In this episode, Hilmarie sits down with David Awad to explore how small, intentional decisions compound into extraordinary outcomes over time. From being fired from several early jobs to building a career that spans software engineering, venture capital, and law, David shares why success is rarely about a single breakthrough and almost always about consistent choices made over years. The conversation challenges conventional thinking about careers, money, and achievement. David explains why saying "yes" to opportunities creates luck, why understanding how the world and financial systems work leads to better decisions, and why defining your own version of success is far more important than chasing society's expectations. He also shares how failure, when viewed through the right lens, becomes valuable feedback rather than something to fear. A standout moment is David's perspective on desire and happiness. He argues that many people spend their lives pursuing money as a proxy for experiences they could already have through different paths. By identifying what you truly want, rather than what you think you're supposed to want, you gain the freedom to design a life around purpose instead of comparison. David also reflects on unconventional career choices, including pursuing a law degree after becoming a software engineer, and how combining seemingly unrelated disciplines created opportunities few people could have predicted. His insights into AI, investing, continuous learning, and personal knowledge systems reveal how curiosity can become a long-term competitive advantage. At its core, this episode is about ownership, intentionality, and the power of compounded decisions. David's story is a reminder that your starting point never defines your destination, and that lasting success comes from making thoughtful choices, embracing failure, and continuously investing in the person you're becoming. About The Guest David Awad is a software engineer, venture capitalist, attorney, and technology advisor working at the intersection of software, investing, and emerging technologies. His career combines deep technical expertise with legal and financial insight, allowing him to advise startups, investors, and founders on software development, AI regulation, intellectual property, venture investing, and technical due diligence. He also serves as a fractional CTO and works closely with venture capital firms evaluating technology companies and high-growth startups. Known for his unconventional career path, David has built a reputation for challenging traditional ideas about success, education, and decision-making. After early career setbacks, he intentionally combined software engineering with legal training, creating a unique skill set that bridges technology, business, and law. Today, he shares practical insights on investing, AI, personal growth, and designing a life driven by curiosity, freedom, and long-term thinking. Quotes 7:15 - The art of investing is understanding what has value. 11:19 - Always produced better outcomes for the people who believe that they can make the changes versus not believing so, even if it wasn't true. It would at least empirically appear that believing that it was the case, that you could change your outcomes, does produce vastly more positive outcomes. 22:30 - Calm mind, fit body, and a house full of love. Those things are not easy, and they're very, very important. 27:20 - The only other thing that's helpful on top of that is just read a lot of excellent books. There is so much value in just sitting down and reading, not random books. 31:12 - The most useful thing about success is that you get to decide what it is. You get to decide when you're successful at the end of the day. You set the mark for yourself, you aim for it, and if you hit it, that's all that's required. 34:33 - I've learned simply to desire less things, to focus more on just making sure that more options are available than anything else. Not having handcuffs is a very wonderful thing. And lots of lots of people should have be able to experience that. 47:04 - Freedom is having as many choices as possible. Ideally, the number of choices should increase with time. Useful Links Website: https://davidaw.ad/ LinkedIn: https://www.linkedin.com/in/davidaawad/ Instagram: https://www.instagram.com/realdavidawad/ X: https://x.com/realdavidawad/ The Matrix Green Pill Podcast: https://thematrixgreenpill.com/ Please review us: https://g.page/r/CS8IW35GvlraEAI/review