← Our Future Podcast
Our Future Podcast
#47: How We Sold Our Bootstrapped Startup In 2 Years
00:42:17
Michael and Simmy tell their own story, nearly 50 episodes later.
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- [00:00]
A
Ordinary checking a $300 head start on checking Ordinary savings High yield savings that grow your money Ordinary Mortgage A mortgage with a rate that drops when the market does. Why settle for With Oregon State Credit Union you get all sorts of welcome to human to human banking Oregon State Credit Union insured by NCOA equal housing lender $25 minimum balance required subject to change terms and conditions Starting a business can seem like a daunting task unless you have a partner like Shopify. They have the tools you need to start and grow your business. From designing a website to marketing to selling and beyond, Shopify can help with everything you need. There's a reason millions of companies like Mattel, Heinz and Allbirds continue to trust and use them. With Shopify on your side, turn your big business idea into sign up for your $1 per month trial@shopify.com specialoffer.
- [00:59]
B
You would say the, the that I would sit there and be like, I can't believe he just said that kind of thing. And I was the, I was the more calm, kind of like logical. Like, okay, let's talk. Like, let's just be very pragmatic.
- [01:26]
C
What is going on? Our future podcast viewers. This is Michael Zakand. I am joined by my co host and co founder Simran Sandhu. And for the past roughly 50 episodes of this show, we've been covering the most successful and ambitious young people building companies that are going to change the world. And we analyze them from our perspective and give you their strategies and insights. You can use them to inform your own business, business building endeavors. But today we're mixing things up a little bit. Simi and I haven't really done an episode where we've talked about what we've done and some of you guys are probably new to the content you got throwing our stuff on the algorithm and we'd love to introduce ourselves and just tell you some of the lessons that we learned when scaling and building our media company and getting an acquisition within only a couple years of starting it to a major media company with Morning Brew. So Simi and I are scrappy. We've been in the trenches. We have an interesting history together. We knew each other long before we even started a business and yeah, we've had a bit of a ride. So we've been at our acquiring company for about a year and a half now, but there's still tons of lessons and insights that we think back on all the time and that, you know, we went through that I think you guys can learn from. So here we are mixing things up With a fresh new take on our future podcast episode.
- [02:39]
B
Yeah, and I think the biggest secret we're going to dive old here is that our first company together was not actually going to be our future. It was supposed to be a D2C beverage company called Jet. But more about that later.
- [02:52]
C
Dude, Jet Coffee could still be absolutely massive.
- [02:55]
B
We definitely got to touch on it in the show. Like someone should definitely listen to this and go run with it. I bet that could be a 7 figure, maybe even 8 figure, D2C brand in the next few years for sure.
- [03:06]
C
Yeah. But what we've learned, right, is to like in that kind of market, like distribution, retail, like you gotta either get like a big dog on board who's been in the industry for like 30, 40 years or bring on like a celebrity, like a Jake Paul or something, you know what I'm saying? So I feel like, yeah, I feel like if anything that we've learned, Simmy, it's like whatever opportunity we go after next, we need to have the right people backing us. And that's really hard when you're a first time entrepreneur. But that's kind of what we afforded ourselves with, like getting an acquisition done early on in our career. You know, we did sell early. We probably could have made more money had we continued to run the business ourselves. But we really were thinking about like the big picture. Like building a media is really hard, you know, for those who haven't started a media company, you can't really raise outside capital. The venture returns aren't there and if you are going to put money in, it's got to be your own. And we didn't have any money, so we were in an interesting situation. But we still found ways to grow and scale. And, you know, we really looked at how do we turn our future into a way bigger opportunity in the future, quite literally. And that's what we've done. So we've kind of positioned ourselves well, built a big network and have a name for ourselves. So that was a strategy in many ways, you know.
- [04:15]
B
Totally. And I think when we started out, we were just two young guys, we didn't have much money, we were still in college. And so I think a lot of what we were trying to do at that time was how do we give ourselves some cheat codes so we can win in the future. And it just felt like podcasts were the easiest way to do something like that. It was one of those things where, hey, we really want to talk and network with really important people and get our names out there. It's Covid. So why the hell not, right? And it was like one of those interesting things where, you know, we were both able to do some cool stuff with our podcast. You were interviewing big C suite executives. I was doing a daily news podcast. And that is something I would say has proved to be one of the most highest leverage activities you and I have both done up to this point. We still use the connections that we made from those shows several years later, and now we're in a much better spot to add value to those people that we were talking to. I think, you know, when we were doing our podcast, it was a little intimidating at the time because these are very important people and it's like, man, what can a 19, 20 year old, like, give them? Like, what is the value? And what I learned was that when you can give people a platform, it can be a tremendous opportunity for yourself. And more people are way more likely to do it. I think older people are just way more. They want to help younger people out. And so that was a big unlock for me mentally at that time was like, man, like, I may not have a whole lot of value to add, but it's okay. They know what they're getting into. And, you know, a lot of people have kind of the similar questions when you're doing a podcast or an interview of any kind. And so if they find an opportunity, like through a pod where they can talk to a lot of young people all at once, it actually is better for them, right? So it's. It's kind of those like, force multipliers, if you will, is just like starting a podcast or doing something where you can build your network. Early on, dude.
