Podcast Launch: Below The Line

On April 2nd, I launched a project I had been working on for the last several months.

What started as an inner voice to research and write a book on a specific set of topics around the psychology of creators, founders, and leaders (and finding the optimal psychological approaches to something that can, well, destroy your psychology at times), I was told by two friends that were authors themselves, Eric Ries and Tucker Max, to record each conversation and release the conversations as a podcast in lead up to publishing the book… So that’s what I’ve decided to do.

Check out or subscribe to the full podcast here — Or listen to the intro episode to see what the podcast will be about here (and to see why this entire personal site is just a partial story): https://podcasts.apple.com/us/podcast/below-the-line-with-james-beshara/id1457400066?i=1000433676439

Below is the transcript from this first episode (I’m using descript.com for transcription, so it’s unedited and likely has grammatical issues):

James: Alright. Episode 1. Below the Line. Felt only fitting for me to spend a few minutes in this first episode, to kick off this podcast, telling you a little about myself, and a little about why I decided to start this podcast, and a little bit on what the podcast will cover.

So, I’ll break it down in that order.

A little bit on myself-my name is James Beshara, and I am an investor, advisor, founder, general start up helper, here in San Francisco, California. And, I have been blessed with getting to meet some of the smartest, brightest, most insightful individuals when it comes to building companies in the world, in my career. And, it’s been so valuable to me to get to chat with founders, mentors, advisors, and peers-people that I admire-and just get to have a 30 minute conversation with, and hear the real versions of a lot of the stories we get partial versions of publicly.

In other words, you get 10% of the story in a news article, or an online interview. But, you miss out on 90% of the real version of the story and the meat and what I found so meaningful as a founder, myself.

A few years ago, I sold a company, and the above the line version would be that I sold the company to Airbnb. The below the line version, the other 90% of that story, that I don’t necessarily talk about, but I think a lot about, is that it was a tumultuous experience to build and sell a company. Especially in the way that we went about doing it. 

About four years into building the company, it was valued at $400MM. And, we were flying high. And, it was a lot of hard work, a lot of luck. We got to that point. But in the last 18 months of the company’s life, after spending 6 years of building it, it kind of crumbled right in front of me. And, it fell apart right before my eyes. And, what I experienced was this solitary journey of feeling like, “Gah, no one’s ever been through anything like this.” And I certainly didn’t feel like I had people around me who had been through anything like that. And, it was this journey of building something that was very close to being really significant. Then to selling it for a fraction of the capital we raised for it, and essentially a fire sale, that it was this journey that I went on that felt like I could really use someone to guide me. Help me avoid the mistakes that I made, and/or be there in the fox hole with me. Gave me the courage to get through some really harrowing moments. It wasn’t until I got on the other side of that experience that I learned from founder after founder who reached out, telling me about their similar experiences. 

And I just wish, “where was this insight, this wisdom, or just someone to help me navigate this while I was going through it?” Or, to help me before I made a number of mistakes that put us in that position in the first place. I just kept hearing story after story of founders of the real versions of their stories. Not a perfectly packaged version, but a real version that I thought to myself, “Man, I’m going to share my experience early and honestly with anyone and everyone it could potentially help”, and just kept getting put in touch with founder after founder that was going through a really tough time. I loved being able to share my experience with them in a really honest way, and in a way that I really felt and heard was valuable for them to hear, and really rare for them to hear.

The thoughts going through my head were, if you could only have heard person x, y, z, etc, their real story, real version, you’d realize it’s not so different from your own. And if you could apply the mental framework they have to learn from scratch most of the time, you could see the way around the situation you’re in, or avoid it altogether.

And it became an obsession of mine, actually, to start sharing my experiences as well as these real stories I kept hearing with early stage founders. The real version of my own story, and the real version of these creation myths behind these seemingly infallible companies, and more than that, it was an obsession to learn the different mental frameworks that each leader thought a lot about, but rarely talked about.

I immediately felt like I should chat with everyone I could, and compile these conversations in a book, perhaps. And gather and share the real versions of these stories, and the mental frameworks these world class leaders developed to navigate their own harrowing, and often tumultuous journeys, would make for potentially good reading. I know it would have made for great reading for me. 

So, two advisor’s of mine, Eric Ries and Tucker Max, who have both written multiple New York Times Bestsellers, both had the same advice when I told them about this. And that was that we should record all these conversations and release each one as a podcast as I interview everyone over the next 18 months or so.  So here we are! We are going below the water line to see the real conditions that put this leader in the seat across from me. As well as going below the water line to peer into the depths where the great decisions where these individuals have come from. Going beneath the surface to see what’s really going on.

