James Beshara on Mental Health, the Realities of Entrepreneurship, Radical Honesty, Creativity, and More – Paradox Podcast (Part I)

Key Takeaways

  • How to mitigate stress:
    • Practice the art of under-committing
    • Start a meditation practice
    • Block off time to think
    • “Perhaps the most important thing you can do for reducing stress is being honest” James Beshara
  • On the realities of entrepreneurship:
    • “The conception is that you own your own destiny, or you’re your own boss, or you have freedom… That just wasn’t my experience in creating anything I did. You’re always beholden to the audience, customers, or whoever you’re creating for.” – James Beshara
      • And when your company gets big enough – “Instead of one boss, you have 70 employees who are your bosses, or 10,000 customers who are your bosses.”
    • The human body isn’t designed to withstand the long-term stresses that come with building a successful startup

Books Mentioned

Intro

  • Hosts – Kyle Tibbits (@KyleTibbits) and Alex Khan (@MrAlexKhan)
  • James Beshara (@jamesbeshara) is the host of Below the Line, a new podcast taking the podcast industry by storm (check out the Podcast Notes)
    • James co-founded Tilt – the company ended up being acquired by Airbnb
    • James is also an active angel investor. To date, he’s invested in companies like Gusto, Halo Top, and Mercury Bank.

The Podcast Industry

  • “It’s so wildly under-discussed how crazy of a medium this is; it blows my mind” James Beshara
    • Check out James’ recent Twitter thread on the state of the industry
  • “I think we’re early. We’re nowhere near the peak.” – Kyle Tibbits
  • It’s similar to how Amazon played out:
    • Back in ~2011-2012, the company was ~14 years old, but James knew they were just getting started (he thought they would double their market cap over the next 18 months)
      • As it turned out, they doubled their market cap over the following 19 months

Radical Honesty

  • If you listen to James’ podcast, you’ll pick up on his refreshing level of honesty
  • How to mitigate stress:
    • Practice the art of under-committing
      • “Over-committing is just lying to yourself that you can do more than you probably can” – Alex Tibbits
    • Start a meditation practice
    • Block off time to think
    • “Perhaps the most important thing you can do for reducing stress is being honest” James Beshara
      • Related to this, give Lying by Sam Harris a read
      • “Over the last 4-5 years, I’ve gained more and more appreciation for just how powerful being honest is”
  • When you’re honest about what you’re going through, the universe tends to work in mysterious ways to help you out
    • When you’re honest, it tends to elicit the right circumstances/scenarios for what you truly need – solutions, comfort, and empathy tend to manifest out of thin air
  • But things weren’t always this way for James:
    • “Probably for 90% of Tilt… it wasn’t like I was going around lying, but I was certainly keeping things close to my vest” – James Beshara
  • “When we’re lying to ourselves or others, you’re just adding so much sh** in the way of you being able to see the world and others being able to see you” James Beshara
    • Stop lying (stop adding dirt to the windshield of your life)
  • Justin Kan preaches the idea of “sharing the burden of what you’re going through”
    • James adds – “Don’t try to keep it all contained when you can lean on your team. People want to help.”
    • Check out the Podcast Notes from James’ interview with Justin Kan

The Spiritual Side

  • James was raised Catholic in Dallas Texas, but over the years has navigated more and more towards eastern philosophy
  • In his 20s, James took an interest in meditation
    • “When I started looking at it beyond a practice of mindfulness or meditation in the mornings, I developed an appreciation for the psychotherapy within Buddhism all the way to my favorite philosophy called Vedanta” – James Beshara
      • James describes Vedanta as a “philosophy on how to think and how to not engage in self-sabotage”
        • “That philosophy, or psychotherapy, was really therapeutic when I was going through really stressful times in building a company.”
  • James, who now lives in San Francisco, still attends church every Sunday

