Michael Jaconi is the CEO of Button, with a long career including executive roles at Rakuten and a stint as a presidential campaign aide to John McCain. Authentic, meaningful relationships have been a throughline across his expansive career—and he offers a load of helpful tips on how to build them. Check out this episode for nuggets including the best jobs to get out of college, the three strongest paths to connecting with a VC, and how to avoid a major networking mistake the first time you meet someone.
Michael Jaconi is the CEO of Button, with a long career including executive roles at Rakuten and a stint as a presidential campaign aide to John McCain. Authentic, meaningful relationships have been a throughline across his expansive career—and he offers a load of helpful tips on how to build them. Check out this episode for nuggets including the best jobs to get out of college, the three strongest paths to connecting with a VC, and how to avoid a major networking mistake the first time you meet someone.
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"I think that a lot of times people just let life go by with their usage of time, and the most finite thing we've got is time. So how you can spend it and who you value is really important." -Michael Jaconi
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Episode Timestamps:
*(01:37) - Sharing your passions and vulnerability
*(04:11) - How Micheal’s fishing passion lead Don Garber to join the board of the Billion Oyster Project
*(06:16) - Securing a connection with Mickey (Hiroshi Mikitani), Founder & CEO of Rakuten
*(11:03) - Why grit is paramount, and the best transferable skill
*(16:20) - How Mark Lore provided a valuable introduction for Michael
*(18:18) - Why working for presidential campaign or startup gives you opportunity to ascend ranks
*(26:25) - Finding a more intimate way of staying connected
*(35:41) - Why its important to listen, be curious, and understand the passions of people
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Sponsor:
Who Got Me Here is brought to you by Connect The Dots, mapping professional relationships so you can find the strongest connections to the people and companies you want to reach. Visit ctd.ai to learn more.
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Links
[00:00:29] Annie: I am here with Michael Jaconi. He is the Co-Founder and CEO of button, a mobile commerce technology company. And previously Michael was the CEO of Rakuten loyalty, which he built from an early stage all the way up to a multimillion-dollar business in under two years.
[00:00:48] Annie: And he led Rakuten's hundred million dollar investment in Pinterest, super interesting. Michael also had a previous life in politics and is a lifelong entrepreneur starting his first company at the age of 16 and founding companies across marketing technology and public affairs ever since. We're psyched to have you on the podcast today.
[00:01:08] Annie: Welcome Michael.
[00:01:08] Michael: Thank you, Annie. It's a pleasure to be here and excited for the conversation.
[00:01:13] Annie: Amazing. So you've worked in so many different industries. I'm really curious to hear, has your approach to networking shifted at all across industries or has it been pretty consistent throughout your career?
[00:01:27] Michael: I believe that the networking dynamics that will be most successful in any category of business are really tried and true in that being authentic, sharing your passions, sharing vulnerability, and being yourself, you know, hopefully not being a jerk.
[00:01:43] Michael: Those things will ultimately prevail. One of the things that I've been keen to do whether networking with folks in my peer group or folks that are echelon far superior and above where I am and probably will ever be, is to treat them like humans and love to learn about the things that drive them and motivate them because.
[00:02:05] Michael: Even if they're a billionaire and founder that has gone on to public markets and massive success, the head of, uh, country or a movie star, all of them share the same thing that we do, which is passions, interests, vulnerabilities, fears. And so if you can connect on that level, a lot of times you can build deeper relationships than just something transactional.
[00:02:28] Annie: How do you approach that? How do you connect on that level with folks? Cause I know for many people looking to build relationships, going from the intro to a real meaningful connection can be intimidating. People can feel uncertain about it. It seems like it comes really naturally to you.
[00:02:47] Michael: I think one of the things that's really important is you have to have confidence in that.
[00:02:52] Michael: In yourself and in your convictions around what you love to do, and you can expose a little bit of that and expose a little bit of vulnerability. And I think oftentimes people warm to that. And then one of the things that I think is really important is just asking questions and understanding what motivates and really inspires.
[00:03:09] Michael: I think a lot of times when people are networking, they're trying to get too much out of their first convers. They're trying to get too much accomplished, too much progress down the field. And I think that one of the ways that networking really pays dividends over time is not trying to get anything oftentimes just getting to know.
