What info do you want to know from every IH podcast guest?

I sense a bit of Tim Ferriss in your example questions and that's not a bad thing - I think they're all great Qs.

I'd also love to hear stories around the moment when the product "clicked" and started taking off. What caused that? Did the founder manage to find a customer channel that was spot on? Did an unlikely connection help out in some way? How did they make their own luck?

I think a lot of great success stories have a bunch of serendipitous moments and I love hearing about them.

Would love to learn some tips on how they managed their time and prioritized product features. Esp. for the solo founders.

What's one thing you wish you learned sooner?

1. How did you get your first 10-100 customers?
2. If somebody launched a copycat and is serious about it, how would you compete?

First, I think you're a great interviewer. Honestly, you ask really good follow up questions and that's key. Some ideas:

-Was there ever a time when you felt like giving up (on your business, product, etc.) ? If so, tell me about it and what got you through it?

-Do you still battle with impostor syndrome? And if so, how do you fight against it?

-What was the specific time when you thought, 'I made it. This is going to work.' Take us back to that moment and describe it.

Thanks for all you do.

What were the biggest inflection points in your life?

Draws out struggles and stories

Few ideas:

1. What led them to where they're today/to what they're doing today.
2. Did they have ideas they decided not to pursue, if so why.
3. What's their relative advantage with the product/niche they're working on?
4. How do you know if an idea you have doesn't fit you/you shouldn't pursue it?

I think it would be interesting to hear more on what not to do. Something like:

• What are some of the most impactful learnings you got from your failures?
• What markets would you avoid and why?
• What were your signals to start pivoting, moving to next idea?
• What are the most common mistakes you see solo founders make?

These are all great questions. What I am also looking to know is : when your side hustle is also your passion/hobby, how do you force yourself to concentrate on the parts you don't like ?
For example, when you are a developer building an app, you can obsess over the implementation details because you get great joy from it and it can be hard to focus on just shipping what is needed and concentrate on the business aspect.
Hope my question is clear enough.
Thanks !

Marketing numbers. How many articles did you write, ad spend, social media posts, number of cold calls, emails sent, customer conversations before you started making sales? Both raw counts and ongoing frequency. Which channels worked best vs worst, and empirically how much work goes into the channels that work.

So often you hear "talk to your customers" but what does that actually mean? Narrate an example exchange as if the person you're explaining this to is a socially awkward robot (because we are). Specifically how do you pick customers and potential customers to talk to?

How many times have you built something that failed completely? What stage did those projects get to on average? Why didn't they work out?

I loved it on the Tringas / Jackson interview when they talked about X fails before one success because it was a surprisingly high ratio.

Your podcast is up there with EconTalk for very high quality content already, so don't change too much! :D

How do they choose a category to build an innovative product? Is it a random decision or money-driven or higher purpose-driven? How do they know at the beginning that a given category will sustain their motivation for years or decades to come like in the case of Basecamp (I just listened to the interview on IH Podcast with Jason Fried)?

I'm sort of already doing that with a tool I created https://podbytes.co/video/ckaoncevx0n5w0165b5xqz4q6. I am wondering if podcasters would find a Playlist as a service. Where you get a summary and the best parts of each video.

One question I have always wanted to ask guests who build an audience is...

On the day they started - did they begin building an audience/product with:
A) their brand name (and stayed anonymous)
B) or did they start actively writing using their personal social identity

I know folks sometimes have dozens a products / hacks before something takes off. So this question is about using your social klout before you are on to something - or do you invest/commit with your personal brand as soon as you have the idea and begin marketing.

i think this is equally relevant after you are successful. can you now start a new project with your name or do you experiment with a new project and want to be thoughtful of where they point their audience and hence start with a domain/landing/product separately.

What is something you are actively trying to get better at doing?

What's the best way to reach them?

I'd love to know what authors / influencers / celebs / mentors etc. they follow to help them learn.

What their daily life look and how they manage time

What is the hardest part of your business?

I would like to know more about the Pain Points. What I mean:

• How many ideas did you have before to make this idea work?
• What was the worst time you had to go through as a founder?
• What was the most complicated problem you had? Did you solve it?
• What about work life balance?
• What has prevented you the most from achieving your goal?

• What counter-intuitive advice had a big impact on your life or business?
• Who do you learn from and get inspiration?
• What’s the most underrated and overrated aspect of making a successful company?
• How do you try to become a better person by one step every day?

One of the unique things I feel is how often people share revenue numbers. Hearing founders explain how they went from zero to x to where they are now is always super is insightful in terms of growing a business.

What time-frames do you think in, in different contexts?

e.g.

• for a marketing experiment, what's the right amount of time?
• for your 1st/10th/100th customer, what's enough time to acquire?
• for a feature, what amount of time is acceptable to build it?
• for gauging success/failure of the project, what's enough time?

I feel this has changed the most for me. I'm much more patient than I used to be, but I'm not sure if that should be true in all contexts.

• Tell a story about a business or career decision you made that you now regret.
• Who is a maker or entrepreneur you admire?
• What's one product you love that you wish you created?

• what keeps you awake at night?
• Knowing what you know now, if you could give your early maker self one piece of advice, what would it be?
• Does “making it” feel as good as they had hoped/dreamt when starting out?

These questions are all great! I would love to come on the show in the near future.

What was the biggest mistake/failure/set-back you've had in your journey and what were the learnings gleaned from it.