mastering cold outreach: my 5 P’s for success and powerful connections | Seed To Harvest Ep59

I think like one of my favorite examples was I wrote a thread about how, how I was really nervous to do my first syndicate deal. And it was, it was scary. Like I'm gonna talk about it on Friday, but like I worked through 2 hurricanes and food poisoning and really shitty wifi to do my first syndicate deal in a company called Pallet in November of 2020. But I, so I, I wrote about that experience and I wrote about being nervous. To ask people for money because it was my first time fundraising. Hello everyone. Welcome back after a brief hiatus due to planning for my annual meeting, which is this Friday. We have over 30 portfolio company LP and friends of the fund coming to San Diego, which I'm really excited about. Uh, but yeah, sorry there was no Seed to Harvest. Also, I have a favor to ask. If you like this podcast, if you've sent me an email about it, If you are like, damn, you know what? I like this a lot. Please write a review on whatever podcast platform that you listen to. I would really appreciate it. Okay. So anyways, I wanted to do something a little bit different today. I wanted to talk about one of my favorite subjects, which is cold emailing. I have 5 Ps because my name's Paige. So that makes sense. 5 Ps of cold outreach. And at this point in my life, I'm pretty much like a professional cold outreacher. And I also get a lot of cold outreach from founders, folks looking to get into venture. And cold outreach is really what built the foundation of my career, whether that was an email or a Twitter DM or LinkedIn. And so I wanted to talk about the 5 Ps. So first we have perspective, purpose, process, prep, and post. So let's start with perspective and I'll share some fun anecdotes from my cold outreach, cuz I feel like it's been really cool, the people I've gotten to talk with. Okay, so perspective. A lot. Okay. I, I've been, I was thinking about this. I was at a yoga class and the woman next to me, we started chatting after class and she was like, oh yeah, I'm like going to Nepal next week to climb Everest. And I was like, you're what? And I kept thinking about like, people who do all of these incredible things live on the same dimension. You know, they exist in the same dimension, even if you're like looking at them through a screen or you're watching an interview on Bloomberg or you're watching an interview on Forbes, like they exist in your same dimension. And I think one of the things that's really cool about the internet is the internet enables you to talk to people who have You know, climb the highest mountains or raise billions of dollars. Like they're literally just an email away. And so I want to provide that perspective. And then also they get asked for stuff all the time for meetings, for money, blah, blah, blah. It is so nice to receive an email that's just like, hey, I, I love your story. I love what you did. Just wanted to share that. Hope you're having a good day. I get an email like that. I'm like. That was so nice. That just made my day. I'm putting it in my little impact Google folder. And I think that sometimes it can be kind of scary to reach out to people who are successful, but the truth is everyone puts their pants on the same way in the morning and we exist in the same dimension. So act like it. I, I think that I started doing cold outreach when I was in, probably in college, and I read this book that I really liked by Beth Comstock. Who is a GE executive, and I wrote her an email, and I'm going to talk about this in purpose. I wanted to reach out to her and share the impact that her book had on my life. She wrote a great book on entrepreneurship, which is entrepreneurship within a company. I was working at Northrop Grumman at the time, and a lot of what she was saying about how you can be an entrepreneur within a larger corporation really spoke to me. But I basically was like, hey Beth, I loved your book. Here's, you know, some things about me. I'm a student at SDSU. I'm working at Northrop Grumman, and I think that your book was really impactful for me, and here's how I'm applying it in my work today. And then I was just like, you know, no ask, just thought it was cool, thought I'd share. And I think she ended up emailing me back like a couple days later and was just like, hey, thanks so much for the note. And that was so cool to me. I was like, Well, I'm just like a college student. I wrote someone an email and they got back to me. And now like flash forward to today, I think like the value of cold outreach continues to compound because now as I've built credibility and I've done things like, you know, built a venture firm, managing millions of dollars, investing in all of the amazing founders that we get to back up behind Genius Ventures, being on Forbes, writing a book. Et cetera. Now I have more credibility to add into my cold emails and the responses get even like faster. So for example, there is an investor who I've wanted to interview who's on the Midas List for Seed to Harvest, and I just sent her a cold email and I was like, hey, here's my story. I'd love to have you on the podcast. And she replied literally like maybe in 4 hours. So I'm really excited to have her on and I'll share. Who that is when she comes