3. Resilience, Exits, and Venture Capital: Jackie Dinsmore's Entrepreneurial Odyssey
EPISODE 3
Did you know that mature entrepreneurs bring a wealth of diverse experiences to the table? In this episode of Figure Eight, Jackie Dinsmore highlights the value of founders with life experience. Jackie and Julie also discuss how letting go of the helm to become an employee and eventually selling one's ownership requires adaptability and emotional preparedness. Her story provides invaluable lessons on the often-overlooked human side of business transactions.
Catch the Conversation
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Jacqueline Dinsmore was a corporate lawyer at Blakes in Toronto, and subsequently worked as Assistant General Counsel at The Toronto Star. Originally intended as a side project to satisfy her non-legal creative side, Jacqueline launched FlapJackKids, a company that focuses on all reversible products for women and children.
Jacqueline's products were featured in swag bags for Emmys and Oscars pre-parties, and can be found in thousands of stores in North America and worldwide. She has been named Top Mompreneur by Mompreneur Magazine and appeared in Forbes Magazine alongside Hilary Clinton and Barack Obama. Her company was featured numerous times in top press and media including The Toronto Star, The Globe and Mail, Ok Weekly, Us Weekly, Woman's World, USA Today, The Huffington Post and Woman's Day.
Jacqueline was also one of the original owners of Caravel Law and since its sale, now acts as its Co-Managing Partner. Caravel Law is a revolutionary law firm of over 100 lawyers that has disrupted the legal services industry in Canada, by making big firm trained and in-house experienced lawyers available as fractional counsel to start-ups, F500 companies and everything in between. Its low overhead model ensures access to great lawyers at a reasonable cost.
Jacqueline has had three successful exits and most recently started Extra Innings Ventures, a venture capital firm focusing on under-represented founders with life experience.
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Julie Ellis (00:00:04) - Welcome to Figure Eight, where we feature inspiring stories of women entrepreneurs who have grown their businesses to seven and eight figures revenue. If you're in the mix of growing a bigger business, these stories are for you. Join us as we explore where the tough spots are, how to overcome them, and how to prepare yourself for the next portion of the climb. I'm your host, Julie Ellis. I'm an author, entrepreneur, and a growth in leadership coach who co-founded, grew, and exited an eight figure business. This led me to exploring why some women achieve great things, and that led to my book, Big Gorgeous Goals. Let's explore the systems, processes and people that help us grow our businesses to new heights. If you're interested in growing your business, this podcast will help. Now let's get going.
Julie Ellis - Hello, and thank you for joining us for another episode of figure eight, a podcast for women entrepreneurs who are growing businesses from seven figures to eight figures. And today I'm in conversation with Jackie Dinsmore, a very dear friend of mine and somebody that I met in the entrepreneurial trenches.
Julie Ellis (00:01:24) - And Jackie is a serial entrepreneur. She has founded many companies. She has multiple exits from those companies, and she is currently working in one of them, as well as founded a um venture capital company called Extra Innings Ventures. And I'm very curious to hear about that as we talk today. So welcome, Jackie.
Jackie Dinsmore (00:01:49) - Thanks so much, Julie. Really, uh, really excited to be on the podcast and I appreciate the opportunity.
Julie Ellis (00:01:56) - Thank you. Well, thanks for joining me. I really appreciate it. And I'm so excited for you to tell your story today. Um, because of course, we've grown up together in this entrepreneurial journey. And we met when you had a children's product business, which was not your first business, um, but was, um, growing at around the same time Mabel's labels was growing. And so we met through some entrepreneurial circles that way. So tell me a little bit about your journey and the companies you've founded and how you came to do what you've done.
Jackie Dinsmore (00:02:28) - Sure. Yeah. For sure. Uh, so I guess you could call myself a recovering lawyer. Um, I worked at, uh, so I went to law school at Western. Thought I was going to save the world and work for World Vision or some kind of charity in the legal world. Um, didn't really want to do corporate. And Blake's a big, uh, traditional Bay Street law firm. Came knocking, uh, for summer student jobs. And my dad at the time said, you better just go interview, because when they come knocking, you go interview. And I'm like, okay, but that's not really what I want to do. And they ended up selecting me for their summer student program. And I thought, okay, well, I'm just gonna do it for a little bit of time and, uh, ended up spending several years there, um, which actually, in retrospect, was a really, really good foundation for my legal career. I learned a lot as a corporate securities lawyer.
