Berkeley Haas - Dean's Speaker Series | Mike Smith, MBA 98, General Partner & Co-Founder, Footwork

  • Good afternoon, everybody.

I’m Ann Harrison, I’m the Dean

of the Haas School of Business.

Welcome to today’s Dean’s Speaker Series,

which today is co-sponsored by the Berkeley Culture Center.

I’m really truly excited to introduce today’s speaker

and a Haas alum, go Bears, Mike Smith.

Mike is a proud graduate of our full-time MBA program.

He currently serves as General Partner and Co-Founder

of Footwork, an early stage venture capital firm.

Footwork was launched in April 2021 with a $175 million fund

and has since invested in eight companies.

Much of Mike’s career has been focused

on scaling consumer businesses.

Before launching Footwork, he was an early employee

at Stitch Fix and he helped grow the startup

into a public company.

He served as Stitch Fix’s President and COO all the way

from the idea to the IPO stage and beyond

where he oversaw operations, styling, client experience,

merchandise and finance.

Prior to Stitch Fix, Mike was COO at,

overseeing all operations for a $5 billion division,

including one of the most successful multichannel offerings

in the industry.

He currently serves on the boards of MillerKnoll,

Food52, Stitch Fix and Ulta Beauty.

As an alum, I’d like to also say a couple words

about how Mike has been an exemplar

of going beyond yourself.

Among a number of things, he’s hosted Haas students

for an entrepreneurship immersion visit

and for our executive education program,

he has taught a very successful new black venture VC program

in that program.

Mike, thank you so much for all that you do for Haas

and for taking the time to speak with us today.

We are really grateful to have you back on campus

and we really look forward to a lively

and informative discussion.

Today’s talk will be led by Jenny Chatman,

a well-known professor here and the Co-Director

of the Berkeley Culture Center.

(audience applauds) - Thank you.

  • Thanks, Ann.

  • Hi. - Hi.

Well, Mike, I treasure our…

I was counting how many years it is.

I think we’ve been friends for 25 years or close to it.

  • [Mike] That’s right.

  • And you were a student in my Leading People class.

  • [Mike] I was.

  • A memorable student.

  • [Mike] Well, I hope so

(audience laughs) in a good way, hopefully.

  • Yeah, in a good way.

And to complete the cycle, your wife, Kelly,

was my daughter’s fourth grade teacher.

So we have that.

We wrote a case about you based on your unbelievable work

at, like the innovative site-to-store process

which you originated and did so much to make happen,

your massive success there.

It was so successful that Walmart spun back in

and then wouldn’t let us publish the case.

So that was good and bad in how it worked out.

You’ve inspired perhaps at this point thousands

of our MBA students by coming to class

and talking to them about your career.

And most importantly, because of your focus at Stitch Fix

in men’s, my husband is now very well dressed,

which is probably the thing that I’m most thankful for.

So let me start by thanking you for your support

of the school and for conveying to you just how proud we are

of all you’ve accomplished.

And I’m thrilled to be hosting you here today.

  • Well, thank you and I will say she’s become Jenny to me,

but Professor Chatman taught me everything I think I needed

to know about leadership in your class.

And so I am grateful to be a Haas alum

and excited to be here.

  • Oh, thanks.

And of course, that’s completely not true

because with students like you,

all we try to do is try not to mess up the raw material

and that maybe happened in this case.

So we’re gonna go through and ask some questions.

I’m gonna ask some questions of Mike and then about 1:10,

we’re gonna turn it over for audience questions,

so you all will have a chance to ask some questions as well.

But let me start with a really broad question,

which is for people who don’t yet know you,

if you could lay out your career a little bit

and what the stages were

since you were a student here at Haas.

  • Sure, so I graduated from Haas in 1998 and I’d say

that the first six years of my career was really trying

to find my way in terms of my career lane

and what my calling was, so to speak.

And so I worked two years on Wall Street and then two years

at an early stage company that wasn’t in the bio,

but it’s a good story offline of failure

and actually learning a lot from said adventure.

And then worked in corporate development

at a software company.

And so claim to fame I think was nine years at

and then nine years at Stitch Fix.

And I think what I most appreciate about the journey

and the arc is just some of the leadership principles

that I felt like I learned here and certainly show up

in the leadership values of the school.

Student always I think is something I’m really…

It wasn’t codified at the time I was here, I don’t believe.

And then confidence without attitude, I think is just one

that I think is just an interesting

and important leadership principle.

And so the one thing I’d say is

that these journeys are super windey,

they are rarely up and to the right.

I joke that I literally did this at 16 years old

wrote out on a piece of paper how I was gonna go

from a 16-year-old high school student

to be a public company CEO by age 40 to 42.

I gave myself a range there.

And it just doesn’t work.

It’s just not the way these things work.

And I’m grateful that I had plenty of people

along my journey that helped me see the way.

  • Yeah, I remember you telling me that

at that diner over in San Francisco.

  • [Mike] Yep. Yeah.

