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Get ready for an exhilarating journey in this edition of Raw and Real Entrepreneurship, as we cut through the unnecessary details and dive into the business world with Kieran O’Brien, the 24-year-old SaaS prodigy who has achieved two significant exits.

-Kieran O’Brien

Topics covered in the interview

Company growth

Funding for start-ups

Building and maintaining relationships

Hiring strategies for start-ups

Company culture

Kieran O’Brien’s Bio

Kieran O’Brien is a 24 year old entrepreneur, marketer, and technology founder. Kieran is currently the Founder & CEO of Shopgenie, a vertical SaaS platform for the $800B automotive repair industry.

Follow Kieran O’Brien

Instagram: @kieranobrien 

Twitter: @thekieranobrien


Show Noted

Read Full Transcript

Susan Sly 00:00
Well hey everyone, you are going to be so inspired in the show and I'm very confident about that. My guest today is Kieran O'Brien and Kieran has been on the show before, you may know him. He is, he has been featured in Business Insider, major publications. He is a 24 year old entrepreneur. And he has already had two successful SaaS exits. At age 16, he created his own company Geared Social, he was making 1000s of dollars a month in affiliate marketing. And even though he was accepted to UPenn, he convinced his parents to allow him to be able to go out and do his entrepreneurial journey. And he has not looked back since. I've known Kieran for I think six or seven years. He is one of the most disciplined people I know. And I believe, I believe that age and wisdom do not necessarily coexist. I know many people in their 60s and 70s, who are immature and they do not have their lives together. And I have had 12 year old entrepreneurs on the show who have more wisdom than a lot of 40 year olds I know. So Kieran and I, in this episode, we're gonna talk about what it's like to build a business, what he's learned about fundraising, pitching hundreds of people and having 90% of them reject the pitch, what he's learned about bringing on advisors and growing a company and it is an inspiring interview, and I absolutely, absolutely am so excited for you to listen to it. And before we get into the show, a couple things. If you aren't following me on social personally, please do. I have a lot of new announcements coming out. And you'll see those on Instagram. So I'm @Susansly on Instagram. And then of course on X, I'm @Susanslylive, so you can check it out there. And go ahead. And if you are interested to see what I am doing with my new company, please go to Get on the insiders list. You will hear more about it. I also have live free coaching coming up for people who are members on that list. Right now membership is free. I'm not saying it's going to be always but it is right now. And so you can have the opportunity to come and do live, free coaching with me. So go ahead and check that out. So with that, let's go ahead and get into this episode with my friend, Kieran O'Brien.

Susan Sly 02:34
This is Raw and Real Entrepreneurship, the show that brings the no nonsense truth of what is required to start, grow and scale your business. I am your host Susan Sly.

Susan Sly 02:48
Well, hey, what is up, Raw and Real entrepreneurs wherever you are in the world, I hope you're having an amazing day. And as I said in the intro, you know, this guest is more than an outstanding entrepreneur. He is a friend. He's someone who never fails to inspire me. And on top of everything, the day we're actually doing the show is a Saturday. So it just so happened that we could both make it work. And it's been a while since he's been here. The last time he was here, he was working on another top secret project that he went on to sell as I spoke about in the intro, and now he's got a new company and he's already had two SaaS exits. And yeah, it just, it just never ceases to amaze me how he is always going for the next goal, and the next goal, the next goal. So Kieran, I'm so happy we have this time to sit down together. And welcome back to the show.

Kieran O'Brien 03:51
Yeah, thanks for having me, Susan. It's good to be here.

Susan Sly 03:54
So Kieran, I want to jump right in, you know, the last time you were here, you were working on launching media kits. And that company has now sold, but I want to go back a little bit because I remember so many dinners and talks. And when you were getting ready to build that company, and let's jump in there because initially with MediaKits, you decided to bootstrap that company. And you were using essentially money from one venture to support that company. So can you, can you talk about that? Because as entrepreneurs, often there are many different ways we can go about funding companies, but yours was, that was an interesting journey.

