Entrepreneurs, what are the 3 best pearls of wisdom you've received for your startup ventures?


This is general guidance that you've found is key in achieving success. Can be marketing related, funding, technology, hiring, anything. If you could just pick 3 that you think have held up over time and have had the biggest positive impact in success, what are they? (And please vote for this question if you like it.)

COMPILATION TO DATE (10/29/09) If I combine similar suggestions, the top 3 look like this:

PEOPLE - hire smart people who get things done.

CUSTOMERS - listen to your customers closely.

PRODUCT - Get it out, evolve, iterate quickly and make it great.

And the rest:

YOURSELF - Be passionate and disciplined with a sense of urgency, leading others by your example.

CASH - Spend wisely.

CHANGE - Be flexible for the changes that will occur.

GOALS - Have them.

RISK - Never bet the farm, but do take bigger risks on smaller projects, lesser risks on projects going steadily.


asked Oct 22 '09 at 02:23
4,214 points
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25 Answers

  1. Never bet the farm
  2. Hire people who are smart and get things done (Joel Spolsky coined / popularised this )
  3. Just get on and do stuff
answered Oct 22 '09 at 02:54
Neil Davidson
1,839 points
  • Good points. Definitely having the right people is critical. And then wrapped around it all, get stuff done. Thanks for the thoughts. – Chris 14 years ago


Where to start. Here's everything I've learnt from six months of my first startup.

Any advice you're given, take with a pinch of salt. You learning on your feet is the only really valuable way to learn.

Give a shit. About everything. Your product, your reputation, your fellow founders, your customers. Give a shit some more: if you fail, you should feel terrible. Boy will your friends mock you. That's critical as this way you'll try harder not to fail.

Read The Four Steps to the Epiphany. Now. NOW.

Be cheap, lean and fast. And by that I mean really fast. Someone somewhere else is working on a product that's better than yours in every way, your only way to win is to launch before them. And by cheap I mean really cheap. Seriously, 90% of all startups are neither cheap nor lean.

Outsource stuff that isn't core: analytics, metrics, email, hosting, monitoring, feedback systems, literally everything you can.

Get your proposition awesome and simple. Like, if you can't define what you're doing and why that's valuable in under a paragraph try harder.

Simple is good. Simple revenue models, simple products, simple infrastructure, simple internal nonsense. Simple is more.

If you're raising money take money if you're offered it. Would you rather own 100% of nothing or 75% of something? Are you building a product or are you raising a fund? It's the former, take the money because the opportunity cost is too great to fuck about for six months touching VCs.

Revenue impresses everyone. As does a term sheet.

Know where you'll be in 3 days, 3 months, 1 year and 3 years. Make sure the 3 year goal is to be stomping on a publicly listed company.

Marketing is a black art, I don't think anyone is good at it without having a pre-existing tribe. Solution: start early, communicate with potential users, start the conversation. Look down, are you blogging? If you're not you've stumbled at the first hurdle. Don't bother planning too much for marketing: You'll do better on your feet, focus on product management now.

Product management is hard. Get users. Learn from them. Respect them. See #2.

If you're not a designer keep your UI and design simple.

Respect the UX else I'll stab you. Seriously. I don't care what you're doing, but there should be an emotional attachment to using your stuff. Even if you're a text editor: make the user feel like they're in the zone. AND DON'T CONFUSE UI WITH UX FOR THE LOVE OF GOD. Mac developers usually nail UX. Learn from that.

You'll be told you'll fail, or that people don't want your product, or that you should do something else, or that what you're doing isn't big or valuable enough (trust me, I hear this all the time) -- fuck them. Prove them wrong. You're an entrepreneur (god that word sucks) - if I told you to jump off a bridge would you? so why would you listen to me when I said stop? Prove. Me. Wrong. See #2. That's a force to be reckoned with.

I'll leave you with the most powerful story (I'd love a source, I'm terrible at story telling) I've been told. Ever. :

A few years ago a young girl decided she wanted to swim across the channel. So she did. However a few hours into the swim, she got tired and felt like crap. It was raining and foggy. Miserable. So she called it quits. It turns out she was about 20 minutes swim from the shore, and would have done it in record time. If only she hadn't quit.
My point is, when the going is toughest, and it looks like all the chips are down. They might not be. And imagine how sick you'd feel if you gave up so close to winning?