(Mike laughs)

So you were COO at and instrumental

in helping Walmart become digital.

You were one of the first five employees at Stitch Fix

and in both cases, you were a primary force

in scaling up the companies. as I said was spun back in

and dramatically bolstered by the success

that you had created.

You took Stitch Fix public.

And so a broad question about what did you keep in mind

when growing talent at each company

and what lessons have you learned about talent management

and who you wanna bring on the bus with you?

  • Yeah, a few lessons.

I’d say first and foremost, there’s so many leaders

that talk about this concept of hiring better or smarter

than yourself and I think very, very few leaders do that.

I understand academically why that’s hard to do.

It requires you to be self-aware,

to know what you’re good at, what you’re not good at

and to try to hire to gaps and frankly,

hire smarter and better than you are,

which is intimidating at times.

If you’re gonna hire someone

who’s actually smarter than you

and you give them the stage,

then your boss probably wonders why you have your job.

And I do think that that was just something

that I tried to do in my career

and really think about talent that way.

I also…

It’s interesting, there’s a very good friend in the audience

who worked in my group, but I used to talk

about how I like to hire PITAs, which are pains in the arse.

And what PITAs do when you work with them

is they drive you to be a great leader.

They really demand a lot of you, they have high expectations

for themselves and who you are as a leader

and they just don’t accept not being good at the job.

And so that’s another I think philosophy

that I had hopefully is trying to hire PITAs

because it forces you to be a great leader.

And then I think there’s a lot around intentionality

around talent development that I hopefully did,

which was have these 24 vision and value statements

that I share with my direct reports

when I start working with them.

And one of them is seeking a social contract

with people I work with.

And the goal is that here’s a very tangible example

of where I never wanna be surprised

by someone leaving the company.

I don’t ever wanna get two weeks notice as an example.

And I think what’s required

to avoid that situation is really honest conversations

about what you’re doing well, what you’re not doing well,

where do you wanna go in your career

so that you can be an enabler of where they wanna go,

even if it’s not in your current company.

And so I fortunately, I’ve had one incident

where I was surprised.

So I do really believe strongly that’s a failure

of the leader when you get surprised like that.

But it’s just something I think philosophically

that I sought when working with the folks,

the wonderful folks I’ve gotten to work with over the years.

  • How do you find PITAs?

  • They find you in some ways.

I mean, I think in some ways, you get known as someone

that is really open to hiring smarter

and better than yourself.

And then they have friends, they hang out in circles

of wanting to be challenged.

And then I think you can also find them

at great business schools, a lot of Haas folks

that I’ve worked with over the years.

And they show up really early

in an interview process, they do.

Now, there’s an element of I don’t want…

If I have seven direct reports,

I don’t want everyone being challenging all at the same time

at the same rate because that is extremely difficult.

And I make it very clear where my line is

of how much PITA I will allow

in the time that we’re allowing it.

But overall, I think they’re easy to spot.

I felt like I was one, too, to be honest.

I demanded a lot of my bosses, I had high expectations

for myself and for the company and for any leader

that I got to work with.

And so I think they self-identify in a lot of ways.

  • I remember that in class, actually.

  • [Mike] Oh wow, nice!

(Mike laughs) (audience laughs)

I do, I think that’s probably true.

(Mike laughs)

  • Great, so Stitch Fix goes public

and you were there a couple more years

and then you decide to leave to start Footwork.

What were your motives for making that move?

  • Well, it was unusual, I would say,

in that if folks that knew me

had talked to me between call it 2012 and 2020

when I made the decision if I would ever work

in venture capital, let alone start my own firm,

they would’ve said, no way.

I had a very challenging relationship

with the ecosystem as we were trying

to raise money for Stitch Fix, it was very challenging.

Katrina Lake, the Founder and CEO of Stitch Fix,

has talked openly about this in different podcasts.

And it just wasn’t well received and frankly, our experience

with the ecosystem was rough, to say the least.

And so I think what end up happening in 2020,

a few things happened.

One, there was a lot of racial unrest

with the George Floyd murder and other things

that made me take pause and really think

about a little bit like legacy and impact and bigger things

and just what I wanna work on every day.

There was my partner, Nikhil Basu Trivedi, who reached out

and asked if I was interested in starting a firm with him

and I knew that I was very aligned in core values

and principles with Nikhil and very grateful

that he was even willing to chat with me about it.

And then I just, instead of…

I don’t know if this is a good analogy,

but I remember in different jobs that I’ve had

where I had challenges with a function

that I wasn’t responsible for where I was like,

why is that function not operating well?

And it’s the classic, well, if you think you know better,

why don’t you run it?

You’re in charge of it.

And I think there was an element

of I’ve had so much challenge with the ecosystem,

meaning not as many black and brown and women founders,

not as many black, brown and women check writers.

And certainly on the LP or the investor side,

finding the same case.

People that were investing in venture funds

not seeing enough underrepresented folks.

Instead of complaining about it,

why don’t you try to do something about it?

