100 Mistakes I Did in My Businesses

In the past 15 years, I’ve started four businesses—from my first tech store as a family business to uMake, Gooddesk, and others that never made it to the light. I started as a born geek who turned into an entrepreneur with zero business background, and this journey taught me more than any school could. I’m writing this to reflect, to share what I’ve learned, and to help others who might be unknowingly repeating the same mistakes I made.

Each point here is raw, real, and written in my voice—not polished for perfection, but preserved for authenticity. These are not complaints or regrets; they are lessons. Some mistakes happened more than once, in different contexts. Some may seem small. But each had its price. I’ll be writing deeper blog posts about each one with real examples and suggestions on what to do instead. This is just the beginning.

The People Mistakes

1. Worked with wrong business partners
Some cared only about their money, others wanted authority without responsibility. Misalignment destroys momentum.

2. Worked with partners who didn’t appreciate or respect my value
When your value is unseen, your energy is drained. Mutual respect is fuel.

3. Got idle partners who did not help the business other than the initial investment
Money isn’t partnership. Engagement is.

4. Worked with friends who did not separate friendship and business
What starts warm can end cold when roles blur.

5. Worked with family members who did not separate between family and business
Hard to hold accountable. Even harder to fire. Emotion kills clarity.

6. Worked with partners who put their self-image and self-interest over the business
Self-preservation masked as contribution. The business suffers silently.

7. Hired poor talent
Skills on paper mean nothing if the mindset doesn't match.

8. Hired people like me or people I liked
Comfort hires create gaps. You need complement, not clone.

9. Had useless team members
Dead weight costs more than salary. It drags everyone down.

10. Grown the team too early with the illusion of growth readiness
Premature scaling is expensive. Optimism is not a strategy.

11. Did not stop or fire toxic team members on time
Toxicity spreads like wildfire. Delay is damage.

12. Was too easy with my team
Kindness without standards breeds mediocrity.

13. Was not demanding enough when I needed to be direct or strict
Clear expectations are a gift, not a punishment.

14. Didn’t maintain the wellbeing of my team
Burned-out people don’t build thriving businesses.

15. Didn’t clarify roles/responsibilities in the team
Chaos comes from “who’s doing what?” confusion.

Strategy & Direction Mistakes

16. Took on projects that didn’t align with long-term goals
Short-term money = long-term distraction. Stick to the map.

17. Focused on the wrong things
Cool doesn’t mean effective. Attention ≠ progress.

18. Focused on doing good vs profitability
Impact needs fuel. Without revenue, you’re running on fumes.

19. Tried to do everything our clients dreamed of—even without the resources
Overpromising leads to underdelivering. It's better to say no early than apologize later.

20. Didn’t monetize everything we had
Untapped value is invisible revenue.

21. Got distracted with too many services instead of enhancing the core
Spread thin, executed poorly. Depth over breadth wins.

22. Didn’t prototype/test ideas before investing heavily
Skipping validation is like building a house on sand.

23. Operated without a clear business model in early stages
No model = no direction. You can’t measure what doesn’t exist.

24. Misjudged market size or demand
Assumptions are expensive when the market says “meh.”

25. Entered into a market that was not ready for the product or service
If you have to educate before you sell, expect a long uphill road.

