Wealth Independence Podcast

v1.1 - A Journey To True Freedom ft. Saket Jain

• Dustin Bailey & Adam Penn • Season 1 • Episode 1

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Join us for a profound conversation with former Airbnb executive Saket Jain as he shares his journey from the constraints of corporate life to discovering true freedom through alternative investments.

Saket shares how a 2017 layoff served as a wake-up call that transformed his definition of security and independence, leading him to methodically build personal freedom through investing in various asset classes, including real estate and venture capital.

Discover how he balances analytical thinking with practical execution, how he avoids common investment pitfalls, and his approach to build lasting wealth while prioritizing personal freedom. Saket offers unique insights for tech professionals seeking their own path to independence.

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Watch episode on YouTube: https://www.youtube.com/watch?v=Rk93nWFWkcs


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This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

Announcer:

Freedom isn't the result of wealth; it's the foundation. Welcome to Wealth Independence, where freedom leads and real wealth follows. Through battle-tested strategies, hard-won lessons, and real-world experience, you'll discover how to accelerate your path to true financial independence. And now your hosts, Dustin Bailey and Adam Penn.

Dustin Bailey:

Welcome back to the Wealth Independence Podcast where freedom leads and real wealth follows. I'm Dustin Bailey here with Adam Penn. Adam, how are you doing today?

Adam Penn:

Doing good, Dustin. Excited. We're going to be interviewing Saket Jain.

Dustin Bailey:

I'm excited about this interview. Saket has a lot of experience in different areas. He's got a really cool story coming here from India. He has an MBA from Columbia and worked for Airbnb in a fairly high-level corporate role. I'm super excited to dive into the interview with him and hear his thoughts. He has some unique perspectives on things. As I said, he's had a lot of life experiences that influence the way he looks at the world, the way he looks at wealth building, and I'm really excited to bring his thoughts to you.

Adam Penn:

One thing I'm excited to hear from him is he's gone through a lot of changes recently. I think this episode will play really well to anyone looking to make that transition. He's moved from India with an engineering degree to work at a large company here, then became a kind of solopreneur starting his own private equity firm. Recently he's changed his life to be more focused on what he truly wants. Tying back into our goals episode, he's gotten some clarity on that.

Dustin Bailey:

That's exactly what I was going to say. I think this is good timing for this too, here in the early part of the year. This sort of stuff is on a lot of folks' minds as they're planning out the year and goals and everything ahead. If there's a time for transitions, people like to make new starts at the start of the year. I think this will be a great episode to hopefully help everyone set their mindset for that. So let's dive into it. Saket, how's it going today?

Saket Jain:

Hey, thank you guys. It's raining this morning. It's 48 degrees but it's raining, so I'm not sure if I should be happy about the 48 degrees or upset about the weather.

Dustin Bailey:

It's right on that verge of like, it's the cold rain, but it's not snowing, so you can't take advantage or claim it like "oh, it's snow." Just a cold, annoying rain.

Saket Jain:

I think snow is better. Adam, where you live, you would know what snow is like.

Adam Penn:

We get it up in the mountains. But hey, at least you guys don't have a massive hurricane ripping through there anymore.

Saket Jain:

That's true. I heard California had a 7.8 magnitude potential earthquake.

Adam Penn:

My whole house shook. We had an earthquake about a week ago or so.

Saket Jain:

Time to move out, buddy.

Adam Penn:

My doorbell started ringing. Anyway...

Dustin Bailey:

There's something to be said about the fact that this happened and this is the first I'm hearing about it. Adam, this was apparently such a normal event that you didn't even feel compelled to say anything about it.

Adam Penn:

It's just an earthquake - it happens.

Dustin Bailey:

If that happened here, I'd be running around telling everybody. People would be in chaos in the streets.

Adam Penn:

People didn't come to hear us talk about the weather, Saket. We wanted to talk about your journey to becoming an investor. You've made quite a few changes from migrating here to being an Airbnb executive to running funds to doing venture capital, selling insurance for a bit. You've been all over the board. Can you walk us through some of your story and maybe some of the highlights?

