Venture Voice – interviews with entrepreneurs

Entertaining Entrepreneurship

VV Show #24 – Bo Peabody of Village Ventures

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“Stock lockup” is a term remembered with horror by many entrepreneurs who weren’t allowed to sell their dot com shares before the bubble burst. Bo Peabody founded Tripod, which was sold to Lycos for $58 million in stock. The terms of the sale forced him to hold onto his stock for two years — while its value happened to increase ten-fold. He also happened to sell his shares just two months before the bubble burst. This lesson in luck was not lost on Bo, who wrote a book titled Lucky or Smart? However, his luck didn’t come out of nowhere. In our interview, he describes the years he spent developing his business even before the Internet was commercially available. He’s now helping entrepreneurs build businesses in parts of the country where venture capitalists typically don’t tread through his venture firm named Village Ventures.


Show notes:

2:15 Starting Tripod during college

4:45 Starting a .com without a technical background

  • “Business is fundamentally about getting other people to do what you want them to do.”
  • “If you’re an entrepreneur you need to be a B student in a lot of things.”
  • Team started with Ethan Zuckerman

6:25 Choosing a team

  • “We actually, as a rule, didn’t hire computer science majors.”

8:45 Operating out of Williamstown, Mass.

11:30 Becoming a success

12:15 Where the homepage builder idea came from

13:30 Getting the word out

  • “If there was one part of it that I regret, it was that both the press and me worked a little bit to make it [entrepreneurship] seem easier than it was.”
  • “It was harder than how we promoted it.”

18:00 Life at Lycos

  • Tripod was acquired by Lycos

19:30 When to sell the stock

20:40 Dilution

  • “When someone wants to put money into your company at a fair price you should take as much as you can get, because you never know when the market is going to turn.”

21:45 Next step

25:00 Starting businesses outside of major markets

28:30 Is venture capital still necessary to tech companies?

30:35 Google’s and Yahoo’s early aqusitions

32:00 Giving up equity

  • “The right place to start is to look to give up 25% to 35%” in an A round.

34:20 Pitching to Village Ventures

  • Make a business plan
  • Excerpt an executive summary
  • Try to get an introduction

37:15 Transitioning from entrepreneur to venture capitalist

  • “The only time I miss [being an entrepreneur] is when I’m involved with a company where I look at the CEO and say ‘God, I know I could do a better job than him or her.’”

39:15 Luck in business

  • “If you recognize luck then it humbles you a little bit.”

40:10 Entrepreneurial advice

  • “Technology does more in 10 years and less in 2 years than we think it’s going to.”

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