak in the 90s. But they worked in it together.

Jeremy: 7:04

So you can imagine what conversations around the dinner table were like right. My dad's coming in from the field, my mother was working in the office and they'd be kind of rehashing the day at the dinner table. So lots of conversations about the way the world works in a small business. But they never wanted that for me. So they urged me to go to college, they urged me to not be a landscape business owner and you know I ended up being an engineer for a period of time, like you always say, my recovering engineer status right. So did that for a good 10 years or so and then found my way into a corporate role at Fidelity, you know, coming from a large corporation like Boeing and Lockheed Martin, these massive multinational corporations with hundreds of thousands of people and kind of finding my way as somebody that has an entrepreneurial spirit and trying to be a cog in a huge wheel. So it's like, how do I navigate that? And I didn't do it very well.

Jeremy: 7:59

To be perfectly honest with you, it didn't feel right ever in the aerospace world and then in the large financial services space, and got such to the point where, you know, in my late 30s, I'm like I'm in my midlife crisis. I need to do something different. I don't know what to do from here. I don't like any of these jobs that I see in front of me. So, you know, I have a brand new baby, I have a wife, I have a house and a mortgage. I'm kind of in the middle of my career and, man, it feels like I've started over a couple of times already. Do I really want to start over again? And that's exactly what I did. Thirty nine years old, 2019, let's press the reset button and do something that's really meaningful and purposeful and that's helping small businesses and families to really move the needle in their financial lives and help them achieve some of their goals.

Doug: 8:45

And I have had more than a front row seat for all this, and might I say you are the perfect fit for this walk of life, absolute, perfect fit. At the beginning of your seventh year in this journey right, and your evolution in this has been like a hockey stick. So here we are, right and this is really cool.

Jeremy: 9:02

One last point I couldn't have done it without a great mentor. Because if I was, out on my own. It would have been rough. It is rough, right, we've gone through a lot of rough patches over those seven years and thank God I have you along the way because it is a lonely place to be. I can only imagine, if I'm by myself out here, what that's like.

Doug: 9:19

High five my man. Doing this now makes it fun right. Which I think gets to the crux of all this is you and I have been through the journey. We're now part of a five-person team and something that we've built that I think you'd agree we're really proud of. And we still find struggles, like literally every single day, every single week. It's never a completed product. So we get it and we empathize, right. And if you go on our website, we get these three little medallions that kind of talks about the different folks that we help. We got our T minus tens, which is our little nickname for those who are within 10 years of retirement. We got our busy families which man does that describe our peer group in our lives. But then we got small business owners, because we get it. It's hard, that's hard. Let's jump into that. You know like I don't think being an entrepreneur is for everybody, but you smashed me with the stat earlier this morning that kind of blew my hair back. How many entrepreneurs are on planet Earth allegedly?

Jeremy: 10:14

According to my half-assed internet research, as of 2024, there were 600 million entrepreneurs worldwide, which is 8% of the world's population.

Doug: 10:23

Wow, 600 million entrepreneurs, right, and that's from like the sausage guy to Bill Gates and everything in between. Unbelievable. But you know, sausage guy, and you and me and Bill Gates all have something in common. Bullet point number one on my piece of paper right here, usually an entrepreneur has some sort of self-starter-ism in them. More often than not, at least for a period of time, it's all on you. When the concept of your ideas is in your head and you're trying to get it onto paper or onto a spreadsheet or into real life, it's all on you. And that all on you thing it's a lot of pressure, right.

Jeremy: 10:59

Well, I think one of the things is you're expected to do one thing with the widget. So you've got your one job and you do your one job. When you get out in this world, you've got a million different hats you got to wear all at the same time.

Doug: 11:10

So, like to your point, let's go into your engineering world, right? Let's say that you decided to stay an engineer but you became a consultant for whatever it is. A certain component of how satellites need to be designed on, I don't know step number 61 through 73 of however the hell satellites are put together. In doing that, you have to do that work. But then now you are doing your own finances for the business. You now have to go choose your vendors. You have to manage your own time. You have to manage project to project, because you may have one client for a six month period and then maybe you move on to another gig, right?

