Jason 🧠 Shen

Jason 🧠 Shen Jason 🧠 Shen is an influencer

The Outlier Coach · Helping venture-backed founders build conviction and win *their* game. Author of 'The Path to Pivot' & 'Weirdly Brilliant' · Retired NCAA 🏆 gymnast

Brooklyn, New York, United States
10K followers 500+ connections

About

There's a moment in every great company's journey where the founder makes a huge bet on the future. A decision that was terrifying at the time - but in retrospect, seems obvious. Even brilliant.

What separates the outliers who make that call from those who don't isn't raw IQ or blind courage. It's conviction. Not the kind you're born with - the kind you earn. Built on evidence, on small wins, on actually doing the thing.

Hi, I'm Jason - the Outlier Coach. I run an executive coaching practice for weirdly brilliant founders, leaders, and operators.

We work with clients to build that earned conviction. We dig into your unique advantages - the strange obsessions, the unconventional background, the hidden strengths you've always dismissed - and craft a narrative that helps the world see what you see.

The things that make us weird are often what power our greatest accomplishments: the outcomes only we could have made happen. And when you truly understand that, you stop hedging. You go out build the things that make our world bigger.

Follow me for insights on creative risktaking, resilience in uncertainty, and successful business partnership.

Or set up a discovery call at: https://www.calendly.com/jason-shen/discovery

Articles by Jason 🧠

Activity

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Experience

  • Refactor Labs

    Refactor Labs

    13 years

    • Refactor Labs Graphic

      Executive Coach

      Refactor Labs

      - Present 5 years 1 month

      Founder Coach: Work with early-stage startup founders (primarily venture backed) to navigate growth challenges, maintain momentum post-accelerator, and scale themselves as leaders.

      Startup Veteran: Leverage experience founding 3 startups and working as a PM at Etsy and Facebook to provide relevant, tactical guidance that bridges the gap between therapy and business advice.

      Cofounder Conflict Resolution: Help founding teams work through tension, rebuild trust, and align on company…

      Founder Coach: Work with early-stage startup founders (primarily venture backed) to navigate growth challenges, maintain momentum post-accelerator, and scale themselves as leaders.

      Startup Veteran: Leverage experience founding 3 startups and working as a PM at Etsy and Facebook to provide relevant, tactical guidance that bridges the gap between therapy and business advice.

      Cofounder Conflict Resolution: Help founding teams work through tension, rebuild trust, and align on company vision during pivots, growth phases, and strategic shifts.

      Strategic Decision Making: Serve as a sounding board for high-stakes decisions, helping founders gain clarity on product direction, fundraising strategy, and team building.

      Leadership Development: Support founders in developing their management skills, particularly during the transition from builder to leader as their companies scale.

      Burnout Prevention: Create sustainable work patterns that help founders maintain energy and conviction through the inevitable ups and downs of the startup journey.

      Team Dynamics: Facilitate better communication between cofounders and early employees, establishing healthy patterns that scale as the organization grows.

      Execution Focus: Keep founders accountable to their most important metrics and goals while helping them navigate distractions and shiny object syndrome.

      Founder Psychology: Create space for the emotional challenges of entrepreneurship while maintaining a practical focus on business outcomes and personal growth.

      Peer Connection: Leverage YC network and founder community to help clients learn from others who've faced similar challenges.

    • Refactor Labs Graphic

      Writer and Speaker

      Refactor Labs

      - Present 13 years

      Write about business, technology, and culture for publications with numerous bylines in TechCrunch, Fast Company, and Vox. My posts on Medium have a combined 800k+ views.

      Speak and teach at conferences and events on topics like gaming & esports, product management, entrepreneurship, talent development, and leadership. Since 2012, I've spoken on four separate continents (North Am, Europe, Asia, Australia) at places like Google, Pinterest, General Assembly, and Empower. My TED talk on the…

      Write about business, technology, and culture for publications with numerous bylines in TechCrunch, Fast Company, and Vox. My posts on Medium have a combined 800k+ views.

