Hoops & Crumbs with the Browns
Hoops & Crumbs with the Browns" is a one-of-a-kind podcast that brings together a 40 something-year-old mom and her 15-year-old son for authentic conversations about life, culture, and connection. Set in the warmth of their home, they dive into topics like today’s hip hop scene, the highs and lows of basketball, and what it’s really like to be a teenager growing up in today’s fast-paced world—all while eating homemade cookies.
Hoops & Crumbs with the Browns
S2:E1 - Shooting Hoops & Chasing Dreams
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In this first episode of a new season, Esteban starts a series called "Shooting Hoops & Chasing Dreams" where he interviews folks about their careers as he starts to think about carving out his own path. With summer break winding down in 4 weeks, it's time to get that future mindset going again.
For the first installment of this series, Esteban sits down with Jeff, who shares his journey from corporate success to founding his own business, offering practical advice and inspiration for aspiring business owners. His story highlights how identifying market gaps and persisting through challenges can lead to entrepreneurial success.
Follow us on Instagram @hoopsandcrumbs with your questions for future episodes and join us next time for more basketball, cookies, and life musings. Send us a message if you've got an idea for who should be featured next for another segment of "Shooting Hoops & Chasing Dreams"!
Have a question for us to ask each other? We’d love to hear it!
Follow us on Instagram @hoopsandcrumbs and share your thoughts! We are always looking for questions to ask each other on the #doubledouble
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Season Two Kickoff
Speaker 1Welcome to Hoops and Crumbs with the Browns , the podcast where life lessons are baked in like chocolate chips . And I'm Maria Brown .
Speaker 2And I'm Estevan Brown . Together , we're always talking basketball , life and everything in between . Whether we're dunking on the court or in the milk , there's always something cooking . So grab a snack and tune in .
Speaker 1Wow , ezzy , it's been a long time . We took two months off of podcasting and now here we are with a second season . Do you even remember what we talked about our last episode ?
Speaker 2yeah . So the thing that I was talking to you about earlier , and I'll share with the view the listeners , is that , uh , the last episode the nba playoffs had just started . Now we're a month out of the nba finals crazy .
Speaker 1What were , do you remember , your predictions for the NBA playoffs ?
Speaker 2I actually don't remember my predictions . Probably had something to do with , like , boston and Oklahoma .
Speaker 1And are you happy with the outcome ?
Speaker 2Yeah , I'm a big OKC fan , so OKC OK .
Speaker 1Well , before we jump into the first episode of our second season , let's recap the last few months . What have you been up to ?
Speaker 2So the last few months I've been up to not too much really . We did a bit of traveling after the podcast in May I graduated , but aside from that , not really much . I mean just like some training . I went to camp and that's kind of it .
Speaker 1Yeah , I feel like May and June were super busy with going to your basketball games and recitals . Oh yes , lots of practice and games , lots of practice and games . Packing you up for camp , picking you up from camp , unpacking you from camp . Now we've got a bit of a break . Before you start up the grind again , what crumbs do you have in front of us ?
Speaker 2Oatmeal chocolate chip cookies made with dates and tahini , and Well , I don't have one right here , but I had one earlier and it was pretty good . But I'm not a big fan of tahini . It tastes kind of like peanuts and if you know me , you know I'm definitely allergic to peanuts .
Speaker 1I know they aren't my favorite , but we do have a guest here today . That gave them , I think , a 10 out of 10 . Before we introduce our guest , what are we talking about today ?
Speaker 2So today we're going to talk about what I want to be when I grow up and entrepreneurship . And our guest for today is the one and only Jeff Charlton .
Speaker 1So are you introducing Jeff now ?
Speaker 3Yeah , okay , do I go ? Hello , I'm Jeff . Hi , good to meet you .
Speaker 2And who is Jeff ? So Jeff is my stepfather and he's an entrepreneur who started his own business called Flexer .
Speaker 3And he is one of , as he's great admirers .
Speaker 1Well , this is going to be a great episode . I think it will be super interesting to find other people in your life that you can interview to understand their career path as you start to think about your own . So I'm going to take a backseat this episode and leave
Introducing Jeff Charlton
Speaker 1it to you . Gentlemen , how does that sound ?
Speaker 2Sounds good . Okay , you're ready for the first question .
Speaker 3Let's go .
