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- [00:00]
Sponsor Representative
The number one thing I hear from founders isn't AI, it's hiring A players are rare and expensive. That's why Smart founders and CEOs are using near to hire top tier offshore talent in Latin America. Over 700 companies like Function, Health, Expensify and Deal use NEAR to build their teams and save hundreds of thousands in overhead from senior engineers to heads of accounting to growth marketers. If it can be done remotely, near can find you the right person. You'll save up to 70% compared to US hires, but the real win is the quality. These aren't freelancers, they're loyal long term team members who actually care about your business. Near moves fast. You'll get resumes in three days and fill most roles in under three weeks. And you don't pay a dime until you make a hire. One of near's founders is a Hampton member and plenty of others already use them. So if you're ready to hire the best talent in Latin America, you go to hirewithnear.com moneywise. That's hirewith N-E-A-R.com moneywise to get 5% off your first hire so I've been
- [01:05]
Jackie Lamport
thinking a lot about the word success and not in my usual train of thought, which leads to the fact that the word succession, I don't know, it just should be pronounced secession. But the real reason that I've been thinking about it is because after interviewing over 150 exited founders on this podcast, I've noticed a pattern that's kind of strange and interesting. These are founders who have objectively made it. They have wired life changing amounts of money into their accounts, they have sold their businesses, they started new businesses. And yet over and over we hear the same thing.
- [01:30]
Exited Founder Guest
I got 40 million in the bank.
- [01:32]
Jackie Lamport
In addition to what I had.
- [01:33]
Exited Founder Guest
I still didn't feel like a very successful entrepreneur.
- [01:36]
Sponsor Representative
I don't have imposter syndrome. I am an imposter. The underlying tone was still a deep sense of anxiety and fear and I'm
- [01:45]
Jackie Lamport
not enough as a person.
- [01:46]
Sponsor Representative
I don't know why I continue to feel this way as everything objectively around me is getting better.
- [01:51]
Jackie Lamport
So there's a lot to unpack here because if you have hit every external marker of what success should be and you still don't feel it, then, well, what is success? So based on the conversations I've had with over 150 founders, the access that I have to the Hampton community, and all the responses that I've seen throughout doing this podcast for two years, I'm going to try and answer that question. My name is Jackie Lamport and this is Money Wise a podcast not about how to become a founder, but one that is for founders who are in it. On this podcast, we're radically transparent about the numbers, the emotions, the raw personal journey that every founder goes through, whether they expect to or not. And if you're interested in being a part of the community that this podcast is made for, then you should check it out@joinhampton.com if you are a founder doing at least 3 million in revenue already, check it out. Success is interesting because it's one of those things where it's kind of completely objective and subjective at the same time. In its simplest form, it, you know, might seem to be just meeting a set of requirements, or at least that's my understanding of it. But let's consult the Elders Webster's Dictionary defines success as a few things, actually a degree or measure of succeeding. That one isn't super helpful. A favorable or desired outcome. Also not super specific, but perhaps the third one is the most apt for this conversation, or at least this crowd, the attainment of wealth, favor or eminence. Regardless, we're in a similar situation. The definitive requirements for success can be endlessly debated, and really, they depend on perspective and context. Here's an example. If I decide that I want to read four books this month, and then I only read three, then it's pretty clear that I didn't succeed, right? Or so it seems. If the real point of the goal was to be more intentional about reading, or really, I love reading, so it would be to carve out more time to do something that I know that I love, then wouldn't that be successful, or a win at least? But then what if I didn't enjoy it? What if I was pushing my way through and then I also failed? That would be failure, right? But then I'd argue that, well, the goal was actually just to build discipline. So yes, I didn't get through all of it, but I was building on my personal discipline skills. The point here is that you may be able to define success based on the achievement of some preset targets. And that might actually be the simplest way, the most black and white way to describe it, but it doesn't really capture what it means to be successful, because black and white doesn't really exist, mostly. And for founders in particular, that ambiguity is exaggerated because, well, you have such great scoreboards. Look at revenue and what the exit size was, and what's your