Doug: 11:50

I like to frame it this way for folks, you know my wife works at a big hospital in Boston. If you work for a hospital and you're a nurse or you work for I think of large employers that we have here in Massachusetts, like Raytheon or Big Pharma maybe, just maybe, you have a more linear career, right? So, like when you and I are putting on our financial planning hat and our retirement income hat, it's a little bit easier to project out. For our entrepreneurs, it is not linear, sometimes it's a mess. It happens in chapters. It changes from year to year. It's extremely dynamic and then because of that, when you're an entrepreneur, I think you have to learn to build a certain amount of patience and flexibility into the soup to make it happen.

Jeremy: 12:35

And I mean not to use the market analogy, but I was talking about one of our entrepreneur clients this morning, talking to him about how clients want the markets to go up and to the right in a linear fashion. They don't like it when there's a 10% correction. Because that doesn't feel good, but it's required and necessary and normal. Right, and it happens. And it's similar in the entrepreneurial space. Right, it's not going to go on a straight line.

Doug: 12:59

No microcosm, right? I sit here on Mount Auburn Street in Watertown. A mile down the road there's a whole bunch of construction right. Because of construction, a lot of our friends in the business community here their numbers are off 10, 15, 20% just because there's construction equipment sitting in front of their businesses. The roads are messy, parking's crappy, right. And we're also at a time, too, where people are thinking twice about what they're going to spend on a cup of coffee or a fitness class or a night out or whatever it is right. So even just the nature of running a business, you immediately pull yourself out of the linear income model. What's our phrase? You, and I like to call it, you've gone from linear income to lumpy income.

Jeremy: 13:36

Right, yeah, exactly. Not the same anymore.

Doug: 13:39

So that's one thing, and you know. I think that, combined with the fact that I like your explanation that when you have the corporate job usually you're responsible for like one function, one corner of the world. That may be a larger business or one piece of the pie for a small business, whatever it is. If you're starting this yourself and it's your baby and it's your idea, well, you want it to turn out a certain way. So I think sometimes the natural disposition is I have to steer the ship for everything. I have to be in control of everything, and it's hard to bring others along and start to give them that rope and give them that trust. And I will say, from even just thinking about our business, I am so thrilled over the evolution of our business in the last five to eight years by just completely giving somebody a piece of the pie and saying run with it, you know. Just being open enough and honest enough with yourself to be like, hey, you know what, this piece of the pie, I've analyzed it and I suck at this piece of the pie. I don't have the skillset to master this bullet point, this bullet point and the 15 after it. And hey, your resume says you're pretty good at these things. How would you like to come on and make this your own? That's what's been great about our business, right?

Doug: 14:54

We're doing a podcast right now. Are we recording this thing? No, our buddy, Matt Hanna, is recording this thing right now because he's a pro. We just get to show up, which is great. So I think one of the things I've enjoyed in 25, 26 years of doing this and having clients in all kinds of different businesses is when they do have success, watching them build a team to watching them create a culture. Sometimes it's a culture within a five to 10 person business, which I've seen that a bunch of times. You and I have some clients that have, like you know, 30 to 50 employees and there's a really cool culture going on and we get to see everybody on the same page and that's really really neat to see. And that kind of is, to me, an example of having the trust to go, hey, here's this piece of the pie, run with it, and understanding that you need a little bit of trust and you need to let go a little bit to have others buy into the same goal.

Jeremy: 15:47

Yeah, that delegation is tough, you know no doubt about it. You have so much more skin in the game, right, like you said. I'd say just anecdotally for me, like one of the hardest things was how do I get clients? I didn't have to get clients. I didn't have to get clients when I worked at Boeing right. The government bought the product. I didn't have to go get clients. Same thing working at home office at an investment firm I didn't have to go get clients. But that was something that scared me and was something that was one of those stretch goals that I had to overcome when I jumped ship.

Doug: 16:16

Yeah, absolutely. One of the things that I think that we all have to overcome when we’re starting to build a team is, people don’t work for free. Right, so you and I are in the investment business and the reason that we're in the investment business is if you put money under your mattress for 20 years, you put $100 on your mattress for 20 years. First of all, if you flip the mattress every so often, you may lose that $20 bill. Second of all, best case scenario, you find it and it's still $20.

Jeremy: 16:45

Full of dust, mites 

Doug: 16:48

Full of dust mites and everything right. So our goal is to help people grow capital over time, outpace inflation, outpace the cost of stuff, so that they can achieve whatever it is, usually retirement. So when you're hiring somebody, the way I look at it is you're making an investment in your business. You can only scale so much when it is just you. Even from like a tech point of view, let's say you have a one person e-commerce business, you are not doing necessarily all of the coding and doing everything yourself. You are finding six, seven, eight, ten different technologies that you're putting together so that you can scale that idea.

