🔴NEW EPISODE: Wine, Music & GTM with Michael Nathan 🎧

Speaker A: Live. And we are live. Hello folks. Welcome to the Connection Loop podcast. Today I'm um, with Michael Nathan and we, we've got something we, we just explored so much. We had, we had an initial plan to talk about GTM and business and technical founders and how they can scale. And we realized that the only way to communicate this information is to use the tangents of the passions that we have that we share in fact, music and wine. So this podcast so far is called Wine, Music and GTM with Michael Nathan. Michael, if you could please kick us off with an introduction. Tell us about your background, tell us about your, your, your primary life and tell us about your behind the scenes life and how you've integrated them both into one.

Speaker B: Oh, uh, I love it. Well first of all Ruben, thank you for having me. It's uh, great to see you and I love what you're doing. So um, background. 22 plus years in large enterprise, Apple, Cisco, HP, Microsoft. At Microsoft I ran global partnerships with eBay, PayPal, Dropbox and Intuit. At Apple I was part of the team that launched the initial iPhone back from 05 to 09 era. And I ran Northern California higher education sales here in the Bay Area. Um, I ran for eight years at three different companies, Network Appliance, Cisco and hp. To the executive briefing center that allowed me the opportunity to hear from the company's best and brightest, from the CEO to the executives under his uh, or her ring on. Why do we do what we do? Why does what we do matter? And why should you as a customer, partner or a prospect, care? And so early in my career I was able to understand and fine tune the messaging and it really came down to who's going to take time out of their day to acknowledge my presence while I'm at your site.

Speaker A: Beautiful.

Speaker B: Um, yeah. And then fast forward post Microsoft, I had the amazing opportunity to join venture capital at Sierra Ventures as the Vice President of Business development. And that really entailed um, from a non investing perspective, bridging the gap between the portfolio companies, the enterprise and our partners and LPs. So things like uh, our annual summit, what are the topics that we're going to talk about that are 6 12, 18 months away. So people may have heard of it but not have had a chance to implement or bring in. And um, back then we were doing things with Dr. Jeremy Bailenson who's the professor at Stanford on the Human Interaction Lab and he had a company that was doing AR VR and muscle memory. So imagine as a football team instead of having to Go out and physically practice and risk injury. You're able to do it in an AR VR setting, get your muscle memory, everything down and no injury. M18 NFL teams brought his technology in. That's how advanced it was. It's also the same individual that Zuckerberg spent three, four months with before he bought Oculus. So it's that 2017 timeframe. Then, um, I went on to IBM Ventures. Late stage due diligence, billion dollar plus valuation companies before they go public. Uh, spent a lot of time with Eric Yuan at Zoom, the people over at Uber, uh, Airbnb. It was an amazing era. And then from there I started to be a mentor and a coach at, ah, three different accelerators that I'm still at today. Alchemist Accelerator, which is the largest accelerator to the US Enterprise. Innovit, which is the Italian government's innovation army, and swissnext, the Swiss government's innovation element, where you have at least one founder from that country that comes to San Francisco for a 10 to 12 week accelerated course. And they would bring people like me and to be mentor coaches. All the topics around go to market, product, market, fit, capital, uh, raise readiness. And what that means is I'm not going to raise the capital for you. You're the CEO, you're the founder. Let me help you get ready to raise it yourself. Let's really talk about your story. Who you are, what you do, why it matters. How did your team come together and why is your team the best team to address this pain at this time? Those are the things that I try to help founders tell their story. Typically a technical founder, very monotone. There's no excitement. And if you're an investor, uh, why are you investing if you're not excited about what you do and why it matters? So I try to help them a little bit, not to be animated. I'm on the other side. I'm overly expressive. But, um, as a founder, I need them to be a little bit more passionate.

Speaker A: That's a beautiful, that's a beautiful story. I really appreciate that. And you play the congas?

