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TC08 Chicago – Ask The Wizard Live – Dick Costolo Talks Entrepreneurship

Dick Costolo gave a really raw, heartfelt talk about Feedburner, venture capital fund raising and venture capital. I won’t dwell on it here, but even though I’ve never worked directly on anything with Dick, we’ve had an amazing exchange of ideas and conversation over the years. Someday I hope I can take that relationship to an even higher level – mostly for the personal growth that I know it would cause rather than the monetization events it would likely bring. He gets it. Dick never stops learning and interacting every day. That restlessness is critical to his perpetual personal growth. Sorry, I think I did dwell on it a bit….anyway, here are my raw notes or his passionate speech that bordered on a rant at times…in the most positive way:

4 startups including Feedburner

Feedburner all founders had same equity percentage – very important to teamwork dynamic and success

Entrepreneurs worry too much about valuation

Market Opportunity – sizing, does the market need it, team, product, market

Location – No Black Swans

Cash – Don’t kid yourself

CCs, your misunderstood friends – finding the right one

Options/Equity – options, pool, common stock, dilution

Board Meetings – Should be strategic discussions, not operations, board package, timing and who should attend…

Hiring – Best Available Athlete, Roles and Flat Organizations, Hierarchy begets bureaucracy, replace with tools (eg SFA)…Don’t hire for position…hire people that can do almost anything…a jack of all trades…this reminds me of a lot of what BlackRock was like…I sat at 23 desks in 4 years, I don’t know how many projects I worked on during my time there, I understood every process in the company.

No offices. Open culture and communication are critical…

Experience or Enthusiasm?

Performance – performance reviews and subjectivity


Growing the team
– Sales and Marketing – don’t hire until you are ready to sell
– Interview process – long

Product Development and Business Strategy
Serendipity and Adjustment – visit to the eye doctor

Launch Late to Launch Often – data models and programs architected for extensibility can beat point solutions every time (I agree this is critical)

Focus and Speed of Execution are a competitive advantage
– Internationalization
– Early biz dev can hurt you, so can any biz dev

Competitive advantage
– Be first to market, not most sophisticated, not the best product, be itirative and fast

Let people you don’t know help you win (open/api) and provide your products/service with the best opportunity to evolve in the market

Startups who ask people to sign NDAs are stupid! Gave a great (and way too fast!) discussion on this…I wish he’d write a detailed blog post of his rant. ?

Quantum barriers to entry and market share – Get market share, market share is the only thing you should focus on.

Revenue plan: Don’t kid yourself. Revenue ALWAYS ramps slower than you think it will.

Don’t do unnecessary things because you think you’re supposed to

Try to let the business model come to you
– Easy to say, not easy to do
– It’s easier to lower the price than to raise the price?
– Look for always on opportunities

Don’t worry about an exit strategy, worry about everything else

Be a big small company
– Public face of the company
– Have a specific voice, have a culture

Be competitive on your merits

1 thought on “TC08 Chicago – Ask The Wizard Live – Dick Costolo Talks Entrepreneurship

  1. […] hours of pure madness! Most people noticed the great speeches by Gary Vee from Wine Library TV and Dick Costolo (aka ask the wizard) and others. But what I really appreciated was the other things that the day […]

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