Speaker 2Okay , when did you first decide that you wanted to be an entrepreneur ?
Speaker 3Long before I became an entrepreneur . It was funny because I mean , I was working in large corporations and I was selling lots of business . I hope my bosses are my former bosses aren't listening to this , but I was selling tons of work , literally in the hundreds of millions of dollars , and I was making a lot of other people very wealthy . And I kept hearing from folks hey , why aren't you doing this for yourself , why are you doing this for other people ? You're making all kinds of other people rich and you know how to sell , so why don't you do it for yourself ? And so it was something that I wanted to do for a long time .
Speaker 3The problem was is that growing up in the corporate environment , you kind of like in my world , I didn't really know a lot about small business , even though actually my father was a small businessman . I really , you know , getting university educated . So you know , I had an electrical engineering degree , an MBA . I really my mindset , driven by the educational environment I was in , was to go and work for large corporations , even though in my MBA I did take a small business course . But it was kind of like , no , if you want to make it , you got to go and work for a large corporate and you got to make it up into the senior executive .
Path to Entrepreneurship
Speaker 3And you got to make it up into the senior executive and , after being in that world for many years , I thought you know what , um , you , you , you know , I felt like I was a very small cog in a very big wheel and I got I you know , I was working with presidents of CEOs of , you know , large institutions , banks and insurance companies . So I had exposure to that .
Speaker 3But the more I worked it , the more I saw how political it was and how it was . You know , it was who you knew and it just was like a world that I decided . Ultimately I didn't want to be it . So I made the decision that I wanted to go into small business . But the problem was is I didn't know what I wanted to do . I mean , it's one thing to say I want to start a business . It's another thing to know well , how are you going to start that business ? What are you going to do ? How are you going to make money ? How are you going to be better than your competition ? What's your niche ? And so it took me a long time to actually figure out how I could start a business and what my niche would be and how I could be really successful .
Speaker 1What do you think of that Izzy ?
Speaker 2That's a great answer . You know , it's interesting to hear all that . And , like , from what I've heard , I mean I don't really know many other entrepreneurs , but from what I used to think mean , I don't really know many other entrepreneurs , but from what I used to think it was you wanted to be an entrepreneur because it's like your dream , but for you is more about like , after you uh had your career , you kind of realized that that's kind of just what you wanted to do yeah , and and I guess part of it too , was the recognition that when you're working in a large corporate , you're working for somebody else .
Speaker 3There's always somebody else pulling your strings . There's always somebody else who's making the ultimate decisions . If you're good at what you do , you make recommendations , they get accepted . Ultimately , you almost assume the role of your boss , and that's when you show that you're ready for promotion . But you know , I was looking at it and I'm going why am I making all these other people , like you know very well off ? Why don't I do the same thing for myself ? And so you know it was interesting because , uh , the way it actually evolved was I ended up running a number of high-tech businesses .
Speaker 3I ran three high-tech businesses , and so I was in a position where I needed a CFO , a chief financial officer , I needed a controller , a bookkeeper , I needed HR , I needed IT , I needed legal , I needed all the functions that make every company work . Now , that's in addition . Of course , the most important thing is sales and delivery , or sales and product , but there's all the backend corporate services that I just talked about , that every company needs to basically to launch and then to be successful , and what I was fortunate enough was . Having come from the corporate world , I recognized what a good quality controller looked like , what a good quality bookkeeper looked like , hr , it , legal , et cetera . And in each of these three businesses that I ran , I recognized that I needed people . It could be a day a month or it could be a couple of days a week , and there was nowhere that I could turn to to hire people on that basis . Because if you go to all the job sites you're looking like , typically they're for full-time people . It's very hard to go to like a job site like Indeed and say Typically they're for full-time people . It's very hard to go to like a job site like Indeed and say I want somebody for 10 hours a month . It doesn't work that way . And so there was no one in the Canadian landscape where I could say you know what ? I need an HR person three days a month , I need a bookkeeper two days a week and I need a controller a couple of days a month , that kind of thing . And so at first I thought to myself you know what ? Maybe it's me , maybe I just don't know how to run a business , maybe everybody else has figured this out . And so what I did was .
