The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Startups & Founders/Founder's Story
Founder's Story artwork

I Was Worth $5 Million at 23. Eight Months Later I Was Negative $1 Million | Ep. 416 with Leo Pareja CEO of eXp Realty

Founder's Story · 2026-07-06 · 41 min

0:00--:--

Key moments - from our scoring

Substance score

68 / 100

Five dimensions, 20 points each

Insight Density14 / 20
Originality11 / 20
Guest Caliber18 / 20
Specificity & Evidence12 / 20
Conversational Craft13 / 20

Leo Pareja recounts a transformative journey from financial prodigy to cautionary tale to CEO of a $5 billion publicly traded brokerage. The 2008 crash devastated him at 23 - shifting from $5 million net worth to negative $1 million in eight months - which unexpectedly became his greatest teacher. He obsessively climbed to become the top agent at Keller Williams and number one globally, only to discover that external achievement felt empty without meaning. The episode explores his evolution through mentorship (particularly a pivotal conversation at 29 with an investor who told him his child-prodigy identity would expire), the pain of selling businesses and losing accompanying status, and his philosophy that everything in business - lead generation, CAC, LTV, churn - operates as pure mathematics. He discusses how he now applies systems thinking across eXp Realty, the death of over-engineered enterprise SaaS, the promise and hype cycle of AI, and his deliberate strategy of making family obligations (children's spring break, school events) non-negotiable calendar items even as CEO of a public company. The conversation covers total addressable market, defensibility against competition, geographic constraints in service businesses, and why founders must develop identity beyond their company.

Key takeaways

  • →A catastrophic financial loss in your 20s - losing $6M in eight months - can become your greatest teacher by forcing you to separate identity from achievement and recalibrate priorities around family and relationships.
  • →Everything in business is a math problem: total addressable market, customer acquisition cost (CAC), lifetime value (LTV), retention, and churn determine success more than hustle or natural talent, which Pareja realized only after the 2008 crash destroyed his illusion of special gift.
  • →Your identity as a founder or CEO will expire or be stripped away upon exit (sale, acquisition, or transition), so deliberately build a multidimensional self as father, husband, community member, and advocate to avoid traumatic identity collapse.
  • →Young entrepreneurs should compress time through osmosis - working directly for or with founders they admire - to absorb frameworks and tactics that cannot be taught in seminars or books, then apply those systems at scale.
  • →As a public company CEO, explicitly model that family obligations (children's events, spouse needs) override quarterly offsites and non-critical meetings, signaling that organizational culture should prioritize long-term human flourishing over short-term productivity theater.

Guests

Leo Pareja

Topics in this episode

Enterprise SaaSCustomer Acquisition Cost (CAC)Lifetime Value (LTV)Total addressable market (TAM)Big Brothers Big Sisters2008 financial crisisKeller WilliamseXp RealtyAI tools (Codex, Lovable, GitHub)Osmosis as learning method

Questions this episode answers

What happened to Leo Pareja financially during the 2008 crash and how old was he?

At age 23, Pareja owned 14 rental properties and was told by his accountant he was worth $5 million, but within eight months that net worth became negative $1 million, forcing him to negotiate with banks to take properties back and call his BMW to be repossessed.

What did Leo's mentor tell him at age 29 or 30 that changed his perspective on career?

His mentor sat him down and said: 'You're no longer this child prodigy phenom that you've crafted an identity around. You're now just an average successful guy in real estate. So you better get pretty good at something else and create a different persona.'

How does Leo Pareja approach family time as CEO of a public company?

He reverse-engineers his calendar by putting his children's spring break and school events in first, and has created a culture where executives understand that canceling meetings to attend family obligations is a priority - he even told an executive considering skipping a child's college move-in that he would fire her for that judgment error.

What business metrics does Leo now focus on instead of just sales volume?

He treats business as a math problem, focusing on total addressable market (TAM), customer acquisition cost (CAC), lifetime value (LTV), retention, churn, lead funnel conversion, and defensibility against competitors - realizing he succeeded through the 2000s real estate bubble, not through operational skill.

What is Leo's perspective on AI and enterprise SaaS?

He believes AI is simultaneously overhyped in the short term and underhyped in the long term, and predicts the death of most enterprise SaaS because it is over-engineered for one customer among many; he expects companies with decent scale will build their own custom workflows using tools like Codex and Lovable instead.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

14 / 20

The episode contains genuine business insights - particularly around identity separation from career, the shift from intuition to systems thinking, and competitive dynamics in tech - but is heavily diluted by personal philosophy, parenting anecdotes, and three sponsored segments that add no substance. The core insights are solid but sparse relative to filler.

Everything's a math problem...there's a formula to everything
I thought I was really good at real estate...I was flying by the seat of my pants. And then the next chapters became about total addressable market, CAC, LTV, leverage, retention, churn, like actual systems and processes

Originality

11 / 20

Leo reframes identity separation from career as a key life lesson, which is somewhat fresh, but most other content - founder humility, the value of osmosis learning, AI overhype cycles, ecosystem lock-in - are well-worn frameworks in tech/business discourse. The 2008 financial crisis bounce-back narrative is also common in founder stories.