Saket Jain:

The key is I'm somebody who's always chasing freedom, and I'm not afraid of change. I say jokingly, I've lived in this country - if my accent and name didn't give it away, I grew up in India - came here about 23 years ago and I've changed 25 addresses, physical addresses. I say jokingly that I'm chasing something and until recently I didn't figure out what it was. I think it's really the sense of freedom. If I feel constrained in an environment, I'm going to make a move. That's just how I'm built right now. The changes you mentioned are really part of chasing what freedom means for me. I think I'm still evolving in understanding what it really means. Maybe I thought it was this, so let me try that. So far everything I've done has worked out in my favor monetarily, which is great - I'm thankful for that. But the outcome of those changes wasn't always what I was looking for in terms of freedom. In 2017, I got laid off for the first and only time. It shook me to my core. I don't know if you have immigrants in your audience, but especially for Indians, we think we're super smart and can never get laid off. I was no exception. On paper I'd done everything right - I went to IIT, one of the most prestigious engineering institutions in India, then Columbia for my MBA. How could someone like me get laid off? But it happened due to a merger where the whole division was laid off. I say that to make myself feel better, but it doesn't matter - I got laid off. That was my first rude awakening. I had heard intellectually until that point that jobs aren't secure. I'd read Rich Dad Poor Dad and all that stuff. But until that incident happened, I didn't truly internalize what it means that a job isn't secure. Jobs provide a stable paycheck while they last, but they can become insecure at any moment just like anything else in life. That's when I really started my financial journey - understanding what freedom meant and freedom from the shackles of corporate jobs. This wasn't about chasing $100,000 vacations on private jets. That was never the intention.

Adam Penn:

We all want a private jet. You don't have to hide that.

Saket Jain:

That's perfectly fine - I want two of those. But it wasn't about chasing that. I wanted to wake up in the morning doing what I love, even if it meant making a little less. That was the start of the journey. For that journey, I needed to raise my floor, which essentially means if I stopped working then, I would have drained my savings. So I needed to raise my floor which, in Robert Kiyosaki terms, means increasing my passive income and passive cash flow. I went deep into real estate where we bought over 25-30 homes and sold some. I never rehabbed anything, Adam. You know I can't - the word rehab is foreign to me. You know I can't handle it when the word rehab comes up.

Adam Penn:

You called me the other day when your AC went out and I had to walk you through trying to get it turned back on.

Saket Jain:

I didn't even know what you were talking about. There were a lot of things there but I had no idea what you meant. So I never tried rehabbing, but I did buy a lot of turnkey properties. That's where I made my entry. I quickly realized that to do this at scale, it had to be in the multifamily area. So I did that for a few years and realized diversification is very important, both for myself and my investors. Then we launched - I mean you and I, Adam - launched an Airbnb fund a few years ago that's been doing fairly well. I've started venture capital in the medical devices sector, which is still in its infancy. Now my floor has been raised, which means if I stop working today, I'm in a better position than I was seven years ago. That still doesn't mean hundred thousand dollar vacations yet, but that's okay.

Adam Penn:

Something you said there was pretty interesting. Our audience includes a lot of tech entrepreneurs or tech employees working at tech companies, maybe with high W-2 income, who might be considering either passive investing to raise that passive cash flow like you mentioned, or transitioning out of their W-2. We've talked about some of my story and how I've been able to increase my passive income above what my W-2 was. I want you to talk about how with each of these changes you had some desire - you either wanted more freedom or more income - and then you changed again later. What was that desire? What did the change process look like and what was the actual outcome? Maybe pick any one of those transitions, since some of these people may have just had a W-2 job since graduating, always knowing what comes next because they watched everyone else do it. So what did this look like for you?

