Ryan Petersen is the CEO and Founder of Flexport. Prior to starting Flexport to fix the user experience in global trade, Ryan was co-founder and CEO of ImportGenius.com, a data-as-a-service business for global shipping. Flexport hit a $3.2 Billion valuation after $1 billion investment led by SoftBank.

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  • Excellence =
    • Curiosity – “It’s a more fun way to live.”
    • Learners
    • Appreciative
    • Have fun
    • “It doesn’t have to be boring.”
  • The importance of writing as a leader:
    • “I write a lot of essays. Some are published. Some aren’t.”
  • Communication:
    • “It’s a huge part of the job of a leader.”
    • For investor updates… “It’s good practice.”
      • Try to use humor, learn something new, don’t be boring, get people “pumped up”
  • Raising money from investors:
    • “It’s like your love life. You have to earn it. There are no shortcuts. You need to have a business that doesn’t need them.”
      • “We built a track record over the 15 years prior to raising money.”
    • Masayoshi Son is the CEO of Softbank. He is a Japanese billionaire technology entrepreneur, investor, and philanthropist. Ryan met with him and earned a $1 Billion investment… Making Flexport worth $3.2 Billion.
    • Flexport became the fastest growing company in Silicon Valley.
    • Ryan wrote an essay about raising a lot of money so that they could ride out a “100 year storm.”
    • How was he able to raise so much?
      • “Don’t do an auction. I said, ‘I’m only talking to you.’ Create a win-win. See the world through their eyes.”
    • Masa had written a 300 year vision. Ryan said, “The audacity to have a 300 year vision, it just resonated with me.”
      • “One of our core values is to play the long game.”
  • Flexport enables all parties to move large product around the world. It was born out of Ryan discovering the pain of shipping.
  • There is a lack of technology with freight forwarders. There was no culture of customer satisfaction.
    • There was high friction – “We counted 984 steps to get a product shipped.”
  • Paul Graham, one of the greatest investors of all time and founder of Y-Combinator said this about Ryan Petersen:
    • Ryan is what I call an armor-piercing shell: a founder who keeps going through obstacles that would make other people give up. But he’s not just determined. He sees things other people don’t see. The freight business is both huge and very backward, and yet who of all the thousands of people starting startups noticed? Ryan Petersen.”
  • By 2016, Flexport was serving 700 clients across 64 countries. Tech Crunch described it as the unsexiest trillion-dollar startup.
    • Flexport has grown to 1,800 employees across 14 offices and 6 warehouses, and 10,000 clients.
  • His goal:
    • “Drive velocity: You need speed in the right direction. Velocity is the key to success. That’s culture ultimately.”
  • The two forms of bureaucracy:
    • Too many rules, order
    • No rules, no process, chaos
  • Need to find the balance between the two
  • “Transparency helps get people aligned.”
  • Doing an open Slack Q&A with all employees — Helps with transparency.
  • What Ryan looks for when hiring a leader? And why Ryan admires Parker Conrad from Rippling:
    • He’s “hungry, curious, has a chip on his shoulder, determined, ambitious, and solves complex problems.”
  • The profession of sales:
    • It’s “one of the most misunderstood professions. It’s part of all jobs. You have to persuade, create value.”
    • “Sales is about creating value for others. Create win-wins. So much is repeat games. Almost nothing is a one time transaction.”
  • Obsession with company culture:
    • “When I reach out to top execs, they always take the call if I’m asking about culture.”
  • The secret to the tech industry:
    • Everyone is willing to share tools, mindset, and lessons learned with one another. It’s “normal to pick up the phone and ask.”
  • How did becoming a dad change him?
    • “It’s exhausting. Babies are fragile.”
  • Generalists vs. Specialists?
    • The world needs more generalists. “Generalists are under-valued. Leaders need to be well-rounded and cross over into multiple disciplines.”
  • Has has Ryan learned to speak 6 languages?
    • Read books, make flash cards, read the newspaper, hire a tutor… “You have to experience pain to learn. You have to like the pain.”
  • Life/Career Advice:
    • Get out of student debt
    • Read books. Your life will be different in 5 years based on the books you read. “Most people don’t read books.”
    • Success compounds – Add up a lot of little wins
  • Apply to be part of my Leadership Circle


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