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November 1, 2023 33 mins

Alexa von Tobel, Founder of LearnVest & Inspired Capital: Lean In … to the Pain!

 

Alexa quit her Harvard MBA to build financial planning software during the banking crisis. Six years later, she sold it for $400M and is now investing in the next generation of entrepreneurs—in more ways than one. Alexa and Mike riff on raising money, embracing AI, personal investing, and staying on that grind. Plus: 

 

🎙️ Should you get a coach?  

 

🎙️ What kind of leader do investors want to back? 

 

🎙️ Success vs happiness vs joy.

 

🎙️ The 50/30/20 rule of personal financial planning.

 

🎙️ And the one big secret of work life balance.

 

Prepare to be inspired this week!

 

You can listen and subscribe wherever you get your podcasts. https://lnkd.in/ephV67C8

 

Go Deeper:

 

📚 Alexa’s latest book, Financially Fearless:https://www.amazon.com/Financially-Fearless-LearnVest-Program-Control/dp/0385347618

 

🎧 Inc. Founders Project with Alexa von Toble: https://www.iheart.com/podcast/256-inc-founders-project-with-31156625/

 

💪 Mike's full reading list, The Career Manifesto, and other resources here: www.mikesteib.com

See omnystudio.com/listener for privacy information.

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:06):
Welcome to the Office hours, where we sit down with
the chief executive shaping the world and answer your most
pressing questions about leadership, career, and life. I'm Mike Steibe.
I'm a three time CEO and author with a passion
for learning from the best in the world and sharing
those insights with you. Today, I'm overjoyed and welcome an entrepreneur,
chief executive, and investor that I hold in the highest regard.

(00:28):
Alexavon Tobel was the founder and CEO of LearnVest, a
beloved personal finance software platform that she successfully sold in
twenty fifteen. Today, she's the founder and managing partner of
Inspired Capital, a five hundred million dollar early stage venture
capital fund. She's written two best selling books, been recognized
as a Forbes thirty Under thirty and forty under forty leader,

(00:49):
and is the host of the Wonderful Inc. Founder's podcast
with Alexavon Tobele Alexa, I've been looking forward to this.
I'm so glad you're here.

Speaker 2 (01:02):
Thanks Mike. Mike, that was such an efficient bio. I'm
like you had impressive Thank you.

Speaker 1 (01:08):
You know, we try to keep the pod to thirty
minutes because the average commute in America is thirty minutes long,
so we want to get you in and we're going
to get you out.

Speaker 2 (01:15):
You're amazing, all right.

Speaker 1 (01:17):
So you know, we've got questions from the audience on
the joys and pains of growing a new business. We've
got some questions coming in this week on the experience
of pitching investors and being pitched, and how to think
about personal finances and even personal happiness. The first one
is from Haruki in San Francisco, who says, Hi.

Speaker 3 (01:35):
I'm always inspired by entrepreneurial journeys. Can you tell me
the ardent stories of how your companies are founded? And
also I would like to know when did you know
you how to fix that?

Speaker 1 (01:46):
Alexa, the learn best story is really inspiring. I know
you were in business school. It's the moment of the
financial crisis, and you dropped out anyway and started your
company to bring your vision to life. Tell us about it.

Speaker 2 (01:59):
So I'll serve just the basics, which is I became deeply,
deeply infected by this mission that I actually still carry
today around the fact that we all go through our
education system and I'd gone to great schools, Harvard undergrad
and Harvard business school never had a minute of education
around how to manage my finances. Yet every single day,

(02:20):
every person on the planet has to manage their money
in order to be able to exist, and it's not optional.
And I kind of felt like that was wrong. I
felt like the fact that we weren't set up and
setting the world up for success on that topic and
just felt like a injustice. So it was under my skin, Mike.
I was twenty two years old. I'd started thinking about

(02:41):
this idea my senior year of college, and it just
stuck with me, and finally I just started getting it
out on paper. I started writing a business plan. It
was roughly seventy five pages. It was gobbledgook, but I
just got it all out of my brain. And the
more I thought about it, the more convinced I was
that something needed to exist and learn best stood for
learn or invest. May of two thousand and seven incorporated it.

