Requested by @hannieshit but changed a bunch from what she asked for, sorry, I did my best
  1. Why?
  2. Why what?
  3. Why?
  4. Why am I running for president?
  5. Why?
  6. Because I feel like I have the vision and experience to lead this fractured nation to new heights of prosperity
  7. Why?
  8. Because I've dedicated my life to serving this great nation and have the necessary experience
  9. Why?
  10. Why have I dedicated my life to service?
  11. Why?
  12. Because I felt like I had a calling to do so
  13. Why?
  14. Because I believe in the American dream
  15. Why?
  16. Because I've seen firsthand how small business owners can raise themselves up and find success if given the opportunity
  17. Why?
  18. Why have I seen that? Because I'm in touch with the common people.
  19. Why?
  20. Because even though I've been wealthy for most of my life I care about and am in touch with those not as fortunate as myself
  21. Why?
  22. Because I'm a progressive, but--
  23. Why?
  24. Hold on, I didn't get to finish my line. I'm a progressive, but a progressive who likes to get things done.
  25. Why?
  26. Because there are things that need to get done.
  27. Why?
  28. Because no one else is doing them
  29. Why?
  30. Because they're scared
  31. Why?
  32. Because politics is basically a popularity contest
  33. Why?
  34. Because most things in life are
  35. Why?
  36. Because humans are social animals and automatically lock into a kind of pack mentality
  37. Why?
  38. Did I mention the small business owners? And how they're the backbone of the American economy?
  39. Why?
  40. Because it's important that I mention them
  41. Why?
  42. Because my handlers said the public would respond well to that idea
  43. Why?
  44. I don't think I was supposed to say that--
  45. Why?
  46. Because it makes me seem insincere
  47. Why?
  48. Because a big part of the election process is predicated on preserving the illusion that the candidates are passionate and opinionated people instead of carefully groomed and cultivated collections of talking points
  49. Why?
  50. Because it's all basically very cynical
  51. Why?
  52. Because...because maybe a quest for power...maybe it's impossible to work so hard to achieve power without some element of cynicism kind of...
  53. Why?
  54. Is that maybe why people are so excited about Trump and Sanders? Because they seem to be speaking from the heart? Do you think so?
  55. Why?
  56. Do you think people would like it if I did that?
  57. Why?
  58. I'm going to give it a shot.
  59. Why?
  60. Um. Hey bozos, I want to be president more than anyone else so let me do it!
  61. Why?
  62. Hahaha that felt amazing!
  63. Why?
  64. I'm going to try it again. Um...I don't give a shit about polar bears!
  65. Why?
  66. Because they're gross! Hahahhahahha
  67. Why?
  68. Oh this is wonderful. I hate that I'm a grandparent and resent my daughter for bringing that political liability into the world!
  69. Whoa