And so I think it was just this combination and cocktail

of wanting to have impact given what was going on

in the world, really loving most of the ecosystem

in terms of the founder perspective

and what innovation exists out

in the Bay Area in particular.

And then instead of just talking about it,

trying to do something different.

  • So you started the company with Nikhil

and the two of you came together

with really different backgrounds and perspectives.

Can you talk a little bit about how that’s working

and how you make a partnership like that work?

  • Yeah, we were very intentional that we wanted

to have differences in everything.

So one of our core pillars of the firm

and what we think is our differentiation,

one of the few areas of differentiation

is this operator-investor combination

being the killer combination that really helps founders

and founding teams scale themselves.

And Nikhil, for those that don’t know him,

went to Princeton, he has been an investor for 11 years.

And so he’s grown up as an investor architect

and he’s an amazing investor.

And I had never invested.

I didn’t have an angel portfolio,

I’d never been an investor.

And I think we think that those differences

actually are very, very helpful.

Nikhil is amazing at understanding product market fit

of a company and really understanding what’s required

from a metrics perspective to get to the next round.

And he’s seen so many different companies

and invested in so many different amazing companies

that have achieved amazing success,

like Farmer’s Dog and and Imperfect Foods.

And so he has seen a range of things

and I’ve been very focused on eCommerce

in and Stitch Fix.

And I do think that having seen two hypergrowth companies,

one that we called a startup at,

but the reality was just like

when you actually don’t have to raise capital,

it’s not really a startup.

Where at Stitch Fix, we actually had

to raise capital to achieve.

And so you just have different learnings

and I think experiences

that you can bring to bear as an operator.

But we’re different on lots of different dimensions,

like he’s a lot younger than I am, he went

to a fancy school I like to make fun of in Princeton.

  • [Jenny] We’re fancy.

  • Yeah, we’re fancy, true.

A little fancy here. (audience laughs)

We have different styles.

We talk about he’s pretty intense,

I’m sometimes overly chill

and we learn that when he’s really intense

and I’m really chill,

we need to work on our partnership there

and I need to come closer to him

and he needs to come closer to me.

So it is like a marriage.

You have to work at making it work.

But we are super grateful to be in business together.

We have amazing investors that put us in business

in April of last year and it’s been a blast.

And I do think some of the core pillars and differentiation

that we thought would show up in terms of how we work

with founders has been very true and we’re excited about…

Yeah, we have a lot to prove,

but it we’re excited about our start so far.

  • Yeah, so you have now seen and been part of organizations

at different stages of growth and different sizes.

So when you think about forming a culture

in a startup organization, like as you look

at a potential firm that you might invest in,

what are some of the things that you’re looking for?

  • Well, I can certainly answer the question

in a few different ways.

So first, when we look at companies, we are evaluating

whether there are signs of product market fit,

whether is it a good market for their product or service

and we evaluate the founder.

And we have these three things that we basically look for,

which is hungry and humble, know your business inside

and out and if someone is a talent magnet.

I would say trying to figure out whether

they have a good culture at the existing time

that we’re trying to make this decision is a sub-bullet

underneath how we’re evaluating the founder.

But our strategy is to lead rounds,

so we try to be the biggest check and lead either a seed

or series A investment and we take board seats.

And part of the reason we do that

is because we wanna be very active in company-building

and very active in culture definition.

And I do think, we only have eight investments,

but I think all of our companies

and founders lean on us pretty heavily

for company-building and culture.

And I like that level of accountability,

both that we can drive, but also that we’re accountable

for as fiduciaries as board members.

But in the evaluation process,

we’re mostly only spending time with the founding team

and not going as deep in the company

because these processes are super fast.

The best companies are getting from talking to investors

to signing a term sheet, it could be as fast as two weeks

or as fast as a week.

And so you don’t have as much time.

But it’s super important to us

to make sure that the companies that we back

and the founders we back care deeply about these issues

and create great cultures to work in.

And I think the board seat and just the way we work

with founders helps us have a better chance

of succeeding on that.

  • And so how would you define a great culture,

taking all your experience together?

  • Yeah, it’s a big question

that I probably don’t have a great answer for,

other than I think cultures need to be super intentional

and you actually have to work at them.

I remember at different points at Stitch Fix,

one of my favorite people, this woman, Margo Downs,

would be asked this question in our onboarding process.

And they’re like, “What’s the culture like

“and how are you going to continue to drive it?”

And she would say, “You can’t just be a consumer

“of the culture.

“You actually have to help develop the culture

“and drive accountability of the culture.”

It can’t be passive.

I don’t think cultures can be or should be passive.

I think they’re really important to be clear.

I think that’s an important part of culture.

I think one of the things that drives me crazy is

where if the senior folks don’t live and breathe

and show up as the culture as defined,

then that’s a problem.

And one of the things that I loved about Stitch Fix

in the early days is that Katrina really wanted

to develop that culture early.

So we did a culture-defining exercise

with four full-time people at the company and six interns

because that’s how much she cared

about being clear about that.

