I’m not a “big trends” thinker. Maybe that makes me short-sighted, maybe that makes me focussed on reality. How much should you care about “trends?”

A lot of predictions are easy. In the next 10 years:

• There will be another “surprising” Black Swan financial market event.
• Mobile device usage will increase.
• “Old Media” will be consumed less.
• Attention spans will shrink.
• New companies will challenge the current guard of Google, Apple, Twitter, Facebook, and Amazon.
• India and China will grow in population and influence.
• The West will become more multi-cultural.
• Today’s technology will become cheaper.
• Tomorrow’s technology will be more accessible to more people.

It seems obvious to follow the trends, paddling downstream with the currents. Surely building a story around a “geo-mobile app with viral social gaming” stacks the funding deck in your favor. Go disruptive or go home!

But everyone else is doing that too. So you’re diving into an ocean of well-funded competitors, all steeped in the culture of “listening to the market,” willing to “pivot” into your space as soon as you uncover evidence of its viability, and fighting over attention and sign-ups with complete disregard to profitability or sustainability, which can come later, after you’ve cemented your growth.

That doesn’t sound easy to me — that sounds scary, and crowded, and risky.

So should you buck the trends? What if you pick a boring niche — even a dying one?

People selling first edition hardcover books are met with dwindling competition and joined with grateful customers who feel abandoned by the Kindle-driven online “book” industry. But the numbers of those customers is itself dwindling and few booksellers make enough money to keep the doors open.

Is that really better?

It depends on your aspirations. If you want a comfy, beloved little company where you can make a nice living, a “A cozy corner bistro on the Web” as Peldi wants Balsamiq Mockups to be, then ignore trends. Indeed, running in the opposite direction is an easier and less risky path, because customers are clear and under-served, perfect for a little startup to service.

But if you have the drive to be the next Twitter or GroupOn or the “Facebook of XYZ,” something big enough and important enough to enough people to generate a billion dollars in value, something that is #1 in its market, then you can’t look backwards; your path must be to follow the trends and duke it out with everyone else…

…except, once GroupOn is GroupOn, is there still another billion dollar opportunity in local group-based deals? To the extent that location-based “check-ins” is a trend, does it make sense to start now and challenge FourSquare? Even if you’re well-funded and have a fantastic team? Ask Gowalla.

No, the next billion-dollar opportunity won’t exactly fit any trend you see today, because the next “big thing” is a trend that’s not yet a trend. If you want to be the next Facebook, you can’t follow the wake of the current Facebook.

Too early and no one understands it. Too late and it’s obvious. It’s precognition combined with impeccable timing.

It’s Amazon selling books online just when everyone wanted to buy stuff online but before everyone believed shipping costs weren’t overwhelming. It’s Salesforce.com helping SaaS become viable before everyone trusted 3rd-parties with their trade secrets. It’s Twitter connecting the world with real-time mass mini-chat before everyone realized how tiny and fragmented our attention spans could become.

What’s the secret to manufacturing this combination of foresight, timing, and financing?

For the institutional investor, it’s a set of bets. Invest in two dozen ideas containing this sort of potential and a few might make the cut. Improve the odds by selecting products with traction backed by a team with the ability to both build and learn. Even so, venture capital has a horrible record in the past ten years — most funds don’t make good money. Still, enough do, and a small subset are able to do it consistently.

For the entrepreneur, there’s no secret. You’ve placed your bet, playing in a game with massive upside but almost certain failure. It’s not wrong per se, it’s just a choice.

If you won’t be happy unless you change the world, you have to bet. Consider the current trends but bank on a new one. In fact, invent one.

But if you don’t need a billion-dollar market cap to be happy and fulfilled, then perhaps it’s not wise to roll loaded dice and muster the chutzpah to claim you alone know the secret of the next global business/consumer trend.

Maybe instead you worry less about trends and more about having a strong opinion about the way your corner of the world should be, and see if you can find enough others who agree.

Chances are, some do.

Am I being dismissive or small-headed? Let’s continue the discussion in the comments.

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The skin between my second and third finger on my left hand has been dry and flaky since middle school; no one knows why. I have a scraggly patch of hair on my right calf from when I scraped off a swath of skin in an Ultimate Frisbee tournament. (I made the catch for the score. My wife asked “Was it worth it?”)

We all have scars. The interesting ones aren’t physical, and are more subtly revealed. It’s the guy who’s a little too steadfast in his claim that “VCs are evil.” It’s the founder who says she doesn’t need to talk to customers before embarking on a $100,000 development project because “my customers are idiots.” It’s the developer who is sure that “Java sucks.”

Scars are part of what make us unique. Dwelling on our peculiar trauma can be a comforting way to develop that uniqueness.

I like scars.
I want to remember.
I want to feel blood and tears.
I want it to feel tender.
I’m watermarked, just like forever.

– Matt the Electrician, Home

That uniqueness is good, or so says most advice. Embrace your scars, embrace your identity, own it completely, and suddenly you’ve solved one of the key riddles in life, not just in startups: Who am I, and how is that different from who anyone else is?

Some of my baggage, however, is a hinderance, whether it’s “defining me” or not. I still find myself sometimes running WP Engine like the bootstrapped startup that it was for the first 18 months of its life, instead of the funded growth machine that it’s evolved into.

For example, last week I spent about 10 hours saving about $1000/mo in hosting costs. Not bad, you say, that’s $1000/mo right into your pocket! You can even make a financial argument: That’s 10 hours to earn $12,000 over the next year, which means my time was worth over $1000/hour, and that’s a good hourly rate no matter what.

No, not no matter what. I could have used those 10 hours to make it easier to share a website speed report and to tell a friend about our free WordPress management portal. And that might have resulted in 1000 people seeing those two things over the next year, 10 of which end up moving their blog to us, and a few consultants who collectively put 20 of their clients on us. Even at $50/mo, that’s 30 x $50 = $1500/mo in direct new revenue plus side benefits in marketing and branding.

If you’re bootstrapping, getting that $1000/mo right now in bottom-line money is in fact the better choice. Money is scarce, time is precious, and $1000 today is better than $5000 next year (which you might not survive to see).

But if you do have money in the bank it’s just the opposite. The goal of investment is to turn “money today” into long-term value, meaning a growing, predictable revenue machine.

So even if you know your scars, embrace them, and have perfectly tight rationalization of why every decision is the correct one for you, it still might be wrong.

What can you do to mitigate this?

First, decide to build a company in which the correct, consistent decisions are the ones you’ll naturally take. If you love optimizing the last dollar out of the process — as I apparently do — build a bootstrapped company. If you don’t like working with people, be a Micropreneur like Rob and Patrick. If you want to leave a mark on the world, have big ideas with lots of people and lots of money, seek advice from those who have walked that particular path before you, to help construct your rules and structure.

Or second, do what I’m doing now: Surround yourself with trusted advisors and be completely and continuously honest with them, then actually listen and learn. I know I’m naturally a bootstrapper, a “get to the first $10m in revenue, but only after seven years, and then what?” type of person, so I know I need constant course corrections.

Really both of these reactions are the same: Get outside yourself and open your ears. Because, as in the example above, you literally cannot possibly know you’re wrong, not even if like me you’re proactively introspective and have a few successful startups under your belt.

I still rationalize. I still follow the ruts of my scars. I need other people to at least be an honest mirror and at best be a loving kick in the pants.

You need it too. Seek it out.

P.S. I’ll be your sounding board and your devil’s advocate, but in public (albeit anonymous, unless you ask for the exposure). Either write me at asmartbear -at- shortmail -dot- com to be a part of my Mailbag Series or better yet call in to the monthly Smart Bear Live show. Next one is in early February!

Where do you go for advice? Where are you blind spots? Let’s continue this in the comments.

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When you talk about explosive, profitable startup growth, a few darlings come to mind. DropBox is one.

Hubspot is another. I mean, just look at their growth (published on SEOMoz):

Was it always so powerful a growth engine? Was it always so clear that this was a company with a bright future?

Looking back on stats they published in 2010, the curve is identical, just a different scale on the y-axis:

Or in 2009, when they published this to boast about how their revenue juggernaut is recession-proof:

Even going back in time, they seem unstoppable, their future inevitable.

But it was not always so. I’d like to zoom in on this point in the graph:

What was going on during those first six months? Was the future bright and shiny even when there was no impressive customer curve? When half the customers were just personal favors called in and new signups didn’t happen daily?