Saket Jain:

I'll tell you, in 2017 it was an evolving thing. I don't think I've settled on an ultimate goal because it's going to change anyway - the goalposts keep moving. In 2017, the goal was that I never wanted to be financially dependent on anybody else except myself, not even my family. That was the entire trajectory. Once I got into real estate, I realized that I was at Airbnb, and at some point this company would go public and I'd face RSU phantom taxes. So I explored whether I could use real estate to minimize those taxes, and I'm happy to report I basically minimized all the RSU taxes. Was that possible in 2017? I didn't know that going in. 2017 was about getting $1,000 or $3,000 a month in passive income. The goalposts kept moving because what we were doing was getting financial results. It was purely a financial objective at that point. Since then, it has evolved. You figure out a recipe to get there financially, and if you keep doing it, you'll keep making progress. But what's the end goal? Is it $20,000, $100,000, $1 million? The more I looked at it, the end goal was never financial for me - it's more about what kind of life I want to live. I architected that life pretty carefully recently. I realized that if I've changed 25 addresses in 23 years, retail isn't for me, period. Anything requiring operational involvement isn't for me. So I'm now making decisions based on what kind of life I want to live and what fits into that goal. I don't know if that answers your question, Adam, but that's really why the changes happened - because the goalposts have evolved.

Adam Penn:

That makes sense. You don't really know what's going to happen when you make that change. You have this ideal and where you are and maybe where you want to be, but the in-between is unknown. They talk about this a lot in Benjamin Hardy's book The Gap and The Gain - if you keep aspiring for something more, you never feel like you hit it. Maybe what you're saying is that your goal is to live the life you want and have that freedom. So you're taking that freedom and making decisions around it. It's kind of a focusing question that you're using to make decisions as you iterate through. So it's a focusing question that you're using to make the decisions as you iterate through?

Saket Jain:

It's important. Everyone needs to have a North Star. And if I may be bold - never have finances as your North Star. Money is a means to get there, whatever that is. If you need $1 million to get to your North Star, that's perfectly fine. If you can get there with $1, that's perfectly fine too. No judgment on anyone's path. But have a bigger North Star that keeps you motivated. As we all know, it's a game of snakes and ladders. You make ten steps forward, sometimes you may get two steps back, maybe ten steps back. Who knows where you're going to be? A friend of mine who's a day trader told me recently - you don't need to win every time, you just need to win consistently. That's exactly true in anyone's life. You don't need to always make forward moves. Sometimes you may have to take a step back to make two steps forward. As long as you're willing to make that trade-off.

Adam Penn:

What are some common mistakes you see professionals making when they're trying to make that shift to build passive income streams?

Saket Jain:

As an engineer by training and a consultant by profession, I can think from both perspectives. The engineering side of me wants to have a 20,000-row spreadsheet with 50 worksheets mapping out everything with certainty. I've done that before. The management side of me just wants the bottom line to make a decision. Now neither approach is right. Part of that is...

Dustin Bailey:

But...

Saket Jain:

Neither approach works for two different reasons. One is analysis paralysis - wanting to know everything about the deal, and by the time you're ready to jump in, the opportunity is gone. The flip side, the executive mindset, is just looking at the bottom line and making an intuitive decision. Unless you've done thousands of deals, you may not have built that intuition yet. That's probably the biggest mistake everyone makes, and a lot of it comes from their training. It doesn't mean you can't overcome it - it's just your training. The third thing is not knowing why you're doing something. My friend who's a day trader makes $5,000 a day consistently and has done so for the last five years. But is that path for me? I don't know. I'm not saying it's good or bad. I have to know whether someone else's path aligns with mine.

Adam Penn:

Some of what you brought up there, especially around having an engineering background and wanting to build a 20,000-line spreadsheet - we can all do some crazy spreadsheet math to try to figure it out. But at the end of the day, the real world hits. How do you balance that engineering mindset, or what principles from your tech background have you successfully applied to your real estate investing career?