Now, what I loved about it the most was that,

okay, now we have definition of what good looks like

in terms of what our expectations are.

And what I especially loved about it

is now we have a definition of how leaders show up

and managers show up.

And you could have language

around if we weren’t showing up that way

to be able to drive better accountability

on those dimensions.

So I think I don’t have a great answer,

but I do think it’s super important.

I think you need to be intentional, I think you have

to drive accountability to make sure

that it lives up every day.

And I do think some of the more challenging companies

are the ones that allow leaders to show up different

than what the cultural norms should be

or the way they’re defined.

  • Yeah, well, and there’s actually research that shows

that startups that are intentional about their cultures,

there was actually a study done at Stanford

where when founders were intentional about culture,

faster to IPO, came out at a higher price.

There’s all kinds of financial gains as a result of that.

So that dovetails closely with what you’re saying.

  • [Mike] No tough ones.

  • Well, you’ve answered a bunch of them,

so I have to skip down here.

Ah, so you’ve mentioned in the past

that Footwork is interested in investing

in firms led by people of color and women,

perhaps people who have been less represented

in the business community.

Why is it important to you

to prioritize diversity in business?

  • I think fundamentally, Nikhil and I believe

the academic work that diverse teams drive better outcomes.

And he is a British Indian immigrant, I’m African American.

Diversity across every dimension is one of the core pillars.

Diversity across every dimension

being a competitive advantage is one of our core principles

of the firm’s founding.

We do not have inputs

to saying we only wanna back underrepresented founders.

We do expect based on our core pillars

and the way we look for founders that the output is

that we have a very diverse portfolio.

And that has been true.

The N is super small, so it’s not statistically significant

with eight portfolio companies.

But we’re proud of the fact that the majority

of our investments are led by people of color or women.

So we wanted to be the output, but I think it just comes

from just truly believing what we’ve seen in operating,

what he’s seen in investing,

that diverse teams produce better results.

And we understand some of the challenges that diverse teams

as I think I learned in your class, too,

sometimes you have to move slower

because you wanna take everyone’s point of view,

but that driving, hearing all these different perspectives,

especially in the world we’re in today and trying to get

to best product, best service, you really do need to think

about more perspectives than just one narrow either gender

or race perspective to get to the best ideas.

And so we just believe that in our core.

We started the firm with that belief and the output

of our investments so far have lived up to that.

  • I didn’t hear anything

after he said he learned that in my class.

  • I know, I know. (Jenny laughs)

(Mike laughs) (audience laughs)

I did, though.

  • Thank you for that. - You’re welcome.

  • Thank you. - I heard it all actually.

It was accurate, you would’ve gotten an A.

  • Thank you. (audience laughs)

I don’t think I got an A in your class, though.

I think I gotta go back and look.

  • I think it was an A-minus.

  • Okay, that’s what I thought, too.

  • I’m sorry, is there a HIPAA rule on that?

  • I don’t think there is, I don’t know.

I’m okay with that.

I just granted it to you, so it’s all good.

  • And it was before we had codified,

questioned the status quo and just on that point,

we cultivate questioning the status quo not just

among our students, but among the faculty

and among the staff.

And I gotta tell you, it’s exhausting.

It is exhausting.

People are constantly looking for better ways

of doing things and they’re pushing ideas,

but it’s totally worth it.

It’s the way that you get the cutting edge ideas

and the best innovation.

  • It is, but I do think you also have draw lines and say…

One of the phrases that probably was not the most…

It was a tough phrase, like, hey, we gotta just do our jobs.

I’m done talking about stuff,

we actually need to get it done.

And so you have to allow collaboration and different points

of view and challenge the status quo,

but if you spend all your time challenging the status quo,

it’s really hard to get things done and execute.

And in the fast-moving world of today,

you actually have to make a decision and move forward.

Happiness is not what…

Collective happiness I think is hard to achieve.

You actually need to, if you’re gonna allow diverse opinions

and allow challenge, there are gonna be people

that don’t love the final decision that you make.

But I think what’s unacceptable is not having voices heard.

And so I’ve hopefully tried to emulate allowing voices

to be heard and different points of view, but ultimately,

we make a decision and we have to go.

  • Yeah, I’m gonna deviate just slightly

and ask you if you’d be willing to share

when you’ve come to some of my classes,

you’ve talked to students about some

of the failure experiences that you had.

And I remember you coining the term, pity city.

You can go to pity city, but you can’t stay there very long.

I thought that was so helpful as a metaphor.

For our students who are pushing through careers

that are unlikely to be linear,

how do you have the resilience to move to the next step

and absorb the disappointments?

I don’t know if you can give an example

and talk about how you dealt with it.

  • Sure, and I think it changes.

I think the more experience you have with failure,

the more resilient you obviously get.

And you can then go back and be like, it wasn’t that bad

when I worked at a digital smell company

in the dot com bust and my boss at the next job,

every time I see him, he’s like,

“Smell-O-Vision, it’s Mike Smith from Smell-O-Vision!”

