Two more good reads:

Founders at Work

Masters of Doom

Founders at work

Jessica Livingston's book, Founders At Work is great simply because it covers a ton of different area's and different perspectives. If anything, the reader should come away with the realization that 1. luck plays a big part and 2. there's no one way to be successful.

Some would say I read too much, but I really enjoyed:

founders at work: Steve Wozniak (Apple), Caterina Fake (Flickr), Mitch Kapor (Lotus), Max Levchin (PayPal), and Sabeer Bhatia (Hotmail) tell you in their own words about their surprising and often very funny discoveries as they learned how to build a company. (This is one of my favorite books ever!)

the art of the start:Kawasaki provides readers with GIST-Great Ideas for Starting Things-including his field-tested insider's techniques for bootstrapping, branding, networking, recruiting, pitching, rainmaking, and, most important in this fickle consumer climate, building buzz.

the innovator's dilemma: Focusing on “disruptive technology,” Christensen shows why most companies miss out on new waves of innovation. Whether in electronics or retailing, a successful company with established products will get pushed aside unless managers know when to abandon traditional business practices. Using the lessons of successes and failures from leading companies, The Innovator’s Dilemma presents a set of rules for capitalizing on the phenomenon of disruptive innovation.



And in terms of getting your life together to the point where you are responsible enough to lead others, I would highly suggest Getting Things Done by David Allen

Hi /r/techsin101,

I have a few resources that don't match exactly what you're looking for, but were interesting non-the-less.

• Founders at work, a book by one of the core people at Y-Combinator: http://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788
  
• Bootstrapping stories: https://37signals.com/bootstrapped
  
• A bit dry, but fascinating if you have the mind for it, a review of the SBIR Program (a government program that gives grants between 150k and 750k to small businesses) http://www.nap.edu/catalog/11929.html
  
• browse medium, there's thousands of stories there

Founders at Work is a great read. It's first-person stories from people who founded great companies.

http://www.foundersatwork.com/

Edit to add amazon link: http://www.amazon.com/Founders-Work-Stories-Startups-Problem-Solution/dp/1430210788

I love "How they did it" stories. They are so inspiring and as an entrepreneur myself, they remind me to keep pushing even when times are hard.

A couple of resources you could use (and I recommend that every current and future entrepreneur takes a look at)

1. The book Founders at Work --- The stories of how the Paypal co-founder foound himself passed out on the floor on the day of the big launch and so many others like these were SUPER INSPIRING
   
   
2. A YouTube channel called This Week in Startups --- Jason Calacanis has interviewed almost every founder of every tech startup in the last 10 years. I watch this show a couple of times a week and I have always learned something that I could use in my own startup

This one is also one of my favoriates: Founders at Work : Stories of Startups' Early Days

whats the purpose of the research ?

read founder at work http://www.amazon.com/Founders-Work-Stories-Startups-Problem-Solution/dp/1430210788

When I find myself in this position (which I'm currently in after burning 18 months and a big chunk of cash on my last startup only to have it fail), I usually slink off, lick my wounds, do a lot fo reading and then approach my next project feeling a little more educated, refreshed, and ready.

Some suggestions if I may:

• The Four Steps to the Epiphany: Successful Strategies for Products that Win: http://www.amazon.com/Four-Steps-Epiphany-Successful-Strategies/dp/0976470705
  
  
• Founders at Work: http://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788/
  
  
• Business Model Generation: http://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417/
  
  Founders At Work is an easy, fun and somewhat inspirational read. The concept behind 4 Steps to an Epiphany is pretty simple, so odds are you won't need to read the whole book as its a little dry. It is authored by Steve Blank and I highly recommend watching his lectures on youtube. Business Model Generation was a mind bender and I've read it about 6 times. I've run all my past businesses and current business through it plus a couple non-profits. It is fantastic and I love it.
  

