40 Questions To Ask Yourself Before Launching A New Venture

If I were to launch a new venture today, here are the questions I'd absolutely need to answer first:

Personal

• Am I mentally and emotionally ready for what’s coming?
• Do I have the motivation and energy to start from scratch again?
• What’s my true end goal with this venture? Is it purely financial?
• Could I achieve that outcome with less risk or effort?
• How passionate am I about this idea?
• Am I willing to dedicate the next 10 years to this?
• Am I ready to swallow the frog again?
• Are my motivations aligned with the commitment this will require?
• Am I taking the most convenient next step?
• Am I pushing myself out of my comfort zone?
• Does this align with where I want my life to be in 5-10 years?
• What are the top 3 conditions that must be true before I fully commit?

Market & Opportunity

• Can I leverage existing assets, or do I need to start from scratch?
• What’s my distribution advantage?
• What’s my team advantage?
• Do I have a location or regional advantage?
• What’s my unique edge beyond technology?
• Am I entering a blue ocean or a red ocean?
• Is the market size large enough?
• Does being first, second, or third to market matter?
• What gaps exist in the competitive landscape, and how will I exploit them?
• What are the biggest unknowns or risks that could derail this venture?
• What’s my contingency plan if the timing isn’t right?
• Is now the right time to launch, or am I too early/late?
• How can I compress what took me 5 years into 12-18 months?
• Do I have the right founder/market fit?
• Is this a build-to-sell opportunity? If yes, what’s my exit strategy?

Business & Industry

• Am I truly passionate about this industry?
• Do I really want to build a SaaS/marketplace/e-commerce business?
• Do I really want to go B2B/B2C/D2C?
• Where is the industry heading over the next 2-5 years?

Funding & Financials

• Do I want to self-fund this venture?
• How long until I make my first dollar?
• How long until I reach break-even?
• Could this become a $100M/year business? How do I get there?
• Am I prepared to deal with VCs or external investors?
• Who are the right strategic backers for this?
• Do I have the skills and network to hyper-scale this business?
• Am I comfortable with the possibility of walking away with $0?

What do you think? Any other questions I might have missed?