Money & Finance Mistakes

26. Wanted funding too early
Funding too soon forces you to grow before you're ready.

27. Got funding on the wrong conditions
Desperation gives away power. Bad terms haunt you.

28. Got the wrong money, not smart money
A check is not help. Strategic support matters more.

29. Grew without financial stability
Revenue ≠ cashflow. Stability first.

30. Didn’t manage business cashflow
Ran out of air while sprinting. Cash is oxygen.

31. Used my salary to cover business expenses
Blurring personal with business = burnout and resentment.

32. Didn’t deduct my salary or compensate myself
No reward leads to internal resistance. Founders need fuel too.

33. Didn’t have a financial advisor from day one
Flying blind in finances means crashing sooner or later.

34. Didn’t have proper bookkeeping and accounting from day one
Chaos piles up quietly—until tax season punches you.

35. Kept debt piling up with hope for better days
Hope is not a payment plan. Be real about numbers.

Structure & Systems Mistakes

36. Didn’t build internal systems for efficiency
Manual chaos is unsustainable. Systems scale what humans can’t.

37. Didn’t document SOPs, communication, or agreements
Assumptions break under pressure. Documentation protects you.

38. Didn’t enhance business conversion rate
Visitors are meaningless if they don’t become customers.

39. Didn’t create a board of directors or advisors
No external feedback loop. Echo chambers kill growth.

40. Didn’t have a business coach early
You don’t know what you don’t know until it costs you.

41. Didn’t speak to a mentor weekly
Regular feedback is a mirror. Without it, you get lost in your own reflection.

42. Didn’t update communication channels accordingly
Old systems slow down new speed. Evolve or stall.

43. Didn’t follow up on leads/clients/partners in time
Fortune is in the follow-up. Silence kills momentum.

44. Didn’t maintain existing clients to increase LTV
Chasing new clients while ignoring loyal ones is a leaky bucket.

Personal Mistakes

45. I put business first over my life
Everything good suffers when you do that. Including the business.

46. Worked long or late hours too often
Hustle isn’t sustainable. It breaks you before you succeed.

47. Didn’t maintain a work routine to keep flow-state or productivity
Disorder kills creativity and consistency.

48. Didn’t care for my health, which affected my productivity
A broken body can’t build a business.

49. Burned out and didn’t recognize the signs early
Burnout whispers before it screams.

50. Took responsibility more than I should have
Over-owning drains leaders and creates dependency in others.

51. Let fear of failure or judgment affect my decisions
Building while scared makes you build small.

52. Didn’t celebrate small wins
Without wins, the journey feels endless.

Execution Mistakes

53. Didn’t say no
Every yes costs something else. Guard your time and energy.

54. Didn’t delegate early
Doing everything yourself is not noble. It’s naive.

55. Didn’t fail fast
Hanging onto bad ideas burns time and money.

56. Didn’t fire fast
Dragging deadweight kills morale and culture.

57. Made quick decisions without enough information
Speed isn’t clarity. Pause is power.

58. Made slow decisions when I should’ve moved fast
Missed timing is missed opportunity.

59. Kept going when I should’ve stopped—projects, tasks, people
Momentum can become a trap. Know when to cut losses.

60. Repeated things that didn’t work (e.g., same agency or ad strategy)
Optimism without analysis is costly.

61. Ignored customer feedback for too long
Customers tell you what to fix—if you listen.

62. Didn’t balance quality, cost, reliability, and reach
Each matters. Overweighting one sacrifices the others.

63. Didn’t ignite the sales machine—focused only on marketing
Marketing attracts. Sales closes. You need both.

64. Didn’t analyze business metrics regularly
Data tells the story. Without it, you’re guessing.

Operational & Legal Mistakes

65. Didn’t have a professional business lawyer from day zero
Legal loopholes hurt most when you're succeeding.

66. Didn’t get proper official docs for legal/tax from auditors or partners
Paperwork issues will always find you—eventually.

67. Didn’t have strict service agreements with providers
Assumptions become arguments.

68. Didn’t work with reliable suppliers/service providers
Your backend defines your customer’s experience.

69. Website wasn’t always up and running or maintained
A broken site equals a broken first impression.

70. Deprioritized formal setups or industry-standard forums
Culture matters. Appearances matter in some markets.

Mindset & Culture Mistakes

71. Thought we knew more than we actually did
Overconfidence is invisible until it fails publicly.

72. Gave permission/authority to unprepared or incompetent people
Premature trust leads to big messes.

73. Over-promised and under-delivered to clients
Intent doesn’t erase disappointment.

74. Didn’t invest in team learning and development
A stagnant team is a dying one.

75. Underestimated branding and positioning
You can’t sell if people don’t get why you matter.

76. Expected people to understand our value or terminology
Assume zero knowledge. Clarity wins.

77. Didn’t maintain routine content—newsletters, updates, etc.
Silence makes people forget you.

78. Focused only on social media, ignoring other channels
Diversification wins attention.

79. Didn’t build meaningful win-win partnerships
One-sided deals die quickly.

80. Worked with people who had envy or bad faith
Bad energy infects outcomes.

81. Put my values aside in desperation
Compromise hurts most when you regret it later.

82. Started too early or too late
Timing isn’t everything, but it shapes everything.

83. Operated without a clear goal
Wandering feels busy. But it gets you nowhere.

84. Operated without KPIs
What you don’t track, you can’t improve.

Final Lessons

85. Relied on trust and faith instead of accountability
Good intentions don’t replace systems.

86. Took uncalculated risks
Risk is fine. Blind risk isn’t.

87. My love of the mission made me run it like a charity
Profit doesn’t cancel purpose. It sustains it.

88. My optimism wasn’t managed by systems and realism
Optimism needs a spreadsheet and a backup plan.

89. I ignored shifting market trends and kept pushing
The market doesn’t care about your effort—only value.

90. I didn’t start with the right budget
Underfunding equals underperformance.

91. I didn’t manage expectations—especially of investors and partners
Unspoken expectations are ticking time bombs.

92. I didn’t care about my personal brand early enough
Reputation compounds, for better or worse.

93. I didn’t have proper follow-up structures
Potential dies in silence.

94. I didn’t stop to reflect soon enough
Reflection is not a luxury. It’s a lever.

95. I assumed experience = wisdom
It only does if you pause and extract the lessons.

96. I treated my first businesses like projects, not companies
If you don’t respect it, no one else will.

97. I kept hoping without adapting
Hope is beautiful. Strategy is better.

98. I didn’t build for resilience
When crisis hit, so did collapse.

99. I was reactive, not proactive
Waiting for fire instead of fireproofing.

100. I didn’t treat failure as feedback early enough
Failure isn’t the end. It’s the first draft of success.

Conclusion

These mistakes weren’t just failures—they were expensive lessons that helped shape how I now build better businesses and support founders, clients, and mentees. Most of them happened not out of ignorance, but because I didn’t yet have the experience to know better. That’s why I’m writing—so you don’t have to pay the same tuition to the school of hard knocks.

Over time, I’ll write about each mistake in detail, with examples, what I learned, and what I’d do differently. If you see yourself in any of these, you’re not alone. Keep learning, keep reflecting, and keep building.

Thanks for reading.

—Daoud

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