Kieran O'Brien 04:37
Yeah, definitely. And you know, the funny thing is that, looking back, it's like, you know, hindsight is 2020 but I only bootstrapped that business in the beginning because I didn't know any better, right? I had never taken money from somebody else before. I never, I had never had the luxury of being able to use someone else's capital to build a business. And so it was, it was just pure, like naivete that I was bootstrapping that in the beginning. And then one day, my co founder, Casey came to me and he was like, hey, you know, I've had all these angel investors on my podcast, what if we got them to give us money to build this business? And that kind of completely broke my frame. And I was like, Wait, you're telling me that people are willing to give us money to build this thing that may or may not work that has no revenue, that has no product market fit yet? He was like, yeah, they're called angel investors. And so that was kind of a definitely a life changing moment for me when I realized that.

Susan Sly 05:33
And then, like, looking back at that, and I'm glad you mentioned that because it's, there's, on the show, I've interviewed now 360 founders, there have been 12 year old founders, I know you and I are very passionate about like, inspiring young people. We've had, you know, billionaires who've been on the show like Glenn Stearns, and there are different schools of thought around that, like, I'd rather not bring in OPM, other people's money until I know that there's a product market fit, or I, you know, I'm just gonna go all in because I, it's going to fuel me more. So talk about the psychology of bringing in those first investors and what it was like to do those first pitches. And did you like, did 100% of the investor say, yes.

Kieran O'Brien 06:18
No way. Yeah, that's, um, it's a really interesting thing. I mean, the psychology behind fundraising is so, is so interesting to me. And I studied a lot when I was raising for my first venture, and for my most recent one, and I think there's a lot of like mental frameworks that you have to operate within to be able to do it right. And yeah, to your question, no, we pitched over 350 investors for MediaKits, and we, I think we had 32 investors in total. So it's about a 10%, close rate, you know, from all the different conversations we had, and then it's important to know that to get a conversation to be on the phone with those 350 people, we probably had to have, you know, four or five conversations for every meeting that was accepted. And so just do the math, like the, the close rate from conversation to, you know, money in the bank to a check is extremely small. And it can be, it can be very, it can be very defeating when you're getting no after no after No. And, you know, everybody's telling you that, oh, it's not going to work for XYZ reason or, show me a little bit more traction before, you know, before I invest, and then you're looking at your bank account, you're like, I don't have time to show you more traction, this is gonna go out of business. And so there's, there's a lot of really stressful like, near death experiences that a lot of founders have, especially in those early days. But I will say I think it makes you a better entrepreneur. And I think it really makes you get creative and, and get scrappy with the way that you're building your business. So I think everybody has to go through it. It's almost like a rite of passage.

Susan Sly 07:54
And thinking about it, like so many people quit, you know, after one failed attempt, or what they would feel as a failed attempt and you pitch 300 VCs. And, and you and I, the last time we went hiking, we were talking about this, like I've pitched so many VCs, like for big pitches for you know, A rounds, seed investors, angel investors, and the more people you're pitching, the less attached you are, but the fewer people you're pitching, you're so attached to like, please just put money in the company. Were you already at revenue when they started investing?

Kieran O'Brien 08:33
For MediaKits? No, no, we had no revenue. It was, we didn't even have a product. It was a clickable prototype when we raised our first check. And our first check was from a gentleman named David Meltzer, who's an angel investor out of California. And he, yeah, he just believed in us, he believed in Casey and I, he's actually, Casey's now fiance, he's her uncle. And so she was also a part of a team. And I think that that had a little bit to do with it. But you know, at the end of the day, it's, it's, it's really belief in the founders. And so angel investors, they're effectively gambling, right, there's no, you know, when you're investing in like an A or B round, there's traction, there's product market fit, in a lot of cases, there's revenue, you know, there's something substantial, when, you know, in pre seed and seed rounds, it's, it's oftentimes just a napkin idea, and a couple people with a dream, and there's not much more than that. And so as an angel investor, you just kind of have to make the right, the right bets. And you have to bet on the founder that they're going to figure it out. And that was one of the biggest mindset shifts that I had, as a founder is understanding that these investors, their business model, and how they put food on the table for their families, is by being a capital allocator. And they know that eight or nine times out of 10, that investment's gonna go to zero and that's okay with them. Right? Now, that's not an excuse to build a bad business. That's not an excuse to lose people's money, but I think it does take a little bit of the pressure off knowing that you're out there, you're giving it your best shot, you're getting in that bet. And if you fail, which is again, statistically very probable, but also, it's just a reality that you have to accept when you're building a business, that you can go out there and do it again, you can have another at bat. And I think that was a big mindset shift that I had to have when I was fundraising for my first company.

