I'm Rob Fitzpatrick. I wrote The Mom Test book, went through YC (s07), learned how to do sales as a techie, and live off full passive income. AMA!

I think of it like figuring out an birthday present to buy for someone. There's no real step-by-step process or questionairre for finding the prefect gift, but the better you know them, the more likely you are to spot an unexpected opportunity to delight them and improve their life.

But to be slightly less cryptic, I'd be asking lots of "show me how/why you do it that way" questions such as:

• Can you walk me through how you do that?
• Why do you do it that way?
• How else have you tried to do it which didn't work so well?
• What's the most frustrating/expensive/risky/fun part? (this one is fairly biasing and can prompt them to mention "problems" that they don't care enough about to fix, so take the answer with a grain of salt)
• Have you tried stuff to deal with those bits? Why or why not?"

I kind of like PG's advice on finding startup ideas[1]. He puts it more eloquently, but the gist is that if you go live your life while getting yourself into interesting situations, and make a habit of trying to understand the people/industries/technology that you're encountering, then those life experiences will start magically transmuting themselves into strong startup ideas. And as a perk, these sorts of "natural" ideas have far less competition since they arise from your unique experiences and place in the world.

[1] http://paulgraham.com/startupideas.html

I've honestly never been able to learn successfully from anything other than face-to-face conversations, and I don't do any emails for learning (or even calls). If it's a simple enough question it could be asked via email, then the answer probably already exists on Google and I can just research it. The bigh insights about goals and worldviews and frustrations is really hard to learn without being in the same room as someone.

Although I'm pretty bad at email, so you may be able to figure out a way to do it better than me. Joel Gascoigne of Buffer apparently did all his validation remotely, using emails to figure out who was most excited and then transition them into Skype calls to chat about the problem. And Cindy Alvarez uses lots of Skype calls and remote interviews. They may have some more useful tips if there's some reason you can't reach folks face-to-face.

I recently finished one about teaching and workshop design, called The Workshop Survival Guide: How to design and teach workshops that work every time[1]. It took ages to write and refine since I care a lot about teaching and didn't want to give bad advice, but I'm super proud of the result and people seem to be liking it.

I'm currently writing one about using applying a product design mentality to create non-fiction books which solve a sharp problem and grow through word of mouth.

I've also got seven other manuscripts at various stages of drafting and editing, but they're each a bit tricky for one reason or another, so I've got no immediate plans for them. The one which I care enough about to find some way to finish is about helping young people understand the career path and options of entrepreneurship, so they can make an informed decision about whether or not startups are right for them, and also which type of entrepreneurship is the best fit for their personality and goals.

[1] http://workshopsurvival.com

Back when I was doing The Bootstrap Challenge, I think I had fallen into some sort of "idea nihilism" where I reasoned that since you can't predict success, that you can't predict anything. This was obviously wrong thinking on my part, since there are loads of things you can predict about any given idea. (Such as how many customers are required in order to pay your bills, how long the product will take to build before people start paying you, and how many employees or hours you'll need to put toward support and maintenance once it's working.)

So I was being extremely self-indulgent with idea selection because I truly believed (at the time) that idea selection didn't matter. I thought all that mattered was how you navigated through the maze.

I also didn't really mind failing at the challenge. (Which is a bit weird to say even if true) I had just come out of a really miserable freelance/consulting project and largely just wanted to purify my soul by getting back into building stuff for myself. And I felt pretty confident that I could quickly earn more money (due to both the audience being gained from the challenge and also pre-existing consulting/freelancing contacts), so I had a pretty good safety net in terms of options, if not actual money.

It can be hard to stick to your personal values when everyone else is shouting about scale, but I think it leads to a much happier life if you can manage to tune that out and focus on the sort of thing that works for you. I wish you luck on the upcoming projects!

Every idea gets hard at some point, so I think it's important to have at least one part of the idea which you really love. That could be the customer you're serving, the problem you're solving, the team you're building, the way you're working, the technology you're using... whatever. But something to sustain you when the going gets tough.

Personally, I tend to lean toward some combination of profitable, easy, and fun. And I really hate losing control of my own time, so I tend to pick things that I can take some time away from without everything catching on fire. (So something like a cafe where you have to show up every day would be terrible for me.)

SaaS is hard. All my SaaS attempts have failed in one way or another, so I'm probably not the guy to ask about that ;)

The stuff that has worked for me has been driven by either direct sales (with a high price point), or word of mouth and relentless product testing/refinement to make it something that people are happy to go out and recommend.

My background is as a techie and I'm naturally introverted, so sales was pretty painful to learn and get good at, but it has been a huge asset to my career now that I know how to talk to potential customers/partners at a passable level. It opens up a ton of product and business model options which you can't access from behind a keyboard.

Hopefully you've made those sorts of choices much earlier than that, since platform and distribution will always have a significant impact on the rest of your product.

To use the extreme example a game: choosing to distribute via mobile basically restricts you to being free and using some sort of in-app purchase, which is going to influence everything else about your features and product design.

One of the big breakthroughs in "figuring out" startups was when folks started seeing a startup as a whole business model (including costs, channel, platforms, partners, etc.) instead of as just a product. And you ideally want to test and develop all those moving pieces together.

If you have a more specific example then maybe I can be a bit clearer.

1 Yup although it seems to be falling apart slightly more every time I get on it. It's at Port Olimpic in Barcelona. A little 8m Westerley Centaur.

