Paul Mestemaker



Paul Mestemaker II

Founder / CEO / CTO / Advisor

About Me

Paul Mestemaker is founder and CEO of CleverPoint LLC as well as the cofounder and Chief Technology Officer at Circadian Risk. Circadian Risk started as a CleverPoint incubation project in 2016. He oversees the engineering, product, and design teams.

Paul's based in Los Angeles. He loves to dabble in machine learning and game theory. In his former life, he was a co-founder of Mythly Studios, Head of Product at and a founding member of the System Center Advisor team at Microsoft. He co-authored a book on SQL Server performance tuning. He has been rated as a top speaker at conferences (TechEd, PASS, Connections, et al). He is also a guest lecturer at colleges and universities across the U.S. He was the co-host of a weekly tech news show with over 6 million views. Paul's proudest accomplishments are unlocking the "World Champ" achievement on Wordament and becoming a Grandmaster in Settlers of Catan. ;)


Circadian Risk Inc - Cofounder/CTO

Building software to assess risk with physical infrastructure.

CleverPoint LLC - Founder/CEO

Helping startups, established businesses, and nonprofits apply clever uses of technology to achieve their goals.

Previous Ventures

Close Inc - Cofounder/Head of Product

Invite-only network to help executives get deals done. Close Inc became after my time there. After several more years, it was acquired.

Mythly Studios Inc - Cofounder/CEO

Building immersive advertisements and editorials for the iPad with early explorations in AR. This business has since pivoted to a VR game studio making a game about immortal babies beating each other up with selfie sticks.

Microsoft - Senior Program (Product) Manager

Paul Mestemaker is one of the original founding members on the System Center Advisor team at Microsoft. In his ~7 years at Microsoft, he focused mainly on server manageability and supportability tools. He co-authored a book: Professional SQL Server 2005 Performance Tuning. He has been a top speaker at TechEd, MMS, PASS, Connections, and other Microsoft and industry conferences. He is also a guest lecturer at colleges and universities across the world (MIT, University of Michigan, Kellogg, UIUC, EAE Business School in Barcelona, et al). He was the co-host of Ping, a weekly tech news show on Microsoft's Channel 9.

Side Projects

Trading Bot

High-frequency trading bot to respond to events in near real-time to trade on public markets as well as cryptocurrency exchanges. Since its inception in 2015, it has performed over 30k trades.

Event Discovery

Algorithm to discover trending places and interesting events based on information available on the web. Current state is that it just spits out spreadsheets, but there are grander plans to productize one day.


Paul co-authored a book that is available on and used to be in Barnes & Noble stores nationwide.

Podcast Host

He was also the co-host of a weekly web show called Ping on Channel 9 that had a loyal following of about 30,000 viewers and over 6 million total views.

Early Background

Paul got his start in technology at an early age. He was one of the world's best Tradewars players. The key to his success was the custom scripts he wrote to play the game on his behalf. Shortly thereafter, his programming hobby turned into a business building custom software for Fortune 500 companies. His initial projects were to author simple Excel macros, then fix Access databases, then design new Access databases, and ultimately build web applications integrating SQL Server, Oracle, IIS, and Active Server Pages (ASP). Paul loves helping others and has a knack for teaching. He helped design and teach a C++ programming class. He accomplished all of this in high school before he was legally allowed to drive!


Standup Comedy

Paul Mestemaker got his start in standup comedy by incorporating humor in presentations at conferences and motivational speeches at colleges and universities. Paul first tried standup at Giggles Comedy Club in Seattle, WA. Since then, he's performed all over the country (Chicago, L.A., Las Vegas, Boston, Charlotte, et al.). He's opened for household names like Jeff Dye (from Last Comic Standing, Money from Strangers), the Roast Master General himself, Jeffrey Ross, and the late Greg Giraldo.

His comedy tells a story of how his life has changed since moving out to Seattle from the Midwest. He reflects on some of the mistakes he's made along the way, and some of the absurdities of modern dating. Most recently, Paul combined his standup with his motivational speaking style into a very fast-paced and hilarious PowerPoint presentation. Paul also makes a great host/MC for charity events as he has a clean sense of humor and can think on his feet and interact with diverse sets of crowds.

Comedy Resume

Venues Performed (Partial List)

The Comedy Store (Los Angeles, CA), The Excalibur (Las Vegas, NV), Giggles Comedy Club (Seattle, WA), Parlor Live Comedy Club (Bellevue, WA), Laughs Comedy Spot (Kirkland, WA), Mark Ridley's Comedy Castle (Royal Oak, MI), Comedy Underground (Seattle, WA), The Edge Comedy Club (Chicago, IL), Columbia Winery (Woodinville, WA), Comedy Zone (Charlotte, NC)

Comedians I have worked with (Partial List)

Alonzo Bodden, Auggie Smith, Bobcat Goldthwait, Brad Brake, Brad Upton, Bret Ernst, Dan Levy, Dov Davidoff, Duane Goad, Emo Philips, Gabriel Rutledge, Greg Giraldo, Harrold Gomez, Jake Johannsen, Jeff Dye, Jeffrey Ross, Jimmy Dore, Jimmy Shubert, Kirk Fox, Kivi Rogers, Kyle Erby, Larry Miller, Lisa Landry, Louie Anderson, Lukas Seely, Stephen Rannazzisi, Steve Byrne, TJ Miller, Tommy Savitt, Vince Valenzuela


If I could give you piece of advice... it would be: 'don't change'.

-Bobcat Goldthwait (Oct 2010)

Good stuff! You can go far with [your act].

-Kivi Rogers (Oct 2009)

I've never seen anything like that! You're hilarious!

-My future girlfriend