Venture Stories: What Daniel Gross Thinks About Basically Everything

Key Takeaways

  • “You have to be very careful with what you measure”
    • For example – In CrossFit, many people get injured because of what’s measured (getting as many reps as possible can cause people to forget the importance of form)
  • “I think we’ll find out a decade from now that Twitter has fundamentally reshaped the human psyche”
    • After tweeting, people immediately look to see if they received any likes/retweets – this can’t be healthy behavior
  • “I think it’s criminal that we ask teenagers to wake up at 6:45”
    • “Adults want to wake up early, but children do not. I think school should start at 11 AM. That alone may change the world.”
  • If you run a startup, make sure you’re constantly talking to your users
  • The best career decisions are often made while people are on vacation because it’s the only time when people actually reflect on their job satisfaction


  • Hosted by Erik Torenberg (@eriktorenberg), co-founder and partner of Village Global (an early-stage venture capital firm).
  • Guest: Daniel Gross (@danielgross), founder of Pioneer, “an online tournament for productivity.”
    • Prior to starting Pioneer, he founded Cue, a machine learning company that was acquired by Apple

Daniel’s Background

  • Gross got into Y-Combinator as an 18-year-old
    • His company (Cue) got acquired by Apple and he eventually became a director there at the young age of 23
  • Soon after, he left Apple to become a partner at Y-Combinator
  • Gross says when you meet successful people in Silicon Valley, you realize there is “an enormous amount of happenstance and luck involved in their success”
    • Gross believes that for every great founder that makes it, “there are hundreds or even thousands more that don’t really ever make it and still do their great thing”

Daniel’s New Company – Pioneer

  • Gross believes Pioneer can “10x the amount of extraordinary people”
    • Pioneer gives people a little bit of money, but more importantly, it gives them the motivation to follow their dreams
    • Pioneer is built almost entirely on software and is similar to a game with a global leaderboard
      • People can work on any domain (SaaS, AI, Music), and the more progress they make towards their goals, the more points they earn
        • After 30 days, the best players receive $1,000, a round-trip ticket to Silicon Valley, and access to mentorship from some of the world’s most successful individuals.
        • “We are trying to scale the benefits of an Ivy league to the millions of lost Einsteins in the world”

The Concept of Life as a Video Game

  • “Games are fundamentally the way we explore the world”
    • Games encourage human cooperation and competition
    • A lot of games teach resource allocation problems – “You’re doing literally the same thing a McKinsey analyst does”
  • Gross modeled Pioneer after many lessons learned from gaming
    • A leaderboard and point scores are incredibly powerful because they motivate people to work harder
      • “It’s incredibly potent and incredibly powerful”
    • Other important game mechanics include instant feedback and injecting randomness into things
    • “Software should use all of these psychological techniques to motivate you to get what you want done”
  • “I would love to have game mechanics kind of everywhere”
    • However – “You have to be very careful with what you measure”
      • For example, in CrossFit, Gross says two things usually happen: Either people check out because it’s too intense or they get injured within a few months
        • People get injured because of what’s measured -getting as many reps as possible
        • To get as many reps as possible, people usually break form, which eventually leads to injury
        • “You have to be careful on what you measure and promote”
    • Gross has found himself running more since he downloaded Strava (an app that measures your running distance)
      • Gross read somewhere that the best way to motivate people to run is to put them on a network like Strava, with a group of people slightly slower than them
        • “You just made it an easy game to win” and that motivates people
        • However, if the game is too easy it becomes boring and monotonous. If it’s too hard, people will quit before even competing.

Gross’ Thoughts on Twitter

  • “I think we’ll find out a decade from now that Twitter has fundamentally reshaped the human psyche”
    • After tweeting, people immediately check to see if they got any likes/retweets – that can’t be healthy
      • This makes the brain feel good, further encouraging this type of behavior
  • Twitter is used by a lot of journalists who spread media across the world
    • Journalists aim to maximize likes/eyeballs (views = revenue) and that is changing the type of articles they write
    • “You have to be careful of what you reward because people will optimize it”
  • Why do people care if others unfollow them?
    • “What people think about you, especially the people you respect, is a very important signal as to whether you are doing the right thing or not. And I imagine it has a long-standing million-year tribal history.”
    • “You care who unfollows you because those people have basically decided to vote and say your ideas are bad or uninteresting”

Positive Sum and Zero-Sum Games

  • Pioneer has multiple winners because people are more likely to help others when more than one person can win
    • In the venture world, funds compete for a limited amount of deals so there isn’t much cooperation (zero-sum game)
    • But in hedge fund deals, people work together and even have company off-sites with other firms (positive sum game)
  • Gross likes to encourage people to play “infinite games”
    • What does he mean by this? – Playing for the long term and helping others, so that multiple people succeed instead of just one person winning in the short-term
  • Matchups between players are important
    • In Pioneer, players are constantly rating each other’s progress
      • Gross wants to group people in exciting matchups against players similar to your level
    • People become extremely competitive when working together to fight an AI (World of Warcraft)
      • “The other tribe is fictional” but people still work together to beat it

More on Pioneer

  • “Users are using the product as a gym for productivity”
    • Gross gets emails from people who didn’t win at Pioneer, but still thank him, saying the program helped keep them accountable to their goals
    • A lot of Pioneers who win, reapply to the program.
  • Gross is working on making Pioneer more of a long term game where winners can keep coming back and “leveling up” over time, just like in a video game.