- [06:12]
C
The biggest thing I learned, right, like, honestly, starting a podcast or like building. Doing. Doing a podcast as a young kid and interviewing big CEOs and entrepreneurs, that feels like a very, like, kind of overused play. Now I feel like a few years after kind of, we. I feel like we were pretty early to it, but I still think there's tremendous opportunity because a lot of there are kids who go and do it, but they don't do it that well. I've seen a lot of kids go out and try it, but they don't put their heart and soul into it. They don't brand their show correctly, they don't distribute their show correctly, and they don't build the right intangibles around it. So what really made. When I decided to start a podcast, it was Covid. I was 20 years old and it was like, I'm gonna go and reach out to these people because I'm gonna seize this moment of COVID They're probably using their computer more zoom is now a thing. That's really what enabled the opportunity. Do this remote podcast. And you know, I would just paint our future, you know, the podcast as a. As around so many intangibles.
- [07:06]
B
Right.
- [07:06]
C
Like, I would say this is the business podcast for young people. I would, you know, kind of take numbers from across social channels to display the total audience size, and that's not as many listeners as they actually had on the podcast. And I would open with, you know, these, these subject lines being like, you know, the number one show for Gen Z or stuff like that. And people were receptive to it. And it's really just about the tact and the strategy you bring to it. So I still think there's tremendous potential if you're a young person to go out and try what we did. Even if it doesn't become a business, you know, it's just going to open a ton of doors for you. I mean, I was offered so many internships during those conversations when people can just see your hustle. Like, you're here, you're sitting next to someone who's worth hundreds of millions of dollars or running a huge company, and it's like, if you. You're having this conversation with me right now, you're probably made of something more.
- [07:54]
B
Yeah, I totally agree. And I would say we had different approaches on how we thought about it. I think yours was just an interesting, you know, passion driven type of opportunity around the podcast. It was just like, man, I really want to talk to these people. I think what the way I looked at it was a little bit more opportunistically, which was, hey, you know, I love what those guys out of Michigan did with Morning Brew. I think newsletters are really saturated space. No one is doing this in podcasting, so let me see if I can try to replicate it. And we had a very similar outcome in that we had exposure to really, really cool people and we learned a lot through that process. But it was like one of those funny things where by going into, like, I, I would say by, by just getting started somewhere, like, we are in a very, very different place. Like what our future was as a media company in 2020 versus where our future as a media company is in 2024 are like two totally different places.
- [08:53]
C
Yeah.
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B
Um, and funny enough, we've come full house in that we're both back on a podcast. And it just so happens that we're Doing it together this time, dude, it's all.
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C
It's all about, like, just doing something that you can, like, work on every day. I think for me, like, I wasn't technical and I wanted to be an entrepreneur, and media is an amazing place to start because you don't need technical skills or a co founder to get into it. You know, anybody can use some of these video editing platforms, tools. Riverside, like we're on right now, right? To, like, do a show like this, use email. Like, these are all technologies that were created a long time ago that anybody can leverage super easy. So I think that's a big part. But I also just want to talk about, like, how you and I were really close friends. I would say, like, just on the phone remotely, because, like, we connected over our shared interest in podcasting and we ended up being co founders in the future. And I just want to say, if you're struggling to find a co founder with whatever enterprise you're working on and, you know, you need one, think about just like, networking with other kids who have a similar idea and who are building in the same space but still feel like they want to do it themselves and. And don't make it transactional, right? Just like, build relationships and create friendships with other entrepreneurs. Because we did end up coming together and joining forces, once we figured out a little bit more of the direction of something that we could both agree on could be huge. So I think that's a good piece of advice for young people, is like, find other kids who are interested in the same thing. And maybe you don't work together from the start, but build that relationship over time and maybe you guys could join forces down the line.