net worth? It becomes really easy to create A neat little checklist of what it means to be a successful founder. And on top of that, the archetype of a founder is somebody who's typically really goal oriented or numbers oriented. The story that we've seen again and again on the show is somebody starts a business, maybe that's methodical from the start. Maybe they just started something and eventually realized, hey, there's something to this. Well, then they start creating these very specific goals or milestones that they need to hit, like net worth or maybe just revenue of the business or an exit size. And then they start looking at other people and comparing what they've been doing. And then eventually it just becomes this thing where it's like a super specific, maybe even unattainable goal. But the moment that you define success as a specific outcome, like an exit or a number or even just a title, you are also creating something else. A post exit era. So then there's the before when you're chasing the goal, and the after when you've technically hit it. But this after period, well, that's when things start to get weird. Often, especially with money, goal posts start to move. I need $1 million in cash to feel successful turns into I need 10. I need to have a net worth of 10 turns into I need to have a net worth of 100 million. I need to exit one business to be considered a successful founder turns into, actually, I probably have multiple exits to be a successful founder. The goalpost moving is just one potential outcome. Another thing that we've seen a lot that happens is that people do hit their goal. And on paper, it really looks like they should be celebrating they are successful, but what they actually feel is nothing. Maybe a little bit of relief financially or the stress of the business has gone away, so they're feeling a bit better. But over time, they just have this inexplicable emptiness.
- [06:30]
Exited Founder Guest
My self worth was based in how hard I worked on something. I didn't have that anymore. I thought that success would be this thing that would sort of complete me, if you will. And it just didn't. And I couldn't believe it. All right, money wise listeners, here's the deal. On this podcast, we talk about money, and that's great. But the one thing that's even more important than money is your health. And a few years ago, I made a change. So I made a change to get fit. I wanted to get fit for vanity reasons. I wanted to look good, but I also wanted to feel awesome and hopefully live a long time. And the way that I made this change after after years of struggling was I hired a coach and it changed my life. I went from being like 25 body fat to 13, sometimes 12 body fat. It changed my life and that's why today's sponsor is Daily Body Coach. It's a premium online coaching service for ambitious entrepreneurs and executives looking to achieve their dream body and perform their best. Daily Body Coach is run by an exited software entrepreneur and Hampton member and in fact a bunch of other Hampton members are using Daily Body Coach and they hook you up with a super personalized exercise and nutritional roadmap to help you achieve your goals. Their expert coaches are available seven days a week so you can rest assured knowing that you have someone to hold you accountable every single day and to keep you on track. You can have it all. They offer a 100% money back guarantee within 30 days, no questions asked. Make a change. Check them out. Daily body coach.com/moneywise Again, that's dailybodycoach.com/moneywatch
- [07:56]
Jackie Lamport
internal deep self fulfilling gratification doesn't just happen because you met some objective or you have some number in your bank account. But if you've been head down for years working toward that, the gap between what you were expecting to feel once you hit it and what you actually feel can be really brutal. Because goals and milestones like this obviously aren't going to bring success in that self fulfilling, prophetic kind of way. And when it doesn't, you start getting the feelings of being an imposter or wow, I really thought that this is what I should have been chasing. Was I wrong? Or worse, why don't I feel the way I should feel? Is there something wrong with me? And then comes the moment that most of the founders we've talked to who have been through this usually come to. Which is okay. If this isn't success, then well, what is? So maybe the easy answer here is to accept the hard one, which is that it really is subjective. Earlier I said that it's not black and white, which means that in the gray you get to decide what success looks like to you as long as you're honest with yourself. So whether or not you feel successful really depends on you. It depends on what you value and what you found brings you a sustainable sense of gratification the more you spend your time on it. So I've thought about this a lot and for me it comes down to three things. One is realizing my own potential, which I realize is actually the one that overtakes. Or that's like the deep Sense that I feel for when I have to like prove myself, that's the one that