No matter what chapter I'm in, I've had some really cool titles...but from that one experience, I also remember that this is just a role I'm playing
I think most things are overhyped in the short term and underhyped in the long term

Guest Caliber

18 / 20

Leo Pareja is legitimately high-caliber: first Hispanic CEO of a major public brokerage (eXp Realty), former number-one agent globally, founder of multiple companies, raised tens of millions in VC, and operates at genuine scale. His credentials are exceptional and directly relevant to B2B operators seeking to understand scale, leadership, and strategy.

First Hispanic CEO of a major publicly traded brokerage
I'm the CEO of exp. Globally...a $5 billion enterprise business

Specificity & Evidence

12 / 20

Leo provides some concrete examples (14 rental properties, $5M to -$1M loss timeline, being number-one at Keller Williams, eXp valuation at $5B) but relies heavily on abstraction for business lessons. Discussions of CAC/LTV, TAM, and competitive dynamics lack specific numbers, company examples (other than passing mentions), or real case studies from his ventures. The episode stays mostly at the 30,000-foot level.

I owned 14 rental properties. My accountant had just told me I was worth $5 million. And within eight months, that number went to negative a million dollars
By 28, you were considered the number one agent at Keller Williams...number one agent in the world

Conversational Craft

13 / 20

The host asks reasonable setup questions and does follow up on key moments (the crash, the turning point at 29), but rarely pushes back, challenges, or digs deeper into contradictions. When Leo makes bold claims (e.g., 'OpenAI probably won't make it,' 'death of most enterprise SaaS'), the host largely accepts them. The conversation feels friendly but lacks the rigor of a substantive business interview.

Leo, I have to understand the feeling when you heard this
What changed within you though that you said going forward I'm going to do this differently?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A80%
  • Speaker B20%

Most-used words

real26number17life17world14back13estate13first13didn13founder13wasn12kids12moment11remember10dollars9experience9create9

Episode notes

Daniel and Leo Pareja , CEO of eXp Realty , unpack what happens when someone finally reaches the goal they have obsessed over for years - and discovers it does not feel the way they expected. Leo shares how becoming the number one Keller Williams agent at twenty-eight left him depressed and confused because nothing inside him changed. From there, the conversation moves through his financial collapse during the 2008 crisis, the mentors who reshaped his identity, and the systems that helped him rebuild. Leo also explains why young people should compress time through hard work, why founders must separate themselves from their titles, and how AI may fundamentally reshape enterprise software and entrepreneurship. Key Discussion Points Leo shares that becoming the number one agent at Keller Williams was one of the emptiest and most meaningless moments of his life, despite spending nearly eight years obsessing over that goal. He explains how conversations with millionaires and billionaires taught him one consistent lesson: do not sacrifice the years when your children are young because those moments cannot be recovered.

Full transcript

41 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I owned 14 rental properties. My accountant had just told me I was worth $5 million. And within eight months, that number went to negative $1 million.

Speaker B: This is Leo. He bounced back to become the number one real estate agent in the world and the first Hispanic CEO of a major publicly traded brokerage. This is how he rebuilt.

Speaker A: So I went from what I thought was success, and that was like a half a million dollars a year, 20, $30 million in production, to jumping up, to becoming number world. There's a formula to everything. Everything's a math problem. The big pivot was I would advise people to actually,

Speaker B: Leo, I have to understand the feeling when you heard this. By 28, you were considered the number one agent at Keller Williams, which was the largest brokerage. You could say that you are the number one agent in the world.

Speaker A: So the interesting part about that question is it was actually the most empty and meaningless feeling of my entire life. And if I were to take you back, when I got into real estate at 19 and I learned that that was a thing I could achieve, I had two singular obsessions when I was about 20, 21, which is one, I wanted to be on N30 under 30 list, and then I wanted to be number one at Keller Williams. And it became an obsession, like, for eight years in a row, it's all I cared about. I tracked, you know, and it was. It was. It was a fun process because I went from. I wanted to be number 1 in my office, then I wanted to be number 1 in my region, then I wanted to be number one in the east coast. And then, like, slowly climb and then, you know, I made it to, like, number four a couple times and number three. But the second I got it, I woke up the next day, and it was actually very sad and depressing because I didn't feel different. It wasn't my most profitable year. Nothing changed. I didn't, uh, get this unlock of wisdom or transformational. Aha. And I didn't actually know what I wanted to do after that because it was. It became such a core driving version of who I wanted to be. Then once I got it, it actually almost left me confused. And it. And. And it's been a really interesting kind of anchor for me because it just reminds me that, you know, no matter what role, I. I talk about seasons of life. I'm super happily married with two amazing little ones right now. And so the season I'm in, I just don't want to screw that up for them because in that journey, Daniel, I actually got to be in Front of a hundred millionaires and billionaires. And I got into the habit of asking each one of them, like, what would you do different? Like, what's the one thing you'll tell me? And, um, they all. And mostly, you know, in the early 2000s, there were baby boomers. They all had the exact same reaction, which is, don't screw up the time with your little kids. Um, and so that's become a very core thought process of, like, no matter what chapter I'm in, I've had some really cool titles, like, number one in the world, or founder or CEO of a $5 billion enterprise business. I get to be on the news. I get to be on big stages. But from that one experience, I also remember that this is just a role I'm playing. And, like, when I'm taking my last breath and hopefully I'm an old man, I'm going to be surrounded by people who care about me because I showed up when it was important and it wasn't like, oh, I'm sacrificing for them. M. Like, no, that's bullshit. Like, actually show up and don't forget the important parts.