[00:03:27] Michael: And I think a lot of times, if you can act and respond in that way, you'll end up having a stronger relationship. As a result of that. I know that one of the examples that we often cite when we're giving people advice in the venture community, you know, on how to raise. One of the best things in the world to do is not to just call the venture capitalist when you need something, but call them to grab a coffee, call them, to hear how they're thinking about a specific category trend that's emerging.
[00:03:55] Michael: And if you can do that and build connections that are on stronger footing than just asking and transactionally trying to get something, oftentimes those relationships in that networking will be strong.
[00:04:08] Annie: Do you have an example of that from your own experience?
[00:04:11] Michael: So, one of my favorite people is the commissioner of major league soccer, Don Garber, and Don and I were connected in a few different ways.
[00:04:19] Michael: And it turned out that he and I share a passion for fishing. and as a result of our shared passion for fishing, we ended up becoming frequent shares of the various activities that we were doing on our boat, out in the water. And as a result of his sharing of his love and passion for that activity, I joined the board of one of New York's coolest nonprofits, called the Billion Oyster Project.
[00:04:45] Michael: And the Billy Oyster Project got a really impressive mission. It's trying to restore the help of New York Harbor and doing so through education initiatives. We run a vocational high school on governor's island, as well as help restore the Harbor. And I joined the board a few years ago just because of my passion for the cause and the organization and my passion for the water.
[00:05:05] Michael: And as a result of Don and I's connection over the water. And the fact that largely unknown Don went to a vocational high school. I just had Don join the board of the billion oyster project. And all of that came from exactly this type of interaction and networking, which I didn't look at it as networking.
[00:05:22] Michael: I looked at it as relationship building. And in this case, you know, it's paying dividends for an organization that I care deeply for, because you know, Don's at a level that maybe I'll get to one year, but far above my status. And so pretty cool dividend pay that wasn't because I was transactionally looking for something from Don.
[00:05:38] Michael: It was because I thought he'd really love to do this and aligning on that, created a lot of value.
[00:05:42] Annie: That's super cool. And I love that all of that came from connecting over. Just enjoying fishing, something so simple, right?
[00:05:51] Michael: Creative, so simple. And it was his passion and it, it happened a line with mine.
[00:05:54] Annie: Awesome. Can you share a story or an example where you have gotten access to an opportunity via a relationship? I love that story. You and Don connecting, you, bringing him into the board. What have been examples in your own life? A connection has been critical in getting access to a job or an opportunity that you were interested in.
[00:06:18] Michael: One of the big moments in my career was through, through a friend of mine in San Francisco who knew of my business, having sold to Rakuten and knew that I was in a role there. And he through his network had known that Pinterest was seeking to raise. Their series C and was considering different corporates to lead that and specifically looking in the Asian market as they had planned to expand to that market.
[00:06:46] Michael: And so that connection, that friendship with that person, in addition to their extended network, introduced that opportunity to me. And as a result through responding really quickly and having that opportunity presented to Hiroshi MCON the founder and CEO of Rakuten at the time, you know, we were able to capitalize and move really quickly to secure that investment and think pav the way for Rakuten to have a massive springboard in the us market from a brand awareness and an innovation.
[00:07:15] Annie: So that knowledge, that intro came from a friend. Yeah. And then once you got the intro, can you say more about how you were able to capitalize on that good fortune and the role that relationships played in getting that deal done? I would imagine it was probably competitive. There were probably other contenders.
[00:07:35] Annie: How did you stand out and what role did relationships play in that transaction?
[00:07:40] Michael: Well, I have to say that in this case we stood out because Rakuten and the CEO, Mickey is what he goes by really demonstrated all that Japan and all that Rakuten had to offer. In a really powerful way. We invited Ben Silverman, the then CEO and founder to Japan with Tim Kendall.
[00:08:05] Michael: And they came to Tokyo, got to see the Japanese level of service called Omotenashi where you show an ability to host and serve really superior. To anything else, I've experienced. And by capturing the essence of what Japan could represent for the Pinterest business and understanding what that company wanted to achieve, we were able to align both what we thought we could deliver and what they wanted.
