How to Craft Cold Outreach That Actually Works

Summary

Help Wanted Episode Summary: "How to Craft Cold Outreach That Actually Works"

Release Date: February 18, 2025

Hosts:

• Jason Pfeiffer – Editor in Chief of Entrepreneur Magazine
• Nicole Lapin – Money Expert
• Guest: Jenny Wood – Former Google Executive, Author of Wild Courage: Go After What You Want and Get It

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1. Introduction

In this episode of Help Wanted, hosted by Jason Pfeiffer and interim co-host Jenny Wood, the focus is on mastering the art of cold outreach. Cold outreach is an essential skill for professionals aiming to expand their networks, secure endorsements, or pursue new opportunities. The discussion delves into effective strategies, common challenges, and actionable tips to enhance the success rate of reaching out to individuals who are strangers.

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2. Guest Background: Jenny Wood

Jenny Wood joins the show as a seasoned professional with a rich background:

• Former Executive at Google: Leveraged relationship mapping techniques to manage and nurture business connections.
• Author of Wild Courage: Go After What You Want and Get It: Shares insights on overcoming fears related to uncertainty, failure, and judgment.
• Prolific Cold Outreacher: Successfully connected with high-profile authors like Dan Pink, Gretchen Rubin, and Seth Godin, while also facing challenges with other notable figures.

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3. Challenges with Cold Outreach

Jenny opens up about the inherent fears associated with cold outreach:

• Nervousness and Uncomfortableness: Despite her success, Jenny admits, “[03:56] Jenny Wood: Hell, yes. But not as uncomfortable as the average person.”
• Fear of Rejection: The emotional toll of sending out numerous requests with limited responses can be daunting. Jenny shares experiences where high-profile individuals like Tina Fey and Oprah did not respond, leading to self-doubt and questioning her approach.

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4. Strategies for Effective Cold Outreach

a. Personalized Videos

Jenny emphasizes the power of personalized videos:

• Tailored Content: Creating a specific video for each individual, referencing their work and demonstrating genuine interest. “[08:13] Jenny Wood: I recorded a video specific for each of them, telling them how much I love their work and using specific examples from their books.”
• Conciseness: Keeping videos under two to three minutes ensures the message is clear and respects the recipient’s time.

b. Handwritten Notes

While challenging to execute digitally, Jenny adapted handwritten notes by:

• Digital Adaptation: Taking pictures of handwritten notes and sharing them via Google Docs. “[08:39] Jenny Wood: I wrote a handwritten note to each of them and I took a picture of it and uploaded it.”
• Personal Touch: Even in a virtual format, handwritten elements can convey sincerity and effort.

c. Voice Memos and Audio Engagement

Nicole and Jenny discuss the effectiveness of using voice memos:

• Direct Communication: Sending voice memos on platforms like LinkedIn can stand out compared to traditional text messages. “[18:38] Jenny Wood: If someone sends me a voice memo, there is literally a microphone right there on the app, on LinkedIn.”
• Engagement: Audio messages require real-time attention, making it harder for recipients to skim and more likely to absorb the content.

d. Relationship Mapping and Segmentation

Jenny introduces the concept of relationship mapping akin to a Customer Relationship Manager (CRM):

• Organized Outreach: Segmenting contacts based on relationship strength and importance. “[33:02] Jenny Wood: I have a spreadsheet of maybe 150ish names. I have a color code of red, yellow, green of the relationship strength.”
• Targeted Approach: Prioritizing outreach efforts to high-value contacts ensures efficient use of time and resources.

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5. Handling Rejection and Persistence

Jenny shares her methods for coping with rejection:

• Reframing Failure: Distinguishing between objective truths and unhelpful narratives. “[42:05] Jenny Wood: Truths are the facts... Tales are the stories I create to make sense of the facts.”
• Persistence: Continuing to reach out even after setbacks, as demonstrated in her successful engagement with Ali Abdaal through multiple follow-ups.
• Community Support: Leveraging mutual connections for encouragement and strategies to refine outreach tactics.

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6. Real-Life Examples and Case Studies

a. Successes

• High-Profile Endorsements: Achieved blurbs from renowned authors like Dan Pink, Gretchen Rubin, and Seth Godin.

b. Failures

• Tina Fey and Oprah: Faced non-responses and even negative feedback from management, highlighting the unpredictability of cold outreach.
• Ali Abdaal Connection: After persistent efforts, Jenny secured a meeting with the musician she admired, illustrating the potential rewards of resilience.

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7. Practical Tips for Listeners

Jenny and Nicole provide actionable advice for effective cold outreach:

1. Personalization is Key: Tailor each message to the individual’s work and interests to demonstrate genuine engagement.
2. Leverage Different Mediums: Utilize videos, handwritten notes, and voice memos to stand out from standard email blasts.
3. Organize Your Outreach: Implement relationship mapping to prioritize contacts and streamline efforts.
4. Be Clear and Specific: Clearly articulate what you’re asking for and how the recipient can contribute.
5. Handle Rejection Gracefully: Accept ‘no’ as a possibility and use it as a learning opportunity.
6. Follow Up Thoughtfully: Persistence can pay off, but it’s important to balance follow-ups without being overwhelming.

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8. Conclusion

The episode concludes with a powerful takeaway: Effective cold outreach requires a blend of personalization, strategic organization, and emotional resilience. By adopting Jenny Wood’s methods—such as personalized videos, meticulous relationship mapping, and leveraging voice memos—professionals can enhance their chances of meaningful connections. Moreover, embracing rejection as part of the journey fosters growth and persistence, ultimately leading to successful outcomes.

