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Big & Small Ambitions.

I have big and small ambitions.

When it comes to revenue and profit, I’m going big.

I want to be financially comfortable, and I like nice things… but more, the game of business is powerfully motivating, with profit as the ultimate scorecard.

Part of that ambition comes from watching peers and contemporaries grow companies to 7- and 8-figure annual revenue heights.

It motivates and inspires being in such a community. The ambition is contagious.

I guess in that way, ambition is like air: when you’re submerged in it, you can’t help but breathe it in. Continue reading…

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Working “street style”

Our workflow inside CrewFire/SimpleCrew is extremely… “fluid.”

I was speaking with a friend about how we work yesterday, and he described it as “street style”.

I laughed, and then quickly wrote that down. I like it.

Here’s how we work: Continue reading…

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How our niche-product (SimpleCrew) pitch has evolved over time.

Had a random thought today: it’s interesting how our product pitch for SimpleCrew has evolved over time.

I’ve explained to folks before that, while the actual idea for SimpleCrew hasn’t changed since we started 3 years ago, the way we’ve described SimpleCrew has changed and evolved a lot over time.

Back when we started, we were describing SimpleCrew as a “field team management application”: Continue reading…

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Silicon Valley Vibe

I’m writing this post from HackerDojo – a coworking space in Mountain View, CA, one of the towns that makes up Silicon Valley, between San Francisco and San Jose.

It’s been a nice couple weeks visiting friends and family, from Detroit, to Seattle, to San Diego, and now the Bay Area – San Jose, Stockton, San Mateo, Mountain View.

I love all these towns. Continue reading…

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Why I’m Writing

Just a few weeks into this writing challenge, I’ve found that I’ve been enjoying it more than I would have imagined before, and I think I know why.

When I set out on this writing challenge, an honest inventory about why I was writing would have revealed an extrinsic motivation: I wanted to build a platform of influence, an audience, and me admired and respected in the same way that I admire and respect the writers, bloggers, and thought leaders I read.

Lately, I’ve found that I just come to love the flow of writing, the satisfication of thinking through ideas in my head more thoroughly, and the feeling of getting them “on paper.”

I have to give credit here where it’s due. A few weeks ago, I listened to Maria Popova of doing a fan Q&A for Tim Ferriss’s podcast. Continue reading…

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Writing through the ups and downs.

A few years ago, I picked up a little habit that has helped me navigate the hard times in life more gracefully, and appreciate the good times in life more thoroughly.

It’s a simple trick: whenever I feel an intense low or intense high in life, I write about it.

Whether it’s the stresses during a rough patch in a relationship, the elation after hitting a business milestone, the deep feels after a close friend’s wedding, or any number of emotional instances – when I feel a strong emotional pull in one direction of the other, I fire up Evernote and write through my thoughts.

I’ve found this practice to be helpful in a bunch of ways. Continue reading…

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The hardest part about building a million-dollar business is getting to 10 paying customers.

When Mike and I first started SimpleCrew in 2012, our friend, mentor, and investor John Campbell gave us some sage advice.

He reminded us that, while we may have our eyes set on the distant goal of getting to $1M ARR (annual recurring revenue), we shouldn’t let that goal burden us in the beginning.

Going back to the math of subscription software and recurring revenue, the $1M ARR threshold is crossed at just over $83k MRR.

When you’re just starting out, just a couple small town sons of Appalachian turd miners working to bootstrap your first software product, those numbers can be a burden. Big, distant, and seemingly unattainable.

Keep breaking those numbers down though, and they become more digestable. Continue reading…