10 Questions to Ask Before Starting a Business
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Hello Future Leaders and Entrepreneurs!
You're at a crossroads. The 9-to-5 feels safe, but the dream of building something of your own has been pounding your brain for days, weeks, and even months. I know this exact feeling when I made the decision to start 787 Coffee. The calling became an obsession, but before you make the leap, you need to go beyond the business plan.
This is a moment for soul-searching and a cold, hard look at what it takes. Most startups fail because they're not clear. The antidote is not to work harder, but to ask better questions. Here are the 10 most critical questions to answer to build a business that doesn't just survive but thrives, rooted in the wisdom of top founders and CEOs.
-Let’s do this.
1) What painful problem am I solving?
Why it matters: This is the most important question you will ever ask. Without a "definite" solution for a specific customers needs, none of the marketing, funding, and dream team, can save your business.
Think about Elon Musk's ventures. He didn't start with a goal to "build rockets" or "make electric cars." He started by identifying fundamental problems. For Tesla, the problem was that electric cars were slow, ugly, and had limited range. His first solution wasn't a mass-market sedan, but a high-performance sports car. A solution for a niche group of wealthy early adopters who desperately wanted a beautiful, fast car that happened to be electric. He solved a real, painful problem for a very specific customer.
Exercises:
List at least three specific customer needs. For each, write down the top three pains they face and their current workarounds.
Conduct 10-20 problem interviews. This is a conversation, not a pitch. Your goal is to listen, not talk, and uncover your target customer's frustrations.
Quantify & Commit:
Ensure at least 70% of interviewees rate the pain you're solving as an 8/10 or higher.
Secure 5+ letters of intent or paid preorders before you write a single line of code or create a product. This proves market need.
2) Why me, and why now?
Why it matters: Investors and early hires don’t just back an idea; they back a founder with a unique edge. Think of Sara Blakely, the founder of Spanx. She didn’t have a background in fashion, but she had a personal, painful problem she was uniquely obsessed with solving: finding comfortable and flattering shapewear. Her "why me" was her lived experience, and her "why now" was her realization that no one had truly solved this problem for women in an authentic way. This is your unfair advantage. You need to launch your business when a big trend, like a shift in technology, laws, or culture, is pushing you forward.
Exercises:
Tell your personal story. On a single page, write about a problem you've faced that gives you a unique advantage. This can be your experience, your network, or a specific expertise.
List two big trends in technology, regulation, or culture that make this the perfect time to start your business.
Quantify & Commit:
List at least three specific examples of your unique edge (e.g., 10 warm introductions to ideal customers, a prior win in the same domain, or a relevant patent).
Prove the timing is right with at least two trends backed by data or news articles.
3) What is the smallest test I can run in 2-4 weeks?
Why it matters: Minimum Viable Products are about reducing waste and uncovering the truth quickly. Before you spend months or thousands of dollars building a full product, you must prove that your customers will engage. For example, when Drew Houston created Dropbox, he didn't build his full service. He made a simple video demo. The video showed how the product would work and went viral, generating thousands of sign-ups. This proved there was a market need before he wrote a single line of code.
Exercises:
Choose one simple test: a landing-page "smoke test" to gauge interest, be in the frontlines and serve your first customers, or a simple prototype demo.
Pre-define your success metrics before you ever launch.
Quantify & Commit:
Achieve a traffic-to-signup rate of at least 5% on your landing page.
Secure at least 10 paid pilot commitments.
Commit to running at least three build-measure-learn cycles and tweak your product in your first 30 days.
4) What will I measure?
Why it matters: You can’t rely on a feeling. The feeling of "pull" or "viral growth" is a result of a strong signal, and you need to know what that signal is. A consistent metric is your North Star. Jeff Bezos, the founder of Amazon, famously focused on one mission: customer obsession. He measured success not by gut feeling, but by relentlessly focusing on customer data and retention. He knew that if he could deliver an exceptional customer experience, all the other metrics would follow.