Or was it barely-controlled chaos, not able to sleep at 2:43am for worry about how to make payroll in seven months or whether the numbers would look good enough by next spring to raise another round? Unsure which products to double-down on and which to kill, and worried the wrong choice would tank the entire company? Staying bright and cheery on the outside for the press, customers, and even employees but with Damocles’ Sword hanging overhead?

Of course it was. It always is.

FreshBooks is another example. Here they are in 2007, justifiably proud of getting 138,000 sign-ups in 3 short years:

Founder Mike McDerment showed us the update at Business of Software 2011 — it’s identical in shape, except they just passed 3,500,000 users.

As an aside, they mention that “we didn’t have our first paying customers until month 2.” How do you think they felt before then? Or even in the six months after?

Of course the story is the same when the company “runs off a cliff without leaving skidmarks,” never having extracted a single dime from a single person. The same struggle, same uncertainty, same near-impossibility.

So how do you tell the difference between the chaos that leads to unthinkable success and that which leads nowhere at all?

I’m not sure you can.

Objectively, what’s the difference between Basecamp v1.0 and any number of knock-offs? All of them simple, all of them usable by relatively non-technical people, all of them web-based.

Objectively, what’s the difference between StackOverflow and the twenty copycat frameworks and thousands of copycat websites and forums? Why was Quora still able to stand out? Could you measure this difference? Could you put it on a chart?

You could say StackOverflow was fueled by giants of the technical online world, but that doesn’t explain Quora.

One thing you know for sure — what doesn’t explain it is a standard “feature comparison chart.”  If it’s a feature at all, it might be something subtle, like the exact game mechanics of StackOverflow or the boogers on my diff viewer.

But even that doesn’t explain it. Take Peldi, founder of Balsamiq Mockups. He blogged too, but unlike StackOverflow he didn’t have a head-start with an online presence, and English is his second language. He lives in Italy, not surrounded by an American startup culture to feed off. Prior to entrepreneurship he was a lifer at Adobe, so that didn’t especially prepare him for running a company from scratch.

Guess what his growth chart looks like? It’s like Hubspot and Freshbooks, but what’s more interesting is what it looked like during year #1:

How do you think Peldi felt during those first six months? Do you think the anguish subsided quickly? Or ever? Do you think Peldi was still sure his ideas and execution were good in June?

It’s not just startups. Here’s a letter George Orwell sent in 1948:

… The book is fearfully long, I should think well over 100,000 words, possibly 125,000. I can’t send it away because it is an unbelievably bad MS and no one could make head or tail of it without explanation.  …

… I am not pleased with the book but I am not absolutely dissatisfied. I first thought of it in 1943. I think it is a good idea but the execution would have been better if I had not written it under the influence of TB. I haven’t definitely fixed on the title but I am hesitating between NINETEEN EIGHTY-FOUR and THE LAST MAN IN EUROPE.  …

His book Nineteen Eighty Four is one of the most popular, most-quoted, most influential English-language books of the the last hundred years.

Of course your struggles might indeed be in vain; only time will tell. But this I do know:

The fact that you’re in over your head, that you almost cannot will yourself to continue, that you’re completely in the dark, that you’re working yourself to an early grave, that you seem to slide two steps back for every one forward, that nothing’s ever good enough, that that your friends and family can’t understand why you’re turning yourself inside out with no apparent progress, that you yourself doubt whether you’re even capable of this…

These things don’t mean you’re failing. It’s always like this, until it isn’t.

Discussion continues here.

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Almost no startup founder values her time properly.

Consultants know exactly what their time is worth: their hourly rate. As they say, it’s how much “the market will bear.” When a consultant intentionally doesn’t work for an hour — whether to be with family or to work on a new startup — they’re clearly giving up an hour of potential earnings.

If being a consultant is your goal, this is indeed how you should value your time. But when you’re in a startup, the math is completely different.

Your time is $1000/hour, and you need to act accordingly. Here’s why:

Let’s say as a consultant who normally charges $150/hour you stumble upon a weird client who asks for the following terms:

“We agree your time is worth $150/hour. However, we can’t pay you for four years, at which time we will pay you in one lump sum.”

How much should you increase your hourly rate to make these terms worthwhile?

It has to be more, not just because of the interest you could be making on it in the bank (which nowadays approaches zero as a limit), but because you can’t live off money you don’t have, which means you’ll need other work too, so you’ll need a nice premium to make this inconvenience worthwhile.

But “lost interest” and a premium doesn’t solve the biggest problem with these terms. The problem is: What if this company goes out of business in four years and doesn’t pay you at all?

Supposing this client is an early-stage startup — even if funded — the most likely event is that they stiff you! Because they’re dead. Let’s suppose for the sake of rhetoric there’s a 15% chance the company will exist in four years and pay their bill.

Like gambling in Vegas, the steeper the odds, the bigger the winnings if you beat the odds. In this case you need to charge $150 ÷ 0.15 = $1000 per hour to account for the risk.

In fact, you need to charge more, because that formula merely brings you back to “even!” To see this, suppose you divided your time between seven companies, all operating on these terms. Chances are all but one would fold, that one would pay you 7x your hourly rate, but you’d be in the same place you’d be if you just charged $150/hour on your standard terms.

But you’re waiting four years for that cash! So it’s worse. So you have to charge even more.

Of course this isn’t hypothetical, this is exactly the terms you’re accepting for yourself when you create a startup. The risk is high, so the potential financial rewards must be commensurate with that risk, which means you have to value your time between $1000 and $2000 per hour, not at your $150/hour consultant rate because of platitudes like “my time is worth what the market will bear.”

What does this mean for your daily life?

It means you don’t have time for projects that have the potential only for small, incremental results.

It means a personal or virtual assistant is worth the money.

It means you should focus on building things that are even more valuable than money.

It means you spend the money on a bookkeeper and CPA instead of messing with receipts, Quickbooks, and taxes.

It means you can’t afford to not work harder than is healthy.

It means you should obsess about doubling your productivity.

What else? Let’s continue this in the comments.

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Tired of productivity articles instructing you to break down large projects into smaller, more annoying, and less interesting tasks?

Or about how if even the teeniest little thing remains in your inbox at 5:00 on Friday afternoon, then not only will your entire weekend be shot, but also you are a terrible human being?

Well I figured with the New Year ringing in Resolutions about how It’s Really Going To Be Different This Time, No Really I Mean It Why Are You Looking At Me Like That, it would be a good time to share with you a favorite technique of mine which doesn’t require that you sacrifice a goat at an altar of David Allen.

This technique is weird, and not in a good way. More like a painful, aggravating way, but entirely worth it.

It really does work. You’ll measurably improve your productivity.

It’s called the “Personal Checklist,” which sounds boring and benign but is actually the emotional equivalent of punching yourself in the face.

Here’s how you do it.

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Everyone likes New Year’s Inspiration this time of year; this interview is perfect to scratch that itch.

This is the fourth installment in my “Uncommon Interview” series — interviews where we get right into the meat and dispense with pleasantries or “how did you get into this business” sorts of fluff.

On the other side of this radio interview are Adelaide Lancaster and Amy Abrams, both founders of their own startups, both coaches and mentors to dozens of other startups over the years, and who together created and still run the In Good Company co-working space for women entrepreneurs in New York City.

After years of toil, Amy and Adelaide noticed that many startup founders were unhappy and unfulfilled, and decided to get to the bottom of why, and then figure out how to fix it. After thousands of hours and hundreds of interviews, they produced their own manifesto on the subject, encoded in their book: The Good Enough Company. (That’s a link to their website, not an Amazon affiliate link.)

I think this is a critically important subject, and one that gets almost no attention from the hot-rods of the tech blogosphere, myself included. So let’s address it right now.

You can listen to this audio interview by subscribing on iTunes, subscribing to my usual RSS feed in your podcast-listening-system-of-choice, or just download the mp3.

Don’t forget to continue the discussion in the comments!

Transcript

Automated transcription services provided by:

Jason:  Welcome to this episode of the Smart Bear podcast. Today I have Amy Abrams and Adelaide Lancaster here and we’re going to be talking about their new book, which is called the Big Enough Company. You can probably guess what it’s about just from that. They’re really neat. They have a co-working space in New York City, a lot of people try to do co-working and don’t make it work and they do, which is sort of amazing in itself and it’s called In Good Company. You can find that at ingoodcompany.com. So, hi Amy and Adelaide.

Adelaide:  Hi.