- [10:16]
B
I think we were friends for almost two years before we actually started to get into business together. And I think that was tremendously helpful, not only from a standpoint of developing the relationship, but also just getting a good understanding of how you thought about things and also where my strengths and weaknesses are. Right. By the time we actually decided to work on our future together, I had a pretty good sense of where I fit into the puzzle and where I think I could add the most value. And so I think that's something that you can only do with enough time at your back. Now, I will also say is that, you know, before you, you know, get into any kind of business, you want to think hard, right about, like, what it is, what is your intended goal at the end of this. I, you know, I'm not so big on the just, like, wander aimlessly approach. I think that can work. But like, I think there is an intended goal that you have to have in mind now. How you get there will change. And, you know, it's not uncommon for folks to pivot. That even happened with the both of us, right. We were both in podcasting first and then we ended up in short form, right, because there was an opportunity that, you know, presented itself. But I think that that's really, really important, right, because, you know, you don't want to be so rigid in that you're stuck on a fixed plan. Because I think sometimes when the plan doesn't work out, you're not making any movement or progress, and sometimes it's in your own benefit to move on to that more higher leverage opportunity. But I think both you and I were from day one, dead set on, hey, we want to go build a big media company. And we both had very big ambitions on the work we were doing.
- [11:53]
C
Yeah. And we, we made it so like, you know, everything was on the table, right. We were just like super scrappy. So, you know, in like the, the earliest days, right. Like, you know, the, the ad deals started like really small, right. Like when we had, you know, we built up the short form video presence and, you know, had few tens of followers. Then it just came down to in the creator world, like the content world, right. Like, it's really just like, how about how you pitch yourself? Obviously there's like a cap to like the actual dollar amount you can charge for some of these videos on short form at that time. But it was all about, like, we always pitched our future as being like the next best thing since sliced bread. Like, we're going out. The way we cover companies is different from anybody else in the market. And we still stick to that principle when pitching people for ads, which is nobody has the storytelling capability that we do. Nobody does it like us. And as a content creator, like, you can really, like create that intangible and that like, you own the specific audience, you do things in a different way than everybody else. And I think that's a lot of other businesses can't say that a lot of other businesses have direct competitors. As a content creator, you can essentially, in media, like, you can essentially have. No, you can make it seem like there's a vacuum of competition because you're doing something in a very particular way. So I think that's just like another cheat code. Again, I think a lot of what we went through SIMI is like, we just pitched ourselves in a really big and ambitious way. And I think that's just a Huge takeaway. Because when you're young and you don't have any backing and you don't have any status or credibility, you need to be somewhat delusional and you need to be able to pitch yourself in a really big way and you need to just tell people what's up because that's how they're going to take you seriously. And there's a link to like.
- [13:35]
B
Yeah, 100% agree. Yeah, yeah. And I think, you know, take that a step further. I would say that, you know, when you're young and you're building your first company, it's not, you know, one of those things where you have to reinvent the wheel, truly find any, you know, working model or find inspiration from something that already works. I don't know, you know, if we've talked too much about this in the past, but you know, Michael, I know that like, even with some of the short form video stuff in the beginning, a lot of the inspiration for this came from what was working on TikTok, in TikTok, but in a totally different space. Right? And it was like one of those things where you were able to connect the dots, which was, hey, no one is doing this specifically for business content. Right? And so at the end of the day, it was like, hey, if this is engaging in, I don't know, finance, healthcare, you know, sports, whatever, it looks like this would also be really, really engaging in business. And here's why I believe that would be the case. And so find inspiration and it's better that you find an existing model that works rather than trying to recreate the wheel is kind of been my experience as well.
- [14:38]
C
There's a lot more risk to trying to reinvent the wheel, right? There's a lot more uncertainties if you can find a corollary for your business. That's the most important part. So just find a model that works and then apply your particular passion or interest to, you know, what, whatever that is. So I think that's just like a good tenant, right? Of that's what all the great business leaders did. Like I remember reading Sam Walton's book, like right around that same time that I found this other format that was working on TikTok and applied it. What he would do is he would just go into all these other department stores and all these other retailers and he would just study what worked and he would just combine the best parts into building his vision for what Walmart was so really like. That's why biographies exist, right? Like, you just learn from other entrepreneurs and you Take kind of the things that work for them and apply them to your own model on a slightly differentiated way. And there's plenty of space for that. There always is. Just to do something a little.
