"Would you rather" questions can spark insights for entrepreneurs. Here are 10 key areas with thought-provoking questions:
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1. Mindset and Vision
- Growth vs. Comfort: Rapid growth with challenges or stable with limited potential?
- Innovation or Tradition: Disrupt an industry or perfect an existing model?
- Passion vs. Profit: Run a passion project with modest returns or a highly profitable venture you’re not excited about?
- Solo Journey or Team Effort: Build alone with full control or share ownership with co-founders?
- Short-term Gains or Long-term Vision: Focus on quick wins or invest in delayed rewards?
These questions reveal priorities and shape strategy. There’s no universal right answer – the best choice depends on your goals and risk tolerance.
"When you start, you just do it. You are naive because you haven’t made your mistakes yet. Then you learn about all the things that can go wrong."
This quote highlights the evolution of an entrepreneur’s mindset over time.
2. Financial Decisions
- Bootstrap or Seek Funding: Self-fund entirely or pursue external investment?
- Debt or Equity: Take on debt to maintain ownership or give up equity for capital?
- High Burn Rate or Slow Growth: Spend aggressively to capture market share or grow slowly and lean?
- Reinvest Profits or Take Dividends: Plow everything back into growth or pay yourself and investors?
- Fixed Costs or Variable Expenses: Mostly fixed costs for predictability or variable expenses for flexibility?
These choices shape a startup’s trajectory. Mailchimp bootstrapped to $12 billion, while Uber raised over $24 billion to fuel rapid expansion.
"Cash flow is the blood that keeps a business alive. Managing it well can mean the difference between thriving and barely surviving." – Dave Lavinsky
Carefully weigh short-term and long-term implications of financial decisions.
3. Product and Market
- Niche Focus or Mass Appeal: Create for a specific niche or aim for broad appeal?
- First-to-Market or Market Follower: Introduce a new category or improve existing solutions?
- B2B or B2C: Target businesses or individual consumers?
- Local or Global: Start local or immediately pursue global expansion?
- Freemium or Paid-Only: Offer a free version with upgrades or stick to paid-only?
Spotify‘s focus on legal streaming led to 182 million paid subscribers. Uber’s free rides initially solved taxi system problems.
"If prospects are not willing to pay for your product, it means there’s no market for it." – Marc Andreessen
Consider long-term vision, resources, and audience needs when making product and market decisions.
4. Team and Hiring
- Hire for culture or skills: Perfect culture fit lacking skills or highly skilled candidate misaligned with culture?
- Generalists or specialists: Versatile team handling multiple tasks or specialists excelling in specific areas?
- Remote or in-office: Fully remote with global talent or in-office for better collaboration?
- Experience or potential: Proven professionals or young talents with high potential?
- Slow growth or fast scaling: Grow team steadily or scale quickly for market demands?
Slack‘s decision to outsource beta design led to $250 million investment and 15,000 users in two weeks. Building in-house allows more control.
Hiring mistakes can cost up to 30% of an employee’s salary. Use specific interview questions to gauge fit:
- "Describe a time you completed a project without clear instructions. What was the result?"
- "Tell me about a time you took initiative to solve a long-standing problem at work."
Consider your startup’s needs, budget, and goals when making hiring decisions.
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5. Work-Life Balance
- Work hours or flexible schedule: Set hours with clear boundaries or blend work and personal time?
- Office or home: Dedicated office space or work from home?
- Constant connectivity or unplugged time: Always connected or designated offline periods?
- High-stress, high-reward or low-stress, steady growth: Intense pace with big potential or steady, modest growth?
- Travel for work or stay local: Frequent business travel or focus on local markets?
Arianna Huffington’s collapse from exhaustion led her to start Thrive Global, focusing on well-being.
"Burnout gets sustained through shame and not sharing the challenges you’re facing." – Kari Sulenes
To avoid burnout:
- Take regular breaks
- Set clear boundaries
- Delegate tasks
- Prioritize self-care
63% of business owners report experiencing burnout. Use "Would You Rather" questions for team building and self-reflection.
