Startup identity & the sadness of a successful exit

The first emotion I felt after selling Smart Bear was a profound sadness. Not depression — not hopeless or rudderless — but a pure sadness, when your lungs sink into your belly, the punch-in-the-stomach of discovering your dog was hit by a car or that your dad is terminally ill.

“What the fuck?” I thought, “Why am I feeling this? I’m supposed to be feel… happy? I guess? Something other than this.”

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“Because that’s the way it’s done” — should a founder listen?

They told me I couldn’t sell to The Enterprise with a silly company name like Smart Bear.

They told me I couldn’t sell to The Enterprise without a human sales force using Salesforce.

They told me I couldn’t sell to The Enterprise over GoToMeeting, with a demo and no slides, from a geek with no webinar.

They told me I couldn’t sell to The Enterprise with amateur design and a small-company, human voice.

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How do you tell a non-technical person that they can’t understand?

This is part of an ongoing startup advice series where I answer (anonymized!) questions from readers, like a written version of Smart Bear Live. To get your question answered, email me at asmartbear -at- shortmail -dot- com.Frustrated Engineer writes: I’ve been writing code for ten years, recently promoted to a position where I have to…

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Better for whom?

All founders define their business as being “better” than the encumbents. But most don’t say anything beyond that. Being specific about “better” leads to the good stuff.

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A compass is not a map

A compass tells you which way is north, not whether you should be heading north. So what *is* the map to startup success?

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Austin in San Francisco

In an era where more people can devise their own lifestyle and career than at any other time in history, it’s interesting to ask how a startup can support and encourage its employees beyond a paycheck.

In an era where job-hopping is a badge of honor instead of a mark of disloyalty, it’s interesting to ask how a company can retain great employees over significant stretches of time.

In an era where “friend” means one of 852 on Facebook, it’s interesting to ask what a friend really is.

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My simple ways to be a happier, smarter 30-something

Do this stuff, and I guarantee you will literally be happier, smarter, more productive, live longer, and most importantly you will not feel like you’re missing out on life.

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Entrepreneurial Re-entry — Businesses for Moms

What does workforce re-entry mean for the modern mom? And startups in particular?

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How to get attention from internet celebrities

I get a constant stream of requests to look at new startups or to announce something that a startup just did. But most of it is spam, and I don’t have much time even for the non-spam. Here’s how to pierce my email firewall and get some attention.

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But I know that he knows that I know

When two people in America need to make a boolean decision and a coin isn’t available, the go-to method of problem resolution is Rock, Paper, Scissors. Generally people feel this game is fair, meaning there’s an equal likelihood of each participant winning, losing, or tying. And of course if you’re an academic who believes Big-Oh embodies…

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Teeny bit of traction — what next?

After a year of work, my startup is now doing about $6,000/mo in revenue and $3,000/mo in profit. I just quit my day job to work on it full-time, and I have a few thousand more dollars I can put into it.

What should I do next?

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The rise of the “successful” unsustainable company

We’re building too many unsustainable companies. Some are obviously silly, but the real danger are the ones which seem like legitimate business models, but which cannot operate at the scale we push them to, particularly post-IPO.

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Why “saving money” and “ROI” are probably the wrong way to sell your product

Spending $1 to make $10 sounds like a can’t-lose proposition. So why does it never work? And what should you do instead?

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