Jeremy: 17:28

You're buying back time right. Well, when I talk to clients, it's skill, will, or time right. Similar kind of concept, right.

Doug: 17:39

And the time one, and we're constantly facing this because we're constantly running out of time. When we run out of time, we have to make a decision right which is like, okay, how do we buy back time? Do we bring on another part-time person? Do we bring on a technology? So I think there is this piece of getting over the scariness of spending money on your business and understanding its impact over a certain period of time right. Like if you hire somebody who serves you know an operations management function so that you don't have to be in the operations business, although that may cost you X, will that allow you to grow your business or buy back time to do some of the things that you want to do? We have some clients and you know people in your circle and examples that you've seen where sometimes that doesn't happen, and you watch people either run out of time or revenue starts to stagnate because maybe it is too scary for some folks or the finances aren't quite there.

Doug: 18:32

But I think that's one of the themes I see over and over and over again with successful entrepreneurs is not being afraid to invest in your business if it's something that you believe in, if it's something that you can see working, but your limitations are your own personal time and bandwidth and sometimes skill set.

Jeremy: 18:51

Right, that's where the mistakes happen too.

Doug: 18:53

Yeah. So I always put this in the me to we framework, right. If the t-shirt is like, hey, I'm one of these 600 million entrepreneurs, how do I take it to the next level? Really part of that is going from me to we, building a team. And sometimes building a team is not always having a W2 employee. Sometimes it's a technology, sometimes it's coaching, sometimes it's a vendor right. Like you and I even play that role with clients where it's like, hey, all right, I need to replace the 401k plan that I used to have at Dell. How do I do that? Okay, cool, we'll do that for you. And when they're like, oh my God, I have to pay somebody, what do I do? Well, hire a payroll company and maybe it costs you 1500 bucks during the year, but it's done right, and you buy back this time and you're done.

Jeremy: 19:39

It's fortunate that we're able to advise and consult with clients in that fashion and it's because we've actually been through that and done that. That's a good thing to have. But I also appreciate having that corporate experience, because a lot of our clients have jobs, work for big companies, right. And that's been empowering for me is to be able to kind of help them navigate some of those conversations with their bosses or management and trying to fight for themselves and get those raises, get those promotions. And get them either switching jobs or staying with what they're doing and then also giving them the conviction or empowerment to make that leap to the entrepreneurial world when they have that desire to do so.

Doug: 20:16

I want to hit on something in just a little bit. When you talk about making that leap too, about maybe some of like the demographics age wise, about what that looks like, because you found some really interesting statistics. But before we do that, too, I think there's another element we want to think about too, which is, you know, like time's crazy. So you know, you and I are in our mid 40s.

Jeremy: 20:35

Is it still mid?

Doug: 20:38

It's still mid. I'm 49 and a half whenever I hit that, that's still going to be mid 40s, right? I mean, I have a seventh grader who tells me I'm mid all the time. But I think that just means that means I suck. 

Jeremy: 20:49

Are you trying to be cool, bro? 

Doug: 20:51

But you know we're always talking about the newest creak in the knees or doing stuff now while we can and just kind of our point in life. And part of that brings me to the just understanding that any time that you either start a business, think about altering your business, grow your business. Two things. A, there's a time component where you need patience. It's not going to happen overnight. It takes time. And then there's a timeline to it.

Doug: 21:19

I got this great quote from a client of mine almost 15 years ago. He was starting a business and it was finally starting to take off. He was starting a business and it was finally starting to take off, and we just had this great conversation about the point in which you start to spend a little bit more money to take that leap, or when you're first starting your business. And he gave me this great analogy that you know I use all the time, which is the F-15 jet analogy. Which is you get an F-15 on an aircraft carrier. When that F-15 takes off from that aircraft carrier and finally leaves terra firma on that aircraft carrier, the first thing that happens is that beautiful jet falls, falls, gravity pulls it down. Sometimes those wheels are skimming the ocean right, and when I even think of that I'm like, oh my, my God, like that is, that is the scariest concept ever, you know. But these planes are designed to fight gravity, skim the water, and then have this incredible trajectory towards the skies right.

