Startups are Hard. My Tips for Entrepreneurs

Startups are Hard. My Tips for Entrepreneurs

Startups are hard. Like, really hard.

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...

1 Tell a lot of people about your ideas.
I see too many people that are afraid to talk to others about their ideas

"Don't worry about people stealing your idea, worry that no one will care." - Dharmesh Shah

2 Choose an idea you're passionate about.
Life is too short to spend your time building something you don't have a passion for.

3 Build something people want. The Ycombinator maxim is brilliant and words to live by for any maker and entrepreneur.

4 Find out if people want something by interviewing them. 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.

5 When possible, solve your own problem.
It's so much better when you can empathize with your users. Not 100% necessary, but helpful.

6 Tackle hard problems that the world is facing. Please don't build just another Social-Mobile-Local app.

7 Focus on markets that you can dominate early (monopoly).
For more on this, read Peter Thiel's Zero To One book.

8 Know the potential growth markets of your company.
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.

9 Know your strengths and weaknesses as a founder.
Self-awareness is a trait that shows maturity and humility.

10 Find a co-founder with complementary skills.
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?

11 Try to not have more than 3 co-founders.
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.

12 Get accountability early.
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.

13 Pursue advisors and advice from those who have come before you.
Seems obvious, but often times I think it's overlooked and/or undervalued.

14 Read lots of content. Know who the best are.
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.

15 Get really good at googling stuff. 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.

16 Pay attention to your competitors early. 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.

17 Build something. Measure it. Document your Learning. Repeat. 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.

18 Pivot before it's too late if you have not validated your hypothesis. 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.

19 Charge for your product early. 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.

20 Try not to have a marketing budget for as long as possible. 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.

21 Bootstrap if you can for as long as you can. 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.

22 If you have to pursue investment capital, fundraise when you don't need it. 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).

23 Never ask an investor to sign an NDA. 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.

24 Read pitch hacks before you pitch your idea to any investor. 90 or so pages of this e-book by the guys behind Great resource.

25 Don't "pay to pitch". Just seems a shystery thing to me. There's enough opportunities to develop real relationships with investors that this just seems like nonsense IMHO.

26 Raise at least 18-months of runway. Just a rule of thumb. Might consider getting more than 18-months if you can especially in the slowing fundraising environment.

27 Update your investors monthly. Read @Jason's post on Why investor updates are really important.

28 Treat your early customers like they're greek gods or goddessess (concierge service). I believe this was a Paul Graham, Ycombinator maxim about doing things that don't scale at 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.

29 Be radical about customer service. Everyone on the team should take turns through customer support. Keep your users happy.

30 Create a list of KPIs to track (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.

31 Be transparent. Be HOT: Honest, Open, Transparent. Like Buffer.

32 Determine what your one metric that matter's most is and optimize everything for that. 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.

33 Create a live dashboard of your company KPIs and display it prominently. Fun project and something that has both internal team benefits, as well as ease of use when sharing investor updates.

34 Conduct design and development sprints. Just a plug for lean / agile development of ideas and products. Google has some good tips on doing Design sprints.

35 Ship code daily. 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".

36 Carefully craft what type of company culture you want. Some good stories from Airbnb Founder Brian Chesky in Startup Class video 10 and the Stripe Founders in the Startup Class video 11.

37 Spend a lot of time hiring the best people (talent, and cultural fit). 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.

38 Buy said employees cool things; like computers, fitbits, and beer. 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.

39 Remember: Family, Tribe, Village, City when your startup scales: Be advised your processes will break. This I found in the Greylock Partners video on Technology enabled Blitzscaling Lecture 01. Their Greymatter series is a podast / video series of a Stanford course by Reid Hoffman and crew.

40 Don't think you're irreplaceable. You're replaceable and likely will be. The best know when to step down.

41 Say "no", more than you say "yes".
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.

42 Auto email responders. Use them.
The technology deluge can take over your life. Don't let email control you.

43 Delegate, Eliminate, Automate, Liberate. 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.

44 Listen to Tim Ferriss podcasts. 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

45 Pray and/or meditate daily.
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.

46 Fast regularly (food and other things).
It's a discipline that teaches you to deny yourself of the luxury of eating food every meal.

47 Get a gym membership. Go to said gym.
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.

48 Plan ahead and pack your own lunches.
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.

49 Don't pay for office space until you absolutely have to (and when you do, stay cheap).
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.

50 Take time to do things that make you happy.
Take walks! Go to the park. Explore your neighborhood. Treat yourself every Friday to a donut. Live life on the happy side!

51 If you're in a software startup, have a hobby that you use your hands to build something tangible / physical.
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!

52 Never stop learning.
Curiosity is one of the most important traits I think all high performing entrepreneurs have in common.

53 Set goals for yourself and your company. User OKR's. Google does this. Originally introduced I think at Intel, a framework of accountability that works.

54 Use Google sheets and laugh at everyone who still uses Microsoft Word.
I've developed an acute allergic reaction to Microsoft Office. Maybe you have too.

55 Have a list of 3-phrases you want to be able to say one day. 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.

56 Take the effort to build a personal brand. 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.

57 Take time to reflect.
Getting all spiritual on you again, but it's so important to take regular times to review. Reflection and introspection are marks of maturity.

58 Spend quality time with people you love.
No matter how busy you are, and how crazy things are; invest in people. You make time and prioritize what's important.

Don't let the immediate crowd out the important.

59 Wake up early.
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.

60 Wake up at the same time each day.
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.

61 Designate your mornings as "me time".
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.

62 Keep meticulous records. 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.

63 Get outside your comfort zone.
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.

64 Travel. 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.

65 Don't incorporate until you have to. 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.

67 When you do incorporate, do a Delaware C-Corp. Use a service like Clerky. Makes it pretty easy.

68 Listen to audiobooks on 2x speed.
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.

69 Remember, you're not on this journey alone.
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.

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,


UPDATE 3/31: **This post has been made into a sweet slide deck and was chosen by as a top presentation! You can download it from Dropbox My friends at the incredible presentation Award-Winning Design Firm, Empowered Presentations put it together.

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