What We Would Gamble On

Neil and Eric break down smart bets from a work and investment perspective, why crypto still has upside potential, and why hiring great people only works at the right stage of business. They share real numbers behind outbound email, gift card incentives, and ROI, then unpack the biggest marketing wins and losses of 2025. The episode wraps with how podcasts actually make millions through ads, brand trust, and backend conversions, plus lessons from growing agencies, software, and global marketing strategies. Key Takeaways • Crypto and self-investment beat most external bets • Lead quality matters more than lead volume • Podcasts drive millions beyond ad revenue Chapters (00:00) Work and investment gambles (00:14) Crypto vs people investments (01:15) Hiring timing mistakes (03:14) Best investments in business (04:01) Biggest marketing wins 2025 (05:45) Outbound email ROI breakdown (10:38) Biggest marketing losses (14:44) How podcasts make millions

• 0:00Speaker 00

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• 0:41Speaker 01

  I gamble from a work perspective?

• 0:43Speaker 00

  Investment standpoint. So you and I kind of joked around Solana, right? What would be that?

• 0:48Speaker 01

  Yeah, this is not financial advice, but I would probably bet on more crypto, or crypto, whatever you want to end up calling it. Other than that,

• 1:00Speaker 01

  I would invest more in just doubling down on really good people. Like, if I had, you know, extra $10 million a year for three years, I would go hire $10 million worth of amazing-

• 1:13Speaker 00

  That's not a gamble, dude. You kind of know it's gonna work or not work quickly, you can cut it.

• 1:17Speaker 01

  No, but dude, I've hired a lot of amazing people, and it usually doesn't work the way I think in most cases, or people will tell me. Hiring amazing people helps a business grow. Yes, he has a lot of books. He's smart. He reads a lot. Unlike daddy. Daddy doesn't read enough.

• 1:34Speaker 00

  No, I don't.

• 1:35Speaker 02

  I read a lot.

• 1:36Speaker 01

  Okay, so when I've hired amazing people in the past, what I've found is they typically don't produce the results as quick as I want, and some don't produce the results at all. And what I found is it's not just about hiring amazing people. It's about hiring amazing people at the right time. Sometimes a business isn't ready for it, and I'll give you an example of this. So I was talking to my CEO, my G. And he was talking about one of his buddies. And his buddies are interviewing, he's interviewing at other agencies. I was like, man, I know you talked about having him for a global role. And we have so many global clients in different countries. Working on cross-selling and then, you know, bridging accounts from country to country.

• 2:20Speaker 01

  You know, division to division and it would help with the land and expand. He's like, great idea. He would be great for that role. He's just like, we're a year to two years away from really needing it. He's like, we have global accounts, but they're not big enough global accounts. And they're going to be harder to land and expand. I'm like, what do you mean? He's like, that role is really effective when you can generate a lot of eight-figure accounts. He's like, for seven-figure accounts, it's not as effective. For eight-figure accounts, you can really balloon them up and make a massive ROI from it. And he's like, if you look at us, he's like, we get seven-figure accounts. But he's like, it's not like every day that we're getting eight-figure accounts knocking on our door.

• 3:03Speaker 01

  And he was just saying, wait till year ten, where we just finished year eight this year. So I was like, cool. So great candidate. If I hired him, it would be a waste of money. That's why I say if I had ten million dollars for like three years straight, I would make a ton of hires and just be patient.

• 3:18Speaker 00

  Yeah. So what I would say to that, um, one, I, this might maybe practical for people, but I, I actually have a note, an Apple note on, um, who to hire. And, you know, also for when, right? Because sometimes it's two, three years out. Or so. Sometimes I, I continue to talk to someone. It's, it's, it's like three years or so. Um, now to that point, I still look at it as us making us an investment. You never know with people, like you're lucky if you get it right. I don't know, fifty, seventy percent of the time. I actually did the math on ours. We have a seventy percent success rate in the last twelve months. Um, but all that to say is, is I think the best investment, not financial advice, at least for us, is to plow it back into our own businesses. That's why I don't look at it as a major gamble because we're betting on ourselves. But if we're to gamble, again, not financial advice, we'd probably be messing around with crypto right now. Um, something that's maybe not altcoin crazy, but maybe like a little,

• 4:02Speaker 00

  that's kind of up the stack like a Zalana, for example, that has more room to run. Uh, but anyway, that's just me and just Neil and I just kind of messing around with crypto. Um, so we have another one here. How about best, biggest marketing win for twenty twenty five?