So, that’s a little bit on the why, and why it’s called Below the Line. Now, onto the what.

The first few episodes, I’m absolutely going to just be figuring out what exactly I’m doing. But, on that what, and what I am going to start with, is a handful of standard questions, and then each conversation is going to ebb and flow naturally and I really want them to. But, here are a few of the questions I hope to touch on with a few of my guests and we can start by putting me under the fire as well and seeing how it goes.

First thing, first question that I’m really looking forward to asking my guests is, tell me three stories in your life that have shaped who you are. So, for me, the three stories that come to mind, the first one, is when I was 15, my close friends know this, but I want to share with you all, because the purpose of this whole concept is to dive deep into the topics below the line that founders don’t typically share, but things they think a lot about. And one of the things that shaped my life in a major way that comes to mind, something that was very formative for me when I was 15, was my oldest sister, who is my closest sibling, she was 3 years older, she passed away. And, this is going to be a hallmark of the conversations in my podcast, so I’m not going to leave out details, I’m going to tell you the honest details and give you the honest answers, because I think these stories can be so meaningful when shared honestly. 

So, my family struggles with mental illness and depression. And I’ve been depressed at various points, but for the most part, I’ve been very lucky to dodge the bullet that affected my sister, and she had deep depression when she was 18. And, she took her own life. It affected me in so many ways, so many countless dimensions for sure. But, it was something that I can consciously say that I’m certainly aware of, is the fact that from that moment and experience, I approached each day feeling like life is extremely precious. And each day that we have is extremely precious. So, I try to make the most out of every single day that I have. And that’s certainly one of the most formative experiences that I’ve ever had. Because that cliche of life is precious, sometimes you need a really intense experience to appreciate it. So, that’s the first story.

The second story is I can probably sum up my 20’s with one story. I failed a lot, in my twenties. So, throughout these episodes, you’ll learn more and more about my story, and my background. But, suffice it to say, short version of something that I think a lot about and I’m eternally, both of these first, well three, eternally grateful for. But, when I think about what has shaped my life and tried to distill it into three key stories, one that certainly is at the top of the list, is that in my 20’s, I was just trying things left and right. I mean, I still am. 32 now, but ten years of building companies, about 12 years total, since I started college, of building things. It’s hard not to look back on my 20s and not think, wow, that was just a lot of trial and error, and basically a lot of error. And, it is, I am extremely grateful for it. 

But starting three companies, none of them exist today. I started countless projects, none of them really exist today. And, my summary on something like LinkedIn will give the above the line version which is that I sold the company to Airbnb, and then have invested in a few multi-billion dollar companies as an angel investor. And, yes that is true. But it’s not the story that I think a lot about and it’s certainly not a story that has helped shape my life compared to the below the line version of, just a decade of trying things constantly, and then usually not working out.

I love that I’ve had that experience because I feel like it’s the foundation of everything I try to fail and fall forward with it will be the foundation for anything I do for the next six years of my career. Each step forward was certainly movement. It was progress, in its own way. But, it’s something that I look back on and think there wasn’t much to show for all of the activity of that decade. But I do have a reservoir of scars and earned insights and things that I think will be extremely formative for the next few decades. But, I’m also comfortable where I am in life to where I don’t need it to be. So, it’s interesting. One part of me says it’s foundational, another part of me says I’m exactly where I’m supposed to be, doing what I’m supposed to be doing. It’s just a culmination of ten years of trying things and then not working out, but me being able to let go of needing them to work out. Realizing just the experiences alone have made them worth it.

Alright, story number three. Last story that has helped shape my life, and one that I think a lot about, but don’t talk a lot about, is my daughter. I mentioned a few minutes ago that there are cliches out there that you just need to experience to realize and every cliche about having a child is absolutely true. It is so crazy. The phrase melt my heart, I had no idea what people were talking about, when they would say melt your heart, but I see my 15 month old walking towards me in the mornings, and there’s no other way to describe it. It’s so unreal. And, it makes me wish that, me and my wife, we had started earlier. Because it is such a transcendent experience. People here in Silicon Valley, they talk a lot about, or at least, it’s a topic du’jour, psychedelic experiences. And, I gotta say, the most mind altering experience of my life has actually been in having our daughter. It is hard to think of anything more mind bending than having a child and re-orienting your perspective. At least for me. And 15 months in, I know it’s going to be the most formative experiences of my life. Just, I look back, and I can see this clear break and split in my life of before and after. And, before thinking about myself, or my wife and I, and our life to, just right after, just thinking about my daughter. And thinking about her life, and completely re-orienting my perspective.

