Bill Gurley (Benchmark)
Bill Gurley (Benchmark)

Bill Gurley (Benchmark)

Runnin' Down a Dream: How to Succeed and Thrive in a Career You Love

Original Upload Date: 09.14.2018

Context: Bill Gurley is a General Partner at Benchmark, one of the best venture capital firms in the world. In September of 2018, Bill returned back to the University of Texas McCombs School of Business to present a powerful speech around how people should think about their career journey.

This is my transcript and notes from Bill Gurley's speech. Everything is from the perspective of Bill Gurley.

Last updated: 07.30.2020

// @blakeir


Table of Contents

[2:50] Intro

Believe it or not, I've been thinking about giving this particular presentation for about a decade. I was inspired after studying the stories of three people that you might call luminaries...I noticed an overlap pattern amongst them.

What is a dream job?

It means chasing a career where you just have immense passion.

Kevin Harvey: "Life is a use it or lost it proposition"

Most people only take one career path, but if you've got one shot — why not do what makes you happy?

Why am I speaking to you today?

I'm speaking to a room full of MBA students because you all have an amazingly unique opportunity ahead of you.

You've had your undergrad degree.

You've work a little bit, and now you have a chance to go do whatever you want.

It's an amazing pivot point...

[4:25] Luminary #1: Robert Montogomery

[4:45] Background

  • Grew up in Orville, Ohio (1940)
  • Attended Orville High School where hewas a three sport letter man: baseball, football, and basketball.
  • One of Robert's neighbors was Fred Taylor, the basketball coach for Ohio State, so he was able to get a spot on a really good basketball team.
    • Robert wasn't a starter.
    • He didn't get a ton of minutes, but they won the national championship his sophomore year.
  • After college, Robert went into coaching...
    • He spent his first year as a Junior Varsity coach at a high school, and then he finagled his way onto the staff at Army.
    • At 22, he became an assistant for Army's basketball team.
    • When he was 24, the head coach at Army retired. He begged for the job.
  • At 24...he became the head coach of a D-1 school (Army)

[5:58] Robert Montogomery's Dream Job?

From my point of view, it isn't what happened inside the four walls of the gym where they practiced every day. Instead, it's what he did outside.

In the first five years of his coaching career he befriended five of the top basketball minds on the East Coast:

  • Red Aurbach (Head Coach — Boston Celtics)
    • Robert got connected to Red through his relationship with former college teammate John Havlicek, who went on to play for the Boston Celtics.
  • Joe Lapchick (NBA player & Head Coach)
  • Clair Bee (Head Coach at Long Island University)
    • Clair has the best record of any coach in the Basketball Hall of Fame.
    • Robert met Clair when was 25.
    • Two years later, when Robert was 27, he drove Clair to Clair's induction into the Basketball Hall of Fame and sat next to him.
  • Henry Iba (Head Coach — Oklahoma State)
    • Coached 36 years at Oklahoma State.
    • At the time, he was one of the most successful coaches.
    • For both Lapchick and Iba, he just went to a coaches' lucheon where he knew they were going to be, and he begged them to let him sit next to them. He kept following up and hanging out with both of them.
  • Everett Dean (Head Coach — Indiana)

He continued to network outside of just the East Coast...

  • Pete Newell (Head Coach — University of San Francisco)
    • Pete was the greatest basketball mind on the West Coast at the time.
    • They became fast friends.
    • Years later, Pete would induct Robert into the Basketball Hall of Fame.

He didn't limit his peer network to just basketball coaches...

  • Bo Schembechler (Head Coach — University of Michigan)
    • Bo was Robert's assistant on the basketball team at Army
  • Bill Parcells
    • Robert met Bill long before he became a star coach in the NFL.
  • Doc Counsilman
    • Long-time swimming coach at Indiana, someone that Robert was good friends with.

[7:52] Who is Robert?

I'm using the name Robert to obscure things a little bit. I'm talking about Bobby Knight...

At the age of 31, Bobby Knight became the head coach at Indiana University.