Jackie Dinsmore (00:03:20) - Um, but, you know, billing 2200 hours a year. It was really tough, um, really, really close to my mom. She ended up getting, uh, diagnosed with stage three breast cancer. And I thought to myself, in that moment, am I going to be sitting here at this desk till like, 3:00 in the morning and my mom's going to die of this disease, and I will never forgive myself? So a job came up at Torstar, a parent company of the Toronto Star. It was four days a week, which was unheard of in our profession. And, uh, I was very fortunate. Somehow I got that job. The general counsel and I bonded over dogs. Um, I think there was, you know, 170 people that applied for that job because the legal industry just didn't have four day a week positions. But what that enabled me to do in getting that job was I could take my mum to chemo on the fifth day. Um, and I ended up staying there for eight years.
Jackie Dinsmore (00:04:10) - But during that journey, my mom had survived breast cancer and she said, I think we should start a business together. Um, had this booming law practice. Um, and I was on maternity leave at the time, and I kind of looked at my mom and I'm like, are you kidding me? Like, we're going to start a business. I have this newborn. I'm supposed to go back after my maternity leave, and you want to start a brand new business. So of course I was like, okay, why not? Um, and what she had done was she had actually put six handbags in her suitcase and she wanted to start a convertible handbag business. So we cobbled together a prototype. We ended up winning the top ten best Products award in North America, which got us into Emmy, um, pre-party swag bags and Oscar pre-party swag bags, which you kind of know all about with Mabel's Labels. And it really kind of launched from there. People love the product, and I really love the world of entrepreneurship, to be honest with you, as as a trained lawyer and someone who never took an entrepreneur course in my life, this was just a really new and exciting adventure for me.
Jackie Dinsmore (00:05:12) - And I really felt like all of a sudden a big light bulb went on that I'd found my calling. So we ended up in about 250 stores, and I had to tell the general counsel at Torstar at the time that I had to quit my job as a lawyer, which was crazy, because my mom basically said, we're either going to shut the company down or you can go back and do law, or we got to make a run at this, which means that you got to quit your job and do this full time. So we did that for a few years. It went well. But the handbag business is really competitive. So you can imagine, right. You're competing with the Louis Vuitton and the Kate Spade's. And there's a lot of capital that goes into that type of business. So we pivoted um, and actually took that reversible convertible concept and started a company called FlapJackKids. Um, I had gone to a parenting class, and in the parenting class now, my children were a little bit older.
Jackie Dinsmore (00:06:03) - They said, uh, don't ask your child to wear a jacket. Say, would you like to wear the red jacket or the blue jacket? Empower them with choice. And so, um, that's what FlapJackKids essentially was, was empowering kids with choice through a whole reversal line of reversible apparel. Do you want to be the lion or the monkey? Do you want to be the frog or the bear? And one of our best selling products, which could could be found in 5000 stores now, is one of our reversible sun hat products. So there I am. I'm in a full fledged I'm a full fledged entrepreneur, um, loving it. And my second business. And that actually also led to my first exit, which happened in 2019 just prior to Covid. Um, my third and fourth businesses and we can get into this later, uh, ended up kind of as an offshoot of that. Now, I realized I could be an entrepreneur, but I could also fix the legal industry, which I came from.
Jackie Dinsmore (00:07:00) - And, uh, as an entrepreneur, I got really frustrated with lawyers. I actually hated them and, uh, and really found a business that solved that problem so I could combine and marry my, my legal industry knowledge with my entrepreneurial kind of skill set that I now acquired. So that's my journey.
Julie Ellis (00:07:19) - That's really eclectic and interesting.
Jackie Dinsmore (00:07:23) - Thank you. Yeah. It's, uh, as they say, success doesn't look like this, right? It kind of looks like this. And my journey was, you know, definitely not the the road well traveled. Let's put it that way.