on. But one of my goals is to interview the, all the women on the Midas List. That's my seed to harvest goal for the year because I, there's just some really incredible investors on the list. Okay. So purpose, like have a purpose in mind. And I think too often we can think about how purpose needs to be something more than just a thank you. But I think in this world, like You can never have too much gratitude and you can never have too many messages saying like, hey, this really impacted my life, or hey, seeing you represented in this way really changed the way that I saw myself in this industry. So purpose can be gratitude. Gratitude can be purpose. Okay, process. So you can do cold email in a couple different ways. Like if you're doing it for sales or you're doing it for fundraising, what I'd suggest is building a list of people that you want to reach out to. Put it in Google Sheets, put their names, put, you know, find their emails. There's a bunch of different ways to do that. Um, there's some blogs I'll link down below, but have their emails and then go through. And what I would recommend is like either listen to a podcast or read a transcript of a podcast that they've done. Pick out a couple things that resonate with you. And I think this works best when you have 3 specific bullet points of things that they've done that resonate with your story. Because if you have one, when I read it, like when I get an email like that, I'm like, oh, that's cool. Like they did, you know, some research. But if they pull out like 3 different facts that resonate with my life, I'm like, oh, okay, this person like actually did their research and I am interested in having conversation and responding to their email because there was a level of depth and respect. Like that's what I feel. I feel like Respect when, when that happens. Um, so I'd say pull 3 different things that resonate with you, put them in bullet points on the next column of your spreadsheet. And then, you know, do this for, depends on your purpose. Like, like I was saying, I think you can do it individually. If you read something that speaks to you, write a quick email and just be like, hey, I really love this. Here's why. And that can be a process in and of itself, but if you're doing it for More sales-oriented or, or fundraising, I would definitely recommend doing it in a batch way so you can have— it also enables you if you want to like hire someone to help you do cold outreach, that's a process that someone else can do for you as well. Sometimes the resonance part is like very personal. So I would recommend doing it by yourself for a while before you hire someone. And then. Go through and write an email. It's also like, it doesn't have to be perfect. Make sure your spelling and grammar is good, but it doesn't have to be perfect. And I think someone will get like the vibe, like that's what you're really going for. It's like when you, when you're writing an email, think about the person that you're writing to and you're like, okay, how do I want this person to feel? Like, and you can imagine them either having like a good day or really bad day. And you're like, okay, I want this person to feel. Appreciated, and I want them to. I just want to be able to express like my appreciation for them. Um, so that is what I would say in terms of like the process side of things. And then for the prep, I think I originally did a cold outreach job in 2020, which is incredibly popular. It's been shared like hundreds of times. People still reach out to me today and say like, "Hey, I got a job because of this." I got You know, I started my own syndicate. I like got in touch with someone I never thought I could get in touch with. And so the prep on this was like the prep for the call, which is, I would, I would consider like personally now I would change my call to action instead of like, let's hop on a 5 to 10 minute phone call to asking them a specific question about something that has been on my mind. I think that that has a much higher response rate anecdotally than let's hop on a call. And now being on the receiving end of a lot of those emails. I think that whenever someone asks me a thoughtful question, I'm like, oh, okay, cool. This is gonna take a couple minutes to respond to. I can make other content about it. And so this is very valuable to me versus like, I would say it gets, it gets a little bit more challenging to like hop on a call. But I, I mean, I still do it when, whenever I get like really interesting cold emails. So that, that prep I would extend and have, you know, maybe 5 bullet points of things that resonate with you and 2 specific questions so it, then when you go onto the call, You have a little bit of context and you also have a purpose and it's less scary. It's kind of like, I liken it to like if you go to the grocery store when you're hungry and you don't have a list, it's kind of a lot. It's, it's just a lot. But you go and you have a list and you're like, okay, cool. I got a mission. I can do this. And so I think that in this case, doing that prep for the call can make it less intimidating to talk to them, but I've definitely been. I think like my, I, I did this for Anne-Marie Ko, who is a founding partner at Floodgate, and she's also on the Midas List. I wrote her a cold email