Oh, and if when you chat to your co-founder you aren't blown away and left with a "whoa." you've probably chosen the wrong dude.

answered Nov 3 '09 at 10:38
744 points
  • Hey, not too much at all! Excellent feedback and I think spot on. – Chris 14 years ago
  • Awesome post pclark. – User1084 14 years ago
  • pclark, you rock! – Sandeep Satavlekar 14 years ago
  • Wheres the option to give more than 1 up-votes.. :) – Dienekes 13 years ago
  • Very wise comment; `Oh and if when you chat to your co-founder you aren't blown away and left with a "whoa." you've probably chosen the wrong dude.` – Carlos 13 years ago
  • @Carlos could someone explain this comment please? I never found anything hard to understand though English isn't my native, I have hard time understanding this. Maybe paraphrase this – Vlakarados 11 years ago

  1. Be very serious about your product.
  2. Be very serious about your customers.
  3. Don't take yourself too seriously.
answered Oct 22 '09 at 04:26
Mark Stephens
976 points
  • Like it a lot. Understanding your customers is probably on my list also. – Chris 14 years ago


  1. Ship as early as possible (minimum features)
  2. Really listen to what your early customers think
  3. Evolve product and iterate (GOTO 1)
answered Oct 22 '09 at 20:06
Denis Hennessy
1,363 points
  • Good points. At one software company I was with we had a mantra of WAR (win all reviews) before shipping. Unfortunately that meant we took too long to ship sometimes and missed windows of opportunity. – Chris 14 years ago
  • Lean start-up principles 101. I love it. – Josh Sam Bob 14 years ago
  • +1 This strategy always proves to be effective when I see it implemented. – Ivan 12 years ago


  1. Don't do anything that you don't need immediately.
  2. Build assets and turn them into competitive advantage.
  3. Take massive risks when starting a small project, avoid them when your project is growing steadily.
answered Oct 22 '09 at 03:45
Arpit Tambi
1,050 points
  • Definitely have to take some risks. Thanks for the feedback. – Chris 14 years ago


The three best pearls of wisdom I received for my startup:

  1. Have flexible optimism for when you need to Zig and Zag. Things change, so be ready to adapt as needed.
  2. Be emphatic to the struggle of other people, especially your staff and customers.
  3. Lead by example. Put yourself out there and take pride (and responsibility) for the good (and bad).
answered Oct 22 '09 at 02:45
Jarie Bolander
11,421 points
  • Good stuff. I'm still working on my list but "things change" is definitely one of them. – Chris 14 years ago
  • I like the second point. It shows that you are a charismatic leader and not only care about the money. – Jpartogi 14 years ago

  1. Only work with or hire A+ players.
  2. Don't raise money unless you really need it.
  3. Get your product to market as quickly and as cheaply as you can.
answered Oct 25 '09 at 01:47
Usman Sheikh
1,728 points
  • You hit two of the top three consensus points. – Chris 14 years ago

  1. Have passion and enthusiasm
  2. Pick the team for the job
  3. Know where you are heading, i.e. Have goals
answered Oct 22 '09 at 08:31
Richard Campos
91 points
  • Definitely spot on. Thanks. – Chris 14 years ago


  1. Bring passion greater than any potential obstacle.
  2. Stay focused and disciplined every day.
  3. Treat everyone exactly the way you want to be treated.
answered Oct 22 '09 at 07:09
Keith De Long
5,091 points
  • Like it a lot! Thanks. – Chris 14 years ago


  1. It's the team - bring people on that get it, that contribute more than they take away, and come to work having thought about the product when they woke up
  2. Cash is king
  3. Keep it simple: If it's too complicated to explain, it's too complicated to buy (even if the inner geek thinks it's the coolest thing in the world).
answered Oct 23 '09 at 22:04
Manuel M
263 points
  • Good feedback. Thanks. – Chris 14 years ago


Hmm, how about 3 pearls of wisdom working for a startup?

  1. Learn from the best around you, so be humble
  2. Learn to be flexible, bend or break
  3. Learn to quit, startups can be pretty crazy, so it's OK to jump ship

And for the rest of it...