[00:08:33] Michael: In a way that that seemed compelling enough for them to say yes to, to us as the winners of that round and the leaders of that round. And so it paid massive dividends for the business over a billion dollars. It's generated in value from that investment. And, you know, I'm really proud of that. And all of that was driven through networking.
[00:08:50] Michael: And honestly it's even networking internally, like having the ability to have access to Mickey. Mickey's, an incredible CEO that has a willingness to engage with his employees at all levels. And back then I was on a texting basis with him and being able to engage at that level and accelerate something without.
[00:09:06] Michael: Bureaucracy of having to go between a bunch of, of people really made that possible.
[00:09:10] Annie: Hmm. That's such a good point. And I think when we haven't spent a ton of time on, on the podcast, around networking internally within your company, when you are in a job. Yep. You know, we talked to a lot of founders CEOs who are doing a lot of through external networking to make things happen for their career, their company.
[00:09:28] Annie: But often I think people might over. Sort of the relationships that are even within their business, how could someone else replicate? Your success in building those internal relationships.
[00:09:41] Michael: You know, I don't know if I've, if I'm successful or not in that regard. I think I have, you know, like I, a lot of this is like, who got me here?
[00:09:49] Michael: Where am I? But struggling entrepreneur. No, I'm, uh, you know, what, what is, what is evident though, I think is that you, you have to always understand in all the hierarchies, in a business that everybody's got a boss even. The board or the public market or the VP. And a lot of times, you know, advice, my father gave me rings true today in all my relationships, which is try to make your boss look good, you know?
[00:10:15] Michael: And if you can, a lot of times that pays dividends. And I think in certain cases, that's a very simple statement, but at the same time, if you can live that and deliver things that are actually meaningful, To your boss or impactful to your boss or to the folks internally that are at levels far senior to you.
[00:10:35] Michael: Oftentimes that can be an accelerant for your career. I think one other thing, that's just another ingredient in my success when I wasn't the CEO, but what it is. Trying to grow into that role was that, you know, having a willingness to do anything that you need to do that needs to be done for the business to progress or for the organization to progress is really important.
[00:10:55] Michael: I always talk about a couple of traits that people need to have to succeed. Grit is the paramount to me, it's the best transferable skill, because it's gonna be tested if you're in any business that isn't just taking orders, you you're gonna have to be able to muscle through and persevere adaptability.
[00:11:12] Michael: Is really important. And then curiosity. And I think if you show that willingness internally to help anybody support anybody when need so long as it doesn't distract you from achieving the goals that you have ahead of you, that pays dividends. And I think that's something that helped me with my internal.
[00:11:30] Michael: Networking and relationship development within the businesses where I worked.
[00:11:34] Annie: Yeah. I love that. So just switching gears a little bit, I find it so interesting that you started your first business at the age of 16. Where did that sort of entrepreneurial drive and know how come from? Were there certain people who helped, um, get you started?
[00:11:51] Annie: I'd love to hear about the origin story of your life as an entrepreneur.
[00:11:55] Michael: It was really started. My father being an entrepreneur and okay. My brother was an entrepreneur and I feel that that DNA is something that's just embedded and hardwired into me and the ability to create, to employ, to market, to have all the elements of a business go through you is it's a passion for me and even early on.
[00:12:20] Michael: And then part of the other driver. I really wanted financial independence in ways. And I came from a family that was well off. And my dad, you know, was only kid in his family to go to college, but he did really well. And I didn't like the idea of relying on him. And for some reason, some chip on my shoulder from maybe being made fun of or bullied in some way, when I was a kid about not having to work or not having that be a part of my story motivated me.
[00:12:49] Michael: With almost a chip on my shoulder to prove that I could. And I still think that that holds true today. I hate asking people for things still, even in like my own networking, which, and I'm a good networker. I think people would say that about me, but I'm, I don't like asking for things because I want to earn things.
[00:13:05] Annie: Yeah. I think that's so interesting because you know, I think a lot of people think about having a network to be able to leverage it. I'm sure you have leveraged yeah. Your network in many ways to get where you are. What do you think is so uncomfortable about the ask?
[00:13:20] Michael: I've leveraged it in ways that have been low risk.