matters more to me. Not so much actually creating something and putting it out there and getting response that's positive. It's the fact that I feel confident in what I've done, that's the deeper sense of it. So I could still do these things and try to, you know, be the best that I can be, but it's coming from an internal place, so I'm happy with it. That's all that matters. Two, deepening my understanding of the world around me. And three, feeling confident that I'm having a positive emotional impact on the people that I interact with. If I'm doing those three things, then I feel successful, at least for now. Therefore, monetary, business or career objectives are just that, objectives. They're ways of supporting that inner definition, not replacing it. You may or may not relate to my version of this, but that's kind of the point. Everybody's version is different. So as a founder, instead of expecting a big exit or a net worth milestone to magically make you feel fulfilled, instead think, okay, well how does the goal that I'm chasing connect back to the person that I want to be? And how does the way that I'm doing it make me feel fulfilled or successful on a day to day basis? There's a specific phrase that comes up a lot with guests once they hit that period post exit and they're feeling a bit lost. And then they get to this same point, which is when they say I need to find my purpose. But I have a bit of a hot take here and it kind of contradicts the majority of the guests on the show. But it's that I don't believe in purpose. Hear me out. Because really it's just because it feels reductive. It feels like it boxes you into this self identity, this idea of what you should be doing in the world, which then means that if you grow and change, there's this layer of friction because you're suddenly questioning your identity every single time something might change what you think your purpose is. On top of that, I do in my core believe that existence is chaotic. I think that everything that happens is because of the compounding series of events that preceded that thing happening. Which also means that I think that trial and error is nature's way of bringing about inevitabilities and that we may perceive as fate. Or at least that's how I would perceive what fate is. Because of that purpose in like the cosmic sense of the word doesn't really make sense to me because it implies that you are playing a role in bringing about a predetermined future. And the only reason that I'm actually making this digression is because if you do think like me, then it means that you might feel resistant to the idea that self fulfillment, self success in life comes from a sense of purpose. Because I actually still do believe that. Because really what's happening is I'm actually just responding to the more spiritual or dharmic association to the word purpose in this context. So let's strip that and go back to our good old friend Merriam Webster. There it says that the definition in this context is the feeling of being determined to do or achieve something, which. Yeah, I mean, I believe in that because it's basically what we described in the last section, which is that self defined determination or that inner sense of self knowing what matters to you and using that as your core driver, working toward that every day. That ongoing nature, by the way, I think is actually a really important distinguisher between the internal and the external versions of this, because the external versions, as we have already talked about, have a cutoff period. They have the milestone and then there's the post era. Whereas this internal version is something that stays with you your entire life, which means that that fulfillment that you get from continuing to feed, that also stays with you your entire life. You don't get that period of loss and because you don't lose the thing that you're working toward. And that's where most of the founders that we've spoken to have actually landed themselves. It's not about my purpose is to do this thing. It's that this is what I value, this is what I feel like my greater purpose is, and I'm going to build my life around that. So I'm going to do things that contribute to that AI Search is quickly
- [13:20]
Mentions.so Representative
becoming one of the easiest ways for companies to get in front of customers right now, and the best way to take advantage of it is with mentions. So it was built by a Hampton member and it gives you one simple dashboard that shows you exactly how your company ranks inside LLMs like ChatGPT and more importantly, what you need to do to get ChatGPT to recommend your product or service to potential customers. Every 10 years or so, a new growth channel is born. And for a small window of time, companies are able to get attention for cheap and drive massive growth. Imagine being able to go back in time and buy Facebook ads in 2007 with all the knowledge that you have now, or even being able to go back and create TikTok content in 2017. The companies who took advantage of these growth channels in their early stages experienced insane growth.
- [14:00]
Jackie Lamport
And guess what?