(03:04):
Actually my father in law incorporated it. That my boyfriend's dad,
who's down My father in law was a lawyer who
helped incorporate it. And I had gotten into Harvard Business
School and I had to go because I had already
deferred so many years, and so I enrolled and I
was on an elliptical machine when Lehman Brothers went under
and a bunch of people started calling me terrified about

(03:24):
their financial life, being like I just got laid off,
How I can't even pay my rent? What do I do?
And I said to myself, this can to impact everybody,
and when the world saying you have to zag and
this is the best time to launch it, So I
dropped out of HBS.

Speaker 1 (03:37):
That was the moment. You're in the middle of an MBA,
We're in the middle of a financial crisis, and you
were like, now's my moment.

Speaker 2 (03:42):
I felt nuts. Everyone thought I was a little nuts.
To be honest, it was not popular or cool, but
I've always been comfortable doing unpopular things, and I was
really convinced that this is my passion and I started
to invest in the I dropped out December eighteenth of
two thousand and eight, got some capital the following summer,

(04:06):
launched it tech Crunch September fifteenth of two thousand and nine,
signed up our first users January first of twenty.

Speaker 1 (04:12):
Ten, and you had millions of customers and hundreds of employees.
What an amazing American journey you had with this business.

Speaker 2 (04:21):
Thanks. He sold on a Wednesday to Northwestern Mutual and
had my first child that weekend. I'm like, nothing, nothing
has been boring.

Speaker 1 (04:32):
The joy of the exit induced to labor exactly.

Speaker 2 (04:35):
Literally, No, it is just a wild journey and Northwest.

Speaker 1 (04:39):
So then you went in house at Northwestern, which is
if there's an opposite of a startup, it's probably it's
probably that. What was that like for you?

Speaker 2 (04:47):
That's a great question, Mike. The CEO, his name is
John Schlivsky, is like a visionary guy, really really really
visionary guy. And that Moore got to know him, the
more I was so impressed with who he is and
his character. Northwestern Regial is one of the large just
insurance companies in the world. It's one hundred and sixty
five maybe now one hundred and sixty seven years old,
does about forty billion dollars of revenue each year. And

(05:09):
he literally asked me, he said, why don't let's do
a merger. And I was like, a merger.

Speaker 1 (05:15):
You're doing forty.

Speaker 2 (05:16):
To fifty few about two hundred employees here in New
York running a startup, and he was like, no, no,
let's merge them. Let's take your culture and he was.

Speaker 4 (05:28):
It was.

Speaker 2 (05:29):
It was a brilliant idea and we had the he said,
bed the same shared values you believe in empowering every
day people around the wallet. He's like, that is the
core pillar North Carsian Mutual and has been for one
hundred and sixty seven years. And I ended up joining
the team. I became chief digital Officer and we pulled
the software into the mothership and you know, millions of

(05:49):
people a year now get access to a financial plan
because of it. And it was just it was one
of the most important learning periods in my whole life.

Speaker 1 (05:58):
And it really did. The software really did become part
of the parent company.

Speaker 2 (06:02):
Our whole platform became the parent platform, and we retired
the learn Best brand and it literally is the core
of the software for north Rush Retial. It was it
was cool in the reary mirror. Is a beautiful acquisition.

Speaker 1 (06:17):
Oh that is great? And then you got a beautiful
baby like two days.

Speaker 2 (06:20):
Later, literally two days later.

Speaker 4 (06:22):
Life.

Speaker 1 (06:23):
You know, I'm going to go to our next question,
which gets a little bit deeper into the experience as
Rachel and Seattle who called this.

Speaker 5 (06:29):
One in I'm in my twenties and stepping into our
family business what are the challenges of running a business
at a relatively young age.

Speaker 1 (06:37):
So you were you were fresh out of a couple
of years of work experience, and you had half of
an MBA. What was it like to now be responsible
for this this this product and bringing this vision to life?

