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Business Lessons from 4 Successful Entrepreneurs [Video]

Business Lessons from 4 Successful Entrepreneurs [Video]

Home Blog Digital Marketing Planning & Strategy Business Lessons from 4 Successful Entrepreneurs [Video]

We’re living in a time in which entrepreneurship seems glamorous. Everybody is a founder of something. Or wants to be.
Popular culture, using a handful of isolated success stories, has told us that if we’ve got a few great ideas, some grit, and maybe a garage, we will succeed. Who needs school? Nobody makes dropping out of college more glamorous than Steve Jobs and Mark Zuckerberg.
“I know my life doesn’t make sense right now, but we’ll connect the dots later once my startup go public.”
That’s what every college dropout wants to believe.
But the actual day-to-day work of building a real, lasting brand is anything but glamorous. And nobody knows that better than our guests for this episode of Real Smart Marketing.
We invited some of the best founders of the digital marketing world to share the biggest lessons they’ve learned while building the brands we know and love.
Want to learn about the stories that shaped Wordstream,, Moz, and Duct Tape Marketing?
Hear it from the founders:

Big business lessons 4 founders learned while building their brands

Building a brand is no walk in the park. Here are four big lessons our favorite entrepreneurs learned the hard way:

1. Learn from your rejections

Who would’ve thought that Larry Kim – founder & CEO of MobileMonkey and top columnist of every online publication there is – was once rejected by more than a hundred venture capital firms?
“I had pitched to over a hundred venture capital firms asking them to invest in my business, and all one hundred of them rejected me. That was kind of a bummer because, to get rejected a hundred times kinda hurts your feelings,” said Larry.

The reason why Larry Kim became “Larry Kim” is he used these rejections as pointers for improvements.
As he said, “within all those rejection letters there were often a bunch of reasons why they didn’t like the business. So I was able to use those letters to put together a roadmap of what I need to do to make my business stronger.”
Within nine months, he raised his first four million dollar round. And now Wordstream is marketers’ go-to platform for PPC ads.
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Lesson from Larry: when life give you lemons, don’t throw them away, study them.

2. Scale and hire wisely

Every company wants to grow. But at what pace?
It’s easy to get caught up in the excitement to scale and hire too many people too quickly. But not getting the timing right can break your business.
Noah Kagan, founder of, learned it the hard way.
“Our main thing was we hired too many people. In 2014, we went from four to twenty, and we ended up firing a lot of those people, which sucks for everyone.”
But that crushing blow taught him to revamp his business and hiring plan, build predictable revenue so he can scale accordingly, and create a better process for hiring the best people.

He also shared a fun tip for deciding whether you really want a candidate. Ask yourself “how would I feel if my competitor hired this person?”
That’s helped him gather a winning squad at

Lesson from Noah: don’t rush to crack your eggs before they’re hatched. Slow and steady wins the race.

3. It’s never too late to fix a mistake

If you’ve worked in a startup, you know that a lot of things happen at the same time. Your team is spread so thin that you can rarely see where your to-do tasks begin or end.
One day you’re fixing a bug on your website, and the next day you’re building your email lists. And as you’re running around with barely any time to breathe, you’re bound to miss a few important steps.
The same went for Rand Fishkin’s team at Moz, when they were just starting out in 2004. They were collecting lots of email addresses from people who signed up or used their product, but they never emailed them.
Those leads were just sitting there, slowly going cold and being wasted.
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(Pun intended)
Luckily, five years later they finally decided to fix this mistake and launched their email marketing.
The campaign went massively well – thousands of people signed up. There were very few spam complaints and unsubscribes, despite the fact that they failed on the email marketing front for so long.
Lesson from Rand: you can change your past by doing the right things today. Never too late!

4. Choose protecting your values over making profit

When you’re just starting your business, it’s natural to want to take whatever client you can get.
In the best case scenario, you’re eager to make your name and prove your business is profitable; in the worst case scenario, you just simply can’t afford to be picky because the bills are piling up.
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But John Jantsch, founder of Duct Tape Marketing, shares a scary story where this mentality got him in a sticky situation.
Because he was accepting whoever was willing to pay, he “attracted clients who weren’t a great fit.” In fact, he “had a client that was doing some things pretty shady” and he ended up “in front of a grand jury investigation.”
Fortunately, he didn’t know anything that the authorities cared about, but it taught him that he needed to choose who he wants to work with.
“I realized that I had to get very good at expressing what my values were, and what my purpose for being in business was,” said John.

Doing so will not only help you avoid prison, but also attract the ideal client that resonates with your brand identity, with whom you can have lasting relationships with.
Lesson from John: making money isn’t the most important – better to lose a client than lose who you are.

Fail often, and learn more

Webinar Learn from neil patel's mistakes - exclusive webinar@2x

These cool bunch didn’t become who they are today without tripping over some hurdles. But they didn’t give up, and took those failures as opportunities to learn.
In the risk of making this post even more soppy and cliched, here’s a great quote from the cartoonist Stephen McCranie,
“the master has failed more times than the beginner has even tried.”
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If you feel inspired by this post, check out our exclusive chat with Neil Patel, another online marketing giant, where he shared a lot of common mistakes people – including himself – make while growing their brands, and the best ways to avoid them.

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Joei Chan

Guest Blogger @Mention