[00:13:26] Michael: I have never used my network to like. Get me out of something or to do something that I thought was not in the best interest of that person. And there's an exchange there that's slightly different. You know, I think I've been given opportunities because of the network, but I thought that those opportunities were actually in the best interest of those people or my asks to certain people are things that I think are low enough of a request that it doesn't feel like I'm using or pushing too hard.
[00:13:53] Michael: And I think there's a delicate balance there. And I think defining. Is hard. I'm trying to think of like where I draw. What's the barometer for acceptable ask versus unacceptable ask.
[00:14:03] Annie: Yeah, I find it so interesting. Cause I think this is where people can get really in their heads when, when they're quote-unquote networking.
[00:14:10] Annie: And I think it's. Interesting to go hand in hand with the value around grit, right? Because grit, perseverance, and work really, really important. And we've all been on the receiving end of maybe someone who's a little too gritty about an ask that they have, right. Kind of crosses a line maybe into being annoying or pushing too hard.
[00:14:33] Annie: How do you get out of your own head? That you take what might feel uncomfortable and try to go for it?
[00:14:40] Michael: Yeah. This is a really good question. And I think it's something that I have also chewed on quite a bit. And one of the things that I often try to do with the people that are close to me from a relationship standpoint is I don't ask them to make the decision that is really ultimately likely not theirs.
[00:14:59] Michael: I try to use their relationship to open the door so that I can get to the decision maker that I need to get to. And this is the same practice that I try to live. People ask me to have an internship or a job at button, and they're connected to me and they ask that. And oftentimes what I say is like, I'm not the hiring manager of this position.
[00:15:18] Michael: I will happily ensure that they have a meeting. And ensure that they get their chance, but I ultimately can't make that decision. Otherwise that would take away and really probably affect the morale of my team. If I said, you have to hire this. And so that's been a pretty consistent model I have followed.
[00:15:37] Michael: And so I try to equip my connections in much the same way as I want to be treated. And so it's that kind of golden rule element here.
[00:15:49] Annie: So it sounds like it's about sort of scaling the, ask to something that's in that person's full control and just keeping what they're responsible for in mind when you make the ask.
[00:16:01] Michael: And also like switching places is a great way to think about what's appropriate. Mm-hmm imagine that person coming back to you and making that same request. Could you, should you, would you, and if the answers to that are no, then you should probably recalibrate how and what you're.
[00:16:15] Annie: I'm just curious how this has played out in your own career.
[00:16:18] Michael: had a close relationship with a very well known founder and CEO. Who's probably one of the best founder CEOs of our generation. Mark Lore. Who's the founder of jet. and now the founder of everything from cities to moving food delivery systems to mm-hmm the Timberwolves. And, uh, so he is, he is as impressive of a human as there is likely in the world in terms of entrepreneurial successes.
[00:16:46] Michael: When we were starting our business, we had a couple of products that could serve at button, the jet business. Then I knew that mark wasn't ultimately the person that would make any of those decision. Yet. I knew that mark knew who at jet would be. And so, as a result of that relationship, not asking mark to make the call, but asking mark to make the intro was the path we took.
[00:17:08] Michael: And it established a really strong relationship with jet, um, that led to a great relationship with Walmart and their portfolio companies. And that was all through navigating that correctly without putting mark in a tricky situ. .
[00:17:23] Annie: Yeah, I love that example because it's someone who theoretically could wave a wand, right.
[00:17:28] Annie: And, and that happen and make it happen.
[00:17:29] Michael:. And, and, and mark is also the type of CEO who would never do that, which is a Testament to him. And may have helped me shape some of my positions here as a result. It was what good looks like. Super cool.
[00:17:42] Annie: So in addition to being a founder and working in the tech industry, You had a stint in politics.
[00:17:49] Annie: I'm so curious how you got into that and how you saw relationships play out potentially differently in that world or, or what similarities you noticed?
[00:17:58] Michael: Yeah. So I think I give advice whenever I speak to college kids or anyone debating career changes, I tell them often that they should do one of two things when they get out of school, either work on a presidential campaign or work at a startup because in either environment.
[00:18:17] Michael: You have an opportunity to ascend the ranks in your career far faster than climbing a corporate ladder. You also have the opportunity and political campaigns, presidential campaigns in particular, and startups have tons of similarities. They have a massive focus on pace of play. You have to be fast. You have to be quick.