(Jenny laughs) (audience laughs)

You have to be okay with that and fail.

And I think you learn that you don’t have to…

Not only is pity city not that bad,

you can learn a lot from those failures.

So a couple things, one, that phrase,

I wrote about it recently in LinkedIn

and it had some ridiculous amount of impressions

from telling this story about getting passed over

for the CEO job at,

but I should give credit to where credit is due.

Marka Hansen, the former President of Gap North America,

talked about that and she’s a long-time mentor of mine

and basically said, “You can go to pity city,

“but you can’t take up residence there.”

You actually have to get over the tough thing.

So the two very tangible examples for me were going

to an early stage company, leaving Morgan Stanley,

going to an early stage company,

basically telling my parents I was leaving

this big great Wall Street job and go into this company

that was producing, creating a box

that would produce smells.

My parents thought I was, as they should, cuckoo crazy,

like, what are you doing?

You went to business school to get this fancy job

and then you’re gonna go do that.

And it was a complete failure.

It didn’t work.

It was product market fit problems,

we had culture challenges.

There were a lot of things that just didn’t work

about unfortunately the idea.

And it’s hard to get a job after you’ve worked in that.

Now, I think this is an area of the world,

it’s very special.

There’s no badge of honor that comes with it,

but there are lots of…

I think with innovation comes an okay with failing

and moving forward and the common, fail fast, fail forward.

And I was fortunate enough that I had a good network

from Haas and allowed me to get back on my feet

and get a great job the next time.

And the other one was the one I wrote about,

which is feeling like I was preparing myself

for being CEO of,

being told I was gonna become the MC at

and then not getting that job was extremely painful.

It was so hard.

But no one’s gonna feel sorry for me to go to Stitch Fix

and be employee number five

and be a really senior person there and helping build that

with Katrina and an amazing team from five people

to 10,000 people and going public in 2017,

and so all the good fortunes that have come as a result

of that experience.

And so I think it’s just a little bit of understanding

that it really is okay that it’s not linear.

I think that was hard for me in the first decade

of my career.

I just, because I had written down

exactly what jobs I was gonna have from 16 to 40 to 42,

some deviation of that was hard for me

to be like, oh, this isn’t working.

And then I think the other big learning for me was

being again fortunate to have amazing people around me

that knew me at the core, knew what I wanted

and actually supported helping me find things

that were amazing.

The reason I got the job at

is because I think four of the first 15 people

at are Haas grads, three in my cohort here.

And they were like,

hey, I know he doesn’t have retail experience,

but he’s great.

And I know he doesn’t have ops experience, but he’s amazing.

And they helped me get the job.

And it’s because of cultivating that network,

but also having people that would stick their neck out,

frankly, to help support me get to the next job.

  • And I hope you all will continue

to promote your colleagues as well.

So I wanted to come back to the theme

of diversity and inclusiveness,

which seem to be core values of Footworks.

What is your position on…

I think organizations are really struggling

to figure out how to create inclusive environments.

I think there is more certainty out there

that this is a good thing, but I think there’s still a gap

in actually being able to put it into practice.

So what are some insights that you have

about inclusiveness in particular

once people have joined organizations

or setting up your entrepreneurs in a network

that enables them to be successful,

how do you make things like that happen?

  • Yeah, I’d probably go to more of a bottoms-up answer to it

of giving tangible examples

of where I’ve seen companies do it well

and companies and leaders that don’t do as well.

I mean, there’s the old adage that you have two ears

and one mouth and you should use them proportionately.

And I believe that that adage

really helps drive inclusivity.

  • [Jenny] What was that, two years?

  • Two ears and one mouth

and you should use them proportionately,

just listen more than talk.

And I think if you organically people listen,

if they listen more than they talk,

it allows for more voices to be heard

and you seek out other people’s opinions

because you want to learn from them

or you feel like they have something valuable to share.

And so I look for teams and in my own operating model,

how much am I talking versus listening

and making sure that voices are heard?

This is again a very minute example, but in the world

of Zoom, if someone comes off mute but I’m talking

and I’m talking, I’m talking and someone comes off mute,

I wanna make sure that that person

actually gets their voice heard.

So many times, I just watch it.

Someone comes off mute and the person just keeps talking

and you never go back to the person that came off mute

to figure out what their perspective is.

I was in a board meeting three weeks ago

where I was getting ready to say something

and someone jumped ahead.

It wasn’t malice, it wasn’t poor intentions,

but the CEO asked later,

“Hey, Mike, did you have a point that you wanted to raise?”

That felt super inclusive to me.

I don’t think that happens most of the time.

I think people just move on.

And so I think being observant and listening

and calling on people when you feel like

they have something really important to say

‘cause you’ve heard it in a one-on-one

that you’ve had with them or you’ve heard it

in another meeting and you think they have a perspective

that’ll really help, even if they’re more junior

or they’re shy or whatever.