Speaker B: I do. I've been playing congas for over 20 years. Um, so it started this way. Network appliance. I was in line for a really nice bonus. I was going to buy a ridiculously big watch. Twenty years ago, every time we're at the stop sign or the stoplight, the Gap Band or some R B music would come on and I'm playing percussion on the dashboard, uh, my wife said this, um, congrats on the bonus. Instead of Buying that watch. Why don't you go buy some drums, put in the garage and play it when we're not home. But you got to stop playing the dashboard. Uh, so that was a trade off. I bought the most expensive set I could buy, only for guilt. I didn't want it to sit there and collect dust and not get paid. So I made a promise that within 16 months, not 18, but 16, I'll start getting paid to play. And I'd never played before, like an actual Congo percussion. It worked out. Local restaurant had a band. Every Friday. I got to start playing for tips and being Indian in Fremont, most of the doctors are Indian. They started to come in. My tips exceeded the band's salary. So.

Speaker A: That's amazing. That's, that's super cool. Um, isn't it, isn't it interesting how sometimes someone else sees something in us, uh, that we can't see for ourselves, but it's just so blatantly obvious. And you know, there's this, there's this thing that I really love to explore, which is effortless action. And effortless action is the idea is the Woo way. And you know, you see someone that's been doing Tai chi for decades at the park, and this is absolutely effortless. The way that they move, the way that they carry energy and project energy and receive energy and glide their body through time and space, it's absolutely effortless. And that comes from a tremendous amount of passion, but also, ah, repetition, you know, and as a drummer myself, as a musician myself, there's some, there's some guitars behind me and tons of drums at my house. You know, there is something that occurs when I play music, which is that it becomes absolutely effortless. And the thing that I enjoy most in life is the things that are effortless. And I'll tell you this, managing my GTM is not effortless. Okay? As the CEO of an AI powered software company, GTM is something that I can't go back to my trusted Gibson guitar or my Ludwig drum set and play on it and it feels like it's play that, that like, it's like it felt since I was a child. GTM is something that we're constantly changing and building and breaking and adapting and realizing the algorithm has changed and that these new creatives need to be used in our ads. And we're constantly on this journey and, and, and I've found this balance in my life where I have. I have to heal myself with my Wu way, with my repetitive effortless actions like music, like playing pickleball. Like enjoying myself on a bike rider, walking. But then on the flip side, my day job, you know, as, as a founder is, is navigating this treacherous battle zone where, where we're constantly trying to change our dynamics so that we can scale. I would love to get your advice on how folks can find this balance of, you know, dare I call it war and peace.

Speaker B: So let's understand the definition of go to market first, right? And then let's map it to the passion of the balance. For me, you know, go to market is the comprehensive business strategy first and foremost, and it outlines how organizations introduce their service specifically to their target market. Right. Um, how do you achieve the competitive advantage? And then how does sales adoption factor in? So go to market at that highest level is what it is for me when you map it to, let's say, music. Right. For me, it's about harmony. There's a harmony, uh, there's a hook, uh, there's a chorus. And that, at a high level really integrates well with things like go to market when you have multiple sections. Competitive advantage, product market fit, um, authentic voice of why you do what you do, why what you do matters, and why should the audience, customers, prospects, or, excuse me, partners care? And if you can, uh, storytell that in a single thread at a high level where anyone can understand it, that's the definition for me. So I keep it at a high level so we can find synergies and then we double click. Let's really dive deep on what are you passionate about with respect to outside of this? Um, and then how does that correlate relate, differentiate your go to market strategy? And for me, go to market and product market fit literally go hand in hand. M. So let me pause and make sure. Uh, I'm addressing your question.

Speaker A: Yeah, well, here's, here's what I really appreciate what you're saying is that there is this nomenclature that I think mostly technical founders have started to implement. And I noticed that, um, when we understood it's like the acronyms, we love to use our acronyms, right? Gtm, icp, you know, and one of the things that I always try to understand is product market fit, which is not really, um, an acronym, but let's call it, you know, pmf M. I don't know if I've ever heard someone say that your product market fit, but let's just say that that's one of the acronyms. Right?

Speaker B: Okay.