[00:18:37] Michael: You have to be nimble. Both are trying to achieve outcomes far beyond their means. One lead the free world, the other create tons of value and unicorn status outcomes. And you never have enough resources to do. Either of those things. And as a result, that means that the people willing to go and do the extra mile, demonstrate the grit to do whatever it takes to deliver value are typically people that can climb within the ranks of those organizations far, faster than if they did that same thing at an investment bank.
[00:19:13] Michael: Or, you know, a variety of different, you know, professional motions. It's also exciting as hell to go through the process of pursuing a mission far bigger than oneself. So that's the kind of foundational layer. And I received much of that education early on from others who were mentoring me saying, try this, give this a.
[00:19:33] Michael: I had the opportunity to go work for a man. I deeply respected in John McCain and, you know, had an opportunity to be really close to him in that process. And so it was an opportunity I couldn't pass up. And in the process of getting to know that world, I became somewhat. Disappointed by just the environment of politics as we've seen in the past 12 years or so what's happened.
[00:19:56] Michael: It's not a pretty world and I don't envy anybody in that category just because it's hard. It's really hard, but it's also tough. I think it's tough for the best in our country to ultimately wanna run and lead this country based on the vitriol and where politics stands today. And I left for that reason on the networking side, the political side of the.
[00:20:17] Michael: Networking is their business. That's what they do. And everything is transacted through human interaction and compromise. And so they're not building a product, they're building a set of compromises that they're gonna sell to the world. And all of those compromises are going to be established, agreed upon negotiated through two parties or two people that have disparate views.
[00:20:42] Michael: And so. Process tends to be a little bit more transactional in my history in that realm, but the takeaways, I think, and again, I think why I've been successful building and maintaining relationships across the various industries I've touched is because I think if you maintain authentic interest in people's passions and understand what it is that drives them, motivates them that often will prevail and allow you to establish a real relationship versus a transactional.
[00:21:13] Annie: I think it's interesting. You bring up how much in politics, you need to collaborate with arrive at decisions with folks who you might not a agree with. And I'm curious from your own experience or elsewhere, where you've been able to navigate that successfully and what advice you'd have around that?
[00:21:31] Michael: So on politics in particular, I worked for a man who.
[00:21:35] Michael: No one agreed with, because McCain was so middle of the line. He had to pivot slightly during the presidential to go and win the Republican vote. And that's actually when I left, but he was a very independent thinker, very pro environment, very progra rights. He was, he was very independent thinker, not by the book.
[00:21:52] Michael: And so basically anywhere I went. I was like, you know, ridiculed in some passion, cuz DC's filled with people that have passions and often those passions are aligned with parties and this didn't really do that. And what I learned was that in politics, it's really unlikely that we're gonna change anybody's opinion.
[00:22:09] Michael: In a debate. And so a lot of times, the reason you're arguing over politics is cuz you wanna make a point for yourself to feel like you've won. And I've recognized over time that there is really no prevailing in that model. If you wanna have a debate to go fight and some people love to fight. I have a good friend, a dear friend, founder, CEO, ex trial lawyer.
[00:22:28] Michael: He just loves to fight. That's like his DNA. And, and he loves to debate and be right. And luckily I'm aligned with him a lot of politically, so I don't have to fight him, but, but it's a comical thing. And so some people that want to fight just like to fight and they go through that process. I don't think it's worthwhile.
[00:22:43] Michael: In terms of investments of time to engage in those types of conversations with people when the outcome is unlikely to move the needle. And a lot of times I'm thinking about, what am I getting out of this moment? Am I getting something out of this moment? That's valuable. Most of the time that's learning about somebody.
[00:22:59] Michael: Most of the time, that's hearing what they're passionate about, what they love to do, what they're nervous about, where the vulnerabilities lie. A lot of times when you're debating politics, you're not gonna really get much. You're not gonna learn anything. Cuz most of what they're doing is spouting. What they read either in the New York times is a wall street journal.
[00:23:13] Michael: I think another interesting thing that I recently heard and it was on a podcast by Rick, a Elias. Who's one of my favorite business people. He's just an incredible entrepreneur. He founder CEO of red ventures and no one's heard of, but now they've had some more press, they own bank rate and the points guy, which a huge brand.
