March 23, 2021

Episode 23: 3 Lessons I've Learned as a 2nd Generation Entrepreneur

Episode 23: 3 Lessons I've Learned as a 2nd Generation Entrepreneur

I think we all can agree we learn a lot from our parents, for better or for worse. And growing up with an entrepreneur father, I learned a lot about life AND business that I still take with me to this day.

I think we all can agree we learn a lot from our parents, for better or for worse.

And growing up with an entrepreneur father, I learned a lot about life AND business that I still take with me to this day.

On today’s episode, I am sharing the 3 biggest lessons I learned from being a second generation entrepreneur, and how they have made an impact on my business today.



  • How I was taught to look at opportunities
  • What happened when I confronted my dad about my childhood
  • The secret he taught me about time that I will never forget
  • The reason I have a koi fish tattoo (which he hates, btw)


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Growing up with an entrepreneur for a dad, I had a unique start into entrepreneurship. On today's episode, I am sharing the three biggest lessons I learned as a second generation entrepreneur, and how that has influenced my business. Stay tuned.

I'm just after launching dozens of courses and generating multiple six figures in Revenue Online, I have learned the right and wrong way to launch an online course. And in the last two years, I have helped my friends and clients generate more revenue with less stress using my aligned Launch Formula. On this podcast, I'm sharing with you my simple strategies and systems so you can make more money online and make a bigger impact on the world. Keep listening for the launch fix podcast.

Hello, hello, and welcome back to the launch fix podcast. I'm so excited that you are here. And listening this week. And I have an episode for you today that I'm actually really excited to share, I'll be honest with you, vulnerability is not a strong suit of mine. But after talking with some other entrepreneur, friends of mine, I realized that I have never really shared how I got into entrepreneurship. And my journey to entrepreneurship has maybe been different from yours, or maybe it's quite similar. But I do think that there's value in learning a little bit more about me as a business owner, and as a person and kind of how I got started and all of this. I come from a family of entrepreneurs, actually, my dad is an entrepreneur, my uncle has a successful business as well. My aunt, my dad's sister has started many, many businesses. And I really feel like this is something that I was meant to do, like I was born to do. And it was something that has been in my blood since I was a kid, which is really funny, because my sister is not entrepreneurial at all. I love her to death.

She's amazing. But she does not have an entrepreneurial bone in her body. And neither does my husband. And so it really makes me wonder on like a person to person standpoint, if entrepreneurship is not necessarily learned, but more inherent, right? If we're born with the gene of entrepreneurship. And this, I could go on about that for a long time. But I know a lot of entrepreneurs who have entrepreneurial parents, or they grew up with that, but I also know plenty who don't. And so it's really an interesting idea of how we all are brought up in different ways and how the things that we experience as kids influence us far into adulthood. I was not the kid who is telling you like I had a lemonade stand at five and then made $100,000 in high school like that is not my story. But I was always looking for opportunity.

I saw my dad building businesses from a very young age, I do remember when I was really little, he did have a job. But he always kind of had non conventional jobs. And he was always building some kind of business on the side. And so I saw firsthand what it took to build a business, how to build a successful business, how not to build a business. And I learned a lot of things along the way. And so after, like talking a lot with my dad about the subject, he and I are very close, which I'm so grateful for. I thought it would be fun to share a little bit of the lessons that I've learned as a second generation entrepreneur, and how those things have really influenced my business. So the first thing that I have learned about entrepreneurship, is that to an entrepreneur opportunities are endless.