Speaker 2 (06:50):
Mike, I was so clueless. I mean, in some ways
it was a real benefit, right I was twenty two
to twenty three. You know, I looked back. It's funny,
I'm in my thirties now and I look back in
my twenties and I'm like, God, I was clueless, like
I had. You know, I've always been the same level
of ambition and energy and vision and passion. I mean

(07:11):
I think that niebte of just hustle and work hard
and figure things out. And I've always had this confidence
in my ability to figure things out. That's sort of
like a pillar of trust that I've always had. But
I look back at what idiot I was about so
many things where just you know, like learning through fire,
learning through figuring things out. And the one thing that

(07:32):
I think Goodness was smart enough to do was I've
always surrounded myself with people that are really really really
smart and just trusted them. I'm a very trusting person,
and I think that one. You know, I had a
lot to grow. So there were tons of things I
was terrible at, and Mike, I can tell you all
the executive coaches I hired for myself and all the many,
many battery of tests that I was like, oh wow,

(07:54):
I'm bad at that, and I'm.

Speaker 1 (07:55):
The coaches work. Do you recommend an executive coach?

Speaker 2 (07:59):
Absolutely?

Speaker 1 (08:00):
I do, oh good.

Speaker 2 (08:01):
And I was really young, so maybe that's why I
had such a great experience. But I'd always been an athlete, Mike,
and I always had coaches make me better. And my
whole life, I've had really great coaches who told me
how to get better. And I think for me, I
just said to myself, why would I be a great CEO?
I've never done this before. I'm a good leader. I've

(08:22):
been a good leader in my life, but I've never
been a CEO. How do I become a founder? To
becoming a CEO? This is probably higher coach. And I'll
never forget just the day my coach was like, you,
I need to interview everybody. And I was like, you're
going to interview everyone around me? And he's like, yeah,
I got to figure out what you're bad at.

Speaker 6 (08:38):
And I was like, wait, but why I can just
tell you what I'm bad at? And he's like, no,
I need to figure out what are your blood spots?
And I was like, why did I do this to myself?
And I remember just letting go that night. I was like,
trust the process, Alexa.

Speaker 2 (08:54):
If you really want to get good, you have to
and I now bring into this ttp lean into the vein.
You got to lean in to the tough feed back
if you want to become excellent at things.

Speaker 1 (09:02):
And you know, I mean you noted for our new
friend Rachel and Seattle that sort of you look back
on your twenties and you were an idiot, then I
would personally just add to it. Whenever I look back
two or three years, I was an idiot then, including now,
which always stresses me out because it means in two
or three years, I'm going to look back and I'm
going to be an idiot today. I just don't know

(09:23):
what I'm an idiot about. So your experience with using
coaches and three sixty feedback and hearing from others what
they may be seeing and not you, I've pretty consistently
found is a helpful check on your you know, the
confidence you bring to work every day and the things
you believe you can do. It's good to be reminded
from others what you might be getting wrong, so you're

(09:43):
not always finding out the hard way.

Speaker 2 (09:45):
Yeah, that's right, That's exactly right.

Speaker 1 (09:47):
I'd love to hear from you, because the other thing
that I have found hard about running businesses at a
younger age is it's also the moment in your life
when you often have a younger family and you've got
three kids and you've done all of this through also
the probably the hardest part of the parenting journey. I know,
I've had a very similar experience. Anything you'd observe there

(10:08):
that you'd share at the audience.

Speaker 2 (10:09):
I don't know. It's funny, Mike, I've had I don't know,
hundreds of people asked me publicly on you know, podcasts
and TV and you know, work life balance, what's this?
What's the key? And I always would rattle off some
silly like organization feature like I do this and that,
and a few years ago it like struck me like lightning.

