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#415 - Cold Outreach Hot Seat: What Founders Are Asking in 2026

12m 26s

#415 - Cold Outreach Hot Seat: What Founders Are Asking in 2026

The discussion provides rapid-fire advice on cold outreach, emphasizing LinkedIn optimization with a complete profile and cautious scaling. For messaging, it suggests warming up contacts by targeting shared groups or locations and using tools to focus on active users. Success in cold email comes from creative, non-generic entry points and tailored strategies rather than standard demo requests. Multi-channel approaches are preferred over single methods, with the best channel depending on where prospects are most accessible. Timing is less about specific hours and more about consistent action, though audience context like holidays can matter. For large companies, LinkedIn helps bypass gatekeepers, but a blended strategy is key. Email deliverability improves with specialized tools, and cold email effectiveness hinges on originality. In omni-channel campaigns, starting with LinkedIn can boost efficiency, but always align with prospect activity. Finally, launch outreach promptly without delaying for holidays, as immediate needs can create opportunities, except during major crises.

Transcription

2105 Words, 11329 Characters

English
All right, Jeremy, we're going to do rapid fire. Let's get straight to it. Question number one out of 10. I'm starting LinkedIn cold outreach. What are some tips that I need to keep in mind? Do you want to start? I'm going to jump in. So make sure your profile is dressed for success. That means a good headline, the right job title, a banner, image that doesn't look awful. And then please just go slowly and only scale once you've hit some good responses in the beginning. You're probably messed up a lot. So tread carefully and slowly. I love it. I would also say start paying. Get a service indicator so you get less chances of getting into trouble. Sometimes you got to pay to play. Yes. I love it. Question two. Linked in cold messaging, prospecting best practices. OK. So I think this is a question of how do you go about building that list for LinkedIn cold messaging. So try and make your cold messaging less cold by finding groups, industries, maybe even locations where you've got a foothold so that when you reach out, they may know the people in your case study. They may know people you've worked with, clients, et cetera. Yeah. I love the location play. I would also say if you're using sales indicator, don't forget to mention active on LinkedIn. Because it's not because they have a profile that they're going to reply to you. And especially at the beginning, if you're sending a lot of invites, it's kind of like stupid to send them to people who will never check. You get less chances of replies. And then more chances of LinkedIn to fly you because you got too many pending requests. I'm Donk Jeremy. All right. Here's a fun one. Cold email never worked for me until I use Quick Mail. There you go. OK. So I think for me, it was until you started taking different entry points. So everybody and their mother wants to ask them, hey, you want to join me for a 30 minute demo. But if you can step around that common path and find different, we'll call them doorways or entry points to your end buyer, then ColatReach starts to be a whole lot more fun. You got one? Yeah. I love it. It's very similar to me. It's like until I find the right strategy, which is also leading or indicating what least you're going to go after, which people, what role, everything, and what message you're going to hit them with. As soon as you're starting to align everything, and it's working, then yeah, then yeah, you get more chances of making it work. Love that. OK. Number four, best time for ColatReach, time and day. You're the go-to on this journey, what you got. Oh, man, you're not going to like my answer. I don't care. It shows basically every message. Not all message can be sent at the same time anyway. So if you're going for even a little volume, and you're going to have to space your messages, then you're already going to think about like, span of multiple hours. So you may well just do it during your work day, and then that's it. I love the question. And you know what I think this challenge or problem is, this is like a very buzzy question to ask, where we feel like we're getting towards like, my true intention. Right. But the reality is like, the best time for ColatReach is right now. Go do the damn thing, you know, or it needs to happen. OK. Number five, we're halfway through, bud. So if you could only do one, would you do LinkedIn, cold call, or cold email? I know you'll take this one, Jeremy. Yeah, like I do love LinkedIn. But to be honest, like, if you're asking yourself, if you can only do one, isn't that like inside the box thinking that we probably want to push back on the question? If you're going to force me to choose LinkedIn, but if I can just make a statement like, it's not like that, multi-channel is fun. Yes, I would say like, hey, these arguments for, you know, being the expert in one channel, because there's so much things to learn at this stage. So it's more or less a bandwidth issue. And like, you know, would I spend my time learning all the thing you need to know for cold email or all the thing to-- some things make it easier. Of course, you know, multi-channel tools. They kind of like help you with that, like quick mail, you know, a shameless plug. But I would say my answer would actually depend on the prospect. You know, some people are just like not on LinkedIn. Some people are on LinkedIn. Some people are, you know, open to call to fun call. If you're funny, if you're doing Europe stuff, like don't bother with fun. Like, we don't like this. It is not going to reply. But if you're doing a medical, maybe you get some chances. Go where your prospects are. Yes. That's the one. And then, my gosh, I can't blank my mind on a rapid fire. We're just going to keep going. Next question. Damn, I thought I had like a pretty darn good point. Number six, how do we improve email deliverability for cold outreach? Jeremy, I'm leaning on you. Do you know if the ability is a problem? Yeah, I'm sorry, but I'm going to say like use