Speaker A: Your pmf, um, and you have this sort of vernacular that's sort of, you know, floating in space and, and As a, as a business person, forget technical, forget founder. Just as a business person that's looking to connect with people and grow, how can I really understand how I connect these two things? There's my product, there's what I sell, there's these people that I want to sell to, and then there's this alignment that I get and this mechanism that I connect my product to my people. And if you could sort of unpack and unravel how one might be able to look at their business, whether they're a technical founder or not, I would love to get your take on that, how you can look at that. Like, if I were to, you know, one time someone said draw your business, I was, it was actually a VC meeting and it was the best exercise that I've ever had. Draw your business. And they literally gave me a whiteboard and I had to draw the business. Yeah, here's the target audience, here's our channels, here's, um, you know, our people, here's how we're going to grow, here's how we're going to scale. Here's our, you know, our, our sort of, our, our cycle effect of growing. And it was a great experience. So please, Michael, guide us on how we, quote, unquote, draw our business when it comes to our product, our people and making that alignment.

Speaker B: Uh, so that's a great question and a great opportunity, um, for me to share. So let's this, I always look at unpacking what's the important elements of each side in order for us to draw that correlation. The importance of go to market strategy. GTM is essentially to provide a clear roadmap for launching new products, uh, entering and ensuring coordinated effort and you have the efficient resources that are, uh, sufficient to accomplish what it is that you're trying to, um, the, the other elements are alignment and then are you able to help? Right. So is the strategy helpful in achieving not just your goals, but are you solving a pain or a problem, or are you having a differentiated enough offering that it's unique? And so when we think about drawing that balance and that correlation, it's the same thing. Let's go back to music. You know, is it, is your music different enough or is it like everything else on the radio? And both are fine. If you want radio play, then you play what's popular and what people are listening to. If you want differentiation and you want to stand unique, then what is your authentic, uh, element that you bring to that table? Right. So sometimes it requires you to dig a little bit deeper and you go through this conundrum of, uh, who am I when it comes to music? What am I trying to be? Who do I want to sound like? Or do I want to sound like myself? Who doesn't sound like anyone out there, but is heavily influenced by everything that's out there? Right. So if you look at Prince as an example, those that are new think wow. But those that have been around understand, that's Jimi Hendrix, that's Little Richard. Uh, there's a few elements that you see James Brown that embodies who he is today. Right. So this is why target market, product market fit come in. What, uh, is your desired outcome? Who is your desired audience? So you know how to cater and align and more importantly, speak the same language. Not literally, but is what you're saying resonating with the audience that you're targeting and I. Targeting, Right, Targeting. Loosely targeting. Meaning what's the pain or what's the thing that's missing that that audience doesn't have today? And is what you have your product, service or offering filling that void, is it better, faster, cheaper, or is it really solving a pain? Right, so two different tracks. Both are viable. You have to pick one.

Speaker A: M. Yeah, I received that. You know, there's, there's, there's three books that come to mind right now. Normally I say there's one book that comes to mind, but for some reason I got three. And the first book, the first book is, um, zero to one Peter Thiel.

Speaker B: Mhm.

Speaker A: The second book is, um, uh, Purple Cow, Seth Godin. And the third one is Blue, um, Ocean Strategy. And the reason why I'm mentioning these three books is because as a, as a founder, as a creator of a technology, as a creator of something, number one is I think how can I go to 01, which is to be a category creator? My. I like what you said about the metaphor of if you want to get radio play, you have to, you have to make music that sounds familiar to people. And the same thing goes with technology where if we want to have a tool that people want to consume, it has to be something that there's a category for that they want to use, that they probably have something that they're currently using that's broken and that they want to fix. And I think that that's the first thing. But at the same time I think it's really interesting to want to come and say, I'm going to do things absolutely differently and I'm going to do something really neat. Like you look at Sora, you know, and you look at this AI generative tool and it's like AI social network. I haven't seen it before, mind blown, but it's familiar. And then the idea of a blue ocean strategy is, is go and create something that's unique where you don't have competitors around you. You've created this moat where it's uh, people are, companies are two years behind to come and beat you there. And Purple Cow is, you know, is, is unique. Being different, being unique. My question for you is, how do we find this balance of being unique but at the same time being consumable?

Speaker B: Yeah. So, um, it's like prompt engineering. You have to have a desired outcome in mind. You have to have a vision of what it is you're, um, trying to do and what does success look like. Right? So growing up it was always, you know, you have to have a plan,

Speaker A: write down your goals that, that my dad would always say that rest in peace. You gotta have a plan, son.