Julie Ellis (00:07:35) - Yeah. It doesn't always look like a staircase, a neat and tidy staircase that you just climb. Definitely. The pot of spaghetti is, uh, it feels like the pot of spaghetti, even if to the outside world, it looks like you've got it all together.
Jackie Dinsmore (00:07:50) - Exactly, exactly. Pressure.
Julie Ellis (00:07:52) - Yeah, yeah, well, that's interesting. And so why did you feel like your third and fourth businesses? You know what? What made you feel like the ingredients were right for disruption in the legal field?
Jackie Dinsmore (00:08:06) - Well, I kind of come to this conclusion because as an in-house lawyer at Torstar, we used external counsel at the time, and I just I just got really frustrated with them.
Jackie Dinsmore (00:08:16) - I mean, three lawyers on a phone call, $1,200 an hour, lawyer's not calling me back. So automatically the entrepreneurial mind kind of goes, well, wait a second. There's better ways of doing this. I don't care that this has been done this way for 200 years. Um, and so I kind of stumbled on my third opportunity. I didn't found that one initially. It was started by two guys, fabulous partners of mine, Joe and Robson. I had approached them and wanted to be involved in some way, and, uh, they weren't quite ready to have me join as an owner. And I said, come on, guys, you need some estrogen. Let me join as an owner. What can I do? And it took a little bit of time. It took about, uh, a couple of years of me showing them that I really believed in the model and I really believed in, in what they were doing and so bought in in 2014, which then led to our first exit in 2016.
Julie Ellis (00:09:10) - And so that must have been an exciting time.
Jackie Dinsmore (00:09:12) - It was. We were only at about, I'd say 12 lawyers at that point. Um, and we grew that, sold it, and now we've grown it again and right about 110 lawyers. So it's, it's had some different iterations. But, you know, I think that was needed in order to kind of figure out our journey. Um, and just being able to tackle an industry that really needed disrupting, we have to look at these industries that have been around for so long and say to ourselves, they don't always have to be done that way. There's better ways of doing it right.
Julie Ellis (00:09:43) - And so what were some of the better ways that you were working on it with the law firm?
Jackie Dinsmore (00:09:48) - It doesn't always have to be about cost. Um, it can really be about like when you're thinking about cost people. I don't want it to be a race to the bottom. So when you hire a contractor, for example, um, a contractor doesn't necessarily you don't necessarily want to hire a contractor that's the most expensive and you don't want to hire a contractor the cheapest.
Jackie Dinsmore (00:10:05) - Right? So Caravel kind of is that middle of the middle of the road, which is which is, I think, where you want to be. We felt that we wanted to bring on Bay Street lawyers who were trained and had that pedigree, but we also wanted lawyers that had that in-house counsel experience. So that practical, kind of business minded, they've either had to run businesses themselves or own businesses themselves, or they've worked in businesses. You become a very different lawyer. As I found out personally, when you've been an entrepreneur or when you've worked in a business, because it's not about, you know, just saying no, it's not being the sales prevention team, it's being more practical and business minded. So we wanted to disrupt it in that way. The other way we really wanted to disrupt it was embracing technology. It's crazy to me that some of the big large firms don't embrace technology. They see it as evil. They see AI as replacing the lawyers and the bodies. I see it as an amazing tool in our toolbox.
Jackie Dinsmore (00:11:05) - So at our firm we have a director of legal innovation, and it's her primary job is to find tools, a technology that can make our jobs more effective, more efficient and better. So we use those all the time. So we're we're very innovative in that way, not only in terms of the lawyers that we hire, the pricing, but also the technology we use.
Julie Ellis (00:11:27) - Yeah, yeah. And I think one of the things that today feels, uh, very common, but wasn't common when you really started doing this was the lack of, you know, everybody going to the office every day that a lot of your team works from home and that your physical office space is actually very small.
Jackie Dinsmore (00:11:46) - It is. Our head office staff works there. That was our way of reducing overhead. So, you know, we don't have the mahogany panel boardrooms and the fancy artwork and the stogies and the corporate jets. I take my clients to Swiss Chalet. We don't go to Canoe. Sorry, guys. Um, but clients don't care about that anymore.