(10:30):
I was like, the way it works is that I
love my job. That's it. I think the key to
work life balance is you have to truly, truly love
what you do. You have to love it so much
that when you have to wake up early to do things,
when you're going to sleep way later than you want
to because you have to do something, when you're juggling

(10:50):
not being able to be with your kids and they
are crying and want you. You have to love your job.
And I think the key to life is actually the really,
really genuinely love what you do. And for me, you know,
building inspired, you know, being an entrepreneur and building an
adventure fund that I wish existed for me, I take
that job so incredibly seriously. And we want to back

(11:11):
the best founders of the next you know, thirty years,
and we want to be the world's best teammates to
them and follow through on our promises. And I think
and to take that very very seriously it keeps you
going really do it every day of my life. This
is like the job that I am best serve to do,
and I love it well.

Speaker 1 (11:30):
I feel like this is the conversation I'm always having
with my my peers and my colleagues. And we had
we had Antuli sued on the podcast a couple of
weeks ago, she had a baby, took her company Vimeo public,
and then had a baby. And one thing that she
and I both like really agreed on is you can't
do any of the extra stuff like we don't do
like holiday cards and bake the nice cupcakes for the

(11:50):
drop off of the school and stuff. Something's got to
give when you have this much passion for your work
and your family, and it's good, it's it's the extracurricular stuff.

Speaker 2 (11:59):
I joke, no hobbies. I'm like, I'm a mom and
I'm an investor, and there's no space for anything else.
And it's messy. Don't get you wrong, there's like tons
of times we're just very messy. And I think my
husband and I just went into this knowing he also
runs a venture fund with a few other people, and
we kind of went into this knowing it's going to

(12:19):
be complicated, but we're complete teammates to each other, and
we prioritize our kids and our famiers's.

Speaker 1 (12:25):
Great, it's inspiring. The next question that came in is
in a similar thread, but starts to sort of get
to what we're seeing in the industry now. It's Molly

(12:45):
in Boston, who said nice.

Speaker 4 (12:47):
The company where I work was hiring and spending money
with abandon and all of a sudden has been cutting
costs and jobs and things just seem a lot harder. Now.

Speaker 5 (12:58):
Is this the norm? Or I am the wrong company?

Speaker 1 (13:02):
So you've been in the role when things are hard
and you're investing in businesses and I've done the same.
What's your read right now? What do you think is
going on for Molly in Boston?

Speaker 2 (13:12):
Great question, Molly. Unfortunately, every company in the country is
going to be cutting costs. We're just we're not through it.
We're not done with it, cutting costs, laying people off.
We're still working through the indigestion of the blasts, you know,
eight years and you know, the real flag should be
when a company is spending money with reckless abandon. That

(13:33):
should be when you're nervous. You want to work for
really very prudent people who are very thoughtful with money.
Those are the people, you know. The best CEOs, Molly
are capital allocators. They're very very good about allocating the
capital of the company because they are investors. They are
investing in the parts of the business that will make
money in return money. So when you feel like you're

(13:56):
working at a company where they're spending with any level
of less abandonment. That's a real problem. And you're not alone.
Every company in the country is cutting costs, every single one.
That's how interest rates work. Literally, interest rates go up.
The FED is cooling off the economy. What that means
is every CF in the country is saying, let's spend

(14:16):
less money, and so that's trickling down and we're all
feeling the result of that, and until the FED stops
raising rates, we're going to continue to feel that. But also,
you want to work places where they're really, really thoughtful
and fugal with money, then those are places that make money.

Speaker 1 (14:32):
Molly my two cents on this or Alexa's right on
the money. The good leaders are the ones who are
focused on spending money where it helps to grow the
company and grow the people in the company. I would say,
if you're at a company with a younger founder and
this is his or her first time through, sometimes people
have to learn the hard way. If you're finding the
companies running now like you'd run a company, and if

(14:53):
you are building something that your consumers really like, you know,
maybe you're in the right place. You'll have to we
don't know where you work. You'll have to dig a
little bit more to know for yourself. Well, roll next
into to meet you from Berlin, who says, Hi.

Speaker 3 (15:06):
There, I'm a stopward developer and I'm a worried AI
is going to be taking over my job.