Speaker B: Um, because you have to have some direction of where you're going, otherwise you're wandering aimlessly and you never know if you're arriving or if you're getting closer or not. Right? So the whole point is, if you have that plan, when you fail, which you will, you'll fail a lot further ahead in the direction of where you're going, rather than, you know, the equal distance on the left which isn't in alignment. So, uh, prompting is this. You have a little space to write, typically 26 characters at a time. And people get bogged down by the limitation, the perceived limitation, but you literally can write thousands of characters in that space. If you have an idea of what desired outcome looks like, then you can feed and uh, provide information with specifics that will help, um, guide your journey, if that makes sense. For example, if you're in a Tesla or an electric car and you're going to go a 400 mile drive, typically you're going to need to make a stop to do a refill or a charge m. If you don't ask it to say, hey, find the most, um, efficient charging station with the most charging units at the highest megawatts or whatever the frequency is. So I can minimize my time, my downtime, map the trip that way versus pulling off of every other exit looking for a target or a Costco, uh, to plug in. That's the difference. You can achieve that and you can arrive faster if you have an idea of what you're trying to accomplish. So the point being, uh, have a goal, have a vision of what Success looks like or desired outcome and then feed it as much information as you can that would augment and differentiate your pathway there.

Speaker A: M. Well, I really appreciate how you embrace the idea of desired outcome. And this is, um, this tells me that you are hyper focused on goal orientation and reverse engineering. And I think that um, a lot of us don't do that. And I know that I am guilty of this, especially lately because there's been so many changes in advertising specifically that I have become enamored with the process and it has become a daily challenge where I feel like I just want to overcome this. And sometimes I lose sight of what is my ultimate desired outcome as a technical founder. Is it an exit? Is it, Are we getting um, are we acquiring another company? Are we getting acquired? Are we merging? What does that look like? What is our outlook of 5, 10 years? What does that horizon look like? And I really appreciate how you're reminding us to think desired outcome. Reverse engineering. And then now I think the third step is the specific daily, weekly, monthly tasks that we need to take to go scale. I always like to talk about what's the difference between scale and growth. Scale does not require additional inputs, growth does. So scale is a lot sexier because it's a lot more efficient. But now I think on this third canon is how can we go and develop a strategy, a plan? How can we go create that plan? Plan. What is our prompt to map, to map us out for our desired outcome?

Speaker B: Mhm. Uh, so at Meritage Group, where I work with startup founders, entrepreneurs and what I call builders of the future, those that are building with tomorrow's technologies today, I do a few things. I do a 30, 60, 90, uh, roadmap, I do a SWOT analysis and then I look at a two year roadmap. Each quarter is a milestone, so there's eight quarters in that two year roadmap. And we start with desired outcome and work backwards. Reverse engineering, like you just mentioned, each quarter is a achievable milestone that we're aiming towards and it gives us a 90 day. Are we on target? Are we going to hit it or miss it by 90 days? Right. So we don't have to be so precise, but we have to be typically within a quarter of execution of each step. And in a two year roadmap, working it backwards. And if you're raising capital, it gives you a really good understanding of the Steve Jobs element, which was at the very end of his presentations. He would save that wow factor with. Oh, and by the way, one more thing.

Speaker A: The Prestige of the magic trick, Right?

Speaker B: So the point of this being your first six, seven quarters should be more conservatively aligned on, um, how you spend the money that you're raising. Typically, there's a big story of development, uh, and engineering and all that, but it goes towards headcount. Right? We all know that the majority of that money is going to headcount. That is not a return on investment per se. But when you have this element of surprise at the end that is captivating like a Steve Jobs. Oh, by the way, One more thing. IPhone is coming. You might pique interest to say, what do you need now to make that happen sooner?

Speaker A: What do you need now to make that happen sooner?

Speaker B: Right? From an investor perspective, if you're raising, say, $3 million and you have this conservative approach that looks like it's achievable, and you have the right team and the story to make that happen, but you have this incredible next thing that's coming. Investors don't typically invest in a product. They're investing in you. The founder, the entrepreneur. They always want to know, what are you going to do next, what's coming next? Or are you that one trick pony? And if it's a one trick pony, is it big enough of a trick that we have a sustainable path to return on investment within a defined period of time? Um, but if that thing at the end is intriguing and it piques interest to the point where they say, that is exciting, what do you need now to make that happen sooner? Uh, you have a few options. You have the ability to increase your ask of what you're raising, or you have the opportunity to quickly pivot to put more resources to make that happen. If it's something that can happen without the other six, seven quarters happening first. M. This is why that authentic story tell of why do you do what you do, why what you do matters, and why should I care? Uh, really aligns with purpose, process and benefit. What's the purpose of your company offering or solution? What's the process to get to deliverables? And then what's the benefit to you and to us? M. By recognizing it in its full accomplishment or by, uh, taking it in? So that's the beauty at that pathway.