  1. Be passionate, it's the only thing that gets you up for the next day
  2. Be responsible
  3. Make all the mistakes, it's OK.
  4. Take care of your health, eat right and exercise
  5. Have a plan, cause you might be on board a train to hell, so don't follow the leader blindly
  6. It is better to work for yourself, get your own startup.


answered Nov 3 '09 at 18:41
Seymour Cakes
166 points
  • I missed this before but definitely good pearls. – Chris 14 years ago
  • These points are awesome. – Aditya Anjoli 12 years ago

  1. Be honest with yourself about your motivations. In the pre-startup phase, for instance, ask yourself why you want to start this business. Encourage your collaborators to do the same soul-searching and share. Make it a habit. Always be willing to go as deep as necessary to reach consensus and thus build a team that is all pulling in the same direction.
  2. Be thrifty. Spend as little as possible to prove your concept. If possible, scrape by until you have built a money engine (i.e. For every dollar you spend doing X, you make two dollars of revenue). Taking on debt or investors is extremely expensive in the long run. It raises the hurdle for survival and reduces your exit possibilities. The longer you can go before asking for money, the better terms you will get. Finally, when you do seek investors, it is magical if you can draw them from your customer base. Doesn't always work, but you're in good shape if you can pull this off.
  3. Release early and release often. Always ask yourself "Would the company be better off if we launched now or if we delayed?" Considering that building a customer base is likely to be your biggest challenge, the answer is probably "Release now and pay close attention to the feedback."
answered Nov 21 '09 at 07:16
831 points
  • Also real good advice. Especially like the "motivations" question. – Chris 14 years ago
  • At one startup, I interviewed a person for an executive position and asked them essentially that. Their answer talked about having a staff of people, corner office and more. Clearly they were the wrong fit. Unfortunately we hired the person and...they turned out to be the wrong fit. So a great point in your answer. – Chris 14 years ago


  1. Don't run out of money.
  2. Don't start a business with someone you have to see on Christmas or you'll be miserable 365 days a year, instead of 364.
  3. Don't hire anyone you can not fire, like a bad business partner or your dad ;)
answered Mar 3 '10 at 16:15
346 points
  • Good points. Definitely cash is king. – Chris 14 years ago

  1. Don't spend time thinking about/trying to raise money. Plan on not getting any. If you can't launch a useful product without it, you wouldn't have gotten it anyway. Spend the time building something awesome.
  2. You'll spend weeks/months coming up with the perfect plan. In 6 months it won't even be recognizable. Be flexible and expect things to change, a LOT. Until you start building and get customer feedback, you're guessing.
  3. Someone else is working on an idea just like yours. If you don't have the expertise to out-execute them, find it. If success is based on being first to market, you're taking a huge risk. Execution should be a daily topic of conversation with yourself - how will you excel?
answered Oct 25 '09 at 06:58
892 points


Lots of answers got rather deep :) I'm going to keep it simple.

  • Q: How do you make a profit, in any business? Or, more appropriately, become profitable quickly?
  • A: You manage your costs.

The best pearl I ever received was not to place even a single employment ad until I had controls, checks and balances well thought out and in place. This may seem (hopefully) like arcane wisdom to many, yet I see so many new companies oblivious to or ignoring this very simple principle.

answered Nov 8 '09 at 00:56
Tim Post
633 points
  • Good advice for sure. I still see startups that get way ahead of themselves and hire too far ahead of revenue. – Chris 14 years ago


(Not sure if I should put here or as a comment to my original question so I'll give this a shot.) If I combine similar suggestions, the top 3 look like this:

PEOPLE - hire smart people who get things done.

CUSTOMERS - listen to your customers closely.

PRODUCT - Get it out, evolve, iterate quickly and make it great.

And the rest:

YOURSELF - Be passionate and disciplined with a sense of urgency, leading others by your example.

CASH - Spend wisely.

CHANGE - Be flexible for the changes that will occur.

GOALS - Have them.

RISK - Never bet the farm, but do take bigger risks on smaller projects, lesser risks on projects going steadily.

Thanks to those who answered. I hope more will. I hope it's interesting for everyone.

answered Oct 30 '09 at 09:05
4,214 points


1) Always be ready to adjust your plan because things will look different in the future than you think today.