Exercises:
Run a survey asking your most engaged users, "How would you feel if you could no longer use our product?" A high number of "very disappointed" responses, combined with good retention data, confirms your MVP is a hit.
Pair the survey with weekly retention data and active use metrics.
Quantify & Commit:
Survey Goal: At least 40% of your most engaged users say they would be "very disappointed" if they could no longer use your product.
Usage Goal: Define a clear target for how often your users are actively using the product each week. For instance, your users perform at least three meaningful actions per week.
5) Will My Business Model Work in the Long Run?
Why it matters: This question forces you to confront the financial viability of your company before you run out of money. You need to prove that your business is a self-sustaining machine, where the money you make from a customer over their lifetime (LTV) is more than what it costs you to acquire them (CAC).
A great example is Netflix. Reed Hastings correctly predicted that a subscription model would generate a higher LTVfrom loyal subscribers over time, a stark contrast to Blockbuster's per-rental approach which focused on short-term revenue.
Exercises
Calculate LTV and CAC: Use your gross margin and customer retention data to estimate your LTV. For CAC, use data from actual marketing tests, not guesswork.
Model Pricing: Analyze how three different pricing strategies would affect your CAC payback period, which is the time it takes to recoup the cost of acquiring a customer.
Quantify & Commit
LTV:CAC Ratio: Aim for a ratio of at least 3:1. This means for every dollar you spend to acquire a customer, you should earn at least three dollars in return.
CAC Payback Period: In the early stages, aim to recover your customer acquisition costs within 12 to 18 months.
6) How do I spread the word?
Why it matters: You can have the best product in the world, but if you don’t have a clear, repeatable way to get it into people’s hands, you will not survive. Spreading yourself too thin across multiple channels kills momentum. Mark Zuckerberg famously mastered one channel with Facebook: the college campus. By focusing exclusively on Harvard students, he created a network effect that made the platform an instant phenomenon before it ever reached the broader public.
Exercises:
Pick one primary channel to master: outbound sales, partnerships, content/SEO, paid performance, or product-led growth.
Map your funnel using Pirate Metrics (AARRR): Acquisition source, Activation action, Retention habit, Referral loop, and Revenue trigger.
Quantify & Commit:
Define a channel-specific CAC.
Hit an activation rate of at least 20% for new signups before you even consider scaling your marketing spend.
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7) How do I Transition To Full Time Business?
Why it matters: Before you quit your job, you need to know your burn rate and the specific milestones that will allow you to extend your runway or raise money. This question forces you to face the financial reality of your dream. Think of how the Collison brothers, founders of Stripe, famously lived on a shoestring budget, proving their model's worth before seeking major funding.
Exercises:
Calculate your gross and net burn rates and translate them into a clear number of months of runway.
Set your next funding or traction milestone (e.g., "$X in Monthly Recurring Revenue," "Y number of paying pilots," "PMF score of 40%").
Quantify & Commit:
Maintain at least 12 months of personal and business runway or have a clear milestone that will allow you to extend or raise.
8) Who will I build with?
Why it matters: Team issues and misaligned equity splits are a primary reason for startup failure. You are not just building a product; you are building a relationship. The partnership between Steve Jobs and Steve Wozniak at Apple is a classic example of this. They had completely different skills. Jobs the visionary and Wozniak the engineer, but their complementary strengths and clear roles allowed them to create something magical.
Exercises:
Draft a founder pact that outlines clear roles, decision-making rights, shared values, and a process for resolving conflict.
Implement 4-year vesting with a 1-year cliff for all founders.
Quantify & Commit:
Establish a weekly leadership cadence that includes a written memo and a review of key metrics.
Formally revisit equity and role alignment at 90 days.
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9) What are the risk?
Why it matters: Every great idea has landmines. MVP testing is about defusing them before you spend years of your life and your entire savings. This is about being proactive, not reactive. Steve Blank, the "Godfather of Lean Startup," famously advised founders to "get out of the building" and test their riskiest assumptions on customers. You can't just hope your ideas work; you have to prove them with small, cheap experiments.