Susan Sly 10:24
Did the investors shift the direction of the MMP? And for, because we are, I think, the team tells me we're in 166 countries. I was texting you back Kieran, and so I know not everyone's first language is English. So MMP stands for Minimum Marketable Product. We used to say MVP, but the new language is MMP because given that money is not cheap anymore, investors want to see an MMP not a, not a beta, they want to see like what can you take to market and start to get money? But did the investors that came in, those core investors, did they help, for you and Casey, did their purview shift what you were taking a market?

Kieran O'Brien 11:07
Um, I think yeah, I mean, that's an interesting question. I think it really depends on the type of product and also the type of investor. I think, for MediaKits specifically, we were, we had so much conviction in what we were building and what our MVP or MMP was at the time. And our investors knew that, right. And so I think, in a lot of cases, if the, if the founder has conviction, and the investor knows the industry enough to know that the founder knows what they're doing, I think the best investors put money in and get out of the way. Now, that's not, that's not always true, there are absolutely businesses where the barrier is extremely high, or there's a ton of technical risk. You know, there's always this kind of this balance between market risk and technical risk. Market risk, being a company that's relatively easy to build from a technical perspective, but getting it to market and getting paying customers is the biggest risk. And then there's businesses, which I think would apply to, you know, the business that you've been building the last few years, where there's no market risk, there's absolutely a market for it, there's people that are ready to pay for this thing. It's just the technical risk and being able to build it in the first place. And so I think my opinion is that most, most startups with high technical risk, probably take more advice from investors and probably attract investors that are more strategic on the technical build out of the product side of things, versus in the MediaKits' case, where the technical piece of it was the easy part. And the market risk was really where most of the risk was. I think that's where our investors were able to come in and help us with our go to market, help us get in front of the right people, help us get in front of the right enterprise, customers, etc. So I think that's probably a good distinction.

Susan Sly 12:52
I love that distinction. And thinking back in building MediaKits, and I remember we were talking about it before, like you started raising money. And you're very, to your point, you were, you and Casey you were very convicted. Like, we know there's a market for this, we know there's a problem. It's easy to talk about the problem, we've got a solution for this. Do you think in 2024, that you would have had the same tactics that you had when you built MediaKits?

Kieran O'Brien 13:19
No, no, not at all. I think Well, there's two parts to it. There's one, the first part is that we didn't know what we were doing when we were building the company. And we're just kind of building the plane as we took off. And the second reason is that the landscape has changed so much in that sector, around influencer marketing and the different platforms that we were advertising on, and that we got initial traction on. You know, one of the reasons why MediaKits was so successful and why we were able to get 10s of 1000s of users so quickly, was because of kind of the rise of TikTok and this new platform that was just dumping money into advertising and getting users in North America. We were able to go viral on Tiktok a few times for a consumer product that was very applicable to that audience. And you know, now, these days Tiktok is extremely saturated. There's so many different creative economy, influencer marketing startups that would be competing with MediaKits if we were still running it today. So yeah, I mean, it's an interesting thought experiment to think about, you know, if we were still running the business today, how would we be marketing it? I mean, I always like to try to stay ahead of the curve. So I'm sure we'd be doing something creative. But yeah, it's definitely a lot more competitive than when we initially started the business in 2020.

Susan Sly 14:29
Well, you're, and Kieran you're such an avid reader. So I know you're familiar with like blue ocean red ocean strategies, right. So like timing is a piece.

Kieran O'Brien 14:39
I have the blue ocean book right here over my left shoulder. Absolutely. Market timing is everything. I think that you know, when you talk about, like luck versus skill in entrepreneurship, I think that you know, there's always, there's always this conversation about, well, how much of it was luck and how much of it was skill? I think there's a healthy amount of both. But I think what a lot of people don't talk about is timing. Timing is a big, big, big piece of success. And I think, for the really good entrepreneurs out there that have always hit market timing really well. And I mean, you look at some of the most successful people in the world, the billionaires, the, you know, the Jeff Bezoses and the Mark Cubans of the world, timing is a massive, massive factor in their success. But if you really boil it down, it's still a combination of luck and skill. They have the skill, and then they had the luck to be able to hit the market at the right time. And yeah, I think a lot of success boils down to market timing, and trying to time the market is always very difficult. But I think the best entrepreneurs have kind of a sixth sense. And they just know, hey, this is something that's going to be disruptive to this industry, it's something that's going to catch legs. But then the other thing you have to realize with timing is that it's just a matter of time before competitors start popping up. And all of a sudden, it's a red ocean rather than a blue one. And you have to figure out where to go from there. So yeah, timing is a massive factor for sure.

