Startups are Hard. Like, Really Hard. @luketucker

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This list is more or less a curation of tips I've surfaced from my reading or research and from what I've observed from being around some incredible investors and successful entrepreneurs. Note, this advice is geared towards ideation through product-market fit level startups, but the life tips are universally applicable I would say.

When possible, I tried to make the tip "actionable", which I define as something that's able to be done;
or an action having practical value.

So, in no particular order, I give you the Startup and Life Tips for Entrepreneurs: a Journal of Thoughts...

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  • Inspirational.. Thank you
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  • Njce! Thanks for sharing.
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  • thank you! start-ups ARE hard but very fulfilling. i think every working person should venture out into this, at least once in their life. very comforting to know i'm not alone and thanks for sharing your "crumbs". :) rock on and prosper!
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Startups are Hard. Like, Really Hard. @luketucker

  1. Startups Like,reallyhard. arehard. 69 Startup and Life Tips for Entrepreneurs @luketucker
  2. This list is more or less a curation of tips I've surfaced from my reading or research and from what I've observed from being around some incredible investors and successful entrepreneurs. Note, this advice is geared towards ideation through product-market fit level startups, but the life tips are universally applicable I would say. When possible, I tried to make the tip "actionable", which I define as something that's able to be done; or an action having practical value. So, in no particular order, I give you the Startup and Life Tips for Entrepreneurs: a Journal of Thoughts...
  3. 1Tellalotofpeople aboutyourideas. I see too many people that are afraid to talk to others about their ideas.
  4. "Don'tworryaboutpeoplestealing youridea,worrythatnoonewillcare." - Dharmesh Shah
  5. 2Chooseanideayou'repassionateabout. Life is too short to spend your time building something you don't have a passion for.
  6. The Ycombinator maxim is brilliant and words to live by for any maker and entrepreneur. 3Buildsomethingpeoplewant.
  7. 4Findoutifpeople wantsomethingby interviewingthem. Not a novel idea anymore, but the lesson is don't just stop at the initial interviews. Ash Maurya talks in his book Running Lean about the whole lifecycle of interviews.Also, use a tool like Intercom to keep a regular dialogue going with your customers.
  8. It's so much better when you can empathize with your users. Not 100% necessary, but helpful. 5Whenpossible, solveyour ownproblem.
  9. 6Tacklehardproblems thattheworldisfacing. Please don't build just another Social-Mobile-Local app.
  10. For more on this, read Peter Thiel's Zero To One book. 7Focusonmarkets thatyoucandominate early(monopoly).
  11. 8Knowthepotential growthmarkets ofyourcompany. You should be the expert of your market. Show off big picture thinking and make sure "the juice is worth the squeeze" both for your time and your potential investors capital.
  12. Self-awareness is a trait that shows maturity and humility. 9Knowyour strengthsand weaknesses asafounder.
  13. 10Findaco-founderwith complementaryskills. Kind of obvious, but once you know your weaknesses, choose someone that has a strength in that area. The big lesson is: choose your co- founder(s) wisely because you'll be spending a whole lot of time together: do the 6-hour road trip test: can you stand being in the car with someone for 6-hrs?
  14. You can have "too many cooks in the kitchen" and too many shares spread across the large founder group making it harder for a sizable return. This is not a hard and fast rule, but from what I hear from seasoned investors 4+ is problematic, 1 is a basic non-starter but can be done at least at the beginning. 11Trytonothavemore than3co-founders.
  15. 12Getaccountabilityearly. Noah Kagan recommends setting a goal and emailing a friend every day to benchmark your efforts and maintain social motivation and pride to Get Stuff Done. He did this with his friend Neville Medhora as discussed in the #coconog webinar this past holiday season.
  16. Seems obvious, but often times I think it's overlooked and/or undervalued. 13Pursueadvisorsand advicefromthosewho havecomebeforeyou.
  17. 14Readlotsofcontent. Knowwhothebestare. Curation is king. Knowing where resources can be found and having "a guy" (or gal for that matter), who are specialists or mavens in an area is smart. Conscious ignorance of certain things to save space and retain focus.
  18. Someone is building what you are building, you probably just don't know it. It's shocking how little people actually spend searching for information on their idea or company. They assume that if they've never heard of it, it can't be that big. Don't be that guy. 15Getreallygood atgooglingstuff.
