Topline The Fastest Way to Make $1M in 2025 is Not What You Think
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Oct 12, 2025 Three successful entrepreneurs reveal their unconventional strategies for making a million dollars in 2025. They delve into the nuances of bootstrapping versus venture capital, and share insights on the dangers of mislabeling businesses. A discussion on NVIDIA's massive investment in OpenAI sparks debate over whether it's a bubble or a sound infrastructure bet. The conversation also explores the challenges of going public and staying true to one's business model amidst changing market dynamics. Finally, personal strengths of founders are examined, highlighting how passion can sometimes turn into a weakness.
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When To Bootstrap Versus Raise
- Bootstrapping suitability is driven by market dynamics, conviction, and whether venture timelines fit your business.
- Preserve control if you prefer slower, durable growth over venture time-pressure.
Avoid Venture For Craft Businesses
- Avoid raising venture for craft businesses with non-recurring revenue and trust-based relationships.
- Choose bootstrapping when capital can't realistically speed growth without harming the business.
Outreach Secondary At Bubble Peak
- Sam bought large private shares in Outreach at a $4B peak valuation and tracked it in his personal spreadsheet.
- He later discovered Outreach had raised about $800M, changing his expectation of personal returns.