  • Five years later, at 36, they went undefeated, both in the regular season and post season, and won the national championship. That's never been repeated over four decades.
  • At Indiana, he accomplished a lot:
    • Three national championships
    • Four coach of the year awards
    • 11 Big 10 titles
    • When he retired, he had 902 victories, the most of any coach at the time.
  • Pete Newell later inducted Bobby Knight into the Hall of Fame.

[8:34] Luminary #2: Robert Zimmerman

[8:45] Background

  • Grew up in Hibbing, Minnesota.
  • Robert always loved music.
  • He got a guitar when he was 10 years old, and by high school he was playing in a band regularly — they used to cover Elvis and Little Richard.
  • His yearbook says that he's likely to join Little Richard. That didn't happen.
  • He went to the University of Minnesota, but he didn't go to class. Instead, he was hanging out in a place called Dinky Town.
  • Even though he grew up playing rock and roll music, he started to fall in love with folk music.
  • Over the course of eight or nine months, he studied every folk album he possibly could.
    • He didn't have a lot of money. At that time, you could walk into a record store and listen in a booth. He would do that for hours and hours and hours.
    • He became friends with people that also liked folk music, but had money. He would go to their house and listen to their record collection.

[10:00] Robert Zimmerman's Dream Job?

Robert did an incredibly ambitious action to pursue his dream job...he hitch-hiked from Minneapolis to New York City. He had a guitar, a suitcase and $10...and it's a 1,200 mile trip.

If you ask him today why he did it, he would say that he was chasing the performers (Dave Van Ronk, Peggy Seeger, the New Lost City Ramblers). He was listening to them in Minnesota, but these performers were in New York City, and he wanted to see them.

There was really one person that he wanted to see: Woody Guthrie.

Woody Guthrie had become his hero. He wanted to know everything possibly could about Woody.

He went to New York. He found Woody Guthrie. He used to perform for him.

Then Robert started hanging out at three specific venues: Cafe Wha, The Gaslight Cafe, and Gerde's Folk City.

This was the epicenter of folk music at the time.

He would sit in each of these venues for rhours upon hours and study what the other artists were doing.

Years later Liam Clancy would say: "He could perform any one of our songs like us, including tonality, tempo, everything."

He was studying, studying, studying.

He finally got his big break when was asked to open for John Lee Hooker at Gerde's one day. That's when his career got started.

Joe Hammond, the producer for Aretha Franklin, Billie Holiday, and Count Basie, walked into one of the venues and discovered Robert Zimmerman (1961).

[11:54] Who is Robert Zimmerman?

A year after working with Joe Hammond, Robert Zimmerman changes his name to Bob Dylan.

Bob Dylan releases his first album. It does okay.

In 1963, they released "The Freewheelin' Bob Dylan." This album goes to number 22 in the U.S. and number one in the U.K. From there everything was off and to the races. He later performed at the march on Washington with Joan Baez where Martin Luther King spoke his famous speech.

A year later, in 1964, he performed for the first time with Johnny Cash, another one of his hereos.

Johnny gave him a guitar and asked Boby if he could record several of his songs.

The rest is history. Bob Dylan's accomplishments:

  • 100 million albums sold
  • 11 Grammys, an Oscar, an Emmy
  • Rock and Roll Hall of Fame
  • Kennedy Center Award with Clinton
  • Barack Obama gave him a Medal of Freedom
  • He won a Nobel Prize in laterature — the only musician ever to be given such an award.