Face to Face vs. Online Competition

  • This is already happening in the fitness world
    • Peloton has people competing online and SoulCycle has people competing in the physical world
    • Gross believes competing in the real world has many more advantages
      • You can physically see and hear other people, their progress, work ethic, etc.
      • People who go to a physical gym may have friends and competitors there who motivate them
      • Gross is working on taking those advantages from real-world competition and building them into Pioneer
        • One example is having personalized leaderboards

What can people learn from religion?

  • “Religion needs to be respected even if you don’t believe in it because it is still here after so many years”
    • Religion provides an interesting framework on how to enforce tribal bonds. It connects people who wouldn’t ordinarily connect with one another or don’t know one another.
      • “Jewish community and identity is very strong, despite it never being proven”
  • How can we create a new religion to encourage people to work together? – That’s the question Daniel is trying to answer
    • He’s trying to create a connection among users in Pioneer similar to religion
      • Religion allows people to feel connected with others and encourages them to assume the best in strangers
    • Gross looks at Pioneer as the X-men mansion
      • “We have all these people with incredible superpowers that don’t mind working together and helping each other”

Gross on Education & Sleep

  • “I think it’s criminal that we ask teenagers to wake up at 6:45”
    • “Adults want to wake up early, but children do not. I think school should start at 11 o’clock. That alone may change the world.”
    • Gross says studies have shown that children need to wake up later than adults
  • In high margin and high demand jobs, work starts whenever you want
    • Software engineers can come in whatever time they want as long as they get the job done
    • Gross recommends people spend 3 months experimenting with what sleep/wake up time works best for them and then committing to that
  • SAT tests may not be the best way to measure intelligence
    • Schools end up “teaching the test” and “may knock the creativity out of students forever”
    • Gross was fortunate to have a principal that turned a blind eye on his attendance as long as he did well on tests
      • This allowed Gross to focus on programming and other creative areas
    • Gross believes that “we need to get the internet as early as possible to people”
      • “It encourages and allows people to follow their passion and dreams”
      • “If we don’t do it, other countries will”
        • Parents do have to balance their kid’s internet usages, ensuring that they don’t become addicted to it, but the internet is not going away, and people should learn how to use it early on

How to Know if a Startup Will Be Successful

  • People work on their pet/passion project, but don’t tell anyone about it – you shouldn’t do this
    • Go and talk to your users and get feedback
    • “You need to create something of value for other people”
  • “The mistake people make is that they don’t talk to enough users because it is psychologically so hard”
  • “I do not think that a perfect founder can defeat a bad market”
    • “If you’re going to start a company, you’re going into the most aggressive version of the video game”
    • “Starting a company is like chewing glass and staring into the abyss” – to quote Elon Musk
      • Gross has seen both sides:
        • Founders that work incredibly hard, but their startup doesn’t succeed
        • Founders that do barely any work, but business is great


  • Friends are incredibly important to Gross
    • Startups have a lot of ups and downs, so it’s good to have friends that will be there for you throughout the journey
    • Even introverts should try to make friends
      • “Pick people that are fun to be around because ultimately you want to be fun to be around yourself, because that is how you get to the top of leaderboards in life”


  • “Sitting and meditating is overrated at this point. The underrated thing to do is be an adult and observe your mind in the moment.”
  • Try to get feedback from people all the time
    • It is really important to make feedback a positive experience for other people because if you don’t, they won’t give you any
    • “You want the critical feedback because you want data on how to be better”
  • Gross believes that the best career decisions are often made while people are on vacation because it’s the only time when people actually reflect on their job satisfaction

Tribal Bonds

  • “Humans are willing to cooperate if they are playing against an AI in games” – If there’s another tribe, humans are able to cooperate more.”
    • This explains why there is so much economic progress during war because people start working together to defeat the other tribe
      • “Us against them, we, all of America, must collaborate to win”
  • Gross jokes that if there were an alien invasion, it would be great because the U.S., China, and Russia would all start working together to defeat a common enemy.
  • The bad thing about social networks is that they allow extremes to talk to each other
    • The KKK in one state can now talk to another KKK tribe in a different state


  • Gross read a study that found teenagers who smoke pot lose about 8% of their IQ which equals a loss of annual income by $15-20K
    • “We just don’t understand this computer [the mind]”
    • Gross isn’t sure that other drugs/psychedelics are helpful either

These notes were edited by RoRoPa Editing Services

Venture Stories : , , ,
Notes By Alex Wiec

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