Saket Jain:

Anyone in the tech sector already has a higher risk appetite than someone employed at a blue-chip company. When I joined Airbnb, I knew the company was good, but there was no guarantee it would go public or do so the way I expected. So I think anyone in that sector has already taken that leap of faith. That's going to work in their favor. I've been fortunate that as a management consultant, we were buying businesses from our clients. So I learned on someone else's dime. That may bias my answer in my favor since I've already gone through that analysis of needing a 20,000-row spreadsheet versus getting comfortable enough to make a decision. I learned under the tutelage of successful merger and acquisition professionals who taught me how to think differently. But if someone were starting today, I think the best approach is to partner with someone who knows what they're doing, like our funds. We're not saying every opportunity will work. That's the second thing - putting your last $50,000 in an opportunity isn't prudent. A friend of mine put $50,000 in a deal where the probability of success was pretty high. Adam and Dustin, I won't name the deal, but the fund had always paid for 12 years. You probably know which one I'm talking about. He put his daughter's college education fund in there, and the deal didn't work out as intended. He called me recently saying, "I don't have the funds anymore." I told him we could figure it out, but had he told me this was his only money for the college fund, I would have never taken it. Any sponsor will tell you a beautiful story about their opportunity - not because they're trying to deceive you, but because they truly believe in the deal. Otherwise, they wouldn't approach you. They're risking their reputation, their money, their time. They're putting a lot into the deal. They know what they know, but there are many unknowns in every deal. The best way to learn isn't to buy by yourself. I've done that and lost a lot of money. My first apartment deal was a portfolio of three complexes, 100 units each. I got all my Excel experts involved, combining multiple spreadsheets. I loved it. But it didn't work out because there was a slight nuance I didn't notice, and we lost close to $175,000 on that deal. You can lose money doing it yourself because these are complicated assets and deals. These are operationally challenging aspects that you have to be really careful about. Adam, there's no single thing from my career I can point to that helped me. It's more about understanding there's a time to learn and a time to earn. Right. So you can lose it if you're doing it yourself because these are complicated assets, these are complicated deals. These are operationally challenging aspects of the deals that you have to be really careful about. Adam, there's no single thing from my career I can point to that helped me. I think it's more about understanding there's a time to learn and a time to earn.

Adam Penn:

It seems like a lot of it is about finding the right partner and the right people to work with. It's a team sport. Maybe talk about what you look for when you start working with someone new or invest with someone new.

Saket Jain:

The biggest thing is this - when I used to hire for my management consulting company, I would always ask myself - can I sit with that person for 10 hours at an airport and still like them? Not want to end it all? That's the first test - can I actually deal with that person?

Adam Penn:

Someone the other day said it's the beer test - would you have a beer with this person?

Saket Jain:

Exactly. Would you be willing to spend time with that person outside of a deal? That's the first test. Then the second thing is about their experiences. The third thing, which may surprise you, is about their resilience. Because in an operationally challenging deal, not every day will be happy. There will be challenges. Again, it's a game of snakes and ladders - you'll take steps forward and backward. So how do they deal with setbacks? There was one person in my early deals that I had to constantly reassure. I love that person, but for my next partner, I wanted someone who would try to solve problems together rather than needing daily reassurance that everything would work out. So I think those are a few things. The third thing is really about whether they're putting their money where their mouth is. How much are they going to become a dead weight?

Adam Penn:

I've got one more question for you. You've been part of some Bidwell Capital deals, and our tagline is "building generational wealth." What does that bring to mind? What thoughts do you have or strategies do you recommend for building generational wealth? Not just $100,000 tomorrow, but maybe $100 million over the next 200 years.

Saket Jain:

Patience is one big virtue. There's no get-rich-quick scheme. There are many, but most of them are Ponzi schemes. I've been part of a few, so I know exactly what I'm talking about - this isn't from a book I read. If it looks too good to be true, don't get into it. There's always another opportunity to invest your money. But to directly answer your question, Adam, what does generational wealth mean? I think it means many different things. It's not just about money for me. When I think about legacy, I consider what values I'm imparting to my kids. If I have $100 million to leave to my two daughters and my wife, what exactly are we giving them - just money or actual values? It's a fine balance. From a purely financial perspective, compounding is crucial. As Warren Buffett said, time in the market is more important than timing the market. I'm borrowing that from someone much smarter than me. It's about how actively you're investing. If there's a decision between buying a $2 million house versus a $1 million house, but taking that difference to invest for the future, you have to analyze that carefully. Buying a house is a very emotional decision, so I won't say it's good or bad. I've fought that battle at home several times and never won. But it's important when you're making these bigger purchase decisions. I'm not talking about the latte factor - that's not the mindset I follow.