Speaker B: Wow. The people that we've talked to, like you said, the most successful people almost always say their biggest regret is they missed out, uh, on all of their family stuff, their kids, recitals, whatever it was. They were just not there for their children or it even ended their marriage. It had a turn on their personal life. At what moment for you, though, where you said, I need to balance these things? Because I imagine, uh, you could not have balance. You could just focus only on work.

Speaker A: Yeah. So for. For again, the gift I've gotten that I just. I just think I'm the luckiest kid in the world. And it's. I give it to. To the universe or God, whatever you believe that that makes you feel good as a human being is I've just had really good good luck as a young person. And the luck I had was getting the kicked out of me in the financial crisis. So I was 23. I owned 14 rental properties. My accountant had just told me I was worth $5 million. And within eight months, that number went to negative a million dollars. And I was, you know, in the fetal position, crying, negotiating with banks to take some of the properties back. Called BMW and said, you need to come get your car. Um, and I realized in that moment, because as I was driving towards my goals, I always had this thought process of, when I get there, I will do X. Whether that was like giving back, spending more time with my parents, my family, um, and I lost it all in literally seven, eight months in dramatic, chaotic fashion. Which again was not unique. If you haven't seen the movie, I recommend the Big Short. And uh, I remember when we watched it with my wife, I think I was like, she looked over at one point and I had my shoes on the couch and I was like in a fetal position. She's like, yo, you got real PTSD just watching this movie. But that early experience taught me that it's all a moment in time. It can all vanish super quick and from friendships and relationships, um, to like literally the roof over your head actually in that moment. My wife, uh, who was my girlfriend back then, we both decided we were going to be mentors with big brothers, big sisters. Because I always thought when I have more money, I'm going to start a foundation and I'm going to give back. And then it all disappeared. And I realized that like in the

Speaker B: hotel gym just now traveling, I was on the treadmill watching my favorite episodes while I get a workout in. And the only reason I could do that is because of Proton vpn. Without it, I'd be staring at this. Content isn't available in your region screen, which I hate and I know you hate that too. All I had to do is change my virtual location. Everything works the way it should. ProtonVPN is a secure VPN service built for people who actually care about the digital Privacy. Unlike most VPNs, Proton is backed by strong European privacy laws, a strict no logs policy that's independently verified and it's open source so anyone can inspect and how it works. It runs seamlessly with high speed connections, integrated ad blockers and servers in over 145 countries. Whether you want to stream from anywhere, get around blocked sites or stay private on um, public wi fi, ProtonVPN has you covered. Right now ProtonVPN is offering our listeners 70% off a two year plan. When you go to ProtonVPN.com founder P R O-T O N V P N.com SL founder for 70% off a two year plan. That's ProtonVPN.com founder it's, it's doing it in the moment.

Speaker A: And so like when it comes to giving, I've always told people like just give to one person and that could be way more impactful than writing a thousand dollar check or $100,000 check. Um, my wife and I did start a foundation once we had money. But whether it's spending time with loved ones or A cause that you care about. Like, I now reverse engineer everything. So when I plan the 2027 calendar for exp. Co. For exp. Globally, my kids calendar goes in first, my kids spring break. All the. All the things that, um, we can plan ahead of time. And again, like, every. Every school drops some nonsense on you two weeks out. But I've also created a culture that my people understand that that's actually my priority, where if. If I'm like, hey, I'm canceling today, and I'm no longer attending a single meeting because it's my kids. This. They understand that that's my priority. And I think it's shown a version of leadership that is different than what you're normally expecting at a public company. Very real story. I had a, uh, an off site with my executives, and there was a, um, an executive who looked really upset. And I was like, what's wrong? And she said, I'm missing my kids, um, move into college. And I was like, why are you here? Like, this is insane. She goes, well, I know that these only happen once a quarter, and I didn't want to miss it. I was like, if I catch you doing something like this, I will fire you like this. This was a terrible judgment call on your part. Like, you should have just told me, because you can't, um, undo that, right? Like, you can't forget that. And again, none of this is wisdom, right? Like, I miss some of my best friends weddings and bachelor parties. And Daniel, for the life of me, I can't remember it was so important that I didn't show up. And so the gift I. I feel I got is I got that really early, and I screwed up. Like, friendships versus, like, my kids.

Speaker B: I remember the crash of 2008. Unfortunately, I lost my job and I had to live in a tool shed. So although I didn't lose homes, I definitely lost my dignity and my motivation. It was just like you. It gives me PTSD when I think about how horrible that experience was. When you think about agents and executives and people that you come across who have that young, excited, motivated energy, like their 1920s, early 30s, maybe they don't have a family yet. Uh, they're just super motivated to get to that number one mark. How do you talk to them without stifling that motivation?

Speaker A: Well, no, I, uh. So this is where I sound maybe a little schizophrenic, and I talk about seasons, and I said, actually, I think the world actually is too soft on young people. I think you should work 12 hours a day. Seven days a week. Because youth is wasted on the young. Right? Like energy is a superpower.

