Five years ago I was re-doing my last year of high school, managing a retail store full-time and performing in a play five nights a week. Suffice to say I burned out pretty quickly and in hindsight I can see why.

Hindsight is a grand thing, but we don’t all go through the same experiences, so the hindsight of others can be beneficial to us as well. These 13 successful entrepreneurs and startupers have some great stories to tell, and I thought asking what they wish they knew five years ago would be a great way to find out what advice they have that could benefit us now.

Soraya“It’s a marathon, not a sprint” – Soraya Darabi

I wish I knew five years ago what people have been telling me for decades: life, and most everything, is a marathon, not a race.

Soraya Darabi is a Co-Founder of Foodspotting and ZADY


brian“I wish I was more sure about content marketing” – Brian Clark

Five years ago we made a bet on the term “content marketing,” which is what Copyblogger had been talking about all along without the terminology. That turned out to be a good bet, but I wish I had known how much the industry would explode. Maybe I would have done things differently, maybe not, but being absolutely sure that a billion-dollar industry was being born would have certainly made the bad days easier to get through.

Brian Clark is the CEO of Copyblogger Media


nate“Innovation is simpler than you think” – Nate Kontny

Most of us are stuck thinking innovation is gathering creative geniuses in a room and brainstorming what life will be like in 10 years. You might come up with something impressive, but you’re going to build something no one has any use for.

I wish someone had told me 5 years ago how simple innovation can be: study a task someone has, break it out into its individual steps, eliminate as many steps as possible.

OXO innovates on household items we take for granted like measuring cups. As they watched real people fill up a traditional measuring cup, they saw one of the steps we have is this awkward bending over to see how much liquid was actually in the cup. We’ll do this four or five times trying to get an accurate amount. Innovation was eliminating the awkward bend. They added the measuring cup’s ruler at an angle so you can read from the top. Simple, but only discovered because they spent the time intently watching the steps people took to get a task done and removed one. They sold a couple million of those measuring cups in the first 18 months.

Nate Kontny is the Founder of Draft


gary“You can’t be everything for everyone” – Gary Swart

I wish I had known that even the best team with the best product will fail if the target market is not big enough to support pervasive adoption. And after you think big, I’ve learned you have to think small—a company must choose one or two concrete problems to solve and then solve them brilliantly, because a business will never be successful if it tries to be all things to all people.

Gary Swart is the CEO of oDesk


dan_martell“Building a billion-dollar busines starts with a decision” – Dan Martell

I wish I knew that the only different between building a $500K dollar business vs. $10M is deciding. It’s that simple. It doesn’t require more time, more intellegence or more know how. It only requires that you decided up front to set that goal, and every decision you made was aligned with that goal Can it be that simple? Trust me, it is.

Dan Martell is the Founder of


jay“You should know about photos and videos” – Jay Baer

Five years ago, I wish I knew how quickly our preferred communication mode would shift from the written word, to photos and videos. Today, if you’re in social media and/or content marketing, a working knowledge of photo and video composition and editing is almost a requirement.

Jay Baer is a social media and content marketing strategist at Convince and Convert and best-selling author of Youtility


kristi“Think about branding early” – Kristi Hines

One thing I wish I knew when I got started with blogging and building my online presence was that down the road, I would want everything to be branded under my name as opposed to a nickname. Even now, I have to introduce myself twice – once as Kristi Hines, and then when I get the blank stare, again as Kikolani. It’s getting better now that I’m doing a lot of freelance writing under my real name, but there are still times that people only recognize me by my blog name.

Kristi Hines is a freelance writer at Kikolani and runs The Ultimate Course in Blog Post Promotion


adii“Build a mailing list from the beginning” – Adii Pienaar

I’ve being blogging and writing since I started in my first business WooThemes. But one of my biggest mistakes was not building a mailing list from the start. It was something that I thought ‘Internet marketers’ did but I didn’t seize the opportunity to speak directly with my readers in my blog. For anyone starting out as a writer, my advice would be to knock up a simple sign up form and start building your mailing list now.

