5 Lessons for Entrepreneurs

Ian Lurie
Because business

Last February, I had to have hernia surgery. I was so stressed about work that, as they put me under, I was just happy to get some sleep.

Yes, I was treating abdominal surgery as ‘me time.’

For me, late 2014 to early 2015 was a poop cyclone of biblical proportions. Things have changed. I’m very thankful that 2015 is ending on a super high note. But hard lessons were learned.

Hopefully, I can help others avoid The Six Months Of Living Ianously, and boo-boos made in the preceding 19 years. Your mileage may vary:

1: Believe it: It’s what guides your work

You have to believe in what you do so viscerally that when everything at your company falls apart (it will) and you’re thinking “Screw this” (you will) there’s some intangible, infuriating reason that you don’t shut everything down, sell the furniture, throw the 400 computer monitors into your garage and go get a real job.

You can’t explain it to anyone else. Hell, you can’t explain it to yourself. But you keep at it, even when you’re neck deep in warm runny poo.

All the philosophical business books in the world can’t explain it. An entrepreneur’s belief is small, furry and very nimble. You glimpse it in the corner of your eye but never get a good look. Here’s what defines it:

It’s all personal

Don’t let anyone tell you otherwise. When the business is yours, nothing is ‘just business.’

That’s particularly true because no one says “It’s just business” when they’re doing something good. They say it when they’ve stolen your best bicycle, burned your house down and carved “HAHAHAH GOT YOU” in the wreckage.

You feel very, very responsible for your team and their livelihood. You feel very, very responsible for your clients and customers.

It’s all personal.

Love what you do enough to teach it

Part of belief is knowing—KNOWING—that what you do is worth teaching to others.

It’s not religion (usually). But you must know, deep in the twisted little recesses of your psyche, that what you do has real value. And you must be driven to teach others about it.

Love what you do enough to learn it

You also have to want to relentlessly learn and improve at your craft. No matter what your business does, there’s no ‘routine.’ You’re always deepening and broadening your knowledge.

That keeps you enthusiastic. It makes you a repository of learning for your team. And it’s a powerful competitive advantage.

Plus, face it: You didn’t start your business so you could settle into a nice, mind-numbing routine. You want to do the cool stuff. The more you learn, the more you get to do that stuff.

The customer is not always right

You have to believe you know better. If you don’t, something’s not right.

Be prepared to diplomatically tell those who rely on you that they’re doing it wrong. Then help them do it right. Letting someone who pays you for knowledge (all customers do, no matter what you sell) proceed under incorrect assumptions is dishonest and bad business.

2: Balance work, life and health

Entrepreneurship doesn’t turn your life into a shitstorm. The shitstorms are the bad times. It does, however, turn your life into a sort of ongoing shit drizzle. It’s inescapable. What separates entrepreneurs from other professionals is that we like it. Being the underdog, building something great then doing it again is a rush. Like Omar says: It’s all in the game.

But you still have to survive the experience. No matter what you think, the sacrifices you make to build your business are not temporary. You’ll still be making them in ten years. You can’t skip the gym, not see your family or eat like crap ‘until this one crisis is over.’ There’s always another one.

Even if you sell this company, you’ll start another. So you need to build a sustainable, happy life with your work in mind.

Yes, there will be drama. But set a routine so that you have a ‘normal’ you can return to.

You can work any 100 hours/week you want

Throw the idea that you can work a 40 hour week out the window. I bet you think about your company when you’re at home. You probably think about it when you’re on vacation.

Your business is a big chunk of your life. You’ll put a lot of time into it. That’s because you like it. Admit it and manage accordingly.

Your family must support what you’re doing

Your family must be OK with the fact that you’ll think about your company when you’re at home and on vacation. They have to understand why you sometimes slam those two glasses of wine or Kit Kats (my drug of choice) as soon as you get home. If they can’t support you, forget it. The stress created will fracture your business and your family life.

Respect your family’s feelings in the matter first. If the work you do can’t integrate with family life, assess carefully. Change the way you build your business to fit the way you build your life.


You still have to clean the toilet now and then

You’re still a part of your home. You have responsibilities there. Even CEOs still have to use a plunger and clean the litter box.