Notable Quotes:

• “[03:56] Jenny Wood: Hell, yes. But not as uncomfortable as the average person.”
• “[12:54] Jenny Wood: Are you saying there's a chance?”
• “[22:10] Jenny Wood: But that's got at least a 57% open rate, that subject.”
• “[32:35] Jenny Wood: This is a relationship map. It’s like your own CRM.”

Timestamp Highlights:

• 03:18 – Introduction of the topic and guest’s cold outreach experiences.
• 08:08 – Jenny describes her approach to reaching out to high-profile individuals.
• 12:30 – Tina Fey’s manager’s response to Jenny’s outreach.
• 18:38 – Discussion on the effectiveness of voice memos.
• 33:02 – Explanation of relationship mapping and CRM usage.
• 42:05 – Jenny’s strategy for overcoming rejection.
• 44:08 – Encouragement for listeners to implement cold outreach tactics.

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Final Thoughts: Whether you’re an entrepreneur seeking partnerships, a professional aiming to expand your network, or an author looking for endorsements, mastering cold outreach can significantly impact your success. By incorporating personalized, thoughtful strategies and maintaining resilience in the face of challenges, you can transform your outreach efforts from daunting tasks into rewarding opportunities.

Transcript

[Jason Pfeiffer]

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[Nicole Lapin]

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[Jenny Wood]

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[Nicole Lapin]

This is help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.

Entrepreneur Magaz, and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

And on Thursdays, I give you one way to improve your work and build a career or company you love.

And it starts now.

Jenny, you have to reach out to a lot of people, right? Like, just in your job, you're reaching out to people all the time.

[Jenny Wood]

All the time.

[Nicole Lapin]

A lot of those people you don't know.

[Jenny Wood]

That is correct.

[Nicole Lapin]

This is my awkward Socratic method way of getting to the point that you have to reach out to a lot of people. Cold, right? Like a lot of people who you don't know who you want something from, and the only way to get them, or at least to get their attention is to just reach out to them. Absolutely cold, correct?

[Jenny Wood]

A hundred percent. Yes. Sometimes it works and sometimes it doesn't.

[Nicole Lapin]

Okay, we'll talk about that later. But here's the question that I most want to know right now. Does that make you nervous or uncomfortable?

[Jenny Wood]

Hell, yes.

[Nicole Lapin]

Really?

[Jenny Wood]

But. But. But not as uncomfortable as the average person.

[Nicole Lapin]

Ah, okay. All right. Well, that's interesting because this is what we're talking about. How to approach it in a way that one is comfortable enough that you'll actually do. But number two, that's really interesting because I thought you as a person, and I'm going to explain who you are in just a second. This is just like a setup. But I thought you. I perceive you as someone who is fearless in reaching out cold to people because you do it all the time. And you have reached out to celebrities and gotten them to respond and extremely famous authors and gotten them to respond. And I just figured Jenny just does this because she is a fearless person who does not mind reaching out to anybody. And it is very interesting to hear you say you are afraid of this, too. You're just marginally less afraid than other people.

[Jenny Wood]

Or I just push past that fear, knowing that some success might lie on the other side.

[Nicole Lapin]

Ooh. Okay, you have set us up nicely. First, let us acknowledge Jenny, because I keep saying, Jenny, Jenny, you are not Nicole Lapin, which is to say you are. You are not my usual co host for this show, Nicole is on maternity leave. You are Jenny Wood. You are. And I'm going to tell you who you are. You are a former executive at Google. You are the author of a fantastic new book, Wild Courage. Go after what you want and get it. You are also a longtime friend of Jason Pfeiffer. And you. I have watched you, Jenny, in the lead up to this book in particular, because this has been years in the making. I've watched you reach out to the most famous authors, sometimes to ask them to, like, endorse your book, sometimes to ask them for just advice on launching a book.

[Jason Pfeiffer]

And I have watched this and thought.

[Nicole Lapin]

To myself, I would, it wouldn't even occur to me to reach out to people in the way that you do at the volume that you do it. And I have been shocked, shocked at how many of them respond because, okay, you had a cool job at Google for a while and now you have a cool book. But, like, when you were reaching out to them, you know, you're still just like a random person and they're a famous person. So I want to understand how you are doing that and how you can push past the fear of doing that. So where do we even begin?

[Jenny Wood]

Okay, where do we begin? It's actually an interesting time to be asking me, because today, on this particular day that we're recording this, I'm feeling like my reach out is just rife with failure. So it's like, so you said, like, does that scare you? I'm like, yes, it terrifies me. But on another day where someone responds and they're like, sure, we were interested in your book, then I feel like this is a great strategy. So, okay, maybe we'll start with some of the people I've reached out to. And I'm going to name names.

[Nicole Lapin]

So name names.

[Jenny Wood]

Dan Pink, Gretchen Rubin, Seth Godin.

[Nicole Lapin]

For people who don't know, those are like giant names in the particularly, like, business book space. Right. I don't know. Is Gretchen Rubin a business author? I don't know.

[Jenny Wood]

Yeah, I would say business self help.

[Nicole Lapin]

Self help, yeah. Anyway, big, big, big names. The kind of people who just get a bazillion emails and surely ignore the vast majority of them.

[Jenny Wood]

Yeah. So, like, those were successes. Now, to be fair, I was still at Google when those happened. And so I did have something that I could also, you know, be excited to partner with them on. They did talks at Google and, and like that said, it was still kind of a. They get a lot of requests to do a lot of opportunities. So you still have to cut through the noise to some extent. So those are wins. Right. And now let's maybe take it when, when I'm just a literally cold outreach. Will you support this book? You've never heard of me? Here is my name, here is my manuscript. Right. Like, like as if you're at a, at a restaurant in LA and. And the waiter, like, slips his, you know, his screenplay to the, to the famous producer. Like, like, like just so subtly that that's kind of me just virtually. Let's talk about some failures. So, yeah, I reached out for this book. Cold nothing to offer them. Brene Brown, Tina Fey, Glennon Doyle, Oprah, Michelle Obama.

