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52 Things to Expect When You’re Expecting (to Start a Nonprofit)

One of my favorite parts about starting an organization is also one of the toughest: the range of things you need to get done each day, week, and month.  And there’s also the swing in emotions and energy.  Here’s a snapshot at what that actually looks in the first few months of a startup based on my experience:

  1. Send hundreds of cold letters to potential funders
  2. Get ignored and rejected hundreds of times
  3. Send more letters
  4. Launch a website
  5. Manage social media
  6. Recruit a board
  7. Run board meetings
  8. Manage your board
  9. Pilot your program
  10. Adjust when things don’t go as well as planned
  11. But celebrate what does
  12. Prepare for a meeting with a potential donor
  13. Quickly get over a disappointing outcome
  14. Call your mom, while skipping down the street, when the meetings lands you money
  15. Write a basic strategic plan (but hopefully ignore advice to make it a long, formal one)
  16. Design a logo
  17. Create collateral
  18. Find a friend who knows Photoshop to make it look nice for free
  19. Negotiate with vendors
  20. Interview interns
  21. Enjoy the energy of additional people as your team grows
  22. Send more cold letters
  23. Get rejected more
  24. Get a huge adrenaline rush just off a reply from a cold letter
  25. Meet with dozens of people for advice and feedback
  26. Grapple with contrasting advice and ideas from very smart people
  27. Modify your programs based on what’s working and what’s not
  28. Upset some people as a result and please others
  29. But gain confidence in making tough decisions
  30. Leave your office apartment for the first time in three days
  31. Start asking around for an open desk at an office
  32. Get excited when you’re organization finally has an address that isn’t where you sleep
  33. Realize it’s lonely as a startup leader
  34. Worse, you’re too broke to go out
  35. Stress about how little money is in your account
  36. Forget about hiring and worry about just paying your rent
  37. Go to lots of events because of the free food great networking
  38. Keep recruiting more board members with modest success
  39. But the persistence pays off when a leader who you admire says “yes”
  40. Raise your first five figure gift
  41. Email all of your prospects to share the news
  42. Then your first ten figure gift
  43. Pay yourself for the first time in three months
  44. Try to file for your 501c3 status on your own
  45. Realize it’s a pain and complicated and find a pro bono lawyer
  46. In the meantime, find a fiscal sponsor so you can accept donations
  47. Update your website, again and again and again
  48. Dial for meetings — follow-up with all the people who received your letters
  49. Ask people who are bought-in to tap their networks for introductions and money
  50. Question if you should have started an organization one week
  51. And the next week see evidence of your organization succeeding
  52. Then remind yourself: “Fuck yea, we’re going to make this happen!”

What else should be on the list?


The Greatest Startup Story of All-Time

Tim Westergren and his rugged journey founding Pandora is the greatest startup story — by far — that I’ve ever heard (or maybe second to the Founding Fathers  starting America).

I was meeting with a friend last night to discuss her startup.  We were talking about the mindset of absolute persistence it takes to be successful.  This morning, I sent her the NYTimes article, “How Pandora Slipped Past the Junkyard.”  I think it’s so inspiring that I keep an excerpt tacked to my desk:

By the end of 2001, he had 50 employees and no money. Every two weeks, he held all-hands meetings to beg people to work, unpaid, for another two weeks. That went on for two years.

Meanwhile, he appealed to venture capitalists, charged up 11 credit cards and considered a company trip to Reno to gamble for more money. The dot-com bubble had burst, and shell-shocked investors were not interested in a company that relied on people, who required salaries and health insurance, instead of computers.

In March 2004, he made his 348th pitch seeking backers. Larry Marcus, a venture capitalist at Walden Venture Capital and a musician, decided to lead a $9 million investment.

“The pitch that he gave wasn’t that interesting,” Mr. Marcus said. “But what was incredibly interesting was Tim himself. We could tell he was an entrepreneur who wasn’t going to fail.”


Let’s do a little math: from the beginning in 1999 to his breakthrough investment in 2004, Tim gave 348 pitches in roughly 225 weeks.  That’s three pitches every two weeks for five years — PLUS being told “no” about 99.9% of the time. 

Not only was Tim’s pace unbelievable, but he had to withstand the brutal mental hardship of repeated rejections all while shouldering the responsibility of payroll, revenues, and strategy.

Some might say this level of persistence is actually naive or bad business.  Sure, it turned out well, but to go on as long as he did without the traction he needed may not be the smartest thing.  I totally get that. But it doesn’t make this story any less awe-inspiring.

Thanks, Tim, for the example you set.

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