Amy:  Hi.

Jason:  I think every time you watch something like the Daily Show someone’s pushing another goddamn book so, we have to push through that and say why this is not just some interview about some book. I would like to start with why I’m interested in this book, why I thought this would be a fun thing to do, and why I think it’s important, that this book’s important and see if you agree and what you think is important about it, what you like people to get out of it.

Adelaide:  Sounds good. I’m sure we’ll agree.

Jason:  Yeah. So, the internet is full of people saying things like, ‘you have to seek happiness not money.’ Or, ‘Not every company has to be big and be the next Twitter, not everybody even needs employees.’ There’s people like Amy [inaudible] who I think is really inspirational in her blog about it. There’s people like Rob Walling, who are very practical about it and tell you how to do that. Even so, I feel like people read those kinds of things and think, ‘Yeah, I should think about happiness’, but then they don’t it doesn’t sink in. I constantly talk to people who have built a company that there not happy being at, they’re not happy running it, they’re not fulfilled, maybe they wish they’re home more or they’re just unhappy literally everyday.

They’re obviously not taking this advice to heart. I think it’s because you can’t just read it in a blog post once a week or in a Tweet every once in a while, you have to be steeped in it. You have to have a book where you sit there with it for hours, reading these examples and seeing person after person, all sort of living this or making mistakes because of this. You really burn into your brain there really is not one right kind of business and not just that it’s OK to say things like, ‘I don’t want employees’, or, ‘I don’t want to grow’, but that a lot of people ought to when they’re not.

It’s OK to consider things like that growing a business means that most of your daily activities aren’t things you want to do. There’s the fact that money does not automatically make you happy. There’s family time, hobby time, and flexibility where you live or whatever. Things that are also important to you that are equally important than some of these traditional business things. If you don’t sit down with a whole book and read example after example that beats it into your brain, you’re just going to nod and move on and it’s not really going to affect you. So that’s why I think it’s important. What do you guys think?

Adelaide:  Well, we couldn’t agree more. I think there’s a lot of what you just said that’s really interesting, Jason, and I feel like a lot of that was the motivation for writing this and really, we [inaudible] a couple of different strategies in doing this, right? So, we obviously wanted to, felt like what we had to say or felt like these stories and this message was important enough to add another book to the bookshelves and we totally agree that there are already a lot of books there but what’s also really important for us to include this many stories for that exact reason, because we wanted to people to, I think that you have see it and read it in a lot of different kinds of ways and see a lot of different kinds of examples to find ones that really speak to you and that you can kind of relate to and that match your situation in order to be motivated enough to do something and to say, ‘You know what, my satisfaction is important. Actually, I remember way back when, I started up my company, or when I wanted to become and entrepreneur, I always thought that I would be satisfied doing this. I had imagined myself being really happy and motivated and inspired by what I was doing.’ And so we worked really hard to include a lot of exampled because people related to them differently and different people speak to them. We thought that was a helpful aspect, you know, in the book.

Jason:  So what’s an example of someone with a really non-traditional structure of what you think a start-up should be? Because they had, let’s just say, unexpected constraints that they wanted. Maybe even constraints that you’d say, ‘That’s not even practical, how could you even put those constraints on yourself and still call yourself an entrepreneur’, and yet they did, you know, like let’s blow all this apart and see what you’re talking about, what you really mean.

Adelaide:  So, one example that I think of that is really interesting is, and what we are particularly fascinated by is how entrepreneurs can really sort of embrace the creative challenge of growth and say, ‘I’m committed to my company, I’m committed to being an entrepreneur for a long time’, because I think that’s and increasingly popular motivation, ‘and I want to see how I can adjust my company over time as my life changes and in response to my needs and how my needs are fluctuating over 10, 15, 20 years.’ So, there’s an example of a ceramasist that we interviewed and talked to and she had really interesting story.

She started in New York, and she started, at first she had been an architect and you know, was contemplating, ‘Do I really want to be an artisan? Can I make a living doing this?’ She had come from a family where you know making money and a certain level of success was really important to her. So, the first iteration of her business, what she started, she had a warehouse, she had an entire production crew, she had a big staff, they were wholesaling to lots of different accounts, they were making very high end dinner ware. She loved the artwork of it and the artisanship of it and being able to do that, but she kept feeling like, ‘I’m having a successful business, I’m going to build this to really be as big as possible.’

Over time, she found that she wasn’t satisfied. The business was going great, they had amazing accounts, they were being sold in Barney’s, they had amazing press, they were getting a really huge following, but she wasn’t doing the work that she loved. Like you said before, she spent a lot of her time managing the business, managing the outsourcing, managing all f these different things and so she really looked at her business and said, ‘This isn’t why I did this, this isn’t why I took this risk, I want to have a more hands on roll in my company, I want to be making things, that’s what’s meaningful to me.’

On top of that, she actually needed to be flexible with her spouse. He had a job that moved them around the country and so having a big, you know, a lot of overhead in a specific city wasn’t necessarily advantageous. Then she started to have a family and she wanted to be able to see them as well. So, she sort of has run her company through a series of iterations and that has turned out for her, in her specific case, that one of the smallest iterations has been, not only the most successful and satisfying to her, but actually that her take home, right, so the company makes less revenue obviously, but she actually is able to actually take more money out of the company. She’s able to herself just as much with a lot less overhead and meeting a lot of these other very specific needs that could have been considered very committing for her business.

Jason:  Right. In other words, we’re always so focused on top-line revenue the BITA, that we forget like, but if you’re making a good living and you’re happy every day, isn’t that the point?

Amy:  Yeah, I mean I was thinking of another example, I think that’s definitely the point and I think that people, that’s the biggest complaint that people say I don’t love what I do and I’m looking for that perfect job. From out perspective, entrepreneurship has a lot of opportunity to create that perfect job for yourself.

But I was thinking of another great example with people who from the get-go have set up their company with being very deliberate around other interests in their life. What comes, one of the women that we interviewed has a very successful academic consulting practice and she outside of work, and she’s extremely talented. She has a love for singing and it’s a very big part of her life. So she was very deliberate in structuring her business in such a way that she figured out how many clients she would need to be able to deliver good work and to enjoy herself and to support herself, but that she would not be constrained by having no time to have this other passion in her life. She’s in business for over 10 years and she’s been able to pursue this hobby of her’s and it’s a huge part of her life while growing a very successful business that is very manageable and has kept her very satisfied and happy.

I think in interviewing many of these women, it’s so exciting to uncover all of these success stories. When I mean success, by the entrepreneurs defining themselves as successful because they felt really satisfied. We were really excited to be able to get this book out to a lot of people and in a lot of people’s hands so they can see that there is a possibility and there is a possibility for you to do this on your own terms and define what success is going to mean for you and your business.

Jason:  Yeah that makes sense. I know a lot of people like me who are technical or engineers and then the business starts growing and of course writing code or doing that sort of thing is one of the first things that you have to give up because there’s everything else and you’re the person who has to do that. And it’s not fun. Typically if you love writing code, then you love writing code probably more than everything else. And so the idea that it’s OK to sacrifice something like top-line revenue growth in order for you to do something that you like and therefore maybe be happier and not get burned out, etc., it makes sense and yet almost no one does it anyways, so it’s really heartening to hear people who do it.

On the other hand I’ve got to push back a little bit. I’ve always heard things like, ‘If your business isn’t growing, it’s dying.’ It does seem like when you look around, that does seem like it’s often true. You look at larger businesses especially, where they’re unable, based on bureaucracy or some other reason, to innovate or grow and it does feel like stagnation. Stagnation is the beginning of the end. They do seem like they’re just there. There’s a lot of companies that are effectively in the living dead in the tech world and elsewhere. And so that does seem like a problem. It’s almost like you’re living off the interest of your savings if you’re not continuing to grow and innovate and expand like that. You can’t just live off the interest, the world changes around you and if you don’t react to it then what? How do you respond to that fact that that stagnation is really the beginning of the end?

Adelaide:  I’m glad you brought that up because I think that’s really true. I think that for all the entrepreneurs we spoke and the conversations we hand and the conversation we want this book to help generate is to adjust the definition of growth a little bit.