- [15:27]
B
Couldn't agree more. So, yeah, I think inspiration was important. I agree with your point about delusion. I also think you have to lean into FOMO as much as you possibly can, right? So one part of believing that you're building the next big thing that the world needs to see and experience and consume is making it so very few people have access to it, right? And so when we would go pitch advertisers, right, we would bring it, bring in this pitch around. You know, we are the brand safe destination to reach Gen Z. And we're only taking three big advertisers in this quarter, you know, to do ad deals with. And obviously that wasn't true, right? We would have taken anyone who was willing to sign a check. But it was one of those things where it's like, wait, like, okay, one, they, they say they're really big and I do think their, their style is unique. And wait, like, you know, maybe this is like really in demand and you know, like, maybe I'm hurting myself by not working with them or maybe I should at least give it a chance. And so I think, you know, you have to be really smart around this as well. And I think that also applies to fundraising too. You know, Michael and I both went down the fundraising path and we ended up not doing it, you know, thank God. It would have been a really, really bad business decision. But, you know, I think the one liner you would use in all of the closing emails was like, you know, I got one spot left in this round. Let me know if you're in. And if not, it worked pretty well. Yeah, it worked really well. But like, it wasn't like one of those things where you were begging, right? I think anytime you're you, it almost feels like you're super desperate. Like it actually turns a lot of people off. And so you want to, you want to lean into the fomo, you want to lean into the exclusivity and you want to lean into, hey, we are way bigger than what it may seem like on the surface.
- [17:16]
C
Dude, that's, I mean, FOMO is just like everybody's brain works in that same scientific way, right? So I think that's a great tenet that you could apply to anything. Whether it's like selling pre, selling fundraising, all of that is, is, is on the table. You know, when we'd reach out. You know, we started reaching out to a bunch of VCs and CEOs at Big Media companies. And so many of them responded.
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B
And these were people that you had interviewed on the podcast to bring it full circle. Like this was the existing network, I.
- [17:46]
C
Think some of them, yeah, I would reach out to. But also there was plenty of cold emails that we sent out to the CEOs of some of the biggest media companies in America, right? And they responded to this pitch because it was, it was, it was irresistible, right? It was like, we've found this new format in TikTok, this new social channel, and it's the next way, it's the next platform for building, you know, the next Vox or Vice or cnn, right? And that it was like this moment in time where even like the older people in the room were starting to hear rumors about TikTok and the, the, the hot new platform. And we were those two kids who were experimenting with it and bringing it to the big dogs, right? So being able to take, you know, what the young people are all talking about and the new hot buzzy thing and present that to someone and say, like, we are the guys who are going to go do it really commanded a lot of attention to these pitches. And, you know, we ended up getting into meetings with a lot of these folks, right? And then, you know, it's kind of like that's when kind of conversation started to change that like maybe we could actually, you know, ended up selling this business pretty quick, right? And get ourselves that stamp of approval so we could do something different in the future that we felt, you know, was more scalable and like a better business model than media because we really started to see the constraints, I want to say about winter 2023, we really started to see the constraints of what we were doing, right? Like we couldn't hire enough, we didn't have the cash flow to hire enough, like content creators and the time to go out and build organic audiences from scratch. So we were like, okay, if we can't scale the advertising side to our business, we need to find something new. And that's when getting the My First Million deal became a tenet of our business. A pillar, right? Of let's build a services business where we take our expertise and the business world and short form video and apply that to companies that have an interest in that. And the story goes is that Sam and Sean on the My First Million podcast, we've modeled our show a lot on what they've done, but they were looking for somebody to take them viral on TikTok because it was like that hot channel that they didn't know about and they needed a young killer to go do it. I mean, who better equipped than us? So ended up winning that competition. Just pure meritocracy. We want it. And ended up parlaying that into our deal with HubSpot, which is now one of our biggest clients, continuing to be across all their short form video for their podcast networks. And then that opened the door to all these other B2B software companies we now work with today. I mean it's countless. So for anyone who doesn't know, right, like our future is in many ways a media company that's disguised as an agency. You know, we found an alternative revenue source and we're able to use an unfair advantage and being a massive media company and connecting those two and I think that's a way that a lot of media companies end up making money is through like kind of services. Business side, totally.
- [20:35]
B
I think we really benefited ourselves by staying open to the business model itself. We weren't really, you know, fixated on this has to be an advertising driven business model only. And so when that opportunity presented itself, we actually found ourselves in a much better spot. And so, you know, it actually has last. It actually has left me with a very long lasting impression which is a lot of business success is driven around creativity, around the business model itself. And so, you know, in again like surface value, it's like, okay, you got services, you got ads, like what's so unique about that? But like when we sold, that was a really, really big deal. There wasn't, you know, this hybrid agency slash media company of sorts that was doing the way the things we were doing at that time. And it was really unique and it made us really, really appealing, especially to a lot of the people we were trying to, you know, talk to around like potentially selling or have them invest in the business.