Speaker B: Um, when you're producing a show like founder story, the amount of content we push out is massive. YouTube audio, social clips, TV. Every piece needs music, B roll, sound effects. And I used to waste hours along with my editors hunting for assets and worrying about licensing. Then we found Storyblocks. Storyblocks is 100 human made stock library built for creators. Every asset is made by professional filmmaker or artist, never AI generated, all pre licensed and ready to use and monetize content. Unlimited downloads under one subscription means I can experiment freely, try different tracks, swap B roll, no per download, stress their members, save an average of three and a half hours per week. And every download directly supports a real working artist. Head to storyblocks.com founders to access human made stock media library. That's essential to, to my workflow. For a limited time, they're offering 15% off any annual plan. And that discount is only available through my link. Again, that's storyblocks.com founders for 15% off annual plans.

Speaker A: There's a really interesting concept of, you know, when you're 19, all you have is energy. And so I can create more output now in two hours than I could at, at 22 in 12 hours. That's kind of the gift of life, of experience and wisdom. But when you don't have any experience and wisdom, all you have is time. So go do right, go put in reps. And I tell young people to compress time as much as possible. So whether that's in real estate, that means join a team in entrepreneurship, go join a founder that uh, you want to be like when you grow up. Because I think the best teacher in the world is osmosis. Just, you know, to quote Hamilton, just get in the room where it happens and just, you know, I was a sponge and I, I always seeked out mentors and when the meeting was over I'd call them and kind of get the replay or walk with him, be like, hey, let's go to luncheon. Why did you ask that then? Why did you pause? How did you know they were going to say that? And you, you realize that there's a framework, a tactic, a ah, structure to a conversation. Um, and that only comes from experience. And you can't read it, you can't buy it, you can't attend a seminar. You have to be in the, in the opportunity, in the transaction, have it blow up in your face. And that's, I encourage young people to create as many experiences as possible.

Speaker B: I am the biggest proponent of osmosis. I could have never been successful in business if I didn't work for somebody else unless I had raised millions and millions of dollars, which I don't think was ever going to happen. So I am totally with you because some people are like, I never want to get a job. I just want to go into business and I'm with you. Something was told to you at 29 that changed your perspective. What was that?

Speaker A: So I had, I had a mentor, uh, who was transformational in my life, um, and he took me under his wing or paid attention to me because I was like 23 and doing pretty well. And actually where we developed a, a real respect and friendship was with my hustle. Like I remember it was D after the crash. He was a very well healed investor during the financial crisis. And we went and bought a bunch of real estate after the crash. And I did the work and he kept most of the upside, which is how it works when you're young. And uh, it was a great deal for him and we created lots of value during that time period. Um, and he was like, I called him uncle, uh, because he walked in to a lot of banks and co signed me and said, this is my boy. But I remember when I was turning 30, he sat me down at lunch and he goes, just a heads up, you're no longer this child prodigy phenom that you've kind of crafted an identity around. You're now just an average successful guy in real estate. So you better get pretty good at something else and create a different Persona. And I think it where was interesting was around identity. Right? And that's where, you know, when people just make their career, their identity, you could have some really traumatic falls, um, because that's not who you are at the end of the day. Like you were multifaceted. I'm, I'm a father, I'm a son, I'm a husband, um, I'm an advocate, I'm part of multiple communities. And um, I just, I see it often where entrepreneurs become like super one dimensional and um, even if it goes perfect, this is another really interesting, uh, heads up. I got from a good friend, I was about to sell my first company and he gave me a hug and he goes, hey, this is going to be the most traumatic experience of your life. I said, how do you. What do you mean? It's like, this is what I've been driving towards. He goes, it's going to suck no matter what. M and A is brutal. Like their Job is to hurt you and take from you and the other side and the bankers. And so no matter if the outcome is what you expected or more than you expected, um, when you actually sell a business and I've sold three, you actually give away a big part of your identity. And, and on the very first one you'll learn basic, like, have an email address that has nothing to do with the business. Right? Like I, I have a personal email@leopreha.com which I. But like when you sell your first company, they're like, okay, hand over your email. Like, hey, that's how I log into like everything. Like, what do you mean? It's my bank. Like you actually hand over all of it. And especially if you're a big deal in your industry because you've crushed it, you lose that because all of a sudden people that you thought, um, were friends, they were professional friends, but you were, you no longer have status in that, in that world. Uh, because you're no longer the founder and CEO. You're just like the, the guy who took over your company or the gal who now runs your company. It's her company now. Right? So there's some, there's been some very interesting life experiences of who am I, what am I? And outside of being a founder after

Speaker B: the crash, going back to that, and then you said you now had this new connection and relationship with someone who changed your life. What changed within you though that you said going forward I'm going to do this differently?