[13:07] Luminary #3: Daniel

[13:18] Background

  • Grew up in Saint Louis, Missouri
  • His father was an intelligence officer in the miltary, and moved around Europe quite a bit.
  • After the war ended his father became a travel agent, and his mother worked with him. This meant that they traveled quite a bit.
  • Now, because they were travel agents, his mom told him he had to journal everything. So he was forced to go on vacation and take notes.
  • He wasn't that interested in travel, but he LOVED food.
  • When he went back and looked at all the journal notes he had always taken, they were always about the food they were eating while traveling. He started to associate different places with the food that he went to.
  • He went to John Boroughs Hill School in Saint Louis. Ended up at Trinity College in Connecticut, where he would spend every weekend in New York City eating food because that's what he was passionate about.
  • He got a poly-sci major, and went to work on a campaign for a year...but that wasn't interesting to him, so he went back to New York.
  • He went to work at Check Point — they make those things that you attach to clothes in the store so that when you walk out the beeper goes off.
  • He did incredibly well at Check Point, and within a year was making $125,000/year as a salesman.

[14:40] Daniel's Dream Job?

One night Daniel was out to eat with his uncle, his aunt, and his grandmother. He told them that he was studying for the LSAT.

He was going to take the LSAT next year and go up his career ladder again and become a lawyer. His uncle replied and said: "Will you just stop it? Why don't you go open a restaurant? You know that's what you're supposed to do..."

It caught him a bit off guard, but it woke him up.

He took the LSAT, but never sent the scores to a single school. Never applied to a single school...

He quit his job as a salesman at Check Point, and went to work at a restaurant called Pesca in the front office for $12,500/year. He took a 10x salary reduction.

  • The reason he chose Pesca is there was a chef there, an up-and-coming chef called Michael Romano. He wanted to be around this genetleman.
  • He would work during the day in the front office, and then at night he'd beg to do the slop work in the kitchen just so he could get exposure to what was happening there.
  • He was also taking a wine class at night, and he met this gentleman who happened to be the head or one of the top restaurant critics for the New York Times. They started hanging out together and going to different restaurants and talking and learning.

Daniel did something really interesting. He made a list of 12 icons in the restaurant industry. These were new people that were doing innovaive things around opening new high-end restaurants.

Wolfgang Puck is the first one, but there were 12 different ones.

A lot of these people are on celebrity chef shows today.

He started studying them. He created a notebook for each and everyone of them — what makes them special? what do they do unique? He started looking their recipes.

Then he got even bolder and decided to go to Europe...

He went to europe and did a stagiaire, where he worked in a restaurant for free. One of the restaurants he worked at, he actually had to pay $500/month. He went from making $125K to $12K to now -$25K...

He studies each and every one of these places:

  • He's watching the chef.
  • He's watching the recipes.
  • He goes on sourcing trips to see how they pick food out of markets or from different fish markets.
  • He just takes tons of notes.
  • He looks at the decor.
  • He looks at the wine list.

On the way home from his nine-month journey, he said it took the entire eight and a half hour flight just to organize the notes.

When gets back to New York, he spent another six or seven months searching a hundred locations to find the very best location to launch his first restaurant.

He was 27 years old when he opened Union Square Cafe.

[17:58] Who is Daniel?

This is Danny Meyer, for those of you who might know who he is. I love this quote from Danny:

"I spent nearly two years doin the best work ever as a student."

Danny is most proud of the studying he did on his own, not the studying that he did at Trinity College. He viewed this as the best work he had ever done as a student.

Union Square Cafe is still open today, 11 times Zagat has said that it's the very best restaurant in New York.

Danny Meyer would go on to launch 16 high-end restaurants in New York City, four have won Michelin Stars.

Danny is the undisputed king of high-end restaurants in New York City, but he wasn't done.

Danny had a philosophy that if he could build a restaurant it could become the bespoke place that people go, and then the community would evolve, and that he would get a lift alongside that.

He would typically look for areas that were on the rise, but needed help.

One area that needed a lot of help was Madison Square Park, which wasn't far from Union Square.

Danny and a bunch of other business people helped launch the Madison Square Conservancy that rebuilt the park.

A few years after that happened, they started improving the park.

There was a decision made to allow there to be a restaurant in the center of the park. Danny applied, got the bid, and won.

That was the first location for Shake Shack.

I got to know Danny on the OpenTable Board. We worked together for over a decade. He used to tell me that I had to keep it a secret, but that single venue for Shake Shack made way more profit than any of the white table cloth restaurants that he owned.