Jackie Dinsmore (00:12:02) - 200 years ago, even, like 20 years ago, maybe they did, right. They wanted to go to the fanciest restaurants and go to the best golf courses. But in in interviewing our clients, we said, what do you really care about? They're like, we don't care about that. We don't need to go to the Leafs games and the Raptors games. We'd much rather see a more reasonable invoice that gets us from A to B, and so we want to put more money into our, you know, clients pockets. That's that's our goal. And I think we're really seeing some traction as a result of that.
Julie Ellis (00:12:30) - So now I know that the first time, uh, when you were able to have an exit with the law firm, you ended up as an employee.
Jackie Dinsmore (00:12:37) - Yeah.
Julie Ellis (00:12:38) - So what can you tell me about that?
Jackie Dinsmore (00:12:42) - Well, it's been a bit of a journey because I kind of started off as an employee and then became an owner and then, like, ended up. Now I'm not an owner at all.
Jackie Dinsmore (00:12:49) - I've sold everything, um, and, and for the longest time, I at least had something. And now I do not have any of that. Um, a good friend of ours, Kelsey Ramsden, wrote a book called The Success Hangover. Right. And I highly encourage people to read it. Um, and even just that title probably explains how a lot of owners who have had exits feel. Right. It's it's not about the check. And my mom said it best. She's 75 and we we got a we got a nice check for FlapJackKids when we sold in 2019. And we had a big steak dinner. And I remember we were so excited. But not long after that I saw some sadness on my mom's face. Right? Like, it's not always about the money, it's about the sense of purpose. It's about being able to go into the office every day and feeling like you're part of a community, that you're an entrepreneur, that you're building something. And so I think you have to be really, really careful about about that outcome.
Jackie Dinsmore (00:13:41) - I'm very, very fortunate because we partnered with the VC firm, um, out of the US, who said to us right out of the gate, listen, we bought you because we really believed in what you were doing, and we love what you're doing. So just keep doing it. We're not coming in and changing everything and changing all the people and changing the processes and the systems, and we bought you because you're successful and you're growing. And if you stop growing and your numbers don't look good, then maybe we might make some changes. But as long as things keep going in the right direction, why would we change a thing?
Julie Ellis (00:14:12) - Yeah, which is great. What a great partner.
Jackie Dinsmore (00:14:16) - Right. So to those listening, you know, when you're looking to have somebody buy, you don't just look at the numbers on the check, look at who that is and what they expect of you and what they expect of the company. That's almost more important. And I would actually take less money to partner with the right partner, then take more money and not not be with the right partner.
Jackie Dinsmore (00:14:37) - Now, if you if you don't have any involvement with the company, then take the biggest check you can, I guess. But, um, I think it's really important to partner with the right person.
Julie Ellis (00:14:45) - No, I think your mom's experience is really common. Also, that there is a mourning period of, you know, in the after, especially when the sale means that you do leave the business. And so that's a huge change for people who feel very attached to their, you know, babies. We don't like killing our darlings.
Jackie Dinsmore (00:15:06) - Right. And especially when they sign very comprehensive non-compete or whatever. And your hands are tied to do anything similar. You know, you feel kind of like a floating ship lost out to sea, right. Um, so I think a lot of entrepreneurs should really think about that before they go down that path. And I've been very fortunate with all of my exits to partner with the right people.
Julie Ellis (00:15:30) - Yes. Yeah. And you've managed to sort of piece things together. And so although you say now you're you own nothing, you do have a very exciting venture that you have begun.
Jackie Dinsmore (00:15:41) - I have.
Julie Ellis (00:15:42) - You want to tell me a little bit about that?
Jackie Dinsmore (00:15:44) - Sure. So through the journey of FlapjackKids and Cognition and Caravel um, more so on the consumer product side with FlapJackKids and Lovely. I was trying to raise money. I didn't try very hard at it, but when I did try, I remember I went down to Michigan and I did this big presentation to a bunch of angel investors and scared as all get out, right? Um, I knew everything about my business, but still nerve wracking. And I remember getting like a few sideways glances. Not only because I was a consumer products company, and consumer products companies tend to have a hard time raising capital. But, you know, I had had a couple of kids at that point. I was a little bit older, and I found that a lot of VC firms and angel investors, they a lot of them just seemed to really be looking for the next Mark Zuckerberg.