Susan Sly 16:03
And those relationships, right, we were talking about before we started the show, relationship, collateral. And since it's Raw and Real Entrepreneurship, the you know, the thing I was thinking about whe I'm talking to Kieran about is that from a place of vulnerability, is that when I stepped down as Co-CEO, from my former company, to start this new company, I was wondering how many of the relationships were based on my role as Co-CEO of an AI company, even though my new company is an AI company? And Kieran and I were talking about that, that I think relationships really feel quote unquote, luck, right? Because Kieran, one thing, I want the listeners to know about Kieran is Kieran is one of the most disciplined people I know. And so when Kieran says he's gonna do 75 hard, or Kieran says, you know, okay, well, we, were gonna pitch 300 VCs. So that means, you know, we're gonna pitch 10 a day, over 30 days, he does it. And he doesn't just talk about it. And so let's talk for a moment about the relationships because one of the, you know, we don't have to disclose who all the funders were for MediaKits, I'm aware of some of them. But some that you know, you had Silicon Valley funders, you mentioned, David Meltzer, David has sent many guests who are show so thank you, David and team. Love you guys, love those guests, they're great guests. So how much of that was relationship collateral that you built?

Kieran O'Brien 17:30
Relationships are everything. And I think, you know, my co founder, Casey was like the epitome of this, you know, with his podcast, and everything that he does, he is one of the best relationship builders that I know. And I tried to fit into it as well. I learned a lot from Casey in that sense. But pretty much every single investor on the cap table at MediaKits, and at my new company, were relationships from either Casey and I, or relationships that I had built through MediaKits that I've been parlayed into my new venture. And even now, with, with my new company, we don't, like we're not raising right now. We don't need investors, we're doing really well financially. But I'm still meeting with investors, because you still need to build and maintain that relationship capital. Because you never know when, when you might need it. And you never know when you might be able to help somebody else as well. And so, yeah, relationship capital is everything. You know, you should, you should never burn bridges, you should always try to pour into your relationships, because you never know when, you know when that, when that might pop up in your life. And so, yeah, I think that was probably, if I had to boil it down to how we were able to get funding for MediaKits, it was almost purely relationships, because we didn't have any revenue or any, any product market fit to raise money off of.

Susan Sly 18:44
I love that you said that too about that you're still meeting with VCs, you're still meeting with different investors, because there's a, there is that opportunity to always learn, right? And, and like you, I'm a lifelong learner. And one of the things I did with starting this new company is I called up a friend of mine who is an LP out of fund. And I, I said let's go for lunch. And I said, this is what I'm doing. I showed him the deck, I showed him the TAM. And I said will you mentor me and help me reverse engineer this so I'd be investable to your fund wven if you don't invest in me? Like how do I look good to your fund when I'm ready to A round. And that's what we did, Kieran, we reverse engineered from the A, we did an 18 month out. And I did the same thing with another friend who actually has a fund that invests in biotech, women's biotech, and did the exact same thing. And I've learned a lot in the last several years in terms of building a company, scaling a company, doing multiple, multiple, multiple funding rounds. And this time I wanted to do it with the end in mind, and we may never even need that A round but I love that I have people who will sit down with me and say, yes, do this, do this, do this, or you're on the right track, or this is what your safe round should look like, you know, this is what I would do if I were discount around. And the moment that it went in the media that I was launching this new company, I was like, getting these messages on LinkedIn, like, can I invest in your company? And I've, I've learned a few things. Some of the, from guests, like I'll give an example, Lori Harder who has been on the show before, I'm an investor, full disclosure, in her new company. And she said, the only people who I will let invest in this company actually have to either have a podcast or have a minimum social media following because this is a b2c. And so I'm doing the same thing. Like that certain investor levels, you have to have influence or we're just not going to take you. That was one of the lessons I learned. And I know you and I spoke about other lessons like advisors, um, you know, advisors have to have skin in the game, you don't just give away your equity. Can you talk about that?

