Totally honest, unpolished real interview. He is figuring things out still which actually is the job description of a CEO. Totally relate to tech stack architecture and org architecture point. He keeps explanation basic and not superficial which is really a good quality

Ryan is one of the most inspirational founders around. I’m obsessed with his mindset and willingness to tackle problems that require “schlep blindness”.

I joined Flexport because of Ryan. Met him during Flexport Academy and he was just a genuine guy with great ideas. I left Flexport two years later for, well, let's say reasons (which had nothing at all to do with Ryan) but I've always had a bit of pride to have it on my resume. What you see is what you get with this guy, he is quite genuine in this interview. I just wish the organisation as a whole could match him a bit better. But I wish the company all the best, no regrets.

I’ve never met Ryan, but he comes across as an amazingly honest person. And I think this honestly goes a long way as a character feature in an entrepreneur. Thanks Gran for the interview, it was awesome.

The reason this chat is so valuable is that very few people actually talk about the difficulties of the growth stage, and so there are many less signposts to show you if you're doing a good job, and what the errors are when a pile of cash just got thrown at you. This makes the talk more full of good nuggets of info / anecdotes, so thanks for that.

You can just tell by the way he speaks that Ryan has so much knowledge, starting with a 30k foot view and then diving deep into each topic. Loved this interview!

We once had a townhall with the CEO of Kuehne+Nagel, when asked if Flexport is a worthy case study to re-evaluate the traditional business model but long story short he said Flexport is nothing to be afraid of as a competitor. I honestly can't wait to see Flexport grow beyond expected.

This was fantastic! It’s been great to see Ryan step up to demystify the supply chain crisis over the past 18 months and the clarity with which he spoke about Flexport’s ambitions and business model reminded me of Brian Chesky’s Masters of Scale interview. Will be following Flexport’s story even more closely now 👍🏼

As a startup in the country of Indonesia, this was a wonderfully insightful interview and I thank you Garry for the work you are doing to empower others. listening to real people being open and candid allows me to trust the process and know I'm not alone in the day-to-day highs and lows of building a company. Ryan good on you for not holding back the real I learned a lot and can relate to you sometimes not knowing but keeping going. Garry if there is ever a time you would like to interview a guy building a startup in this beautiful country of Indonesia I am your guy.

So many good points, its hard for me to list all. But the point about setting up your life so you don't have the pressure of having just 18 months to make it happen really resonated with me. Also the point about taking service oriented architecture and applying it to the business teams as well was insightful. Fantastic and honest interview.

Very bold comments about the culture behind funding rounds. I appreciate that you let us hear that, and not just cut that piece out! High-quality content right there!

Garry - I absolutely love the candor and authenticity you bring out in people. 🙂

Thanks for coming back

Such a refreshing and realistic view on building a great company. I personally hate the idea of bureaucracy but for big companies it actually does keep things running smoothly provided each part of the process is efficient.

Amazing content as usual but this one is a new level of great. Love Ryan & Flexport. Super inspiring

Ryan is really inspiring; saw a talk from him a couple weeks ago in New York. Great pick Garry!

That makes me want to work for him. His passion is contagious.

This is one of the best interviews I've ever seen, just from an honesty standpoint

really good interview. Thank you gary for sharing this meeting with ryan. Gave us alot of insight into his operating philosophy

Love your videos Gary! Thank you for bringing these videos to us!

I really like it when you bring Startups founder to the channel, unlike traditional Tech media, they feel so relaxed talking to you that they pour out their heart,plans and ambitions. You give them time to talk and don't interrupt their thoughts with questions. Honest conversation 👍.

This. Guy is so real ... Like no cap

Great another hour video I need to watch so much good content to consume

I haven't been watching your videos for very long, but I feel smarter already. Thanks

Wow! This is game changing. Ton of experience. Kinda delivering benefits while laveraging awesome returns.

I’m a YC alum (S18) and I feel so blessed to be a member of the YC community. I have to disagree with Ryan that YC is a 90-day pressure cooker environment and if you fail to raise money, your company dies. It’s totally possible to remain in “cockroach mode” until your company figures out product-market fit. Even more so now since YC’s new $500k deal provides plenty of runway! The problem is that founders who fail to raise money from investors at demo day get demoralized (especially when their peers are all raising huge amounts of money) and give up. I would argue most start failures are exactly that. Not because the company failed to find product-market fit, but because the founders decided to throw in the towel.

Thank you for this, I am ready to see it and enjoy it all, as always

Loved the honest interview! If Ryan weren't CEO at Flexport he could have been Captain America..

production value is off the charts!

World class content, thank you for this.

Practical & perfect example of Conways Law & decomposition of teams/services according to business capability

Wow I'm a solo founder and this gave me great perspective

Great interview Garry - I got a lot of actionable insights from Ryan.

Another Genius, Awesome interview! Ryan is a friggin legend! 👍🏽🙏🏽🦉🤝🏽

No bullshitting CEO here. I appreciate the honesty

Amazing interview, thanks for sharing this.