Fast-forward to today:

There are over 190 Shake Shacks in the world.

In 2015, they took Shake Shack public on the NYSC, and it's now worth $2.2 billion.

[20:10] The Five Guidelines

These were the three stories that I wanted to cover.

I had read all of their stories independently and I noticed there was similar strain that was running through each and every one of these stories. These are the five major strains.

[20:22] 1. Find Your Passion

My first piece of advice would be to find your passion. Pick a profession in which you have a deep, personal interest.

There is nothing that's going to make you be more succesful than if you love doing what you're doing. That is because you're going to work harder than anybody else if it doesn't feel like work. It's going to feel fun.

  • I think this is the most important decision you can possibly make in a career — make sure you have an immense passion for what you're doing.
  • This should be YOUR personal passion, not your parents, not your sister's, not your family generation of expectations. It needs to be something that you're doing on your own.
  • Don't make this decision based on status and compensation.
    • There are a lot of high-profile careers that make a lot of money, and they are generally perceived to be areas where successful people go. If you run at those things and don't have a passion for them, you're going to burn out eventually. It's not going to be where you want to be.
  • You can't fake passion — someone else, that really loves the job, will out run you.
    • Somebody else sitting in some other MBA program has a deep passion for whatever career path you're going down, and they are going to smoke you if you don't have it yourself.

One of my favorite quotes from Bobby Knight is: "The key is not the will to win...everybody has that. It is the will to prepare to win that is important"

  • Everybody has the will to win. People don't have the will to practice.
  • This is the test for whether or not you're actually pursuing your dream job, which is the essence of it that would be considered studying or work or practice, do you enjoy that part? Do you enjoy the preparation?
  • Everybody enjoys winning. Do you enjoy the preparation?

[22:14] 2. Hone Your Craft

Hone your craft constantly... It's extremely important to be obsessive about understanding everything you possibly can about your craft.

Consider it an obligation. Hold yourself accountable. Keep learning over time. Study the history, and know the pioneers.

  • It's the bedrock foundation for what you're going to build upon, and it will help you in networking that you're able to talk the language of the people that came before you.

Strive to know more than everyone else about your particular craft.

  • Let's say you love esports. You've decided multiplayer gaming esports is your passion.
  • Within the first six months of being in this program, you should be the most knowledgeable person at McCombs in esports. That's doable. You should be able to do that.
  • By the end of your first year, you should be top five of all MBA students, and, hopefully, when you exit your second year, you are the number one of any MBA student out there.
  • This doesn't mean you're the best esports perosn in the world, but you've separated yourself from everyone else that's out there.

I can't make you the smartest or the brigthest, but it's quite doable to be the most knowledgeable.

  • It is possible to gather more information than somebody else, especially today.

Depending on what it is that you're chasing, you might want to go to where the epicenter is.

  • The reason is there's just more networking available there if that's where the great people are.

Bobby Knight Quote:

"So in the spring of 1972, I went to Pete Newell's house and I sat down in the middle of the floor, with a stack of three-by-five cards that I used to diagram each separate option...I filled out seventy-four cards with what could be done..."

  • The second time that Bobby Knight met Pete Newell, Bobby sits down in the middle of the floor and says: "Hey, Pete, come go through these with me." I don't know if it's audacious or brilliant or what, but to get your number one mentor you can possibly find and make them go through that amount of tedious work, but he did it. Pete did it. They both learned from it, which is interesting.

'No Direction Home' Quote:

"In the film ("No Direction Home") he rightly calls himself "a musical expeditionary." Tony Glover, who recorded a young Mr. Dylan in Minnesota, is also right when he calls him "a sponge." There's ruthlessness in the way Mr. Dylan finds sources, uses them and moves on; the reuthelessness of an artist's best instincts."