2) Work with the right people who know how to adjust the plan and know how to succeed.

3) Have a sense of urgency whether you're working at a big public company or a small startup.

answered Oct 25 '09 at 00:30
61 points
  • Agree 100%. A sense of urgency is another trait I often see missing but is so critical. – Chris 14 years ago

  1. Manage cash - make it your top priority - my last company went into Q408 with a profitable quarter and more than 20 weeks of cash in the bank - we were able to keep our level of investment constant and came out stronger in Q209 because of it.
  2. Hire people who are smarter and more successful than you - the old adage A players hire A players, B players hire C players is so true and can really destroy any forward moment you've managed to create in your company. Watch out for this during your critical "high growth" stage.
  3. Pick your investors for the experience they bring and the help they can give you - not just for their deep pockets or favorable valuation.
answered Nov 21 '09 at 00:45
Rs Holman
596 points
  • Great points. The "people" point has come out loud and clear throughout responses on this. And the experience of investors is a great point too. I've actually created an advisory board for my current company that's been extremely helpful. – Chris 14 years ago


Beautiful compilation. Good job.

I would simply modify "hire smart people who get things done" for "hire people smarter than you and who get things done".

Also, considering that cash flow is the Achilles' heel of every startup, I would add: Cash is king so manage it VERY carefully.

answered Nov 26 '09 at 04:01
A. Garcia
1,601 points


Yourself: Understand that being a startup means taking risks, being open minded, listening to others, being flexible

Financing: Whether you Bootstrap or take on some debt make sure you its reasonable amount in case you fail (don't want to put yourself into personal bankruptcy). Try not to sign personal guarantees for loans. Find as much unsecured money as possible

Product: You don't need to build the Taj Mahal to go to market just a functional prototype

answered Apr 24 '10 at 05:16
484 points


My simple wisdom: To get product done, work every day. Small things add up.

answered Apr 24 '10 at 16:44
2,288 points

  • Create a plan and FREQUENTLY review it with your team. When you review it, either adjust what you're doing or adjust what your plan says.
  • One of the really, really great ways to do this is to read the book "Mastering the Rockefeller Habits: What You Must Do to Increase the Value of Your Growing Firm" by Verne Harnish. Master the use of the one-page strategic plan in that book and you'll be off to a better start than many firms. It's not a quick cure, it's hard work, but it pays off.
answered Mar 10 '10 at 11:10
433 points

  • Have adequate cash flow
  • Work with good people
  • Make sure you have focus
answered Jan 11 '10 at 13:34
Christopher Mengel
89 points

  1. Never have debt, ever. It reduces your future options and will eventually have you doing work that will not advance the company's agenda just to pay the bills.
  2. The client knows the pain and need, the salesman knows what the client needs (sort of) and the engineer will know what is possible. Get them all in the same room during early stages
  3. Part of what you sell is knowing how to work with particular clients. Try expanding your scope of what you provide your best clients - no one else can match the delivery, even if there are similar products in the marketplace.
answered Oct 29 '09 at 21:05
Steve French
621 points


I've been in software development for 20 years now. Last 10 in management roles before I started my own startup. You know what I learned?

There are ideas and there's execution. We all have ideas. Ideas are cheap, but few of us can really execute and when it comes to execution -- It's 90% people. So, get good people. Not the ones that talk and talk endlessly. Not the ones who are there to pass time, not those who obsess about ergonomic chairs for their sore butts, or the latest LED technology for their aching eyes and brains or the ones who will run out in the middle of the day to buy the latest mouse and expense it cause they just gotta have it or those who come at 11am and claim to be working till 9pm, only to leave at 6:30 or people whose lives are full of drama that boils down into "why they can't be there today". Don't hire those who gather a crowd around them every 20 minutes to discuss the latest xkcd. Don't hire the ones who constantly complain and find reasons why "this cannot be done" and marvel at the beauty of the reasons they found for failure. Don't hire pessimists or cynics - they will infect the rest. Get people who can get it done without complaining, without looking for reasons to fail before they started. Those who say things "can be done". Those who find ways even if it means working hard and being creative. Get people who can execute. Startup is no place for non-performers. They will drown your ship. Guaranteed.

answered Jun 15 '11 at 03:53
Ron M.
4,224 points

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