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What These 13 Successful Entrepreneurs Wish They Knew 5 Years Ago

Oct 16, 2013 7 min readSelf-Improvement

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.


“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


“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


“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


“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


“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


“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


“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


“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


“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


“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.


“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


“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


“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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