124 Startup Questions

I asked 300+ early stage founders one simple question.

What is the biggest question/challenge you're facing with your business right now.

Here's the complete list of what they shared:

1)Goal/KPI setting?

2)How to lead well?

3)How to run 1:1's?

4)How to build an MVP?

5)How to hire an exec?

6)Figuring out pricing?

7)How to run all hands?

8)How to give feedback?

9)How to do great work?

10)How to be productive?

11)Building a pitch deck?

12)How to crush launch day?

13)When does PR make sense?

14)How to be a good manager?

15)How to hire A+ employees?

16)Are accelerators worth it?

17)How to build distribution?

18)Why you should write more?

19)How to run great meetings?

20)Should you start a startup?

21)How to start a marketplace?

22)How to crush paid marketing?

23)How to make good decisions?

24)How to approach fundraising?

25)How to build true community?

26)How to make the most of EAs?

27)Who should be my first hire?

28)How to build a diverse team?

29)Deciding your business model?

30)How to evaluate a term sheet?

31)How do I run a great offsite?

32)Finding & picking a cofounder?

33)How to build & manage a board?

34)How to find product market fit?

35)Reasons not to start a startup?

36)How to have hard conversations?

37)How to evolve as a startup CEO?

38)How to run leadership meetings?

39)How to talk to/learn from users?

40)How to build/grow a growth team?

41)How to improve conversion rates?

42)How to run a performance review?

43)How to onboard an employee well?

44)How to effectively run a startup?

45)How to build your sales function?

46)When/how to get out of the weeds?

47)How to do user/customer research?

48)How much equity to give employees?

49)How to get PR or make your own PR?

50)How to deal with failure/setbacks?

51)How to think about unit economics?

52)When to focus on building systems?

53)How to find/evaluate startup ideas?

54)What makes great founders so great?

55)How to start a consumer social app?

56)How to think from first principles?

57)How to deal with imposter syndrome?

58)How to acquire your first customers?

59)How to pitch investors successfully?

60)How to find great problems to solve?

61)How to successfully sell your startup?

62)How to raise your pre-seed/seed round?

63)How to split equity across cofounders?

64)How to build a strong startup culture?

65)How to avoid common fundraising traps?

66)How/why to do things that don't scale?

67)How to run a killer interview process?

68)Should I use jobs to be done framework?

69)When is it time to pivot & how to pivot?

70)How to be deeply self-aware as a leader?

71)How to build a marketing/growth strategy?

72)How to manage your startup finances well?

73)How to crush product/product development?

74)What to do if you're running out of cash?

75)What matters most: market, product, team?

76)How to build a customer success function?

77)How much should I pay myself as a founder?

78)What's the right amount of money to raise?

79)How to find & learn from your power users?

80)When to do annual planning/how to crush it?

81)When to hire for experience vs. potential?

82)When is the right time to sell my business?

83)How to be an independent & critical thinker?

84)What are the reasons not to build a startup?

85)How to prioritize the right product features?

86)When is the right time to throw in the towel?

87)When is the right time to launch your startup?

88)How to make culture more than words on a wall?

89)Investor terms/not getting screwed when you raise

90)How much of building a startup is skill vs luck?

91)How to set up great SOPs/internal documentation?

92)How to build a remote org & culture successfully?

93)How to build a robust organic marketing strategy?

94)When to fire someone/how to fire compassionately?

95)The difference between good and bad startup ideas?

96)What are the common ways that startups waste time?

97)When is the right time to build a leadership team?

98)What are the common ways that startups waste money?

99)How did successful startups in my space do X, Y, Z?

100) The biggest mistakes to avoid when going to market?

101) When to invest in brand/how to build a great brand?

102) What should I spend my time on as a startup founder?

103) How do I know if I'm doing my job well as a founder?

104) The most important mental models to know as you build?

105) How to decide between in-person, hybrid, fully remote?

106) How to lead a company through uncertainty/tough times?

107) What's the best path to ultimately build/run a startup?

108) What are the different type of startup business models?

109) What are the common issues most startups face early on?

110) How to test startup ideas you're interested in building?

111)How to raise money if I don't know VCs/have connections?

112) How to negotiate title/comp with a new/existing employee?

113) How to go from reactive to proactive within your startup?

114) How to create/execute a great product-led growth strategy?

115) How to cold email? Investors, employees, partners, customers

116) What are the most common mistakes early stage founders make?

117) How to set up analytics well so you measure the right things?

118) When does it make sense to work with a coach/how to find one?

119) How to leverage design & design thinking when building product?

120) How transparent should I be with my team around financials, etc?

121) When to hire a chief of staff/what to expect from a chief of staff?

122) What are the most important legal things to do when building a startup?

123) How to uncover blindspots as a non-technical founder building software?

124) How to structure communications in your company (sync, async, email, slack, etc)?