Speaker 1 (15:12):
I'm curious what's the most important skill who we should
be developing out of future proof our careers might be.
Thank you so much.

Speaker 2 (15:20):
So, first of all, I'm not worried that OFFER is
going to take your job. I actually just head dinner
with this amazing AI professor Kareem Lakhani, author of a
bunch of AI books, and AI is not going to
replace jobs. What what happened is that people with AI
will replace people that don't use AI. So punchline is,

(15:45):
you know, there's I had this amazing founder, this CEO
of Ironclad, on my podcast and iron Cloud's a AI
for lawyers, and he was a lawyer started the company
to leverage legal plus AI and you're an engineer, so
you know, you know Copilot and all the other operate
platforms out there. And at one point he was like,
am I going to put myself out of a job?
Is that what this technology is going to do and

(16:06):
then at one point he realized, oh no, I'm going
to make myself ten times more productive. And as of
the last year, the iron Cloud founder was saying, actually,
I'm going to make myself one thousand times more productive.
So what will happen with the human plus AI is
it's not that you will eradicate your job or be
out of a job. It's actually that you will be
able to have a bigger surface area of impact of

(16:28):
what you do and in a more efficient manner. You'll
be able to do things. So in verse, lean into
the technology, be a strongly adopter on everything that you can,
because that's the future.

Speaker 1 (16:41):
And by the way, the parts that it replaces are
the boring parts of our jobs. So like nobody wants
to format this seven paragraph email they were going to
send to the team to summarize them from the meeting.
It's like it's the most boring thing. So I'm glad
I was doing some of that for us. We're going
next into investing, where you've got a ton of experience.
Gabriella in New York says, I.

Speaker 5 (17:03):
Have an idea and I'd.

Speaker 4 (17:05):
Love to turn it into a business, but I don't
know how.

Speaker 5 (17:07):
To raise money. You both raise money and invest in money.

Speaker 4 (17:12):
How do I do it?

Speaker 5 (17:13):
What are the keys to pickcess.

Speaker 1 (17:16):
Alexa? You're seeing pitches every day. Which ones work, which
ones don't? What is your advice to someone who needs
capital to bring their vision to life?

Speaker 2 (17:25):
I mean it's really, really, really simple. We always look
for the founders that have these attributes. Number One, they're
truly obsessed with their idea. It's inducted them. It's like
it's not a Hey, I've been sitting here on a
spreadsheet and trying to come up with the grid of
the thing that maybe makes the most money. It's somebody

(17:46):
who has identified a big problem that they want to solve.
Number two, it is somebody who is living in the
future on that problem. They have already solved the problem,
they have a vision of how to solve it, and
they're living in the future. Why when that problem goes away,
what else is possible and gets better? Number three, they
are deeply confident that they're willing to put ten years

(18:10):
of their life into trying to solve that problem. And finally,
number four, they're extremely detailed in their thinking and they
littp lean into the pain. They don't shy away from
the Hey, this business model is not going to work.
What about this one. They're not defensive about those things.

(18:32):
They're like, you're writer, help me think, think with me,
those sort of dynamics. So those are the attributes that
you see. They are extremely passionate. They're living in the future.
It's a problem they live firsthand. They're super focused on
solving it. They don't lean out of hard things. They
lean into the hard things because the job of a
CEO is all day long you're solving the hardest pert

(18:52):
to your business. So if you don't do that early on,
if that muscle isn't there, it's really all hard to
solve your prop wolves.

Speaker 1 (19:00):
How far along was learned best when you raised your
first amount of money.

Speaker 2 (19:05):
I founded the company May of two thousand and seven,
and I raised my first amount of capital June of
two thousand and nine.

Speaker 1 (19:12):
So that's an important insight as well, because a lot
of people asked me about raising money when what they
have is an idea as opposed to real progress, real product,
market fit, real customers willing to pay them for what
they've built. And it sounds like you had established all
of those before you went on and went out and
asked someone to bet on you.