Jackie Dinsmore (00:16:33) - Right. They wanted that 20 year old kid, college kid, right, straight out of college with the idea. And there's a disproportionate amount of money that goes to those kids, right. And I'm not saying it's. I'm not saying it shouldn't I? I'm by no means saying that. That people that that really smart college kids that are starting their entrepreneurial journey shouldn't get money. But there's a huge sector of the population that are actually overlooked. And that's those are entrepreneurs with life experience. So, you know, I say mature founders, it doesn't necessarily have to we don't have to settle on an age. But people that have had a lifetime experience, perhaps in the industry in which they're starting their venture. Um, so I started a VC firm with two of my colleagues called Extra Innings Ventures. So if you're a baseball fan, you get the concept of extra innings. And we're focusing on investing in founders who are in their extra innings. These are people that have played the game, you know, and now this is where the rubber meets the road.
Jackie Dinsmore (00:17:32) - This is where it's really important for them to succeed. They don't have time or the runway to waste money and time.
Julie Ellis (00:17:41) - Right. And they bring a lot of like worldly experience in terms of what they've already done to the idea of building another business.
Jackie Dinsmore (00:17:50) - Exactly. And it's been really interesting when I kind of started to look into some of the studies, most recently, there was a study in the Journal of American Economic Review which said that a 60 year old who starts a new business has a three times more likely chance of succeeding in that business than a 30 year old peer, which is kind of incredible. Right. Um, and you'll see different ages in different studies. I've seen, you know, comparing to 50 year olds or 45 year olds. And not to say that, you know, I'm not looking to invest in somebody who's younger, but I want somebody to have had that experience. And so, um, we're starting a small fund, $5 million fund, um, investing in founders with life experience with, uh, an additional focus on underrepresented founders, which include women, you know, BIPOC members or the LGBTQ community.
Jackie Dinsmore (00:18:43) - So it's it's really exciting because we're kind of fishing in ponds that other VC firms aren't fishing in. It's not like we're anti the younger entrepreneur. We're just over here doing something a little bit differently. And as a result, we're seeing opportunities that other VC firms don't get to get to see. So that's been really, really exciting. And uh, and it's incredible to when somebody has had, you know, 15 years of experience in an industry and they start a business in it, of course, they're going to know a lot more about that than somebody who's never been in that industry. And I think I actually found that with the legal industry, it really helped that I had had that legal journey before embarking on trying to disrupt it.
Julie Ellis (00:19:23) - Yeah. Yes. Because you come in with some context and an idea of how things work that's, you know, rooted in experience.
Jackie Dinsmore (00:19:31) - Exactly, exactly like I'm there's no way I'm going to start an engineering firm anytime soon. And I shouldn't because I know nothing about that.
Jackie Dinsmore (00:19:39) - But boy, would I would I back an engineer who wants to disrupt that industry, right? Right.
Julie Ellis (00:19:44) - Yes, definitely. That amount of expertise is really the foundation of what it is you're looking for.
Jackie Dinsmore (00:19:52) - Exactly, exactly. So yeah, we're just at the starting, um, you know, the start of that, uh, like I said, we're raising funds right now and, um, and looking to deploy capital probably in the next six months. So it's pretty exciting. Um, we're going to invest in about 10 to 12 different companies, and we're somewhat industry agnostic, which actually is a homage or a play back to the fact that as a consumer products company entrepreneur as you could relate to, Julie, I think those companies need investors too. And there's so many folks that are terrified of investing in inventory heavy based businesses. But I think I think there's a lot of potential in that space that is that is lost and missed when people are only focusing on technology. For example.
Julie Ellis (00:20:36) - If you were going to start another product based business now, what would you what lessons, you know, do you learn out of that business? Those product businesses that would carry you forward?
Jackie Dinsmore (00:20:50) - Well, you know, I mean, hindsight's 2020 and I made lots of mistakes in that business.
Jackie Dinsmore (00:20:56) - I think I got so excited about the product that I often over ordered. Um, and, you know, I think if you can keep your SKUs to a minimum, I see a lot of consumer products companies that just get too excited about, well, we should add that size and that color and this style and that style. And next thing you know, you've got 350 SKUs and that's really hard to manage. Right. So I think that's one lesson that I've learned from the consumer product world is don't get too excited and overbuy.