  19. 16Payattentiontoyour competitorsearly. They impact your customers. I think this is more true today than maybe 5 years ago. Hiten Shah recently talked about this in a 20 Minute VC episode as well. The ease of which people can launch software now, means competition can crop up real quick.
  20. It's called the lean startup methodology, you may have heard of it: applying the scientific method to startups. Instead of bunsen burners and beakers in a lab; markets and customers are subject to testing as well. This advice is applicable at any stage of a company as scrum and agile deployments (micro projects and teams) statistically outperform bloated, waterfall developments. 17 Build something. Measure it. DocumentyourLearning.Repeat.
  21. 18Pivotbeforeit's toolateifyouhavenot validatedyourhypothesis. Set go/no-go criteria for testing. Can't over emphasize that you should make go/no-go criteria. Not an arbitrary number, but have some discipline and awareness to cut your losses if certain benchmarks aren't set.
  22. Best way to see if someone really wants to use your product is to ask them for money. If they're willing to pay, others will be as well and you're on to something. This de-risks the idea and development investment cost. 19Chargeforyour productearly.
  23. 20.Trynottohaveamarketing budgetforaslongaspossible. Do your best to let the product speak for itself. Focus your time on finding the online communities where your customers hangout and be a contributing member of those communities. Then reach out to patronage opinion leaders who have a following to try out your product, you can be a blog first company too (like these guys). So much "free" and unpaid efforts that can have high return. And of course, focus on building a bomb diggity product! Because if you don't have that right, no amount of marketing gasoline will help; it will just burn cash.
  24. Control your own destiny, utilize revenue to grow your business. Shows you have a real business. Gives you leverage as the entrepreneur. Ultimately it can come down to what your goals are and how fast you want to grow. In order to grow fast, you'll probably need to take outside investment. But a lifestyle business can be a beautiful thing. 21.Bootstrapifyoucan foraslongasyoucan.
  25. 22Ifyouhavetopursueinvestment capital,fundraisewhenyoudon'tneedit. Ideally, you have the leverage when your company is doing well and you don't need the cash now, but you want the infusion of capital to grow and penetrate new markets. Get 18+ months of runway when you do raise (see #26).
  26. Investors see too many deals and are in no way interested in having to sign an NDA to have a conversation about your business.At some point,NDA's may come into play but definitely not in the initial conversations. Just shows naivete and is a red flag. 23Neveraskan investortosignanNDA.
  27. 24Readpitchhacks beforeyoupitchyour ideatoanyinvestor. 90 or so pages of this e-book by the guys behind Angel.co. Great resource.
  28. Just seems a shystery thing to me. There's enough opportunities to develop real relationships with investors that this just seems like nonsense IMHO. 25Don't"paytopitch".
  29. 26Raiseatleast18-monthsofrunway. Just a rule of thumb. Might consider getting more than 18-months if you can especially in the slowing fundraising environment.
  30. Read @Jason's post on Why investor updates are really important. 27Updateyour investorsmonthly.
  31. 28Treatyourearly customerslikethey're greekgodsorgoddesses (conciergeservice). I believe this was a Paul Graham, Ycombinator maxim about doing things that don't scale a the beginning of your startup. These early adopters are probably fringe users anyhow, so treat them well as they're taking a chance on you.
  32. Everyone on the team should take turns through customer support. Keep your users happy. 29Beradicalabout customerservice.
  33. 30CreatealistofKPIstotrack (remember,accountability). What gets measured gets managed is the old saying. How do you measure success and keep accountability? Data and numbers that will meaningfully drive your business forward and can tell you right away the health of your business at any given point in time. There's leading indicators and lagging indicators. Know the difference between the two and make sure you're KPI's are a short list at the beginning, not a spaghetti on the wall approach.
  34. Be HOT: Honest, Open, Transparent. Like Buffer. 31Betransparent.
  35. 32Determinewhatyour onemetricthatmatter's mostisandoptimize everythingforthat. The authors of Lean Analytics preach this hard and I'm a believer. It forces focus, and keeps that beacon of light for everyone to drive efforts towards.
  36. Fun project and something that has both internal team benefits, as well as ease of use when sharing investor updates. 33Createalivedashboard ofyourcompanyKPIsand displayitprominently.
