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Starting & Sustaining
Letter sent on Jul 5, 2016

The Next Chapters

In March of 2013, I launched Starting and Sustaining to share my experiences bootstrapping Sifter, a simple issue tracking web application, and help others along the way. Little did I know at the time that five months later a surgery recovery gone wrong would derail my plans.

Two years and nine surgeries later, I decided it was time to move on from Sifter and focus my efforts elsewhere. These days, I’m working full-time at Wildbit, and, while not absolutely certain, it’s likely that in the near future I’ll be amputating my left leg below the knee.

I wrote Starting and Sustaining with an eye towards the future and the hope that the lessons and anecodotes would stand up well over time despite the rapid pace of technology change. For the most part, they’ve held up well, but there are certainly some overdue updates, and I’m starting work on a second edition to include those and go even further.

Through all of my medical issues and ups and downs that ultimately led to deciding to sell Sifter, I’ve learned countless new lessons. About resilience. About designing for profitability. About preparing a business to be sold. About working with buyers. And much much more. Even though I’m no longer running Sifter, I still have a lot I want to share with others.

I’m going to start here. I’ll be releasing all of the original chapters from the first edition here on Medium. The second edition will include updated versions of many of those chapters. While I haven’t completely thought through the logistics of the second edition yet, I do plan on taking care of everyone who supported the first edition. One thing I know for sure, this time it will be Kindle friendly.

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