Exercises:
List your top five "RATs" (Riskiest Assumption Tests). These could be about demand, willingness to pay, acquisition costs, or delivery logistics.
Design a simple experiment for each assumption with a clear "kill or continue" threshold.
Quantify & Commit:
Run one RAT per week for five weeks.
Commit to killing any idea that fails your pre-declared threshold at least twice in a row.
10) Am I personally ready for the trade-offs?
Why it matters: This is the most honest question you can ask yourself. Entrepreneurship taxes your time, money, and identity. It is not for everyone, and that's okay. You must decide intentionally if you have the emotional and mental resilience to weather the storms. Every successful founder has spoken about the immense personal cost of their journey. They didn't just ask if their business was viable; they asked if they were.
Exercises:
Audit your calendar. Can you realistically free up 10-15 hours per week for at least six weeks to ship your MVP?
Create a personal runway plan, including savings, side income, or a part-time path.
Quantify & Commit:
Set a clear go/no-go date (e.g., 90 days from now) tied to hitting three concrete milestones (e.g., 20 problem interviews, MVP shipped, 5 paying customers).
Share your go/no-go date with a trusted mentor or accountability partner.
It Starts With YOU.
You don't need all the answers to start, but you must have the courage to ask the right questions. The world is full of brilliant ideas, but only a few become sustainable businesses. The difference is not talent; it’s the discipline to confront reality, the empathy to listen, and the integrity to build. By answering these questions honestly, you're not just preparing to launch a business, you're preparing to launch your legacy.
-Thank you for Reading!
Let's get to work. 💯
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How to Apply These Lessons in 3 Easy Steps
As a student or starting entrepreneur, you are both the marketer and the saleshuman. Your first goal isn't just to sell a product. It's to sell yourself, your ideas, and your brand. Here's how to apply the principles of the 10 questions to build a foundation for lasting success.
Step 1: Validate Your Idea, Don't Just Build It
The most critical first step is to prove your idea has a market. Instead of spending months building, focus on testing your riskiest assumptions. Conduct problem interviews to find a genuine pain point for a specific customer. Then, use a simple test like a landing page or a video to see if people will commit before you ever start building. For example, if you're building a new app, your first goal isn't to launch a fully working product. It's to get at least 10 paying customers for a simple demo or manual "concierge" service.
Step 2: Build Your Business Plan, Then Your Business
Once you know what to build, you need a realistic plan for how it will grow. Your second step is to prove the business model can work. Start by defining your unit economics to ensure you'll make more from each customer than it costs to get them. Choose a single go-to-market channel to master first, and draft a founder pact that outlines clear roles and expectations. For instance, before you raise a single dollar, you need a clear cash runway and a milestone that proves you're ready to grow.
Step 3: Prove You're Personally Ready
Your business won't succeed if you aren't ready for the journey. The final step is a personal commitment. You must honestly audit your own schedule and finances to ensure you can make the necessary trade-offs. You need a personal runway plan and an emotional readiness to face the hard days ahead. For example, set a "go/no-go" date and share it with a mentor. This will force you to hit key milestones in a set amount of time, proving to yourself that you are personally ready to make the leap.
Let's simplify the concepts using an example that has lasted for centuries.
Santa Claus started his yearly delivery from the North Pole, creating a simple list to determine which children were good and which were bad by focusing on one core behavior: kindness (Step 1). He decided that his core metric would be whether a child had performed at least one kind act for someone else (Step 2). He began using his personal network of elves to gather this information, which generated the first entries on his list (Step 3 & 4). After sorting the list, he packaged each gift in a simple, hand-decorated box with a personalized tag (Step 5), and used the good cheer and smiles he received as "profit" to add a new tradition—stockings and candy canes—the following year (Step 6). Today, Santa is living proof that following these six steps works, and his brand is still the strongest in the world.