Brad Feld and Paul Kedrosky: “This Shit Is Really Messy”

That's Brad Feld in a video dialog on with Paul Kedrosky, in the short clip excerpted below, referring to entrepreneurship. (Speaking of messiness, it's also the image — a mess — that Tyler Cowen thinks best describes most people's lives.) Brad and Paul have a 40 minute conversation about the macro dynamics of the venture capital industry, the IPO market in 2010, immigration reform, and why VCs and entrepreneurs sometimes talk past each other.

I'm helping Robert Wright expand bloggingheads, a reliable source of stimulating video content, to include business folks, so let me know what you think of this conversation.

Think Different TV: Colin Marshall and Me

Episode #5 of Think Different TV features Colin Marshall, film critic, writer, and deep thinker, and me in conversation for 60 minutes. I recommend watching the video on the Vimeo site and letting it load all the way. Then you can use the chapter markings on that page. Here's an MP3 audio file of the episode. Here are the topics we discuss:

  • How do you become a good writer? Should imitate the greats? How does a unique voice emerge?
  • Embracing suckage. Your first draft will always suck. We need a museum of first drafts. Show me Shakespeare's first draft! Show me David Foster Wallace's first draft! Show me Steve Jobs' first business plan! [MP3 clip of just this part.]
  • Philosophies of self-improvement: is Merlin Mann right that we need fewer cheesy tips?
  • Bits vs. books: Would you rather go a week without blogs or a week without books? [MP3 clip of just this part.]
  • What is your eternal bio? What parts of identity are permanent? Do political beliefs tell you anything important? [MP3 clip of just this part.]
  • Friendships and the internet: how do online friends compare to "real life" ones? [MP3 clip of just this part.]
  • Long/short (bullish/bearish): formal schooling, Netflix, the state of California, democracy in China, the print book, libertarianism, Twitter. [MP3 clip of just this part.]


It's a fun and stimulating conversation. Note due to an audio problem my voice sounds a bit rough but Colin's is smooth which is good because he's the more eloquent anyway.

(thanks to Charlie Hoehn for his diligent technical assistance)

Think Different TV: Marty Nemko and Me

Episode #4 of Think Different TV features Marty Nemko, #1 career counselor, author, and U.S. News and World Report journalist and me in conversation for 35 minutes. I recommend watching it on the Vimeo site and letting it load all the way. Then you can use the chapter markings on that page. Here's an MP3 audio file of the episode. Here are the topics we discuss:

  • Where should you look for a job in these times?
  • Is China the next big entrepreneurial power? Will capitalism crush communism?
  • How does a liberal media, liberal president, and liberal congress affect things?
  • How can advocating an unpopular view make an impact?
  • Should productivity and achievement be a more important goal in life than happiness?
  • Do romantic adventures and misadventures contribute to more misery than happiness, on the whole?

It's a fun conversation with some disagreement along the way, which always keeps it interesting.


0:55 Marty's clients are now freaking out about finding a new job, not just how to move up in the ranks.

1:22 There are two groups of people: the entrepreneurial and non-entrepreneurial people. Non-entrepreneurial people should work for the government or government contractors.

3:17 What should entrepreneurial people do?

3:28 Obama has become religion, followed by environmentalism.

4:20 There'll be opportunities in mass transit, thanks to Obama.

6:00 The developing world will also be rich in opportunity.

6:30 Marty says: CHINA!

7:13 U.S. has been reluctant to consider nuclear power whereas China is doing it.

8:00 Liberal media, liberal presidency, liberal congress: Marty says this may strangle options for growth

8:24 Ben says China doesn't have a "billion entrepreneurs" as Marty suggests. Unless capitalism crushes communism, is it sustainable in the long run?

10:00 Marty disagrees and says there's an obsession with entrepreneurship.

11:00 Don't get complacent about China and entrepreneurship.

11:30 Ben says bringing in a few profs on entrepreneurship doesn't change an underlying culture.

14:25 What unpopular causes does Marty champion?

15:53 To make a difference, focus on issues where others aren't focusing.

16:15 Boys and men are treated terribly in the school system, higher education is America's most overrated product.

18:45 The censorship of the left suffocates the exploration of unpopular ideas.

19:20 Ben says the grip of CNN and NYT is loosening and the media landscape is nicheifying.

21:43 Are people under the age of 30 going to the liberal MSM for news? Ben says they won't be as influential going forward.

25:00 Is being ambitious un-cool?

26:00 The most self-efficacious people Marty knows want to die at the workplace, at their computer. Marty tries to spend as many moments of his life as possible trying to make the world better.