  • Most people would think, "Eh, Bob Dylan, folk singer. Probably just had the DNA, or got lucky or something." He was studying. He used the words, "I'm a musical expeditionary." I looked up expeditionary. An expedition is to travel for scientific research or exploration. That's what Bob Dylan was doing. There is no one that knew more about folk music than he did when he broke out. He knew more than anybody.

Book: Setting The Table by Danny Meyer

He has a restaurant in New York called Blue Smoke, which is actually a barbecue place. When they were thinking about launching that he says:

"In the barbecue, within the 35 mile radius of Austin and the Texas hill country lie five towns I revere. Each with a distinctly different style of barbecue. The elements of barbecue are limited: ribs, brisket, pulled pork, chop mince pork, sausage, chicken, coleslaw, beans and a handful of sides, but it's become an American culinary language with thousands of dialects and accents.

I tried to understand each variation.

During one 36 hour road trip through North Carolina I tasted 14 variations on chopped pork, each defined by subtle and dramatic differences in texture, the degree and type of smoke used, the amount of tomato or vinegar in the sauce, how much heat was applied to the meat and how well or how much or how little crackling got chopped up and tossed in.”

  • That is the level of detail that he thinks about with food. I really want to drive home this point of studying...

I really like this quote because it has to do with Shake Shack:

"As soon as we won the bid Richard Corrine, my most enthusiastic researcher of road food, and I set off to study burger and shake stands all over the country. We started out, of course, at Ted Drew's Steak and Shake in Saint Lewis...Continued on to Kansas City, and individually made stops in Michigan, Culver's, Los Angeles, In-N-Out Burger, Napa, Taylor's Automatic Refreshers, Chicago, Gold Coast Dogs, plus eight other establishments...Always in search of the best of breed.”

  • That's how they did research for Shake Shack. I think it drives home this point of: understand more than anybody else.


Picasso was a trained classic artist and had mastered it by the time he was 15. He had spent time studying the way you would if you had set out to be the greatest painter in the world, and that's why I made this statement:

Greatness isn't random. It is earned.

If you're going to research something, this is your lucky day.

Information is freely available on the internet — that's the good news. The bad news is that you now have zero excuse for not being the most knowledgeable in any subject you want because it's right there at your fingertip, and it's free, which is excellent.

[28:30] 3. Develop Mentors In Your Field

I don't know if any of you will ever dare to be as aggressive as Bob Dylan — hitch-hiking 1,200 miles to find your mentor, but that might be the type of attitude you want to think about in the back of your mind as you pursue mentors.

Take every chance you can to meet people that are known for success in the field that you have chosen.

  • You can work your way up the stack. You don't have to jump straight to the top on day one.
  • Treat them with respect. Debate things, learn from them. Document what you hear, and share it with others.
  • Ask them all of the questions that you can.

Try to get these mentors interested in you and your own development.

  • Send them notes.
  • Tell them when you use their advice to be successsful.
  • Send them gifts when you have accomplishments.
  • Get them bought in.

Never stop pursuing mentors.

  • This advice isn't just at the beginning of your career, but all the way through the end of your career.
  • I had the remarkable fortune this year in my 20th year as an investor to meet Stan Druckenmiller and Howard Marks. They're two people I've admired for a very long time. I read everything that they write. I got to sit down with both of them for a couple of hours and talk about investing. It was awesome. The things that they pushed on, changed some of the action that I'm taking today in my work.

The Three Luminaries

  • I have already walked you through each of these examples. Every one of these luminaries had a mentor that was important to them.
  • I texted Danny Meyer when I was preparing this presentation and said: "How many of those 12 icons have you ended up establishing a relationship with?"
    • He said that four of them have become close, personal friends.
    • I think it just documents the point I'm making about how searching for mentors and leaning on mentors is a never-ending task.

[31:00] 4. Embrace Peer Relationships In Your Field

Develop deep relationships with peers that are on the same journey as you.