[Nicole Lapin]

Sure, sure. Small names. They. Nobody ever reaches out to them.

[Jenny Wood]

Budding stars. Yeah. Okay. So like they're not all wins. But I think what's interesting about this is how I reached out. I recorded a video specific for each of them, telling them how much I love their work and using specific examples from their books, which I actually read in my video. I kept it under like two to three minutes. YouTube video number two. I wrote a handwritten note to each of them and I took a picture of it and uploaded it. This will become relevant in a second. Uploaded it so that they could see the handwritten note. I didn't physically send it because I didn't have an address.

[Nicole Lapin]

You didn't have an address? Yeah, that's why I was just going to say that's really, that's really interesting. Right, because people, people always say, like, the handwritten note is more personal than the email. But of course, you know, I don't know Oprah's home address. How would you ever send her a personal note?

[Jenny Wood]

Right. So that went virtually. And by the way, I'm like, literally in some of these cases, I don't even know if they ever did see these things because I was like, googling who, you know, manager for Oprah or PR person for Tina Fey or, you know, whatever I could find. Okay. So in this case, didn't hear back from a couple. Did hear back from Brene Brown's team. They're interested in looking at the book and think that it, you know, could have alignment with, with their work. I agree. Right. So that seems.

[Nicole Lapin]

And what do you, like, what do you want from her? What are you asking for?

[Jenny Wood]

So I try to be really specific in the ask and then also give them opportunity to be creative. So I said, I'd be so honored to have your support on this book in whatever way feels natural or comfortable to you. Perhaps by way of testimonial or Any other vehicle that would also benefit you and your audience. Something like that.

[Nicole Lapin]

Okay.

[Jenny Wood]

The amount of time I spent recording these videos and writing these handwritten notes was. I'm, like, embarrassed to admit how much time it was because you were probably.

[Nicole Lapin]

Like, with overthinking every single thing. Right?

[Jenny Wood]

Like, overthinking.

[Nicole Lapin]

Yeah. Like, if you have two minutes to say something to Tina Fey or Oprah that they might see, even if the chances of them seeing it are very low, like, that is not a. That is not a thing you take lightly. Like, you think about what you're gonna say.

[Jenny Wood]

Right? Absolutely. And, like, then when you talk about recording a video, which, like, what I try to do is. I try to. I try to cut through the noise. Oh, Jim Collins. That's another one. Wrote good to great super big author. I try to cut through the noise. So what does the scorecard look like? All right, so Dan Pink is blurbing my book. Gretchen Rubin is blurbing my book. Seth Godin has blurbed the book. Tina Fey. I got my wrist slapped. We can talk about that. And Brene Brown's team said, we're interested. You know, send us the manuscript.

[Nicole Lapin]

Right. And. And Michelle Obama and Oprah are hanging out with you on Thursday.

[Jenny Wood]

Yeah, exactly. Yeah, yeah. And then big, all Michelle Obama, Glennon Doyle, and Tina Fey.

[Nicole Lapin]

So do you get responses?

[Jenny Wood]

No, no, No, I don't. And that's kind of the worst because, I mean, you know how I met my husband? I chased a stranger off the New York City subway. I did that because I'd rather have an answer, even if the answer is no, than have uncertainty. So it's like a terrible feeling sitting in uncertainty. At some point, I give up. I'm like, okay, I'm not hearing back from Michelle Obama or Oprah. And then you just move on. But I'd so much rather hear a no than a nothing.

[Nicole Lapin]

So. All right, I have two directions that I want to go in here. One is to unpack the tactics here, which I think are really useful and apply to all sorts of, like, you know, the people who are listening to us now are not necessarily prepping for a big book launch and trying to reach out to Oprah. But. But they. They surely have to do cold outreach for all sorts of reasons, even if it's just a possible job opportunity or to a potential customer or whatever. So it's like, it's worth unpacking these tactics more, but because it sounds juicier first. How did you get your wrist slapped by Tina Fey?

[Jenny Wood]

Okay, not by Tina Fey personally. By her manager. So I just googled Tina Fey manager, and I got this guy's email address and he wrote back right away. And he said something to the effect of just to be fair to everyone, we politely decline blurb requests, you know, from friends, enemies and acquaintances alike or something like that. Like, really thoughtful.

[Nicole Lapin]

They have like a. They have like a fun line about it because they're sending it out 50 times a day.

[Jenny Wood]

Exactly. Exactly. Wait, no, I'm sorry. Really important word. We generally reject.

[Nicole Lapin]

Oh.

[Jenny Wood]

Requests from these three people. I write back. Apparently not living in fear that day. Jason. Feeling real. Feeling real. Right. Chapter three of my book is called Shameless. Living without shame. Living without imposter Syndrome. Living confidently. I write back and I say, so I see you've written generally. Are you saying there's a chance? And I link to the dumb and Dumber clip.

[Nicole Lapin]

Yeah. So you're saying there's saying there's a chance. Classic line that probably anybody younger than us has no idea what we're talking about. But yes, I know, because I'm old.

[Jenny Wood]

But like, can you believe that I wrote that back?

[Nicole Lapin]

I. Well, I can because you're doing this kind of stuff all the time. But like, what was going through. Wait, okay, so we'll, we'll. But what was going through your head? And then what happened?