Right, so the way that we think about growth and the way I think a lot of these entrepreneurs do too is less replication and more evolution. Instead of saying, ‘Hey, I figured this out,’ right, so now I’m going to push back on the definition of stagnation a little bit. Because for them, for a lot of the people we talked to saying, ‘Hey I figured this out, let me now figure out how I can do this a thousand times, a hundred thousand times, a million times, get more users that do basically the same thing and slowly modify our image and add some nice services or what have you’, that to them felt like stagnation. Because, ‘I’ve already done that. I’ve already conquered that. We figured that out. It’s not that interesting to me to just now pursue doing that more.’

So a lot of them, there’s one woman that comes to mind, she’s actually a textile designer. I actually think a lot of people in sort of that Etsy handmade world run into this challenge too, right. They have this principle of things being handmade which puts a limit on the business. So she has evolved her brand and her company in a really interesting way so she can stay creatively challenged and that has been the goal. So instead of saying, ‘How can I get this piece of fabric in every home across the US and make a partnership with Martha Stewart or Wal-Mart or what have you’, she has left that part of her business intact and according to her handmade principles, and then has pursued a lot of publishing and has become a lifestyle brand pushing herself in other directions.

So now she has different books and other kinds of products. She’s manufacturing with people overseas to provide jobs there, though still staying with the handmade, but being able to scale a little bit differently. So I think, you know, I don’t many entrepreneurs who are satisfied not figuring something out, not doing something new, not pushing themselves or challenging themselves. But I think that there’s a way to do that that doesn’t necessarily mean you do it and you do it again, and then you do it on a bigger scale. I think that evolution and figuring out how to transform your company has been the growth path for a lot of these people.

Jason:  But isn’t’ that scary, too. You figure out, it’s hard enough to make a business that makes any money; where revenues are in any way higher than expenses, is actually really hard. You finally crack that, even a little bit, and you finally have that and then you’re saying, ‘Yeah, but in order to be happy you’re going to have to kind of do that again, and maybe you’re coming from a stronger position because you have existing customers and you have more knowledge about the market, and you have revenues to fund some of these new ideas, even if they don’t work out.’ But still, it sounds like, ‘Oh, great. Now I’m kind of back to the hard part, which is trying to make that number bigger than that number.’ It sounds like a tiresome existence.

Adelaide:  Well, perhaps. But I also think it’s really exciting and challenging, right?

The one thing that we haven’t spoken about that I think is true for more of the people that we’ve spoken to than, and actually, I think it’s true for the majority of entrepreneurs these days, but I don’t know that it gets talked about quite as much. I think more and more people are choosing entrepreneurship as their career path. This is what they want to do. I want to work for myself. I want to work on my own terms, ‘cuz I know I can create meaning. I know that I can create satisfaction. And it’s not easy. It’s definitely, that is the creative challenge of being an entrepreneur. But I think that having this long term view of, ‘How can I continue to employ myself and run a company that’s meaningful and profitable and challenging, and provide for myself over the next how many years?’ I think that’s a very different question than saying, ‘How can I establish a successful company that is valuable, not just to me but to potentially other buyers.’ So, it’s just a very different goal and objective, and I feel like you would grow it differently.

So if we were to say to most of the entrepreneurs, you know, ‘You figured out something. Now how do you feel about doing this for the next 15 years, just doing what you’ve done at a higher volume for the next 15 years?’ I think a lot of them would want to leave that company at a certain length of time, because it isn’t quite as interesting and challenging as what they have the opportunity to create if they are able to go and continually evolve their company. Amy, what do you think about that?

Amy:  Yeah, you know, I agree with what you’re saying. And some of it is just about the pace. I think that for some people if they have sort of a frenetic pace to hit, certain milestones very quickly, it’s very hard to maintain that kind of momentum. I think it’s like short burst, you know what I mean? Whereas, I think that if you look at your current business or your careers as an entrepreneur, on a longer term view, then I think you see that there is opportunities for reinvention and creativity in terms of what you do within the business and products that you have, and seeing new opportunities to develop new products for your clients. And, you know, things that, and if you’re open to that, as opposed to the replication model that Adelaide was speaking about, then you probably have opportunities to grow your company even more successfully, even though it’s in a different path, as opposed to sort of just a straight up type of movement.

Adelaide:  And I think that people, to the conversation that I think they have with themselves is, ‘I strongly prefer, would rather, I’m excited about the thought of doing something new, and using this platform that I’ve already created.’ It’s sort of wasteful to let existing values sort of go by the wayside, or not really leverage it as much as you can. So, ‘I’d rather use this existing platform to create something new, and to continually evolve what I’m interested in, than sort of take everything along with me. That is more interesting to me than to continue in a role that I know won’t be as meaningful, or as challenging.’

So, I think that oftentimes women that we’ve worked with and a lot of entrepreneurs we’ve worked with, I think that they have that sort of debate. What’s the cost of continuing to run this company in a way that may have that sort of more traditional trajectory. What’s the cost of that? Well the cost of that might be my satisfaction. So even if it means you’re going to do more reinvention along the way, I think that’s a welcome challenge.

Jason:  You keep mentioning women. Maybe you want to give a few words about your background there. The co-working space, literally the tag line is, ‘Where women entrepreneurs go to work, meet, and learn.’ The title tag on your website ‘Women Entrepreneur Network.’ To me I looked at this book and just felt like I wish I had read it 10 years ago, or 15 years ago, to me very little of it was only applicable to women, but that is where you focus. And so I wonder, is this kind of thing especially a women’s issue? Or is this general and it’s just because your backgrounds are in women entrepreneurship that that’s how you approached it? Or how do you feel about that?

Amy:  Yeah we think that it’s absolutely applicable to men and women and I think that these are best practices and these are things to think about when creating a business on your own terms. So that’s not a gendered issue by any means.

But our experience and our work comes out of working with women entrepreneurs and so obviously we used a lot of that experience to fuel the book where our philosophy came from. But what we found that there’s a much wider net out there of people that are starting businesses. Some of that’s from the recession, some of that’s just sort of the trend in America that people want to start businesses that are meaningful, that are sustainable. So that’s why it’s definitely not a book just for women, but I think that we had a lot of experience and a lot of connections to the community of women entrepreneurs.

I think, as an aside, most business books that have been written have really featured businesses run by men but they aren’t necessarily categorized as a book for men. It just happened to be that we featured women, although we’ve worked with men and had a lot of connections with male entrepreneurs over the years. It was just where our experience was and we thought it was a very interesting way to demonstrate how many women are being very creative and how they’re creating these companies that do work for them.

Adelaide:  I think also, that being said, we’re seeing the conversation about work and life in general. I think that’s a conversation outside of the entrepreneurial world that women sort of started. ‘Hey I’m juggling a lot of things and I actually want to be satisfied at work, outside of work, and I want work to be able to accommodate that.’ What’s been amazing over the last 15 years, is that lots and lots, millions of men have said, ‘Actually that’s what I would like too, thanks so much for getting this conversation started and changing some of the standards around this.’

I think the same has been true with entrepreneurship. I think it’s an older stereotype that women entrepreneurs care about their life outside of work. In our experience that hasn’t been true at all. I think it’s the way we’re wired as people to want to be satisfied and challenged and engaged in the world in a way that’s meaningful to us. And entrepreneurship is that opportunity to do it and historically more men have been entrepreneurs than women. So I think the challenge of doing that in a sustained and meaningful way is something that male entrepreneurs are extremely familiar with.

Jason:  OK. Yeah, that makes sense. It’s interesting because especially with the question of kids. It just forces the issue and it forces it really early.

I mean that’s what I found with my wife when she did her company and how she structure it. It’s like you just don’t have a choice, if you want to have kids you have to consider when you’re going to do that and why and how you’re going to structure other things around it or not. You have to make the choice. There’s lots of choices you could make, but you do have to decide what it is you want. It makes you think about other things outside of the business or shape the business around it.

There’s no automatic thing forcing them to ask these questions. I think you’re right that now the discussion is just everywhere. Now everyone, most people I find want to value things outside work. Having a lot of really specific ways to do that and have a company that thrives, which is a big feature of this book, is really valuable because it speaks to people wanting to do that. Of course, I still know a lot of Type A personality people who would say poo poo to all of this stuff and, ‘I work 70 hours a week and I’m happy and I just want money.’ Is that OK, or does it seem like it’s not true. I used to think that, and looking back on it, I don’t think I was right and I talk to a lot of Type A people like that who come to the same conclusion, like another example would be Andrew Warner, over at Mixergy, who is absolutely that kind of, you know, devoted to growth, money whatever the sort of stereotypical obvious stuff, and he admits, ‘Yeah, and then I got burnt out and I didn’t like it and it’s sucked and I’m not doing that ever again.’ So it’s actually pretty rare to find someone who is like that and then is still like that even when they look back and think that that was the right choice.