That's the first lesson that when you have that entrepreneurial gene, when you see things from that point of view, opportunities truly are endless. Our brains see opportunity in everything. We're always coming up with the next million dollar idea, or we're always seeing, oh, I could totally make money doing that. The ideas are not a struggle for an entrepreneur, ideas are a dime a dozen. It's the execution where the work comes in. But I truly believe that when you see opportunity in anything, you're opportunities to find

Access are also endless. And this is really a different mindset from that of an employee or somebody who is not entrepreneurial minded, non entrepreneurial minded people who often have that employee mindset see fixed opportunity, they think, Oh, I have to get this job so that I will make as much money as I want to make it. That's the source of my money. But when you're an entrepreneur, you see money as something that you can access at any time through any means possible, right? You see money making opportunities in literally everything, I could not count how many times growing up, my dad would have the next million dollar idea. I feel like it was totally this like recurring theme growing up, like, oh, Dad has another great idea.

And my dad has had some really great ideas. And he has started some really, really solid businesses. And he has built some very successful businesses. And he's also built some non successful businesses. And I think that really understanding that there's opportunity in everything is such a beautiful lesson, when those things don't work out. As you might know about me, one of my core values is failure, which is such a weird core value when you tell people that but truly my passion for failure came from seeing somebody and having it modeled for me that failure is the way to success. And I think that so many people grow up fearing failure. And instead of that I grew up fearing not trying, I grew up fearing pulling my punches, I grew up fearing not doing anything about the things that I loved.

Because I knew that if something didn't work out, opportunities are endless. And there's another one right around the corner waiting for you to pick it up and run with it. And after seeing my dad build multiple businesses to various levels of success, I knew that whatever I set my mind to I could make successful, because it wasn't about the opportunities. It wasn't that my dad was dealt this hand of really great business ideas. It's not like he was in the favor of the universe, like this is the guy who's gonna have all the great ideas, right? He was not given all of these ideas, these ideas are everywhere. It is the execution and your commitment to them, and your ability to make something successful.

And so if you try something, and it turns out not to be the thing, try something else, see another opportunity be open to receiving another option. And that's how I have learned and how I have come to value failure so much as a core value of mine. Because I know that if I put my heart into something, and I give it my best effort, that either it will be wildly successful. Or it will teach me exactly what I needed to learn in order to make that first thing happen. And I don't look at it as meaning anything about myself, I don't look at it as something to be feared or something to avoid. I look at failure as an opportunity. And like I said to an entrepreneur opportunities are endless. So that's been one of the biggest lessons that I learned as a second generation entrepreneur.

The second lesson I'm going to share with you today comes with a little bit of vulnerability, if you like this episode in general does, just because I don't talk a lot about my dad or my upbringing or anything like that. The second lesson that I learned from my dad, or as a second generation entrepreneur is one that I had to learn the hard way. Which if you know anything about me, that's the only way I really learned any lesson. It's kind of the story of my life. But I learned the lesson that time is your most valuable resource. And I learned this lesson in a very hands on way. So when I first started my business, I was committed. When I started my business, I had two very young kids. I had a three year old and a six month old baby.

And so my and I was a stay at home mom and my husband had just lost his job in case you didn't know my little origin story there. So my husband was picking up work. He was working for my dad for a little bit and he was driving Uber at night, trying to make ends meet. And I was like, You know what, I'm actually going to give a go at this business thing. And so we had made the decision early on in starting my business that I will be with the kids all day he would be at my dad's office. At 5pm, he would come home, we'd feed the kids, put them down by 730. And then he he would go drive Uber from 8pm to midnight, and I would work on my business. And we did that routine for nine months. And this is the unsexy stuff that no one tells you about starting a business, right? You can hear that I made $100,000 in my first 11 months. But what you don't hear is that for nine of them, I was burning the candle at both ends, and hating every minute of it. I was dedicated, and I was committed. So I made it happen.

But I also was working late at night, I was trying to fit it in between time with my kids, my husband was working all the time, we never saw each other our relationship was on the rocks. Like there was a lot of not great things about that. And I think that some people, sometimes we don't talk about that, I think oftentimes we don't talk about that, right? We just talked about the shiny part at the end the look, but I did it, I made six figures in 11 months, and that matters. So anyhow, back to so that's where we were. And in the middle of this, I had found myself playing out this situation that I experienced as a kid, which I often find we do, right, I find that the patterns that we play out over and over as adults are oftentimes things that we had play out in our lives as kids, right? We're replaying all of those things over and over again.