Julie Ellis (00:21:25) - Yeah. And I think that's a really interesting point, because in a company that's more on the fashion side, like FlapjackKids was you are looking at, you know, sizes, colors and it can multiply upward and outward really quickly. Yeah.
Jackie Dinsmore (00:21:42) - I mean, the one fortunate thing we had about being a kids company is lions and monkeys and frogs and bears don't go out of style. Right.
Julie Ellis (00:21:49) - But absolutely.
Jackie Dinsmore (00:21:50) - But if you are a women's fashion brand, all of a sudden, oh, that's not the color of the season, right.
Jackie Dinsmore (00:21:57) - And so you got to be really careful. And that's part of the reason why we kind of pivoted away from from lovely the handbag business. Because that if you can't if you're not fashion intensive in handbags then I don't know what is. Right. And so, um, it was really the right move for us because we, we basically mitigated some risk there.
Julie Ellis (00:22:17) - Um, I think also when you're manufacturing overseas, you're afraid to under order because getting more product if you sell through to is really time, you know, takes a long time and, you know, and then you lose your opportunities. And so you you kind of have a predisposition to that over ordering.
Jackie Dinsmore (00:22:36) - Yeah. And I remember my business professor at Queens, a guy named Frank Cullum, he's he's no longer with us, but amazing, amazing professor. And he always said that selling out is actually a really bad thing, because if you have too much inventory, you can always sell it at a discount. But if you don't have inventory to sell you, you don't make a sale.
Jackie Dinsmore (00:22:57) - And so I think that always played in the back of my head. And not to say he's wrong, he's absolutely right. But there's always extremes, right. And so when you over order and you have too much inventory and we've seen it with a lot of entrepreneurs in this business, they've got warehouses packed of stuff. And there's this misperception that you can sell it to HomeSense or Winners. They're they're a lot pickier than they used to be. And so it's not easy to offload products. So you just got to be really careful. And that's why investing in the right CPG companies is is something you gotta, you gotta really nail down in the due diligence phase.
Julie Ellis (00:23:30) - Yeah. Yes that's true. And and so that'll be a consideration for you in the next few months hopefully. Yeah. Exciting. Yeah. Yeah I'm always excited about product businesses though. And and a little bit I think I have a soft spot because of being a product girlie myself, but also because I think that they have a hard time like the, the, the landscape for investment is not as, as, as deep.
Julie Ellis (00:23:56) - And they do need capital because they need working capital for investment. And you know, there are a lot of hard problems that they are trying to solve.
Jackie Dinsmore (00:24:05) - Yeah. No. Exactly, exactly. And I mean, we're always gonna wear shoes and clothes and I hope that's not going away. Uh, and as long as that's still, you know, a need, then I think it's a business that's needed as well.
Julie Ellis (00:24:19) - Okay, so if you were thinking about building a founding team again, what are the things you learned about that that you would want somebody else to know?
Jackie Dinsmore (00:24:29) - Well, it's funny because with Lovely and FlapJackKids, the founding team was my family. And that's like the number one faux pas, right? You're not supposed to ever, ever start a team with family or friends. Um, and I wouldn't necessarily say I wouldn't do that again. I mean, I think you have to find the right family members and the right friends. The nice thing about doing a business with my parents and my husband is my mom and dad really worked quite okay, taking kind of a backseat in very specific roles and doing their roles and staying in their lane.
Jackie Dinsmore (00:25:04) - Right. And then I kind of had a very specific role. Working with my husband was really hard. And he'll say this, he's more of a corporate guy. And, you know, he didn't like it when meetings ran over. He's less entrepreneurial. And so immediately, almost within like six months of starting the business, I was like, well, he's not the right team member for me. And thankfully he became a bit of a silent partner and he was more than happy to do that. And then there's been situations over the years where I've I've thought about starting companies with friends and they're all like super intelligent, creative, successful people. But you almost need like, not too many people in this with the same kind of skill set and the same kind of personality. You need different people in different roles. Um, Bill Gates is always said right, like that. He started Microsoft not just because of him, but he surrounded himself with people that could do things that he couldn't do that had different skill sets and different abilities.