      Speak and teach at conferences and events on topics like gaming & esports, product management, entrepreneurship, talent development, and leadership. Since 2012, I've spoken on four separate continents (North Am, Europe, Asia, Australia) at places like Google, Pinterest, General Assembly, and Empower. My TED talk on the future of hiring has 4M views.

      Support ambitious startup founders as an executive coach.

  • Lunar Accel Graphic

    Founding Board Member

    Lunar Accel

    - Present 2 years 3 months

    New York, United States

    AAPI professionals in corporate leadership? The numbers are bleak.

    We're the least likely group to be promoted to management.

    That's not just unfair. That's a massive waste of talent.

    Enter Lunar Accel.

    They're not waiting for permission to fix this. They're building the solution themselves.

    - Mentorship for early career Asian American professionals
    - Inspiring the next generation of AAPI leaders
    - Leadership development that actually works
    - Started…

    AAPI professionals in corporate leadership? The numbers are bleak.

    We're the least likely group to be promoted to management.

    That's not just unfair. That's a massive waste of talent.

    Enter Lunar Accel.

    They're not waiting for permission to fix this. They're building the solution themselves.

    - Mentorship for early career Asian American professionals
    - Inspiring the next generation of AAPI leaders
    - Leadership development that actually works
    - Started in NYC, expanding to major cities

    Young team. Scrappy as hell. Punching way above their weight class.

    And I get to be one of the gray hairs in the room.

    Offering wisdom. (Questionable at times, but hey - that's part of the deal.)

    Cheering them on. Watching them build something that should have existed decades ago.

    This is how change happens.

    Are you an Asian American 2-6 years out of school? Apply for the next cohort.

    Have 7+ years of experience? Sign up to mentor a fellow.

    20+ years in and ready to really give back? Come speak at a cohort or make a donation.

    It's time to crack the bamboo ceiling.

  • Scout Graphic

    Angel Investor

    Scout

    - Present 3 years 8 months

    Finding great engineers for your startup is hard enough.

    Finding ones who are smart, emotionally intelligent, AND can mentor your junior team?

    That's like finding a unicorn riding another unicorn.

    Here's what most companies do:

    - Post on job boards. Wait. Hope.
    - Pay recruiters 15-20% of salary
    - Interview dozens of candidates
    - Still end up with someone who does nothing more than ship average code.
    - Rinse and repeat in 6 months

    I would know, I…

    Finding great engineers for your startup is hard enough.

    Finding ones who are smart, emotionally intelligent, AND can mentor your junior team?

    That's like finding a unicorn riding another unicorn.

    Here's what most companies do:

    - Post on job boards. Wait. Hope.
    - Pay recruiters 15-20% of salary
    - Interview dozens of candidates
    - Still end up with someone who does nothing more than ship average code.
    - Rinse and repeat in 6 months

    I would know, I founded a company to address this gap nearly a decade ago.

    Scout is continuing that vision, in a smarter way.

    That's why I invested =)

    Kirk and Randy have built a private network of remarkable software engineers.

    A community built on mentoring early-career talent.

    Drawn from some of the most successful tech companies in the world, big and small.

    Not just coders. Scrappy, thoughtful technical leaders.

    The best part for you? No double-digit recruiter fees eating your budget.

    Scout's model means you get top-tier talent without the traditional markup.

    Need engineers who can actually lead?

    Want to build a team that grows together?

    Ready to stop gambling on hires?

    Check out Scout and see the difference a curated network makes.

  • FSH Technologies Graphic

    Angel Investor

    FSH Technologies

    - Present 4 years 8 months

    Delightful government software? Sounds like an oxymoron.

    Imagine how much better digital government services could be if it was built by people who actually cared about technology and user experience.

    That's what the team at FSH is doing.

    Building affordable, genuinely delightful workflow tools for schools, courts, municipalities, and more.

    I wrote a tiny check to support the team years ago.