Kieran O'Brien 21:01
Yeah, absolutely. And one other thing that I want to touch on that you just said, too, is investors that have something to bring to the table, one of the big mindset shifts that I had when I was fundraising is, you know, especially when you're in kind of a state of scarcity, when everyone's saying no to you, and you feel like the world is collapsing on top of you, as a founder, it's really easy to get desperate and take what we call dumb money. Money, that's, that's just the money and it comes with nothing else. There's no support system, there's no advice, there's no, you know, relationship capital there. That's one of the worst things you can do as a founder, because then you're just, you're giving up money for, you're giving up equity in your business for money and money alone. And so one of the things that I that I always try to stick by is that you want to have smart money on your cap table, even if it's painful, even if it means you have to say no to investors, the mindset shift that I have is that if you have true conviction, utter conviction in what you're building, as a founder, then it should be a privilege. And you should view it as a privilege that you're offering an investor, the ability to invest in your business. If they're not doing you a favor, you're doing them a favor. And that's one of the biggest kind of mindset shifts that I had to have as a founder when I was fundraising. And same thing goes for advisors, right? Advisors want to help, they want to be helpful, their intentions are usually good. But at the end of the day, you don't want to give equity away in your business just for advice, right? I think every advisor should have some sort of skin in the game, even if it's just a small check, and you put some advisory shares on top of it, that's totally fine. But at the end of the day, you know, when you give, when you give away something for free, people don't value it. Right. And so I think that's one of the biggest learning lessons. We did give away advisory equity in Mediakits that we probably shouldn't have. And we stayed really strict about that at my new company. And I think that's one of the biggest takeaways that I had from that experience.

Susan Sly 22:57
Absolutely. And a vesting schedule and vesting KPIs, right, like, the just that, Yeah, okay, great. You know, the, it's interesting, because I remember our conversation, and we were hiking, we're talking about that. And I asked you, if you could go back in time, and do something different, and that's where this whole topic of conversation came up like, value your company. Don't just give chunks of it away. Let me ask you, because I'm just very curious about how your mindset around employee equity for early employees, because now you're on your second go round, because you're, what you built, the other one you built with Cayden and you just kind of sold it, was like using open source API's and stuff which was genius. Brilliant. But digging into, you have employees now, right. Off Duty. So how do you, how do you treat employee equity? Like how do you, you don't have to obviously disclose how you do it but this is one of the things when people are starting to bring on employees early on. I heard of a founder yesterday, he has like 11 employees, and he's paying them nothing. I'm like, God bless you. But that's not going to last very long. People won't work for free, right?

Kieran O'Brien 24:14
Yeah, no, absolutely. I think there's a lot of ways to do it. There's no right answer. That's one of the things I want to preface by saying. There's, it really just boils down to how you want to structure your company. There is absolutely a case to be made around like missionaries versus mercenaries. Missionaries, being people that are shoulder to shoulder with you like in battle so to speak, they're moving towards the same goal, the same objective, and you want them to be properly incentivized. And mercenaries are people that come in, in exchange for a paycheck, they get stuff done, and they leave. Right? And so that could be a contract or it could even be an employee that comes in for a short period of time just to, just to complete a business objective. And so the balance between missionaries and mercenaries at any company is always one that, it comes down to the founders preferences. For me personally, I believe with my new business that all of our early employees should have skin in the game, they should have equity or options in the business. And so they do, we have an ESOP, which stands for employee stock option pool, that everybody is a part of up until this point. And that's one of the big things that we believe at Shopgenie, at my new company is that we want all of our early employees to be going shoulder to shoulder with us, missionaries moving towards the same vision, the same goal. But that's not always the case. In a lot of companies, when they get to a certain size, they stop offering stock options, or they stop offering equity to their employees. And that's really just a decision that you have to make based on how you're trying to build the business and where you're trying to take it and what outcome you're looking for as a founder.

Susan Sly 25:46
That, and that ESOP is key because one of the things that people don't understand is that if you want really talented people, there are people who are amazing whether they're data scientists, sales, people, like engineers, and they're, they love working in startups, because they've already experienced some exits, they know that, you know, they're taking a chance too, they're taking a risk as well. But to be able to incentivize them. And so let me ask you this as a founder, do you treat yourself like an employee?