• 4:16Speaker 01

  My biggest marketing win, I would have to say, is doing, and we were doing this in two thousand and twenty four and even in two thousand and twenty three, but we ramped it up more and more. Has been doing in-person meetups, uh, where we handpick the right type of enterprise companies and we give speeches to them in different countries. So there may be like twenty, thirty, sixty, whatever people in a room. And we'll give speeches and build relationships. That generates a lot of revenue for us in the long run. Uh, if I look at my leads year over year, it's funny because I got a message from Sal who heads up marketing and he's like, dude, we need to run more ads, leads are down. And I'm like, you're just looking at a total count.

• 4:57Speaker 01

  Let's say leads are down thirty percent. I don't know what the number is. And, and then I was breaking down, uh, I asked him the question, like, do you know the RFP numbers in two thousand and twenty three, just in the United States? He's like sixteen, seventeen. I was like sixteen. That's right. And he, I was like, what about two thousand and twenty four? He was like, we got a fifty percent increase. It's like a little bit more, twenty five. And then he's like, okay, I'm like, what are we at for two thousand and twenty five? And he's just like, thirty eight? The last time I checked, maybe thirty nine now. I was like, we actually hit forty. So I was just like, maybe we'll get forty one before the year ends, but I doubt it now because we only have around, call it eleven-ish days, uh, before the year ends. But when you look at the RFP count,

• 5:37Speaker 01

  those are the right type of leads and more of our RFPs are larger in size, they're more services and they're more regions where they need help in. So it's like, yes, you're looking at total leads, but you're not looking at the type of leads we ideally want. Because if you look at the ideal type of leads we want, it's actually up drastically, uh, globally.

• 5:58Speaker 00

  Yep. I would say for us, it's outbound email. And what I mean by this is, um, we work with a company called Sales Automation System. So they, they did a great job, but we decided to kind of take it, uh, take it in-house. Um, more so my sales team wanted to take it in-house. Yeah.

• 6:11Speaker 01

  And you, because that means you think you could do it better.

• 6:13Speaker 00

  Well, I mean. The reason, and I'll give kind of my reasoning for this and maybe some of them will listen to this. But the reason I set it up, set us up with sales automation systems, they actually take a commission. And I knew that tax would be so irritating to my sales team. But I wanted to get it going because I've been talking about outbound for a while, but we, we, we weren't really getting much movement there. I was like, okay, I'm going to go with them. We're going to place a tax on your commissions. So you're just like, screw that, right? And then now what's happened to their credit, to the sales team's credit now, um, we're, we're taking it in-house. And, um, you know, it's because what sales automation systems does is it's great. It's, it's, it's very, um, I think we probably hit three or 400,000, sent four, three or 400,000 emails. I think we got 200, I want to say 200 or 250 responses from it.

• 6:57Speaker 00

  And we actually, I think we closed, um, maybe three deals from it. And these are all ICP fit. These are because we're targeting more B two B, especially B two B SaaS. Um, and so we, we, that's what I would say, like, they were very good at staying on top of the different, um, offers. In addition, like, I'll tell you what worked. The 105, not $100, but $105 Amazon gift cards. That still gets people to respond because you know, show me instead of, I'll show you the outcome, right? So, yeah, I, I, I've been surprised because in, in the past, I've tried to make outbound work and it just never worked. So, uh, credit to sales automation systems. If you guys want to try it first, I would certainly recommend it. Because they've done great for a lot of companies. Go ahead.