  37. 34Conductdesignand developmentsprints. Just a plug for lean / agile development of ideas and products. Google has some good tips on doing Design sprints.
  38. Or maybe this is better put by Buffer when they say in their core values "You ship code immediately when what you have is better than what's live". 35Shipcodedaily.
  39. 36Carefullycraft whattypeofcompany cultureyouwant. Some good stories from Airbnb Founder Brian Chesky in Startup Class video 10 and the Stripe Founders in the Startup Class video 11.
  40. Early employees are like your co-founders / owners and are taking risks to join you. They should believe in your vision and be aligned with the founders. 37Spendalotoftimehiringthebest people(talent,andculturalfit).
  41. 38Buysaidemployeescoolthings; likecomputers,fitbits,andbeer. Make people feel a part of the team, something greater than themselves with purpose and value. And, cool swag and free stuff is the icing on the cake. In short, make them feel special.
  42. This I found in the Greylock Partners video on Technology enabled Blitzscaling Lecture 01. Their Greymatter series is a podcast / video series of a Stanford course by Reid Hoffman and crew. 39Remember:Family,Tribe,Village, Citywhenyourstartupscales: Beadvisedyourprocesseswillbreak.
  43. You're replaceable and likely will be. The best know when to step down. 40Don'tthink you'reirreplaceable.
  44. Success in life will be determined more by what you say no to, rather than what you say yes to. A maxim my father taught me. 41Say"no",more thanyousay"yes".
  45. 42Autoemailresponders.Usethem. The technology deluge can take over your life. Don't let email control you.
  46. Tim Ferriss has a good recipe for being efficient and doing more with less. Read his book. Despite it's over-marketed hype, it's very tactful and practical and Tim's got a bigger vision at play when you look at all the things he's got going on. 43Delegate,Eliminate, Automate,Liberate.
  47. 44.ListentoTim Ferrisspodcasts. Probably at the top of his game in terms of value and quality in his long-form interviews. Just plugging it because I get a lot of value from it. I'm a big Tim fan if you can't tell. #mancrush
  48. The ancients did it. The top performers do it. You should do it. A brief philosophical point: I see prayer as a "checking in for duty" with the Lord, not a laundry list of what He needs to do for me. The Christian perspective on prayer in some sense I see is seen in the apostle Paul when he says, "I die daily". Another scripture says "Humble yourself in the sight of the Lord and He will lift you up." Prayer inherently is a humble activity and an emptying of your heart to the Lord so that he may fill you with his Holy Spirit. There's a mindset that you should "pray without ceasing", which is another Scripture. But purposeful time set apart is what I'm talking about here. Meditation, on the other hand, I see as emptying yourself of distractions through incantations, practices, etc. I'm of the opinion, both have a place, when employed with the right heart and perspective. More to come on this in another post. Ok... moving on. 45Prayand/ormeditatedaily.
  49. It's a discipline that teaches you to deny yourself of the luxury of eating food every meal. 46Fastregularly(foodandotherthings).
  50. 47Getagymmembership. Gotosaidgym. Basically this whole section is about taking care of your mind, body, and spirit. Prioritize! My priorities I distill down to: Faith, Family, Fitness, Friends, Finances, Fun.
  51. It saves money and will make you eat healthier. Eat your lunch outside, weather permitting. Or you can work for a startup that has bomb lunch plans and a gourmet chef, that works too. 48Planaheadand packyourownlunches.
  52. Hire people for their talent and passion for your company. Give them a beautiful and inspiring place to work, but don't make it such a point with the management team in the early days that it's distracting and detracting. Design of an office can be additive and highly relevant to how your culture is. Make it reflect that, but don't spend $1,000 on the perfect stools for the kitchen. I heard a story that Amazon took old doors and put them on work benches. That's scrappy and awesome. 49Don'tpayforofficespace untilyouabsolutelyhaveto (andwhenyoudo,staycheap).
  53. 50Taketimeto dothingsthat makeyouhappy. Take walks! Go to the park. Explore your neighborhood. Treat yourself every Friday to a donut. Live life on the happy side!