Speaker 2 (19:33):
I started building the plane. I was absolutely hell bent
on building the business, started building it. I put in
all my savings. I put in seventy five thousand dollars.
So the other thing, Mike, that I look for is
people who are really all in. That's real strandla game
really all in. They're not. I didn't want to be

(19:53):
a CEO. I wasn't looking to start a company. I
was infected by this idea and then I had to
go build it and created a lot. It's a personal
stress and pain to go do so, so I always
look for people, you know. I like to ask people, well,
if you're not doing this, what are you doing? And
the only answer is this, I'm just doing this. There's
no plan B.

Speaker 1 (20:13):
I love that. Yesmin and Istanbul where I'm told we
are now a top one hundred podcast, which is very exciting.

Speaker 5 (20:31):
Hi, I was wondering what trends you're seeing in technology
with startups specifically, and what do you think are some
of the promising investment areas well.

Speaker 2 (20:41):
At in fired, we like to invest where no one
else is looking, so wheneveryone's screaming AI or climate it's
time to run different direction. So we are very thesis driven.
We're constantly creating categories that we want to go dig into,
and you know, bodies of work we think they're, you know,
on plain sight, really big gaps, and we're general is fun.

(21:05):
So we cover everything from fintech to healthcare to consumer
tech SaaS you know, marketplaces, and then finally, you know,
the door is always open for a wildly talented entrepreneur
committed to building something for the next decade. And actually,
like one thing I want to add, I always say that,

(21:27):
like on the wall behind me should be a huge
sign that says there are no shortcuts in life. We
also really like to focus on people who recognize the
only way to the top is through our work. There's
no shortcuts, there's no like magic button where all of
a sudden everything works. You have to work really, really,
really hard to get lucky. And so we also just
like people that have an incredibly resilient mindset to work ethic.

Speaker 1 (21:50):
And almost I think I have a similar investment thesis
as you do. Just personally, I'm a little old fashioned.
I like companies that to solve real human problems as
opposed to sort of trend base themed based investments. I've
read it was this morning I read, you know, everything
was web three last year, and then it was NFTs
and now ninety five thousand I'm sorry, ninety five percent

(22:13):
of NFTs have zero value. Twenty three million people put
real money into NFTs as if it was an investment
vehicle and they have nothing for it, and it felt
like the hottest thing in the world. Then I was
being booked on like Good Morning America to talk about NFTs.
I I as you noted like good founders, good ideas,
solving real human problems, Yasmin, for whatever it's worth, is

(22:35):
certainly where I'd be looking. We have a you know,
one of the world's leading minds on personal finance here.
We definitely had a bunch of questions in this area, Alexa.
One of the ones I picked was Henri. Either Henry
or Henri, let's say Henri in New York.

Speaker 4 (22:52):
I'm just starting to make enough money to save and invest, Alexa.

Speaker 1 (22:57):
In your book, you talk about the fifty twenty savings formula, and.

Speaker 4 (23:01):
I'm really trying to stick to that. Where would you
both advise putting money today?

Speaker 2 (23:08):
Okay, I'm going to go real fast your MIC. I'm
gonna give everyone a mini financial plan. Number one, everybody listening.
You need to have an emergency savings account that is
either three six months or nine months nine months once
you make over one hundred k in your twenties three months.
But you need liquid cash earning, you know money market
A five percent you need zero you.

Speaker 1 (23:30):
Say nine months. That's to cover nine months of your
personal expenses.

Speaker 2 (23:33):
Like you need to have a job on thousand dollars,
it takes on average nine months to find an equivalent
job on the same career trajectory, so nine months. You
need no credit card debt, so zero credit card debt.
And you should be contributing the maximum to retirement. I
don't care if you're twenty one, twenty two, twenty five,
thirty one, thirty two, thirty five. Every year you need

(23:53):
to max out your retirement savings at work. That's either
through an IRA just about six thousand dollars or four
O one K, which is about twenty thousand dollars. That
is where you invest. That's called the monopoly step. You
cannot pass go until you can do those three things.
Once you can do those three things, if you then
have extra surplus then we start thinking about where to
invest your money, where to put it. And one great

(24:14):
place to put your money is simple. It's treasury bonds, right,
It's CDs where you're making five percent. And then if
you don't need the money for five years or longer,
then buy ETFs and index funds, the S and P
five hundred and set it and forget it and don't
look at it. But it is that simple when it
comes to your wallet.