Speaker 3I was fortunate enough to be a member of an executive support group , which is essentially groups of presidents and CEOs , and I conducted focus groups of about 120 presidents and CEOs and I said to them guys , is it me ? I shouldn't say guys , it was ladies and gentlemen , is it me or do you all have the same kind of issues ? And 120 of them said , yeah , we all have the same issue . And so I recognized at that moment that it wasn't just me , that this is a common problem amongst small businesses and , like they say , necessity is the mother of invention . So when I saw this opportunity , with all these folks saying they needed the same thing , I thought , you know what ? There's a great market opportunity . And that was the eureka moment for me , where I realized , okay , finally I can break out of the corporate world , I can start my own business , I can be my own boss , I can go out on my own and I can tell you the next steps . But uh , I'll , I'll , I'll stop there . And and uh , let you ask the next question .
Speaker 2Yeah , that's . That's a great , that's a great answer , and it also gives the viewers a taste of what your company really does . So my next question what is the process like starting your own business , which you kind of yeah ?
Starting a Business: Method & Mindset
Speaker 3So so there's kind of the . There's the methodical steps that you can go through and I can cover those , and there's also the , the emotional process , and and you know what it's like , and those are two very different things you know . So , in terms of the process , you know , part of it is really getting up the guts to say , yeah , I can do this , uh , and I'm going to do this . And the funny thing is is that you know , you recognize , I recognized afterwards that there's 1.4 million businesses in Canada or thereabouts . So , like I thought about it afterwards , I go you know what ? I'm not paving a new path here . There's 1.4 million other people who have done this before me and you know what . There's a clear set of steps that you can go through . And then I started to inquire and quickly figured out okay , here's what you need to do . And the fun thing is is that it actually costs very little . So you know now we help other businesses get into business , particularly businesses from outside of Canada . We help them establish operations in Canada , and so , to answer your question in terms of how do you start a business , it's very much the advice that we give to these organizations . So the first thing is is know what your product and or services that you want to sell . And you know it's interesting .
Speaker 3I was at a networking event last night and I met a very fine , interesting gentleman from abroad and he wants to break into the Canadian market . Gentleman from abroad , and he wants to break into the Canadian market and he told me what he did and I said to him you know , there's a lot of other companies in Canada who do what it is that you do , but maybe you have something that's unique about your offering . But what you need to do is you need to look at the Canadian market first and get a good idea of what's already out there so that you can figure out how to come up with your own competitive , your strategic competitive advantage , what makes you different and better from all of the other options . And he goes . You know you're right , he goes . Thanks for letting me know he goes . I didn't realize that there were all these companies doing similar things to what we do , but that doesn't mean that he's out of the running . It just means he needs to figure out how he's going to position his company .
Speaker 3Then the next thing is to do some tax planning and people say , well , why would you do tax planning before you would incorporate the company ? And people say , well , why would you do tax planning before you would incorporate the company ? And the reason is is because incorporating the company . What that means is essentially you're defining , among other things , the classes of shares that you want in your company . The simplest company has just one class of shares common shares but you can be more sophisticated than that and it comes down to really figuring out what is the most tax efficient way to establish your operations .
Speaker 3Now , if you're a young entrepreneur , you're not going to spend a ton of time on this kind of stuff . But there's a lot of life decisions and a lot of things that can go into this . And the reason why I suggest doing the tax planning ahead of time is because it costs you less to do the tax planning at the beginning than it does to crystallize the value of your firm . So say , for instance , you want to change your incorporation later on . It can cost you a lot more to make that change later on than if you figure out what it is that you want to do now . So like , as an example , what am I talking about ? So , for instance , if you want to have employees who have stock options or shares in the company , who have stock options or shares in the company , you might give them another class of shares with different voting rights or no voting rights , as an example . So it's not really that complex or complicated . It actually can get that way , but there are very simple concepts that will drive you to determining whether you want one class of shares or multiple classes of shares , and a good tax person will help you figure that out . Once you've got that figured out , then you go to a lawyer , or the tax person can actually send instructions to a lawyer and say , okay , we want to incorporate this company with these classes of shares , and the lawyer does that . The next thing you need to do is , essentially , you need a bank account , but , most importantly , you've got to get out there to market and sell whatever you're doing . So it's a good idea if you've already had the opportunity to start either developing your product or service and know what it is that you want to sell .