Kieran O'Brien 26:23
In what sense?

Susan Sly 26:25
Well, in the sense that the, I guess the that's a, you know, just thinking about knowing you as I do, let me step back for a minute. Again, you have an incredible, incredible work ethic. And I've watched you when there's something you don't know, you will figure it out. And you'll put in a 16 hour day, like that's not a big deal. So what I mean by that is, you've already had a couple of exits, so you could be that founder, CEO who's not in the business, but is kind of helicoptering the business, or are you right now in the business like an employee would be?

Kieran O'Brien 27:04
Yeah, no, I'm in the business. I was just on a demo before this podcast. Yeah, I think there's, there's two parts to it. And not everybody relates to both. But the one piece of it is that in the early stages of the business, the business doesn't survive without the founder being in the day to day. And I think, to a certain point, like at a certain point, that that's no longer the case. And the business kind of becomes self sustaining. They were actually getting to that point with Shopgenie where it's, it's largely self sustaining, there's still certain things that Cayden and I need to be involved in. But we are absolutely involved in more stuff than we need to be involved in because we want to be involved in it. Right. And so it's like, we have a very high standard of excellence at ShopGenie. And I think that's, that's another important thing is you could get the business to a certain point, whether it's a revenue or funding milestone, or number of employees, whatever it might be, where it's, you know, quote, unquote, self sustaining. But then at that point, is the envelope being pushed? Are you innovating to the fullest extent? Are you, you know, going above and beyond for your customers? Those are the questions that you have to ask. And in most cases, if you're like, a helicopter CEO, to use your words, that's not the case, right? The business is just kind of, okay, it's average, it's just scraping by. And that's just not the standard that we uphold at my companies. And so for me, it's a combination of the business isn't quite there yet, even if I wanted to do that. And the second piece of it is, I don't want to do that. I would rather be in the business day to day, I don't really know anything else. I just love to work, I love to build products and build teams and build something that's impactful. And so that's kind of why I'm in the, in the day to day still. And I don't really know if or when I'll ever not be in the day to day, because I just love playing the game too much.

Susan Sly 28:54
I can't see that. The day that happens, I might like fall out of my chair. That's the reason I asked that. Because it's different for me, because I know you, our listeners don't or some might, but that understanding of it. And do you have an office now?

Kieran O'Brien 29:13
We do? Yeah, yeah, we just got, we just got an office space for our Arizona based employees. And we're hybrid. So we have a lot of employees all over the, all over the country. We just hired our 22nd employee today. And yeah, we're, we're, we fly people in from all over the US to come and work out of the offices as well to keep that in-person culture going.

Susan Sly 29:36
Let me ask you this. So for someone who's like, listening, and they're like, Okay, 22 employees, oh my gosh, like this thing is really growing. When you think about, as a seasoned founder now, when you think about the hierarchy of who you hire first, so what advice would you give for someone beginning to hire? Where should they where should they focus because there are so many different schools of thought on this?

Kieran O'Brien 30:01
Yeah. Okay. I mean, the most basic way to boil it down is in the early days of a startup, even just like sub 50 employees, and when the, when the startup is like three years old or younger, the reality is everyone's wearing multiple hats, and the younger and less, less amount of team members, the more true that is, right. So at 50 employees, everyone might be wearing two hats. But at five employees, everyone's wearing 10 hats. And I think that's the most important thing. So what we look for a Shopgenie, when we're bringing on new team members, what we've looked for historically, and even today, hiring in the 20s, in terms of headcount, we're looking for self starters that are independent, that can manage themselves, and that are not, that are not afraid to roll their sleeves up, get their hands dirty, and do things that aren't necessarily in the job description. And that, what all three of those things boil down to is being a culture fit, right. So we interview people, we have our culture interview first, we don't care what your pedigree is, what your you know, your previous experience, or how many years you've, you've been doing, whatever, whatever it is that you're doing, we don't care about those things. In the first interview, we're looking at personality and culture fit, first and foremost. You get the best pedigree in the world, but if you don't pass that first interview, that culture fit interview, then you're not going to get a second interview at ShopGenie. And so I think that's the most important thing is finding people who are a culture fit. As a CEO and as a founder, you need to defend your company culture with your life, it's the only thing that matters. The people, especially when the company is early and vulnerable and small, the culture is the only thing that matters. And then everything else comes second. So culture fit interview, then you can talk about technical skills and experience and aptitude. Right? So again, like there's another thing that people say a lot is attitude over aptitude. That's another thing that we believe in pretty heavily.