Speaker 1 (24:35):
It's a little bit adjacent to the question and your answer,
But if I could also add, especially when you're in
the formative stages of your career, the long term, the
present value of your future earnings in your career is
your biggest asset right now, so also the investments that
you make in yourself. And there was a moment earlier

(24:55):
in my career when I was trying to put money
into an ETF but was also doing my own laundry
in a way that was just making me less productive,
was making it was taking hours out of what I
could have been putting into my career. And I found
that there was a moment when you know, my scarcest
resource became time and the time that I wanted to
invest in success and also investing in the things that

(25:19):
make you more personally productive. I found, as I've found
has it doesn't have ROI in the same way that
you can track in your personal savings account, but it
has significant ROI over the long arc of your your
career and your earnings. Aliyah in Atlanta.

Speaker 4 (25:37):
Alexa, you studied at Harvard's Happiness Lab, and Mike, you
wrote about this in your book and have been quoted
a lot on happiness at work. What's your advice for
more happiness when work is stressful? And now that you
have had six though, are you happier?

Speaker 1 (25:52):
Alexa?

Speaker 2 (25:53):
You know what's so funny? And Mike, I'm so glad
then you just asked that question. I think happiness is
a mindset happiness and I worked in the happiness lob
as you mentioned, and positive psychology. If you ask me, like,
what's my superpower, it is actually my positivity and even

(26:16):
through like chaos and everything's going wrong, and I'm like,
we're going to figure it out, everybody, it's gonna be great.
We're going to figure it out. And happiness is a
mindset that everybody can access and tap into. And there's
this great study where it's once you make over seventy
five thousand dollars. Financial improvement does not bring happiness once
you're above seventy five thousand dollars, meaning you can cover food,

(26:40):
roof over your head, et cetera. Which right now, you know,
roughly eighty percent of the country is paycheck to paycheck
and people are really really struggling. So so I don't
want to let you know, ignore that fact. But happiness,
your point of view, what brings joy in life is
actually never the big things. It's the really small things,
human connection and a great cup of coffee sitting, you know,

(27:03):
reading the paper. It's it's the little routines and rituals
that we all create. And so does success bring happiness?
You know, I think success brings fulfillment. Happiness is a mindset.

Speaker 1 (27:19):
And how would you differentiate fulfillment and happiness.

Speaker 2 (27:22):
There's a lot of content, So I'm gonna I'll keep
it simple. Happiness is is something that feels really uplifting
your good mood. Joy, So I'm gonna talk about joy.
Joy is actually having put your effort and love and

(27:43):
into something else and it thriving. So the difference, like
my kids don't make me happy, they make me joyful, right,
I'm pouring my blood speaent in tears. My work doesn't
make me happy, it makes me joyful again. Happiness is
like a small, you know, mindset, a cup of coffee.

(28:04):
Joy which is the real goal that we all want.
It's actually when your effort has gone into something else
that is thriving, and often, most often it's people. And
that's free. Mike, what I just said, every person on
the planet can access for not one dollar.

Speaker 1 (28:20):
Yeah, you know, I remember my last company. We were
working on a big deal and we had a board
meeting coming up, and it was like we had an
earnings call coming up, and it was a lot, and
it was stressful, and like we had the whole team
in the room and we were jamming her all three things,
and nobody looked like they were having a good time.
And I said, do you remember when you were in
business school or when you were junior in your career

(28:41):
and you thought that someday you'd be in the room
getting ready for the board meeting and the big acquisition
and the earnings call. You remember that like it's happening.
Try to enjoy it, And Alex, I'm with you, like
it's the journey is the fun part. It's the day
to day, it's the interacting with the team. It's the

(29:03):
find like finding a tough problem and then actually solving it.
And you know, I Leah, I would, I don't want
to misrepresent this. Having success is really awesome. I strongly
recommend it. It's a lot more fun to run a
race and win it than it is to run a
race and not win it. But if you think that
the happiness is going to come just from the finish line,

(29:26):
then you're doing it wrong. If you're already enjoying the journey,
then write Alexa then and I mean, not many people
are going to have a success the way you did.
If you enjoyed it all the way there and then
you get a home run like that, I mean, how's
that feel?