Doug: 22:17

And a client of mine kind of gave me that analogy. That you know, when you first start a business, when you first start spending money in your business, when you first start trying to grow it, it's like an F-16 leaving an aircraft carrier.

Jeremy: 22:28

Right, like that leap of faith, right? 

Doug: 22:29 

Yeah, so you have, like the first, after you're done, the concept phase, there's a I got to spend money and I may or may not have revenue. So, from a growth point of view, there's these chapters where you have initially concept, then you have aggressive growth, right. Like aggressively trying to whatever it is grow your client base, grow your revenue, grow your idea. And then you get into the sort of mature growth phase. And then you and I are even working with clients on the several chapters beyond that, which is all right, you know, if you own your business for 20 years, right, at some point you're going to exit or hand it off or sell it or something.

Jeremy: 23:09

Equally scary to the launch is landing that beast. I mean you're looking for the catch wire, with 70 foot, you know, 50 foot seas.

Doug: 23:15

So to your point. You know two of the scariest things launching and landing that plane. So I think one piece of advice I'd give to somebody who is, either, you know, a new business owner or you're thinking about the next chapter of your business, whatever it is, is timeline. You know, think about the timeline of your business. If your business is brand new, great, you know, like be real with how long it may take for this to maybe replace your corporate income, or how long it will take for you to kind of reach a point where maybe even you can't do it anymore or you have to bring on somebody else. Mapping out timeline to me is one of the most important things that you can do as an entrepreneur. Helps you plan.

Jeremy: 23:55

Yeah. And I feel like I poke you every few months like, hey, how long are you doing this, what are you doing at the end of this?

Doug: 24:01

And it's good because I got to think about it. I'm like you know, I don't know. But I think one of the things that is helpful, even for us in business, is starting to think about like, okay, if we don't know what 10 years looks like, what's our best guess at 10 years? Let's back that into, all right, well, five years is easier to see, so let's map out what five years from now looks like. Maybe we'll even dial that back into three and into one year. One year, you can see, okay. And if we want to make X progress in the next one year, great.

Doug: 24:29

What changes do we have to make in 2025 to do what we need to do? So timeframe, timeline, I believe super important. Just a combination of just having some patience and understanding that things take time, whether it's an investment in a technology, investment in a vendor, investment in a person, and understanding the bigger picture timeline that you know at some point, if this has gone well and you've done this for 10, 15, 20, 25 years, then there's an exit period too, and just maybe understanding way ahead of the curve what does that look like.

Jeremy: 24:59

And that patience piece is a good one, because that's really hard. I mean, especially if you're an entrepreneur type. Certain mindset, certain, I guess, characteristics of an entrepreneur. Patience is probably not high on that list in most cases. 

Doug: 25:10

Because you probably didn't have patience with your corporate employer, right. 

Jeremy: 25:13

Right. So and you know, maybe you're mid-career like me. I didn't have the patience. I didn't want the patience. I wanted to get in there and charge hard and get up to speed as quickly as possible. But you know that's not the way it works. You're going to have to log the time and grind through the ups and downs until you can get to a sustainable place.

Doug: 25:32

You know, this is a really good segway to maybe just get right to our mythbuster of the day. Because you did some good research here, something that we talked about a couple weeks ago. Right here we go. Bust this myth. JV, I'm too old to be an entrepreneur. Fact or fiction?

Jeremy: 25:52

Well, let's just say right away it's busted.

Doug: 25:57

Busted. Wait a minute. You're busting it without, where's your supporting documentation? I don't believe you.

Jeremy: 26:01

Yeah, no supporting half-assed internet research yet.

Doug: 26:05

Yet.

Jeremy: 26:06

I busted this myth. I thought I was too old at 39, right. I'm thinking, oh my goodness, I'm almost mid-career. Okay, I got 20 years, that's a good run. I'm going to do at least 20 years, probably 25 or 30 if things don't go the way I want them to. So that's plenty of time to start something and have it be successful and give it a go. I was 39 at the time. According to Harvard Business Review, the average age of a founder, 42 years old.

Doug: 26:32

It's incredible. And it makes some sense, right? Because if you're going to start a business, granted, you have less to lose when you're 25, but your real world experience is not that much.

Jeremy: 26:46

And I'd argue my ramp up was a lot faster because of that experience. 