Great - btw. I really enjoyed reading "Founders at work" - I got that hint from Seibel's announcement of his upcoming "Coders at work"

The two books I'd recommend are Founders at Work
and Don't Make Me Think . even though this is more on the technical side it's an amazing book about user experience which most entrepreneurs should try to master :)

"Behind the scenes" meaning stories that aren't fabricated to make good TV but to give the viewer a better understanding of what goes on behind a product / website. TED talks are great with that so I'd highly recommend watching these https://www.ted.com/talks?sort=newest&topics%5B%5D=entrepreneur

The more dramatic but easy to keep in the background type shows are

• Shark Tank
  
  
• The Great Food Truck Race
  
  
• Undercover Boss
  
  
• Hotel Hell
  
  
• Kitchen Nightmares
  
  Hopefully some of these help!
  
  

In his interview for the book Founders at Work he clearly attributes his early success to luck. They were rapidly pivoting and threw a hail marry that landed.

Having said that, there's a reason why serial entrepreneurs are aggressively sought after and cherished for advisory roles by early-stage startups and entrepreneurs. Guys that can produce hit after hit are not merely lucky, they know what they're doing.

A lot of it is knowing the right people, the trust that they've built with investors that allows them to make decisions without as much scrutiny, and finally the fact they've weathered the storm before. Simply being able to avoid mistakes of the past is huge. Also having been successful at least once before, they tend to trust their instincts more in the face of serious risky decisions; something that new guys out the gate do regularly.

On the flipside, they wouldn't be where they are if they didn't have a rare combination of skill and risk-taking.

As someone who has done this over the past few years, my two pieces of advice for your next steps are (skipping accounting as I assume you have that covered!) ...

1. Don't write native iPad/iPhone apps. Write a web application that works on iPad, iPhone, Android, PC. Sell it to businesses on a subscription basis. Businesses make rational buying decisions, you'll ideally displace something they are already paying for, they are easier to market to and you can build up relationships. By writing a web app you aren't dealing with the app store, free apps, publication woes, limiting your supported devices and the expectations consumers have around stupidly low app pricing.
   
2. As it sounds like you may have some assets worth protecting, setup an entity with liability protect from the start. This includes a bank account, etc. I picked an LLC as it is easy to create, easy to manage, I wasn't going to be taking on investors in the short term and could still elect to be taxed as an S-Corp. I didn't use my lawyer - we talked about it over lunch, but with a single member LLCs it was so simple to setup it wasn't worth getting him to do it (I know there are lots of Reddit lawyers who disagree and feel only they can fill in the few bits of paperwork correctly!)
   
   As for books to read. I found Founders at Work the most motivating as you realize how many different paths to success there are.
   
   Good luck!

The number of great books to be read on business itself is beyond enumerable. There is even a book on the 100 best business books written here: http://100bestbiz.com/

For helping your brother decide whether he has the stomach and skills it takes to be an entrepreneur, I'd suggest Art of the Start by Guy Kawasaki and Founders at Work

At the end of the day, it's a bipolar ride that I'm not sure any book can prepare you for...

Mayor Steinberg, you might want to dip into this book:
https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788/
(even just the "look inside the book" part, starting with the foreword)

Entrepreneur Reading List

1. Disrupted: My Misadventure in the Start-Up Bubble
   
2. The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win
   
3. The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It
   
4. The Art of the Start: The Time-Tested, Battle-Hardened Guide for Anyone Starting Anything
   
5. The Four Steps to the Epiphany: Successful Strategies for Products that Win
   
6. Permission Marketing: Turning Strangers into Friends and Friends into Customers
   
7. Ikigai
   
8. Reality Check: The Irreverent Guide to Outsmarting, Outmanaging, and Outmarketing Your Competition
   
9. Bootstrap: Lessons Learned Building a Successful Company from Scratch
   
10. The Marketing Gurus: Lessons from the Best Marketing Books of All Time
    
11. Content Rich: Writing Your Way to Wealth on the Web
    
12. The Web Startup Success Guide
    
13. The Best of Guerrilla Marketing: Guerrilla Marketing Remix
    
14. From Program to Product: Turning Your Code into a Saleable Product
    
15. This Little Program Went to Market: Create, Deploy, Distribute, Market, and Sell Software and More on the Internet at Little or No Cost to You
    
