
1) The Launch Pad: Inside Y Combinator, by Randall Stross
2) The Founder's Dilemmas, by Noam Wasserman
3) The Hard Thing About Hard Things, by Ben Horowitz
4) Zero to One: Notes on Startups, by Peter Thiel, Blake Masters
5) Venture Deals, by Brad Feld, Jason Mendelson (I haven't read, but heard good things about it)
ps: title is missing "ASK HN".
Emotional Intelligence by Daniel Goleman (Fantastic Look into how we as humans work and how to deal with each other and ourselves)
Ready Player One by Ernest Cline (Enjoyable and entertaining)
The Martian by Andy Weir (The Audiobook of this was AMAZING! The book is still amazing especially for technical people)
The Hard thing about Hard things by Ben Horowitz (I think it would be a great book for people who are already running companies.)
Think and Grow Rich by Napoleon Hill (It had some interesting parts. Wasn't a bad book, but also not crazy memorable)
Boundaries in Dating by Henry Cloud (I found the advice for the christian dating relationship to be a honest eye opener. This book taught me a lot about myself.)
The Launch Pad by Randall Stross (How I found Y Combinator and Hacker news. I really enjoy the startup community and love the fact that this introduced me to it)
The richest man in Babylon by George S Clason (OMG EVERYONE SHOULD OWN THIS BOOK!!! It teaches you about handling money in one of the most entertaining ways I've ever read. It was crazy good and I reread it often.)
Creativity Inc by Ed Catmull
(Great read about the interesting problems solved and the fight for survival to one day bring about a worthy ideal)
>> Computer History & biographies:
The New New Thing: A Silicon Valley Story, Michael Lewis
The Second Coming of Steve Jobs, by Alan Deutschman
Machines of Loving Grace, by John Markoff
The Innovators, by Walter Isaacson
Ghost in the Wires, by Kevin Mitnick
Idea Man: A Memoir by the Cofounder of Microsoft, by Paul Allen
Creativity, Inc, by Ed Catmull (reading)
>> Startups:
The Hard Thing About Hard Things, by Ben Horowitz
The Founder's Dilemmas, Noam Wasserman
The Launch Pad, by Randall Stross
>> Other books:
Trilogy: Off to Be the Wizard (series), by Scott Meyer
Search Inside Yourself, Chade-Meng Tan
Joy on Demand, Chade-Meng Tan (reading)
It's neither.
Early stage investors make calculated bets on teams that they think can succeed in the long run. Valuation is a technicality, and depends on how well founders can pitch their idea, and how desired they are by other competing VCs. Ultimately, what really matters, is the potential of the team, and the size of the space they're exploring.
In this case, Sequoia is not investing in a simple messaging app that can be "replicated in a couple of hours" (regardless if that's true or not). They're giving money to a team they believe can do something great with it. And one that spent 3 months being personally trained by Paulg plus some of the best minds in the startup ecosystem, to seize opportunities and create something big.
From a purely statistical perspective, 80% of investments will fail. It's very likely that Magic will fail, too. But the 20% that succeed will pay for all the other ones.
For anyone interested, I strongly recommend "The Launch Pad: Inside Y Combinator" [1], by Randall Stross. It shows in incredible detail the ins and outs of YC, and explains why angels and VCs do things that seem, at face value, crazy for outsiders. It will give you a totally different perspective on deals like this.
[1] http://smile.amazon.com/Launch-Pad-Inside-Combinator/dp/1591...
Personally, if I were in a peer group any of whose members managed to succeed, I'd be much more motivated to give it another try even if my own effort had failed, compared to having made the effort alone.
edit: But I agree with you in another way. Hurting for the lack of such a credential is a self-confidence issue. If you managed to hunker down and make something on your own, you're already ahead of the unwashed masses. Surely making a case for that is not so difficult in comparison (to the effort itself).
You should reframe your perspective. Instead of "failing for 10 years", you should look at all the knowledge and skills you've acquired during this time. That alone is already better than the majority of the population, and I bet lots of people would kill to be in your position. And you're only 25.
Also, it doesn't surprise me that you didn't succeed, despite your effort. The odds are simply against you [3]. Failing is the expected outcome. What is wrong is your expectation of success, just because you spent 10 years trying hard. Sorry to say, but that's not how it works [4].
You should take a serious look at your professional career, and consider other options. Building your own business is not the only way to cultivate a successful career, build a strong network, and learn to be a better professional. And remember that many successful entrepreneurs started after 30 (or 40, or 50), so that option always exist. Different challenges, but still doable.
You mentioned that you like to read. Here's some references that I wish I had when I was 25:
[1] The Defining Decade: Why Your Twenties Matter--And How to Make the Most of Them Now http://smile.amazon.com/The-Defining-Decade-Twenties-Matter-...
[2] Search Inside Yourself: The Unexpected Path to Achieving Success, Happiness (and World Peace) http://smile.amazon.com/Search-Inside-Yourself-Unexpected-Ac...
[3] The Founder's Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup http://smile.amazon.com/Founders-Dilemmas-Anticipating-Found...
[4] The Launch Pad: Inside Y Combinator http://smile.amazon.com/Launch-Pad-Inside-Combinator/dp/1591...
[5] This Is Water: The Original David Foster Wallace Recording http://smile.amazon.com/This-Water-Original-Wallace-Recordin...
(all are clean links; no affiliate)