    But honestly? That's not the contribution I'm most proud…

    Delightful government software? Sounds like an oxymoron.

    Imagine how much better digital government services could be if it was built by people who actually cared about technology and user experience.

    That's what the team at FSH is doing.

    Building affordable, genuinely delightful workflow tools for schools, courts, municipalities, and more.

    I wrote a tiny check to support the team years ago.

    But honestly? That's not the contribution I'm most proud of.

    Both cofounders were interns and early hires at my last startup.

    If I had any real impact, it probably was in those early days - giving them room to grow, and showing them what it means to build something ambitious and new.

    I've seen firsthand how hard it is to bring innovation to government.

    Over a decade ago, I spent time doing exactly that through a presidential fellowship.

    What Lilly and Johnson are building at FSH is precisely the efficient and high impact innovation that government needs now.

  • Meta

    Meta

    3 years

    • Meta Graphic

      Product Manager, Facebook

      Meta

      - 1 year 2 months

      PM on Facebook Groups

      Led product for public groups which connect 400M+ people everyday to the interests, people, and communities they care most about, without barriers. Incubated a new product experience in FB Groups to millions of people.

    • Meta Graphic

      Product Manager

      Meta

      - 3 years

      Joined Facebook via acquisition of Midgame. Lead product across multiple teams on knowledge and productivity tools that serve both internal and external users including:

      🔒 Secure content repository / private wiki used by tens of thousands of Facebook content moderations, support agents, and sales teams. Expanded on the intial product to serve additional use cases (FTC audit, financial transaction processing) through integrations, workflows, and better UX.

      📚 0-to-1 product…

      Joined Facebook via acquisition of Midgame. Lead product across multiple teams on knowledge and productivity tools that serve both internal and external users including:

      🔒 Secure content repository / private wiki used by tens of thousands of Facebook content moderations, support agents, and sales teams. Expanded on the intial product to serve additional use cases (FTC audit, financial transaction processing) through integrations, workflows, and better UX.

      📚 0-to-1 product designed to help employees save, organized, and discover knowledge artifacts (documents, articles, presentations) easily across many different surfaces. Drove conception, strategy, and execution of project

      ✍️ Rich content editor that supports custom components and real-time collaboration. Adopted by numerous internal tools as well as several external ones like Bulletin.com and Workplace. Aligned leadership on shift in strategy from a product to a platform team and a major rewrite of the core architecture to enable real-time collaboration and mobile editing.

  • 13 Fund Graphic

    Angel Philanthropist

    13 Fund

    - 2 years 9 months

    New York City + San Francisco

    April 2020. COVID lockdowns everywhere.

    My best friend Bilal Mahmood and I had just exited our tech startups.

    People were struggling. Communities were struggling. Businesses were struggling.

    We felt like we had to do something.

    Here's the thing though...

    We'd both started non-profits before. We'd donated to plenty of causes.

    But this time? We wanted to do something different.

    We still believed in entrepreneurs. We believed in taking bold, risky…

    April 2020. COVID lockdowns everywhere.

    My best friend Bilal Mahmood and I had just exited our tech startups.

    People were struggling. Communities were struggling. Businesses were struggling.

    We felt like we had to do something.

    Here's the thing though...

    We'd both started non-profits before. We'd donated to plenty of causes.

    But this time? We wanted to do something different.

    We still believed in entrepreneurs. We believed in taking bold, risky bets that could have outsized returns.

    Something you rarely see in most giving campaigns.

    So we created something we called "angel philanthropy."

    The concept was simple:

    - Identify important challenges in our cities (New York and San Francisco)
    - Dig deep. Interview experts in the field
    - Select a scrappy organization with promising results
    - Scale them up with a significant donation

    We put in our own money first.

    Then rallied our communities to chip in.

    The result?

    Nearly $250,000 raised.

    - Small businesses in San Francisco
    - Fighting anti-Asian hate in New York City
    - Digital access for children of Chinatown

    While this project is on pause for now, we've each continued our social impact work.