I just spent most of Sunday trying to wrestle a Christmas tree apparently made of lead into its stand. And I’m not even Christian. After that, I mucked out my guinea pig’s cage, cleaned the litter box and chased the dog away from the Christmas tree for an hour. Just an example.

Yeah, there are ‘people who can do that.’ But at home there’s a limit to delegating. Do some of the dirty jobs. They’re kind of therapeutic, actually. Especially chasing the dog around.

Your first duty is to remain standing

In late 2014, as the Storm Of Excrement began, I got sick. Really sick. I was bedridden for about 4 days, homebound another 4. I lost about 18 pounds. I missed a speaking gig (first time ever) and a family event. And while I looked svelte, it was not worth it. I recommend eating less instead.

You can’t build a business if you’re in the hospital or otherwise flat on your back.

Yes, you’ll work really long days. But the baseline is your ability to function as a human being. Your business will suffer more if you keel over or have a nervous breakdown. So will your family.

It’s a lot easier to build something amazing when you’re healthy. So take care of yourself.

Treat yourself. You deserve it.

Sure, delayed gratification is part of the schtick. Yes, the work is a reward in itself.

You still need to treat yourself now and then. Use those miles you’ve stacked up to fly First Class. Buy a slightly nicer car. Take three whole days off (your boss says it’s OK).

I’m a car nerd, so I have a nice car. There’s no practical reason for me to have it. But I love my car. I couldn’t buy that car if I’d worked at BigCorp for 20 years. It’s a luxury. Call me shallow.

But when all the high-minded idealism fails you, having an experience or a thing that puts a smile on your face can keep you going.

You don’t have A.D.D. You’re just disorganized

I hear about 75% of entrepreneurs proudly say “I have A.D.D.” to apologize for missing a meeting, changing team priorities and otherwise wreaking havoc around them.

What you really have is a lack of discipline around your schedule and your work. And while forgetting things and missing meetings may seem endearing, it’s rude and leaves those around you feeling unimportant.

A little data: About 4% of all adults suffer from A.D.D. See this study. Entrepreneurs may suffer from it more than others. Not as many as claim it, though.

Get organized. Get a personal assistant. Learn to manage yourself. The scattered mad genius routine will only get you so far.

When your gut speaks, listen

As a CEO, I’ve ignored gut instinct many times. I’ve regretted it every single time. Every time.

Data can’t make business decisions. That’s why you’re here.

Never ignore those little pokes and prods sent by your entrepreneurial instincts. Temper them with rational thought. But never, ever ignore them.

3: Growth must be sustainable

Growth creates pressure on your team and your venture. That’s OK. Pressure is near-term stress with the clear upside of profit and a better business. Poorly-managed growth has no upside and creates wear and tear. That’s not OK. Wear and tear is long-term trauma with no real benefit.

Avoid wear and tear by managing risk and weighing rewards as intelligently as you can.

You are taking risks, not crashing cars

A $1000 risk for a $1 upside makes no sense. You need to know how to make that calculation, even when you have no data.

At a networking event last year, someone asked me for business advice. I kept my sarcastic, self-deprecating remarks to myself (for once), and chatted with her for a little bit.

Short (heavily-modified) version: She had an idea that could earn her $200 per customer. It wasn’t a new idea, but she could do it better. She needed to spend $250,000 to get it going. She expected to capture 50% of the market. Her business plan depended on it.


There’s risk taking, and then there’s business suicide.

You’ll always have unknowns. If you understand the upside and downside of good and bad outcomes and adjust accordingly, you’re taking a risk.

If you’re spending money and time based on ridiculously optimistic pulled-out-of-your-behind assessments, you’re crashing cars. You’re driving towards a wall at 60mph, hoping a miracle happens.

Risks are fine. Recklessness is not.

Acknowledge your team

Don’t just pay them. A good salary matters. But so does being noticed.

Say thanks. Praise when it’s appropriate. Come out of your office now and then. Keep the door open when you don’t.

Everyone on your team can find an easier job. They’re there because they want to work with you. Make sure they know you know that.

Hire for intelligence, not skills

You can learn anything, if you can think.

Mic drop.