- [14:01]
Mentions.so Representative
This is exactly the opportunity you have right now with AI search and the ability to show up right in front of your customers on LLMs like ChatGPT. Mentions so makes it easy. AI search platforms like ChatGPT that are so highly trusted, people are using it for everything from relationship advice to legal advice, or even as their own personal therapist. That's why many companies are reporting conversion rates of up to 17 times higher when their products are recommended on ChatGPT compared to traditional search on Google. So go to Mentions so right now and sign up with the discount code moneywise for 50% off your first month and a free AI search from the Mentions team who are behind the SEO campaigns of some of the biggest and fastest growing companies in tech, like Beehive, Kajabi and American Express. That's Mentions so code moneywise for 50% off your first month and a free search audit.
- [14:52]
Jackie Lamport
And now we get to the clear part of everything here, the lesson for founders. So the big thing that I keep coming back to here is not that we need to redefine success, it's that we need to stop confusing external success with internal success, because they're not going to bring fulfillment equally. There is such a thing as financial success or business success, or even I read the four books, or I didn't read the four books. You can say I hit a million dollars. I am successful now. Or maybe you stay true to those metrics and it feels good and you don't feel like an imposter or whatnot.
- [15:26]
Mentions.so Representative
That's all good.
- [15:26]
Jackie Lamport
Those things exist and they are versions of success for sure. But the recurring problem I've noticed, and the thing that a lot of the founders that we have spoken to have had to overcome is when you do confuse those two things and those more materialistic, for lack of better words, milestones become your version of success and what you're looking for fulfillment in. And when that happens, two things happen. One, like we said, the goalposts never stop moving. So 1 million becomes 10 million, 10 million becomes 100, and so on. And as that consistently changes, and honestly, like pissing matches online, that happen where people say, well, you're not a real founder unless you've done this well, then you can start gaslighting yourself into saying, well, I'm not a real founder yet, because I didn't do this benchmark or whatnot that's not healthy. And the second thing, like we said, is the winds just feel superficial, so you hit the marker and then you just feel empty and aimless and you don't know why. So on your founder journey, it's really important to continuously look toward your inner version of success as your source of fulfillment and the external one as just a way to support that and create the world that you want to be in around you. You also need to make sure that those two versions of success are connected and make sense together. They can't support one if they contradict each other. Obviously, again and again, the founders that we've talked to who have been through all of this, who have hit the success targets on paper and whatnot, they all realize the same thing eventually, which is that at the end of the day, you are still you, no matter what happens externally. So if that inner core, that internal sense of what is fulfilling to you isn't there, then that external one that you're working so hard to build is really, whether you realize it or not, just a very fancy, fragile house of cards. And the interesting thing is that again, because of the people we've talked to, the more you focus on that internal side, the easier it becomes to hit the external success because, well, I mean, you're healthier, right? So I've been working on the show for about two years now. I have spoken to a lot of people, I have written a lot of scripts, I've read a lot of your feedback. But that doesn't mean that the way that I've written this out is the right way to use success. This format of the show, the producer takes side of things, yes, it takes all of those things into consideration. So I'm not just like, you know, blindly throwing out my opinion on these matters, but I mean, it still is my opinion through my perspective and how I'm perceiving the things that are incoming in the first place and all of the different things in my life outside side of the show as well. So I'm actually really curious what you think, because I think that there's a lot of room to discuss. Let me know in the comments what you think about this way of viewing success. If I'm right, if I'm wrong, if objective milestones and goals are the better way to look at it. I don't know. I'm curious. And in case I don't say it enough, just so you know, this is a podcast made for the Hampton community, which is a founder only community for high growth entrepreneurs. If your business doing over 3 million in revenue, and you're looking for real talk with people in the trenches, go to joinhampton.com Also, if you're curious about launching a podcast or leveling up one that you already have, that's what we do at Lower street, and that's where I work. If you want to learn more about that, you can check it out at Lower street co I'm Jackie Lamport and see you soon.