So, is it really ever the right choice, being that way, and if it isn’t, what do you tell people who are in the throws of that? It’s sort of like telling them, you should meditate and their like, you’re nuts. Even if they hear other Type A people, like Howard Stern, or somebody, talking about how valuable meditation is, they’re like, ‘Whatever, that’s just new-agey crap, I’m not even going to consider that argument.’ It seems like this can be the same, like on the one hand I wish I had read this book 15 years ago, and on the other hand I don’t think I would’ve, I probably would have just ignored it. So, how do you get through to people, especially people who might be listening to this right now thinking that. Right, like what do you say to them to sort of snap them out of that?

Adelaide:  I think that’s one of the hardest conversations that we have actually, and I think that’s the privilege of entrepreneurship, that people chose to work on things that they care a lot about and they chose to often do it in a way that is really exciting to them. I think that the entrepreneurs that we talk to that are sort of in this zone are, it’s one of our more challenging conversations, but I think that it’s easier to appreciate either from the outside, or from hindsight, the potential dangers of it. So, I’m loathe to sort of say that any one way is the right way or the wrong way to do things, and I’ll continue to look for that person who works in the manner that you’re talking and loves 30 years later is still excited about those choices and doesn’t feel like it came at a cost to them.

But I think what we see often is the costs that do come with that. There, even from a business perspective, there are a lot of costs that come from that. So we usually see that the more stress, the more burned out, the more siloed people are, the less creative they are, the less willing to, you know, the less able they are to discern the right opportunities from one’s that may be distracting or may just be sort of in the moment and kind of urgent. So, I think that there’s a lot of value, actually for your business, which isn’t necessarily the whole argument, but I think that there’s a lot of value for your business to have, to not have your business be everything to you. To have other elements and be able to sort of draw the line, take a step back and do a lot of, you know as people in the health and wellness field talk about, they talk about a lot of self-care and that kind of thing. I think entrepreneurs are notoriously bad at this, we abuse ourselves and we sacrifice so much all for our businesses. We sacrifice our personal interests, we sacrifice our time, and we, you know hobbies go by the wayside, friends go by the wayside.

I’m a strong believer in compromise. I think that in order to make, you know it’s impossible to kind of quote, ‘have it all or have everything’, so I think in order to make room for something things do need to be given up, but there is a danger and there is a cost to having, you know, if there is only one thing in your life, and that’s true if that’s work, or if that’s home or if that’s a hobby or if that’s a sport or if that’s you know anything. There’s a really personal cost to that and as an entrepreneur and being somebody who is responsible for the health of your business, there’s a real cost to your business, too.

So, I think the more that we can have the conversation about it the easier it is to sort of appreciate. And I think that, you know, for everybody the small steps are kind of the answer, right. So, it’s incorporating a little bit of, you know, balance and perspective that helps people kind of recognize like, ‘hey, maybe this isn’t the most healthy.’ It’s not even about health always, productive, it’s not always the most productive way to work.

Amy:  The thing I want to add, and I really agree is I think that you’re question is, how would you get someone who is Type A to read this who is in the throes of creating a business where they’re going to, they believe making a lot of money is the most important thing. The truth is, they are not going to read this book, because if they are at that place then they’re really enjoying themselves, or even if their miserable, if that’s, you know, it’s not until they get to a point where they’re really dissatisfied that this book would make any sense. It might be, sort of like the example you gave, ‘I’ve accomplished this’, and then they’re sort of like, ‘Well, that’s it? Now what? I achieved this goal and I have all this money, and I’m not satisfied.’ So then, I think, the timing is right for them to read the book. It’s like, ‘Well, if I’m an entrepreneur, and I’m always going to be an entrepreneur, if I’m going to start another business, maybe now I can do it differently. I don’t have to repeat the cycle of getting back into, you know, chasing after something that when I attain it I’m not going to be satisfied. Now I can actually be open to the fact that there are different ways of running businesses, and I can do it on my own terms, and think about it differently.’

So, I think it’s really people who believe that there’s more, that feel some level of dissatisfaction, that sort of are scratching their heads saying, ‘Well, I’m really working as hard, but something doesn’t feel right.’ That’s the type of person that I think is ripe for reading this book.

Jason:  Yeah, it’s too bad, right? It’s like, it has to be too late, and then you decide it’s time to fix that next time. And it’s too bad, because the book is here right now. You could read it right now, or you could decide this is important right now, but you probably won’t, like you said.

It’s like backup software. You don’t have it, and one time you lose a bunch of data, your hard drive crashes, and you go, ‘Crap.’ And then the first thing you do after restoring the machine is you go and get backup software. And you’re never going to screw that up again. But you had to go through that. You couldn’t, I mean, it’s obvious you need backup software, but you have to fail at that first before you will accept that. And I feel like a lot of business advice, not just this, is like that. Right?

Adelaide:  I think, Jason, what’s interesting is it doesn’t have to actually be at the end. We do work with people who were on their second time around and wanted to do it differently. But we work with more people who notice that slow burn of dissatisfaction, who just sort of say, like, ‘You know, this isn’t. When I’m asked about it or when I have a reminder, like this isn’t actually as ideal as I want it to be’, or the way they sort of talk about it is, ‘My business isn’t exactly the business I want to run anymore; or I don’t want to run it in this way. What can I do differently?’ And then they might decide to get rid of it, or they might decide to kind of overhaul it. I think that more people have kind of wake up calls during the process than after, at least in our experience, which I think is a good thing, because they get to leverage all that value and adjust their company to better meet their needs.

Amy:  And I think, Adelaide, those people that we’ve come into contact with, and we work with, and feel some level of dissatisfaction in the process, they have some sense that their goals for the business are beyond just money. They have personal motivations invested that maybe they wanted autonomy over their time or maybe they wanted a lot of creative freedom, and they sort of set up their business to do that, and it’s not achieving that. So it’s like, they feel the pain in the moment. They know something is off that doesn’t feel right, and they don’t want to just continue to build in a direction when it doesn’t feel right.

So I think that’s a pretty big distinction. They are really going into entrepreneurship to meet a variety of needs and they come to us often when something is off and they have the confidence that there’s a way to make it better. And I think that’s really admirable, because then you actually can be open to the advice, and really take ownership of the fact that you have this opportunity to change it and make your business really work in a way that’s going to be most satisfying to you.

Adelaide:  Absolutely.

Jason:  So, another big point we haven’t talked about yet here, that you make, is that entrepreneurs make short-term compromises that end up costing them. And I know I’ve done that, but on the other hand I don’t know if it was really a bad idea in the global sense.

So, what I mean is, especially at the beginning, you want so bad to get that big sale, or get that big customer name on the website, or add some feature, because you only have three customers, and they’re asking for something. And you might argue that in some global sense, or even in the ways we’re talking about right now, about compromises, that it’s a bad idea. So maybe it’s more relevant to what we were just talking about, maybe I’m working way more hours than I said I wanted to, to get it launched. And in some sense, it’s a mistake or a compromise, a short-term compromise, on what it’s supposed to be.

But on the other hand, I sort of feel like, yeah, it might turn out a year later that that sale ended up eating up too much time. Or, yeah, you didn’t want a business that was 70 hours a week. But then again, you’re here a year later. And part of that is because you worked 70 hours a week for a while, or part of that’s because you did that big sale, and it did give you a name. And yeah, maybe now it’s not a good choice anymore. But maybe you did need to make that compromise at the beginning. How do you judge that? Is it OK to make more compromises at the beginning and what makes it OK?

If you know it and you have a time limit on it, when should I be uncompromising in my values, what I accept, and my constraints? When do I have to say look it’s a living thing that I’m not even sure how it’s going to work yet. I have to be more flexible to let it do something or maybe get over a hump before I can really get it to a place that matches my constraints.

Adelaide:  I think this is a really big issue for entrepreneurs, but don’t get this wrong, we totally believe in compromises. It’s the name of the game. I think that as an entrepreneur, you’re always compromising. Prioritizing actually may be a better way for us to think about it where you’re always having to shift those priorities around; what takes priority right now.

