🪜Jason Yoong: Operating Partner at Level Up with Ethan Evans

Finding Professional Success Through Great Leaders, the Power of Community and Paying it forward

May 29, 2024

Hello, It’s Julia, Founder of The Switchboard, a newsletter exploring the ways we communicate and connect at work and beyond. Thank you for being part of our community. I’m grateful to you for reading, reacting and commenting. If you enjoy this edition, consider sharing it.

In This Edition

Follow great leaders and managers in your career
Transform career-growth through community-learning
Contribute to culture to positively impact your workplace

About Jason

Jason has run multiple $100M+ businesses across eCommerce, marketplaces, advertising, and media. He's led 40+ person organizations, owned department P&L, managed $250M+ marketing budgets for Fortune 100 entertainment (movies and broadcast TV) and consumer electronics clients, and served as a non-profit Advisory Board Member.

After leading and building at publicly traded companies Amazon, Dentsu Aegis, and Universal McCann (IPG), Jason joined the founding team of a venture-backed software startup and raised $8M seed.

Jason is now building Level Up: Your source for career growth solutions and community with Ethan Evans (retired Amazon Vice President) and serves as a mentor at First Round Capital and Techstars.

What inspired your career path?

It’s been a nonlinear path. But, this windy road has had one common theme — I’ve followed great leaders and managers. This has given me the chance to work across different industries, big companies, startups, and now a two-person team.

In a business partner, I value intelligence, high energy, and high integrity.

Ethan Evans

, retired Amazon Vice President and my co-partner on Level Up, hits all three. When you find a partner like that, you just run with it.

Let’s talk about Level Up. Can you tell us about what you’re building?

Level Up is your source for career growth solutions and community. Members engage with our newsletter, live podcasts and events, executive coaching, and a private community. As the operating partner, I co-own all business aspects with Ethan, this includes content, growth, community, marketing, partnerships, P&L, operations, product, strategy, events, design, and more.

Ethan is the rare big tech executive who tells you the candid unvarnished truth that you wish an executive would tell you about career growth. He also has a larger life mission to pay it forward.

We bring a diverse range of domain experts through fireside chats and community members get to engage with them live. The community and access to rare career advice are our core benefits because we believe in the power of a win/win network. We also offer live and on-demand online courses such as Cracking the C-suite, Stuck at Senior Manager - How to Break Through to Executive, Managing Up Successfully, and more.

Can you share highlights of what it’s like behind the scenes for your community?

One of our most popular community events is watching Ethan live executive coach a real client. You learn alongside the client and learn how Ethan coaches. The first client was a Director of Product and the current client is a Sales RVP in big tech. You get all this for $17/mo (compared to Ethan’s $1,500/hour, which is so oversubscribed we closed the waitlist).

We also do Ethan-only “Career Talks.” The first one was “How being unreasonable drove me to Amazon Vice President.” Ethan talked about the difference between unreasonable and irrationality as a leader. The key message is that you have to inspire and drive your team to move fast and deliver big results but you don't want to come across as that's the only thing that matters — you have to be an empathetic leader.

With fireside chats, members consistently reference two stories:

Ethan chatted with Harriette Cole, leadership coach and media trainer to Fortune 100 executives and Grammy-winning music artists such as Alicia Keys. Her biggest lesson was on the power of preparation. Alicia Keys was her best student because she prepared relentlessly. She has a three-part formula for Executive Presence: Preparation + Confidence + Full Focus = Executive Presence. Full focus is critical and most people miss this when they go into an executive meeting, they get so stressed, they don’t focus on the core meeting goal. You can watch Ethan and Harriette’s discussion here.
I chatted with Dave Kline, formerly of Bridgewater Associates, and there was a part about the power of managing up to the visionary CEO and Founder Ray Dalio. Ultimately, the lesson learned was that it was about deciphering ambiguous context. The best way to manage those Executives is with quick iterations and updates, reminding them “You asked for this. Here's where we are right now. This is what we're doing next.” Here’s a short clip from Dave.

When we focus on professional success, this can also be influenced by culture. What does culture mean to you and how has it shown up in your career?

Culture is a peculiar way of working. It's the way decisions are made, how teams decode problems, the daily language used, the way a company hires, fires, and rewards.

When I was at Amazon, it was known for its culture, which has been institutionalized through the Leadership Principles. My business partner, Ethan Evans who is a retired Amazon Vice President and worked there for over 15 years, helped write one of the Leadership Principles on “Ownership” — the words, “They never say ‘that’s not my job.’” are Ethan’s (read the story).

There's tension amongst the Leadership Principles, and that's purposeful. For example: you have Bias for Action which prioritizes speed yet you also have Insist on the Highest Standards. How do you balance the two if you're launching a new product or service? It's not easy but that conflict is intentional because it forces clarity of thinking.

Leadership Principles should be embedded in your operational processes. Drawing from my time at Amazon, we’re all taught when you propose a new product, you write a PR/FAQ first. It’s how the team imagines what they would say in a press release (PR) and all the questions (FAQs) that might be asked. The Principles are also critical for hiring. There is a “Bar Raiser” program where trained Bar Raisers serve as neutral third-party advisers during the interview process. They are not associated with the hiring manager or their team and have full veto power.

How did you contribute to culture when you were at Amazon?

I had the privilege of serving as an Amazon Fishbowl (fireside chat) moderator with authors. I attended a few Fishbowls in person and online. They were great — they helped me think differently and got me outside of my day-to-day work. There was a forum for submitting recommendations and I suggested Alexis Ohanian, the co-founder of Reddit who had written Without Their Permission, because we had partnered on a non-profit event before I joined Amazon. Fast forward, the Fishbowl lead asked if I could get Alexis to speak, I reached out, and I was asked to moderate.

The response (I am assuming) was positive because I was asked I invited to moderate additional Amazon Fishbowls, including two with Ryan Holiday.

What is your favorite life and work hack?

I like to combine three. First, I try to stay productive by embracing Work Like A Lion, Not A Cow. Instead of working at the same pace from 9:00am to 5:00pm, you save energy and go full force with bursts, followed by rest. I’ve found that if I do 90 minutes of deep work straight, that’s a good limit for me. Then I take a break — this could be going for a nature walk, reading, or an activity.

Next, I eat the frog by noon! I find that one huge task that can be completed and feel great about it.

Third, I think about portraying the character you want at that time of day. This helps me be fully present. Before my 2-year-old daughter wakes up, I’m the workout machine. When I'm with my child, I want to be the best dad in the world. When I'm working, I work like a lion. When I'm with my wife, I try to be the best partner.

Thank you Jason for a fun conversation. This career profile is based on a live interview. I’m grateful to you for reading, reacting and commenting. If you enjoyed what you learned, consider sharing it with a colleague or friend. Signing off for this edition. — Julia

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