- [21:35]
C
Because we solved for the, we solved for the challenges in advertising businesses, right, which is, you know, you can have a dollar fifty grand one month and then zero dollars the next month just because of how the ad market works. So we were able to build repeatable recurring revenue, right. Which is really what enabled our business to be able to stand on its own. And for you and I to go and pay ourselves salaries and for us to have cash flows to hire and, and grow and expand, right? So it was those two sides of the business, me leading the media side, you leading the agency side, that really enabled our future to become a multifaceted business that was much more appealing to an acquirer, right? Because we had stable recurring revenues. And that's why I just think media companies are so hard to sell, right? Because the business model is inconsistent when it's just advertising focused. And the biggest thing I learned is just like, ads are not a meritocracy. It's like years of relationship building, brand building, to be able to secure these placements. You know what I mean? It's just not. Not a meritocracy. I mean, you can't just apply because you have this many views and just get the equivalent ad dollars.
- [22:34]
B
Recurring revenue is such a beautiful thing. And I think, you know, especially in 2024, it feels like everybody has woken up to this and everyone's kind of trying to build some services arbitrage. But it was kind of the value of being early to a specific, you know, area or opportunity. I would say, like at the time, no one was thinking about services kind of in this way, which was, hey, you know, we have a working format here. If we license this out to other big companies who have very deep pockets, that could be really, really interesting. And we did it in kind of a creative way, because I think a big factor in those conversations at the time is like, hey, if we give, you know, this editing prowess or, you know, our editors to these companies, does it dilute our brand? And the answer being it was no, because we were very strategic on what we were licensing. You know, we weren't giving them the playbook. We would come up with something really bespoke and unique for them. And so it actually made us somewhat defensible because I think if we had gone into every single company with the same cookie cutter strategy, it would have been way easier to replace us and, you know, find some other agency who could undercut us in price and then they would be working with them instead. But it was like, no, Every single offer is so unique. Now granted, that does present scalability challenges of its own if you don't have something that is kind of like very templatized. But I would also say that for where we were at in our business at that time, it was really emboat for us. Something else that I thought was really cool was just when you would go into these meetings, we had a very different dynamic. And I think, you know, we played this like good cop, bad cop strategy, although I don't know if it was intentional per se, was just like having very different. Having very different personalities, which was, you were the more bold one out of the two of us, and you would Say the, the shit that I would sit there and be like, I can't believe he just said that kind of thing. And I was the. I was the more calm, kind of, like, logical, like, okay, let's talk. Like, let's just be very pragmatic here. And I actually think that really helped us with investor conversations and acquisition conversations, because, you know, I think this is a good segue into how the Morning Brew opportunity came about. And so, you know, Austin, Alex, both of those guys had gone to Michigan and Michael had as well. And, you know, we had this opportunity to go to Austin and try to, you know, try to persuade him to invest in leading our round. And Michael, tell me if I'm wrong, but the conversation was essentially like, hey, we're trying to build, you know, the barstool business we're going to crush. We're already doing so, so well. Would you want to lead our round? And Austin saying, hey, you know, this is interesting, but I would rather buy you guys. And it was the confidence in, you know, maybe even the delusion that you're referring to where you would. You were. Where you were essentially just like, no, I'm not going to sell. And I think it was one of those, like, defining moments by saying, no, we're not looking for a way out. They only wanted to buy us more. And so I think, you know, same thing about the FOMO thing. When an opportunity does present itself, don't just act like, you know, act like you've been there before. Like, I, you know, someone raises a small round and it's like, oh, my gosh, you think they would have taken the company public, by the way? They're, they're like, you know, going crazy about this. And it's like, no, you just have to own it.