  54. Just something I've heard over and over that it's very gratifying to have a physical thing that you've created. Near immediate gratification / sense of accomplishment. Oddly enough, I think those in the ministry or psychology are similar. They work on building people and sometimes you don't see progress at all so it can be frustrating. But hey, I built that lego train set today with my own hands! 51Ifyou'reinasoftwarestartup, haveahobbythatyouuseyourhands tobuildsomethingtangible/physical.
  55. 52Neverstoplearning. Curiosity is one of the most important traits I think all high performing entrepreneurs have in common.
  56. User OKR's. Google does this. Originally introduced I think at Intel, a framework of accountability that works. 53Setgoalsfor yourselfand yourcompany.
  57. 54UseGooglesheets andlaughateveryone whostilluses MicrosoftWord. I've developed an acute allergic reaction to Microsoft Office. Maybe you have too.
  58. For instance, "I'm going to work out of the Tokyo office this week". Which is a personal favorite of mine, and was originally quoted by Phil Libin, CEO of Evernote on a TWIST episode. 55Havealistof3- phrasesyouwantto beabletosayoneday.
  59. 56Taketheeffortto buildapersonalbrand. It will be more important than you realize. This is just a general tip. It shouldn't be an over-emphasis, I just see it as a must for any workers in this day and age. You don't have to actively do the over the top branding, just own a web presence that you can show the world who you are.
  60. Getting all spiritual on you again, but it's so important to take regular times to review. Reflection and introspection are marks of maturity. 57Taketimetoreflect.
  61. 58 Spend quality time withpeopleyoulove. No matter how busy you are, and how crazy things are; invest in people. You make time and prioritize what's important.
  62. “Don'tlettheimmediate crowdouttheimportant.”
  63. I've been reading in Joshua in the Bible recently, and in like 5 chapters there's literally half a dozen references to "And Joshua arose early in the morning". Look at most successful people: they get up early. Now, you may say that you work best at night - and that's fine, again this is a general piece of advice. It also has to do with the principle of "first fruits" which I won't get into here but maybe at a later date. 59Wakeupearly.
  64. 60Wakeupatthe sametimeeachday. We are creatures of habit, develop a routine and stick to it. Test out different times and habits to see what works best for you. Iterate your life just like you iterate your product.
  65. Get stuff done that's individually important to you. I don't check email until after I've read my Bible and prayed. I'm trying to write more in the mornings. I would venture to say almost every daily blogger / vlogger does this. 61Designateyour morningsas"metime".
  66. 62Keepmeticulousrecords. It will pay off. Setting up processes and structures both in personal and professional record keeping will make your life so much easier when tax season rolls around or for those times when you need to find that one invoice. Easier said then done, for sure.
  67. Both personally and as a company! If you're not slightly uncomfortable and scared at what you're doing, then you are not pushing the boundaries and getting outside your comfort zone enough. 63Getoutsideyour comfortzone.
  68. 64Travel. Ah, Venice! Travel provides perspective and stories. Irreplaceable, really. Now, there is a time and season so don't go galavanting to conferences or on a 4- week trip through South America right before a big product launch.
  69. By incorporate, I mean as a business. It's such a small thing, just do it right, and don't rush it though. When you take investment, you'll have to incorporate and you'll need to do it regardless at some point for legal and practical purposes but don't rush to do all the paperwork when you should be building an MVP and proving if your idea should be a company at all. 65Don'tincorporate untilyouhavetoo.
  70. 67Whenyoudoincorporate, doaDelawareC-Corp. Use a service like Clerky. Makes it pretty easy.
  71. I listen to lots of podcasts and talk to high performers. Almost to the man, they all do the 2x audiobook speed and most of their content is being read to them through the illustrious ear buds. 68Listento audiobooks on2xspeed.
  72. 69Remember,you'renot onthisjourneyalone. Entrepreneurship and founding a company can be lonely. Keep in mind many others have gone through or are going through similar experiences as you. Find a tribe and keep your sanity.
  73. This list is more of a running note pad of things that I've seen, heard, read, or observed. It's in no way meant to be me preaching as I don't have the soap box to do so, but as I've said before I hope my blog can be a resource - One beggar telling another beggar where they found food. So, here's 69 morsels of bread that I've found. Go forth and prosper. Until next time, @LukeTucker - Sultan Ventures, CEO Aloha Squared
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