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101 things I learned by launching 3 failed startups (and 1 successful one)

Starting a business is thankless, hard, complicated, and filled with pot holes you’re bound to run into. Coaches and gurus tell you one thing, while investors and influencers tell you the exact opposite. Friends doubt you, family assumes you’re fine, when in reality you probably feel dumb, trapped, and (at times) completely hopeless.

If you have a family that depends on you, that adds a completely new level of stress that younger founders will never know about until they have kids of their own.

I say all that to say, I get it. I’ve been there. And I’ve failed 3 times, and had 1 successful business. I’m not saying I’m an expert, but if any of what I learned in the last 6 or 7 years can be helpful, I have no problem flaunting my failures for others to learn from.

So without further ado, here are 101 things I learned (that hopefully help you)

  1. Don’t look for an out before you start: If you’re starting something with the intention of a quick flip, odds are you wont last. Not saying it’s a guaranteed failure, but it’s rare to see these types of founders last in their startup beyond 2 years.
  2. It’s gotta be your life’s mission: Arlan Hamilton said it best – if you can’t imagine a world where this business doesn’t exist, you should probably start it. You’ll need that motivation for the hard times.
  3. It’s ok for your life’s mission to change: Look, life changes, and so do you. That’s ok. It’s also ok for your business’s mission to change. Or for your mission to change. Don’t beat yourself up.
  4. Don’t. Pay. Your. Cofounders: Don’t pay your co-founders out of your own pocket, and make sure when you pay them, it’s from the company, not from you. Otherwise it sets up a weird dynamic. You all need to be yoked together.
  5. You and your partners need to all feel equally yoked: Or at least proportionally yoked based on your compensation. The fastest way to burn out is giving more than you’re receiving.
  6. If you feel belittled as the CEO, fire them: This is YOUR company. YOUR vision. YOU are in control.
  7. You’ll probably never become Mark Zuckerberg. Be ok with that: Yes, never tell you the odds! I get it. But also be comfortable with failing, if that’s what you’re really shooting for. It’ll take the pressure off, and honestly probably help you achieve more.
  8. Protect your culture at all costs. Be ruthless: This is one that I had to learn the hard way. Seriously, be ruthless about it. Protect that as if it were your first born child. It’s the most delicate and important aspect to a thriving business.
  9. Encourage and uplift. Always: There have been studies on this. Machiavellian management never works long term.  
  10. Always use the compliment sandwich: Compliment, criticism, compliment.
  11. Be clear in your vision: When communicating to employees, you need to be sure. You’re the captain. 
  12. But it’s also ok to be unclear in your vision (privately): You can’t predict the future. Sometimes wishful manifesting is the best you can do. That’s ok.
  13. Be vulnerable as a brand: People resonate with vulnerability. If you’re a first time CEO, own it. People want to be part of the journey.
  14. Network and don’t be afraid to show your newbness: Entrepreneurship has one of the most welcoming and encouraging cultures I’ve ever found.
  15. Keep talking to people. No matter what: Take meetings even if they don’t develop into a sale. Developing a network will pay dividends over time.
  16. Advice is necessary: But make sure to get it from the right people. 
  17. Find advisors who are uplifting, been there, and brutally honest: Don’t get a life coach. Business coaches can work, but it’s hard to find the right ones. Instead, DM entrepreneurs you look up to. They’re happy to share and help 99% of the time.
  18. Don’t be prideful: You don’t know what you’re doing. Even as a serial entrepreneur, I’m making it up as I go along.  
  19. Entitlement will kill you: You’re not owed anything in startup world. As Mac Conwell says, “No body cares. Work harder.”
  20. There’s always a way to succeed: You just need to find it. 
  21. You also need to know your limits: It’s ok to take a break. You don’t need to “grind” you need to sleep. And eat a snack.  
  22. Don’t get emotionally attached to your product(s): It kills innovation
  23. Know what your market wants at all times: How? Talk to your customers. Frequently.
  24. Recognize when your market wants changes: Keep your ear to the ground. Get into groups, follow customers and ideal clients online.  
  25. You’re going to feel like you’re losing and everyone else and their mother is winning: That’s normal. Don’t let it frustrate you. 
  26. You’re doing way better than you think you are: No, seriously. You are.
