May 16, 2018

What question do you want to see successful founders answer?

I'm thinking about rounding up lots of successful founders and asking them each the same question. For example, "What are your best tips for hiring?", "How did you decide on your pricing?", "How important was your initial idea vs execution?", etc.

The goal is so you guys can easily read through a ton of answers when you're facing that problem yourself. Typical books, interviews, and blog posts aren't bad, but sometimes it's more helpful to read multiple perspectives in quick succession.

What questions do you most want me to ask?

And who should I ask? I typically talk to bootstrapped founders, but there are plenty of other knowledgeable people in the world.


  1. 20

    "How did you find your first users?"

    1. 6

      This is what I always want to know first from successful founders. To expand a little: Tell the story of how you on-boarded your first 10 customers from first reaching out to them to maintaining the relationship once they were hooked into your product.

    2. 1

      Something similar that also talks about what strategies didn’t work or didn’t work as expected i.e What was your marketing strategy for the first 90 days? What worked & what didn’t work?

  2. 14

    “Now that you’re successful, is it obvious why previous ventures failed?”

    1. 2

      I had something along these lines as well. More in the form of 2 questions:

      Q1. How many ideas/businesses did you try before finding success? Can you talk about them?

      Q2. In the current business, did you have to pivot on your initial concept? If so, how big of a pivot was it?

  3. 6

    I'm really excited to see how this works out.

    I don't have a question suggestion* per se. But IMO 'newer' founders face two main kinds of knowledge gap:

    1. They don't know what to prioritise (should I be building a product, building an audience or doing sales right now?)

    2. They are missing practical, actionable skills needed to get things done (for example a 'good enough' landing page, cold email sequence, retargeting, etc).

    Every week a few IHers email me and ask for help/feedback/advice. They tend to ask the kind of questions you gave as an example (or written in the comments so far) but, when you probe a little deeper, they almost invariably need help with one of the two problems I mentioned above. I guess one of the hardest things to work out as a founder is what questions do I need to ask?

    Another thing (which I'm sure you've already though of) is that founders tend to answer more open-ended questions based on their current challenges/priorities.

    For example I've had much more luck asking successful founders "What would you do differently if you had to make your first hire all over again?" than asking "what are your best tips for hiring?"

    *(try saying 'question suggestion' five times fast)

    1. 2

      Good insights! Our approach has generally been to ask an open-ended question, then follow up with bullet points that suggest specific topics readers might be interested in. Tends to work out, but takes a bit of trial-and-error to refine those bullet points.

  4. 6

    The goal is so you guys can easily read through a ton of answers when you're facing that problem yourself. Typical books, interviews, and blog posts aren't bad, but sometimes it's more helpful to read multiple perspectives in quick succession.

    +1

  5. 5

    If you had to start over from scratch today, what would be your first steps and what would you build?

  6. 5

    “How would you go about finding, vetting, and pairing up with a cofounder if you had to start all over with no network?”

  7. 4

    What about doing the same set of questions also to unsuccessful founder, to see if there is any match/mismatch with the successful one?

    1. 1

      Fascinating idea! My guess is answers will be similar (except for the "uh, what do you mean?" replies from noobs.) so comparisons would highlight the role of non-knowledge. i.e. luck, grit, geographic location and of course, market and team.

    2. 1

      I do like asking successful founders about their earlier failure stories. In my experience, you simply learn more from success than from failure, especially when the same person can contrast the two.

      1. 1

        And the reality is, in many cases unless you have had some success, you can’t always identify the failures. Knowing the difference comes from experience... when you stare at the war wounds of what NOT to do, it’s easier once you know the difference n what TO do.

  8. 3

    How do you stay happy and healthy :)

  9. 2

    If they took VC: Why did you decide to pursue this model? What made you want to go big, or scale up, rather than keep it small and just cover your salary?

    1. 1

      I like this. Why did you decide to bootstrap, why did you decide to fundraise, or why did you decide to switch from one approach to the other? Got plenty of companies I could talk to from all three (technically four) groups.

      1. 2

        I sometimes wonder if we are missing some middle ground. Fundraising isn’t always VC or bust. What about the bootstrappers that then do an angel round, especially if that angel funding comes with mentorship and is more ‘smarts’ money where you are getting someone onboard to help you succeed and not running through the VC march?