[Jenny Wood]

Yeah, so what was going through my head was like, maybe I'm just not good at reading the room. Sometimes it's like, no, obviously he was saying no, but I was like, well, let's keep this conversation alive. Like, let's really see if there's an opportunity here. So I was like using my left brain tendencies, I was very logically looking at a binary. Is this a one or a zero? Well, he hasn't said it's a one or a zero. So let's see if we can get to conclusion here. So I was very realistically trying to understand, like, okay, are there any conditions under which she would blurb the book? Again, her manager. And so he then writes back and he says, okay, and now I also have to clarify the way I set the handwritten note because I didn't have her address was I linked it to a Google Doc. I was a Google 18 years. So like I, if I want to share a file, I just think to put it in a Google Doc. It doesn't occur to me to do it any other way. Just a shared Google Doc. So you click on the link and you see the thing. I've taken a picture of the handwritten. So he said, no, this is A definite. He wrote, writes back. I say, you know, are you saying there's a chance? Is there a chance? He writes back, this is a definite. No. And I also found it inappropriate that you used a Google Doc to link to the picture of your note so that you could see if Tina Fey had opened it and scrape her email or. Those weren't his exact words, but that was the sentiment.

[Nicole Lapin]

Can you do that? Is that a thing you can do?

[Jenny Wood]

Yeah, like, it never occurred to me. It is something you, you could see who's opened this document. But, like, it. I wasn't even sure. I didn't even understand what he was saying. I didn't even understand what his point was. And I was like, oh, he thinks that I would like, go into like the analytics of this document and then see who opened it. He didn't use the word scrape her email, but he basically said that was the idea. Yeah, that was the idea. Like he said, I think it's inappropriate that you'd put it in a format that you'd be able to see who opened it. Something like that. And it crushed me. It crushed me. And was the kind of thing that, like, if I was planning to send, you know, nine more videos that day and I only sent maybe 10 total, if I was planning to send, you know, some amount more that day that I just like, didn't want to anymore because rejection sucks. And feeling like you're in trouble, I felt like I was in trouble. Right. Three fears I talk about in the book Wild Courage are fear of uncertainty, fear of failure, fear of the judgment of others. And I felt like, oh, not only did this not work, but now someone is mad at me, waving their finger. I'm in the principal's office. Not that he. Not that this took more than a third of a second of his day to think about. I thought about it for three days non stop. And that sucked.

[Nicole Lapin]

Yeah, I mean, I have felt that too, in all sorts of moments. And it's funny because you think about it and you're like, well, look, you didn't know that guy before. You're not going to know him after it. Your career path and Tina Fey's career path unlikely to intersect in any meaningful way. It doesn't really matter if that guy likes you or not, but it still feels bad to just like blow it. But, but this is to, to do any kind of cold outreach is to put yourself in a situation where like, the chances are you're going to be rejected or ignored. I suppose it's a lower chance that Someone's gonna, like, snap back at you. But you. You also, you pushed it further than maybe the average person would have.

[Jenny Wood]

Are you saying I deserved it, Jason?

[Nicole Lapin]

I'm not saying that you deserved it, but I'm saying that you. I'm saying that you waited deeper into the territory than others do. And so. So no. I mean, I don't think that he should have been, like, snotty like that. I mean, I've had people do this to me where I. I reject, but maybe use some somehow qualitative language and somebody will see if there's an opening there. Or. Or I'll be like, I often what will happen is if somebody will pitch me something and I'll say, this isn't a fit for the magazine, and then. And they'll respond, yeah, either for now. I. Sometimes I say for now. And they'll be like, oh, when is it? Or I'll just say, it's not a fit. And then they'll be like, oh, can you tell me what is a fit? And they don't mean it in a snotty way. They're just like, oh, well, tell me, what are you working on right now? I'll do whatever you want. And, yeah, I actually find that to be incredibly annoying, but what I just do is just not respond. Like, that's just the end of the conversation.

[Jenny Wood]

Sure, sure, sure. Yeah. And I did respond and Apollo. And I apologized, actually, because I did realize that it could have been perceived that way. And by the way, his notes back were really thoughtful. Like, I want to give this guy a ton of credit because I actually thought it was a really interesting and thoughtful exchange, even though I was super bummed. So, you know, you might not wade in knee deep or waist deep or chest high when you're doing this, but, like, there are ways you can wade in toe deep or ankle deep that if you're not reaching out and sending videos to Michelle Obama and Oprah and Tina Fey, I mean, maybe you're reaching out to people on LinkedIn. That's a very normal thing that people do all the time to try to build business or try to get a job or try to build community. And, like, here's a real micro version of that that I think is quite attainable and very realistic and really smart. You're not going to record a five minute video or two minute video and send it to a celebrity. But, like, if someone sends me a voice memo on LinkedIn, yeah, that stands out so much. Let's say they want to partner with me on something. Or they want my advice, or they want my mentorship, or they want me to comment on their LinkedIn post. If someone sends me a voicemail, there's literally a microphone right there on the. On your phone, on the app, on LinkedIn.

[Nicole Lapin]

Yeah, there's a little button. There's a little button. You tap it and it just starts recording your voice.

[Jenny Wood]

Exactly. You have one minute. You can record a couple if you can't say it in a minute. But, like, I always notice those voice recordings and I do not always notice my text DMs or I just don't always read all of them. And I have other people in my LinkedIn profile, like helping me with DMs and helping manage them. And so. But if someone sends me a voice memo, that will get flagged to me and I will absolutely listen to it. So that's kind of like the same principle. How do you stand out? How do you cut through the noise? How do you change the medium in a way that gets people to pay attention? And this, I think, is a realistic tactic that works as opposed to going above and beyond or just like taking it maybe too far.