6. Risk and Opportunity
- Bootstrapping or investor funding: Self-fund with full control or seek investment for faster growth?
- Niche market or broad appeal: Target specific niche or aim for larger market?
- First-mover or fast-follower: Enter new market first or learn from others’ mistakes?
- High-risk, high-reward or steady growth: Pursue game-changing idea or focus on stable model?
- Pivot or persevere: Change course when challenged or stick to original plan?
Jim Triandiflou sold equity to VC, boosting Ockham’s value. John Gabbert refused funding to keep control of Room & Board.
"Progress always involves risks. You can’t steal second base and keep your foot on first." – Frederick Wilcox
Consider both benefits and drawbacks when weighing risk-opportunity trade-offs.
7. Innovation and Technology
- AI or human expertise: Invest in AI automation or focus on human experts?
- Cutting-edge or proven tech: Adopt latest, untested tech or stick with reliable solutions?
- In-house development or outsourcing: Build tech stack internally or partner with vendors?
- Open-source or proprietary software: Use open-source to save costs or invest in proprietary for control?
- Cloud-based or on-premises: Move all to cloud or maintain on-site infrastructure?
Meta faced backlash for AI-powered search, while Toyota‘s lean manufacturing principles led to efficiency.
"Humans + Software > Humans or Software." – Robbie Allen
Consider both short-term gains and long-term impacts when making tech decisions.
8. Ethics and Social Responsibility
- Profit vs. Purpose: Maximize profits or prioritize social impact?
- Transparency or Privacy: Disclose all company info or maintain strict confidentiality?
- Local vs. Global Impact: Invest in local projects or tackle global issues?
- Short-term vs. Long-term: Pursue quick wins or focus on sustainable practices?
- Employee Benefits or Customer Prices: Offer extensive benefits or keep prices low?
Patagonia‘s founder gave away the company to fight climate change. 90% of employees at socially responsible companies feel more inspired and loyal.
"Ignoring ethics will always come back to bite you, no matter how far ahead you get." – Elle Kaplan
Consider both short-term gains and long-term impacts when making ethical decisions.
9. Growth and Scaling
- Profit now or growth later?: Focus on immediate profitability or prioritize rapid growth?
- Organic growth or acquisitions?: Grow slowly through organic means or expand quickly via acquisitions?
- Bootstrapping or external funding?: Maintain full control or accelerate growth with reduced ownership?
- Niche market or mass appeal?: Dominate a specific niche or aim for broader market?
- Vertical or horizontal expansion?: Deepen offerings in current market or expand into new, related markets?
Mailchimp bootstrapped to a $12 billion acquisition, while Uber pursued rapid growth at the expense of profitability.
"You can focus on things that are barriers or you can focus on scaling the wall or redefining the problem." – Tim Cook
Consider both personal goals and market realities when choosing growth strategies.
10. Exit Strategies
- IPO or acquisition?: Go public or sell to a larger company?
- Family succession or external sale?: Pass down to family or sell to outside party?
- Quick exit or long-term growth?: Aim for fast exit or build for decades of success?
- Full sale or partial exit?: Sell entire stake or retain partial ownership?
- Cash out or stock options?: Receive all-cash payment or accept stock in acquiring company?
Mailchimp chose acquisition over IPO, while REI operates under an employee stock ownership plan.
Only about 15% of sustainable startups achieve a successful exit valued at $50 million or more.
"Every entrepreneur should have an exit strategy." – Lien
Align your exit strategy with personal and business goals for maximum impact.
Use these questions to gain insights, stimulate thinking, and improve decision-making. Regular self-reflection using techniques like G.L.A.D.D. can reduce stress and build confidence. Make "Would you rather" questions part of your toolkit for navigating the challenges of entrepreneurship.