  27. Google everything: All the info you need is online and free. 
  28. Follow the right people online: This is huge. Make sure you’re taking in healthy content that uplifts and energizes you.
  29. Even though there’s no real degree for entrepreneurship, there are textbooks: Lost and Founder, Startup Owner’s Manual, Lean Startup to name a few.
  30. Establish yourself online through SEO: Use Google My Business if you’re a local company, and above all else make sure you rank for your brand
  31. I hate PR. But PR’s a thing: Couple of tips:
    1. Secretly apply for awards, even if they’re stupid. It helps boost morale if you win them. 
    2. Use it as a pleasant surprise for your team to validate them and make them feel others appreciate them. 
    3. Figure out a PR strategy to get your name out there. It’ll help lessen the load on outbound sales
  32. Have a support group: Have someone to talk to. 
  33. Don’t EVER develop the mentality of “what’s in it for me”: It’s the fastest way to startup death. Advisors, VC’s, brand evangelists will all sniff you out. 
  34. Help other entrepreneurs out: Good karma is never a bad thing. Work together. If there’s an opportunity for a partnership and it’s a good fit, take it. 
  35. Be organized and efficient with your time: Sometimes you need more hours in the day. Find micro-moments to get small stuff done – social media posts, emails, comments, phone calls, etc. 
  36. Take breaks: You can’t burn out. You need mental breaks. Don’t feel guilty for taking 30 minutes for yourself to clear your head. 
  37. If you feel overwhelmed, welcome to the club: But also take a break. 
  38. It’s ok to enjoy your Friday nights: Don’t be a slave to your startup. It’s a marathon, so you need to make time in your life for what you enjoy. Or you’ll burn out. 
  39. Take care of your nutrition: Stress eating is a thing. And it just makes me more stressed. Downward spiral. 
  40. Exercise: Even if it’s walks. Not taking care of your physical well being takes a toll on your mental well being, which takes a toll on your startup
  41. Mental breakdowns are ok: You’re not alone. It’s stressful. It can suck. And it can feel like no one is helping you or even likes you. You’re not alone. Reach out for help when these moments come. 
  42. If you have a family, know their limits: Kids need your attention. Wives and husbands need your attention.
  43. Make time for date night: Keeping the romance alive is important. They’re your #1 advocate. So give them a little for all their sacrifices for you.
  44. Make time for family night: That’s who you’re doing this for anyway.
  45. Sleep: You need 6-8 hours of sleep a night. Don’t go below 5 more than once a week if you can help it. 
  46. Make sure all co-founders are on the same page: And communicate similarly!
  47. Content communication: Make sure everyone says what they mean. You don’t have time for trying to interpret what someone is actually saying instead of just saying it 
  48. Over share: Don’t leave room for misinterpretation. You don’t have time for that. 
  49. Make sure you know what each co-founder’s runway is: Some may have a ton of kids, others may not have any family to care for. Knowing their runway lets you know how long someone can go before needing to get paid.
  50. If you’re bootstrapping, your first goal needs to be getting profitable: Like ASAP
  51. It’s ok not to get funding: Most businesses don’t. And unless you’re looking to scale monstrously, you probably don’t need it.
  52. It’s ok to get funding: If you want to build a rocket, do it. Just understand the tradeoffs.
  53. Learn how to do it yourself before telling someone else what to do: This makes it clearer for your employee, and it helps you keep them accountable. they can’t BS you.
  54. Don’t start with a c-corp: There’s a lot of complications with a C-Corp. Unless you’re looking to get funding from VCs, it’s probably not the smartest tax decision.
  55. Just don’t do a c-corp: Seriously. Unless you’re 100% getting funding. 
  56. Wyoming and Delaware are the states to incorporate from: If you’re going C-Corp. There’s a lot of legal precedent there, meaning those states have already figured it out. (And VCs want you to incorporate in Delaware for that reason).
  57. You can use 2 LLC’s – one to house your IP and one to use it: This keeps you from getting hung up if there’s an IP lawsuit. They can’t go after the IP AND the business at the same time.
  58. Trademark and copyright what you can: It’s important to protect what you can.
  59. Apply for patent-pending when applicable: Until you can actually patent it, at least get a provisional patent.
  60. Use services like RocketLawyer or legalzoom: Save some cash where you can, but also don’t scrimp on cheap lawyers.
  61. Always consult a lawyer: Seriously, they make all the difference.