[Nicole Lapin]

Stick around. Help Wanted will be right back. Welcome back to Help Wanted. Let's get to it. I also receive a bunch of voice memos from people on LinkedIn. I have had people email me with links to a, like, video that they made. Usually what they do is they post it private on. On YouTube and then send it to me. Yeah, I do actually always watch them or always listen. And then a very interesting thing happens in my brain, which is, okay, so you've got my attention now. And now, now I am stuck in a linear experience, which is to say, if you send me a note, I can scan it as fast as possible, but if I'm listening to something or watching something, I can only experience it second by second. Right. Like, there's no way. So now it's gotta be real good. Like, I. You've got my attention now. It's gotta be real good. And I have found that some people are actually very good at this. Like, they open and they're warm and they're direct and they're good talkers and it moves. And in 60 seconds, they have communicated something to me. And then there are other people who. It starts, and then it's like 20 seconds in and I don't know what they're talking about. And I am. I am out at that point. So.

[Jenny Wood]

So high risk, high reward. Maybe it is.

[Nicole Lapin]

Right, right, right. It's like, it's like, you have to, it's almost like you have to split the interaction into two, right? Which is like thing number one is what is the way to get them to look at it? And you can't be, this can't be undermining, right? Like, they're all, they're like, people use these sales email tactics all the time that are super undermining and I, and I really hate them. Actually, a friend of mine just forwarded me one, which I'm just going to tell you is like, what does undermining look like? Oh yeah, hold on, let's find it.

[Jenny Wood]

I'm so curious to hear this as you're looking for it because I'm also doing a ton of cold outreach to like universities and book clubs right now. And that's super cold and probably feels a little like, you know, and companies for keynotes and things like that. So I want to hear what is undermining.

[Nicole Lapin]

Oh, yeah, no, okay, I got it. I got it up. So this is, I mean, if you're doing anything like this when you're reaching out to anybody, then we are ending this conversation right now.

[Jenny Wood]

We'll see. I'll be honest.

[Nicole Lapin]

Okay, so this went to my friend Jess. The subject line is, Jessica, return my money asap. Oh, and then the opening of the email is, oops, nothing to return, but is like blank service that they offer, you know, like interesting to you, we help. And then it just like launches into what they have to offer.

[Jenny Wood]

I mean, clickbait.

[Nicole Lapin]

Yeah, like, it is, it's a good subject line if you want anyone to open the email, like people will open the email.

[Jenny Wood]

But that's got at least a 57% open rate, that subject.

[Nicole Lapin]

Yeah, that's a great subject line, but I don't know how you recover from that because somebody off. If the, if the way that you got my attention was that you tricked me, my assumption is that that is how you operate. Then like there are more tricks ahead. Like you were just going to be tricking me the whole time. So I, I would never engage with somebody who said something like that. Yeah, so you do like. Okay, so we've split the interaction into two. Like part one is just like what gets their attention. And I think that in a way these, a traditional mediums like voice memo or video does get someone's attention because it is a more human interaction.

[Jenny Wood]

It gives you personality too.

[Nicole Lapin]

It does. It gives you personality. What I was going to say was it shows me that the person reaching out to me had to spend time thinking about what to Say directly to me, because an email can be, can be blasted out or it could just be copy and pasted. I don't know. Did you email me and like 70 other people at the same time? But if you've made this video and it's for me, then I know that you spent some time. So that hooks up. But then the second thing is it's got to be good and it's got to be good out of the gate. Like you have to. So what? Like when you were, when you were recording these videos or voice memos to people, how do you open it? Like, what did you say to Oprah?

[Jenny Wood]

Yeah, sure. So I woo with you. This is, this happens to be a tool I talk about in the manipulative chapter of my book, which is all about building influence through empathy. Not manipulative in the bad way. Manipulative in a way that, like, you can influence and you can use your influence and you can be smart about how people tick and how relationships work. Guess what? All the science tells us that people like to think about themselves and talk about themselves and people have egos. So how would I open it? Always focus on their work first. What is a favorite line from one of their books? It's actually not. You know, it's funny that you say, like, you've gotta hook them in the first 20 seconds and in the case that you've gotten videos, like, if they don't get to the point in the first 20 seconds, you're out. In this case, I don't know that I did get to the point in the first 20 seconds. I focus on them because being on the receiving end of some of these types of emails, I mean, not the level that these famous people would be, but if someone says, jenny, I've been following your work for five years and I can't tell you how much the woo with you right now. We're getting better. The past future bridge concept, right? Just another random concept that I've taught. I can't tell you how much the past future bridge framework has changed my life. And I used it once and this is what happened. Like, I'm paying attention. I work hard to put content out in the world. I worked hard to write this book. I worked hard at Google for 18 years to help people develop, develop their careers. And so if someone starts with what I've done, they that's woo with you. So don't start all your sentences with I, I, I. Actually, I think this is something you taught me, Jason, like years ago we were on a hike Once. And we talked about, like, how do you not use. Start your sentences with I? How do you start the majority of them? With you. And I call that woo with you. So in the book, I should have given you credit. I don't know if I should.

[Nicole Lapin]

I feel ripped off.

[Jenny Wood]

Sorry.

[Nicole Lapin]

You didn't woo with me.

[Jenny Wood]

Yeah, exactly. Well, I think we talked about it in theory and maybe I involved in you.

[Nicole Lapin]

It's fine. Like, I am not the only person.

[Jenny Wood]

To come up with that.

[Nicole Lapin]

So. Yeah, I think that that's. That's absolutely right. I mean, it is interesting because probably the more famous that you get, the more in which people are saying versions of that to you all the time. And. And I would. I will tell you something. Here's. Here's the thing. Here's the thing I've found surprising about my own work. And look, I'm not the most famous person in the world by a long shot, but I've been doing this long enough now that my work has reached a lot of people. And I do get a large number of emails from people who tell me that a thing that I wrote impacted them in some way. And I have been shocked at the degree to which this has become normal to me, such that I don't actually pause on it the way that I used to. Like, it almost feels like it.

[Jenny Wood]

Almost pause.