  • Have discussions and debates about what defines greatness in the field. Don't be afraid to argue passionately.
  • This is the one thing that I wish someone had told me. When I got to MBA school everybody said: "Network, network, network," and I thought it was a social activity. I thought they were telling me, "Oh, you need to develop your social skills," and they want me to randomly talk to people that I have no similar interests with.
  • What I've come to realize is, no, it's not about that. It's about connecting with the people that you have the most overlap with because you'll be able to help each other along the way, along the journey.

Always share best practices and don't worry about any proprietary knowledge. It's not a zero-sum game.

  • It's just good trade. It's just smart. If you get caught in worrying about it, you're going to fail to advance.
  • The activity of sharing with mentors and peers will lead to so many positive things that will help you go up, that whatever the negative costs are — they aren't going to come anywhere close.

Celebrate your peers' accomplishments as if they were your own.

Peers don't need to be in your exact field.

  • Bobby Knight had sat down with a swimming coach and got knowledge.
  • Some of the entrepreneurs I work with and CEOs find that it's more interesting to go to a conference on a topic that's a little bit far away because they get more innovative ideas that they can bring back to their field.


  • Most of you know that this is the way you're supposed to network online, and you should certainly have a LinkedIn profile.
  • I'll give you one piece of advice, which is, be a little stingy with who you link to.
  • I have a rule where I only want to link to people that I would call and trust their advice because then when I'm searching for a candidate that I want a reference on or something I don't get random answers.
  • I think people over proliferate their LinkedIn account.


  • I think there is a much more incredible resource for networking: Twitter
  • Twitter is the most amazing networking and learning network ever built.
  • For someone that's pursuing their dream job or chasing a group of mentors or peers it's remarkable.
  • In any given field, 50-80% of the top experts in that field are on Twitter. They are sharing ideas, and you can connect to them and follow them in your personal feed.
  • If you get lucky enough and say something they find interesting — they might follow you. If you can unlock opportunity to direct message, you can communicate directly whenever you want with that individual. Very, very powerful.
  • If you're not using Twitter you are missing out. I don't even own any shares anymore.

[34:14] 5. Always Be Gracious And Humble

ALWAYS give the majority of the credit to the mentors and peers that helped you along the way.

  1. It's the right thing to do.
  2. It keeps you from being an asshole when you're successful.

Send letters, send gifts, anytime you accomplish something in your career. Take the time to send messages back to the people that helped you.

Eventually you have to pay it back. Become the mentor for others that are coming up the ladder.

  • Bobby Knight Quote:
  • "What he (Pete Newell) represented to me in this case was the responsibility a teacher has to share with others...I never held anything back at clinics or in conversations with fellow coaches, especially young ones."

  • Bobby Knight Example:
  • Shortly after one of his sessions with Pete Newell and the next year Indiana's playing one of Pete's teams. They end up in a tournament together. Bobby uses the stuff that Pete taught him and beats Pete on the field. He recalled that notion in the book, and he said, "You know, if Pete was willing to do that for me, I've got to do that for everybody else."

Let me show you statistically a little bit of the impact of what Bobby did later in his career. This is from his Wikipedia. These are Bobby's former players that are coaching either D-1 or NBA, and this is his former coaches that are coaching D-1 or NBA.

  • It's an immense legacy of people that he developed that went on to be successful.
  • Bobby Knight's point guard at Army was Mike Krzyzewski, who is one of two people that have now passed him on career wins, 902.
  • Kryzyzewski asked Bobby Knight to induct him into the Hall of Fame.

Danny Meyer quote from his book 'Setting The Table'

"I am convinced that you get what you give, and you get more by giving more. Generosity of spirit and a gracious approach to problem solving are, with few exceptions, the most effective way to earn lasting goodwill for your business."

[37:03] Luminary #4: Sam


  • Grew up in Marlow, Oklahoma.
  • Sam went to Marlow High School, where was a multi-sport athlete. He was 5' 9" and 140, so he didn't get to keep playing in college.
  • He went to the University of Oklahoma, and then he ended up going to Bain. I think he actually worked at Bain Capital.
  • He was pursuing his career path like he thought he was supposed to.
  • Bain relocated him to Sydney. He's sitting in one of these high-rises overlooking the Sydney Opera House, and he hears about this book, Moneyball by Michael Lewis.
  • Sam reads Moneyball in three days. He can't get it out of his head. It's consumed him.
    • He decides immediately that this is what he needs to do.