quick mail. We've got so many tools for it. Like so many features for it. You got like the river really T.A.I. You got reword with A.I. You got inbox rotation. And it's like, that's right. You got stealth mode. You got like everything like, you know, for good deliverability. If you can't make it work with quick mail, then just give up. There you go. All right, enough said. Thank you. Question seven. My turn. Cold calls versus cold emails for breaking into huge companies was better. To be honest, large companies, they have that gatekeeper effect. I'm not here on a lot of resounding success stories bringing into large accounts with calling. Am I alone on this one, Jeremy? You got any thoughts? I don't know for sure, actually. I mean, we try at some point. And people have trouble to go through gatekeepers. And the question then is like, is it the ski issue? Or is it really the size of the company issue? Because at the end of the day, LinkedIn enable you to sort of like, almost by pass gatekeeper in theory, must be for these days, have people even like, you know, filtering their LinkedIn inbox. But mostly, you know, you can go to people directly. So I'm not probably the right person for calling. But for the rest, I would say, yeah, you go away on your prospect is a cheat, you know, straight away without gatekeepers. And the nice thing is like, I have to say, at a large or in this question's language, huge company, they might be went to appropriate people for this discussion. And therefore, you might find mobile contact numbers for six of them. You might find that eight of them are crazy active on LinkedIn. And you might find 15 of them have valid email addresses. And it's like, again, push back towards that question of like, only choose one. Oh, I remember the thing I forgot. If you could only do one LinkedIn co-caller email, a really good tip is a lot of the best in class marketers have mastered one channel, but keep their eye on a second one. And they don't go a lot deeper than that so that they can get extremely proficient, you know, top one percent in the world without pigeon holding themselves so that they're at risk of becoming outdated or something if-- Yeah, the change. Exactly. The other channel could go down. And so it's great, great advice. I love it. Cool. All right. Three more Jeremy. Cold email isn't dead. You're just lazy and unoriginal. True false. I mean, is that a better lens? I'll do it. Like-- Sure. So if somebody's sitting there saying, gosh, we might actually be lazy and unoriginal, is it a good advice to try that back door? Like we mentioned briefly. Just dramatically spin up so you don't sound like-- every other competitor. Yeah, I mean, for me, it sounds like very your strategy. You know, changes strategy. And it's hard because some companies used to have like 200 clients and it was just cookie cutter approach, but that doesn't play well anymore. So it's difficult. Yes. I don't think it's about being lazy or unoriginal. I think it's just-- it's like a creative agency. Not everyone can be creative. And so I think coming up with a great strategy requires some skills. Or you should just pay someone like, sells bread, a feminist plug. Just go and do a strategy session with them. But yeah, I think it's just becoming harder. And then the mediocre doesn't cut it anymore. So the floor has been raised, basically. All right, Jeremy. LinkedIn or email, which one do we use as a first step when going Omni Channel? Yeah, which one do you want to go for? LinkedIn all day because you can A, reference it in your email, which if they don't accept your connection request, maybe that's a little bit step closer. Or maybe you don't reference it. And they've seen your name pop up, even if they didn't connect it. And then if they do accept your LinkedIn, it would save you, let's say, the email volume. So you may not even need if you've got the reply on LinkedIn. So it keeps your volume a little bit lower than you otherwise would have had. You got a little review? No, I think it's really great. What I would say is that it kind of depends on your bandwidth. Make sure as if you have a very good audience, very tight list, then yes. LinkedIn all day long. Again, assuming they're on LinkedIn, because if your audience not on LinkedIn, then what's the point? But I would say go for LinkedIn first if you're not limited by bandwidth. But if you forgot the sound for the end of the timer. But if you're, what was the, oh, damn, what was I saying? There was a song that came on. We were about to sing. Going where your prospects are using LinkedIn, but only if they're active there, right? Because you may want to start with the email. Yes. And I don't regret. I mean, it was good point, but maybe next time-- That happened. That's the TV sound play. OK, last question, Jeremy. It is middle of December, and I'm getting ready to launch a campaign. Should I wait until after the holidays? Am I crazy for launching now? Yes or no? Yes, you are crazy for waiting. Just send now. Just send now. Yeah. That's a good slogan. I mean, you should say whatever you want. That's like to show you that you should stand. So that's all. Look at that. I love it. Let me just share one pushback. If you are reaching out to marketers, especially in the B2C market, the holiday rush really takes up a lot of their bandwidth. So just expect a lot of, hey, Dutch with me in January. But I will say that if you're bringing up something that they're currently experiencing pain around in the holiday rush, the time you may actually work out in your favor because they'll be feeling the pain and your message can relieve that pain. So-- Oh, an exception. I mean, for me, holiday is not an exception. For not sending, it is things for, like, for example, and, you know, Hurraycan just destroyed for tsunami, whatever, like, some sort of, like, really bad things happen. Yeah, exactly. That's the time where you don't want to do outreach. Because then you can as incentive and, you know, like being a DJ. Way to end on a bright note, John. Let's all think of natural disasters as we break. All right. It's quickmail.com for your sending platform. It's salesbread.com just to get a lead today. And you just need a close-up. We'll set them up for you. All right, Jeremy. Thanks. Great. Great cast.