Speaker A: Yeah, well, I mean that was one facet of it, right? That was just for investing versus one. Um, was being a student of history and just realizing that I was, I thought I was really good at real estate. I thought I was special. What I didn't realize I just had a real estate license during the greatest real estate bubble in the history of the world with slightly more hustle than the average person. And then I was like, oh, I, uh, like I'm actually not that good at lead generation, conversion, funnel, follow up process. Like I was flying by the seat of my pants. And then uh, the next chapters, um, became about total addressable market, cac, ltv, you know, leverage, retention, churn, like actual systems and processes, um, realizing that there's a formula to everything. I often uh, talk about that everything's a math problem. And I think building a business to even being at your ideal weight. It's, it's like caloric deficit. You don't want to eat less, work out more. Like you need to be in a caloric deficit to Lose weight. If you want to have a business, you need to create more revenue than expenses. And that's, that's normally a factor of lead funnel to lead conversion to client retention. And so the big pivot was I'm good at something and it's kind of natural, or I'm, um, like, gifted at it versus, like, no, um, it's a math problem. How big is the total addressable market? How do I capture a unfair share of the marketplace at a unit acquisition cost? That makes sense. And how do I scale it for the long term, make it defensible so not someone can't go, oh, Daniel built a cool mousetrap. Let me go take his cheese. Now.

Speaker B: I hope no one takes my cheese. I'm gonna do some math because I need to protect my cheese. And you're right. And also, there's so much competition nowadays.

Speaker A: Well, I spent 10 years of my life in tech. And, um, like, a service business is easy, right? In my opinion, because service businesses normally are completely, um, geographically tied. So take your favorite. Fill in the blank, Daniel. Like, there's, there's math for everything. Like, if it's a deli or a coffee shop, people won't drive more than a mile, right? Like maybe a gym for your kids versus you. Like, it's, it's proximity based to your life. Um, real estate, like, you can only serve up to maybe 30, 45 minutes away. Like, you can't be driving two hours one way for an appointment. Tech, you could build the coolest thing in the world. And if it scales super fast and it's great economics, Google goes, thank you. Like, I'll just build it, right? I have a better funnel at the top. And Amazon's famous for it, where, like, they have a product and they'll put under Amazon households or basics, you know what I mean? So just, um, understand. And, and by the way, like, that's the goal of capitalism, right? When, like, arbitrage, in my opinion, is an efficiency in market, period. And as a segment gets more sophisticated or gets larger or more established, the margin naturally gets compressed, right? That's, that's what happens. And so that's also part of the game of, of an entrepreneur, like, just be okay with that. Sometimes the movie ends, um, through consolidation or through acquisition or through just like that opportunity isn't there. And we're probably living through a phenomenal, uh, moment in the death of most sass as we know it, right? I think, um, I think AI is grossly overhyped and underhyped all at the same Time, which is like a weird schizophrenic sentence, right? I and, and I think most things are overhyped in the short term and underhyped in the long term. Right?

Speaker B: Like, have you been sitting on a business idea? Let me tell you something. I've been selling on Shopify since 2012. I started with a men's grooming line, built out a full skincare brand all on the same platform. And the thing that blew me away from day one was that everything I needed to actually start selling was already there. I didn't need to piece together five different tools or hire a developer. Shopify had it already. The moment that first customer is ready to pay, the checkout just worked. No friction, no drop off. And when customers come back, their details are already saved. One tap and they're done. That was huge for me early on because every completed sale built my confidence that this thing was real. And because Shopify handled the setup and the checkout, I wasn't stuck troubleshooting my own website. I could actually focus on building the brand, creating new products, running campaigns that shift from figuring out the tech to actually growing the business. That's when everything changed for me with Shopify. Nothing stands in between your idea and a real business. So go make it one. Start your free trial at shopify.com founders story. Start your free trial at ah, shopify.com founders story.

Speaker A: We're on version 17 and V1 was an iPod that allowed me to make some phone calls. This thing today, like I just got into the country using it. It's got my credit cards, it starts my Tesla right. Like it's so far removed in version 17 than it was in v1. And I think we're seeing already some of that over hypeness in AI. And I think it's fascinating because if you look historically at almost every transformation technology and I would put the steam engine and trains and the Internet in 2000, which I viscerally lived through that cheese moving. That's how I ended up in real estate. It created a massive over investment which followed by a massive crash. But the infrastructure that's left over afterwards, whether it was laying railroads across the late 1800s, I think we had like 118 railroads and like 30 years later we had four. Right. But the, the, the railroads laid create the foundation for like west western expansion in like the economy that we have today. You know, pets.com famously crashed and billions of dollars of revenue evaporated in the early 2000s. But it was that fiber optic cable that we laid across the ocean that gave us high speed Internet, which changed everything, literally everything. So I think that's what's happening and the one really real part of AI that I'm witnessing, experiencing and again this is I was a non technical founder who founded a tech company which is a very small club which is actually really inbred. A lot of insecurity in me because prior to that, whether it was real estate or lending or anything happening to do, you couldn't me like I could just go down to the courthouse and see the permits were pulled. If a contractor told me something, um, I'd walk around with a tennis ball at construction sites and just put it on the ground. I'm like, well if this thing rolls we have a problem and I don't need to be an engineer to figure this out. In tech I couldn't look at the code myself. But now with Codex and Lovable I can get into GitHub and I can do things and I think it's really changed the process flow of I can get a frontline person who understands the workflow to build the wireframe for me and then I give it to engineers to make sure it's SOC2 compliant and it's scalable and it's on the right database schema. But I do think we're going to witness the death of most enterprise SaaS. I think most enterprise SaaS is over engineered because you're one of many customers and it doesn't do exactly what I want it to do. And I think most businesses that have some decent scale are going to be able to build their own workflows and um, that's going to be a massive disruption to the world.