because I wanted her to write the foreword to my book, Seed to Harvest. And I just remember being on that call and just being like, pardon my French, but like scared shitless. I was like, oh my gosh. And so, but I had had like my prep work done and so I had like different things that I resonated with her on, and I had some questions to ask her, and I had like, my main purpose was to ask her about the foreword for my book. And I just remember like, I was like shaking. And then she was like, yeah, I would love to do that. So I think that was a really cool example of, um, you know, a, a time where I was nervous about doing cold outreach and then it ended up kind of magical. And so yeah, I would recommend doing the prep so it's less scary. And then the last thing is post. So I think this for me has been meaning like keep in touch with a person, or I love when I write a cold email and then I'll respond to it like 2 years later and be like, hey, like update. You know, I, I did all this stuff and I, I so appreciate you responding to this email. I think like one email in particular that was really special to me was I was emailing back and forth with this investor, Mike Dempsey, who's a GP at Compound in New York. And I was emailing back and forth. He had tweeted about some article he was looking for, and so I took it upon myself to go and do the research. It was a really interesting article on social capital, um, talking about how in Silicon Valley, angel investing builds social capital and It talked a lot about how if we can extend that to other ecosystems and have angel investing build social capital as well, then there becomes like a more robust early-stage financing environment, which I thought was really interesting. So I sent that to him and then we emailed back and forth a couple times, just like keeping up. I don't know, sometimes I treat email like text. Like I'll just, you know, be like, here's the thing I thought about. And then they reply and then you like have a conversation over email. And I think that the informality of that is Really nice. I personally enjoy informal email, but I ended up meeting Mike in New York after that email. I actually booked a flight after he was like, oh, if you're ever in New York, let's— would love to grab coffee. And I think he was probably the first like senior investor that I had cold emailed and reached out to. And I was like, oh my gosh, this is such a big opportunity. And also I've never been in New York. So all I just, I bought a flight kind of on a whim. I went out to visit my cousin. I saw New York for the first time. I love that city. Like, I like San Diego's amazing. New York's energy is just different. I don't think I could live there because like seasonally I, I couldn't hang as a Southern California native. Um, but I went to this breakfast with It was supposed to be a 5, 10 min— or like 30-minute coffee meeting. It turned into like an hour and a half at lunch or at breakfast in the West Village. And I remember he was talking about how him writing online had enabled him to build resonance when he didn't necessarily have like an investing track record. It got him this role at Compound. It enabled him to start investing like way sooner than he had anticipated because at the time when he had started, I think he was around My age. She was like 24, 25. And a lot of people break into venture later. Like, I'm kind of statistically impossible, I would say. I'm usually the only one on the cap table under like 25. And, uh, yeah, so I, so I think like writing online enables you to build credibility as well. And if I, I went back and looked at some of the stuff I was writing around that period and I think the combination of writing online and then doing cold outreach where like that becomes a very compounding way to reach out to people. There is a very specific combination that I've used in venture where I write like resource guides and then this helps me in 2 ways. So it also, it helps me when people write me cold emails and they're like, hey, how did you do your first syndicate? I'm like, oh. Look at this. I spent like 12 hours writing a piece on how to do your first syndicate. It's a YouTube video. Here's all the resources that you need. So it helps when people cold email me. Then it also helps when I want to cold email people because it's, it's given me credibility within these different ecosystems because I produce so many educational resources. And I think that cold outreach is useful not only if you're a student in college, not only if you're in the middle of your career and looking to make a switch, but just like As a human, I think it's really fun to like reach out to people that you admire or look up to or have contributed to your influences. But I wanna talk specifically about the job piece for a little, and my own experience. I went to SDSU. We had like one alumni that worked in private equity. Shout out Justin Motika. He replied to my cold email, but there wasn't really, I didn't You know, I didn't come from family money. There, there, it was just like I didn't have any existing connections in venture, but I knew that I needed to make them to be successful in the field. And so I just started building lists of people who are writing online that I really like their writing in the venture space. I