Every Business I Tried Before Making My First Million
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode, Sam Parr walks through approximately 10 different businesses he attempted before making his first million at age 31. From flipping sports equipment in high school to running a hot dog stand with an ex-con named Rydell, Sam's journey illustrates the messy reality of entrepreneurship. (00:00) He shares how most of these ventures failed or barely broke even, but each taught him valuable lessons about copywriting, sales, and project selection that eventually led to his success with The Hustle newsletter.
- Core themes include the importance of developing money-making skills, embracing scrappiness when necessary, and learning proper project selection through process of elimination.
Speakers
Sam Parr
Sam Parr is the founder of The Hustle, a business newsletter that grew to over one million subscribers before being acquired. He currently runs Hampton, an exclusive community for entrepreneurs, and co-hosts the My First Million podcast. Known for his direct approach and copywriting expertise, Sam has built multiple successful businesses after years of failed attempts.
Shaan Puri
Shaan Puri is a serial entrepreneur and investor who co-hosts the My First Million podcast. He previously founded multiple companies and has experience in Silicon Valley's startup ecosystem. Shaan is known for his frameworks-based thinking and ability to break down complex business concepts into actionable insights.
Key Takeaways
Master a Money-Making Skill Before Everything Else
Sam emphasizes that successful entrepreneurship requires three core components, with the first being a money-making skill. (12:19) Through his various ventures from hot dogs to newsletters, Sam developed copywriting and marketing as his primary money-making skills. This wasn't theoretical learning - it was practical, hands-on experience from selling hot dogs on the street where he had to "wheel and deal, schmooze, and flirt" to make sales. The hot dog stand taught him direct sales, which later inspired him to pursue copywriting as a way to sell at scale through writing rather than standing in the heat all day.
Embrace Scrappiness as a Competitive Advantage
The second component Sam identifies is developing tenacity and scrappiness - not by choice, but by necessity. (12:59) When Sam and Shaan compared their offices during their early entrepreneur days, Sam was working from a shared $700 apartment with no door on the bathroom, while Shaan had a 30,000 square foot office with heated floors and a chef. Paradoxically, Sam was building something successful while Shaan was "driving the Titanic into the ground." This scrappy environment forced resourcefulness and creativity that became invaluable assets later in building scalable businesses.
Project Selection Through Process of Elimination
The third critical component is learning proper project selection by systematically eliminating bad business types. (15:46) Sam learned to avoid manual labor businesses (hot dog stand - not scalable), illegal or legally questionable ventures (moonshine sales), and businesses requiring significant upfront capital. His criteria evolved to focus on "forgotten businesses" that serious operators don't take seriously, businesses that can bootstrap to $100 million in revenue over ten years, and opportunities that can't be easily disrupted by AI or technology.
Minimize Risk, Not Maximize Returns
Successful entrepreneurs are actually risk minimizers, not risk takers, according to the discussion about Richard Branson's airline strategy. (22:01) When Branson started Virgin Airlines, he didn't buy planes - he leased them with minimal upfront commitment and presold tickets to cover costs before paying for flights. Similarly, Sam learned to reduce risk through research (talking to bankers, ex-CEOs, employees), bootstrapping instead of taking investment, pre-selling services, and choosing businesses with proven demand in other markets. The goal isn't to take big risks but to eliminate as much risk as possible while still having upside potential.
Focus on Rate of Learning Over Individual Project Success
The key to long-term entrepreneurial success isn't the success of any individual project, but rather your rate of learning and adaptation. (36:18) Sam and Shaan both took approximately ten years to figure out what constituted a good business, emphasizing that this learning process is normal and necessary. Each failed venture provided valuable lessons that compounded over time. The "rule of 100" applies - try 100 times, making each attempt slightly better than the last, and success becomes inevitable through accumulated learning and skill development.
Statistics & Facts
- Sam made his first million at age 31 when his wife's Airbnb stock went public, followed by his company sale three months later in February. (00:29)
- Home Depot hot dog vendors make approximately $100,000 per year according to a video Sam saw, which inspired him to start his hot dog stand business. (03:34)
- Sam's Anti-MBA Book Club attracted 2,100 people to sign up for the email list, with about 20 people showing up consistently each week to discuss business books. (10:11)