Jackie Dinsmore (00:26:05) - And I always say, you know, if you work really hard on your weaknesses, all you have is really strong weakness. Like, recognize that and put your ego aside, that you can't do everything and you shouldn't do everything right. And so find the people that can do the things you can't do and assemble the team on that basis, and then delegate and be comfortable with it and be okay with it.
Julie Ellis (00:26:29) - Yeah. And it is one of the things, like about scaling up that some entrepreneurs find hard, is it that it has to get repetitive and it has to get specific. And you know, it's not about, you know, chase the, you know, shiny objects all the time. And that can be a very difficult transition in the scale up phase. Exactly. Yeah.
Jackie Dinsmore (00:26:51) - Exactly. I mean, life's motto. And if you live by this, I think it really works. And it's kind of always kind of do something in moderation. I think you don't want to be chasing the shiny thing all the time, but you also don't want to get stagnant.
Jackie Dinsmore (00:27:04) - Like one of my most favorite phrases is like, the rolling stone gathers no moss, right? You stay stagnant and you're like, well, we've always sold the red widgets, and they do really well. You keep selling red widgets for 20 years. People get tired of that and the flame goes out. So you do have to always innovate. But to your point, Jules, like you can innovate all the time, to the point that you know your costs are way too high and now you don't have anything that really is is good enough to sell.
Julie Ellis (00:27:29) - Yeah, yeah, it's about finding that like those sort of processes and procedures that get you stepping along, you know, without becoming stagnant and without too much chasing. You know, there's that middle happy spot.
Jackie Dinsmore (00:27:44) - Exactly. Yeah, exactly.
Julie Ellis (00:27:47) - Um, so what parts for you of growing a business have you found to be the most challenging people?
Jackie Dinsmore (00:27:56) - Another good friend of ours will always say the world should just be run by robots. Forget these humans.
Jackie Dinsmore (00:28:01) - Like it's hard. Um, people are really tough, you know, and they have emotions and personalities and needs and wants and desires and finding how that all fits within your plan is really hard. But if you find the right people, like wow, wow. And I think some of the most successful companies I know have the best people.
Julie Ellis (00:28:23) - Yes. And I think it is one of those things of like, you know, if I'm going to ask entrepreneurs to make a. List of things they never imagined doing when they founded a business. Managing people will come up on that list quite often.
Jackie Dinsmore (00:28:37) - Yeah, it's very, very hard. Right. And, um, and I think a lot of entrepreneurs tend to have big egos. I think that's the and being able to put your ego aside and letting someone else take the credit for things is really hard for people. Right. Um, and I'm not saying that, you know, that all entrepreneurs are narcissists by any stretch, but, um, you know, they get so excited about their dream and following that dream.
Jackie Dinsmore (00:29:03) - And if the if you just go off a beaten path a little bit, it gets scary for some entrepreneurs. But sometimes that beaten path is is exactly the journey to success. And they have to kind of believe in their people. Right. Um, and let them do their job well.
Julie Ellis (00:29:19) - And I think about I wrote in my book about how, like, no one actually ever sits you down and says, here's how to delegate effectively, here's how to let go, here's how to explain, instruct and create. Um, you know, a pathway where when it comes back to you, complete, you're going to get what you want. Nobody ever teaches you that. And so a lot of times, you know, of course, we end up winging it. And that's, you know, often not successful or it gets you to a certain point, but it can't get you everywhere that you need to go.
Jackie Dinsmore (00:29:53) - Exactly, exactly.
Julie Ellis (00:29:55) - Yeah. So what are some of your best lessons that you've learned on this journey? And what what do you think everybody needs to know?
Jackie Dinsmore (00:30:03) - Well, um, I'll read you a quote. I have my most favorite, favorite quote. Can I read you my quote? And this kind of goes to the idea that actually I do want to go to Africa in a year or so. So the idea of being able to focus on your business but also take time away, um, this actually talks a little bit about Africa, which is kind of exciting. So every morning in Africa, a gazelle wakes up. It knows it must run faster than the fastest lion or it will be killed. Every morning a lion wakes up. It knows it must outrun the slowest gazelle, or it will starve to death. Doesn't matter whether you're a lion or a gazelle. When the sun comes up, you better be running. And what I love about this quote, right? Is it? And there's so many different meanings in this quote, but let's say the gazelle is the brand new business, right? Like you're you're fairly weak. You know, you don't have a lot of revenues. You don't have a lot.