Adii Pienaar is the Founder of PublicBeta


rand“It’s easier to build a brand on providing a simple solution” – Rand Fishkin

Five years ago, I wished I’d known more about software and product development. Specifically these two: 1) that big software projects have to be built in small, iterative, testable chunks and 2) that it’s much easier to build a brand and be known for simple solution that solves one problem than a complex solution that solves many.

Rand Fishkin is the CEO and Founder of Moz


ryan“Learn from mentors” – Ryan Hoover

I wish I recognized the value of mentors earlier in life. If you’re not seeking advice and learning from others’ experiences, you’re not optimizing your time and missing serendipitous opportunities.

Ryan Hoover is the Director of Product at PlayHaven and creator of Startup Edition.


ben“Finding product/market fit is harder than I thought” – Ben Yoskovitz

“One thing I wish I knew 5 years ago (that I learned the hard way!) was just how hard it is to find the intersection between the right product and the right market–what we now call product/market fit. It’s a Herculean task to get there, most don’t make it, and there’s no obvious road.

Having said that, if I can add in one more thing I wish I knew back then, was that there is a process (Lean Startup) that you can use; a framework for de-risking your startup and searching for the right path. That would have been very helpful 5 years ago!”

Ben Yoskovitz is VP of Product at GoInstant and a partner of Year One Labs


kate“Be patient” – Kate Matsudaira

A year in the world of startups can feel like 5 years in a larger company, and every year I seem to learn more and more. One thing I have learned over the last 5 years that has really stood out in my mind, though, is how important it is to be patient.

You hear these stories of people making $5k in revenue in the first month, or companies that have 100,000 users right off the bat, and so expectations of what is reasonable start to get somewhat distorted. The reality is that many successful businesses are built step by step, and that even the ones who do achieve crazy results have often had a long buildup (through their audience, founders, etc.).

I recently read an article that quoted Jeff Bezos, in which he said it takes 7 years to build a real business. For me, I have had to learn to focus on the long term and not get disappointed when you don’t see the crazy growth numbers often cited in startup success stories. It can take a lot of time for people to notice real value, but if you focus on your customers and building products people love, then you are on a path that — given enough time — will pan out.

Kate Matsudaira is the Founder of Popforms


henry“Ask for help” – Henry Tsai

People are so willing to help. Ask for it then pay it forward.

Henry Tsai currently works at Yahoo, and was formerly part of Astrid


What about you? What do you wish you knew five years ago? Let us know in the comments.

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Written by Belle Beth Cooper

Belle is the first Content Crafter at Buffer and co-founder of Exist. She writes about social media, startups, lifehacking and science.

  • Great stuff! Nate’s advice about innovation and Henry’s comment on others’ willingness to help is what I always tell people. They never believe me until they put themselves out there. It’s not something that sounds believable until you get firsthand experience.

    I wish I knew 5 years ago that creativity is defined differently for everyone and it’s not exclusive to the arts. I spent my whole life discouraged and thinking I was uncreative because I couldn’t draw. Yet, now I’m doing many things with unique approached that people could never have envisioned before. That’s creativity.

    • Belle

      Great one, Vincent! Thanks for sharing—I agree that creativity is so easy to misunderstand.

  • Bruce McCarthy

    “study a task someone has, break it out into its individual steps, eliminate as many steps as possible” – love it.

    • Belle

      Good advice, isn’t it? I like that one, too.

    • Nicolas Daudin

      Yep, love this too! 🙂

    • Jason

      Check out D.S.S.S – Timothy Ferriss’s Model for Rapid Learning


      This piece of advice is very freeing. I think it’s so easy for people to go into analysis paralysis mode as they try to think of how to do something magical like create a time machine! Even entrepreneurs doing mind blowing things such as Elon Musk started doing something a little more normal (paypal).