Kieran O'Brien 31:51
What are, what are some of the questions you ask in the culture interview?

Kieran O'Brien 31:57
A few, a few examples are like, you know, previously, and you know, in your work experience, when is a time that you saw a co worker struggling and you jumped in to help them like, tell us the story behind that. Another one might be, you're getting to know the potential employee outside of work, What do you do in your free time? Do you do any volunteering? You know, what do you like to do on the weekends, like just getting to know them a little bit more, because culture fit goes above and beyond, you know, just who they are at work, right? Who you are in your personal life carries over to who you are at work. And I think that's also important to get some context on that. So yeah, just getting to know them as a person. There's not many questions that we ask around, you know, around what their role is going to be at Shopgenie in that very first interview, it's really just getting to know them as a person, understanding what their morals and values are, you know, understanding, you know, if they have a family, what does that look like? Tell me a little bit about that. I think those are all really important things. Because anything that they struggle with in their personal life is going to end up projecting into their work life. And it's going to end up affecting everybody around them in the workplace. And so that's why we want to get get to know them as a person in that first interview.

Susan Sly 33:13
I love that. And it's the, I've seen so often too, that when someone's not a great cultural fit, that it doesn't matter how skilled they are. And, and that's the thing, it's people keep employees too long. Because they're trying to make them into something they're not and it's not doing the employee a favor. It's not doing the organization a favor, it's not doing the other team members favor. So I thank you for sharing those questions. It's yeah, that that's interesting. So I, you know, we're getting to the end of the time, Kieran and I mean, the, the building this company, on the heels of two previous exits, as I said, and now and you've been so like, you know, on on YouTube, and your media interviews, you've been so transparent about, like, your focus and your objectives. And I know there are things you cannot talk about right now. But if we could, I guess, look into the future for Shopgenie, like the, you know, where do you want to be, let's say a year from now?

Kieran O'Brien 34:17
Yeah, um, shop journey is a very different venture for me, because I'm not chasing. I think if I reflect on the fact that I was 19 years old, when I started Mediakits, and I ha, I was immature, and I didn't really know what I was doing and there was so many other things that were influencing me. You know, I can say honestly, with with ShopGenie, I'm not chasing validation. I'm not chasing money. I'm not chasing headlines and you know, all the typical like Silicon Valley. You know, we raised a huge round of funding or we did this and that. We're focused on business outcomes. We're focused on building a profitable, you know, high EBITA cash flowing business, that impacts our customers that impacts our employees in a positive way. And that changes the face of an industry. That's what we're focused on. And everything that we do is in line with that goal. So we're not trying to go and flip this thing and, you know, exit, again, been there done that, not something that we're focused on, we're not trying to go and raise a whole bunch of venture capital and run a unprofitable business for years and years and years. We're very clear on our objectives. Again, it's impacting our customers, impacting our employees, and creating viable business outcomes for everybody involved. And that's kind of the, the, the ethos of what we're building at ShopGenie.

Susan Sly 35:43
It's, it is so wonderful. I think I've known you now for, gosh, close to I don't know, six years, seven years. And it's wonderful to see you on this journey. I have always said, I don't believe that age and maturity are the same thing. I know a lot of very immature people in their 60s and 70s. And so I love, it's so fun to check in and just to see what's going on and to see you know, where you are, and, and what you're building. And so I wish you every success, I'm so excited. It's always fun. And in the show notes too, all of the social media for Kieran and also for ShopGenie will be in there so you can check it out. And Kieran, I want to ask you one final question. So someone listening and they're like, Okay, wow, I'm feeling a little bit insecure, because I'm twice Kieran's age, and I don't have two exits under my belt. What, what piece of advice would you give?