[Nicole Lapin]

Yeah. Oh, yeah. It's because you're still new at it. Exactly. Yeah. Like now it's not like I disregard it, but really, I just. What. What still does matter to me is like, do you follow and care about my work? But once I know that, like, oh, yes, you are a. You are a person who's actually paying attention to me versus a person who's just saying they like my work and they don't really care. They just want something like that's actually kind of the bar to pass. And then after that, at this point, it's actually gotta be something pretty unique. Like somebody just reached out to me because they tattooed a phrase that I wrote on their shoulder. Like, that was very unique. Like, that. That got my attention immediately. But. But usually at this point, it's like, it's really nice, but it is weird how many things you just get really used to. I don't know. I remember. I remember meeting Ben Folds many years ago, and Ben Folds was one of, like three artists, musical artists in high school that like, really helped shaped me and felt like they were articulating the things that I couldn't articulate myself. And, you know, I. I still don't know how to articulate that to Ben Folds. Like, it's too awkward. But, you know, I kind of tried. I was kind of like, you know, like, your music meant a lot to me in high school and really helped me. So. And he was very nice, and he, you know, he kind of nodded along, but as I was saying it, I was like, you have heard this too many times, and I don't know that I can say something to you that feels unique. So anyway, point is possibly, possibly you don't need to, like, I think maybe woo them as much, depending on how much success somebody has had. But, you know, if you're reaching out to, like, someone you might just want to work with back at the normal, normal level of life.

[Jenny Wood]

I want to bring us back down to, like, the average person. Right. Because we. I mean, we're both average people. I far more average than you, but however you define average.

[Nicole Lapin]

Although I did get the tattoo. I get to get the woman tattooed, but that's about it before we go.

[Jenny Wood]

Back to, like, everyday tactics. What was the phrase on the tattoo?

[Nicole Lapin]

To the ocean. It was to the ocean. It was, it was. It was from a newsletter that I wrote about a year ago.

[Jenny Wood]

Awesome.

[Nicole Lapin]

Yeah, it was great. It's so cool.

[Jenny Wood]

Yeah, that is so. That's so fun. Okay, but, like, let's take it down to day to day stuff, because day to day, right? You know, people listening right now, hello, all of you. You're not reaching out to celebrities. You're not like, you maybe not said something that someone's going to go tattoo on their shoulder or wherever they tattooed it.

[Nicole Lapin]

Yeah.

[Jenny Wood]

But, like, I do stand behind this concept of woo with you. Maybe you're desensitized to it, but if you're reaching out to your VP at your company, right. Or you want to build a relationship or a partnership, as an entrepreneur, I really think that still focusing on them first and then talking about what you have to offer, I. I stand behind this is an effective tactic.

[Nicole Lapin]

Yeah. No, I'm not disagreeing. I was just saying it is weird. What people can get used to is weird. What I've gotten used to. Okay, so here's. Here's the other place I want to go with this.

[Jenny Wood]

Sure.

[Nicole Lapin]

You have reached out to. Let me take you back, Jenny, to before you had a book to ask people for endorsements for, you started reaching out to very famous authors just to ask for advice. And again, I know now we're like, kind of back in famous territory. But, like, it doesn't have to be that because people reach out to random people for advice all the time. And I think that's, you know, it's a challenging thing to do because people get inundated the more. Especially the like, more senior they are, but still interesting. So. But you were doing it at such a volume, like you were reaching out to so many accomplished people to learn the things that they were learning. As you prepare to go down that journey that I will be honest, Jenny, you were telling me about the people you're reaching out to. And at some point I started wondering, what is the point of this?

[Jenny Wood]

Like, yeah, we talked about this.

[Nicole Lapin]

Yeah. Are you getting value out of this? Is. Is there like, just because you can cold outreach to someone, should you. Should you be like, how strategic should you be about who you are reaching out to or should. Should you just kind of like blanket? Because you can. I mean, look, it takes time to make the YouTube video and it takes time to make the audio, but you could still do it all day if you want it.

[Jenny Wood]

Yeah, yeah, yeah. Well, you segment your audience, right? Like, I'm not. I didn't. Jason, you never got a video for me. People like getting tattoos on of your stuff. But like, sorry, Jason, you weren't at video level. That was only Oprah and Michelle Obama. You know, like any good business person, you segment your customers, you segment your prospects. You've got platinum, gold, silver, bronze, right? So I only had about 10 people in the platinum level, right? And that was Glennon Doyle and Michelle Obama and Tina Fey. And then you get down to the gold level and maybe it's a tailored note, right? And it is still a line about, you know, what's impressed, what you love about their work, et cetera. Then you get down to, let's call it the silver level. And that's what I'm doing right now with universities and with book clubs where it is kind of more of a cold boilerplate thing that's slightly customized, but it reads kind of boilerplate. And honestly, like, that doesn't work that well. That's got a really, really, really low respons response rate. But I can have an intern do it and I can do it at scale and we can set it up in our newsletter provider and just very quickly send out 200 emails at one time where it's automatically replacing the university name or the person's name. So you really do segment it and not everybody gets a video. But, you know, I think your more important question is, does this work? Like, so now what?

[Nicole Lapin]

Yeah, now what?

[Jenny Wood]

Right now I've got all these relationships, some of them acquaintances, some of them truly have become close friends or business. Close business friends.

[Nicole Lapin]

Yeah.

[Jenny Wood]

And I don't think many people do this for a book launch, but I actually have a spreadsheet of maybe 150ish names. I have a color code of red, yellow, green of the relationship strength. I have the. The size of their audience, how big is their newsletter, how big is YouTube, how big is. By the way, now we're getting off of.

