What We Wish We’d Known 5 Years Ago – 13 Successful Entrepreneurs

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 five 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 business 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 intelligence 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 Clarity.fm.

“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 five 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 five 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 five years in a larger company, and every year I seem to learn more and more. One thing I have learned over the last five 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 seven 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.

This post originally appeared at Buffer. Copyright 2013.

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The 13 Approaches to Quitting Your Job Without Burning Bridges

Often times the most difficult aspect of quitting your job isn’t figuring out what to do next. You could go climb a mountain.  Build out any number of a hundred business ideas you already have.  Sit on a beach in the tropics for a month.  There’s no shortage of things to do with free time. No, the hardest part of quitting your job is often the simplest: telling your boss or current employer that you plan to leave.

It doesn’t matter if you’ve been working with them for 6 months or 6 years, when you’re spending more time with them than your own family, it can be an agonizingly personal endeavor to tell them you want to go elsewhere.  It’s almost like going through a breakup after years of dating.

In the three years I’ve been working with people to help them quit their jobs and build sustainable businesses, I’ve seen all kinds of different ways to approach that fateful day where you march in and say “hey boss, I’m outta here.”

Sometimes it goes really well.

Other times? Well, not so much.

So if you’re thinking about quitting your job, how are you going to approach it? What’s your reasoning going to be?  How are you going to get them to understand exactly why you’re doing this?  What do you need to do in order to prepare for the big day?

Easy, you’re going to read this guide.

Here we will talk about 13 different approaches to leaving your job, the potential objections/responses to each, and how you can prepare yourself beforehand to give yourself the best shot of remaining on good terms after your last day. My goal with these was to make the departure as positive as possible for both parties, however there are a couple that may lead to hard feelings.  Keep this in mind if going one of these routes. Also as you’re preparing to make the leap, there’s definitely some recommended reading before jumping right in and peacing out:

• 6 Questions You Must Answer Before Quitting Your Job. Use this as a guide to figure out if you’re actually ready to leave your job.
• How to Get More Value and Enjoyment Out of Your Day Job. If you’ve answered the previous questions, and come to the conclusion, you aren’t quite ready yet, then use this post to ensure you’re still making the most of the time you have.

Now, onto the 13 approaches for quitting your job!

#1: The Quarter Life Crisis

One of the most common approaches to leaving your job comes from those who have graduated within the last five years and are often still in their first job out of college.

Me at the height of my quarter life crisis

This is a tough place to be.

I’m willing to bet your first job out of school wasn’t your dream job, yet here you find yourself still working away without much to show for it.

Even worse, you may have a completely unwarranted sense of obligation to your employer.  I did. I felt like since they took a shot on me, I had to stick around forever.

False.

You can use the quarter-life crisis approach in numerous ways.  Tell them you need more life experiences, need to figure out what gets you excited.

This is the absolute best approach when the only thing you know is school and this one job.  You need to have a myriad of experiences so you can figure out what’s actually right for you, not just what’s easiest.

Common Objection: Are you sure you know what you’re doing? You’re just going to have to start over again in 6 months.

Reality: Taking time off to travel and figure out what you want out of life is only going to make you more marketable to employers in the future.  If you get back and have realized exactly the type of work you want to be doing in the future, they will have more confidence in your long term commitment to the organization.

#2: The Timebomb

So you know you want to leave, but you know you won’t be ready for another 6-12 months.  You also know that you don’t want to leave your boss out in the lurch and want to make sure he isn’t blindsided. So what do you do? You adopt the Timebomb Principle like John Devries and others have done.

What does this mean? Essentially you pick a date in the future that you’re absolutely, no matter what going to leave.  Assuming you have a good, trusting relationship with your boss you tell them about your plan.  You explain all the reasons you need to go (of which I’m sure there are many), and work together on your exit date. During the final few months you can help to find and train your replacement to ensure there is no lost progress. This leaves your boss ahead of the game, and you’re able to really put a good exit plan into place over the long term.

John DeVries perfected the Timebomb Method

Common Objection: Why shouldn’t I just fire you right now?

Reality: Knowing that you’re going to be leaving helps keep things on the right track during your final months.  If your boss knows you’re going soon, and you’re one of their star employees, they’ll want to utilize you for every day they have.  They are also getting the benefit of a a new hire, trained by the expert (you) rather than having to start from scratch.

Again, this works best if you have a really good relationship with your boss, and I’ve seen numerous people have success with this in the last couple years.

#3: The Entrepreneur

If you’re anything like me, you want to own your own business.  You want the freedom, responsibility, and rewards that go along with being an entrepreneur. If you’re stuck working for someone else, regardless of how sweet the job is, your lust for entrepreneurship will never be satiated until you give it a shot. Until you do it, you’ll always be left wondering “what if” – a feeling no one should have to experience.

So if this is you, think long and hard about the type of business you want to run.  Get started on the weekends and in your spare time, and once youve got some proof that the idea is viable, it’s time to break the news. Talk to your boss and tell them about your entrepreneurial visions.  This works especially well for small businesses where they are also entrepreneurs – they’ll get it, trust me.

Depending on the type of services or products you’re offering in your new business, your current employer could potentially be a great first client.

For instance, my friend Zach quit his job as a developer so he could focus more on the projects he was actually passionate about.  His company couldn’t stand the thought of him leaving, so they asked him to continue to do some work part time even after he left.  He now gets to work remotely, works half as many hours, and still makes almost as much as he was making before. Talk about a Linchpin.

Common Objection: In this economy you’ll never be able to make it alone, you should be lucky to have any job at all, why would you want to throw that all away?

Reality: Even if you stay there are no guarantees.  They can sack you anytime they want, so by working for yourself you’re beginning down the path of true job security, or job security 2.0 as I call it in Location Rebel.