Speaker 3The most important thing that drives every company is sales . You don't have a company really until you have sales , and sales , of course , is going to drive your profits . It's going to drive all of the things that you can invest in , the types of staff that you're going to hire . So my thinking has always been sell . Have a really good understanding as to how you're going to deliver . You don't have to have all of your ducks lined up depending on what you're selling . You might have a good idea and be prepared to deliver when you sell . But sell first and then deliver quickly thereafter and deliver outstanding quality Deliver stuff that is going to make your client absolutely tickled with what they bought , because you're going to need every one of your clients , especially the first ones , to be able to stand up and say you know what ? Ez delivered the most amazing service . We were so happy with what we got from his company . We would happily refer him to anybody else . So those are kind of the steps that you take in starting a company and then it goes on from there .
Speaker 1As he was there at one of those steps , I said I take a backseat , but I'm lying . Was there ?
Speaker 2one of those steps .
Speaker 1Thanks said . I take a backseat , but I'm lying , that doesn't matter . Was there one of those steps ? Thanks , jeff , that was pretty awesome . Was there a step there that was interesting to you ?
Speaker 2Well , first , which step was most interesting to you ? That's a toughie . There were a lot of steps . I think the last one , where you talked about sell first and then deliver to higher than your expectations , was interesting .
Speaker 1Yeah , I think you like to sell , don't you Me ? Yeah , oh , yeah , yeah , you really enjoyed that .
Speaker 2And then of all the steps , what was the most , what seemed like it would be the most challenging to you or would require more work ? Starting the shareholding spots , I guess ?
Speaker 1Yeah , that did seem a little bit complicated . So , like when you have your snow business in the winter , do Jeff and I get to be shareholders ?
Speaker 3If you want , you know the great point , and that is , some of this stuff seems complex , but it's important to remember that you and I say you , any company leader you're not going to be the expert in all these things . You can't be the expert in all these things . You're going to be the expert in the product or service that you're delivering and that you're selling all of these other things that I've just talked about . There are great people out there who you can hire and they will do , they will help you do what you need to do . So really , your job is the leadership and and guiding them and recognizing that they are hired , help . You know you can hire .
Speaker 3There's lots of lawyers out there . There are lots of accountants . There's lots of other business advisors . You can hire tons of different types of people . It's always good to get those types of people by referral , in other words , people who have worked with them before and know the quality of their work , the service levels , their pricing , the value that they deliver . So , but the bottom line is is you don't have to be the expert in , for instance , share structure . That's what you have lawyers and accountants to do . What's important for you is that you get the right solution for the company that you want to build , and that's what they're there to help you to do yeah , that's great advice .
Ignoring Naysayers
Speaker 1I think the good thing is , if ever you wanted to go the entrepreneurial route , we might have a discount on accounting services in the room with us .
Speaker 2That would be useful . So the third , last but not least question what would you have done if not for starting Flexer ?
Speaker 3Suffered terribly .
Speaker 1Blah blah blah .
Speaker 3You know I probably would have continued to look for other business opportunities , but at the end of the day , you know , I probably would have continued to look for other business opportunities . But at the end of the day , you know , you got to put food on the table and so I probably would have continued in a corporate role , doing my best and continuing to sell and make other people rich . I would have done that until I had another good idea to form a business . But you know , what I encourage folks to do is , you know , in your first jobs , look and see , like when you have a client , try and understand where they see gaps in the product or service that you may be delivering . So it's not necessarily your fault . You might be working for a company and the company might provide a set of services . But in talking with a client you come to understand that you know , if we had our druthers , we really wouldn't have the services delivered like this , we would have them delivered like that . And that's what you're listening for . You're listening to your client because often I mean , clients are the best source of that kind of information right , they're the ones who are going to be making the buying decisions . So , if you understand what your client wants , you can then take what it is that you're doing , and perhaps , either within the context of your existing work environment or outside you can . You know , you want to do it properly . When I say properly , you don't want to go in and basically do bad to your current employer . What you want to do , though , is either A you recommend it to your employer on how they can , you know , offer a new product or service or offer it in a different way , or , alternatively , you can form your own company .