    Bilal is now an elected official in San Francisco.

    I'm the founding board member of Lunar Accel, an AAPI leadership development nonprofit.

    I'm grateful to have friends who are so invested in making impact and doing good in the world.

    This was a lot of fun.

  • Presidential Innovation Fellows Foundation Graphic

    Board Member

    Presidential Innovation Fellows Foundation

    - 4 years 4 months

    The Presidential Innovation Fellows (PIF) program was established by the White House in 2012 to attract top innovators into government, capable of tackling issues at the convergence of technology, policy, and process.

    The PIF Foundation is a 501(c)3 organization established to support and advance the PIF program, drive innovation in the US government, and connect our 100+ alumni. Board members are elected by members to 2-year terms.

  • The Asian American Man Study Graphic

    Founder

    The Asian American Man Study

    - 7 years

    The Asian American Man Study a national survey of the experiences and beliefs of American men of East, Southeast, and South Asian descent. Our findings have appeared in The Atlantic, NBC Asian America, Vox, and Quartz, and has reached over 100,000 people on Medium. Over 1000 Asian men have been surveyed since our founding in 2015.

    Jason has shared his research and personal experience as a first-generation Asian American at Amazon, Pinterest, Proctor & Gamble, and Nielsen.

  • Midgame Graphic

    Cofounder and CEO

    Midgame

    - 1 year 9 months

    Greater New York City Area

    Midgame is an intelligent voice assistant for gamers and esports teams. We worked with dozens of leading collegiate and professional gaming teams and enhanced the gaming experience for players.

    Investors include Betaworks, Amazon’s Alexa Fund, Techstars, and the former head of Microsoft Cortana. Acquired by Facebook in 2020

  • Headlight Graphic

    Co-Founder & CEO

    Headlight

    - 1 year 4 months

    Greater New York City Area

    Headlight is a performance hiring platform. We develop software, assessments, and tournaments to help employers find, screen, and recruit talent. Headlight was acquired by Woven, a developer hiring platform.

  • TED Conferences Graphic

    Resident

    TED Conferences

    - 6 months

    Greater New York City Area

    Re-examining how we identify and cultivate human potential with The Talent Playbook (http://talentplaybook.co)

    The TED Residency program is an incubator for breakthrough ideas. Residents are chosen via a semiannual competitive application and spend fourteen weeks at TED headquarters in New York City, working on their ideas. Although some may produce an artwork, a manuscript, or an amazing theorem, each Resident will also develop a TED talk and deliver it on a TED stage.

  • Etsy Graphic

    Product Manager

    Etsy

    - 2 years

    Brooklyn, NY

    Build products to support & grow the 1.5M active sellers on Etsy's global marketplace. Projects included Shop Updates (marketing tool to connect customers with the human side of sellers), Sell on Etsy mobile app on Android, iOS, and Inventory Management (massive overhaul of seller tooling to support professional seller needs around variations and structured data).

  • Percolate Inc. Graphic

    Marketing Product Manager

    Percolate Inc.

    - 1 year 6 months

    Greater New York City Area

    Percolate is a technology company building the system of record for marketing. Founded in 2011, we serve scores of Fortune 500 clients around the world and are backed by Sequoia and First Round Capital.

    I build compelling technology and lead-gen products to drive awareness and adoption of our world-class marketing platform among our enterprise and midmarket clients.

  • White House Presidential Innovation Fellows Graphic

    Presidential Innovation Fellow (Smithsonian Institution)

    White House Presidential Innovation Fellows

    - 7 months

    Washington D.C. Metro Area

    The Presidential Innovation Fellows (PIF) program was created by the White House under the Office of Science and Technology Policy (OSTP) and pairs top innovators from the private sector, non-profits, and academia with top innovators in government to collaborate during focused 6-13 month “tours of duty” to develop solutions that can save lives, save taxpayer money, and fuel job creation.

