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[Miles] Hey everyone,

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[Miles] welcome back to Year One.

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[Miles] Good to have you here.

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[Grant] Yeah, this is going to be fun.

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[Grant] We've got a special one today.

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[Miles] We're hanging out with Jorge B.

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[Miles] Macias from Puerto Rico,

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[Miles] first founder from the island to take a company through YC with BrainHi.

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[Grant] Yeah, that alone raises a hundred questions,

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[Grant] like what that experience actually felt like from the inside.

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[Miles] Exactly.

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[Miles] We'll talk about his family's sales roots, how that shaped his instincts,

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[Miles] and why an industrial engineering brain ends up obsessed with selling.

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[Grant] And then we get into the messy part.

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[Grant] Those first sales,

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[Grant] zero to the first real dollars,

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[Grant] figuring out a process instead of just hustle harder,

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[Grant] all the emotional stuff founders never write in their updates.

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[Miles] Plus,

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[Miles] how you even begin to go from zero to three million in MRR without losing your mind or your team.

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[Grant] I mean, that deal curve teaches a lot of lessons you don't forget.

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[Grant] We'll pull out the ones you can actually use.

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[Miles] So settle in. We'll start with some quick housekeeping and then get Jorge talking about how he grew up around sales.

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[Grant] Right.

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[Grant] First up,

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[Grant] a little greeting,

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[Grant] a little context, and then straight into his family's sales background and that.

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[Grant] that pivot in the selling.

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[Miles] All right,

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[Miles] let's roll into the opening segment.

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[Miles] Hi, Jorge. It's great to have you here.

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[Miles] I've been really looking forward to this.

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[Miles] How are you doing today?

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[Speaker 3] I am doing good. I am doing good.

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[Speaker 3] Excited to get a chance to speak with you and be on the pod.

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[Speaker 3] Thanks for the opportunity.

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[Grant] That's wonderful.

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[Grant] I'm glad you're here too.

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[Miles] So let me start with something I've always found fascinating about your story.

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[Miles] You studied industrial engineering specifically to get away from the family sales business,

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[Miles] and then sales found you anyway.

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[Miles] What was the moment you actually stopped running from it?

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[Speaker 3] It's a funny story and I'm glad you ask.

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[Speaker 3] My dad and my grandpa were both salespeople and yeah,

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[Speaker 3] the main reason I studied industrial engineering.

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[Speaker 3] was to get away from that but then when I was in college I got very interested in the world of entrepreneurship I was sort of obsessed with Y Combinator and

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[Speaker 3] business accelerators entrepreneurship in general and then after i graduated as an industrial engineer and i started working one of my best friends from college

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[Speaker 3] reached out to me was like hey dude we're building AI for medical offices do you want to help us and i initially started helping them as a consultant and

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[Speaker 3] Then one day they reached out to me and told me like, hey, you understand the product way better than everyone else. You have a good way to connect the value prop of our tool to the business sense or things that businesses care about.

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[Speaker 3] And that makes great for selling. Can you help us grow and expand our business?

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[Speaker 3] That's sort of like how I started. I think industrial engineering actually helped me become a very good salesperson.

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[Speaker 3] And I always approached it as a process engineering mindset instead of just selling.

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[Miles] That's really insightful.

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[Miles] The fact that your industrial engineering background actually became your superpower in sales rather than a detour.

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[Miles] So when you started helping them grow that medical AI business,

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[Miles] what were the first real sales challenges you ran into and how did that engineering mindset help you solve them differently than a traditional salesperson might have?

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[Speaker 3] I think the most valuable thing that I learned.

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[Speaker 3] learned from industrial engineering that transition into sales was that it's a numbers game and that

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[Speaker 3] It is a process. You're going to get an amount of leads that you're going to reach out.

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[Speaker 3] From there, you're going to get another percentage of them are going to respond or going to entertain a conversation with you and a percentage of them are going to entertain a meeting and then a percentage of them are going to end up closing. And those are like the types of process engineering workflows that I was.

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[Speaker 3] Thinking and studying when I was studying industrial engineering,

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[Speaker 3] I just applied it for sales.

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[Speaker 3] I think the biggest challenge was more like the emotional part of things. I think

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[Speaker 3] Like engineering is built in a way that data makes the decision and you sort of detach yourself from the outcomes,

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[Speaker 3] but it sounds that is very very hard because it's your ego,

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[Speaker 3] it's your life,

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[Speaker 3] it's your relationships,

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[Speaker 3] there are a lot of things emotional things that go into it.

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[Miles] That's a really honest take,

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[Miles] the data versus ego piece.

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[Miles] So when did you get the chance to actually apply this process-driven approach at scale?

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[Miles] And what made you think BrainHi was the one worth going all in on?

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[Speaker 3] I think initially we were very scrappy with our sales process,

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[Speaker 3] but as we grew the company from...

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[Speaker 3] one seller to two sellers to four sellers,

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[Speaker 3] we started to need

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[Speaker 3] a structure and an operation that would be sustainable for that amount of people.

