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Jon Love

Most ques­tions have shades of gray, so the answer is usu­al­ly it depends’.

Jon Love

I've never been accused of brevity.

Jon Love is a Principal and the Director of Sales at GRAYBOX. He’s originally from the “hobby country” (Arlington), an hour north of Seattle, and relocated to Portland in 2014 for equal parts family and the GRAYBOX adventure. He’s also a serial entrepreneur. From car wash to candy company to a consulting agency, Jon is always looking to build a better mousetrap to share with the world. Jon has never been accused of brevity, and likely won't be in the near future.

Jon started his career in law, graduating from Gonzaga School of Law and (briefly) practicing in Washington state. While contracts and intellectual property are important, it turns out they weren’t engaging. People talk to their attorney when bad things (1) have happened, (2) are about to happen, or (3) might happen in the future. By contrast, business and technology consultants get to work with people when good things fit those measures. The choice was easy, and Jon gave up law for consulting in 2006.

The nuts and bolts: Jon was an ERP & CRM consultant for about 8 years before joining GRAYBOX. He’s worked with hundreds of companies across many industries, both on the business and technology fronts. If you need to jump seamlessly from high-level strategy to deep process, or from business and accounting to technology and data, you'll love talking with Jon.

As Dir. of Sales at GRAYBOX, Jon is generally the first point of contact for prospective clients and helps ensure a smooth flow from first contact to successful project through each of the Practices. As for approach, Jon is pragmatic. Every business is a little unique, and Jon really enjoys solving actual business problems that will make a material difference for the client. Business requirements are like legal puzzles — you solve them by breaking everything into their smallest components, then crafting an elegant solution on a well-laid foundation. The best solution isn't specific tools or tech, it’s the combination of answers that best addresses the question.

Outside GRAYBOX, Jon is married with two young kids and lives in NE Portland. He loves to golf, is a science nerd, and will strongly argue that an HBR subscription is more valuable than 90% of MBA programs. He’s an active member of the Portland Rotary club (and lifelong Rotary participant), and finds yard work and home improvement projects incredibly cathartic.

If you had $2000, how would you double it in 24 hours?

1. Options Trading!
I'd leverage half the money in a butterfly spread to hedge the risk, and put the other half in a combination of put and call options on volatile stocks.

2. Single Deck Blackjack!
I'd buy a plane ticket to Nevada, and either hit old town Vegas or the Cal-Neva in Reno for 24 hours of single deck blackjack. I'd play tight using a high-low card count strategy, and scratch $2000 out over the course of a full day.

3. Charitable Giving!
Lots of companies will offer matching gifts for charitable giving. So long as the doubled money can be with a charity, I’d hit the internet to find the best-matching programs, and use my $2000 as seed money to get at least $2000 of matching funds from a corporate entity.