        A rarely hear on the podcast about angel rounds that lead to a successful exit. It’s usually either bootstrap or VC. Many succcessful exits are done without needing gobs of VC money. Sometimes a “friends & family” round or other angel fund can get you there if you are smart with the money, and have your exit plan. Exit fast and often is what I’ve learned. Easier to say than do though.

      2. 1

        Yeah! I'm mostly interested in hearing what drove that route, and why the founder wanted to go 'big' or not, wanted to exit or so on. I think there's a lot of value there, particularly when you consider that those opinions often aren't immutable and sometimes just completely change.

  10. 2

    "How did you come up with a problem to solve that resulted in a product users actually need and use and that you're passionate about?"

  11. 2

    What would you have done differently when you started, if you knew then what you know now?

  12. 2

    How long did you go without a salary or paying yourself peanuts?

    1. 1

      Assuming they did, since a lof of indie hackers start out part-time as side-projects I believe.

  13. 2

    Great post idea. Some thoughts though: I think advice is very contextual and can be very good, or sometimes bad too.

    I think it would be awesome to ask questions to for example a group of entrepreneurs (example : "SaaS founders" or "Ecommerce entrepreneurs" or "Solo founders" or "Entrepreneurs who have a team of 50+ people")

    The thing I found with advice is that it is very contextual: It can be great to hear and motivating but often it might not apply directly to you and might even sometimes lead to you in the wrong direction whereas if you receive really targeted advice that fits your stage of business / your particular business (with entrepreneurs who've been exactly there before) it can really make a difference.

  14. 1

    "How do you recover from being burned out/overworked? How do you relax?"

  15. 1

    How did you validate your idea?

  16. 1

    What do you do, if anything, to foster the right mindset for success?

  17. 1

    What did your MVP consist of?

  18. 1

    How did you find your market? Did you start with an idea or did you find an audience first?

  19. 1

    Did reading stories from other founders affected the way you made business decisions?

  20. 1

    Ok, maybe some more practical questions:

    What is your target LTV:CAC ratio?

    How many months does it take to recover your CAC?

    What was your MRR Growth Rate in Y1? Y2? Now?

    What is your ARPU/ARPA?

    What is your Net MRR Churn Rate?

    I wish we had this info for every one of the companies you interview. And compare that to industry averages... and get their opinion on how they are doing on each considering their numbers.

  21. 1

    This was something I was trying to ask in another thread (‪https://www.indiehackers.com/forum/suggestions-for-marketing-automation-platforms-like-hubspot-but-for-startups-e0d61ee435‬)...

    What marketing automation platform did you use to manage your digital content delivery? Especially in the Indie Hacker world where trying to keep CAC down is important, signing up for HubSpot or Marketo at the start usually isn’t a good use of early dollars. So what did they do/use in the early days?

    They say that:

    Perfect Marketing - Actual Marketing = Required Sales effort

    Did those successful SaaS businesses see that as true?

  22. 1

    What are the two biggest mistakes you've made that have slowed down your path to success with your business? Why did you think you made these mistakes? What were the results of the mistakes? How did you discover the mistakes? How did you fix them? It would be helpful to read this from any founder, successful or not, bootstrapped or VC-funded.

  23. 1

    "Why did you choose to work on this idea vs ten others?"

  24. 1

    When things looked like they were not going to work out... Why didn't you quit?

  25. 1

    "What books do you wish you had read earlier?"

    This was a question on Hacker news and I'd like to see something like this from founders.

    https://news.ycombinator.com/item?id=14477851

  26. 1

    How did you decide on your name?

  27. 1
    1. Were you fully productive throughout the development?

    2. How often you felt "this is crazy. No one is going to buy this piece of shit I call my glorious product"?

  28. 1

    "How did you build an audience before launching your product?"

    It doesn't matter how good your product is if no one sees it, and I think that is the biggest problem for many people.

  29. 1

    "How often did you feel like everything was too much, the challenges too difficult? How often did you think about quitting?"

  30. 1
    1. "How did you know what to build first?"

    2. "How did you get your first five users?"

    3. "How did you get the twenty next?"

  31. 1

    "When and why did you hire your first employee?"

  32. 1

    What would you do differently if you were to start over tomorrow with nothing but a few bucks(<500) and a laptop?

    No connections, no skills, etc. The only thing you will have from your current 'you' is your knowledge.

  33. 1

    What are your best tips for growth marketing?

  34. 1

    If you had to start over from scratch now on a new business venture, what would be the first three things you would do?

    What would be three surprising things you'd not focus on at all?

  35. 1

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