You don’t wanna make them uncomfortable, but you definitely,

if you know that they have a point of view

that would really advance the conversation,

just ask for them to share it.

And I think very few people do that effectively.

And I’m not trying to pretend

that I do it great all the time either,

but I do think if you have a belief

that you want the right people around the table,

you want diverse opinions, you want to hear about those,

then your behavior should match including those voices

and your actions should show that, too.

  • Well, and that’s a very cultural way

of thinking about inclusiveness,

which seems like this big huge challenge,

but you’re breaking it down into the behavioral norms

that you wanna put in place

so that people regularly are listening to each other

and circling back and the rest of it, super helpful.

Okay, so we’re close to our time.

Last time question from me is what advice do you have

for our students who are gonna be graduating

in the next year or two?

What are some of the kernels

of expertise you wanna offer to them?

It’s a daunting question.

  • It is a daunting question because I remember when I sat

in that seat, I definitely had a little bit of judgment

about people like me answering that question.

Like, yeah, whatever.

Do you know how hard my life is

and you think you’ve done all these great things–

  • [Jenny] How old is that guy anyway?

  • Yeah, I was a PITA in your class, remember?

So yeah, exactly. (Jenny laughs)

I think there’s probably two things that I would share.

One, I touched on.

One is I did not buy into this from 22 to mid-30s,

but this idea that your career isn’t linear

and that you should embrace the zigzags

and you should be willing to take a lateral job

in the same company to learn something new and different,

that you should be intentional about getting skill sets

that will really help you be better at the next job,

even if it feels like it’s less money

or less prestige or all of that stuff.

It’s really hard.

I didn’t do a great job of it from 22

to like I said mid-30s.

But I think if you just at your core recognize

that it’s not linear.

You talk to any successful person, not that I’m one,

but if you talk to any successful person

and almost none of them have that 16-year-old

to 40 to 42 promotion every two years career.

That’s just not the way they work.

And so the earlier you recognize that,

I think the better off you will be

and the less crazy you’ll drive yourself.

That’s one piece of advice.

The second that I can’t even tell you

how beneficial mentoring has been to me.

And I’d say it was sideways, up and down.

I would say that I mentor a lot of people

and I do learn as much from the people I mentor as I do

from the people that mentor me.

One thing that’s very underappreciated is peer mentoring.

And I talk about it any chance I get,

which is having someone that’s around the same level,

not in the same group as you that you trust enough

where you share, hey, this is what I’m good at

and here’s where I have areas of improvement

from my performance review and from what you’ve seen.

And they are so committed to you and your career

that when they’re seeing you in these forums on the things

that you’re not particularly good at, they pull you aside

after the meeting and say, hey, you weren’t great again.

They are not shy about giving you feedback on what needs

to be better and giving you specific insights

to what you could’ve done differently in that situation.

And so I’ve been a major benefactor of peer mentors

that cared so deeply about my career that they just wanted

to make sure that recent feedback after performance,

good or bad, that they gave me feedback.

And then obviously more senior mentors

that are a little bit further in their career,

but again, you have to have trust

and vulnerability with them,

I have been a huge, again, benefactor of.

And I think that one thing that I would offer

is be really surgical is the word I’d use

on terms of mentors

because I think too often people pick mentors based on title

or you wanna go into investing banking,

they’re an investment banker.

That is too narrow a way to pick a mentor.

Really evaluate what you’re good at,

what you’re not good at, seek out those

that are better at the things you’re not good at

and it has to be someone that you can build trust with.

It can’t be someone that you can’t talk about the things

that aren’t working for you.

It can’t be this transactional relationship.

It needs to be a super human, very vulnerable relationship.

And I have been extremely lucky that I have four

or five folks in my network that even today if I call

or text them today, today, they will call me back

this afternoon and be willing to talk,

regardless of where they are.

I remember one of my mentors, Carter Cast, who teaches

at Kellogg, and I think I texted him,

hey, Carter, I’d love to talk in the next couple of days.

And he was literally on the road, some major highway

with his family and yes, he asked his family for permission

if he could call me, but he wanted to make sure

that he met the need ‘cause he felt my urgency.

And I’m just lucky that I have those kinds of folks

in my life that are really willing to work.

I have to work at it and he’s gotta be willing.

But I’d say having great mentors, being a great mentor

to people, having peer mentors

and then having more senior mentors

that you’re really thoughtful that you can build trust with

is the last piece of advice I’d give.

  • Well, that’s fabulous, fabulous advice.

So we have time for some question for Mike.

It looks like we have a microphone set up there

if you wanna step up to the microphone and ask a question.


  • [Ellen] Hello. - Hi.

  • Hi, thanks, Mike, this is awesome.

  • [Jenny] Do you wanna introduce yourself?

  • Oh sure, yeah, my name’s Ellen Quigg, she/hers.

My question is about I think the advice about zigzagging

and being comfortable going linearly, not linearly, sideways

in your career is great advice

and I’m curious if you would talk a little bit

about specific times you made that decision

and what you did and what you feel like you got out

of what you did there?