2 Ya, books. As Amy Hoy once said (I think), "Passive income [from software] isn't passive." Still doing software stuff, but it takes a bunch of effort, whereas books you can launch and ignore.

3 I do, although only if I get along well enough with the founders to be happy spending a significant number of hours talking to them regardless of the outcome.

4 The main thing I didn't enjoy was feeling compelled to continue due to my obligation to investors and employees. It's a serious commitment when you take money or hire someone, and I wanted to make good on that promise to them, but it means that I forced myself to be miserable for a lot more time than I would have done if it was a smaller project which I was building with no obligations except to myself.

5 Raval, and everything ;). I especially like that people value having a good life instead of just career/money/achievement, so I find it easier to keep good priorities and be happy here. Also, very dog friendly, lots of great cafes, interesting people... I love Barcelona.

6 The IndieHackers BCN meetup began recently and seems like a good group. I'm a bit out of touch with the startups here, but I really like the creative and bootstrapping and artistic community here.

Yeah, it's completely different.

In learning conversations, I'm trying to find friendly people who I can get into a casual environment where they're happy to just chat about their lives without any defensiveness or agenda. In these cases, I try to avoid mentioning or talking about my idea at all, and I certainly wouldn't ever pitch or demo it, since all that really matters is that I fully understand the customer's life and worldview and goals and decision-making.

Sales conversations vary quite a lot depending on whether you're selling something small or big, but the main goal is just to get the other person to either advance to the next step of buying what you're selling (e.g. introducing you to their boss or lawyer or CTO) or to clearly admit that they're not interested so you can stop wasting time on them.

After a good learning conversation, you've got some new, unbiased facts about your customers' lives and worldview and goals and problems and workarounds etc.

After a good sales conversation, you've got a concrete commitment (where they give you something of value to prove their interest) or advancement to the next step of the sales process.

Books. I'm still building software also, but that's far from passive ;)

The approach took about two years of hard trial and error to figure out (I stopped doing any programming and just did meetings full time for two years), and it started to click just as my first company was failing (which was in its third year, and then we life-supported it for one more after that). I was also helped along by swapping notes with a bunch of wonderful advisors and startup buddies (most notably Salim Virani, although there were lots). Once it was working better for me, I started helping other founders at alongside working on my own next startups, and the book came at some point after that.

In terms of the summary, it's less about asking specific questions, and more about creating a casual context where you can learn about their life without biasing them by pitching your idea. The big goal (in the early stages) is just to understand what they're already doing and why. And once you've got that foundation, you can take your visionary leap to a product or solution or whatever else.

Absolutely. If you have any interest whatsoever in scale, then it's hugely worthwhile at (almost) any cost.

Of course, it's also hugely competitive now, and they only have a few minutes to evaluate each applicant, so the results can be a bit random. (Not in the sense that bad teams get accepted, but in the sense that lots of good teams don't.) So you can't let your team's morale get too hung up on the results from YC. It's a nice bonus if the stars align, but it's dangerous to depend on it.

It's pretty impactful when you realize that you've built something which is actually making strangers' lives better, and that they're grateful to you for spending the time to build it and tell them about it. Totally changed my view on marketing and sales once I realized that people are actually happy to hear about good products.

The most reliable is to start a few years early by building a personal audience (mailing list, blog, fame, etc.). People don't like hearing that because it feels unfair, but it's something you can start building today and it will begin paying dividends in a year or two by making everything else you do easy.

Apart from that, most early-stage marketing seems to be about scanning for lucky opportunities and connections, and also trying and testing stuff. I basically just use Gabe Weinberg's approach from Traction.

I'm also a big believer in just saying hello to people and using conversations to try to do sales or partnerships or whatever. It's also very hit-or-miss in the early stages before you have case studies and a repeatable sales process and everything, but you only have to get lucky once or twice early on to make a big difference.

Probably one with a top global advertiser where it was obvious after 30 seconds that they didn't care at all, so I just said, "Hey, my bad, it seems like I made a mistake setting this conversation up, so let me just leave now and let you have a longer lunch break." And she was so surprised and happy to have the extra free time that she ended up making a bunch of great introductions for us.

I had more luck by figuring out what I didn't want than by trying to think about what I did.

So my thought process was like, "I don't want to have to check my email and messages more than once a day. So that eliminates any ideas which rely on rapid customer support before I can hire a team. And I don't want to have to show up every day, which means no office and no on-site employees, remote only. Which eliminates any ideas which depend on a physical presence."

And on and on. It didn't make it easy for me to create good ideas, but it made it extremely easy for me to discard the ones which weren't a good fit for me.

We pitched to YC as a new genre of videogame which would be the interactive equivalent of a music video, with music labels as the customer and aimed at promoting new albums. We'd built a couple example games which convinced them that we were good at product, if not at business.

PG basically told us that we had pitched an agency, which would never scale, but if we could figure out an idea for a real product before the meeting ended, that he would back us. So we had a little five minute idea jam and ended up settling on a simple animation tool/toy for kids to make their own cartoons by dragging around characters as if they were puppets.

The monetization plan was to either whitelabel the whole app for brands to use around user-generated content campaigns, or to include certain items (clothing, characters, music) as a sort of paid placement.

We managed to scrape together a few customers (Sony Music, MTV, BBC, various others) but it was too specific of a product for mass adoption, so we basically took the bit they liked (which was a safe way to do social advertising or user-generated content), stripped out the animation, and tried to figure out what "social advertising" would be before Twitter or Facebook did. Which obviously went poorly for us ;)