The Pivot Point:

  • Sam starts applying to business schools. He gets accepted to Harvard and Stanford.
  • Sam told both schools that he was looking to get a job in sports analytics, and made his decision based on how they offered to help.
    • Harvard looked at him like he's crazy.
    • However, Stanford said: "Come on. That'd be awesome. We want to introduce you t oeveryone that we know."
  • Sam shows up at Stanford Graduate School of Business...and they have a sports management class.
    • Billy Bean from the Oakland A's (Moneyball) is speaking his first semester.
  • Sam gets to know Billy Bean. Billy Bean introduces him to Michael Lewis. They start spending time together. Michael lives in Oakland.
  • Stanford introduces Sam to people at the Niner's organization, and several sports organizations all over the country. He combines it with hard work.
  • Sam says that he sent a hundred letters out to get a summer internship. He ended up with one at the Texans.
  • After he gets back from his internship, Michael Lewis asks him to come over and talk football because he's working on the Blindside. Sam ends up helping Michael Lewis on Blindside.
  • Eventually, Sam ends up working with the Houston Rockets. He spent two and a half hours interviewing with Lex Alexander. Lex hires him at 27 years old...
  • Nine months later, the Houston Rockets hired Daryl Morey. Sam and Daryl worked together for seven years.
  • The two of them built the best basketball sports analytics department in the country.

Who is Sam?

At the age of 35, Sam Hinkie was named the general manager of the Philadelphia 76ers.

This is only nine years after he read Moneyball...

For those of you that know the story, there's some good and some bad.

  • Sam and Daryl spent a lot of time studying the ways that you could turn a program around.
  • If you're in a particularly tough spot, the only way to do it is to shed your talent, improve your salary cap room, let your young players get tons of playing time, and win through the draft. That's the plan that Sam took.

Sam is all about the long-term, not short-term.

This strategy led to three of the worst seasons in the history of the NBA, but it also led to the drafting of Joel Embiid, who has become a close, personal friend of Sam's.

Eventually, the ownership got tired of this strategy and cut ties with Sam. About that exact moment in time, everything started to get better. They started winning.

Today, for those of you that know, Vegas has the Sixers as the number-two team in the East right now.

Kevin Durant on the Sixers:

"They are going to be a load coming here, next year, year after that, they are going to be pretty good. You are seeing now the team that you should start following now, start paying attention to."

Charles Barkley on the Sixers:

"If Embiid can stay healthy, and Ben Simmons stays healthy, they are going to be terrific for the next 10 years."

Three years are bad. 10 years are good. That's a pretty good trade if you're willing to make it.

"Trust the process."

Sam is now hanging out with startups, venture capitalists, etc. debating his next move.

[44:11] Luminary #5: Katrina Lake


  • This one is very near and dear to my heart. There is an executive that I work with named Katrina Lake.
  • She grew up in San Francisco, but she went to high school in Minnesota.
  • She went to Stanford, thought she was going to be pre-med. She ended up not liking it very much, and got an economics major.
  • Katrina went to work at a consulting firm called Parthenon.
    • They had a number of clients in the retail and fashion space.
    • She noticed that she had an affection for that and started hanging around those clients and focusing on those clients.
  • While she was visiting her retail and fashion clients, she kept asking herself questions:
    • Why does this work this way?
    • Why are these clothes out here?
    • Why isn't there just like one here, and you press abutton and then it's put into your dressing room because you keep all the inventory in the back where you could stack it better?
    • She just kept asking...why?