I think that there probably is several ways that we can talk about this. One of the most things is understanding choice and the role that choice plays in making a compromise because a lot of new entrepreneurs, for some reason or another, don’t feel like they have the choice. The customer asks and they say yes. Somebody suggests that they should do something and they do it. I think that one big piece of what you’re talking about, when is it OK to make a compromise? I think a big piece of that is acknowledging that, ‘I’m making this choice for this reason. I will work 70 hours a week right now because it’s for this specific outcome. I know that I’m doing it, I know that it is something that’s less than ideal and which would hopefully help put an ending on it. I’m willing to do this for the next three months.’

I can give an example from our experience. So when we got this book deal and decided to interview 100 people, we’re running a business, the floor below us in our building became available so we decided to expand our business because it was the right opportunity to take. So in the course of 10 weeks, we doubled the size of our business, made a huge capital investment, traveled all around the country, interviewed 100 different people, and were running our business with existing responsibilities at the same time, and we were exhausted. It was a huge compromise and we sacrificed a lot of boundaries that we normally hold pretty rigidly. We knew that we were doing it and it was a choice to do it. We certainly look back on it and say, ‘That was insane.’ Would we want that to be the norm? No. But we made the choice and we knew that it didn’t have to be the norm. It was that sort of short-term that had a start date and an end date and it didn’t come to define the way that we do business going forward.

Amy:  I was thinking about how Jason, you asked, ‘Is it time bound?’ You know, in this particular example. We did look at it as this is a couple of months in which we’re going to sacrifice everything we setup the company to deliver to us basically, and what’s important to us. But we had a goal in mind. I think you believe that if getting that one client on your website is the most important thing and you know that it’s certainly going to require some compromises, I think it’s more of just, in hindsight perhaps it does or it doesn’t, I think it’s more of having the discipline over yourself and sometimes entrepreneurs have trouble with this in sort of saying that this isn’t going to set the pace and this isn’t going to set the standard of how I want to keep doing business going forward.

So there’s a lot of control that you have over the way you are going to structure your business, so that if you do in fact make one of these compromises because you believe it has long-term gain, I think it’s more of an issue of that and just reeling it in and saying to yourself, ‘Wait a minute, now how do I want to go forward?’ You don’t have to give up all of that control and opportunity, if a short-term sacrifice does make sense.

But sometimes it’s important to look at your business and evaluate if some of the short-term sacrifices that you’ve made in the past actually did amount to anything and if they were to the value that they thought and if they didn’t, that’s a really good learning opportunity for you in the future to evaluate potential short-term compromises that might come up in the future.

Adelaide:  I think that just in the places that we see the short-term or what they think is short-term compromises to become very problematic are things around how people spend their time, and then they pick up their head a year, eight months, two years later, and they’re still in the roll that they don’t enjoy. So I think that that’s sort of like a big that should be an area that people protect well, and are really thoughtful about when they’re planning to make a compromise or something comes up that they’re considering.

Another example that we talk to people about all the time is, there’s so many periods of uncertainty when you’re building a business, and so responding to that. ‘I’m not really sure how to move forward, so let me partner with some one who does. Or let me hire this person or bring this employee in or this consultant or something like that.’ And so I think that decisions or compromises that are often driven by uncertainty, or adding major components to the business or major things that can redirect the business. And then those are often times where we see find it to be a little more problematic. It felt like a shot term compromise, it felt like a short term fix or it felt like something that was really necessary at the time, but it wasn’t, but it’s come to define the direction of the business and the standard of the work that you do.

Jason:  OK. Maybe this is sort of a good way to wrap things up. When you talk about what’s going to make you happy or what’s important in your life, or how to prioritize rather than compromise and all that kind of stuff, it sort of comes down to what’s going to make you happy, and what’s important to you, and its really hard to decide what that is. Like I’m still am not sure that I fully know what things to put in place to make me happy. And it’s not one of these things you can A-B test, watch some metrics and decide. It’s something you just sort of have to arrive at. And if you don’t know what those things then you’re still guessing and it doesn’t seem like it’s, it’s still up in the air even when you make a conscious choices whether that’s going to achieve what you really want.

So how do you do that? How do you decide the things that you think will in fact be fulfilling and all that sort of thing. Or do you have to just get in there and have a mentor that you trust to help you through that, how do you do that?

Amy:  I think that it’s interesting that you use the word happy. Because I think that happiness is obviously very important, I think Adelaide and I usually frame it terms of sort of satisfaction.

Jason:  I forgot that in New York, no one’s allowed to be happy.

Amy:  No, I think it’s a pretty big concept you know what I mean. I don’t know if you can arrive at happiness as opposed to like an end goal. Is it something like now I’m happy or is it feelings that you have a lot of the time. You know what I mean, it seems very big.

Jason:  Yes, OK. It may have just as much to do with yourself. Maybe a better way to say it is this. Sometimes you’re making a choice at the business and you can feel that it’s going against some kind of feeling. Which is sort of indicating it’s against something that’s probably pretty important actually. And I think entrepreneur’s, I certainly do, we feel like, ‘This is best for the business so I need to do it anyway.’ Or, ‘this is how business works, even though this part is not how I would normally do it.’ I’m not comfortable with this, but this is how it works quote end quote, ‘How it works.’ Like we know, and like that’s a thing that exists some where. Like platonic forms out there that this is how it works.

But that’s kind of the thing, ‘this is how it works, so ‘m going to do it any way even though it’s against the grain, but on the other hand, sometimes the right thing to do is against the grain.’ Because you don’t always have exactly the right feelings about things. How do you know when you should be listening to that little voice which is probably the truth about your self. And when you have to say, ‘Oh wait maybe this is in fact better, for whatever global things I’m going for.’ How do you make that distinction?

Adelaide:  So I think that I would think about it in two ways. One, I think that this is where a high degree of self awareness comes in. And I think as entrepreneurs, there’s a lot at stake, there’s a business at stake, there’s employee’s at stake, and I think that as a leader it’s your responsibility to have a high degree of, and if you don’t have it to start with, cultivate a high degree of self awareness. But I think that as leaders a lot of us should have red flags around what are our sort of typical behaviors.

For example, and I’m lucky to have a partner who I have a wonderful partnership with and can help bring these shortcomings to my attention. But I’m historically somebody who can be a little bit resistant to change or being really quick to act on something. Those may sound contradictory to each other, but I have a high degree of urgency but a resistance to overall change.

So when something is coming up and I’m saying, ‘I don’t know about this’, and it’s because it’s coming from one of those trigger spots. It’s coming from a place from where, historically, I have a weakness or I need to watch for where I’m overly sensitive. We put those decisions in one category. For those kind of decisions we often times get a lot more data. So how can we more objectively evaluate this decision, taking into account the fact that you’re not going to want to do this because you don’t like changing everything. So I feel like there are those kinds of decisions.

Then there’s other decisions where it’s not about me as a person, but it calls into questions one of the fundamental underlying principles that I think are important as an entrepreneur and for our business. So the things that we talk a lot about and hold to be really true are: How do we spend our time everyday? Is this going to fundamentally change the way that I experience my day today in a way that’s going to be dissatisfying to me. Is this going to fundamentally change what we’re known for? Is this going to pull us totally off mission. Is this going to take us away from our goals?

So these are some areas that we never want to cross unless there’s good reason and we’re excited about it. But if it’s feeling wrong and it’s violating one of those fundamental principles, then that’s one thing. We often say, ‘No,’ in those cases because it doesn’t always seem best for the business It’s hard to understand how things can be best for the business sometimes if it’s not best for the people running the business when those people plan to be with the company for 10 or 15 years. That equation usually doesn’t add up to me.

On the other hand if it’s something that’s my own personal issue, then we approach it a little bit differently. So I might encourage people to think about when you get that feeling, ‘This is going against the grain,’ kind of think about which camp this is in. Is this really violating why I became an entrepreneur, what I like to do every day, what I want my business to be known for kind of thing. Or this is violating the ethic of how we run our company. That’s a pretty major compromise to me. And if it’s a personal limitation, perhaps you need, if you’re in New York, you need therapy. Amy, what do you think?

Amy:  Yeah no, I really think that a lot of it is about self-awareness and trying to put into place as many things in your life that do bring you joy and happiness and fulfillment and creating room for those things in your life. I think that only each individual can answer that. That’s what makes us really interesting. I think it’s something that you don’t really arrive at. It’s something that evolves over time.

That being said, I think that we would argue pretty strongly that being an entrepreneur can really provide the opportunity for you to find many things in your life including your business that do make you feel really happy. Especially if you do that in a very thoughtful and deliberate way.