And when I was a kid, my dad was very present in his business, he was very committed to building his businesses. And as a kid, I experienced him as caring more about his business than he did about me. And now I know that that's not true. My dad loved me, obviously. But my dad spent more time building his business than he did as a dad. And I've had a lot of conversations with him about this. So I have no like pent up aggression or anything anymore about it. But that was my experience growing up. And in this time, when I was in this period of hustle, I started to play out that same trope, I would rather be working than spending time with my kids, I would find myself annoyed having to play with them when I could be working right. And I was playing out the same story that I had experienced as a kid. And I realized that I had created this belief in my mind that I can't be a successful entrepreneur, and a present parent.

And as soon as I figured that out, as soon as I heard myself think that I was like, Whoa, that's because I had a father who I felt like prioritized being an entrepreneur more than he did prioritizing being a present parent. And thankfully, I have an amazing relationship with my dad. And so one day, I'm sure he was not expecting this. I went to his office and I was like, Hey, I have a thought I have a question for you. And we talked about it right? I brought up this idea, I brought up how I was kind of playing that out. And I brought up this belief that I had found myself believing that I couldn't be a successful entrepreneur and a present parent. And in my conversation with him, I got the closure and like I got everything that I was looking for, because I'm very grateful that he and I have such a great relationship. But one of the things that he said was that if he could go back and do it again, he would flip that around.

He's like, you cannot get that time back with your kids. And it's one of his only regrets. Because businesses are fleeting businesses are not like you'd cannot cuddle up with your businesses at night, right? But your relationship with your kids is forever in him telling me that was so powerful. Not only is like a kid who felt ignored by her father, growing up because of his businesses, but also as a mother, who felt like she was doing the same things. And then that moment, it was like a light switch went off in my mind. In my priorities shifted. I decided that in order to be a successful entrepreneur, I had to be a present parent. And that when I am fully present with my kids, that's what makes me successful. And the more time I spend with them, the better I am in my business. And I shifted the way that I was showing up with them. I shifted the way that I was thinking about it. I shifted my boundaries around my business. I hired help. I stopped working so late at night we shifted the way my husband was working like we made it work and now

Not coincidentally, around that time was when I hit my first 10 Km month and really started to gain momentum in my business. And it wasn't until I really confronted this belief that I either had to choose between my business or my family, that I realized that I had chosen the wrong one, early on, and that I could make a different choice. And so if you are out there, and you have maybe made the other choice where you are working all the time, or you're always on your phone, or you're listening to boxers, from clients, with your kids, and you're not being fully present, and one or the other, I get it. And honestly, it happens sometimes for me, too. It's something that I'm continually checking myself with. And I have to remind myself that in order to be a successful entrepreneur, I have to be a present parent first.

And when I hold those boundaries, that's when I feel successful. And that's when my business grows. And so what I've done is I've created very firm time boundaries around my business time, and my mom time, and I show up fully to both. I try not to have my kids running around the office when I'm on calls, though, like, let's be honest, it's COVID. But very, very few and far between Has anybody seen my kids, or heard them, because thankfully, I have a very present husband who is in their lives, and watches them on a day to day basis. Parents that while I work, but when I am with them, I am not on my phone, I am playing with them, I'm present with them, so they feel fully mothered when I'm with them. And they don't feel like they're missing anything out. Or at least I don't think they feel like they're missing out on anything.

When I do work, and it's hard, I have to be honest with you. It's hard sometimes like when your Instagram is blowing up or when your DMS are blowing up and people seem like they need you. And it seems like an emergency. And I have to remind myself that we're not saving lives here, like this is not brain surgery. It's marketing, right? It's not that emergent. And if I can take that time to be with my kids, and really know that time is my most valuable resource. And that I can't get this time back. I know that I can make more money. Like I think a lot of times we as people would rather waste time to for the sake of more money, why we would rather spend more time to make more money. And what I learned from my dad, and from this lesson, and from this beautiful story that we have now is that money isn't everything and that you can't get the time back.