Adam Penn:

Warren Buffett said something similar - he didn't buy a couch once when he was with his wife because he calculated that compounded over 30 years, that thousand-dollar couch would cost them a million dollars.

Saket Jain:

Completely. But don't live your life making every single decision that way. There's a fine balance. Ramit Sethi talks about dials in life - you have to figure out your dials, some will be low, some will be high. I might be butchering it, but I think he wrote "I Will Teach You to Be Rich." I like his concept of dials where if coffee gives you happiness, don't lower that dial - keep it but lower something else. You're the decision maker of your own life. If you want to buy a couch, buy a couch. If you want to buy a couch, don't buy a couch.

Adam Penn:

Robert Kiyosaki in "Rich Dad Poor Dad" had a good story about Kim when she wanted to buy a car. Instead of buying the car, she bought a house that produced cash flow and then used that to make the car payments. Sometimes you can find ways to buy income streams that then can buy you the other things you want.

Saket Jain:

Adam, you just made me realize something I should have mentioned about wealth, borrowing from Kiyosaki since it'll resonate with your audience. There's a difference between net worth and cash flow. Make sure you understand that difference. I'm on all ends of the spectrum - venture capital is all about net worth with no cash flow. Real estate is about cash flow and then appreciation, at least the way I look at it. I'm not chasing appreciation in real estate, but in venture capital, I am. You have to understand where on the spectrum you are today and where you want to be. Kiyosaki also talks about measuring your net worth in terms of how many days you can live without working. You may have $100 million and be able to survive for the next hundred years - that's perfectly fine. Most of us don't.

Adam Penn:

But even then it's only the next hundred years.

Saket Jain:

Right. Then we're not talking about generational wealth. But if you have a cash-flowing asset, like our Airbnb fund, you can live on that cash flow. You may not be able to claim a $50 million net worth at a party, but you can claim you'll never have to work again. It's just a different perspective. My mind was blown when I first heard this concept. Financial freedom isn't that hard - it's just that everyone talks about needing $5 million before you can retire. Well, that number is arbitrary, something Wall Street made up.

Adam Penn:

You need to get cash flow. For listeners who haven't heard it, go back to episode V03 where we talk about equity versus cash flow. It's an interesting topic to dive into. Well, Saket, is there anything else you want to add before we wrap this up?

Saket Jain:

Be clear on what you want and be very intentional about it. Your audience may not know my journey, so it might help them - I spent about two years in a monastery back in India. This was after I came to the US and figured out the recipe to make money. Will I ever be a billionaire? Who knows? But I felt there was no challenge left, that there must be something more to life. So I went back to my roots to figure out who I want to be. I'm still chasing that and wondering what I want to be when I grow up. I don't think I'll ever grow up, but those two years in the monastery taught me a lot about myself. Take some time away from all this noise - even this podcast or thousand other podcasts. They're creating thoughts in your head. They're good thoughts, but ultimately it's noise. You have to listen to these things to get inspired, then turn off all the noise and let the universe speak to you. That's when you'll get your answer. I took a 30-day sabbatical recently. I work for myself, so there's no real sabbatical - every day is a sabbatical. But I completely shut off everything - no internet, no phone, no computer - and went back to India just to focus on myself for 30 days. The person guiding me through this noticed when I said I couldn't read a book or do anything, that the day felt less productive. I'll never forget what he said. He said, "Just look at the tree." I asked, "What do you mean just look at the tree?" He replied, "Just look at the tree. You don't have to do anything." For the first week, my mind was going crazy. I thought there must be more to life than just looking at a tree. Three weeks in - this may sound emotional - I looked at a spider web and cried for 30 minutes. It completely changed my perspective. Life lessons were reflecting in that spider web. How did the spider know where to connect the two ends? How did it figure out there would be wind? It's so beautiful when you think about it. This is what life is - you figure it out. The spider didn't know it had to make a beautiful web; it was just trying to survive. It was taking one step after the next. The reason I'm sharing this with your listeners is when you look at your life, look at a spider web. You have to figure out what your web will do for you, what life will do for you. If you're listening to your parents' noise, this podcast, my voice - these are all our perspectives we're sharing. I'm not saying we're lying; these insights have been life-changing for us. But ultimately you have to figure out what your spider web looks like. Only you. If somebody else calls it ugly, it doesn't matter because this is your web and it's going to work for you. So I'll leave your listeners with that note.