Great as always

Few seconds in and I can see the upgrade in the camera quality 👍

Amazing! Thanks for sharing this!

I thought you Quit!!! Welcome Back 🥳🥳

Love this!

more of these entrypoint please, thank you garry!

It’s clear as day that Ryan and Flexport are destined for greatness. Loved this man’s attitude and insights, he is personable, honest, and down to Earth. I would love to work for him, his sincerity is a breathe of fresh air!

This is far the best channel on KZfaq 👍 👌

Brother Gary that was awesome. 🤝🏽🦉

This guy seems incredibly smart and hardworking. Aggragating ship container data? Who thinks of that? I'm a small business owner. How do I get my manufacturer on board? My business is scaling dramatically over the next 3 years.

Great questions!

Ryan is an inspiration!

Thanks Gary

How is this knowledge free? Thanks for making and sharing this.

Always a good interview when Ryan's on.

Amazing vid

Garry Is Back 🙌🏾🙌🏾🙌🏾

Just fabulous.

Insane interview and tons of value! But no one's going to talk about Garry's new look ??? That boy lookin cleannnnnnnn!

Boom. From the *moment* there was anything at all to learn about Flexport back in the day, I *knew* it was one to watch. Here's a takeaway from *so many* successful YC/Initialized alums: find something with processes that can be improved, innovated, or eliminated. If you find a massive manual life cycle somewhere, pick a linchpin process and make it better than it's ever been. You will have edge cases become core cases with everything you solve, and at least two customers for every solution you build.

Garry This set up 🔥🔥🔥🔥

Loving the shirt Gary!

Wow. I cannot WAIT to watch this!!

is there a way for us to invest in this company? it is not publicly traded. I watched years ago some ycombinator video. this guy is so interesting and his story with flipping bikes still amazes me. best wishes to you.

What’s the white capsule behind them?

Have missed your contents in a while Garry

I have been working on achieving exactly this. Would be amazing to sit down with these gentlemen for a chat.

How do we apply to Initialized VC

Hearing Ryan speak is Steve Jobs level good.

Garry always bring the best guests🔥

LEGENDARY

Inspiring. But Growth to be consistent cost control is required... like many of our customers acknowledge. Technology + Outsourcing is the future.

can someone help me with the concept/mental model which Ryan talks about when he says that the valuation of his company is the probabilistic weighted sum of all the different possible valuations?

This is such as fantastic interview for many reasons. Ryan's knowledge of designing and managing a business is spot. my summary notes and key take away's are: 1. having a small and robust company is better than a company forced to scale within 18 months, success becomes almost guaranteed rather than by way of market swings 2. power law dynamic for the chain of teams is explored, having highly specialized people in important key sectors and ruthlessly automating out friction along the way 3. Tech debt is a major problem explored in this interview and prevent companies from being flexible in the future. He goes on to say that their top competitors were created before Netscape and run on ancient mainframe software that are difficult to overhaul. He stated it is easier to start from scratch in this context. He also shares this concern with his own company where other new companies can overthrow Flexport if they don't build flexible processes and architecture 4. One of the biggest takeaways is maintaining a fine balance between being scrappy and execution oriented and having solid processes & culture, Ryan reflects on his journey of being an entrepreneur avoiding Bureaucracy all costs. He has come to reconcile this with the added value to processes. He imagines an ideal architecture to reap the benefits of both would be a small focus groups that solely work on driving a few metrics and while being integrated within the system that communicate with other focus group. My only concern from Ryan is how far he is willing to go about architecting these focus groups, having context is important and surely his upper management team is handling that well for now but when will it get too far? If the encompassing strategy is owned by those at the top negative sides of human nature could start rearing its ugly head and bad decisions or judgement will be exasperated that much more further.

👍

Wow

Wish Flexport can streamline the supply chain crisis as it is designed to.

Great !

Hi, I'm CEO of Elexion: Digital platform that provides information on emerging problems in the city of silicon valley so that Latin American Entrepreneurs can select what they want to solve. What problems are occurring?

11:50

Who’s place is that? Looks great

Welp looks like I gotta go make at least $8B to get an interview with Garry...the quest begins

Garry you're looking handsome bro

Damn, you look good, Garry.

🎊🙌🙌🙌❤️

For some reason Ryan normalized "not knowing it all" and being vulnerable with accepting failures.

25

Providing data to shipping companies !? That is it ?

I don't know why I am scared to talk to VC or investor. I don't know who is he

Wow! Talk about someone who knows his shit and knows when he doesn't

flex flex

Who gave this guy any money!?

2nd here

Burning other people money is awesome !

He should use the blockchain for what he is doing.

Flexport is a scam

@GarryTan I have watched a lot of CEO/Founder interviews as an entrepreneur. I have never seen a more honest, relatable interview! @RyanPetersen is the real deal. He shares his opinions in such simple language that you do not need to know his industry to understand his vision.

I really like it when you bring Startups founder to the channel, unlike traditional Tech media, they feel so relaxed talking to you that they pour out their heart,plans and ambitions. You give them time to talk and don't interrupt their thoughts with questions. Honest conversation 👍.