- [26:00]
C
You really have to have that confidence. And, like, you can't let anybody get the hint that you don't. I also want to talk about, though, like, it did take us a. A long time to close the deal with Morning Brewing from while we were still building our business. And I just think, like, the. The build to acquisition strategy is, like, really unpredictable because it. Once you have acquirers talking to you, like, it can pollute your mind so that you stop growing your business and you're just focused on getting that deal done. But, like, deals don't go through. Like, you know, they fall through. Most deals fall through. So, you know, it's just. It can. It can poison and pollute. And I think you and I, we did actually lose a little steam on, like, our vision and our mission while we were having those talks. So, you know, I would just advise when anybody ever comes to me and they're like, somebody just mentioned, like, they might want to buy my business. I'm just like, brush it off, man. Like, it's probably not true, but see it through. I mean, try your best, but, like, don't let it get to your head. And I think that's one of the big lessons from. From what we did is. Is, you know, just not getting caught up in that idea of, like, oh, soon enough we're going to have our business sold. It's like, it's going to take time. The odds of it closing are very low. So just continuing to build your business and do your thing, I think, is, like, the most important part.
- [27:15]
B
Yeah, I think we definitely did try to preserve optionality as much as we can, and that was ultimately the reason why we chose not to go the fundraising route, which was, hey, we don't want anyone telling us what we need to do and be stuck on these arbitrary deadlines of sorts. We want to build the business we think makes the most sense. And I think going back to the acquisition thing, it was one of those things as well. Like, we never shut the door on any of the conversations. We were actually entertaining, you know, multiple offers and opportunities all at the same time. You know, we never necessarily told anybody to kick rocks, but we weren't begging for an offer either. And so I think that was one of those things where, you know, we didn't really know what we wanted out of them, per se, but we were just, like, trying to get the highest bidder and we were, like, trying to get them to make the next step. And, you know, we were like, we were a little bit in our heads too much as well. We were like, wait, should we send this email? Should we follow up now? Like, what is the. What would, like, the bold person do in this play, but, like, also still be respectful and, like, not piss them off too much and not feel like we're super anxious about it. And I think, like, going back. Yeah, yeah.
- [28:21]
C
I just want to mention, like, the importance of getting to the decision maker. A lot of deals are caught up.
- [28:25]
B
That's what I was about to say.
- [28:26]
C
Yeah. Between the decision maker, like, and you guys, and we got caught up in a lot of conversations with the middleman, and I think the best way to see if a deal is going to happen is to look at, in the decision maker's eyes, think if they really want to do this or not. And if the decision maker doesn't follow up with you and isn't being receptive, they probably don't want to do the deal. So I think that's just a great principle. Make sure that you're talking to the decision maker when it comes to actually getting bought or getting an investment or whatever. Don't get caught with some analyst or middleman and you know, just understand that, you know, the decision maker is the one you need to analyze and observe and to really figure out if this deal is going to go through.
- [29:08]
B
I totally agree. And I think the way to do that is by just having the discussion very early on, which is, hey, who all needs to be involved when approving this deal or saying, rejecting it? Like you need to figure out who the key people are very early on in that discussion. Because like, if you get stuck behind the person who doesn't really have authority and they may have their own, you know, incentives or agenda that they're driving, it can be a really, really tough spot to try to navigate because like, then you can't go over their head and you know, that can kill the whole entire thing. And so you just have to be really, really careful. I would also say don't leave anything up for assumption. When you do decide to go down that, that path of, you know, trying to get your company sold, right. Even though it may make strategic sense for the company that is buying yours to do what you think they should, make sure you verify that they will do those things. Like get it in writing before you actually sign any, you know, sign the dotted line like in. It may be one of those things where it just feels uncomfortable because it's like, man, this should really feel intuitive and this just makes a lot of sense. But like you don't want to be in a spot after the deal happens where you're like, man, I really like feel like, I don't know, you get cheated here because it's like this thing that I wanted to have happen didn't happen. So make sure like have those uncomfortable discussion discussions up front. I would probably even say like, you know, you want, you kind of want to save your time. Like if a deal isn't going to happen, you might as well like, you know, try to try to crush the deal as quick as you possibly can. You know, ask those tough questions, do, do your due diligence and like, you know, be bold in the very, very beginning so that like, you know, all of the follow up discussions are just on the one or two things that are really, really important. Right? Because if you think about these like deals, just more broadly speaking, there may be 20 points, but 18 of those points do not really matter. It's one or two points that like, are really, really critical for both sides in the party. Figure those out as quickly as you possibly can and make a decision. Right? You don't want to compromise. There's. And then you just have to be really, really strategic, right? So in this scenario, if you have 20 points that you know you're negotiating on, don't just give up all 18 in the very first meeting or two meetings and just say like, yeah, that doesn't really, really matter to me. Yeah, I'm willing to negotiate there. Like you still want to play hardball a little bit, right? So be strategic on what you're willing to negotiate on. But deep down know that these are two things that like, are absolute non starters. You're not going to move there. They are deal critical factors.