Creativity

  • James has always had a creative side – he’s a musician, author, startup founder, and now podcast host
    • “The podcast, I think, is my favorite creation to date” – James Beshara
  • Where did his creativity come from?
    • As a young kid (~5), James loved to draw and would frequently enter art contests
  • James’ wife, whom he met when he was 24, is also an artist

Entrepreneurship Misconceptions | The Reality of Being a Founder

  • “The conception is that you own your own destiny, or you’re your own boss, or you have freedom… That just wasn’t my experience in creating anything I did. You’re always beholden to the audience, customers, or whoever you’re creating for.” – James Beshara
    • And when your company gets big enough: “Instead of one boss, you have 70 employees who are your bosses, or 10,000 customers who are your bosses.”
  • Before Tilt, James built Dvelo.org in his early 20s – the company focused on fundraising for non-profits
    • James was forced to shut it down due to a lack of interest:
      • “I remember, even with that, it was so stressful. I had just told all my friends and family about this thing… then crickets… It was so embarrassing.” – James Beshara
  • “I’d say out of the 5 years of building Tilt, there were probably only 4 months when I said, ‘Hey, we’re ahead of the 8 ball.’ For the other 4 years and 8 months, it was every night and every morning. I feel so bad for all my friends, my wife, and my family. I always felt like we were behind the 8 ball.” – James Beshara
    • (For background, Tilt was basically a mobile version of crowdfunding – they were competing with Kickstarter and GoFundMe)
    • The human body isn’t made for this kind of stress
      • “I only understood this afterward, but my physiology was SO wrecked. My cortisol levels, the stress hormone, had been elevated for 5 years.”
    • What makes it tougher is that so much of your identity as a person is tied up in the company’s success
    • “There were moments where I was breaking down in tears in the bathroom of my wife’s parent’s house. I couldn’t stand up and was thinking, ‘What the hell is happening? How will I get through this?'”

It’s Never the Individual

  • Behind every great company, podcast, whatever, is a team of people making things run smoothly
    • But that’s not the narrative we hear – great startups get reduced down to the story of the founder/individual
  • Despite what you think, you likely CAN’T do it all yourself

The Nuance Machine

  • “We’re living in the nuance machine, which is podcasting. That’s why I love this medium so much… Audio and conversation are so great for nuance. That’s why I love podcasts; it’s so replete with nuance, and you can actually spend 5 minutes explaining a concept.” – James Beshara

Are shorter podcasts better?

  • Check out this tweet from Naval Ravikant
  • James, who frequently releases 1.5-2 hour podcast episodes, doesn’t necessarily agree with Naval’s method of releasing short 3-4 minute audio clips on his podcast feed
    • “I really love going deep into someone’s story. I don’t agree with the snippets. I think snippets are great for collection. Perhaps if you were trying to collect factoids and little bits of information…. but I don’t want to accumulate. I want to explore different worlds.” – James Beshara
  • That said, James says of Naval – “He’s probably the clearest thinker in the realm of technology”

Angel Investing

  • James made his first angel investment back in 2013
    • At the time, James was 24 and in Y Combinator when the co-founder of Gusto asked him to invest
      • James didn’t have much in savings, but managed to write them a check for $20k – Gusto is now valued at more than $2 billion+
  • James has since doubled down and is now doing angel investing full-time
    • Why?
      • “The last 18 months of Tilt’s life involved trying everything we could for a revenue model… Everything we were trying in 2015 and 2016… nothing would stick. So, we ultimately had to sell to Airbnb. It was basically a fire sale. 95% of our value was cut down.” – James Beshara
        • “I did all these things I wouldn’t come within 10 miles of doing again with my next company. I made all these mistakes and went through this painful process… I just wanted to help prevent this from happening to other people as much as possible.”

Additional Notes

  • James made it through Y Combinator with Tilt – shortly afterward, Sean Parker showed interest in buying the company (when they only had 5 employees)
    • James turned him down, but a few years later, just like in The Social Network, James found himself meeting with Sean at a sushi restaurant when Sean said he wanted to invest (James was only ~24-25 at the time)
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