[00:23:29] Michael: Anyway, Rick has a podcast and he was recently speaking. Adam Grant. And they were talking about the dynamics between red Sox and Yankees fans. And I thought it was fascinating that one of the questions that they asked the Yankees fans was that if they lived in Boston, would they be fans of the red Sox?
[00:23:48] Michael: And these people kind of stopped and said, you know what? Yeah, I pro I probably would be. And it was this interesting moment where it. To the point you were making on, you know, just politics and how people come together and talk. It's pretty interesting that depending on where you're from and what you've been through, it's likely to be the strongest ingredient in your political fiber and that if you switch positions, what would that do to you?
[00:24:12] Michael: And a lot of times that brings a resonance. That's hard for folks to understand, without trying to put yourself in the other people's shoes.
[00:24:20] Annie: Nice. Speaking of Boston, I know that you have ties to lots of different cities. It sounds like you've moved around a lot. DC, New York, Boston SF. How have you found moving and living in lots of different places and having ties to different places?
[00:24:36] Annie: How has that impacted your network and the way that you stay connected to people?
[00:24:40] Michael: I think that the network. Connections in all these cities are forged at various points in your career. My first, you know, job outta college was in DC. Then I was in Boston for four years. And then New York, since then, you often are forging are the ones that at least in, in my time now and way back when, where you have intention in intentionality behind what you're doing.
[00:25:05] Michael: And I think that a lot of times people just let life go. With their usage of time. And the most finite thing we've got is time. And so how you can spend it and who you value is really important. It's up to you to go out and like have intentionality about who you seek out to be friends with. And that's the thing that I've found for me in all these various cities, where I've connected with a few people in each, not with a networking orientation to it, but more just, you know, genuine interest and friendship.
[00:25:35] Michael: Those have been the people that have been the most rewarding for me to connect to, and sure it pays dividends professionally, but at the end of the day, you know, I think a lot of times the most valuable relationships are the ones. You're not really out there seeking for value sake, more that you're seeking for what they nourish and what they give you as a friend, if you can take that.
[00:25:54] Michael: And if something happens as a result of that, I think it's all the better. And
[00:25:57] Annie: how have you stayed in touch with people across these geographic lines? You know, I think things are different now, obviously the rise of remote work and we had this two year period where everything was virtual, but do you have any advice for how to.
[00:26:14] Annie: Maintain those relationships, even across distance. Um, cuz I think that's something that makes people nervous. You know, I don't wanna move to this place cuz my whole network is totally in this other city.
[00:26:25] Michael: Well, I know, I know a couple things. I was more intentional about like making a splash in New York.
[00:26:29] Michael: When I got there, like I was going to events, I was trying to meet people. I was trying to understand where the centers of influence were in the industry where I was likely to start a business. Cause I moved to New York and then started button. Then people were like, why didn't you move to LA LA was this, you know, bashing of hot startups, you know, starting at that point or why didn't you live, move to San Francisco where all startups live.
[00:26:48] Michael: Um, My business, probably would've been more successful that I done San Francisco, but at the same time, I just loved New York. And so I had that intention front to go and start meeting people and knowing people. And one of the things I did actually, and it was really successful and it's very tactical is I would just host dinners and I host dinners with I'd find a couple cool people that I really enjoyed being with that were in the industry.
[00:27:10] Michael: And then I had said if I think you're cool, other people probably think you're cool and fun and nice. And so let's get together and do a. We don't have to talk about anything in particular and those germinated into like pretty regular thing. And that was helpful. Another thing that I do, I'm not on social media, I'm on LinkedIn.
[00:27:24] Michael: That's my only social media. I'm not a big share of personal information, but I do run what I call like my private Instagram, meaning I actually don't have Instagram or don't post on Instagram, but I send. Pictures of like my family and my friends or my passion or whatever it is to the people that I know either have overlapping passions.
[00:27:42] Michael: And that's been a really, I think, more intimate way of staying connected than having someone look at your life on Instagram that you're know you're telling a story around, but Bera just say, Hey, here's me. Here's what we like text one to one text of photo. Yeah. I mean, like maybe some context, but like a lot of times thinking
[00:27:59] Annie: Of you out on a fishing trip.