- [31:50]
C
Yeah, I think those few critical points are really important, right? Like the money is the money and the deal is the deal. But like what happens after and like what happens with your business after? Super important. I remember we were very intent on like we are going to be doing a podcast with the Morning Brew no matter what happens here. And like we made that very clear that that's what we needed if we were going to go do this and they ended up giving it to us, right? So that I think things like that are like key, right? Like, and it's been awesome. Like we've got to meet so many people and not like this show's huge at all, but it just, we've gotten to meet so many people, we've gotten deals through this. Like it makes us more relevant. So like just getting those, getting those like cherries on the top of the Sunday when it comes to the deal, I think is really important if they're really like non negotiables to you. And for us, getting acquired by Morning Brew is in many ways a way to expand our personal brands and expand our platforms, like personally. So that's exactly why we're able to go and do this. And we're, you know, really grateful we were able to get that through.
- [32:44]
B
So I would also say that when we were talking to potential acquirers, it was one of those things where they were very hyper personalized pitches and conversations. So we would do the prep work beforehand to say, hey, this is how we will fit into your organization and this is a key problem that you're facing and here is exactly how we solve this for you. I think if you can remove that step and show your value in like the first five minutes of your call. They know you're very serious characters and it's like, you know, they're excited to take the conversation forward because it's not one of those like, oh, these are just, you know, two young guys looking to make a lot of money. It's like, no, they've deeply tried to understand our business and they're trying to add value. It's a, it's a kind of a very value add mindset to have. And I think that especially with, you know, the enterprise companies we were talking to didn't end up doing a deal with like I could notice a day and night difference versus, you know, when we would bring up those details versus like, you know, just having a more just like informal conversation and like you're just shooting the and trying to get to know each other but you're not really making progress.
- [33:52]
C
You know, again, like, I think there were some big parts to this which are, you know, find someone with complementary skill set and interest in the same industry. Find the new medium, the new arena that like is making sense for the space and that everyone's kind of looking at create intangibles, be able to pitch yourself bigger than anybody else. Right. Bring that pitch to the right people and you know, think really intentionally about the acquisition process and think mainly that it's not going to happen.
- [34:20]
B
You know, I think I got a few other things that just came to mind and we can do this almost rapid fire. Like so, you know, give me your take on these. But one, I think around the topic of competition. Yes, be aware of your competitors and know what they're doing that is unique. But, but do not like change your strategy based on what a competitor is doing. And I think this is something that like, you know, was a great lesson to have early on but like also did hurt us a lot which was like we were hyper focused at like what the competing agencies and competing, you know, short form media companies in the business space were doing. When I now look at it like the look at the space three years later, most of them do not exist. And it's like one of those funny things where it's like, you know, at the end of the day one or two will remain, the rest will fizzle out. So I'm curious to get your take on it.
- [35:10]
C
Yeah, I think you have to dance to your own drum. You know what I mean? I think we always were doing something a bit unique. But yeah, I mean we were just, I think like it's just, my advice is just pretend competition doesn't exist. Pitch yourself like competition doesn't exist. Be the only person doing what you're doing. Because you're describing it like that there might be other people who are kind of doing something similar, but like, you were the only person who's doing this and believe that deep down, I think that's like the biggest piece of advice I can give is just to believe it. Even if there are competitors, just believe you're the only one and bring that energy, confidence to other people.
- [35:42]
B
Yeah, 100%. And I think when you are pitching yourself and you find a really unique framing or unique positioning, you know, what's great about it is you get to create the rules, right? And so we were saying we were the only brand safe destination for, you know, advertisers to reach, you know, the business Gen Z audience. And what that meant is really we could command our own prices, right? And so we just kept raising our prices until we said, well, until we heard no. Until it got to the point where it's like, okay, we are consistently hearing no because the pricing is too high. We just kept going up and up and up. And so I think that is kind of the value in finding unique positioning is like you get to define the rules. And I think even in more broad, even more broadly speaking, even if you are in a more commoditized industry or there's a lot of businesses doing what you're doing, use other businesses. And I know this kind of feels a little counterintuitive to the competition aspect, but figure out what the incumbents are charging and, you know, use that as a benchmark for your own pricing. Because I think that is one of the hardest things for people, young people especially, to nail early on is like, how much do we sell this for? And like, what all are they going to get? So I think, you know, use what exists and then try to find your own tweak or find your own flair so you can create your own rules. And the last thing I would say is be very careful of whose advice you take. And this feels like, again, one of those things where you don't want it to deter your strategy, right? You know your business better than other people do. And man, there were like 20 different occasions I can think of where we were almost about to do the wrong thing because some very successful person or some very, like, creative person told us we should be doing it, bro.