27:45 Marty says he doesn't like his work. It's work. Spiritually, the life well led is making a difference and working. Not to have fun.

28:38 Marty says he's not happy, sometimes content.

30:00 So much of career and life advice centers around the happiness goal. If that's not your goal, the advice is not very applicable.

30:55 Most people are made less happy by their romantic misadventures, says Marty.

31:45 "We assume love is the answer when it often is not," says Marty.

(thanks Charlie Hoehn for editing this.)

Think Different TV: Josh Kaufman and Me

Episode #3 of Think Different TV features Josh Kaufman ( and me in conversation for 40 minutes about books, self-education, the process of reading, ambition, and other topics. I recommend watching it on the Vimeo site and letting it load all the way. Then you can use the chapter markings on that page. Here's an MP3 audio file of the episode. Here's a lengthy email exchange between Josh and me on business books and related topics.


1:13 Josh says he's reading personal development books since it's the beginning of the year and you want to start the year off right

2:14 Steve Pavlina? He promotes 30 day experiments – just test something and see how you like it

4:30 Reducing goals into manageable, bite size pieces helps you start achieving them.

6:20 It's important to have at least one experimental side project going at all times

6:49 Ambition – what is it, how has the word evolved

8:48 When ambition is nakedly about power and money, it can be unattractive

10:40 There are people who are trying to do big things where the motivation is wanting to make the world better or just craftsmanship — wanting to do something for the joy of doing it, have the ability to exercise skill.

12:40 How we choose what books to read

16:28 The role of books in the self-education process

18:00 Searching Amazon and Google for the best books

18:34 Are customer reviews on Amazon reliable?

20:54 The process of reading a book – start to finish or cherry pick sections?

22:18 Take a few minutes before reading a book to think about what you want to get out of it. Selective attention.

26:50 Read until you've gotten the key points and could re-hash them to others

28:00 Recording / summarizing important nuggets from a book

30:00 Looking for mental models: concepts that have broad explanatory power

31:08 The value of book summaries / outlines that are sold?

33:00 If you're a business person, what % of books you read should be in the business book genre?

35:55 Study how people work (psychology, communication, history) and systems / processes.

37:00 Reading about science can help you understand systems / processes (ie, friction)

Think Different TV: Ramit Sethi and Me

Episode #2 of Think Different TV features Ramit Sethi of "I Will Teach You To Be Rich" and me in conversation for 40 minutes on personal finance, the media, mentors, writing good emails, and building relationships. Full content and times listed below the screenshot. I recommend watching it on Vimeo and letting it load all the way and then using the chapter markings. Here's an MP3 audio file of the episode.


0:59 Ramit explains what he's telling his readers about personal finance in these tumultuous times
5:00 Has the media done a good job explaining the crisis?
8:00 Ben says he admires those who have conceded the complexity of the situation
8:50 Ben says most young people he talks to don't really care what's going on in D.C. re: finance industry
9:08 Ben says if you're going to be an engaged citizen, you should follow what's going on even if it doesn't affect your own situation
11:16 Ramit says ignore macro-economics and focus on what you can control
13:10 Ben says if you take "only focus on things you control" to its logical end, people shouldn't focus on anything going on in Washington.
15:38 Ramit talks about his scholarship
17:48 Ramit says doing things that can scale — and reach a large audience — is most fun
19:53 What are the keys to a successful outreach to get 15 mins of a busy person's time?
21:24 Ramit says personalize the outreach
23:50 Ben says asking good questions is key and the key to a good question is specificity
24:38 Ben cites Geoffrey Moore's strategy to dominating niches and leveraging success as analogous to escalating communications in a relationship
25:35 Ramit asks Ben what the best way to get 15 minutes of Ben's time is – Ben says he's biased toward people who do their background research
27:10 Ramit: "Build a portfolio of work online that you can point people to"
28:59 Ben confesses that he judges people based on appropriate apostrophe usage in "its" and "it's"
29:54 Ramit talks about the "lamest, most ridiculous" emails he gets
31:10 Ben says in early days of a relationship your communications need a clear call to action, but eventually you should be able to say something and have the person react
32:32 Ramit says his use of "eom" in the subject line reflects the intimate nature of his relationship with Ben
33:27 Ben riffs on mentors: don't ask explicitly for someone to be a mentor, and it takes time. Relationships have a natural pace to them.
37:00 Ramit says ask your mentor good questions
38:31 Ben says also try to add value and bring up those topics for which there is no expert.