Worst case scenario? You go back and get a job when you need to – but at least you’ll no longer be wondering “what if?”

#4: The Remote Work Agreement

This can be a great approach depending on a few key aspects of where you’re at:

• Your job is 80% “remotable”. Meaning, if given a computer and internet connection you can theoretically do your job from anywhere.  Note: This could mean you’re making major changes to your routine, but if this rule holds true, there’s always ways to make it possible.
• You’re willing to leave sooner rather than later if it doesn’t work out.  I pitched a remote agreement and it ended in “we will not accept your proposal, but we will accept this as your resignation” – be prepared for this response.
• You’re truly committed to working hard if the agreement is accepted.  If you just want to use this as an excuse to slack off, don’t bother.

I love the remote work agreement because it gets you one step closer to becoming a location rebel.  It allows you to go somewhere new, set your own schedule (usually), and shows you what it’s really like to be on your own.

This can be a great test case for whether or not you’re really ready to branch out on your own accord.

Evan Lovely is one of the best examples of this.  He talked his boss into letting him travel through Asia for 6 months while still taking a full salary and working on the road.  We hung out in Bali for a few weeks late last year, and don’t get me wrong, he worked hard, but he essentially had all the benefits of being on his own, while still having the stability of a real job.

Evan in Ubud, Bali in one of many remote offices

This can be good either way. If they accept your proposal, sweet! You’re one step closer to your goals.  If they don’t, well then you gave it a shot, and you and your boss may just realize your employment isn’t a good fit.

Or door #3 is they simply say no, and you have to move onto one of these other approaches to quitting your job.

Common Objection: Why should you be able to take off to Bali, Belize or Boise while we’re still here in the office?  You’ll be way less productive.

Reality: If you’re serious about this, your remote work can actually be a huge asset to the company.  It has the potential to save them money (depending on the agreed upon terms), bring their business into the 21st century with improved security and remote computer access, while also potentially opening up a whole new client base due to your new location.

If you work for a small company in the US, they could even potentially use you as their “international” office and make themselves seem like more of a global institution.

#5: The Upping the Ante

Maybe you want to leave your job, but it’s mostly because you aren’t being compensated fairly, or you’re otherwise not happy with the effort vs return. With the upping the ante, we strive to get to the point where you’re either getting the compensation you feel you deserve, or you cut all ties and move onto something more worth your time. My friend Beau moved down to the Bay Area from Portland last year after his company asked him to head down for a series of projects.  He was only supposed to be there for 6-12 months, but then they asked him to stay longer. He owns a house in Portland, has a large social circle up here, and really would prefer to be in Oregon than California.  So he initially told his company he wanted to head back to PDX. They said: “How much would it take for you to stay?”

The result: He ended up with a huge raise, better benefits and an increased living stipend to stick it out for another year or two. When you know your company needs you and you’re willing to stay for a price, don’t mess around.  Give them the real number or offer that will make it worth your while to stick it out for awhile.

If they can’t get reasonably close to matching it, then find someone who will.

Common Objection: We’ve never given anyone a 50% raise! That’s insane!

Reality: What’s more expensive for them? Give the dude that’s killing it for them and making them millions of dollars a year a little extra money?  Or have to go through the entire hiring and training process all over again?  If you’re legitimately good at what you do, they’ll understand why they need to pay you.

#6: The Bluff

Similar to upping the ante, the bluff isn’t really a straight up tactic for quitting, but rather an understanding of the importance of your place in the company.

Jennifer did this and didn’t even realize it.  We’d been talking back and forth on strategies for building her new writing business, while also getting her to the point where she was willing to take the nerve-wracking step of quitting her cush job. After finally getting to the point where she worked up the nerve to do it, you know what her boss said? “No.  I can’t let you quit.”

How’s that for a momentum killer?

She was already nervous enough as it was, and then her boss took away all her confidence and she didn’t know what to do.  She agreed to stay on for a month, which gave her boss more time to plan out what was next. She realized in that month just how valuable she was – she knew there was a way to get much more than she was currently, while still setting a timeline for her departure.

After some back and forth, she agreed to a big raise and to stay on until the rest of the year.  All the while, she’s still been growing her business, and has landed a couple HUGE writing gigs.

Now not only will she have the money to really pursue her new business early next year, but she’ll already have the brand, contacts, and confidence in place to do it.

Common Objection: You can’t quit no one will ever hire you again, you need this. (This was the experience Jennifer actually had).

Reality: You don’t need any job, however there’s a very good chance they need you.  If you know this is the case, leverage it, and consider a bluff.  That said you should be prepared for them to call it. If you arent in a place where you’d follow through with your resignation if they don’t give in, then you should probably stick around for awhile longer or try a safer approach.

#7: The Lack of Heart 

No boss can ever get mad at you for being honest about this one.  If they do – then you didnt want to be there in the first place. The best example of  the “lack of heart” I’ve seen is from Lizzie Presson.  Here’s the email she sent to me detailing her situation:

I quit my job, packed my bags and moved to NYC one year ago (July 23rd to be exact). My mentor (Amber Rae) called me and said she wanted me to come work with her in NYC. My boss was on a two week vacation. I called him and told him that I hated to tell him over the phone, but I had to be upfront and honest.

I remembered that a couple of days before I had the news to share he said, “I don’t want anyone working here who isn’t in 100%.” I reminded him of that moment, and I told him that I’d never want to give less than 100%. I would be if I didn’t leave at that very moment (with proper notice of course).

After I landed what I thought was my dream job and taking the risk, it became apparent that the job was not the right fit. I was jobless for the first time ever, living in NYC alone and more confused and scared than ever.

That fear ended up being the best thing that’s ever happened to me. Now, I’m co-founding a new business with someone I respect, and I’ve launch a meaningful project, Worki

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