Hire for EQ, not polish

I’m Jewish. I point this out because it’s relevant to this story: I once interviewed the best programmer I’d ever met. He was a great communicator, sharp as hell and knew 8 different programming languages. I had the contract in my hand. As I handed it to him, he told me he hoped I wouldn’t “Jew him down” on his salary. Yeah. No.

The lesson: A well-qualified asshole in a suit is still an asshole. A person with real emotional intelligence and brains can grow into an amazing asset. You can always buy them a suit.

If someone makes you squirm in their interview, they’ll be a lot worse when they come to work. Alarm bells for me are:

  • Attempting to BS their way past a question, instead of admitting they don’t know
  • Disparaging remarks regarding previous employers or colleagues
  • ‘Personal’ comments in social media that make you uncomfortable
  • Dismissiveness of any kind
  • Anything alarming you try to justify as ‘nerves’

No matter what the job description, everyone has to look their colleagues in the eye. Hire people who can do that with sensitivity and class. Otherwise, you have to babysit and will spend more time dealing with interpersonal conflict than growing the business.

Teach everything

Teach until you’re redundant. Dump everything possible out of your head and into others.

You’ll never succeed. It’s impossible. That’s why you’re doing what you’re doing.

You may worry that others will ‘steal’ your knowledge. So what? If they literally ripped out your synapses and jammed them into their skulls, they still won’t be able to do the work better than you.

There is nothing more valuable than a smart, autonomous team. That’s how you build sustainability.

Learn everything

Learn from your team. Really learn from them. Demonstrate it.

It makes you better at what you do. It makes you a hell of a lot more effective as a leader.

Show willingness to learn and then take your team’s good advice and act on it. They will love you for it. They’ll be more likely to learn from you. Your business will grow as a result. Learn from your team.

And do it in public. Learning in public may be the most important thing you do as a leader, because it establishes a precedent: If the boss is comfortable saying “I have no idea how to do this, let’s figure it out,” then everyone else is, too.

Work at the edges. Delegate the middle

Your work lives on a kind of spectrum:

Work at the edges. Delegate the middle.

Work at the edges. Delegate the middle.

You should focus on leadership and expertise, then let your team execute. They’ll be better at it than you, anyway.

You should still learn to do the stuff. Just make sure you spend more time learning and leading. That’s how you stay sustainable.

Cash flow is king

You can’t breathe without air. Your business can’t survive without cash.

We’ve all made the mistake of draining the coffers, hoping The Big One will land and bail us out. Try to avoid it.

For me, that meant having a really good finance person working with me. She can occasionally grab me, slap me around and say “Ian this will cost too much money.”

Just remember: Optimism doesn’t help you make payroll. Cash does.

4: Build and demand TRUST

“It’s just business,” a client’s attorney told me as he fed our contract into a shredder and refused to pay a $10,000 invoice. I could go to court over the invoice. But the attorney knew damned well it would cost more than $10,000 to do it.

My point: If someone’s determined, all the contracts, non-competes and disclaimers on the planet won’t protect you. Those pieces of paper are fake trust. They generate compliance processes and paperwork that take as much time as the work itself.

Ultimately, real trust is the only way anything gets done.

You need to earn trust from your team, your customers, and your colleagues. Whenever possible, work only with those you feel you can trust. It’s a hell of a lot less work.

Integrity is your ace

It’s not a renewable resource. Handle yourself with integrity:

  • Be honest
  • Own mistakes
  • Be as transparent as you can
  • Stick to commitments except for extreme circumstances (like illness, family emergencies, or a client that swears at your team)

Every time you damage your integrity, you chip away at it. It doesn’t come back.

And your integrity is also your company’s.

Clarity is good

A business with clarity can grow.

Everyone should understand their job. It needs to be clear. Especially the part where they have to pitch in outside their job descriptions. Yes, you need to have clarity about lack of clarity.

You need to over-communicate concise goals and messages around company vision and values. I mean over-communicate until you’re embarrassed. Literally sit everyone down once a month and repeat those goals, out loud.

Then be sure all of your systems—performance management, accounting, project management, whatever—support those goals and messages.

Set clear standards. They reduce surprises. And when the work does fall short, everyone understands why. If the standards are clear.

Clear standards make it easier to deliver. They also set easy-to-understand rules for success. That builds trust.