Podcast Summary

Key Points:

  1. Optimize your LinkedIn profile with a professional headline, banner, and job title before starting cold outreach, and scale efforts slowly after initial success.
  2. Make cold messaging warmer by targeting specific groups, industries, or locations where you have connections, and use tools to identify active users.
  3. Cold outreach success often depends on finding unique entry points and tailored strategies rather than generic demos, and multi-channel approaches are generally more effective.
  4. The best time for outreach is now; timing is less critical than consistent action, though consider audience-specific factors like holidays or time zones.
  5. Improve email deliverability using specialized tools that offer features like inbox rotation, AI rewriting, and stealth modes.
  6. For large companies, LinkedIn can help bypass gatekeepers, but a multi-channel strategy targeting where prospects are most active is ideal.
  7. Cold email remains viable but requires creativity and originality to stand out, as generic approaches are less effective now.
  8. When using omni-channel outreach, starting with LinkedIn can reduce email volume and increase familiarity, but always prioritize where your prospects are active.
  9. Launch campaigns immediately rather than waiting for holidays; timing can work in your favor if addressing current pain points, barring major crises.

Summary:

The discussion provides rapid-fire advice on cold outreach, emphasizing LinkedIn optimization with a complete profile and cautious scaling. For messaging, it suggests warming up contacts by targeting shared groups or locations and using tools to focus on active users. Success in cold email comes from creative, non-generic entry points and tailored strategies rather than standard demo requests.

Multi-channel approaches are preferred over single methods, with the best channel depending on where prospects are most accessible. Timing is less about specific hours and more about consistent action, though audience context like holidays can matter. For large companies, LinkedIn helps bypass gatekeepers, but a blended strategy is key.

Email deliverability improves with specialized tools, and cold email effectiveness hinges on originality. In omni-channel campaigns, starting with LinkedIn can boost efficiency, but always align with prospect activity. Finally, launch outreach promptly without delaying for holidays, as immediate needs can create opportunities, except during major crises.

FAQs

Ensure your profile is optimized with a good headline, job title, and banner image. Start slowly and scale only after receiving positive responses, and consider using paid services to reduce risks.

Make your outreach less cold by targeting groups, industries, or locations where you have connections. Use tools like Sales Navigator to focus on active LinkedIn users to avoid pending requests and improve reply rates.

Avoid generic demos by finding unique entry points to your prospects. Align your strategy with specific roles and messages, and use tools like Quick Mail for better deliverability and features.

There's no single best time; space your messages throughout your workday. The key is to start now rather than waiting for an ideal moment, as timing depends on volume and scheduling.

It depends on where your prospects are most active. Multi-channel approaches are effective, but if bandwidth is limited, master one channel while keeping an eye on another to stay adaptable.

Use tools like Quick Mail that offer features for deliverability, such as inbox rotation and AI-assisted rewording. Proper setup can significantly reduce issues with email blocking.

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