• 7:33Speaker 01

  What, what was your deal? Okay, so you ended up sending out Amazon gift cards to potential email, uh, potential customers. So sales automation systems or whoever you're using now internally. You would go pull a list together of ideal companies. I'm assuming you're doing account-based marketing. You would then target the specific individual and you would, you know, start giving them offers and stuff like that. Like free Chipotle or Amazon gift cards. I'm assuming you tried a hundred dollars and you know, a hundred dollars doesn't work. So hence you said 105 is better.

• 8:03Speaker 00

  More so 100 still works, but because so many people are doing it now, you want to stand out a little differently, right? So some people will send AirPods, like I know of a B two B agency that actually sends AirPods. Um, I'd rather just give them the money. And we do the gift card, plus we try it with different offers. One might be for carrot, one might be for click flow, one might just be for.

• 8:20Speaker 01

  You're, you're giving them an Amazon gift card in exchange for what?

• 8:23Speaker 00

  To get on a call with us.

• 8:24Speaker 01

  Okay. And then for every phone call that you do, how many end up signing up?

• 8:30Speaker 00

  Yeah, so the only numbers I have for you is we've closed three and this is like we started with them three, four months ago or so. Um, and then two hundred fifty people responded, um, three closed.

• 8:39Speaker 01

  So three out of two fifty, which means you still have more in the pipe. At two fifty, you sent a hundred and five dollars, so twenty six thousand, two hundred and fifty dollars in gift cards. Right? I'm assuming that sounds right. Uh, and out of the twenty six thousand, two hundred fifty, you're also paying sales automation system. So how much?

• 8:56Speaker 00

  No, no, no, sorry, sorry, sorry. So two fifty replied, but it's a certain percentage of them that got on the call. I just don't have that number right now. Yeah.

• 9:03Speaker 01

  And you close, so you didn't have to give all of them a gift?

• 9:05Speaker 00

  No, so let's just cut it in half. Let's just say thirteen thousand dollars in gift card spend.

• 9:09Speaker 01

  Okay, so thirteen thousand, you closed three deals. What was the total contract value of the three deals?

• 9:14Speaker 00

  I couldn't tell you off the top of my head. I can say each deal averages, let's just just say each deal averages around twenty grand to start.

• 9:22Speaker 01

  Per month or one time?

• 9:23Speaker 00

  Per month.

• 9:24Speaker 01

  Okay, so you you close, call it, you know, three hundred, uh, seven hundred or what is it called? I don't know. My math's bad today.

• 9:32Speaker 00

  It's okay.

• 9:32Speaker 01

  Eighty, seven twenty? You close seven hundred and twenty thousand in revenue, cost thirteen grand, and then you had to pay sales automation?

• 9:39Speaker 00

  Let's let's throw another twenty thousand on top for our sales automation systems. So say we paid thirty three grand or something like that.

• 9:45Speaker 01

  And they closed it or do they pass it off to your team?

• 9:48Speaker 00

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• 10:24Speaker 01

  So you have to pay double commissions to your team and sales automation.

• 10:28Speaker 00

  Correct, and that's the tax that my my sales team didn't like. Yeah.

• 10:31Speaker 01

  Cause they get paid less commission.

• 10:32Speaker 00

  And my my, yeah, exactly, right. But again, I I knew that would apply pressure to really get it going. Once it really starts to hurt, right? Um, but what I would say is I I again, I believe it's we closed, we closed three deals and um, I do know the the number, the amount that we paid to thirty three grand, that is in fact accurate. So, yeah.

• 10:48Speaker 01

  Thirty three thousand dollars. Okay. And then plus internal commission. So it's worth it.

• 10:53Speaker 00

  Yeah, it's worth it. And then now it's like, okay, how do we just ramp into how do we just micromanage this process more? Um, because you're you're constantly having to test different offers and you're constantly having to re-warm email boxes and things like that. Um, so output works. Cause what's interesting to me, Neil, is when I see some of the responses, because the responses come through Slack, I'm I'm staring at them. I'm like, oh, like, a lot of people are like, oh, yeah, our strategy is actually changing this year. We'd love to talk right now. Our strategy is changing this year. So sometimes it's not even about the gift card. Sometimes it's just uh hitting people at the right time, because ninety nine percent of people aren't ready to buy in market typically.

• 11:25Speaker 01

  Yeah, that makes sense.