Speaker 3You know , there's a gentleman who I've known for you know , most of my life , and he started working in a mutual fund environment , and this guy was very brilliant , and he recognized that clients didn't like the dog food that was being sold to them , and he decided , he recognized that there was a much better way . In this case , because it was mutual funds , it was much more quantitative , there were very great ideas in terms of how he could provide better returns to his customers , and he tried forever and a day to get his management to adopt his way of thinking and to adopt his methodology , and he had very detailed methodology that he had developed , and his current employer basically said yeah , you know what , I'm not so interested . Or in one case , they finally decided , yep , they were going to do this , but then , instead of clients following the methodology that he laid out , clients would use his methodology . But you know , like there's this whole commercial that says but we know the management of our companies we invest in .
Speaker 3And so some of his clients were actually overriding or ignoring the advice that he was giving with what they thought was a better way . And he said you know what ? These guys aren't listening , they aren't taking the methodology that we have , the methodology that we have . If they followed it to the letter or to the number , they would actually do much better . And so , because his current employer really didn't employ what he was coming up with , he decided to form his own company . Make a long story short he's a very wealthy individual today , many years later . He developed his own company , he hired his own staff . He went on to be very successful , and it was by listening to clients coming up with a good idea , listening to clients and being able to go out and sell to them , and he became very successful doing that .
Speaker 1So it sounds like . So persistence and thoughtfulness were kind of keys to your thought process when starting FlexServe . You definitely had to have persistence .
Speaker 3Boy , did I have to have persistence ? You know it's funny because you know , as I mentioned , I grew up through a technical work environment running large projects , environment running large projects . And you know , I finally decided that I was going to sell accounting and HR services Now , the businesses that I ran . I had folks working for me in accounting and folks working for me in HR , but I had never sold accounting or HR services . And I remember telling my father at the time that this is what I was planning to do and my father was very pragmatic and he goes Jeff , how are you going to sell accounting or HR services ? You never sold them before . How are you going to sell them ? That was a great question . And I said to him I said , dad , by this point I've sold about $360 million worth of work . Yes , it's not HR and accounting , but there's 1.4 million other businesses in Canada and every one of them has sold or most of them have sold something . If they figured out how to do it , well , I probably can take the experience that I have and apply it to accounting and HR . Can take the experience that I have and apply it to accounting and HR . And you know , I was glad . It was great that he asked me that question because it gets you to think you know , okay , how are you going to do this and how are you going to do it better than other people out there . So it was a fun challenge . But I think you know that is actually , and I'll segue for a minute . I think you know that is actually and I'll segue for a minute .
Speaker 3If you come up with a good idea , there are going to be naysayers . There's going to be . There are people along the way who will criticize anything and everything you come up with . There are going to be people who say you know , instead of like the , you know , there's some people who will be great enthusiasts and will be very supportive and say that is a fantastic idea . You could get introduced to the old person who goes I'm not so sure . I see the opportunity in that and you can't let yourself get taken out by people who don't know your space .
Speaker 3So you know , you have somebody who's introduced to you and I had people introduced to me as wise old businessmen , you know , and I was supposed to listen to these guys because you know they had made it in their respective fields . But here I was coming up with technology ideas . These guys hadn't the faintest clue . They had never worked in tech , they had no idea what I was talking about , so it was foreign to them , and they were opining and saying , oh , I don't think that's going to work , there's no way . Well , so you know , early in my career , I probably listened to some of these old farts too much , and you know , I probably .
Speaker 3I know that I could have launched other businesses before I did , and part of it was , you know , it's good to seek advice , but you also want to make sure that the people that you're seeking advice from are people who are qualified to give you the advice in the domain that you're actually asking . And you know , some of these folks actually may have been great to give , for instance , financial advice , but not necessarily advice as it related to the product or service that I was suggesting . So I think it's really important not to listen to the naysayers . Uh , and by the same token , though , if you have a good idea , what you want to do is prove it in , and there's ways to prove it in . You can do focus groups , you can do market analysis . There's a whole bunch of ways that you can kind of test the ideas . But you know , I'll give you an example . Where that was tough , so many years ago , there was this thing called a Palm Pilot . Okay , I'm dating myself . There was this thing called a Palm Pilot .
Speaker 1Do you know what that is , essie ? There's one downstairs , we'll show you .
Speaker 3So a Palm Pilot was a device where you could enter contact information , and that was it , so you can enter is it ?
Speaker 2is that that little phone thing that has the pen inside of it ? They show me ?