Chaos is bad

If you use the word ‘restructure’ in a leadership meeting more than once every year, you are screwed.

Most of the time, if systems and structures aren’t working, you either:

  • Have too many of them
  • Are doing a bad job of explaining/implementing them
  • Have the wrong people in the wrong places

None of these justify restructuring your company. Restructuring creates fear. It eats up time better spent doing other things. Most important, it disrupts the sense of flow your team needs.

That’s the most common form of chaos. But any frequent change in systems and processes will wreak total havoc.

Don’t fart in public

People remember that.

Don’t complain/accuse/air dirty laundry in public. It’s really easy to do online.

We all occasionally vent, leaving out names and facts. OK. Not great but therapeutic.

But don’t point fingers, air disputes or otherwise take something nasty and personal public. You never, ever come out ahead.

It’s really tough. It can be very hard to take the high road when someone’s industriously stabbing your character in the face. But high integrity has this amazing benefit: Other people stick up for you. And you’ll be around long after the low-class hacks are gone.

You can, by the way, send a clearly-worded note to the other party telling them to shut the hell up.

Crazy isn’t motivational

No one likes working for a nutjob.

I’ve had bosses who yelled, screamed, cursed, threw things and generally made their employees quail.

If you’re that boss, you’re not ‘eccentric.’ You’re not ‘unique.’ You’re a bully.

Sociopaths tend to put people on edge. People on edge don’t form trusting relationships very well. They focus more on avoiding mistakes than doing good work.

By the way, I was no prince back in the day. I could have a tantrum with the best of them. I learned to take a time out. Sometimes I just say, “Give me a few minutes to think about it.” Sometimes I have to take a few cleansing breaths. I also switch into teaching mode more quickly. Looking at a problem or crisis as a learning opportunity sounds cliche, but it completely changes my response.

And, of course, I’ve just gotten older. Maybe that helps.

Regardless, take a time out before you start yelling at people. Temper tantrums carve away trust and toss it in the incinerator. You won’t get it back.

Nice is not helpful

It’s destructive.

Part of trust is demonstrating you stand behind the values and standards you’ve set.

If someone fails to perform within those structures, you need to act. Being ‘nice’ and giving them third, fourth and fifth chances may help them, but they’re probably a real and psychological drag on the team.

If a client abuses your team or repeatedly pays you late, it’s not ‘nice’ to keep them around.

Sometimes, nice erodes everyone’s trust in you: If you don’t follow your own rules, why should they?

Fix it

Mistakes happen. It’s how you react that counts.

Owning a mistake and making it right says a lot about a person and a company. Sometimes that hurts. A lot.

Take, for example, The Great Philsophy Massacre of 1995.

I’d just completed a print piece for a client (yes, back in 1995, we actually created marketing materials on paper). We’d reviewed it. The client reviewed and signed off on the proofs. Somehow, we all missed the fact that we’d misspelled the word ‘Philosophy,’ which happened to be in 96 point type at the top of the back page.

What to do? The client approved the proofs. Strictly speaking, it was on them. But I was the words guy. The words were broken.

I ended up eating the entire print job, which cost me a staggering $2,500. At the time, that was half my monthly income.

That really sucked. I mean, it really sucked. I still felt stupid. I just felt poorer at the same time.

On the other hand, I could sleep the next night. And I didn’t worry about seeing the client on the street someday.

And they kept working with us for another 10 years. So it paid off.

Ownership of mistakes is a lot easier than fighting over them. It takes less time, leaves everyone feeling better (at least anyone you’d want to work with) and delivers good corporate karma. Which goes far.

5: Leadership in all things

“Leadership” is a loaded term. For me, it means:

  • Actually making decisions
  • Becoming a positive influence for an audience
  • Helping that audience work together to create better stuff than they could alone

Over 20 years, I’ve learned these are essential:

Listen, then decide

PLEASE. You are not running a democracy. You’re not even running a republic.

When faced with a decision, you can ask for input. But ultimately the decision is yours to make.

Data can’t make it for you.

A vote can’t make it for you.

You’ll be accountable for the result.

