Lessons from James Beshara

James Beshara, an entrepreneur, investor, and thinker, has shared a wealth of knowledge over the years through various platforms. His insights, often drawn from his experiences founding companies like Tilt and Magic Mind, offer valuable lessons on entrepreneurship, personal growth, and navigating the complexities of modern work.

Entrepreneurship

On the three pillars of a successful company: To build a company of massive significance, you have to create a product people love, figure out growth and distribution, and develop strong business mechanics underneath it all. [1]
The right order of operations: "I thought, okay, I've figured out something people love and now I'm going to grow it as fast as I can...we can monetize down the road." He later realized the correct order is: "create something people love, build great business mechanics to support it, and then grow it." [2]
On 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.” [3]
The expanding role of a CEO: "Instead of one boss, you have 70 employees who are your bosses, or 10,000 customers who are your bosses." [3]
The power of a co-founder: On the journey of building a company: "it's going to be so hard that... you really need a co-founder." [4]
On the scalability of software: While working in poverty alleviation in South Africa, he saw "the role software could have in impacting the world broadly... It felt like the most scalable way to effect change.” [2]
On D2C startup advantages: "You have flexibility advantages as a small startup that Procter & Gamble doesn't have. You have the efficiency that technology startups don't have; two people can really take it to $10, $20 million in sales." [5]
The importance of a niche: Beshara's experience with Tilt showed that even with a broad potential market, focusing on a specific, passionate user base is crucial for initial traction. [4]
On the evolution of crowdfunding: "What will crowdfunding look like in a mobile world?" This question was the foundation of Tilt, aiming for a "bite-sized simplified version of crowdfunding." [4]
The value of early feedback: With Magic Mind, he was "asking for the negative feedback for two years" and waited for 200 subscribers before even naming the product, a stark contrast to his approach with Tilt. [2]

Failure & Resilience

Embracing "poison": "If you want to become immune to to poison you've got to eat a little bit of it every day and go into it you know head first into that bad news and that's how your product gets better your team gets better you get better." [6]
The danger of seeking validation: Premature growth is often driven by "insecurity and the need for external validation." [1]
Learning from mistakes: "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.” [3]
Failure as the best teacher: "Failure is the best teacher. And success doesn't teach anything." [6]
The journey of building and selling a company: "The above the line version would be that I sold the company to Airbnb. The below the line version... is that it was a tumultuous experience to build and sell a company." [7]
The pain of a crumbling company: "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." [7]
The loneliness of failure: The experience of his company struggling felt like a "solitary journey of feeling like, ‘Gah, no one's ever been through anything like this.’" [7]
Getting comfortable with the worst-case scenario: This is a tactic to "maximize the chances of the best case scenario." [8]
The importance of talking about the "below the line": He started his podcast to discuss "the 90% of the story you don't read about or hear about anywhere else." [9]
Resilience in the face of market volatility: He created a podcast episode to help founders manage their psychology during economic downturns, drawing from his "experience of making nearly every mistake in the book." [8]

Decision Making & Growth

Decisiveness over decisions: "It's not the decision that matters it's being decisive... one of the greatest things you have going for you in starting a start-up is that you have rapid feedback loops." [10]
The only wrong decision is indecision: A Marine Corps quote he often references. [10]
Focus on the trend, not the number: "It's not the number it's the trend if I wrote a book for startup founders i would i would write it's not the number it's the trend." [10]
The journey is the destination: "There was probably more anxiety the day after we signed our term sheet with Andreessen Horowitz than any day prior. The journey is the destination... that is really where the soul of the work lives." [11]
The illusion of arrival: Getting a big investment isn't the end goal. He recalls thinking a company that got a major investment had "made it," but that company is no longer around. [4]
On angel investing: "I knew that I was going to learn, no matter what." [5]
A framework for investment decisions: He ranks founders, product, growth understanding, and the size of the space on a scale of one to five, and invests if the average is over four. [11]
The power of compounding decisions: "The energy that is well-placed is the energy that generates more energy." [12]
Return on luck: "The most successful companies are not luckier. It's not about luck, it's about return on luck. It's what you do with your luck opportunity." [12]
Avoiding the competence doom loop: "We often take a job on a whim and eventually get increasingly good at something we were never meant for in the first place. The world tells you that you're competent and paid well so you must be happy." [13]

Work-Life Balance & Productivity

The power of boundaries for balance: "To get balanced on a surfboard. You need momentum. To get momentum, you need consistency. To get consistency, you need routines. Routines always come down to boundaries." [10]
The single best piece of advice: A sleep doctor told him to wake up at the same time every morning, which "set my biological, hormonal clock." [10]
The magic of "No Meeting Wednesdays": This practice leads to his "favorite day of the week by far" and allows for deep work. [10]
The problem with over-committing: “Over-committing is just lying to yourself that you can do more than you probably can.” [3]
The benefit of asynchronous work: Inspired by Sahil Lavingia, he adopted an "asynchronous" working style, which he found "life-changing." [1]
The myth of the hustle: Working 90-100 hours a week, he fell into a cycle where the "antidote to that wasn't healthy choices. It was more caffeine." [12]
The importance of mental wealth: One of his five guidelines for navigating tough times is to "Manage your mental wealth." [8]
The power of honesty in reducing stress: “Perhaps the most important thing you can do for reducing stress is being honest.” [3]
Leaning on your team: "Don't try to keep it all contained when you can lean on your team. People want to help." [3]
The value of quiet time: He aims to wake up early to have "solo quiet time" before his children are up, finding it to be the "most powerful time of day." [14]

Philosophy & Life

On worldview: "We don't see the world as it is We see the world as we are So whatever world view that we have... very few of us even articulate our worldview." [15]
The core human desires: "Vidanta explicitly states that what we really want at the foundation of everything that we're pursuing is peace and prosperity. Not one or the other. but both." [11]
The wisdom of Vedanta: He hosts a daily podcast on Vedanta, the "world's oldest philosophy," which he finds "so faking practical so helpful." [15]
Life begins at 40: He frequently references the Carl Jung quote: "Life begins at 40. The rest is just research," interpreting "research" as the process of "exhausting so many of our desires through experience." [16]
Finding your dharma: "If you pursue your... nature you'll you'll attain immediate peace. and if you are pursuing your paradharma your foreign something that's foreign to you... it is a disaster for your life." [14]
The preciousness of life: After his sister's passing, he "approached each day feeling like life is extremely precious." [7]
The transformative power of fatherhood: "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." [7]
The prison of public opinion: "The four-word prison: what will people think. The difference between a palace and a prison is who owns the key." [13]
On self-awareness: "There is nothing in the world that can disturb you except yourself. You are the architect of your fortune and the architect of your misfortune." [15]
Wisdom as seeing the end in the beginning: A concept from Vedanta that he finds "so crazy cool." [15]

Learn more:

Lessons from James Beshara

Entrepreneurship

Failure & Resilience

Decision Making & Growth

Work-Life Balance & Productivity

Philosophy & Life

Written by Antoine Buteau

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