[Nicole Lapin]

Yeah, yeah, well, we were getting off of famous. Like, we're getting off of what the average person might do. But wait, can we go back to. You have. You are ranking color the strength of the relationship that you have with people.

[Jenny Wood]

Oh, my gosh, Jason, you're saying that. Okay, I mean, this was so much love, but you're saying we're getting away from what normal people do. This is how I ran a business at Google for 18 years. Having a relationship map and having red, yellow, green for strength and importance is a absolutely normal thing to do when you're running a business.

[Nicole Lapin]

To be clear, I meant the stuff about like, the number of YouTube subscribers that they have or whatever. Like, that's data.

[Jenny Wood]

Oh, yeah, yeah, yeah.

[Nicole Lapin]

Most people you reach out to don't have. But, no, but this, this is something that I, I can see the application. That's why. That's why I wanted to go to it. But I have no. Ever thought to do that. Like, that is not a. That is not a natural thing to think.

[Jenny Wood]

Smartest thing you can do. It's called a relationship map. This is like, they teach this in business school. It's a relationship map. So let's say you're a Google account executive and you and your accounts are Disney and Delta Airlines and American Airlines and, you know, name 10 others. You then have the. Well, who is the chief digital officer at Disney? Who is the chief revenue officer? Who is the head of social media? Who is the head of digital ad buys? And you might have five names under Disney. You actually have a column that's relationship strength. Red, yellow, green. The next column is importance to business growth. Red, yellow, green. When was the last time you met with them? When was the last time you emailed them? What did you talk about? It's kind of like your own internals. I mean, there's probably. Basically, I basically just created a. Yeah.

[Nicole Lapin]

Right, yeah, CRM for people who don't know a customer Relationship manager. Is that what that means?

[Jenny Wood]

Yeah, yeah, that's right.

[Nicole Lapin]

Yeah.

[Jenny Wood]

Like, Salesforce is the biggest one. Lots of other options too. So, you know, I'm saying all of this because of all those people I've met over the past three years, I am now reaching out to them and saying, hey, would you be open to sharing something about Wild Courage in your newsletter? And by the way, going back to let's stand out and you know, cut through the noise, I've gone ahead and drafted a couple paragraphs that might be a perfect fit for. For your audience. If it doesn't fit, no sweat at all. But I think that a, there's generosity, reciprocity. If I've put the effort into it, they might be like, oh, I feel bad telling her no, not that. You know, if they have a huge newsletter and they hold it really tightly, then they absolutely might have no problem saying no or not responding to me, even if I know them. But I do think, and we'll see, because the strategy is not done yet. We'll see how many people respond and who says, okay, well, I'm not going to do a whole newsletter about it, but I'll put it in a PS and maybe if I just reached out and said, hey, would you mention this? Maybe that would be a no. And at least now I get the PS because I've written a whole thing for them and they feel like, well, let me at least throw you a bone. I don't know. I don't know how this will. How this will pan out.

[Nicole Lapin]

Stick around. Help Wanted. We'll be right back. Welcome back to Help Wanted. Let's get to it. Okay, two final things. Number one, I just want to tell you a quick story that popped to mind as you were talking about an incredible cold outreach that someone did for me. And then I want to ask you one final question. Okay, sure. So the story is that many years ago, I got an email that was extremely well researched from a young woman named Madison. She was a student at, I think Boston University or Boston College. One or two. And she was interested in interning at Entrepreneur. She was, like, duly interested in journalism and in entrepreneurship. She had some, like, startup she was working on or something. And she had done a lot of research on me and Entrepreneur and she had articulated why she could be a valued entrepreneur, why she thought that Entrepreneur would be a value to her, like, specific things she could learn. Yeah. And I read it and I thought, very qualified. This is an impressive email. And I forwarded it along to someone on my team to, like, look into because we had sort of an intern program at the time. And then they just forgot to get back to her. And I, I wasn't aware and so, like, months went by, and Madison. I know. But then I discovered, for some reason, I can't remember why, that, like, the. My colleague had never wrote written back to Madison. And so I wrote her back, and I said, hey, I'm really sorry. Like, you wrote a good email, and it just kind of got lost in our system. So I just. I just wanted to say apologies and, like, good email, and. And what she responded with was, totally understand, et cetera, et cetera. I see that you are going to be in Boston soon. Because at the time, I had just started doing speaking, and I kept, like, a calendar of my events on my website, which I don't do anymore. Nobody should do that. It's not a good speaking move. But I did. I had a calendar of events. And so she saw that I was going to be in Boston, and she said, I see that you're going to be in Boston soon. You know, if you have time, I would. I would love to at least get coffee and ask you some advice. And then she, like, gave me some more insight into that she is consuming. And so I said, yes, we got coffee, and she was very impressive, and we had a really good conversation. And then at the end, you know, I was like, I'm gonna. Whenever you're available, I am. I will make sure you get an internship at Entrepreneur. And that's what happened. And I got her an internship, and now she's a founder, and it's a great. Like, she's fantastic. Anyway, she didn't do the video and the audio or whatever, but sure, what she did do, which I thought was really useful and interesting here is, in light of the conversation that we've had, is, like, so number one, extremely personal outreach.

[Jenny Wood]

Yeah.

[Nicole Lapin]

Also identifying exactly what she needs and what she has to offer. But funny enough, Jenny, she also did a version of what you did with Tina Fey, which is that I basically said no. Right. Like, I. I mean, in that case, I was like, look, I'm sorry. Like, we just. We blew it, and there's no internship for you. And she came back and asked for something else. And that, like, asking that thing took some legwork, and it was impressive, and it worked. So, anyway, you got. You got slapped by Tina Fey, but that strategy actually can work. It hadn't occurred to me until right now.