The Pivot Point:

  • Finally, she decided: "I'm going to do something about this."
  • She came up with a notion of a company that would be a personal shopper for everybody.
  • She didn't quite know how to launch it, so she decided to use her MBA program as a way to launch it.
  • She ended up at Harvard. The first thing she did was scoured LinkedIn and the alumni directory to find anybody that had anything to do with fashion.
  • She was mostly interested in sourcing and merchandising because she didn't have any knowledge there.
  • She found all kind of contacts in New York...
  • She eventually found two founders that had launched startups: Joann from Trunk Club & Craig from Shop It To Me
    • She got them on the phone. She wanted to hear if what she was thinking about was different and better than what they had done, because she wanted it to be different and better.
  • For her summer internship, she went to a company that we were invested in called Polyvore, which was a social fashion site where people aggregated likes on the web.
    • Sukhinder Singh, who had run a huge chunk of the revenue at Google, was CEO there, so she built that relationship.
    • She also got to study how fashion websites spend time with bloggers.
  • After graduating from HBS, she came to San Francisco to launch her company.

Who is Katrina Lake?

  • Katrina Lake is the CEO and founder of Stitch Fix...
  • After moving to San Francisco, she did two things that are miraculous for me from a mentoring standpoint:
    • She found Eric Colson — he ran all of data science at Netflix. He had recently retired and was looking for something to inspire him and she did. He became an advisor.
    • She found Marka Hansen — Marka was at GAP for over 20 years running merchandising, marketing, etc. Marka was very excited about helping Katrina. She is still on the board today.
  • Then...she found two other people:
    • John Fleming, who was the CEO of
    • Julie Bornstein, who was the CMO at Sephora — Julie joined the board.
  • Katrina succesfully recruited Eric and Julie off the board and into the company. They both work there.
    • Julie Bornstein was the COO
    • Eric Colson is the Head of Data Analytics.
  • How Stitch Fix Works:
    • You fill out a 15 page profile about yourself.
    • You give a lot of information, way more infromation than any other retailer has on you.
    • press a button. A stylist looks at your profile and picks five items.
    • The stylist is sitting in front of a dashboard.
    • There's a keep score for every single item in our inventory for every single shopper that's out there, unique to that individual shopper.
    • As you buy more, the data science studies what you like, what you don't like, and that's how the system works.
  • I was lucky enough to become an investor in this company...
  • Forbes called her, "Fashionista Money Ball"
  • In their third year of business, Stitch Fix was profitable.
  • Stitch Fix only consumed $20M of venture capital in the company's life. By the time they went public, there was $100M in cash on the balance sheet.
  • At year five, she hit a billion in revenues.
  • At age 34, she became the youngest female founder, CEO ever to take a company public.
  • I think one thing that really differentiates Katrina, is how she's been able to use the platform to speak out on social change.
    • 31% of our engineers are women
    • 60% of our board are women
    • 62% of our management team are women
    • 86% of our entire org are women
  • She's not afraid to speak out on topics like this.
  • When we did the bake-off for the IPO she insisted all the investment banks put their diversity record at the front of the pitch deck, every single one of them that came in, and they all did.

[50:27] Conclusion

These are the five profiles that I shared with you: Bobby Knight, Bob Dylan, Danny Meyer, Sam Hinkie, and Katrina Lake.

  • I don't think a single one of them started what they're doing for money.
  • In each and every story they were chasing a passion and a dream that allowed them to study.
    • Going back to Bobby Knight saying about having the will to practice.
    • They all did it on their own.

Danny uses a phrase, "Professional research" in his book constantly, which I think is an interesting phrase because most of us think about the studying and research we do around curriculum and a teacher.

If you're in finance or marketing or accounting, do you go home at night and study to improve your own skillset? Most people don't. I think that's interesting.


  1. Pick a career about which you have immense passion
  2. Be obsessive about learning in your field
  3. Develop mentors in your field
  4. Embrace peer relationships in your field
  5. Always be gracious and pay it forward.

I stole the title of this speech from Tom Petty who, unfortunately, passed away this year.

He was once asked what advice he'd have for people if he were giving it. While it's not as ambitious as what I've told you, it's almost the exact same thing on the exact same vector.

// @blakeir