This thread is pretty good:

Very good questions!

  1. Where are you at right now with your business? What work have you done? What roadblocks are you facing?

  2. Can you summarize the above answer in 1-2 sentences?

  3. Now imagine you’re doing this for a friend you really admire and believe in. Can you make those 1-2 sentences more confident while still being truthful?

  4. Let’s imagine that you’re unable to make money off your business. How much money do you have in months before you run out and can’t support yourself or the business anymore? This is called your “runway,” the monthly amount is your “burn rate.”

  5. If your runway’s low, what will you do to get short term cash? How can you most align that plan with the long term business plan— ie working toward it with paid work, having enough free time?

It’s okay if getting a full time job is the short term plan, the key is having that be part of the strategy and keep moving forward.

  1. Do you have cofounders, or are you thinking of bringing cofounders on? If so, how are you resolving the intense pressure of cofounder relationships? Have you tried working together, seen the person under pressure or angry, do you have a plan for if they leave early/abruptly?

  2. Have you thought about pros/cons of different ways to structure the company?

  3. Have you considered profit sharing, cooperative ownership, other progressive ideas? How are you going to treat employees and partners well, aside from the work they’ll be doing?

  4. Have you spoken to other entrepreneurs, especially people with similar businesses or who are in your industry? Do it. Get advice from them. This is critical. They’re win-win conversations, they help both you and the other person.

  5. If you’re B2B, have you interviewed potential customers? Do it. Those conversations are often more important than development. You need to know you’re building something people not only like but will actually give you money for.

  6. How are you pricing your product or services? How did you come to that price? How are you handling the potential of getting this price wrong?

Is this priced high enough to make a living/company off it? How many customers do you need for that? Do you need a short term pricing plan? How will you transition into the long term one?

  1. How possible is it to build your company yourself, how long can you go alone? What would you do if it was only you? If you have cofounders you know you trust, what are the answers for your small core group?

  2. If you need others’ work to get this off the ground, what’s the budget for that? How can you treat them well, balancing early stage budget with potential to make a lot from the work?

  3. How will you introduce yourself to others? Work on making it an intro that counters bias and is confident. What’s your product pitch? Keep in mind pitching is HARD. Work at it.

  4. What’s your online presence like? Imagine people only have 6 seconds of looking at your website, social media account, etc before they decide if they’d want to work with you or buy your product. How can this be better?

  5. So what’s your business plan for the next month? Next 3 months? What will you do next week to take a step toward this?

  6. Now go back to #3. Do that exercise one more time and remember you can do this. Work on your plan.

I don’t ask these questions because I think they haven’t thought about all this. Sometimes that’s true, but mostly it helps to declutter the mind, lay it all out, structure these thoughts, take time to reflect & plan, while staying positive & realistic & confident.


Good things for even later-stage companies too and even for more experienced entrepreneurs and business leaders. I mean, shit… even as I walk through the questions I can’t help but think through the answers and how well we’re doing with our project.

Hits hard; that’s good.


Also published on Medium.