16. The Secrets of Consulting: A Guide to Giving and Getting Advice Successfully
    
17. The Innovator's Solution: Creating and Sustaining Successful Growth
    
18. Startups Open Sourced: Stories to Inspire and Educate
    
19. In Search of Stupidity: Over Twenty Years of High Tech Marketing Disasters
    
20. Do More Faster: TechStars Lessons to Accelerate Your Startup
    
21. Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business
    
22. Maximum Achievement: Strategies and Skills That Will Unlock Your Hidden Powers to Succeed
    
23. Founders at Work: Stories of Startups' Early Days
    
24. Blue Ocean Strategy: How to Create Uncontested Market Space and Make Competition Irrelevant
    
25. Eric Sink on the Business of Software
    
26. Words that Sell: More than 6000 Entries to Help You Promote Your Products, Services, and Ideas
    
27. Anything You Want
    
28. Crossing the Chasm: Marketing and Selling High-Tech Products to Mainstream Customers
    
29. The Innovator's Dilemma: The Revolutionary Book that Will Change the Way You Do Business
    
30. Tao Te Ching
    
31. Philip & Alex's Guide to Web Publishing
    
32. The Tao of Programming
    
33. Zen and the Art of Motorcycle Maintenance: An Inquiry into Values
    
34. The Inmates Are Running the Asylum: Why High Tech Products Drive Us Crazy and How to Restore the Sanity
    
    

    Computer Science Grad School Reading List
    

    
    

35. All the Mathematics You Missed: But Need to Know for Graduate School
    
36. Introductory Linear Algebra: An Applied First Course
    
37. Introduction to Probability
    
38. The Structure of Scientific Revolutions
    
39. Science in Action: How to Follow Scientists and Engineers Through Society
    
40. Proofs and Refutations: The Logic of Mathematical Discovery
    
41. What Is This Thing Called Science?
    
42. The Art of Computer Programming
    
43. The Little Schemer
    
44. The Seasoned Schemer
    
45. Data Structures Using C and C++
    
46. Algorithms + Data Structures = Programs
    
47. Structure and Interpretation of Computer Programs
    
48. Concepts, Techniques, and Models of Computer Programming
    
49. How to Design Programs: An Introduction to Programming and Computing
    
50. A Science of Operations: Machines, Logic and the Invention of Programming
    
51. Algorithms on Strings, Trees, and Sequences: Computer Science and Computational Biology
    
52. The Computational Beauty of Nature: Computer Explorations of Fractals, Chaos, Complex Systems, and Adaptation
    
53. The Annotated Turing: A Guided Tour Through Alan Turing's Historic Paper on Computability and the Turing Machine
    
54. Computability: An Introduction to Recursive Function Theory
    
55. How To Solve It: A New Aspect of Mathematical Method
    
56. Types and Programming Languages
    
57. Computer Algebra and Symbolic Computation: Elementary Algorithms
    
58. Computer Algebra and Symbolic Computation: Mathematical Methods
    
59. Commonsense Reasoning
    
60. Using Language
    
61. Computer Vision
    
62. Alice's Adventures in Wonderland
    
63. Gödel, Escher, Bach: An Eternal Golden Braid
    
    

    Video Game Development Reading List
    

    
    

64. Game Programming Gems - 1 2 3 4 5 6 7
    
65. AI Game Programming Wisdom - 1 2 3 4
    
66. Making Games with Python and Pygame
    
67. Invent Your Own Computer Games With Python
    
68. Bit by Bit

I would also recommend the book Founders at Work which has stories just like these.

https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788

Atlas Shrugged - Ayn Rand ( link )

Never Stop Pushing: My Life from a Wyoming Farm to the Olympic Medals Stand - Rulon Gardner ( link )

Often Wrong, Never in Doubt: Unleash the Business Rebel Within - Donny Deutsch ( link )

It's True! It's True! - Kurt Angle ( link )

Everyone Else Must Fail: The Unvarnished Truth About Oracle and Larry Ellison - Karen Southwick ( link )

Founders at Work: Stories of Startups' Early Days - Jessica Livingston ( link )

Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality - Scott Belsky ( link )

Kick Your Own Ass: The Will, Skill, and Drill of Selling More Than You Ever Thought Possible - Robert Johnson ( link )