Speaker 3uh , that is the next , the next generation , and I'll talk about that . This is actually before that , I think . If I know what you're talking about , I think you may be talking about the BlackBerry , but if not , if you're talking about the Palm Pilot , the Palm Pilot , all it had was contacts . It was unusual , like what you have in , for instance , microsoft Contacts
Blackberry Missed Connections
Speaker 3today . It had name , title , address , telephone number , all that kind of information , address , telephone number , all that kind of information . And at the time you had very plain cell phones . They were cell phones , they weren't smartphones , they were just phones with 10 digits , a pound and a star , and that was it , Listeners .
Speaker 1a pound is also now known as a hashtag .
Speaker 3Yes , hashtag . So I had a very good friend of mine at the time who worked for one of Canada's three largest telcos . He was the product manager , so he was the guy who was responsible for this very large telco in determining what would be the next products and services that they offered . So one day I had a eureka moment and I went to him and I said you know , I have this dumb cell phone and I have this Palm Pilot , the cell phone calls numbers . And in those days if you wanted to store 10 numbers in your phone , you actually had to . You know , like . You know , like , on the one or two key was A , a , a , b , b , b . You know you had to dial out , like you know , uh , the , the name of the person and you could store 10 phones phone numbers . And I said to him you know , you got this Palm Pilot where you have all your contact information . You got this dumb phone . Why don't we put it together and develop a device which actually has phone numbers and the capability of making phone calls ? And his response to me at the time was this is the product manager of one of Canada's three largest telcos . He said to me Jeff , you may want that , but our customers don't want that , and I thought you must be kidding me . Now , the thing was is that nobody had come up with the idea , nobody had actually developed a product that did that , so of course there was no market to test it out in . So you could do focus groups . You could go out and say to people so if you had a device that does this and this and this , would you buy it ? And then , if you would buy it , how much would you buy it for ? But here was a guy who was responsible for forward thinking and he was not forward thinking . Of course . Soon thereafter came along this little company called RIM Research in Motion that developed the BlackBerry , which is now long since defunct , but BlackBerry for a while they had the largest customers in the world . They had the presidents of the United States and every other country using their devices . They came along . Yeah , listen , if only it was me who'd formed that company .
Speaker 3But my point here is don't let the naysayers take down a great idea . Right , and here this guy was supposed to be an expert in his domain . He was , he knew the market , but he was still a naysayer . And the the idea is is if you have a great idea that you think has merit , objectively convince yourself , yes or no , whether this is going to be successful , and get good advice from people , a whole bunch of people who know that type of market , your product or service is going to be new . But if you get lots of input from other people and of course you want to do it protecting your intellectual property , et cetera but the point is that if you have a great idea and are confident that this is a winner , keep going with it . Don't let the naysayers get you down , don't let people put hurdles in front of you . Keep jumping over those hurdles and you , you can be a star , you can be unicorn .
Speaker 2Yeah , I actually remember when you told me that story , uh , about the uh guy who you gave the idea of the blackberry .
Speaker 1Yeah , did you learn anything from all of that , uh ?
Speaker 2yeah , uh , of the Blackberry . Yeah , did you learn anything from all of that ? Yeah , like you said , don't let the naysayers get you down . Entrepreneurship requires a lot of perseverance and it requires a lot of guts or fire in the belly Chutzpah .
Speaker 1Yeah , it requires all of that . Well , I think , even if your career is not going to be in entrepreneurship , there's definitely a lot of great lessons that you can take away from that . What do you think ?
Speaker 2Yeah , for sure , and it was a great conversation .
Speaker 1I really loved listening to you , jeff , share your story in this way . I haven't been able to hear it in this way before , so it was really awesome to hear , and I think our listeners will probably enjoy it as well . So thank you for taking time to record season two , episode one , with us .
Speaker 3It was an absolute delight ,
Final Thoughts & Wrap Up
Speaker 3and if there's any questions that any of your listeners have , I'd be happy to answer them .
Speaker 2Yeah , for sure , we'll see if anybody dms the instagram . So join us on the next time . Uh , for more hoops and crumbs on apple podcast , spotify , amazon music and anywhere else you can find your favorite podcasts . We'll talk basketball cookies and share other random life musings . Uh , if you have any questions , dm us at hoopsandcrumbs IG . We'll be sure to add them in future chats .
Speaker 1Thank , you Goodbye , ciao , bye .