  • It’s a very good question, thank you for asking.

So at Stitch Fix, I was Chief Operating Officer

and I was lucky enough based on the success of the company

and wanting to be on boards that I was starting

to get some public and private board offers.

And then I decided to talk to Katrina, my boss,

about a job I really wanted at Stitch Fix,

which was to launch our men’s business.

  • Yay! (Jenny applauds)

  • Yay, Russell! (Jenny laughs)

And the title was gonna be General Manager of Men’s.

So it was not a C-level title.

It was to help me get better at merchandising

because ultimately I wanted to be a CEO

and I had never done a demand gen job,

meaning I’d never worked in merchandising or marketing.

And I said I wanna do it.

Now, the reason I bring up the public

and private boards is I was in a process with a public board

and they said, the recruiter, “Why did you do that?”

And I said, ‘cause I wanna learn this.

They said, ‘You’re out of the process.”

I said, why?

They said, “Because you’re not a C-level exec anymore.”

I said, well, I still report to Katrina

and I’m on the senior team.

“Nope, it’s the COO title is why we liked you

“for this role.”

And so I knew that I was taking some risk in it.

That one was one that I had not predicted

that I’d not be able to get on a public company board,

but great, I would do that all day long

because it just broadened my skill set

and it made me I think a better president

when I got the role and was overseeing all of merchandising

because I’d helped with a team build that up.

And so I think some of that move was lucky, not intentional,

but I never thought about moves like that

as anything other than learning.

And so I had this very simple framework

up until I think I was managing a lot more people

of learning and people.

So am I gonna learn a lot and am I gonna work with a tribe

and the people that I wanna work with

and are those people who are gonna push me?

And then when I became a manager, I added impact.

So it was learning, people and impact.

And that’s still how I make decisions very simply.

But title, comp, those things, I tried not to have

as strong a vector in terms of how I made decisions.

So but that one, yeah, it’s good learning,

bad for public company boards.

  • Thanks, please.

  • Hi, my name’s Carissa, I’m an undergrad student.

I wanted to thank you first for coming out.

  • [Mike] Sure.

  • So I saw on the news that they’re thinking

of removing affirmative action at schools like UNC,

but this more so begs the question of I guess equality

in terms of opportunity.

So for your VC, when you’re thinking of people

that you wanna support, how do you balance the idea

of them not particularly having the resources

versus not working as hard?

So how do you make that differentiation?

  • Well, if I understand the question, I don’t differentiate.

I look for people that are going to work very hard

and might have come from places

where they didn’t have as many resources as I did

or other people did.

And I don’t think they’re mutually exclusive.

I think you can find amazing people

that come from different backgrounds

that will do amazing work in venture

or in an operating job or what have you.

And so I think one of the things that people,

especially I’d just say as a black man,

I have to be excellent every day.

I feel that burden and I’m happy to have that burden,

feel it all the time because I just recognize, look,

if I don’t make use of venture, if I don’t make it

in venture, then it messes up the whole…

Not the whole, it’s not like I’m the only black person

in venture, but there’s not that many of us.

Then people start to question

why should we have a diverse team,

why should we support diverse or more emerging managers?

And so I think it’s just important to be excellent

and seek people that see that as the guiding principle

of who they are, whether it’s in venture

or in an operating company.

  • Can I rephrase the question?

  • [Mike] Sure, yeah, yeah, if I missed it.

  • It’s more so like those that don’t have the resources,

those who are at San Jose State University

and aren’t really surrounded by opportunities like this

to see what’s out there.

How do you make sure that they get equipped

to be able to have opportunities like that?

  • Well, I think there are a lot.

I think, using venture capital as an example,

I think it’s becoming less and less en vogue to only recruit

and only seek founders from fancy traditional schools.

I think there are so many people

that come from all these different places.

And so it’s incumbent upon us as investors

to go find the best founders from across a spectrum

of where they go to school.

I think when I first graduated from Haas,

I would meet venture capitalists, as an example,

that would only invest in Northern California.

They didn’t invest in…

It was a great founder in Ohio,

they didn’t spend any time there ‘cause what they said

is they didn’t wanna get on a plane and go to Ohio.

But I think that is being very much put to pass

because you see amazing companies

being built all over the place.

And you see amazing founders starting companies everywhere.

But I do think it requires the industry,

whether it’s, again, a company or the business ecosystem

or a venture to be actively looking

for those opportunities outside of their little pool.

  • [Carissa] Thank you.

  • Sure. - Thanks.

  • Hi, Mike. - Hi.

My name’s Aria, I’m a senior at Haas.

So I’m curious,

you’ve been in so many different environments

specifically within the corporate world

and then now you’re in VC.

What advice do you have for us, we’re about to go

into the workforce, about to go into the corporate world

in terms of navigating the corporate environment

and succeeding?

  • I think and I didn’t learn this, it took me a little bit

to learn this, too, but I think one major piece of advice

that I’d give you is understanding how

to know the difference between not performing well

at your job, performing well at your job

and performing exceptionally at your job and being clear

in defining that with your boss.