Doug: 26:51

Correct. Your ramp up was fantastic and we've seen this a whole bunch of times too. Like I've seen this multiple times over the last several years is some of our clients who are late career and then have a catalyst. Catalyst could be they retire. Catalyst could be they get laid off. And it's almost like they're forced to that fork in the road. And I've seen people in their 50s, I even have a client who is in his 70s, having started a business and running a business and having some fun with it.

Jeremy: 27:20

Yeah, I'm going to take this stat with a little bit of a grain of salt because it sounds too magnificent, but 51% of business owners are 55 and older. 

Doug: 27:30

Say that again 

Jeremy: 27:31

51% are 55 and older. Now in the tech industry it skews younger, but these are the more traditional type businesses where it skews older. Because of that experience piece right, you're already an established career person, so you've got kind of an ability to kind of transition into an entrepreneurial space.

Doug: 27:49

And what's interesting about that is by that stat, you are telling me that more than half of entrepreneurs are thinking about an exit plan.

Jeremy: 27:56

Yeah, good point. Couple more fun stats just to kind of throw into this I'm too old to be a business owner. Those that do jump into entrepreneurship, 58% of them worked in the corporate world. So similar to our experience, yeah, which makes a lot of sense, right? Because you get that real world experience and then you've got that to carry into your entrepreneurial endeavor. But here's the good one.

Doug: 28:19

You love this one. I know where you’re going.

Jeremy: 28:19

Because this was the hardest thing in the world. by the way.

Doug: 28:24

I agree, I hear you.

Jeremy: 28:25

Hardest thing in the world I've ever done, and I've done a lot of hard things, but this was probably the hardest thing I've ever had to do. Patience-wise, time-wise, all the things, right. 96% of people who are self-employed have no desire to go back to a regular job. 

Doug: 28:39

It's a beautiful stat.

Jeremy: 28:41

Isn’t that fantastic

Doug: 28:42

That's a killer stat. I love it.

Jeremy: 28:44 

And one of my things I said is I wish I did it earlier, because I don't ever want to go back to a regular job until I do it for fun.

Doug: 28:50

Right, exactly, you know, and we get some time to think about that.

Jeremy: 28:53

So busted, busted.

Doug: 29:00

But I think this all gets to this is why we like helping small business owners because we get it. We've been there, we've been through the scary stuff. We continue to go through the scary stuff. You know, I'm pretty proud of what we've built too, so I feel like somebody who is starting something new or in the middle of changing something, I feel like we have some insight to lend. We certainly have a piece of the pie that clients can off board to us and not worry about it, right, which is again, I go back to your stat, which is what, 51% of business owners are 55 or older. So more than half of entrepreneurs are thinking about an exit plan. So you and I are often talking to our entrepreneurial clients about, all right. Well, not that we want to rush you out of your business, but how much time do you have left? I don't know. I could do this for 10 more years. Great. Is this a business that you can sell? Is this something that you would hand off to your right-hand person? And that's fascinating and fun, because these exit plans are never the same. Some of them rhyme a little bit. But I enjoy helping somebody who is maybe 5, 10, maybe even 15 years away from that exit plan, way, way, way in advance, so that it's not a surprise when it finally comes.

Jeremy: 30:17

Anecdotally, I have two clients started a business in the last year, both 50. 

Doug: 30:23

Awesome. So maybe, if anything, if you know, for the random person who's in Bend, Oregon, is it Oregon or Oregon? If you live in Oregon, or Oregonian, Oregonian, I don't know I guess I'll pronounce it like I would Oregon, Oregon, Oregon, whatever it is. But if you're in Oregon listening to this, right, you've been on the fence about starting your business, maybe this helps. Why not? You know it's OK if you're 48 and starting your business. It's OK if you're scared. You have the time frame, the tools, the patience. You know life is short. Give it a crack.

Doug: 30:56

One of the things I'm lucky enough to do here in our community in Watertown is I help to run a small business association and I am continuously learning and am impressed by all the different business people and those who run nonprofits here in our city. Most of them have a fabulous story and a lot of them, I think embody what you're talking about too now I think about it. A lot of them are 40s, 50s, absolutely second career, if not third, and just a lot of high energy, creative people who have many skills, but maybe not all the skills to run their business and all the time in the world to run their business and have made that leap to hire others, grow, change, pivot, which is really cool.