  62. Make sure you have an NDA: Most VCs won’t sign one, and honestly you want them talking to their network about you anyways. But for vendors, it’s important.
  63. Make sure you have a contract in place for each employee: Including yourself and your co-founders.
  64. Make sure to vest you and your partners’ equity: This protects you and your company if y’all split up.
  65. Make sure your equity vests at 100% during a liquidation event: Get all your money.
  66. Accelerators are great first steps: And there’s tons of them.
  67. Validate your idea: Especially before investing any money into it, let alone time.
  68. Make sure to have a solid business plan: And go super niche to start!
  69. Do your research: Assumptions will kill you, so minimize them as much as possible.
  70. Make sure you know your real target market: And the actual market size.
  71. Digital marketing is an important thing to invest in early in a startup: Especially SEO, if you want long term, sustainable growth.
  72. Understand what your brand and feel is: Again go super niche.
  73. Make sure to frequently do a SWOT analysis: It’s important to know new competitors and be honest with your weaknesses.
  74. The world is a big place: Competition is a good thing. 
  75. Don’t get intimidated by competition: There’s enough food for everyone to eat.  
  76. Success comes from scaling the unscalable: Customer service, sales, hustle – customers care if you care about them and you bring them outstanding value
  77. You and your co-founders need to talk everyday: Easiest way to do that is by being in the same area. Remote is hard for starting out and takes a lot of discipline that most just don’t have starting out.
  78. Get a personal CPA: Taxes suck and are complicated for entrepreneurs.
  79. Document what you learn as you go: You’ll thank me.
  80. Build your brand even before you have a product: If you want your product launch to go off with a great start, you need an audience.
  81. No matter what you’re selling, you’re a brand first: Every startup is a media company first.
  82. Learn to code: Not so you make it yourself, but so you can hold your devs accountable. And also understand their challenges and how to help them when necessary.
  83. Learn the basics of finance: At the end of the day, money is your lifeblood.
  84. Learn how to project revenue: This will help you when making future plans
  85. But don’t spend all your time on revenue projections: You’re just guessing anyways. 
  86. Focus all your energy on being profitable: If the 2022 market correction has taught us anything, it’s that a profitable business is stable and will last through turbulent times. A startup relying on hype will not.
  87. Develop fast, develop right: Don’t take forever to launch. But do measure twice and cut once.
  88. Plan out your development: Don’t be reactionary. Make sure you have a roadmap, and be disciplined in sticking with it.
  89. Don’t recreate the wheel: Especially 3 times like I did. Take advantage of open source and no code options.
  90. Don’t let your leads go cold: It’s the hardest thing to re-engage cold leads. Keep them warm, even if it’s just a monthly check in.
  91. Email marketing will save your leads: AKA monthly check ins.
  92. Find customers who will brainstorm with you: They’re your best customers and your new brand ambassadors (if you treat them right)
  93. Welcome criticism of your product, business model, and leadership: But never of you personally. 
  94. Going solo is hard, but it’s easier than picking the wrong partner: Trust me, did that a few times, and it’s cost me dearly (it killed one business and cost me significant equity in another).
  95. Know thyself : AKA lean into your strengths
  96. Understand not just your weaknesses – but things you dislike doing: Then hire people to help with them
  97. You can outsource your work: Just make sure you get what you pay for
  98. Don’t push your negative energy onto other people: If you’re stressed, don’t take it out on your team, family, or anyone else. That’ll ruin relationships, company culture, and you’re still stressed.
  99. Make time to reflect: Or you’ll never learn
  100. Find your anchor: Could be religion, church, a hike, yoga, sunsets, working out, friends, whatever. But find something that re-energizes you and refreshes you.
  101. Remember why you started: Do you still feel that way? If so, keep going.

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Picture of Jack Treseler

Jack Treseler

Jack is a serial entrepreneur with a decade of experience in marketing finance brands. Jack believes investing and business can be used for good, and loves helping fintech companies scale their business (and their revenue). He's also a fan of pineapple on pizza, but we won't hold that against him.