Speaker A: And then where can we go and explore this system that you mentioned? Um, you mentioned Meridian? Can you unpack this a little bit?

Speaker B: Yeah. So Meritage, right? Meritage is named after the winemaking process. In a true meritage, you have two, if not more of the big five grapes. And, uh, for us at our vineyard, we have Cabernet Franc and Cabernet Sauvignon. We're not members of the Meritage organization, but it's the same embodiment of what constitutes a meritage. Meritage essentially is a harmony of a blend of a few other things. Right. So the name of my band is Meritage Music. It's a blend. We have percussion, we have keys, we have vocals. It's a Meritage wine. It's a Meritage. Meritage group is a mixture of the entrepreneurial spirit, the process driven experience that I bring from 20 plus years of enterprise and venture capital and the desired outcome. Right. It's the trifecta. Um, I don't promote and advertise. I try to do. What you do is have conversations to understand purpose, process and benefit is what I do. And the services I bring something that can help differentiate what you're trying to accomplish in your desired outcome. So we have a uh, somewhat of a pseudo interview first. And if there's alignment, if you like the things that I've done, the proof points and where, the direction in which I'm heading, if it aligns with what you want to do within the time frame, then let's find ways to work together. Right. It's not about money first. It's about alignment. And is it something that I can bring value to you? Because at the end of the day you are who's going to refer the next client to me M based on the outcome or the experience you have. So if I take the emphasis off of um, raising capital for you but getting you capital raised ready now it's that teaching a horse to drink and eat by themselves where you're self sufficient. Right. You've learned um, my, what I call uh, DNA of enterprise. The enterprise DNA bringing that process driven procedural, uh, elements of large Fortune 1000 companies into a 3 to 10 person startup.

Speaker A: Right.

Speaker B: Uh, it's keeping that entrepreneurial fire. It's that I'm not afraid to fail mentality with the process driven proof points. That's where I try to bring everything together. Uh, we focus on a few core areas. Capital raise, readiness, go to market, product, market fit and elements of BCE development, which is business, corporate and ecosystem. Ecosystem meaning partnerships, uh, both with like uh, and friendly entities as well as uh, resellers if you will. If they can add you as a line item, would it enhance, augment or differentiate what they do to further your benefit?

Speaker A: Uh, okay, where can folks learn about you website? Well there's, there's three things. Consuming wine, consuming music and then consuming information so give us your tags. Instagram websites, love to get it all.

Speaker B: Yeah, yeah. So find me on LinkedIn. It's at the end is slash Mnathan M M as in Michael Nathan. N A T H A N M. And you'll see the background. Um, please feel free to hit connect and I'll be happy to schedule time and we could chat. Uh, the music side. You know, the band is Meritage Music. It's on Instagram. Uh, solo percussion is conga king. C O N G A K I N G. Uh, played with many amazing artists from, um, Jesse Johnson, um, you name it. From the time in Prince era to, uh, my own band. And then, uh, wine. We have Nathan Family Vineyards. Right. So we make incredible Cabernet Franc and Cabernet Sauvignon blends.

Speaker A: Beautiful. Amazing. Well, such a good, such a good connection. Um, I travel up north a lot, and we, I, I, I'd love to try your wine. Let's just, let's. I'd love to try your wine and listen to your music. So we, we got to commit to that.

Speaker B: I'll be happy to host you.

Speaker A: Yeah, that sounds really good. Well, Michael, thank you so much for your time. Thank you for being on the Connection Loop podcast. This podcast is brought to you by Dub, uh, the AI powered sales video platform to help you grow your business. Thank you so much, Michael. Thank you for being the best part about Dubb. Um, appreciate your time and we'll see you on the next one.

Speaker B: It was a pleasure. Thank you.

Speaker A: Thanks.