    – Selected by the White House out of to serve high-impact “tour of duty” at federal agencies
    –…

    The Presidential Innovation Fellows (PIF) program was created by the White House under the Office of Science and Technology Policy (OSTP) and pairs top innovators from the private sector, non-profits, and academia with top innovators in government to collaborate during focused 6-13 month “tours of duty” to develop solutions that can save lives, save taxpayer money, and fuel job creation.

    – Selected by the White House out of to serve high-impact “tour of duty” at federal agencies
    – Led product management, usability research, and community engagement of crowd-sourced transcription site
    – As of 2019, more than 13,000 users have transcribed 450,000 pages of transcription
    – Proposed, designed and launched feature that doubled transcription activity per visit
    – Led cross-museum working group meetings, managed external marketing and communications
    – The Transcription Center has been featured on the Wall Street Journal (print), PandoDaily, and FOX 5 News

  • Ridejoy Graphic

    Co-Founder

    Ridejoy

    - 2 years 1 month

    San Francisco

    Ridejoy was a community marketplace for long-haul rideshare.

    We helped over 45,000 people share city-to-city rides across the US and Canada and to great events like Coachella, Maker Faire, and Burning Man. Deeply involved in product, user acquisition and partnerships.

    Ridejoy was cofounded by myself, Kalvin Wang and Randy Pang, funded by Y Combinator in Summer 2011 and raised $1.3M in seed funding from Freestyle Capital, SV Angel, Founder Collective and some other great…

    Ridejoy was a community marketplace for long-haul rideshare.

    We helped over 45,000 people share city-to-city rides across the US and Canada and to great events like Coachella, Maker Faire, and Burning Man. Deeply involved in product, user acquisition and partnerships.

    Ridejoy was cofounded by myself, Kalvin Wang and Randy Pang, funded by Y Combinator in Summer 2011 and raised $1.3M in seed funding from Freestyle Capital, SV Angel, Founder Collective and some other great investors.

    We were written up in Vanity Fair, TechCrunch, and The New York Times. Apple selected Ridejoy as a featured iPhone app multiple times in the App Store.

  • isocket Graphic

    Customer Acquisition Lead

    isocket

    - 11 months

    isocket is a technology platform designed to simplify guaranteed media sales, and one of the first companies to facilitate the programmatic buying of direct, guaranteed display ad inventory. It was acquired by Rubicon Project in 2014.

    I headed our customer acquisition efforts and grew our publisher base by 16.6x and total revenues by 10.5x through in person / phone sales, email marketing campaigns, PPC advertising on Google & Facebook, custom landing pages, display ads & video…

    isocket is a technology platform designed to simplify guaranteed media sales, and one of the first companies to facilitate the programmatic buying of direct, guaranteed display ad inventory. It was acquired by Rubicon Project in 2014.

    I headed our customer acquisition efforts and grew our publisher base by 16.6x and total revenues by 10.5x through in person / phone sales, email marketing campaigns, PPC advertising on Google & Facebook, custom landing pages, display ads & video marketing.

    I also was involved in customer support, product development, and social media (blogging & Twitter).

  • Gumball Capital Graphic

    Co-Founder & Board Member

    Gumball Capital

    - 4 years

    Started a nonprofit with some friends at Stanford. Our mission was to engage students with microfinance and entrepreneurship to help fight global poverty. Ran entrepreneurial competitions at dozens of high school and college campuses, helped fund over 800 microfinance loans to members of the working poor in developing nations. Caught the startup bug and met some of my best friends and future collaborators.

  • The Stanford Daily Graphic

    Chief Operating Officer

    The Stanford Daily

    - 1 year

    I worked full time to manage the staff, operations & financial performance ($740k revenue in ‘09) for Stanford's independently incorporated newspaper.

    We battled an economic downturn and brutal industry-wide revenue declines by overhauling financial operations, restructuring the sales team, launching print and email marketing campaigns and building sales partnerships. In 12 months I was able to stabilize the serious revenue decline while avoiding major cuts to the core business.