Speaker B: Yeah, I always laugh when you ask them what are you building? And they're building the exact same thing to solve the exact same problem. I don't even know how most of them get funding. I was listening to a recent C suite of a publicly traded company that's involving social media and then I was listening to a debate around that this person typically never uh, creates something new, they never start something new. It got me thinking about there's power in not being the first. And I imagine when you're publicly traded there's even more power many times in not being the first and only doing it once it's already been proven by somebody else.

Speaker A: Yeah, that's a great question. I actually uh, when I talk about AI with agents because they all have the same kind of like anxiety around it. Right. I, I think every human being on the planet has anxiety around it, especially the way it's marketed. And a couple, couple thoughts like the people over hyping it are the ones who are financially incentivized to create massive returns. So always pay attention to the source of the fear, right? Fear mongering is, that's the reptilian brain in our evolution. Like that thing is designed to keep you alive and nothing makes you pay attention more than fear. Like so always remember that two is that I actually say in AI, um, I, I, I think we're in our MySpace era. There's absolutely nothing that says that open a. And again, like when I said this six months ago, Daniel, people were like, oh, I said open AI is probably not going to make it. I think now when I say it, people are like, yeah, that kind of starting to feel pretty, pretty correct. Like if I had to bet right now, Gemini is the winner. They have the most resources and that's kind of what happens in life, right? They have the most cash, the most, uh, top of the funnel, right, for delivery mechanism. They can, they can make it free and then they choke out the competition, right? And so, um, famously I would say Apple is that, you know, they, they normally aren't like uh, the I, the ipod was like, you know, there was other ones out there. The Palm Pilot, you remember that one. Like Nokia, um, owned the BlackBerry, owned the market, right? Like the iPhone was revolutionary, but it wasn't like the first cell phone, right? Nokia and BlackBerry had dominance, but then they made a couple experience tweaks and where I think they've won is the ecosystem. So companies with market power that have ecosystems and then that's where that was the big lesson I learned when I spent time in tech. It was like also understand who can put you out of business overnight, right? Like if you're, even if you found a green space and no one's touched it, let's just say you execute. Who can kind of tiptoe in and move your cheese overnight. And again, a lot of times that's how you get acquired, right? Um, but fam. There's been many famous case studies where they were negotiating with an acquirer and the counter acquirer goes, well, you just push the pass pass. The point of build by and after this I'll just build it, right? So there is a. I will pay X dollars to not have to go through the R and D process. But past a certain point I'll just do it myself.

Speaker B: This all reminds me of who Moved my cheese, which I haven't read in 25 years. I've heard this as a great acquisition strategy to get connected with the company who you'd want to be acquired by and build some sort of relationship with them early on. But it sounds like to me, that could also be at your detriment.

Speaker A: I could tell you five stories on both camps that that played out beautifully and disastrously. Right? There is always the risk. So it's actually a good segue because I often get asked by, like, a founder who reaches out cold and says, hey, I want to show you something. And they get on my calendar and they're like, hey, I need you to sign Indy. I'm like, did you bump your head? Like, you cold reached out to me? You have absolutely no idea what's on my roadmap. So I literally have a policy where I won't sign a single one. Right. Because again, even more as a public company, I don't want to put myself in jeopardy where I create liability, because I have no idea what you're going to show me. And it often happens where someone shows me something, I'm like, oh, buddy, like, I've already built it. Like, I'm turning it on in a week. And I think that actually happens because, like, society creates opportunities, and, like, you're not the only one who sees that opportunity. Um, and so a lot of times I feel like I've been on both sides where I felt like a bigger company copied me, and now that I've been the big companies, like, oh, I didn't comprehend that big companies have, like, 200 engineers and tens of millions of dollars in R and D budgets, and we're seeing the same bottlenecks and pain at scale, so we're also trying to solve that. So there has to be a level of fearlessness that comes with, uh, entrepreneurship. And, you know, um, the little guy always has the advantage of speed, right? It's like, I can just move faster because I'm willing to work 12 hours a day. And, you know, my senior engineers prior not. Versus the two kids in a basement. Like, the. The thing that's kept me motivated and awake at night for 24 years are the two kids in the basement who can move my cheese, because I just didn't see them coming. Um, and. And I was the. The two kids in the basement once, so I. I know the feeling. And, um. But you can't control what you can't control, so I would advise people to actually form that relationship early.

Speaker B: I was just recently at Cannes Lions, and at the event, there was a lot of C Suite mixing with a lot of People who are titled themselves as creators, like these are, you know, social media creators. And uh, what I saw is a lot of the C suite are seeing themselves as a creator. It's like their goal is to build a social media presence themselves which uplifts the company. Also builds a lot of trust and authority back to the company. What are you seeing or uh, what are you hearing out of all the C suite when it comes to publicly traded companies?

Speaker A: No, that's. And I think that's more of a very good take on society. Right. Something I say a lot is marketers ruin everything. And again, it's a feature, not a bug. It's, it's like, it's not a diss at marketers. And uh, I'll walk you through kind of like the emotional feelings of it.

Speaker B: No lie, I've said that many times before, so I'll let you continue. But I can totally relate to what you're going to say, so.