Jason:  All of this comes down to having somebody else, who you trust, who also knows you, and knows what things are valuable to you, who can actually give you that outside perspective. I find that most of the time when you get advice from people, from me included, you’re sort of getting advice that’s right for the person giving the advice. Not necessarily for the person receiving it. And of course that’s true on something like a blog or podcast where it’s one to many. So of course it can’t be personalized. But even when someone’s sitting down with you, there’s still sort of talking about there own experience rather than really trying to understand what the other person really wants out of it.

A co-founder can help and another thing I found, there are sometimes spontaneous and sometimes organized groups of entrepreneurs who decide, like maybe a group of four or six, ‘We are going to be our own support group. We’re going to meet once a month. We’re going to really treat that as golden and important. We’re not going to sometimes not meet. This is going to be religious for us. Everything we say in here is 100% private, and we can say absolutely anything without judgment. We’re actually going to get inside each other’s stuff and help each other through that because we’re the ones going through it together. We understand implicitly the life we’re trying to do and we know why we’re doing this for each other.’

I know quite a few people who do that and all of them swear by it and say that they would never not have that again. So, maybe your co-founder can do that or maybe you can find one of these groups. Co-working is a way to find some of those people. Just working next to people is not enough to get that kind of depth, but it absolutely is a way to find some people who your are sort of naturally compatible with and therefore want to form a deeper thing with. I think you kind of need something.

The people I know, and, again, I put myself in this category, who started a company as solo founders. That’s fine, but you need some component of this. You need somebody who has your interest at heart and knows you enough to be able to do that, who is not so close to the everyday things, that they have perspective to force you to see some of these things or help you make some of those decisions. I think everybody needs that a little bit.

Amy:  I think we couldn’t agree with that more. I think the cost of isolation is pretty huge on so many fronts, and I think you gave great examples whether it’s a group of a couple of people or you have the good fortune of having a co-founder or we have come across woman who have a business buddy. It’s like having a coach, but it is really important for you to have someone to bounce ideas off of, but in that moment, that person, like you said, really has what your best interests are in mind, and that’s difficult. I think it’s really wonderful to be able to find those people and trust those people. I think that everyone benefits and grows and it makes your business a lot more fun.

Jason:  Another thing you can do is, for the majority of people who are giving you advice who are not very knowledgeable about your personal situation and are really speaking about themselves most of the time, you can still control who those are, and if you’re building a business where it’s supposed to be a two person business forever because you don’t want employees and you just want to work with your co-founder. Yet, you have an adviser or an investor or you read certain blogs, of course there are things that you don’t know yet, you can simply be selective and say. ‘I’m going to intentionally pick people who I know are all ready more aligned with what I believe. They’ve built a business like the one that I’m trying to build. So, clearly they have at least the experience and probably a lot of the personality traits that I have.’

In other words, you can sort of decide to pick folks who are more aligned with you anyway so that when they speak about themselves at least it is more likely to actually be the right choice for you too.

Amy:  Yeah, absolutely.

Jason:  Great. I hope that some people who would normally turn their noses up at that there are many things in life that are important besides top line revenue growth will maybe give it, at least a thought, and consider that there are other things that are important and fulfilling, not happy, but fulfilling. Also, I hope that next time I get to be called Jay because I noticed you guys call each other Am and Ad, which is awesome because Amy is such a long name that needs to be shortened so you can just fit it. Any closing thoughts?

Adelaide:  No. Thank you for the opportunity. It’s really exciting to be able to talk about it. We’re eager to hear from people and hopefully we can continue the conversation on Smart Bear. We really love talking about growth and what it means to people and how they’re running their business and what their experiences are. So, we’re looking forward to more conversation.

Jason:  You guys are running some kind of contest now where people can get free coaching from folks, right?

Adelaide:  Yes, through Sunday, so I’m not sure when this will close. It’s a business makeover contest and you can enter. The details are actually on our blog which is www.ingoodcompany.com. If you win you win more than eight hours of free consultation with nine business experts, so everybody from finance to social media to productivity to marketing to pricing. So it’s a wonderful opportunity for people who are wanting to give their business a little tune up or people who are even just thinking of getting started.

Jason:  OK. Great. Well, thanks a lot for being here and I thought it was really interesting.

Continue the discussion in the comments!

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“WE STARTED THE TREND”

“Wherever you hear companies talking about Managed WordPress Hosting, they are following our lead.”

This is how one of our competitors attempts to differentiate and compete with us at WP Engine. Is it effective?

Most startups insist they’re “first” at something. As they should — what’s the point of a new company that adds nothing new to the world? But is it a good thing? Does it make you better than your competition?

On the surface being “first” sounds impressive, implying innovation and leadership. But upon reflection, it’s not.

Google wasn’t the first search engine, the iPod wasn’t the first mp3 player, and DropBox wasn’t the first shared filesystem. Yet they are the market leaders. Indeed, their market’s greatest innovators.

Being first does imply innovation, but also faults and weakness. The first electric car, while impressively innovative, was pretty bad by most standards — short-range, sluggish, unattractive, and constantly in the repair shop.

So too with software — “v1.0″ might imply novelty, but it also implies “buggy” and “incomplete.” Who wants their business to depend on a v1.0 product?

Even if you consider WP Engine to be nothing more than an imitator of this competitor (we’re not, but that’s a story for another time), the electric car analogy is apt, because in fact we’re an improvement in almost every way.

This competitor had 40 minutes of downtime last month; we had 0 (according to Pingdom, an unaffiliated 3rd-party). We’re 30% faster at delivering HTML (also Pingdom). Our security service is better — we guarantee cleanup of any hacks while this competitor simply claims they’ve never been hacked (though we’ve found malware in customers of theirs who switched to us). Our support is more responsive and knowledgable because we employ more WordPress experts per 1000 customers than anyone.

Those are tangible competitive advantages; being “first” isn’t.

In fact, being first is a shackle because you’re stuck with legacy support — features you thought were important but aren’t now, grandfathered customers who are no longer profitable, and a reputation that’s hard to revamp even if your company has in fact changed.

Worse, being first means you make all the mistakes in public, for all to see. New competitors get to swoop in afterwards with the hindsight that you created — in pricing, positioning, marketing, features, design, … anything. They get the running start without all your baggage.

Now there are situations where being first is indeed a massive advantage. This exception arises when you’re not only first, but able to expand fast and continue innovate. Early mp3 players didn’t do this — they didn’t get huge traction and weren’t creative in hardware or design, which meant Apple had the space to innovate in design while the market was still largely available.

But McDonalds and Ford were first and kept their leads, because they never stopped innovating in process and product, constantly driving down costs while adding new desirable features, using their lead to fund even stronger growth.

Amazon is the quintessential example in the hosting industry. They didn’t just put “cloud computing” on the map, they’ve never stopped lowering prices while expanding both depth and breadth of service. If they keep it up — and there’s currently no reason to think they won’t — it’s hard to see how anyone could overtake them. And so far no one has come close, though at least two multi-billion-dollar companies are trying.

So yes it can work, and a well-funded startup combined with a stellar team and bit of good fortune can occasionally pull it off. But most little companies aren’t in that position, and it’s often not the best risk/reward position anyway.

What this means is that being “first” isn’t an end in itself — it’s not an advantage, not a feature, not a benefit the customer can experience. It’s a means to one of those ends — it can be levered into market dominance or it can be a manicle that locks your company in a box you can’t get out of.

It’s OK to be proud of being “first” at something, and you should be. But like being “disruptive,” being “first” isn’t necessarily desirable.

In any event, it’s not a competitive advantage. It’s just history.

Let’s continue in the comments — when is “first” a benefit or a drawback?

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It’s a big decision to make your first hire, because what you’re really deciding is whether you want to keep a lifestyle business or attempt to “cross the chasm” and maybe even get rich.

Assuming you really are in the market for another pair of hands to screw stuff up worse than you already are, the question is how to acquire resumes, how to pare them down, and how to identify someone who is going to work well in your company.

There’s already a lot of great advice about hiring at little startups. Before I give you mine, here are some of my favorite articles, in no particular order:

• Smart, and gets things done by Joel Spolsky — The classic guide to what to do during the interview and how to know whether to “hire” or “not hire.”
• Why startups should ALWAYS compromise when hiring by Dharmesh Shah — There are many attributes you’d like to see in a hire, but compromise is necessary; here’s how to do it.
• Five quick pointers on startup hiring and Disagreeing with Entrepreneur Magazine by Dharmesh Shah — Assorted tips, all important.
• Hazards of hiring by Eric Sink — Great tips, including some specific to hiring developers (for more on the latter, here’s another).
• Date before getting married Part 1 and Part 2 by Dharmesh Shah — A strong argument in favor of working with a person rather than relying on interviews.

