The Pre-Mortem Letter

For the last 15 years — as part of my involvement in TeamStrength — I have written a Pre-Mortem letter. What is a Pre-Mortem letter? It is a letter written to yourself, at the start of the year, but from the perspective of the end of the year. I find it to be a valuable planning tool for big-strategy and important-details.

Below is the letter I wrote at the start of 2019.

I’ve redacted some personal and professional details but left in as much as I possibly could. When reviewed later, each letter becomes a list of goals achieved and opportunity missed. Over the years the letters (ideally) become a more accurate plan and prediction for the year.

12/31/2019

Jonathan –

Are you sure you’re ready to look back on all this? No time like the present. Here we go…

Sighthound

Well, you wanted to be a CEO and have a “real job” again… you just didn’t realize it would be at Sighthound. With ███████ ██████ ██████, you had to jump in and remove as much uncertainty as possible for the employees. That happened amazingly quick — you realized the one upside to ████████ avoiding ██████ ███████ at work was how much easier it was to move forward without ███.

As soon as the team was doing great, you refocused on the fundraising you had planned to start in early February. By the April you had raised $500k, and by May you had raised $1m.

The subject that led to ████████ █████ ███████ made you realize you urgently needed a full-time product manager. Fortunately, Gordon Cloke — the best product manager you’d ever worked with, was “made available” less than fifteen minutes after this idea occurred to you. You and RJ agreed that Gordon was the perfect research-focused balance to the more intuitive style you and RJ use to make decisions and brought him on as an equal in the role of Chief Product Officer, heading up not just product management but also operations and technical support.

Gordon spent most of the year learning about the company, its products, and its customers, and analyzing what the best revenue growth opportunities and priorities were amongst the sighthound.io, investigator, sighthound video, and Sighthound camera hardware opportunities were. Together, you, Gordon, and RJ decided which opportunities pick and which to drop.

You also realized that it was time to build an intentional (as opposed to accidental) culture at Sighthound and brought in Ryan Campbell as the part-time Chief Culture Officer. Once he returned to Florida in late March, Ryan dove in to recreate the strong interviewing, hiring, on-boarding, and training systems you had at Voxeo. Ryan worked very closely with the whole leadership team to define and implement this intentional culture.

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Denny worked with Ryan to bring back the excellent feedback you got at Voxeo by using the Net Promoter Score (NPS). Things have changed greatly with NPS since you last used it in 2013, including the availability of great services such as http://promoter.io . You knew your initial NPS would be low but were happy to get close to 35% as a place to start. It will take a year or two to get that score up to 65% or higher.

Coming into 2019, you had two companies you wanted to take a close look at acquiring: Code-named “Falcon” and “Hamlet”. You worked with RJ, who you promoted to President and CTO, to perform due-diligence on both, with Gordon to identify how their products and features would best fit into Sighthound, and with Ryan on how to best integrate the teams. Sighthound ended the year with significant revenue growth from $█████ to $█████, with most of that revenue coming from contracts that were signed before 2019.

Tiburon House

After a great deal of work and negotiations, you had the Tiburon office/house under contract for nearly $█████ by the end of March, and the sale closed by the end of May. You also sold most of the furniture in “Marin’s largest garage sale” and shipped the few items you and Nicole wanted to keep to NYC and Orlando. While you missed the views, you did not miss the boredom.

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Winter Park Coworking

Following years where the biggest financial hole in your pocket was the Winter Park office, by April the Winter Park was cash-flow break-even, and by June was making a small profit. Starting in April, you had a monthly “high profile” entrepreneur or investor — the kind of people the Central Florida startup community doesn’t typically hear from — speak at the Coworking office. Highlights included Scott Parazinski (5-time shuttle astronaut), Greg Baty (VC and 7-year NFL player), and Phil Dauber (one of your mentors and a prior CEO of Memorex).

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Glider Purchase

It has been 20 years since you first fell in love with flying sailplanes. The sport, which you have often described as “the only hobby that’s more fun than working”, did not get much of your time or attention over the last ten years. You want the kids to start flying when they are 15, and wanted to get back to flying yourself. So after 19 years of daydreaming about it, you ordered a Stemme S-12G, the sexiest and most bad-ass glider mankind has ever made. Now you’re waiting patiently for the 18 months required to build and ship the glider from Germany to end. You eagerly look forward to its arrival in the second half of 2020.

Thunder Ranch Couples Shooting Course

On April 2rd, you and Nicole flew to Reno, NV and then drove three hours to Lakeview, OR to attend the 4-day Thunder Ranch Couples shooting course with one of your favorite YouTubers, Wranglerstar, and his wife. It was the first time Nicole shot a rifle outside of an indoor range and you both learned more than you could imagine about tactical rifle shooting.

Summer in NYC

At the end of May, the kids finished school and you all left spend the summer in New York. You again attended the Governors Ball music festival, saw Queen with the whole family, and Nicole and Maddie saw Billie Elish, Maddie’s favorite artist this year. You and Nicole saw two more Broadway plays and the whole family visited a few new museums. You played PUBG and other games with Ethan

You travelled back to Orlando every other week to spend time in the Sighthound office. Ethan took swim lessons twice a week, and Maddie took volleyball lessons as often as she could. It was a great summer. In the end you again failed to convince the family to move there…yet.

Hawaii Vacation

In June you returned to the ██████ in Hawaii for another yearly vacation with Nicole, Ethan, Maddie, and your Sister-in-laws family. You swam, snorkeled, dove, hiked, sailed, and relaxed — and finally made the early-morning trip to see a sunrise from atop the Haleakala volcano. Everyone ended the trip happy, mentally rested, and physically tired.

Christmas Return to NYC

After Christmas, the family returned to NYC for 15 days of rest and recovery. Fifteen blissful days of having fun, eating great food, and just spending time with together with no agenda.

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In Conclusion

It was a very busy year indeed, but a busy year is exactly what you needed after being down in 2018. You enjoyed almost every moment of it, but look forward to, perhaps, relaxing just a bit more in 2020.

-Jonathan