found a bunch of them through Twitter. And then as I got bigger on Twitter, I started doing more cold outreach via DMs. And these are like even more informal than Than I would say like any email stuff, cuz it's just like, you can just, it's just not that deep. Like I think there's this expectation of like, you have to do like X amount of work and it has to be like this long and it has to be super formal. But I would just like write pieces and then DM people and be like, hey, I liked, I liked your thread, or I liked your tweet, or this made me laugh. And then a lot of times they would reply. And I think like one of my favorite examples was I wrote a thread about how I was really nervous to do my first syndicate deal and it was, it was scary. Like I'm gonna talk about it on Friday, but like I worked through 2 hurricanes and food poisoning and really shitty wifi to do my first syndicate deal in a company called Pallet in November of 2020. But I, so I, I wrote about that experience and I wrote about being nervous to ask people for money cuz it was my first time fundraising. And I remember Andy Wiseman from Union Square Ventures who reached out and was like, hey, I love that you wrote this piece. Like, I still feel nervous when I have sent out a term sheet at Union Square Ventures, which is like one of the firms that I really look up to. And I just remember being like, that's so cool. Like, you know, Andy's decades into his career and an incredibly successful investor, and he's writing me that like he still He still feels nervous. So I think like, don't be afraid to be vulnerable as well. And then through that, I ended up like, I had written a piece on the Grateful Dead book, The Electric Kool-Aid Acid Test, and he, Andy's like way into that music as well. And so we were emailing or we were DMing back and forth about that. And then he was like, oh, do you wanna hop on a phone call? And I so— I pride myself on being punctual and never missing calls, and I had stayed up so late working on My deck for the fund for Fund 1, and I slept through our 7:00 AM call. Um, I just remember being like, my life is over. Like I had one shot and I blew it. And I emailed him, I was like, hey, I'm so sorry. I like really wasn't feeling well, you know, can we please reschedule? And I remember being on that call and I just remember being in my apartment that I was sharing with like 3 other girls, and I was just looking up at the ceiling, and he was talking about his like experience into venture and like asking me why I wanted to do this. And, and then he ended up committing to invest in the fund. And that for me was so special because he was someone I had really looked up to. And yeah, and I think there's really cool examples on the other side. So like founders that, that I backed like For example, Neil from Beacons. I kept seeing like Beacons popping up on my For You page on TikTok, and I reached out. I was like, all right, this guy's gotta have a Twitter. And then I saw, I found him on Twitter, and then I sent him a DM and I was like, hey, I love what you're building at Beacons. You know, let me know if you wanna chat. And that was ultimately how we ended up investing in Beacons through, through a cold outreach that I had sent. So it's like you never know what you're gonna get. Oh, and also there's like this cool. I, I feel like I had read a lot about how Mark Cuban responds to his emails, but I ended up emailing him and I was just like, hey, here's my story. You know, what books are you reading? That's one of my favorite questions to ask people, cuz I feel like you often see like the person and like you see their persona, but I think sometimes even more interesting than that is like, who are their influences? Like, who do they look up to? Who do they wanna emulate? Once you're at that point in your career, like what, you know, what are you shooting for? And that was really cool too. He ended up replying in like a day or something and, and was just like, hey, here's, you know, here's what I'm reading. I'm reading a lot about AI. And so I think there's just been so many incredible experiences that I've had through being proactive, through sending that DM, through sending that email. And so I would definitely encourage you to do the same. I know this was like a little rambly, a little all over the place, but I hope you liked it. And I hope you have a wonderful week and thanks for listening. And please leave a review if, if you like my podcast, I would really appreciate it. Special thank you to producer Riley Jennings and podcast editor Tate Doherty for your help on this episode. If you're listening and you'd like to connect with me, follow me on Twitter or LinkedIn, Paige Finn with 3 N's. Thanks again for listening. I really appreciate it. You can look out for new episodes every Monday at 5 PM PST. And if you'd like to learn more about the strategies and tactics of seasoned institutional investors and rising venture stars, check out our YouTube channel at Seed to Harvest. Also, my TikTok channel is Seed to Harvest, where I post a lot of behind the scenes. Um, and if you like this episode, please rate and review this podcast wherever you get your podcasts, if that's on Apple or Spotify. Anyways, thank you so much for listening. I hope you have an awesome rest of your day.