Speaker A: So, you know, I remember fist fighting my brother to pick up the phone because someone was calling on that one phone in the kitchen with the long wire. Right. We were excited when the phone rang and then cold callers ruined that.

Speaker B: Right.

Speaker A: Uh, email came out late 90s open rates were like 70, 80%. You could pretty much sell anything if you could get an email list big enough. Tom Hanks made a movie about it when he got mail, right? How it's like an entire rom com was about the concept of an email. When's the last time you read your email, Daniel? Right. Like it's, we've become numb to it and, and, and you know, radio killed the, uh, TV killed the radio star. Everything's about attention. If, if I were to take the average human right now and this, this is what I would say to any other CEO who's like, I create six pieces of content per day. Uh, no, 12 pieces of content on six platforms. We push out a ton of content. I have two podcasts, one non industry, one industry, one that I do myself and I speak in public about the subject often. But, but I tell agents all the time, like open this thing up, go to screen time and show me where you spend your time on the top three apps. If you are not creating content for your audience in the same medium and depending on the audience, it's Instagram, Facebook, TikTok, chat, GPT is getting up there into the top three or four, right? So that's also a data point that I say to any entrepreneur, right? Figure out who your ICP is and then figure out where their Attention is. And you are the brand, right? You are the personification of the brand because there is no trust in the world right now, right? Like that's our logo. But that doesn't mean much to someone who does. Who like my customer are agents. And so I create content for agents and entrepreneurs all day long. Um, when they are ready to make a buying decision, they've already formed a digital relationship. Right. I often say I'm in a one ah to one and one to many relationship in at scale. I'm in a one to many digital relationship with hundreds of thousands of agents in my industry. My goal would be the 1.4 but I'm not naive and think I, I have that much reach. But it's definitely a couple hundred thousand. Right? Um, then you can have a ah, one to many, one to one personal relationship with folks that also carry influence. So I would, I would advise any public company CEO is like, okay, once you understand your avatar then understand the people that influence them, right? So whether that's collabing with those folks of influence or just making sure that when you think of the product service industry that they've also created a real engagement to you. And I think the most exaggerated examples of that are Mark Zuckerberg and Elon who over the last decade uh, have become the brands themselves. Which by the way that I think there's single point of failure and uh, there's you know the, the founder on trap is also a real, real concept but I think I'm a pretty good example because I'm not the founder of exp. Our founder is very much still around but he's done a really good job of being able to transition the baton if you will. Um, and I think why it worked is because I took a very forward facing approach of uh, brand building.

Speaker B: First Hispanic CEO of a publicly traded major brokerage which means all these millions of people that then look up and say he represents us. If he did it now, I can do it right. I see it, I can then be it. What weight though did that carry?

Speaker A: So that it's a very real part of my identity. I'm Latino, I was born in Latin America, I moved to the states, I was 12. I've been an advocate uh, in Congress. I've, I've spoken to legislators my whole career about it. But I, I think representation in, in just the visual portion of it is so, so real. So I, I grew up um, in an industry predominantly that didn't look like me. There was, there was, there was not a single Leo when I was growing up where there was a, A, ah, mentor who produced at my level, let alone ran a public company. Um, and I can tell you that anytime I'm in a large setting, some little Latino kid comes and tells me how important it is to see me in the seat, because it does make it more real for them. But I was also super aware growing up that I wanted to be number one comma that happened to be Latino. It wasn't the other way around for me. Um, and I think that was the biggest flex for me. It was like, I want to be number one in my market, in my industry. And oh, by the way, yes. Then I'm also that other thing which, which almost goes back full circle in the conversation of like, I'm not one dimensional.

Speaker B: Right.

Speaker A: I'm, um, I'm, I'm not Latino only. It's, it's one of my many versions of myself that I'm quite proud of, and it's very important to me. I, I live in Miami. My mom and dad are down the street. I'm, I'm a very proud Latino. Mom was a boy. And, and, and I fit into this, like, what I believe are the positive cultural stereotypes of my community. But, but it doesn't define me as one dimension.

Speaker B: My wife and I wrote this book called Unlimited Possibilities. Essentially, it's breaking through barriers that you did not think were possible. What was an unlimited possibility moment in your life? I know you've had many, but, uh, what is one that really stands out?

Speaker A: So it would probably be bouncing back from the financial crisis. So I went from what I thought was success, and that was like half a million dollars a year, 20, 30 million dollars in production, to jumping up to becoming number one in the world. But what, what, what really, like, sunk in for me after that experience of first A, that like, I didn't feel different or feel better. Like there was this, uh, this, this disappointment, but also that you're never ready. So I'll take you back to the first one at the hospital. And they're like, all right, keep it alive. I'll see you later. And you're like, how am I gonna do this? So life is like that, right? Like there is absolutely. You've never done this before. And, um, like, I wasn't qualified at 19 to sell anyone real estate because I looked about 13. That's when I grew the facial hair and haven't cut it off since then. I wasn't qualified to buy my first house at like 20. I wasn't qualified to, um, sell the volume of real estate. I wasn't qualified to convince Fannie Mae and Freddie Mac to let me sell their foreclosures when I was 23. I wasn't qualified to raise tens of millions of dollars from some of the most marquee venture capitalists in the world. I wasn't qualified to be a public company CEO by definition, because I wasn't a public company CEO. Right? The moment you realize it's like you're gonna die, like, 100% chance, you might as well have the most fun and take the most, you know, calculated risk that you're comfortable with. Because at the end of the day, it's just going to be a fun journey that hopefully, as an old man, I get to tell my grandkids, sounds

Speaker B: like this is the best way to get over imposter syndrome. Do you even believe in that?