Kieran O'Brien 36:46
Um, everyone has their own timeline. And I think the other thing too, is like, when you talk about, you know, there's a lot of people that have exits that aren't, you know, they're not all what they're chalked up to be, like, you know, for me personally, like, you know, we, we sold Mediakits for a relatively substantial amount of money, but we also have a bunch of investors, and a bunch of advisors, and multiple co founders and all that. So you boil it down, like, you know, it's really not as, as crazy as the headlines might make it seem. And that's even the case for multibillion dollar exits. There's liquidation preferences and all these different things that you have to think about. You know, there's I think, DraftKings are one of those big sports betting or sports gambling websites, they sold for billions of dollars, the founders walked away with nothing, because they had liquidation preferences where the investors got paid out first. And so when you're talking about exits, and you're talking about, you know, financial success in raising big rounds of funding, and this, this and that, again, it's a lot of it is vanity. When you really peel back the layers, like the grass is not always greener, some people are meant to build a bootstrap, profitable business, you know, or a solopreneur going out and just doing something that's repeatable, that cashflows like there's absolutely a time and a place for every different type of business. And success is not measured by, you know, specific outcomes or specific things. It's different for every single person. And you never truly know what the, what the reality is behind the scenes of these, you know, these flashy articles and headlines and all these things. So I think that's the first thing that I'll say. And the second thing that I'll say is everyone has their own timeline, right. So, again, you know, Warren Buffett didn't become a billionaire until he was in his 60s. And, you know, there's all these, all these stories about all these people that, you know, waited until later in life to achieve what they wanted to achieve. And really, it's like, you can't have, the hindsight is 2020. You can't be looking in the rearview mirror all the time. The only thing that matters is what's ahead of you and what you're able to accomplish today and tomorrow. So.

Susan Sly 38:53
Yeah, so so beautifully said Kieran, and thank you for that. And I love that, veryone everyone has the time and and that there's the saying, it's an old, going saying you only see the glory, you don't know the story. And we've had founders who've had you know exits for 300 million, 500 million, the list goes on and on. Even Glenn Stearns, when he was on the show, Undercover Billionaire, and Glenn's a friend of mine and like you know, losing the company and then getting it back again. Brandon Steiner having his company taken away that Steiner Sports his own name, taken away by the board and building two new companies and so there's, don't look at the shiny, you said this in your YouTube, one of your videos. It's like don't don't have the shiny object syndrome and that can apply to so many things not just entrepreneurial ADD but the like, don't look at something and think oh, they you know, that company has that valuation, that means the founder has that valuation because that's never the case.

Kieran O'Brien 40:00
Yeah, exactly. Yeah

Susan Sly 40:03
Kieran, I can't thank you enough again for being on Raw and Real Entrepreneurship. And I would just encourage everyone, if the show has resonated for you, tag Kieran and I on social. If it has helped you in any way, please share it on social. Let us know you're sharing it. If you have any feedback, go to I read all your comments, send them on over. And with that, Kieran, thanks again.

Susan Sly 40:26
Thanks for having me.

Susan Sly 40:28
All right. Well, ladies and gentlemen, wherever you are in the world, go rock your day. I'm sending you much love. And I will see you in the next episode of Raw and Real Entrepreneurship.

Susan Sly 40:41
Hey, this is Susan and thanks so much for listening to this episode on Raw and Real Entrepreneurship. If this episode or any episode has been helpful to you, you've gotten at least one solid tip from myself or my guests, I would love it if you would leave a five star review wherever you listen to podcasts. After you leave your review, go ahead and email Let us know where you left a review. And if I read your review on air, you could get a $50 amazon gift card and we would so appreciate it because reviews do help boost the show and get this message all over the world. If you're interested in any of the resources we discussed on the show, go to, that's where all the show notes live. And with that, go out there rock your day, God bless and I will see you in the next episode.

Susan Sly 41:34
Are you currently an employee looking to start your own business? Maybe you've been thinking about it for a while and you're just not sure where to start? Well, my course Employee to Entrepreneur combines my decades of experience as an entrepreneur with proven methods, techniques and skills to help you take that leap and start your own business. This course is self paced, Learn on Demand and comes with an incredible workbook. And that will allow you to go through this content piece by piece by piece, absorb it, take action and then go on to the next module. So check out my course on Employee to Entrepreneur.

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Susan Sly is considered a thought leader in AI, award winning entrepreneur, keynote speaker, best-selling author, and tech investor. Susan has been featured on CNN, CNBC, Fox, Lifetime, ABC Family, and quoted in Forbes Online, Marketwatch, Yahoo Finance, and more. She is the mother of four and has been working in human potential for over two decades.

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