      Create time machines when you are a billionaire with all the time in the world. Just make something a little bit better over and over again to get there.

  • so. cool.

  • Larry Kim

    great round-up Beth!

  • I wish I had started building a list from the get go and worked with mentors or biz coaches.

    • Belle

      Good one, Brenda. Thanks for sharing your thoughts!

  • Denise Rolland

    Wow, AWESOME stuff here and TY for this post!

    • Belle

      Thanks for reading, Denise!

  • Michael Feeley

    A great article Belle Beth! Every point expressed is so valuable and by many of my favorite business people. You write so well…carrying your reader along from beginning to end. Thank you.

    • Belle

      Thanks Michael! So glad you found this useful 🙂

  • An excellent list of “words of wisdom”. I have been in business for 3 years and can relate to a lot of these. The one “solve one problem” really hits home. This is such a good piece of advice.

  • Nicolas Daudin

    And yourself, Belle, what do YOU wish you knew 5 years ago?

    • Belle

      I wish I knew how to work smarter, not harder. I’m not sure I’ve worked it out even now!

  • My favorite “It’s easier to build a brand on providing a simple solution” … so true.

  • Hank Klinger

    This is a great article, I think mentoring and asking for help are things a lot of people neglect that can make all the difference. Modeling success is a sure fire way for duplication, it works better than any method. Why not learn from the ones who have already made things happen?

    As for myself, I may be new to the industry but a general rule of success in every facet of my life has been to always go into anything with the intention of adding value and increase to peoples lives. No matter how small or big the task I always make it about how I can make life easier and more effective for other people. You always hear go with intention and know your purpose… I find if you keep your intention to provide value, and your purpose the task at hand, it’s hard not to create quality work. Thanks for the post, awesome stuff.

  • Dheeru Singh

    Such A Great Stuff! Thanks For This Post.

  • As an entrepreneur who is focused on innovating in a very well-established industry, I really appreciate the encouragement and insights throughout this article. Thanks Belle for putting this together for us.

  • Dan Horton

    This is a heck of an article. I think you actually earned that crown.

  • mennah

    how to work online

  • Herve Humbert

    Spot on. Only comment would be on nbr 7. Branding for an early stage business is not a key requirement. But a “me brand”, i.e. work under your own name is very true. People buy from people, not nicknames.

    And as for 4, we’re still working on it. Lucky to be facing quite a few opportunities to apply the tech so they would appear we could be many thing to many people, tempting but clearly would be confusing!

    Article shared 🙂

    • Sarah Key

      I think it depends on your field of activity. For artists, it’s very common to have nicknames, and especially for musicians. I think people buy a feeling related to a name, not the name itself.

  • Mrs. Cooper

    Great Article! In depth and candid revelations.

  • …you mean besides “watch out for that 3rd glass of wine because once you hit 30 it goes straight to your hips?”…

    I’d say “know when to walk away”. This applies both to life as well as business and online dealings. Sometimes the return on the investment (friendship, lover, client, all of the above….) isn’t worth it from your end. Know when to walk away.

    • louise mason

      This is so true, difficult to do but true.

  • Ziad k abdelnour

    An entrepreneur is someone who solves people’s problems on a profit margin
    I believe that to create real wealth one must be willing to abandon
    one’s limited thinking, remove the boundaries around our abundance, and
    stop outlining how it is to appear in our lives. Remember not to create
    boundaries and remember not to define the outcome. Most importantly,
    stop letting people who are motivated by jealousy and envy dictate what
    your limitations are.

    Thank you

    Follow me:

  • Priom

    I can’t get enough of Buffer blog =)

  • valeriya P.

    “building a billion dollar business starts with a decision” This is the truth. Alot of people have a great idea but are too scared to pursue it

  • Great post. The insight from Ben Yoskovitz in this post was re-published in Lean B2B: Build Products Businesses Want (