And so trusting that time isn't a non renewable resource, but money is and how can you make sure that you're maximizing your time, especially time with your family, if you have kids, in order to make more money in the long run? That was a very powerful lesson for me. And the third one in this one is something that I was just talking about this with him tonight at dinner like something we talked about a lot is you are your only fishbowl. And what do I mean by this? What I mean by this is that you can only grow to the level of success that you believe you are capable of. Our self belief is the fishbowl that we create around our capability for success. It's like the koi fish which unsurprisingly I have one tattooed on my foot in case you didn't know that about me I have a tattoo, just one.

I'm telling you all the things today's is like Jess is sharing all the things but koifish grow to the size of their pond. And so if you put a koi fish in a small bowl, they will not grow, they will only grow to the size of their container. But if you put a koi fish into a big pond, then their possibilities are not limitless, but limited list of the size of the pond that they're in, right. And we as entrepreneurs are only bound by our self belief. Our success is only bound by how much we believe in ourselves and how much we believe we are capable of. And this is something that has been such a valuable lesson for me because I know that I am the only thing holding me back. And I see this with my dad, too, like we were talking about a dinner tonight, how his belief in himself and his belief of what he's capable of, is the only thing holding him back from having whatever he desires, in his belief that He is worthy of having that and that he has done enough to have it is what's keeping him from having it.

And so if you are at a place in your business, where it just isn't growing, or you feel like no matter what you do, you're not receiving what you think you should be receiving from your efforts. Ask yourself, is my fishbowl big enough? Do I really believe that I am capable of the growth that I desire to have. Because if you want to be a six foot koi fish, but you won't get out of a three foot pond, do you really think you'll grow? You won't, you have to grow your self belief in order to grow your business. And your self belief is the only thing holding you back from having the business that you desire to have. And when you realize that you are the one that's keeping you small, and you're the one that's limiting your own growth, really prioritizing yourself grow growth is the key to growing your business.

And that's something that I've really prioritized over the last two years, it's gonna say two and a half, but it's not quite been that long. Two years running my business is that my self growth has been at the forefront of that journey, my ability to recognize the beliefs that I have, that are not serving me, and let them go and rewrite new beliefs and create new identities and create new truths that I can anchor myself into. And because of that, I've been able to expand my self belief to where it is now. It's so funny, because like I look back two years ago and myself believe was not where it is now. And I'm sure two years from now, I'll look back and say, Man, you've had so much growing still to do. And I think that's good, right?

I think as soon as we stop growing, we stop growing. And that's the problem. And so the last lesson that I'm sharing with you, the one that I learned from having a parent, as an entrepreneur, being a second generation entrepreneur, is that you are your only fishbowl, you are the only thing keeping you small. And that when you believe that you're capable of more, and that you're worthy of having more and that it gets to be as easy as you want it to be. That's when you'll find the opportunities that will reinforce that and make that true. So I hope that you found this helpful. I hope that these were valuable lessons for you. And I would love to hear Are you a second generation entrepreneur?

Or are you the first in your family to choose this path? Or maybe you're like an eighth generation entrepreneur in your great great, great, great, great grandmother invented something forever ago, that would be really cool to you. So I would love it. If you would let me know. Share your story with me. I would love to learn more about your journey into entrepreneurship and the things that guided you along the way. Also, I would love it if you would share today's episode if it resonated with you. So just take a screenshot where you're listening and share it on Instagram and tag me at just dot o Connell underscore by the way Have you ever run a five day challenge that felt like it went great only to have way less conversions than you expected? If you want to learn the secret to high converting challenge launches, you do not want to miss next week's episode. Thank you so much for listening and I will see you on my next episode.