• 11:26Speaker 00

  Yeah, okay. Now let's switch over to biggest marketing loss. I'll start first on this one and you you can go next. Um, I think our biggest marketing loss this year was actually on the the carrot side of things. And what I mean by that, so carrot's my my LinkedIn account based marketing product, which still gets leads and still gets customers, by the way. Um, but it's a very niche, uh, it's a very niche feature. And what's interesting to me, Neil, is I've actually talked to a handful of people at competitors recently, um, who have worked at similar type of companies. And they've all they've all since less left those companies. And they said that it's just really hard to sell in that niche. Um, and that's why those companies aren't growing that much. And so had we done more, had I been, I think, more involved with customer development in in the beginning, I think we would have gotten to that insight faster.

• 12:09Speaker 00

  Um, so I would say that biggest marketing loss is not doing enough customer development, because it we still have a great product, um, but I would say it's more of a niche feature than it like a full fledged product.

• 12:19Speaker 01

  Yeah, I would say my biggest marketing loss for twenty twenty five. Is um it's a toss up between two. The one for the agency would be, we didn't do enough local marketing. Like in countries like Italy and Germany and places like that to make it well known. Um and when I say didn't do enough marketing, we had boots on the ground. But a lot of the events that were had our ideal customers in those regions weren't willing to pay me. To speak and they're used to charging uh speakers. And uh like to Mexico and stuff and we should have done it. Um you can pick a lot, pick up a lot of great customers from these events. They charge everyone. I I really do believe we should have done it. Um I would say that was a big mistake on.

• 13:05Speaker 01

  My end in twenty twenty five, but uh we're gonna change that in twenty twenty six and we're gonna try paying to speak. I've never done that before. We usually always get paid. Not, I'm not talking about airfare and you know, uh hotel. I'm talking about airfare, hotel and money. So it's gonna be a total one eighty where I had to pay my own airfare. My own hotel and paid to be on stage, right? So I'm curious to see how that goes.

• 13:26Speaker 00

  But but it's good, it's good that you're you you have such high ego where you're just like, oh, I'm not gonna do that. So whatever works for the business.

• 13:32Speaker 01

  Yeah, whatever works for the business. Um my I my in a dream world, I wish it was. We could pay to speak and it wasn't me who was on stage and someone else could speak and it would. Perform just as well. I'm not saying that I'm the best speaker or anything like that. Uh but if it performed as well, I'd be so excited because then I wouldn't ever have to travel to speak and other people can do it for me. We do have some amazing speakers, uh just we don't have amazing speaker for every single country. Um and on the software side, I would say. One of the biggest marketing losses was. We didn't invest in product, you know, I had so many calls with my team this year on marketing. And the people running marketing and software, they're like. We're losing traffic on some of these softwares. We need to run ads more competitive. And I'm like, guys.

• 14:17Speaker 01

  Software, marketing works very different. If you have amazing product, you just get more popular without doing tons of marketing because we already have a big enough base. If your product sucks and it's not keeping up with the Joneses and everyone else at the competition, you're gonna lose traction and you're gonna lose visitors over time. And I'm like, what you need to do is not spend as much money on ads and marketing. What you need to do is take that money and just create more products and release them for free. And it creates a better flywheel from a marketing standpoint than it does to go and run paid ads, at least for software.

• 14:49Speaker 00

  You know what, one of our, I'm talking about both of us, our biggest loss this year is not having someone on top of our podcast, the, the work that we do on the advertising side. Because there's a lot of good advertisers and I wish we just had someone to kind of man it, um, but we don't. And finally, we're getting some deals through, but it has to be you and I kind of doing the, the dirty work, which is fine, um, but I wish we just did something, um, sooner about it.

• 15:12Speaker 01

  Yeah.

• 15:13Speaker 00

  Yeah. Okay. So final two here and then we can move on to some of the topics, the other topics we have.

• 15:22Speaker 00

  No, I, I think that might be it. Is there anything you want to add to this one before I continue?

• 15:26Speaker 01

  Go for it.