    I…

    I worked full time to manage the staff, operations & financial performance ($740k revenue in ‘09) for Stanford's independently incorporated newspaper.

    We battled an economic downturn and brutal industry-wide revenue declines by overhauling financial operations, restructuring the sales team, launching print and email marketing campaigns and building sales partnerships. In 12 months I was able to stabilize the serious revenue decline while avoiding major cuts to the core business.

    I developed & launched our Daily Digest email, which grew from 0 to 260+ subscribers and our Twitter feed (0 → 1140+ followers) in only a few months.

    As Treasurer for the Board of Directors, I prepared and presented financial statements and guided the board on key strategic & financial decisions at monthly meetings.

    I also began and continue to direct The Stanford Daily's efforts to digitize and make available online the entire span of Daily papers (over 35,000 issues over 118 years) - a six-figure project coordinating between multiple external vendors and various departments within Stanford.

  • Stanford University Graphic

    Team Captain (Men's Gymnastics)

    Stanford University

    - 5 years

    Captain of the 2009 Division 1 NCAA championship-winning team - our first title in 14 years. Was a recruited scholarship athlete and trained over 20 hrs/wk, year-round.

    Achieved 9th place ranking in the all-around in 2006. Suffered a total knee dislocation that required surgeries in 2007. Made a huge recovery and team reached #1 ranking in 2008 and closed the deal in 2009.

    I've been doing gymnastics since I was 6 years old and competition nationally starting at age 11. As a young…

    Captain of the 2009 Division 1 NCAA championship-winning team - our first title in 14 years. Was a recruited scholarship athlete and trained over 20 hrs/wk, year-round.

    Achieved 9th place ranking in the all-around in 2006. Suffered a total knee dislocation that required surgeries in 2007. Made a huge recovery and team reached #1 ranking in 2008 and closed the deal in 2009.

    I've been doing gymnastics since I was 6 years old and competition nationally starting at age 11. As a young gymnast, I earned a spot on the US Jr National team in 2002 and placed 4th in the 2004 Junior Nationals. I have competed in several USA Championships against World Championship and Olympic team members.

Education

  • Stanford University Graphic

    Stanford University

    Bachelors & Masters of Science Biology

    Ethics in Society Honors Program, Academic All-America First Team. NCAA national champions (mens gymnastics)

  • Y Combinator Graphic

    Y Combinator

    Ridejoy (Summer 2011)

Licenses & Certifications

Volunteer Experience

  • Minds Matter Graphic

    Mentor

    Minds Matter

    - 2 years

    Education

    Minds Matter is a not-for-profit organization with chapters in 11 cities, that transforms the lives of accomplished high school students from low-income families by through mentorship and academic enrichment in preparation for college.

    I'm part of a team of ten mentors working with five mentees who meet every Saturday for about two hours. My mentee is a brilliant, sarcastic, and super-introverted young woman from Brooklyn. She's awesome.

Skills

Publications

  • How to Get What You Want

    Amazon #2 Bestseller in the Applied Psychology category.

    When we don’t have a clear understanding of what we truly want, and a game plan for how to get it, we turn into a pawn in someone else’s plans. It’s a battle: our agenda vs theirs. Weaving tactical advice, psychology research, and powerful stories into 36 focused chapters, this book gives us the tools we need to figure out, and get after the things we really want.

    See publication
  • Guide to YC

    Hyperink

    The complete and indispensable game plan for founders applying to Y Combinator. 92 pages on team, product, distribution, interview and everything else that matters for getting into the best startup incubator in the world - downloaded by thousands of entrepreneurs.

    See publication

Honors & Awards

  • World Record: Most Number of Aztec Push-Ups in One Minute

    Guinness World Records

    Defending world champion for most number of Aztec Push-Ups completed in one minute (50). Beat previous record set in 2012 by Brandon Collofello (31). Recognized by Guinness World Records.

    Full story: http://www.jasonshen.com/2015/ended-setting-guinness-world-record-aztec-push-ups/

Languages

  • Chinese

    -

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