Jon Nass

Jon is a co-founder of Outdone, a company built to take the stress out of gift shopping. He oversaw the build and launch of Outdone’s AI-powered gift recommender — a first-of-its-kind on the web! Outside of professional endeavors, he is deeply passionate about snowboarding, photography, and climbing.

Where did the idea for Outdone come from?

During the holiday season of 2019, my co-founder and I found ourselves struggling to finish our gift shopping. To make matters worse, there seemed to be no solutions on the web built to solve this problem. Sure, there were tons of gift guides, but they all seemed quickly thrown together and difficult to navigate. We thought there must be a way to create a tech-driven solution to this problem that surely everyone could relate to! So, we built, Outdone, the web’s first AI-powered gift recommender.

What does your typical day look like and how do you make it productive?

From 9-5, I’m working at a rapidly growing martech firm where I’ve overseen business development and strategy for 3 years. My most productive hours to work on Outdone are typically from 8pm to midnight. I get home from work, exercise, eat and then have the rest of the night to work unbothered.

How do you bring ideas to life?

Slowly chip away. All great products start as an idea in someone’s head. The only way to see them come to fruition is through deliberately working towards the finish line. Day to day it will be hard to notice progress, but you’ll soon find yourself eons from where you started!

What’s one trend that excites you?

The general trend towards entrepreneurship and creation that has been spurred by the increasing focus on work/life balance is something I find very inspiring. You’re seeing more and more people working to build ideas they’ve had stored away in their brain, but never had the time to work on prior to these past few years. It’s one silver lining to this period that has been so tough on so many. I think we’ll see some really great products, art, books, and more come out of this.

What is one habit of yours that makes you more productive as an entrepreneur?

My ability to deep work (check out Cal Newport’s book!) is one that has helped me immensely — and I have tons of room for improvement on that front. For the uninitiated, deep work is the practice of focusing super intently on the task at hand for relatively short bursts of time. As someone who used to be easily distracted, this mindset and strategy has been a game changer.

What advice would you give your younger self?

Don’t be afraid to try! I’d often discredit ideas of my own because they seemed too daunting, too immense. But through working on Outdone, I’ve learned that putting in just a bit of work every day can lead to some amazing accomplishments.

Tell us something that’s true that almost nobody agrees with you on.

The filling of Double Stuf Oreos does not taste as good as the filling on classic Oreos. I swear they put less effort into the Double Stufs.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Expand your horizons. Challenge yourself to read about topics you’re unfamiliar with, talk to folks from different backgrounds, and never stop learning.

What is one strategy that has helped you grow your business?

Sharing early versions with anyone and everyone. You never know who will provide some awesome feedback that might seem super obvious in retrospect.

What is one failure you had as an entrepreneur, and how did you overcome it?

We were working with one freelancer who ended up going silent on us after a month or two of working together. This was a huge setback because it basically meant we had to start from scratch to build Outdone. We were able to overcome this by being super thorough in vetting our next hire.

What is one business idea that you’re willing to give away to our readers?

I worked on a business plan in college for sharable mopeds in major cities. This plan has been rendered a bit obsolete by the proliferation of Bird Scooters and CitiBikes, but I still think it might have some legs!

What is the best $100 you recently spent? What and why?

I bought a pair of North Face Thermoball slippers — basically a puffy jacket for your feet — and they are incredible. The North Face is actually a marketing partner of ours, but that’s not even why I’m plugging them here!

What is one piece of software or a web service that helps you be productive?

Notion is immensely helpful. It acts as the planner, task tracker, and (really) the brain of our business. It allows us to store and organize all the knowledge behind Outdone in one clean, easy-to-navigate environment.

What is the one book that you recommend our community should read and why?

The Alignment Problem: Machine Learning and Human Values by Brian Christian is incredible. It fires warning shots about how the future will look if we are not super deliberate in building machine learning models to avoid unintended consequences. And unlike many books on the subject, The Alignment Problem dives deep on the overlap between the fields of AI and human psychology, which is fascinating.

What is your favorite quote?

“If you don’t know where you’re going, any road’ll take you there.”

Key Learnings:

• Don’t be afraid to fail!
• If a task seems too large, just start chipping away at it.
• Don’t let perfect be the enemy of good — especially when it comes to launching a product.