Sitting there paralyzed won’t help. You’re not being ‘deliberate.’ You already know what to do. You’re just hoping that choice will leave you alone, and it won’t. It will lift one humungous foot, lower it on your squishy parts and then wipe off the mess on your doormat on the way out.

Make a decision.

You do know what you’re doing

Even when you don’t.

There’s a great scene in The Lord of the Rings: The Two Towers. Theoden is walking with Aragorn through Helm’s Deep, loudly proclaiming his few hundred poorly armed peasants would easily hold off an army of thousands of pissed off Uruk-hai.

Really, they had almost no chance. But in the absence of other options, what else could he say?

Hopefully your team never faces dismemberment at the hands of fanged monsters. But there’s a valuable lesson here: Your team will not do better work if you run around screaming, “Doomed! We’re all doomed!” They won’t respond well to a crisis if you barricade yourself in your office and stop answering e-mail.

Every now and then, you gotta just fake it.

And yes, that can conflict with trust. Life’s full of ambiguity.

Founders must build the thing

If you found a company that does something, you must know how to do it.

If you don’t know the work, you don’t understand your team and their motivations. You don’t understand what they have to do. And you make one bad decision after another.

Reveal to discomfort

It’s easier than hiding.

I overshare. It’s just me. But I find it far easier to do that than to try to remember the last thing I didn’t say, or that I lied about, or whatever.

If I think information will help, or at least not hurt, my team, then I put it out there. At the very least, it puts decisions in context.

Have a sense of humor

Never take yourself too seriously. I may be the curmudgeon of my entire industry, but I’d be long dead if I couldn’t laugh at my own ridiculousness. If there’s one thing to learn from me, that’s it: Humor is therapeutic. Self-directed humor is the best learning tool. And if you’re like me, you’ll produce a lot of material.

Even while you build something great.

This matters, even if you’re not an entrepreneur

Not everyone’s an entrepreneur, but we’re all self starters.

Running your own business doesn’t make you an entrepreneur. An entrepreneur takes financial risk above and beyond what’s necessary to earn what they earn.

That’s not a good or bad thing. It’s in the wiring.

But entrepreneur or not if you’re reading this chances are you’re in some way a self-starter. A lot of the same highs and lows apply.

Regardless, you’re in for one hell of a ride. Enjoy it, and learn along the way.

People who taught me

I’ve learned a lot from some great thinkers and their books:

Business writing:
Ben Horowitz, The Hard Thing About Hard Things
Patrick Lencioni, Everything he’s written
Guy Kawasaki, Enchantment

From history:
Stephen Ambrose, D-Day (great lessons on leadership and team building)
Doris Kearns Goodwin, Team of Rivals (ditto)
Steven Johnson, The Ghost Map

The slides

This piece is based on a presentation I gave two years ago:

Check out Portent's Free Digital Marketing Training Library

Ian Lurie

Ian Lurie is founder of Portent. He's been a digital marketer since the days of AOL and Compuserve (25 years, if you're counting). Ian's recorded training for Lynda.com, writes regularly for the Portent Blog and has been published on AllThingsD, Smashing Magazine, and TechCrunch. Ian speaks at conferences around the world, including SearchLove, MozCon, Seattle Interactive Conference and ad:Tech. He has published several books about business and marketing: One Trick Ponies Get Shot, available on Kindle, The Web Marketing All-In-One Desk Reference for Dummies, and Conversation Marketing. Ian is now an independent consultant and continues to work with the Portent team- training the agency group on all things digital. You can find him at www.ianlurie.com

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  1. Wow Ian, this may be one of the best articles I have read related towards Entrepreneurship. Your 5 lessons really helped me as I could related to some of them and the experiences. Also love how you said after lesson 5, ” Running your own business doesn’t make you an entrepreneur. An entrepreneur takes financial risk above and beyond what’s necessary to earn what they earn. ” SO TRUE!

  2. I think balancing work and life is by far the hardest thing about being an entrepreneur. When you have a regular job, it’s easy to switch on and off between “work mode” and “off mode”, but when you’re an entrepreneur, you’re constantly thinking about your business. Sometimes it makes me a bit envious of the 9-5’ers

  3. We never know what people deal with in their lives. Thanks for sharing, Ian! Very on-point here. Lots of valuable teachings! 🙂 Cheers, Jon

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