The reason that matters is because I always wanted to,

and it took me awhile to figure this out,

have very objective conversations about how I was doing

or whether I should get promoted

or whether I should make more money.

And the only way to try to get it as objective as possible

is to try to define what exceptional looks like upfront

or try to define where I’m not performing upfront,

so that I’m not surprised.

I can always tell my boss that,

yeah, I didn’t have a good day.

I didn’t have a good day.

And so I would say trying to have that conversation early

in your career and hopefully find leaders that you work for

that are aligned to that definition and trying to get

to objectivity was something I would advise you to do

‘cause then it becomes really simple.

There’s less emotion I think that goes

with the tougher conversations around promotion

and compensation if you define some of that stuff upfront.

  • [Aria] Thank you very much,

appreciate it. - You’re welcome.

  • Thanks, other questions?

Please, yeah.

  • [Melissa] My name’s Melissa.

I’m in the full-time program.

I was curious because you talked about–

  • [Assistant] Could you go the microphone

‘cause we’re streaming.

  • Yeah, we have a huge audience.

  • Hi, my name’s Melissa, I’m in the full-time MBA program.

I was curious what you’re most excited about learning

about next given that you have come into roles not because

of the title or the compensation,

but because of the learning?

  • Yeah, for me, venture capital just as an industry

is amazing for that question.

What am I most excited about next?

I am excited about learning

what climate solutions might exist

to help the climate challenge that we’re in today.

I’m super excited about learning about healthcare.

I’ve never operated in healthcare.

I’ve been a consumer of healthcare,

but I’ve never worked in anything in healthcare.

But we have a bias to doing something in healthcare

at Footwork and I’m excited to learn about that.

So honestly, it feels like every day scratches that itch

of what I’m most excited about.

And I think the biggest challenge I have is trying

to narrow all the excitement that I have

for all the different opportunities that you can invest in,

rather than broaden it.

I mean, it literally is every day,

I’m learning about something new.

And so for people that are lifelong learners

or students always, it’s a perfect job honestly for that.

  • [Melissa] Thank you.

  • Sure. - Thank you.

  • Hi, my name’s Kira.

I’m doing part of my master’s degree here at Haas,

over from Europe actually.

And following onto that question,

I wanted to ask how do you learn?

What do you do to learn about new topics,

what are your methods, who do you talk to,

how do you go about it?

  • Yeah, I’m less of a reading learner

and more of an experience learner and asking questions

and having people in the ecosystem.

So if I wanna learn about…

One of the things Nikhil and I have thesis areas,

I’m starting to learn about aging ‘cause I wanna see

if there are investment opportunities there.

And so my parents are aging and my wife’s mom is aging

and I talk to other investors that are in aging just

to understand why they invested in the space broadly

and what are the challenges.

I think for me, I’m a much better experiential learner

and listening learner than I am reading white paper learner.

And so I think clearly understanding your best mode

of learning as quickly and efficiently as you can

is important, especially in this job.

But that’s how I do is just ask a lot of questions of people

that have been in and around the space for awhile.

And I try to do that and if someone’s trying

to learn about eCommerce or operations

and they’re an experience learner, sharing perspectives

that I’ve had from having done it for awhile.

But that’s my best mode of learning.

  • So are these your folks who–

  • Well, so, yeah, there’s some.

Johnny, you have to raise your hand now.

  • Yeah, do you have some stories, John?

  • [John] Oh, I have lots.

(Mike laughs) (Jenny laughs)

  • Well, John, especially John had the unfortunate,

but we drove to together for a number of years.

So not only did we work in the same division,

we had long commutes down.

  • That was a long drive, down by SFO.

  • Yeah, together in our…

I said our Prius because we basically shared,

co-owned this Prius together

that we got to spend time together.

But I think when we stopped commuting, I thought we signed

in blood that you couldn’t tell any stories about me.

  • What was said in the Prius stays in the Prius.

  • What’s said in the Prius,

stays in the Prius, that’s right.

  • Good, well, listen, Mike, every time we get together,

I learn so much from you.

You are a really deliberate organized thinker

about everything important.

And it’s such a gift to have you in my ecosystem.

And I think you offered great insights for our students

and colleagues who came to visit today,

here and in the ether.

So I just wanna thank you.

I think Mike’s gonna stay around for a little bit

if you have follow-up questions,

but thank you for coming back to Haas.

  • Well, I have to say thank you.

I live five minutes from here,

it’s because I love the ecosystem so much and super grateful

for you being my professor and you inviting me to class

and getting to stay a part

of this amazing ecosystem at BerkeleyHaas.

And just like, again, the leadership principles

that I think helped shape me

and hopefully hold me accountable

to continuing to be a good steward out there.

So thank you.

  • You make us so proud, I’ll just say it again.

So thanks to Mike Smith.

(audience applauds)

  • [Mike] Thanks. (audience applauds)

Thank you. - Nicely done.

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