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[Speaker 3] And that's where a lot of my industrial engineering skills came in.

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[Speaker 3] So I was like the person who created the cold calling scripts that set up like our first CRM, who was called close.io.

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[Speaker 3] I think they're now called just close.

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[Speaker 3] Then we transitioned into HubSpot for marketing and Salesforce for the sales team. So a lot of those migrations were key parts of scaling our business,

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[Speaker 3] but also me being able to use my industrial engineering skills in a way that would be helpful for the startup and the company that we were building and growing.

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[Speaker 3] And the main catalyst for all that growth was that we were closing deals.

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[Speaker 3] And then because we were closing deals and growing the company, we would have the ability to hire to let some more fire into the growth.

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[Speaker 3] And that at itself became a good environment for me to apply what is now being called go-to market engineering. Like we were scraping the yellow pages.

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[Speaker 3] We were looking for information based on their Facebook to make decisions where

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[Miles] whether like the medical offices were worth investing time or not and that would be sort of like the type of thing that go to market engineers now do for living and now it's like a job and a thing.

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[Grant] So you're building this really structured sales machine from the ground up. Take us back to when BrainHi got into Y Combinator as the first Puerto Rican startup ever.

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[Grant] What was that moment like when you found out?

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[Miles] We were all together.

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[Miles] It was very impressive.

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[Miles] I remember starting jumping up and down and I remember thinking that we were really well positioned to be.

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[Miles] The first big startup of our country.

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[Miles] I was really proud of the team for all the work that we were putting in and how that was being noticed by the biggest and best accelerator business accelerator in the world.

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[Miles] And I really,

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[Miles] really thought that we were going to be the first publicly traded company in the big exit from Puerto Rico.

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[Grant] So you had that moment of real optimism and pride getting into YC,

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[Grant] but going from zero to three million in ARR is one thing. Doing it from Puerto Rico outside the traditional startup hubs adds a whole other layer.

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[Grant] What were the biggest sales obstacles you had to overcome that almost stopped you?

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[Miles] I think being able to gather the data.

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[Miles] And gather phone number of businesses,

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[Miles] gather information of who are the decision makers inside an office and managing that multi-threading problem that each business had was,

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[Miles] I think, the biggest pain point.

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[Miles] We would, there was this mental shift.

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[Miles] from getting over the gatekeeper to winning them over and I think there was like a communication good communication that we did around how we need these people to for us to be successful instead of talking about them as a

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[Miles] obstacle or a gatekeeper, someone that was holding off from our goals.

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[Miles] And I think when we made that shift on the way that we communicated with them and the way that we approached selling into them, that became really,

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[Miles] really powerful.

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[Grant] That shift from viewing gatekeepers as obstacles to seeing them as partners is a classic yet often overlooked breakthrough.

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[Grant] Since you've now built an entire consultancy around this GTM engineering approach for other startups,

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[Grant] what is the one mistake founders make that they almost never realize they're making themselves?

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[Miles] Great question.

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[Miles] There are...

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[Miles] It depends on the stage and depends on where they're at.

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[Miles] The most common problem that I see is they approach B2B selling the same way they approach or understand consumer selling.

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[Miles] I think it comes very natural to founders because they...

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[Miles] That's the only way they have been sold to their whole life. And if they don't have the experience,

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[Miles] it's hard for them to know any difference.

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[Miles] Another big mistake that I know they do is that they...

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[Miles] They think they are going to convince their prospects by talking more and by convincing more and the real secret to selling is asking the right questions and let them sell themselves on why they need your solution or your tool.

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[Miles] and asking the right questions to really qualify if they really have a problem worth solving.

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[Grant] That's such a powerful insight.

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[Grant] Let the prospects sell themselves by asking the right questions.

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[Grant] Before we wrap up, if you could go back and sit down with yourself the week after BrainHi Demo Day,

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[Grant] knowing everything you know now.

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[Grant] What is the one thing you would tell that version of Jorge that he absolutely would not have wanted to hear?

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[Miles] That the boring part of the work that I was doing and the industrial engineer in me that was setting up all the systems for that GTM motion to run as flawlessly as it could was going to become my career and not selling in itself.

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[Miles] I, when I think back to the BrainHi times,

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[Miles] I thought I was going to be a seller forever and I was going to have the same steps and go through the same things that my grandpa and my dad went through as sellers.

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[Miles] And the reality or what I see now is that

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[Miles] I am still an industrial engineer.

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[Miles] I am just applying it to sales and marketing and go-to-market engineering.

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[Grant] Jorge,

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[Grant] this has been such a great conversation,

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[Grant] and I really appreciate you sharing your story so openly from running away from sales to building an entire career around making it work better for everyone else.

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[Grant] Thank you so much for coming on.

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[Miles] No, thank you for inviting me to the pod.

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[Miles] This was super interesting and great conversation.

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[Miles] If someone ever wants to connect with me,

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[Miles] have any questions.