[Jenny Wood]

I have to share one more thing, Jason. Okay, so I told you that it's still sometimes terrifying for me to do this, and sometimes when I don't hear back from somebody, it just puts me in this tailspin of everyone's judging me and I'm too much and why am I doing this? And what, what, what am I even worth, right? Ali Abdaal is a big creator. Has like a 10 million person YouTube following. He's like one of the people who actually can really make the dent in someone's book. Like, he has that kind of following who actually buys books. And so I'd reached out to him a couple times, and I do know him personally, but I didn't hear back. And I was like, oh, man. It's like, you know, you think you know somebody. And then I was talking to a mutual friend, and she's like, you've just got to reach out again. And she's like, jenny, by the way, he is not going to do some janky zoom interview with you, like, offer to go to Hong Kong. So in your case, Madison knew you were going to Boston. In this case, this friend of mine was like, you gotta, you gotta do a hail Mary and email him.

[Nicole Lapin]

He's in Hong Kong.

[Jenny Wood]

I assume he just moved. He just moved from contact to know.

[Nicole Lapin]

Yeah. Okay. Yeah.

[Jenny Wood]

And so I got off the phone with our friend, our mutual friend. Subject line, Jason, QQ for you. Hop on a plane to come to Hong Kong. And I wrote such a heart. This is almost a different tactic. I was like, ali, this could change my life. This could change the curve of my book. I would be delighted to hop on a plane and come to Hong Kong. I also WhatsApp him. I hear nothing. I follow up. I hear nothing. A few days ago, I finally hear back from his general manager. Hey, Jenny, we're actually discussing this as an option in Friday's meeting. I hear back today, Jason, it's a go. See you in Hong Kong. So now I have Hong Kong.

[Nicole Lapin]

So now you gotta go.

[Jenny Wood]

Yeah. Good news, bad news. It might change the curve. Might bend the curve of the book. Bad news, I have to go to Hong Kong next week.

[Nicole Lapin]

What? You're going to. You're going to Hong Kong next week or the week?

[Jenny Wood]

I have to look at my schedule to be probably next week or the week after. I'm literally going to just go book a book ticket and go to Hong Kong and do this.

[Nicole Lapin]

Okay, that's an awesome story and tees up nicely. The final question that I wanted to ask you, which was to, like, loop back to that you said you were still afraid to do this, but you're just like, a little less afraid than other people. So I want to ask you, like, how you have just slightly diminished the fear such that you are Willing to do that. Like the number even in that story that you just said, the amount of times that you followed up, I don't think that I. I would have. I am in a situation right now where I was introduced to. To, like, a musician who I love. And I don't want to say the name on the show just because I don't want to, like, out him.

[Jenny Wood]

Sure. Everybody on the show I've never contacted.

[Nicole Lapin]

Yes, you have. I'm playing it a little closer to the best, but we have, like, a mutual friend and we got introduced and frankly, I don't have that much to offer him. But I just. I need to pursue this, like, just for the sake of my own life. Like, I just want. I just want to have, like, a nice, good conversation with this person to just be. It will just be a satisfying thing. And I have some ideas of what I. How I can be useful to him. Anyway, point is that, that, like, the guy responded to my initial email. This wasn't cold, this was warm, because there was a warm intro. But point is, he gave me a cell phone number and then we texted for a little bit to try to get in touch, but he's touring and it's really, like, it's really hard. And I have just become engaged, increasingly afraid of being a burden to him. And so I let months go by between outreach and. And like, you are doing the opposite. You're just like, maybe you didn't see email or what about WhatsApp? You didn't see WhatsApp. I'll like, send a carrier picture. Like, you're just hitting at every place. And I just like, where is that coming from? How are you? How are you not being afraid to do that?

[Jenny Wood]

Getting over truths and tales. So truths are the facts. Like, here's what's actually happening. Tales are. What are the stories I create to make sense of the facts or the truths. So truth. I reached out twice. I didn't hear back. Tales, Unhelpful tales. He doesn't like me as much as I thought. We're not actually friends and we're not, you know, we're like acquaintances. We're not like close friends. I am embarrassing myself. Like, he's rolling his eyes at me, right? Tail, tail, tail. Like, unhelpful stories. So I write a new story and sometimes it takes your community to help you, right? Our mutual friend was like, no, he's just so. It's like, jenny, do you know how much email and how many WhatsApp messages Ollie gets? Like, are you kidding? She's like, reach out again and tell him you'll go to Hong Kong. Right. So it's reframing from I am worthless. You know, he's rolling his eyes at me. He thinks I'm a joke. He's laughing at me. And I'm just like one of every other person who asks him for a favor to. Actually, he probably gets a thousand messages a day. He didn't see it. Yeah, actually, when his business manager did write back, his general manager, he's like, sorry, Ali was traveling all of last week, so sorry for the delay in getting back to you.

[Nicole Lapin]

Yeah, he didn't see it. It's true. That's probably just the case with that musician who I love. Like, I, I. Last time I texted him was about two months ago, and I didn't hear back, and I've been afraid, and I. The answer is he probably was just, like, on vacation or something, and he just. He got 3,000 texts that day, and he just. Just didn't get back to mine. All right, Jenny Wood, author of Wild Courage Go after what you want and get it. I feel inspired. I feel inspired to cold outreach somebody. I don't know who it's going to be, but they're going to ignore me, and that'll be okay.

[Jenny Wood]

Cc me on it. I'm psyched to support you so that.

[Nicole Lapin]

You can reply for me. Help Wanted is a production of Money News network. Help Wanted is hosted by me, Jason.

Jason Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our [e-mail] for the chance to have some of your questions answered on the show and follow us on Instagramoney News and TikTok MoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

[Jason Pfeiffer]

Oh, I didn't sign up for that.

[Nicole Lapin]

All right, well, talk to you soon.