I was laughing with friends this past weekend about how our initial business was called ChubbyBrain and what an actually great name it was (it’s memorable) but how stupid the initial business idea it was. Think Yelp for startups.  I’m not sure the idea was all that bad actually in retrospect as ProductHunt is sort of the same thing.  I can say without a doubt our execution sucked.

And it got me thinking about all the other ways I’ve screwed up as the CEO of a startup. And so I started writing them down and in 10 minutes, I had a long-ass list of 65 screw ups. What that tells me is that with another 10 minutes of thought, this list could get get into the hundreds.

So here they are in no particular order.  As you’ll see, my screwups span HR, product, sales, operations, admin, etc.

Yes, I’m what you might call multi-talented.

I’m probably still screwing up some of these things.

1. Hired under pressure.
2. Fired too slow
3. Give a shit about new competitors too much
4. Took meetings with VCs ill-prepared and uninterested in raising money. I looked dumb and it took me away from what I like most and what we need to do.
5. Didn’t anticipate where we’d need to hire as well as I should have
6. Got bogged down in details with game-changing hires and lost them
7. Believed in the new hire messiah, i.e., a new teammate would be the savior in a particular area we were weak in. Never works.
8. Didn’t focus on sales enough
9. Were too humble about our technology
10. Been more proactive outreach to journalists
11. Tried to use jargon as thought that’s what people wanted to read. Sounded robotic and douchey. Talk to people like people.
12. Didn’t realize annoying people stay annoying forever. Skills change, personality doesn’t
13. Didn’t check references
14. Didn’t know how to check references
15. Took advice from non-customers (who would never be customers)
16. Thought partnerships would solve distribution
17. Chased fads. Remember when gamification and badges were the shit. It was when people cared about Foursquare. We thought people wanted badges and gamification so we worked on that. Waste of time.
18. Stayed in a crappy office too long
19. Experimented with remote workers too early
20. Shiny object syndrome aka got distracted
21. Thought cheap pricing would help us win
22. Didn’t raise prices quickly enough
23. Got too cute with pricing
24. Hired smart folks and said we will figure it out later
25. Didn’t outsource payroll soon enough
26. Terrible on-boarding of new teammates
27. Unreasonable expectations of users. We need to make it simple. It’s not their job to figure it out.
28. Wasted time on poor leads
29. Tried to be all things to all people
30. Dress poorly
31. Did things by committee too much
32. Didn’t involve people like I needed too
33. Thought culture would just happen
34. Didn’t visit customers enough
35. Took rejection too personally
36. Tried to be a “salesy” sales guy and felt uncomfortable and it didn’t work
37. Didn’t ask enough questions when pitching
38. Poor post demo follow up
39. Didn’t ask for sale
40. Would spoon feed objections to prospects
41. Didn’t realize content was our golden goose
42. Tried to find other acquisition channels without exploiting what we were already good at
43. Didn’t repurpose content like we should have
44. Underinvested in our newsletter
45. Didn’t do enough 1 on 1’s with folks on the team
46. Didn’t give feedback frequently enough
47. Provide more context about where we’re going and why everyone is doing what they’re doing to the team
48. Worried too much about quality when we should have shipped a “rawer” product
49. Ring the gong more even to celebrate small wins
50. Fire bad advisors quickly
51. Don’t buy stuff from customers. It gets complicated.
52. Should’ve sued a partner who dicked us over but worried about legal expenses too much
53. Hired customer success earlier
54. Started really using Twitter earlier
55. Get another blazer for those important meetings cuz it looked stupid wearing the same one all the time. See dress better.
56. Gotten our sweet t-shirts earlier and send them to customers
57. Don’t get coffee with random people with no agenda or idea why we were meeting
58. Wasted time with people who wanted to integrate with CB Insights but who had no money to pay for data nor any clue what they wanted
59. Should have raised prices a lot higher, a lot quicker
60. Responded to trolls on the internet
61. Didn’t get scientific about the content we should do early enough
62. My desk is a freakin’ mess
63. Didn’t give people clear enough instructions assuming they’d figure it out
64. Thought this might be a good logo
65. Eat together more as a team
66. Keep the team better updated on new capabilities and what folks are working on

I’ll update this post over time.  Lots more screwups to come (hopefully I’m learning)