- [37:30]
C
It's crazy. You know, like, Bobby Axelrod has that line. It's like, you know, when you're rich. Like you're kind of like when you walk into a room, you know what everyone wants. I think it's also like as a, as a startup founder with a good idea and a little bit of traction, you're also a hot commodity to others to puppeteer.
- [37:44]
B
Right.
- [37:45]
C
Like we had people being like, yo, you guys need to go raise hundreds of millions. We're going to take you public. On the Canadian stock exchange. We had people being like, you guys should just stay bootstrapped and continue to do this and like build out kind of like a barstool model with like fractional ownership. I nearly turned our future into a crypto business media company because I was looking at the NFT space and how much money was to be made there. Imagine where we would have been right after the crash happened in the summer before we ended up selling. So damn, there's a lot. They're going to pull you in every single direction. Especially if you got a little bit of success, they're gonna want to, you know, kind of remote control you and, and do what benefits them, which in many ways is like them getting to invest and then them bringing the strategy out or them getting to work with you in some capacity. Right? So everybody's playing their own agenda. Nobody's giving you advice as an entrepreneur and out of your self good, right? Like there are mentors, you can have like that and people have those mentors, we have those mentors. But there are people who are on the outskirts that are looking in the inside and figuring out what they can make of the situation that you are in the driver's seat of. And they're going to want to be your passenger, showing you the map of where you need to go. And you want to set your own navigation address. You want to set, you want to use Apple maps yourself. You don't want anyone setting that for you.
- [39:00]
B
So true man. I mean you got to figure out like what their incentives are because you know, it's like one of those things where to your point, you know, they have their own personalized agendas, but also like, you know, it's kind of like the whole hammer and nail thing which is if you're talking to venture backed people, they're going to encourage you to go raise money. That's what they know. If you're talking to bootstrap people, they're going to tell you to bootstrap. That's what they know. If you're talking to, you know, some other business mix, right? Like they're just going to tell you what to do based on their own experiences. And honestly, like, this is where talking to like, maybe really, really successful people who built and sold companies, I don't know, 10 years ago, 15 years ago, isn't so helpful because the business conditions in the business environment is so, so different. Right. If you're trying to build a big services business now, you would have to use an entirely different playbook versus like the 2010s. And so just be careful about like, who is giving you this advice, what their experience was themselves and like, what the general, you know, business conditions are. Because what worked for them at that point is not going to work for you in, you know, the current timing and the current business that you're trying build.
- [40:12]
C
Absolutely, man. I mean, again, use those other businesses as like, analogous to yours as examples. Right? But then you have to figure out in this present moment, what wave can I ride and do something similar, but not exactly the same. Because if we had tried to build the morning brew, we wouldn't have been able to at that time. Right. Like, I don't think people could build the morning brew again just because of how expensive ad dollars are and like how saturated the newsletter space is. So it's got to be a new arena and then you can use that business as a corollary and then that business might become the ideal acquirer. So that's kind of how we thought about things and the business we always admired the most became the business that bought us and now, you know, we get to work for them and continue to build this business underneath. So really a full circle story and one that I'm very proud of and one that gives me a lot of confidence and excitement for the future of what you and I can both do with our careers and one that I think more, more young people I hope can learn from.
- [41:03]
B
Yeah, and I mean, there's so many other things we can touch on. I mean, like, we only have so much time here, but if you have any specific questions or are curious about, like very, you know, specific topics, we're happy to make a part two to this video. So let us know in the comments. You know, hit us on, on our socials. I, I think our info should be in the show notes per usual. But you know, we want to be a resource to all of you guys trying to build your companies and want to add value to you. So. Yeah, I mean, we're open bucks. Ask us, ask us, whatever.
- [41:34]
C
Yeah. And thank you to those of you who've added comments and have watched these videos. Like, we're super grateful for your support. It's humbling that we have pretty much anybody watching us, to be honest. So thank you for everything and we'll make sure to keep liking and responding to comments. But yeah, specific questions we'd love and any ways that we can help and provide a piece of advice. I think we owe it to the next generation as Gen Z entrepreneurs. So thank you everybody. Make sure to be subscribed and continue to watch the content. You know, we're continuing to put out these episodes and continuing to study amazing founders, so this was a fresh change and hope you guys enjoyed as always. Stay frosty and me and the boy will be with you soon.
- [42:15]
B
Stay frosty.