I’m not going rehash those or attempt a “complete guide to hiring.”

But I do have some fresh advice you might not have seen before:

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I can rip any business idea to shreds.

Take NetFlix: The costs of inventory logistics, millions of non-technical customers, the Postal Service, and loss from wear and delivery will make profit impossible with a reasonable retail price. Movie-watchers are accustomed to the immediate gratification of browsing and selecting. People will copy movies, pissing off suppliers. Blockbuster will duplicate the model and undercut the price, combining the convenience of home delivery with the equally convenient option of store browsing and returns.

Terrible idea that could never work. Except that now Blockbuster (who did copy it) is bankrupt and NetFlix turned a profit of $60m last quarter, which is more than Blockbuster was doing in its heyday.

I suppose if your goal in life is to be right, you should bet against every startup, certainly against any novel ideas. You’ll be right much more often than wrong. Congratulations. You’re right, and utterly useless.

The goal of the entrepreneur is not to be “right.”

It’s to construct with humility. To listen and talk simultaneously. To infect customers and employees with your peculiar disease. To live to fight another day. To acknowledge being wrong before the fault turns fatal.

To realize that even if a particular venture is a “failure,” it never is. I’ve never met a “failed” entrepreneur who doesn’t proudly declare they’re better off now: developed skills they never thought possible, learned what makes them excited to get up in the morning, came face-to-face with their fundamental limitations, and now more confident than ever in what they’re capable of, regardless of the future shape of their career.

The Lean Startup movement also values learning and experience over “being right,” specifically casting this concept as “running experiments.” And the great Francis Crick (Nobel-winner for discovery of DNA) posthumously agrees with that analogy:

“The dangerous man is the one who has only one idea, because then he’ll fight and die for it. The way real science goes is that you come up with lots of ideas, and most of them will be wrong.”

Real science is mostly being wrong, but staying vigilant and honest enough to continue being wrong until you’re not wrong. So it is with dating. Or startups.

The problem with armchair criticism is it’s so easy. Which was easier — my rant on the perils of the Startup Genome Project or the effort in collecting and analyzing the data for that project?

Of course it’s easy. Is it even theoretically possible for the Startup Genome Project to not have holes for me to poke at? Does that really make the project dubious? I stand firm that my criticism was sound, but… so what?

Designers want to be “right,” but have to temper that with analytics data. The true masters are those who embrace metrics as an incontrovertible goal while also being creative enough to retain the aesthetics, creativity, and philosophy which makes their craft an art.

Programmers want to be “right,” but have to temper that with getting things built and shipped, even before it’s ready, even with bugs, willing to build features pulled by the market instead of pushed by internal rationalization.

Backseat advisors and pundits (like me) want to be “right,” but have to temper that with the more important goal of inspiring people to be a better version of themselves instead of indoctrinating them with our own biases and experiences.

But as a founder, you still need to listen with half an ear. Sometimes you’ve been blind. I still resist opposition to my ideas, more than I know I should. I still hate being wrong.

But it has to be possible to be able negate you, otherwise you are certainly pig-headed. As the CEO of WP Engine I feel that most days are filled with more contradictions than construction — balancing customer needs with internal costs, following our nose against what competitors are doing, or staying true to our “vision” while also flexing as we learn what the market wants and even what we want for ourselves.

It’s easy to criticize but it’s just as easy for you to dismiss criticism without consideration. That’s equally hazardous.

How do you tell the difference between useless and constructive criticism? Let’s continue in the comments.

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This is a guest post by Mark Anderson, owner of lifestyle business Andertoons which produces all the awesome cartoons I use on this blog. He created a custom cartoon for me, and I thought it would be interesting to get a behind-the-scenes peek at how cartoons are created.

The custom cartoon began with Jason sending over an early draft for an upcoming presentation he thought might need some livening-up. The general topic was “honesty,” so after finding some quiet, I set my brain chewing on it.

The thing about writing cartoons is you never know when, how, or if you’ll get an idea. It can be frustrating, but I’m comfortable with it.

I can write, even under a tight deadline, because I’ve written thousands of cartoons, and I’m confident that they will continue to flow.

Normally I begin by taking a look at my topic from all angles:

When would the topic be bad? When is it good?
What are phrases that include my topic?
What rhymes with it?
Who is associated with it?
Can I combine ideas?
Where can I exaggerate?
How about animals?

Then you sit and stare and sit some more until ideas begin to come into focus.

I came back with these three ideas:

1) Manager behind desk to applicant – “Your resume says you’re distractible, you like to gossip, and you sometimes oversleep? You’re hired!”

2) Businessperson giving presentation with slide showing tube of “Anderson Wart Remover.” Presenter says “This ‘warts and all’ approach is perfect for us!”

3) Ad exec giving presentation for product with tag lines reading “Lowest Rating in its Class!” and “1 out of 5 stars” and “What a stinker!” Person at table comments “This might be taking that whole honesty thing a bit far for me.”

Number one conforms to the rule of threes, and there’s your reversal at the end. Number two relies more on the visual to set up the gag, and then the caption knocks it down. And number three is an example of exaggeration. These are all more or less standard jokes that you learn to recognize and create.

Jason liked them, but worried that they were wordy and might slow down the planned pace of his presentation.

Jason sent over some more info, and I suggested he consider using the cartoon as the opening image of the presentation; something for the audience to enjoy while they came in and found their seats.

He liked that idea and I continued work on a few additional concepts taking some different tacks:

4) Pinocchio with elongated nose sitting in audience says to person next to him – “This is the honesty in business seminar, right?”

5) Management type in meeting to employees – “Honesty is big right now. See how we can spin that.”

6) Businessperson giving presentation showing up trending sales says to workers – “Not only is honesty the best policy, it’s making us loads of cash!”

These gags play more with association. Pinocchio makes sense, he’s a nice visual, but the gag feels weak. Number six is good, but the greed is iffy. Number five, which Jason chose, is a reversal, and I was careful to keep the surprise at the very end (it’s the second to last word, in fact) of the caption. It’s also one of the shorter captions, and brevity is wit.

With the caption agreed on, I got down to sketching the art for the cartoon:

The goal is to quickly communicate the scene. Where is it? Who’s in it? What is this about? You learn a visual shorthand to get those things across and keep the read moving.

For example, the desk and chairs are only partially drawn, but there’s enough to set the scene. The person speaking is clearly indicated. The scene reads left to right smoothly. These are all things a cartoonist needs to consider.

I’ve been doing this a long time, so it only took maybe 15 minutes from my initial sloppy sketch (I looked for it, but apparently it’s been removed to the recycling bin of the ages) to the second cleaned up client-ready sketch above.

Normally my cartoons have a typeset caption underneath, but Jason suggested a cartoon speech bubble to allow for a larger font and easier reading. I don’t particularly like bubbles, but Jason has given his share of presentations, and if he’d prefer a speech bubble, that’s fine.

Jason approved the cartoon and I moved on to the final ink:

This part goes quickly because all of the heavy lifting of writing and sketching is already finished. The only hiccup being a slight skew in the speech bubble (see why I don’t like them?) that I fixed with a little Photoshop warping.

After the ink is the way I want it, I move on to shading:

When I’m doing cartoons for Andertoons’ inventory, I normally shade using markers. But for custom clients I use a set of sampled markers I created in Photoshop. It’s less organic, but when used in layers they allow for easier editing to a client’s taste.

After the ink & shade are complete it’s time for the custom cartoon cherry on top, the caption:

Normally I use Tahoma for a caption underneath, but that kind of font doesn’t fit a speech bubble. I used a font I had made of my own handwriting to finish things up.

After a final spellcheck, a double check of the dimensions, and one more good long look, the cartoon is emailed over and, hopefully, everyone is happy.

So that’s how it works. I hope you weren’t expecting anything wild or zany. The truth is comedy is serious business, and only those cartoonists who approach it seriously end up with a career drawing funny pictures.

If you’d like to commission a cartoon of your own, please check out my custom cartoons section at Andertoons.com. And thanks again, Jason, for the opportunity not only to draw you a cartoon, but to talk to your readers more at length than my regular captions.

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