Jackie Dinsmore (00:30:54) - You gotta keep moving. You gotta keep innovating, gotta keep going. Maybe the lion is the super successful business, right? You're 15 years in your $20 million. You can't stop. It's not like you've made it. Okay, this is great. I'm done. I'm hands off. Right. You gotta keep going. And this kind of goes back to my point about. I think you always have to keep innovating. You can't get you can't get stagnant. You got to keep running every morning. You got to get up. You got to think about how do I propel my business forward? How do I make it better? How do I make it more effective? How do I make it more efficient? Even if what's working for you now is working for you, it might not work for you tomorrow. Um, and everyone knows this Wayne Gretzky quote about how he always, um, skates where the puck is going to be, not where it's been, I love that.
Julie Ellis (00:31:47) - There's too many.
Jackie Dinsmore (00:31:48) - People look behind and you gotta look forward.
Julie Ellis (00:31:51) - Yeah. Well, and I think, you know, it's a pretty accurate to me. Representation of entrepreneurship is trying to figure out where the puck is going and to be there. And, you know, the idea that it is a constant cycle of learning, entrepreneurship. Like if you're ever sitting at whatever little pinnacle you think you're at and you're like, I think I've got this. Like tomorrow it's all going to come crashing down on your head and you're going to be like, oh, I actually have no idea what I'm doing again. And so, you know, I think and this is, you know, I think a question for you too, about how you put the community around you that help has helped you navigate all the things through all the businesses that you have co-founded, um, to, you know, keep climbing basically.
Jackie Dinsmore (00:32:42) - Well, I've had a coach for a number of years, and what I love about her, she doesn't only coach me on my professional life, she coaches me on my personal life, my spiritual life, my physical life.
Jackie Dinsmore (00:32:51) - All those components have to come together towards success, right? If you have a great company and things are going really well, but your personal life is falling apart, guess what? Guess what? It influences, right? Influences your professional life and vice versa. You know, if you've got a great marriage but your business is failing, sometimes that will influence you. Know your life at home, with your kids and with your spouse. So I think surrounding yourself like getting a really, really great coach. And I don't have to convince you on this, Julie, you're an amazing coach, but getting a really good coach to be that support is key. And then just what we have right through our friendships and through spending time with women and men and other people who are going through the same journey. Um, I have some really great friends from high school. They're all teachers, and I love them and adore them, but they look at me like I have three heads half the time because they don't understand some of the entrepreneurial, you know, highs and lows that I've gone through, right? They've got different highs and lows.
Jackie Dinsmore (00:33:52) - Not to knock teaching, but it's a very, very different profession. So surrounding yourself with people that that get you is so important.
Julie Ellis (00:34:02) - Yeah. Good. Well, thank you so much for joining me. I am so glad that you're one of the people that I've surrounded myself with on this journey. Um, and I thank you very much for talking with me today, and I'm going to be very excited to follow the path and trajectory of Extra Innings Ventures and the companies that you invest in, and see what happens for you next.
Jackie Dinsmore (00:34:25) - Thanks so much, Julie. Really appreciate your support and the opportunity. And good luck with the podcast.
Julie Ellis (00:34:30) - Thank you. Take care. I hope you enjoyed today's episode. Please remember to hit subscribe on your favorite podcast platform. So you won't miss any episodes. Figure eight isn't just a podcast, it's a way of seeing the big, gorgeous goals of women entrepreneurs coming to life. If you're interested in learning more, you can find my book, Big Gorgeous Goals on Amazon anywhere you might live.
Julie Ellis (00:35:02) - For more about my growth and leadership training programs, visit www.julieellis.ca to see how we might work together. Read my blog or sign up to get your free diagnostic. Are you ready for growth? Once again. That's julieellis.ca. When we work together, we all win. See you again soon for another episode of Figure Eight.