So, those are three stories that have shaped my life, and that’s a question I can’t wait to ask my guests. 

Another question that I plan on asking my guests is, and it’s similarly related to the first one, and it’s what is something you think a lot about, but you rarely get a chance to talk about? Well, my quick answer to that is, I think a lot about philosophy. And, those close to me know that I think a lot about it, but it still never comes up professionally. Something that makes sense to talk a whole lot about. But, if you care a whole lot about philosophy, and you’ve got great resources for it, shoot me a note at askbelowtheline@gmail.com. It’s something that I’m always looking for great online, great offline resources for some of the best philosophy is absolutely in books. Some is just best found by sitting quietly under a tree, to be honest. But, I’ve actually found YouTube to be a great resource for diving into interpretations of different great philosophers over time. There are a number of lectures from Stanford or Yale, from their philosophy departments that you can listen to on YouTube. It’s really, really such a great resource. 

And, personally, and over the last 5-6 years, I’ve become most interested in Eastern philosophy. I grew up learning about Western philosophy and I grew up Catholic. And, the Western sense of philosophy is very GrecoRoman based. And, there’s phenomenal wisdom within things such as Greek philosophy. But, I’ve come to appreciate things like Eastern philosophy, and I owe a lot of that to my parents. My dad taught us to meditate when we were very little, when I was about eight years old, and introduced us to Buddhism at a young age. Even though we were at church every Sunday, and we were very clearly raised Catholic, there was an interwoven awareness of the tenants of Buddhism. And, I really appreciate that. It was kind of a quirky thing in Dallas, TX in the 80s and 90s to get exposed to, but when I graduated school, and I lived in South Africa for a few years, on my own, pretty solitarily for awhile, I began to look much more closely at my world views, and some different ones out there that I hadn’t given a whole lot of thought to. I began to look more closely into Eastern philosophy. The philosophy that was introduced casually as a child. 

I really love Buddhism and many of the tenants within Buddhism, and an adage about Buddhism is that it’s Hinduism made for export. So, Hinduism starting in India, and Buddhism also beginning in India, and making its way to China and Japan. Hinduism is the underlying philosophy of Buddhism. The underlying philosophy of Hinduism, which is equally fascinating, not the characterized version of 3,000 gods, and the version that you learn in 20th century America. But, the intellectual tenants that you learn of Hinduism are phenomenally, just super deep and thoughtful. 

And loved exposing myself to that as well as Buddhism, but actually, the philosophy that I think immensely about, or more so than any other, is the source of Hinduism, which predates Hinduism and it is a school of thought called Vedanta. And, it’s something that I may weave into the episodes here and there. But it is just very thought provoking world view, and one that I find extremely fascinating. And I love thinking about this stuff because I think there’s so much wisdom in the thousands of years of this type of Mythology. Mythology with a capital M. I don’t want to take anything away from it by calling it a mythology. There’s so much wisdom in these stories that have lasted 5,000 years. So much wisdom in Christianity as well. There’s so much wisdom, and there’s a reason these stories have lasted longer than any empire or country or basically any human structure. Anything we’ve created. When you take a deep look at them, and not trivialize them, but take a deeper look at them, at moments in life when I could have let them go, I always found something to appreciate about them. So, that’s something I think a lot about.

So, that’s two of the questions I’ll ask my guests, and I hope to dive into these topics with them any many more topics that they think a lot about, but the ones they might not get a chance to talk a lot about.

Like I said, the episodes will all differ, and they will all ebb and flow with natural conversation, as they should. But as part of the preparation for this book, it will all focus on learning about the stories below the waterline for these individuals. And, focus on the versions of the stories you don’t hear these founders or leaders talk about, but trust me, they are the versions they think a lot about.

I also plan on touching on the research from psychologists, neurologists, researchers, sports psychologists, executive coaches, everyone I can chat with that will provide insights for how the 10 million plus entrepreneurs in the US alone should and could strive to approach each day. And ways that can help them find their flow and meet their potential.

So I’m really excited. With that, I invite you to join me in these conversations, and I really appreciate you taking the time to listen. Thanks!


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