Speaker A: I. I still have it, which I don't think you can be human and not have it. Right? And so also, um, just remember that everybody around you has it. And that's, that's actually a, a very comforting feeling when you're like, everyone's kind of like that insecure little kid of whatever moment in time you were stuck at at, you know, middle school, awkward moment. And like, you built your entire personality around that over overcoming that feeling when you're ever feeling it. And I have an 11 and 9 year old. My, my, my 9 year old is big into jiu jitsu, and he recently competed in a tournament. And the kid that was in the finals had like a thunderbolt shaved into his head and came out onto the mat pounding his chest like a gorilla. And, uh, I got scared. I was like, I don't want to fight that nine year old either, but my son wanted to go home and I sat him down. I'm like, look, he can't kill you, right? Like, actually figure out what's the worst possible scenario. And, like, the worst possible scenario is death. And in most, 99.9% of the things that you'll look at in life, Daniel, that's not an out. That's not one of the possible outcomes. So I'm like, he can't kill you, right? He's like, no. I was like, tap. The fight will be over. Like, just pull guard and let him do his thing and it'll be over. I'm like, and what's the worst thing could happen? He's like, I'll lose. I'm like, okay, you lose every day in the gym. And, um, but I said, you know that feeling you're Having. Yeah. I was like, he's like, he's like, I'm terrified. It's like courage is misunderstood. I like, fearless leader is a very common moniker I hear for leaders. There's no such thing as fear. I haven't, I haven't done scary that where, uh, I was fearless. Right. It's actually doing the thing in spite of the fear. That to me is the definition of courage. And so that's. I. I say to my kids, but I also like, remind it to myself. Like, it doesn't matter how many times I've been on stage in front of 5,000 people. I. Right. Right. When I get the microphone, like, I gotta, I gotta entertain and delight for the next 45 minutes. And it's just me and a microphone.

Speaker B: Did your son win?

Speaker A: No, he lost. But he like, came in second at a huge tournament and was. And the kid who beat him is homeschooled and does it eight hours a day. And I've actually said. I was like, I don't actually care. The only thing I want you to learn from this is how to lose gracefully. Because the entire educational system is broken. Right? Like, we're. We're taught to like, incrementally get better at stupid. That we're never going to do again. Right? Like, like, getting up is the game in entrepreneurship, in life. It's just like, how many Ls can you take and just get back up? And that's actually life.

Speaker B: Leo Pareja, uh, CEO of exp. Man, this is longer than the conversation I just had with Mauricio, by the way. So I'm gonna tell him that we even had maybe a better conversation. Don't tell him. I don't want him to be upset.

Speaker A: I said I'm a. Text him when we're done.

Speaker B: Send him a text. Tell him that I said that, but. Don't tell him I said that. But. No. Thank you so much.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Ep. 198 - How to Make Your SaaS Company More FundableSaaS Backwards · on Customer Acquisition Cost (CAC)94 / 100
  • Why Marketing Attribution Breaks on Subscription ModelsMarketing Analytics with Fexingo · on Customer Acquisition Cost (CAC)92 / 100
  • When to Raise VC - and When It Destroys DisciplineStartuprad.io™ · on Customer Acquisition Cost (CAC)85 / 100
  • Why Revenue Is Up But Profit Isn't Moving: The Unit Economics Blind Spot Most Shopify Brands Have - Misha Druzhinin | Why Revenue Doesn’t Equal Profit, Why Scaling Profit Beats Scaling Revenue, The Hidden Danger Of Discounts (#481)Ecommerce Coffee Break · on Customer Acquisition Cost (CAC)82 / 100
  • Selling a SaaS Business? The Metrics Buyers Care About Most Business Beyond You · on Customer Acquisition Cost (CAC)80 / 100
  • Brian Murphy: Fundraising $25B Across 44 Funds, $73B Merger, Private Equity, Secondaries, BuffettStartup Ignition Podcast · on 2008 financial crisis80 / 100

More from Founder's Story

All episodes →
  • $5B Real Estate Mogul Reveals The Price of Success | Ep. 411 with Mauricio Umansky Founder and CEO of The Agency56 / 100
  • He Made Millions Every Year, Then Went $800K Into Debt: Adam Hagaman on the Trap of Success | Ep. 410 Founder of Content Cash Flow48 / 100
  • The Supplement Industry Is Broken and Ritual Is Rebuilding Trust From Scratch | Ep. 409 with Kat Schneider Founder & CEO of Ritual66 / 100
  • Do You Need To Live In Silicon Valley To Start a Tech Company | Ep. 415 with Moe Seye Founder and CEO of 1099Workers
  • Free Trading Isn't What You Think It Is (Wall Street CEO Explains)
Explore the best B2B Startups & Founders podcasts →
All Founder's Story episodes →