Adam Penn:

Thanks, Saket. Would you mind telling our listeners where they can connect with you?

Saket Jain:

For whoever in your listener base gives a rating to this podcast - it doesn't have to be five stars, any rating - and sends me a screenshot of that review, I'll personally give you a 20-minute free strategy session. I've stopped doing these because I'm in transition, looking for another change that's going to be very different from what I've done so far. Me and Nova will probably be partnering on this new venture. If you're on the path of figuring out what financial wealth means to you, what generational wealth means to you, and if my story resonated with you, send me the screenshot of your rating. I'll give you my calendar link. This is my personal cell phone number - I check it myself, no VA. If you send a screenshot to that number, expect a 20 to 30-minute strategy session with me at no cost. You can find me on social media, though I'm not that active given my recent changes like the 30-day sabbatical. I'm changing the direction of my life. My previous podcast episodes are online with many other nuggets I've shared. If you want to reach me on social media, LinkedIn is probably best - it's "TheSaketJain." I hate having "The" before my name, but I couldn't find anything else. That's just a lack of creativity. But that's where you can find me. If you ping me and mention you found me through this podcast, I will respond. If you ping me and tell me where you found me, I'll make sure to respond if you're coming from this podcast.

Dustin Bailey:

That's awesome. We'll make sure to include that information in the release notes. That's a very generous offer - certainly hope someone takes you up on it. We'll get all your information in the notes. This has been fantastic, Saket. We could dive into so many of these topics for hours, go down different rabbit holes. This was fantastic. We really appreciate your time today.

Saket Jain:

Thank you for having me here. These guys are the real deal - Adam and Dustin. I'm not saying it because Adam is my business partner. I love Dustin. They're great strategists themselves. Unlike me, they're on the younger end of the spectrum, so they'll give you insights that I probably don't and can't. So take what they're offering and at least look into it.

Adam Penn:

Awesome.

Saket Jain:

Thank you.

Adam Penn:

Thank you.

Dustin Bailey:

We appreciate it. We'll make sure to Venmo you the money for that plug later.

Saket Jain:

Let's keep collecting them. Thank you, guys.

Dustin Bailey:

Thanks so much, Saket.

Adam Penn:

Well, everyone, thanks for listening to our interview with Saket. Hopefully you found that as wonderful as we did and take him up on his offer for that consultation. The guy's just a wealth of knowledge. We're definitely looking forward to talking to him again shortly.

Dustin Bailey:

For sure, he had so many nuggets. We could have spent hours on any one of the things he said. He kept dropping insights that I wanted to interrupt and explore in detail, but there was just so much. He's got such a unique perspective on things in life and his story. That phrase "look at the tree" - that's...

Adam Penn:

Yeah.

Dustin Bailey:

I'm going to implement that in my own life, I think. There's a very deep lesson in that. Especially as we live in a world that prizes moving very fast, we can kind of get lost in things sometimes.

Adam Penn:

When I tell you to go take a hike, that's really what I mean.

Dustin Bailey:

I'm just going to go to my backyard and stare at a tree for a few minutes.

Adam Penn:

Well, appreciate everyone for being here. Remember, where freedom leads, real wealth follows. Join us next week.

Dustin Bailey:

Thanks, everyone.

Announcer:

Thanks for joining us on Wealth Independence. This show is for informational purposes only and is not financial, investment, legal, or tax advice and does not constitute an offer to buy or sell securities. All investments carry risk and investors should always conduct thorough due diligence and consult with qualified professionals before investing. Until next time. Remember, freedom leads and real wealth follows.

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Adam Penn

Host
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Dustin Bailey

Host
Contributor

Saket Jain

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