[00:28:00] Annie: Exactly. Shoot it over o Don
[00:28:01] Michael:. Exactly. Yeah. Don massive striper earlier this week, massive striper sent him a photo. He responded with a massive striper that he had caught the same day. So exactly right, exactly. Right. Love
[00:28:13] Annie: it. I'd love to spend a few minutes talking about mistakes. What is an . What's a common mistake that you see other people make in networking.?
[00:28:25] Michael: I think the most common mistake that people make networking. Is they're trying to network. Mm. I just think that they try so hard to network and make something transactionally happen in the first interaction that there's almost this like seeping in of insecurity into the conversation that's palpable.
[00:28:45] Michael: Mm. And I see it a lot because people, people are grinding when they have to hit a number or get a connection or open a door. And so there's naturally nervous. then causes people to behave. I think sometimes slightly irrationally in like their pursuit of whatever outcome they're seek. And I see that happen, commonly, which is, you know, and what are the symptoms of it?
[00:29:08] Annie: How do you know it's happening?
[00:29:10] Michael: Just pushing really hard to like get to the close, whether the close is your phone number, whether the close is the, can we meet? I think one example that I witnessed one time was we were in an informal meeting with someone in one of my past businesses and guy that was like a channel partner of ours.
[00:29:28] Michael: Like brought out a pen in the. Informational meeting to sign something with a customer who was not yet a customer, but a target. And that was kind of like a zero to a hundred approach that I thought was really awkward. And so I think sometimes people try to get too much out of their first interaction.
[00:29:47] Michael: And I think the other part is people fail to maintain relationships for moments where they don't need anything. I think that's a really bad mistake. You don't. email the partner at Greycroft, just when you're about to raise money, you wanna email and get coffee and say like, here's the trends I'm seeing.
[00:30:07] Michael: How are you feeling about this? As long as you've got ways in to get into those people and they respond, that's something that you should try to do with a regular cadence. And if they don't respond to you, then maybe put a dinner together with people that they probably want to be near and then invite them.
[00:30:22] Michael: But that's kind of a navigational, you know, dynamic or tactical dynamic that I would advise. I think the, the thing that I'm advising against is like, don't just berate people or don't just ask them for your outcome when you have no relationship with. And a lot of times, you know, one of the things that you can rely on with people is people love to coach.
[00:30:42] Michael: People love to advise people love to mentor. They love it because it makes them feel good about themselves. And they also love it because it allows them to get out of the grind of their day to day, which, you know, if you ask 90% of people, they're like, oh my God, my job is so hard. And so this is like a little bit of liberation and.
[00:31:01] Michael: Use that in places. And then if you're trying to get connections, I think this is a really important networking lesson. If you're trying to get into people, let's say at venture capital firms, it's important how you get in. And I used to rank the order of how you got in, in the following ways, one in LP and a firm.
[00:31:21] Michael: If you can get in through an LP is typically the best cuz they're technically the boss. And so if you can get in through an LP, that's. the second best is an entrepreneur who has succeeded with the firm and is a current investment of the firm. So that means that they have made the money and the firm still cares about them because they're still in the portfolio.
[00:31:43] Michael: The third would be an entrepreneur who has succeeded for them. But not in the firm today. So out of the company somewhere else. And then the fourth would be a portfolio CEO today that has yet to make the firm success, but still was in the portfolio. And the venture capitalist cares about the impression that entrepreneur has of them.
[00:32:01] Michael: And that's typically the ranking of how you would get in and then I'd go to like connections to the venture capitalists on the personal side, probably last, but I think that's also a tactical element. As we're talking a lot about networking, that's been helpful and important in, in my successes.
[00:32:16] Annie: I love that you bring that up because that was one of the things I wanted to ask you about.
[00:32:20] Annie: You've been really successful in raising venture capital funding. And, you know, you've mentioned in the conversation reaching. And building the relationship with investors before you're raising. Could you just tell us more about the role of relationships in raising investment dollars and venture capital specifically and how other people should think about that?