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[Miles] or want to explore a little bit more about my background you can always find me on LinkedIn dash Jorge

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[Miles] dash B dash Messias on LinkedIn or Jorge B Messias with the Puerto Rican flag emoji that's the one that i'm always going to have in my name so make sure to look me up on LinkedIn i try to post every week every day of every work week so um you're i have a lot of content in there or if you have any questions want to um approach me to collaborate or work on something together feel free

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[Miles] feel free to send me a DM.

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[Miles] I'm over there.

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[Grant] That's perfect,

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[Grant] Jorge.

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[Grant] Thanks for making it so easy for people to find you.

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[Grant] This has been a really genuine conversation, and I think listeners are going to get a lot out of hearing how you've built this path from industrial engineering to becoming a GTM expert,

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[Grant] and how that foundation actually became your superpower.

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[Grant] Thanks again for taking the time.

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[Grant] That was such a ride.

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[Grant] I'm still stuck on Jorge describing getting that YC call in Puerto Rico,

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[Grant] like literally walking around old San Juan realizing he was the f***.

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[Grant] It was the first founder from the island to ever get in.

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[Speaker 3] Yeah,

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[Speaker 3] and the way he framed it, pride first,

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[Speaker 3] then pressure.

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[Speaker 3] It wasn't just, cool,

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[Speaker 3] I'm in NYC.

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[Speaker 3] It was, now I'm carrying this expectation for every founder back home.

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[Speaker 3] That's a different kind of weight.

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[Grant] And then you fast forward to Demo Day.

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[Grant] I loved his hindsight there.

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[Grant] He basically said,

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[Grant] I thought the job was to give a great show,

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[Grant] but the real job was to give great clarity.

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[Grant] Who it's for,

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[Grant] what the offer is.

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[Grant] is how it grows.

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[Grant] Super simple, but in the moment,

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[Grant] you're just trying to sound impressive.

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[Speaker 3] That connects right to his breakdown of founder sales mistakes.

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[Speaker 3] The big one,

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[Speaker 3] treating sales like improv.

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[Speaker 3] You wing the pitch,

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[Speaker 3] the pricing,

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[Speaker 3] the follow-up, and then you can't scale it.

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[Speaker 3] His phrase,

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[Speaker 3] GTM engineering is perfect.

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[Speaker 3] It's not charisma,

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[Speaker 3] it's a system.

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[Grant] And that system came out of necessity,

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[Grant] right?

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[Grant] Selling from Puerto Rico, no network,

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[Grant] no warm intros.

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[Grant] He had to build a repeatable process because he couldn't rely on bumping into a buyer in SoMa.

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[Grant] Every email,

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[Grant] every call became data to refine.

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[Speaker 3] That's what I loved; he turned constraints into an advantage.

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[Speaker 3] While other founders were still eagle selling,

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[Speaker 3] custom pitch for every conversation,

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[Speaker 3] he's over there instrumenting the whole thing like a funnel.

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[Speaker 3] Inputs, outputs,

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[Speaker 3] conversion,

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[Speaker 3] iteration.

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[Grant] It's a really actionable mental shift:

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[Grant] stop asking "Am I good at sales?" and start asking

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[Grant] Is my sales process good?

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[Grant] Huge difference.

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[Speaker 3] And his demo day advice to his younger self fits right in.

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[Speaker 3] Tighten the narrative,

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[Speaker 3] narrow the target,

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[Speaker 3] and be explicit about the path from $0 to $3M MRR.

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[Speaker 3] That's not just for investors,

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[Speaker 3] that's for your own roadmap.

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[Grant] Yeah,

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[Grant] if you're listening in your early stage,

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[Grant] this is the episode to replay with a notebook.

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[Speaker 3] Alright,

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[Speaker 3] let's wrap this one.

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[Speaker 3] Miles,

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[Speaker 3] take us to the outro.

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[Grant] All right, we'll leave it there.

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[Grant] I love how our guest took that family sales background and like rewired it with an industrial engineering brain.

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[Speaker 3] Yeah, that was so good.

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[Speaker 3] The whole treat your sales like a system, not a personality thing.

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[Speaker 3] That's going to stick with me.

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[Grant] Exactly.

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[Grant] If there's one takeaway,

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[Grant] it's this.

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[Grant] Your first year job is to turn messy founder hustle into a repeatable process other people can run.

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[Speaker 3] And do it without burning yourself out or hiding behind.

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[Speaker 3] I'm not a salesperson.

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[Speaker 3] We heard what happens when you push through that.

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[Grant] If this helped you see that first-year grind a little differently,

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[Grant] subscribe,

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[Grant] share it with another founder,

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[Grant] and drop a quick review.

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[Grant] Those really do help.

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[Speaker 3] And hey,

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[Speaker 3] if you know a YC founder in their first year who'd tell a good war story,

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[Speaker 3] email us at yearone at heymeado.com.

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[Grant] Thanks for hanging out with us.

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[Speaker 3] We'll see you next time on Year One.