• 15:27Speaker 00

  Okay. So, did you see, I, I mean, okay, this is a good topic for us to talk about. So the topic here is how to make millions from podcasting. So there's a good, good couple of examples here. So Acquired FM, they charge, I think, two million dollars for, per quarter for it to own like the midroll, or maybe two point five million dollars to be the primary sponsor. Yeah, that's a lot of money. And, uh, Lenny's podcast, so Lenny's podcast was, used to be more of a product podcast, but it gets a lot of, uh, a lot of downloads now. And he sells mostly ads to, um, companies like, I don't, I don't know, there's a lot of tech companies that you, like Notion, for example. The Founder's Podcast is sponsored by, uh, Colossus, which is, uh, they have to invest like the best podcast. Um, I think these, these, these ear balls, not ear balls, but these earlobes, these, these ears are very valuable ears.

• 16:12Speaker 00

  Just because of the, the caliber of people that you're listening to and acquired, the, the reason I even came up with this topic on how to make millions from podcasting is because the, the found, one of the co-founders of the acquired podcast, like, I don't know why more people don't copy our long form way of, of doing these business analyses. Um, I would even argue, Neil. That our, our podcast, like, we have done well with advertising in the past on this podcast. Um, I would say that I see this podcast as a touch point. I don't think it's the last touch point when it comes to driving conversions. But at least for our sales team, they say 60% of people know of, of us because of the podcast or because of YouTube or because of something else. And so I do, I do believe this is a very valuable touch point because I'll tell you what, Neil, one little last thing.

• 16:54Speaker 00

  I got so many messages. I don't know if you did, but I think I got 10 messages in the last day or two. Cause we, um, our feed was messed up on Apple and so many people were messaging saying, hey, I listen to your stuff all the time. Hey, this is, hey, it's not working. It's not working. It's not working. So I know we're doing something great here and I know for a fact that we've actually driven millions from this podcast, not just from advertising, but, um, on the, on the actual customer side.

• 17:15Speaker 01

  I don't think I got one message.

• 17:17Speaker 00

  Maybe because they know you won't respond.

• 17:20Speaker 01

  I try to respond. It's also people that can't find, well, my email's not that hard to find, but a lot of people.

• 17:25Speaker 00

  You don't check your LinkedIn messages or your Instagram messages, right?

• 17:28Speaker 01

  I actually check Instagram messages.

• 17:30Speaker 00

  Yeah, but not, not from general people, right?

• 17:32Speaker 01

  I do. I check all of them.

• 17:33Speaker 00

  You do?

• 17:33Speaker 01

  I get a lot of leads. I get probably three to four leads a day on Instagram.

• 17:37Speaker 00

  Really?

• 17:37Speaker 01

  Uh huh.

• 17:38Speaker 00

  Wow, that's a lot.

• 17:39Speaker 01

  I have my phone right now. I'd pull it up, but my daughter took my phone.

• 17:41Speaker 00

  I believe you. I believe you.

• 17:43Speaker 01

  And like, they'll tell me budget and everything, like no joke, three to four leads a day.

• 17:47Speaker 00

  Were you asking the budget yourself?

• 17:49Speaker 01

  Uh.

• 17:50Speaker 00

  Are your teams managing your Instagram?

• 17:51Speaker 01

  A lot of people have my Instagram login.

• 17:53Speaker 00

  Yeah. It's good to know. It's good to get that reminder every now and then.

• 17:57Speaker 01

  LinkedIn, I check probably three, four times a week. We also get good leads from there.

• 18:01Speaker 00

  Yeah. LinkedIn has been great for the DM type leads. Um, Instagram, I can't say I've gotten good leads from Instagram. Anyway, but that's how you make millions from podcasting. It can be either a product or service you sell on the backend, or you can sell ads for very expensive. And when you have a long form podcast, like an acquired or, or, I don't know how much founders makes, but Lenny's podcast as a solopreneur, I think he does well for himself. Um, I think it's, it's extremely valuable intention. So, okay guys, that's it for today. Uh, Neil came in sick. Thank you, Neil, for doing this sick and we'll see you guys next week. Um, hopefully we'll be in person. So, goodbye.