[00:32:43] Annie: If that's an aspiration they have
[00:32:44] Michael. Yeah. I think it's a really important dynamic where you are going to ultimately get your time in court by being able to open that door. And so having the ability to. Connect with the venture capitalists on a level that isn't just one of the thousands of pitches that they get mailed to them every day is a really important dynamic.
[00:33:08] Michael: And so everything that you can do, and a lot of that starts with if you've never raised money and never had an outcome before. Then it's gonna start with in room meetings in conference rooms, in conferences and at dinners that you're gonna establish those first connections. And then it's up to you to try to differentiate yourself from the folks in the room.
[00:33:28] Michael: And ideally you do that through being a great person, a great listener and understanding what that person's passions are and how, you know, you have something to offer them. Then you really just have to hope that your business is trajectory and momentum. Is such that it will open a door, uh, to that investor.
[00:33:47] Michael: And one of the funny lessons I've had is like, oftentimes the worse you treat an investor on the pre-funding basis, like the better they treat you, not actually saying go be a jerk or anything, but you know, a lot of these people, this is a game of FOMO. Fear of missing out. And so that's a dynamic that I've seen a lot of entrepreneurs play very well with their raise process.
[00:34:09] Annie: Do you have an example or a story from an investor relationship that has been critical for you and, and your
[00:34:16] Michael: success? Yeah, I mean, our business was really affected negatively by COVID and Chris Moore from red point led our series a and has been and become just an incredible. Source of support for us at one point, you know, a really challenging path ahead.
[00:34:33] Michael: And we had to make a lot of hard decisions and that experience that he was able to bring to the table alongside Jeff Crow and Jeff Miller and Greg Coleman, the other board members, they've seen a lot more than I have. And so what we were trying to understand is like how, and what do we do in this scenario where everything looks so bleak.
[00:34:51] Michael: And I will tell you every one of those. Guys we're such incredible coaches and sources of support for me that like I mentally, I was in a really dark spot. My wife had just had our second baby. We were in, you know, just having a ton of tough times on a variety of dimensions and this was happening. But with the business and the board really pulled together and, and gave support.
[00:35:12] Michael: But also the coaching as to how to navigate in uncharted waters. And I thought that was incredible. And I, I don't know if I would've received that same level of support. Had I made other decisions early on from which investors we worked with.
[00:35:26] Annie: Is there a single most important thing? That you would leave our listeners with, if you had to summarize the single most important thing for folks to keep in mind or to do or avoid if they want to build and make the most of their network.
[00:35:41] Michael: I think, listen, be curious and understand the passions and the vulnerabilities of the people around you and the vulnerabilities isn't so that you can exploit them the vulnerabilities are that help them understand how to navigate and the passions, because everybody has a passion. And so when you find that, oftentimes it can give you something really fun to talk about and to share experiences on and share stories about.
[00:36:08] Michael: And it probably gives you something to call back to. That gives you an opportunity to share and connect and say, Hey, I'm thinking about you because I know you're gonna care about this. I can't tell you how many people, when the wall street journal wrote recently, Dolphins were swimming in New York Harbor.
[00:36:25] Michael: I had like 45 text messages from friends saying, congrats, isn't this amazing. The billion oyster project is doing its part. And that's another example of that.
[00:36:34] Annie: Awesome. Well, you're gonna get some fishing photos from me. Now. We know the way to connect with we go that's with Michael is that's right.
[00:36:44] Michael: Striped bass, photos, tuna. Actually my grandfather and that whole side of the family were tuna fishermen by. That was what they did. So I think all my grandfather used to say was. He just wanted to make enough money to not be a fisherman. And all I say is, all I wanna do is make enough money to be a fisherman.
[00:37:02] Michael: So that's amazing. Little, little irony,
[00:37:05] Annie: Michael, thank you so much for joining us today. This has been a really enjoyable conversation. I think there are many takeaways that our listeners will be able to use. Where can people find you who want to learn more from you? You mentioned you're not on social media.
[00:37:20] Michael: I am on LinkedIn and. The most regularly updated media that we use, or you can check out what we're doing at usebutton.com or the billion oyster project and see all the things that we've got moving.
[00:37:33] Annie: Amazing. Well, thanks so much for joining us today. It was a pleasure having you on.
[00:37:36] Michael: Thank you, Annie. See you guys.