Speaker 2 (29:41):
Yep? And my first of all, Mike, you said it
much better. There was far more eloquent than what I said.
I'd really like what you said. And the other thing
I would just add is that people are magnetically attracted
to people that are positive and upbeat and happy. Oh yeah,
most the most powerful thing you can do every day
when you wake up is put on a smile. People

(30:01):
actually responded better to you all day long. It's really simple.
These little things that we are capable of doing that
allow us to be more successful are free.

Speaker 1 (30:12):
I worked at this lovely person and we got in
a taxi together one time and she said to the
taxi driver, what was the best part of your day?
And I thought, what a great way to ask that question,
and rather than how are you doing? Because like what's
everyone's natural first response, and you say how you doing,
it's like, oh the weather, oh the traffic, all the
uns in town. What's the good part? You're right to
your credit, Alexa bringing that positive energy, it really does,

(30:33):
and we certainly feel it here in this conversation today.
You've made my day happier. Thanks well, friends, That was
Alexavon Tobol. What an inspiring, brilliant, amazing leader. I've really
enjoyed that conversation. I hope you did too. Number one

(30:54):
thing I took away from it, what did it makes
to say with our acronym l I t TP lee
into the pain. I've never heard that advice before, But
if there was something that's been thematic across all of
these office hours conversations we've had so far, so We've
talked to people who've taken on really tough challenges, who've

(31:16):
had obstacles, who failed, and who just kept doing it,
and they all come to these conversations with an energy
that suggests to me that they've enjoyed it the entire time.
And that's what I heard from Alexa today. I heard
from someone who started a business dropping out of school
in the middle of the financial crisis, was in the

(31:38):
process of selling her company and having our baby all
at the same time. Who's taken on, you know, one
of the hardest jobs in the world, starting a business
from scratch, and enjoyed seemingly every step of it and
didn't feel bad for herself when it was hard, and
didn't throw a pity party when things were going wrong.

(32:00):
She leaned into the pain. I don't know. That's to me,
that sounds like pretty terrific advice. And I'll bet this
week there's gonna be some moment when you're gonna feel
the pain. I don't know what the pain is. Your
boss is the pain? Missing a number is the pain?
Not closing a deal is the pain? We all have it.
Think about this moment, Think about Alexa, ask yourself, what's

(32:24):
your version of leaning into the pain. We got some
amazing guests coming up the next few weeks, including Jim Citrin,
the number one recruiter of CEOs in the world, Mindy Grossman,
commerce legend and former CEO of Weight Watchers, my friend
Perkins Miller, the CEO of Fandom. It's the world's largest
community of gamers and fans and movie buffs. You can

(32:45):
ask any one of them anything on your mind. Text
or call me your questions at two point three four
one nine five nine six, or just hit me up
on LinkedIn or Instagram, et cetera at Mike Steib Again
Texter call it in at two one three four one
nine five nine six, or hit me up at Mike's
Steve on social media. I want to thank Alexa and

(33:07):
her team for getting this all set up, and of course,
as always, Jen, Cara, Meg, Jada, Matt and the whole
team at Blue Duck Media for making it happen, Dylan,
Sasha Gay and the whole gang at iHeart, and Ben
and the team at William Morris Endeavor for all of
their support. Office hours is a production of Blue Duck
Media and distributed by iHeartRadio. I Will see You next week, everybody,

(33:31):
stay on your grind.
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Host

Mike Steib

Mike Steib

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