Bootstrapper’s Milestones

Celebrating Two Years and Two Hundred Articles

Decision-First AI
Corsair's Business
Published in
4 min readAug 11, 2016

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Two years ago, as LinkedIN reminded me today, I began to chase a dream. In August of 2014, days after ending a month long sabbatical, I made a decision to invest my most limited and treasured resource — time. These days time is often overlooked in a world of million dollar angel investments and multi-million dollar venture rounds. But, as I noted before, I am a bootstrapper and for us time is always more precious.

When I say I am a bootstrapper, I would call it a life style. As an analyst — I bootstrap. As a statistician — I bootstrap (though grudgingly). My parents were bootstrappers and much of my life as well. It is what I do. So it was only natural, as I thought of investing in the next chapter of my life, that I bootstrap. For the record, I don’t actually own a pair of boots.

Plotting, Planning, and Plodding

For the next nine months, I dedicated every spare hour and a small handful of dollars (lunches and coffees) to developing the business plan. It was a very iterative model, it is what I do. I collected feedback, it is… you get it. And I pulled together a solid crew. Fellow bootstrappers, of course.

In May of 2015, I unveiled the endeavor as bootstrappers do. It was a small article that focused on commitment. Looking back, the emphasis on money may have been misleading. In actuality, we had raised a solid commitment but one that would hardly register against the VC backdrop. Honestly, it would be more of a rounding error.

Corsair’s Ventures — Investment On A Bootstrap

That May we launched this first venture under a brand that hit the mark. Bootstrap, as noted, is now more synonymous with CSS and web development these days. However, long before boots even had straps, intrepid crews of would-be bootstrappers were taking to the seas on ventures of their own. Their lessons would be part of our guiding principles, as well. Corsair’s Ventures was born (though our website has yet to be a priority).

Corsair’s launched a series of new bootstrapped start-ups. We invested in technology, education, content, and business services. It was a gamble, like the pirates of old, each prize crew spread our resources further. Many of our advisers thought we were crazy. We were warned that we could not sustain. We were warned that we would sacrifice the depth needed to succeed. We were gambling that this prize fleet could stay together and stay afloat.

Two Major Milestones in 24 Hours!

Here we are two years later. Two years is a long time to keep a team together. It is a long time to stay focused. But the progress has been constant, the revenue stream continues to build, and the client base continues to grow, and our mounting portfolio of platforms and products is just starting to move the flywheel of positive feedback. The fleet is still afloat and the crew continues to grow. We survived and then some…

When you enter a niche for unmet demand, especially in the area of professional development and education, content is difficult to come by. I had been warned early on but only appreciated the true scarcity once I could feel it first hand. We launched Corsair’s Publishing last November to fill that gap. Content development had always been on the road map, but never so early.

Last night, I wrote my 200th article as an executive contributor for our publishing company. I was our first contributor but we quickly attracted a crew of creative and inspiring writers and designers. Corsair’s Publishing now sports nine online magazines across all the popular channels (Medium, LinkedIN, Quora, Flipboard, Tumblr, Google+ and more). How is that for depth? Our subscriber growth has gone exponential — nine months from now we expect to be one of the largest content providers in our space.

To our crew — Congratulations! To our supporters — Thanks for your continued support! To those who may be discovering us for the first time — Welcome aboard!

There is plenty more to be written, so follow our journey! Explore what Corsair’s has to offer. Follow — Share — and Recommend ❤! We look forward to sharing our continued success.

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Decision-First AI
Corsair's Business

FKA Corsair's Publishing - Articles that engage, educate, and entertain through analogies, analytics, and … occasionally, pirates!