Jeremy: 31:35

Hey, you're not spicy today. Do you have anything spicy?

Doug: 31:38

No, you know, I actually feel pretty good about this. I think the spicy segment, which was, you know, the thing that gets my blood pressure up a little bit, would be the reluctance to outsource or insource, which again, is hard. But I feel like we covered that. You know, Friday, mid-March, tough market, a lot of people emotional right now. I'm feeling pretty optimistic after this conversation, right. To your point, you just said this is the hardest thing you ever had to do and you also said that many entrepreneurs get started in their 40s and 50s and most of them are over 55. So damn, like I'm not spicy at all today, man, I'm feeling pretty good. I'm feeling pretty good. It kind of makes me think about a lot of people in our circle who, like man, like I'm proud of them. I'm proud of Matt Hanna, who's to my right over here, who's running, what are you running 17 businesses, Matt. You know, giving to our community, using his talents. In every single community there are just incredible people giving their energy, doing it kind of on their own or with their team. I don't have a hat on today, but I wish I did, because I'd be like hats off to entrepreneurs today, you know.

Jeremy: 32:44

Yeah, yeah, definitely kudos to them.

Doug: 32:47

No matter where you are. If you got a question, you want to talk to Jeremy or myself and talk about your story a little bit, maybe even come on a future version of this podcast to talk business, because I think we should revisit this maybe sometime later this year. Drop us a line. You can find us at info at arsenalfinancial.com. You can feel free to give us a buzz. We're at 781-335-9100. Check out our website at www.arsenalfinancial.com. This was fun today, dude. This was fun.

Jeremy: 33:15

You're forgetting your favorite segment.

Doug: 33:17

Oh my God, I did almost forget it.

Jeremy: 33:24

Daddy, don't try to be cool. Don't try to be cool, bro, with your dad jokes.

Doug: 33:30

Let's do it, dad. Where's the joke? 

Jeremy: 33:32

All right, I got a couple.

Doug: 33:33

Hold on Matt and I gotta stretch real quick.

Jeremy: 33:34

And I tried, as always, tried to make it pertinent to our topic of conversation. Well, I got three here. Why did the can crusher quit his job?

Doug: 33:47

Matt, why did the can crusher quit his job?

Jeremy: 33:51

He wanted to start his own business. But there's another reason.

Doug: 33:54

He didn't want to get canned.

Jeremy: 33:56

Because it was so depressing.

Doug: 34:01

Oh, Matt's shaking his head so much that he almost did like the exorcist thing.

Jeremy: 34:07

This is a good one that I think will be pertinent to you. You'll enjoy it. What is the role of stock analysts? 

Doug: 34:15

What is the role of stock analysts? I'm coming up zeros.

Jeremy: 34:22

Okay, making weather forecasters look good. 

Doug: 34:24

Wow. What's three? 

Jeremy: 34:39

All right, last one, wrap it up, bring it full circle. What sort of money do you need if you want to start your own landscaping business?

Doug: 34:39

Huh. I don't know, but it better be green. Seed money, Matt says.

Jeremy: 34:42

Pretty good, pretty good.

Doug:  34:44

Was it seed money?

Jeremy: 34:45

A hedge fund. I think actually the seed money is way better. Way better answer.

Doug: 34:52

We're giving Matt a full point on that one.

Jeremy: 34:55

He gets to rewrite the joke. 

Doug: 35:00

Oh man. This was a good one today. I'd like to give a shout out to Matt Hanna, who is always good enough to record our podcast. Matt has a business called Little Local Conversations. I just want to give a shout out to that. Little Local Conversations is a really really cool podcast which has started here in Watertown and Matt takes some time to interview different people across our community. Really really cool. And Little Local Conversations just turned, drumroll. One year old. Happy birthday Little Local Conversations. Proud of you, Matt. Thanks for all you do and you're another entrepreneurial success story. So JV and I'm proud of you too, man.

Jeremy: 35:36

Thanks, I'm proud of you.

Doug: 35:38

Thanks for keeping me company in this journey and you know it's a lot more fun to do this with you and with our team than it would otherwise be me pounding away at a desk and maybe not being as happy. So thanks a lot. All right, until next time. Thanks for tuning into the Arsenal Money Clip Podcast. We will talk to you next time around, see ya.

Speaker 3: 36:21

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