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If you really care enough about this to understand the background, check out the old Stackoverflow podcasts: https://stackoverflow.fogbugz.com/?W4

(They have decent transcripts there)

Jeff & Joel talk about the concept of what makes a good question a few times -- the way they got to there is interesting and worth listening too. Actually, the whole series of podcasts is an interesting view into the thoughts of founders starting a company.



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Good list — not that these are earth-shattering insights, but it's useful to get confirmation that these are appropriate questions to ask. In addition to getting the answers, asking these questions will also help a founder think about potential issues that could come up (e.g., timing, process, lead/follow). I imagine that asking these questions also makes a founder look a bit more sophisticated.

Although I pretty much never listen to podcasts, I actually listened all the way through. Would be great to have a written list also! (edit: thanks to fellow commenter for posting the list)


Preview: "When we started interviewing startup founders, we didn’t plan on building a big podcast, it was simply the best way to get audio content in the hands of listeners.

But the actions we took from that initial decision forward made it extremely easy to stick with the project as it grew, without losing interest and letting it fizzle..."


NPR has a podcasts that interviews founders and how they got started, how they made money (likely they didn't, at first) and how they continue to be better than everyone else. It's called How I Built This.

https://www.npr.org/podcasts/510313/how-i-built-this


I'm interviewing 33 startups and they talk about how they got interested in entrepreneurship, ways they dealt with challenges such as finding cofounders, hiring, raising money, staying motivated, getting users, etc. It's the same Q&A approach as Founders at Work, but all of these guys are still in their early stages (although there are a few like Foursquare and GitHub that aren't as early stage).

I think the thing I'm looking for is relatability. There are many podcasts that idolize startups and founder life. The Dating Ring's podcast did the opposite and showed vulnerability. To me, that's why it was an interesting learning experience.

But to be specific - I think that small companies in make-or-break times would be most interesting. Also, everything looks easier in retrospect, but understanding the thought process and how they are balancing different options would be interesting to me.


I remember listening to you guys talk about your experience starting the company on a podcast (I think it was Startup from Gimlet media?). It was an awesome episode (I think two actually) and was very inspirational to listen to. I love the part when you guys received the money during one of the founders' wedding and seeing the number on the bank account.

I'd like to hear from Founders who have very interesting stories and journeys to share. I do not care if their products got traction,flopped or big hit. All I want to get is how can we as listeners can learn from their success or failures. Thanks for doing this.

One of the founders gave an amazing talk at Stanford's Entrepreneurial Thought Leaders series:

http://ecorner.stanford.edu/authorMaterialInfo.html?mid=3432

Worth listening to if you are interested in starting a company.


Agreed. I would like to see deeper questions. I suffered through the "struggle" that Ben Horowitz talks about. I would ask questions like:

Do you wonder why you started the startup in the first place? Do you regret it? Do you believe you should be the founder of your own company?

Just some food for thought.


This is really solid advice when looking at it backwards too--if you, as a founder, cannot produce reasonable and compelling answers to these questions, you don't know what you're doing, where you're going, or how to actually get there.

Great read.


It's hard to get feedback on podcasts!

This interview show features CEO/Founders of startups like Zapier (YC S12), WayUp (YC W15), Drift, and RadPad. The title is quite literal, the format of the show is intro -> company mission -> company values.

For founders: you learn about other company cultures and hear leadership/management advice about lessons learned and ideas you can try out.

For employees: you can see what it's like to work inside these startups, or compare/contrast to your current work culture.

Hit me with some feedback! I've found it helps if you mention other podcasts you like for reference (to compare production quality, format/structure/length, etc.)


I'm not sure if you have, but I'd suggest listening to Pieter Levels and Courtland Allen on youtube. They each have several talks where they discuss this sort of thing. Pieter Levels actually walks through his process of identifying problems and building them into potential startups within a month timeframe. Courtland has a Micro Conf talk where he discusses the various stages of building startups.

Also, a great resource to learn how other people literally went from ideo to customer to profitable startup is the Indiehacker podcast. The first 200ish episodes are all interviews off this exact thing, plus IndieHackers has about 400+ written interviews of profitable startups by the founders that touch on this in many cases (IndieHackers is run by Courtland Allen)


I found these questions to be pretty interesting

https://medium.com/@therealpankaj/interview-questions-to-ask...


Yep, you are totally right. We did lean to building a lot in the past, and I believe we still do even though we try to do our best not to.

That's why I am doing this Ask HN and it's extremely valuable.

I also want to figure out who to talk with next so I can understand their problems. I am thinking talking to companies and startups in general about their problems and challenges might be beneficial too. Might start podcast series about that.

Thanks!


So far (11 mins in) this feels like a 50 minute podcast recapping the book. I'm definitely enjoying Jessica's presentation and I imagine this will be very useful for anyone who's on the fence about buying the book itself. [1]

I'm actually reading it right now and it's kinda neat reading the ca. 2006 viewpoints of serial entrepreneurs who have been hugely successful (again) since these interviews were recorded.

Imagine what Evan Williams (Blogger/Twitter) and Paul Buchheit (GMail/Friendfeed) would have wanted to talk about three or four years ago. You can see the seeds of their soon to be successful new businesses in every line of these two interviews. Really a great bit of history.

EDIT: 21 minutes in the topic shifts to "What can big companies learn from startups?"

[1] http://www.foundersatwork.com/


I like reading articles about Founders of companies sharing their ideas, experiences, achievements and what it takes to start a company, because a lot goes into building a tech company from scratch. Such interview articles give you a candid overview of their journey and give you insights for improvements by learning from their mistakes.

I came across this article where the Co-Founders, the CEO and CTO talk about their experience. Thought i’d share it with everyone as well.


Really interesting talk. Thank you for sharing.

In my opinion, the best bits were those which focused on the learnings and lessons of the experience. While the startup narrative was interesting, I would have loved to have gone deeper into the conclusions of Chris and the rest in retrospect.


I recently started a podcast on Spotify and Apple called the Technical Founder (https://www.the-tf.com/), where I chat with other engineering founders and explore the technical challenges inside growing startups. Together we unpack the tactics and strategies being used to build modern solutions.

I am looking for feedback from founders and potential founders on how to get the most value from these chats. Specifically I would love to know:

- What issues are top of mind for you as a technical founder? Fundraising? Stack selection? CI/CD tooling? Hiring? - If you listen to an episode, do you listen to the full thing? If not, where did you drop off? - If you enjoyed an episode, what stood out to you? What would you want more of?

I’m always looking for potential candidates for the podcast, so if you have a great founder in mind (including yourself) please let me know!

Thanks so much,

Ryan


Oh absolutely believe that asking yourself these questions is critical. Even if the answers aren't encouraging or positive. In the very least, they make you think about how you might overcome these challenges if they exist for your business.

Didn't mean to dunk on your post. I actually loved it. Just wanted to call out that founders should probably not follow the letter of the law of the formula but more use it as a guide to evaluate ideas and problems.

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