February 3, 2025 • 33 mins
We're Back!
Christian McKenzie shares her experiences and insights from the venture capital world, explaining the risks and rewards of investing in startups. The episode highlights her journey from the fashion industry to venture capital, the importance of networking, and how supporting entrepreneurs goes beyond just funding.
• Exploring the nature of venture capital and its high-risk, high-reward dynamics
• Discussing how Lofty Ventures supports startups beyond investment
• Identifying ideal profiles for entrepreneurs seeking funding
• Networking strategies and relationship-building in venture capital
• Navigating personal journeys and adapting career paths
• The role of compensation in venture capital and long-term investment strategies
• Emphasizing the importance of diverse perspectives in entrepreneurship
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The thoughts, views, and opinions expressed on Career Cheat Code are those of the individual guests and do not necessarily reflect those of the host, affiliated organizations & employers. This podcast is intended for informational and inspirational purposes, highlighting the guests and their unique career journeys. We hope these stories inspire you to chase your purpose, define success on your own terms & take the next step in your career.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
My parents are preachers.
They met in seminary and, youknow, my dad immigrated here
from Jamaica for school and so,you know, like most immigrant
parents, you know, my dad islike, yeah, I need you to be a
doctor or, you know, go intocomputer programming.
And I was not interested in anyof those.
(00:20):
So I kind of wanted to provehim wrong, like I can make a
living, you know, in fashion,which they didn't think I could.
And so it was kind of like, youknow, going into the green and
saying, ok, I want to take careof myself.
They're not going to support megoing into fashion.
I have to figure it out.
Speaker 2 (00:36):
Welcome to Career Cheat Code.
In this podcast, you'll hearhow everyday people impact the
world through their careers.
Learn about their journey,career hacks and obstacles along
the way.
Whether you're already havingthe impact you want or are
searching for it, this is thepodcast for you.
All right, Welcome to the show.
Speaker 1 (00:52):
Thanks.
Speaker 2 (00:54):
How are you doing today?
Speaker 1 (00:55):
Good, you know I'm not much of a fall person, I
prefer summer.
But you know it'll be okay,Awesome.
Speaker 2 (01:04):
Well, I'm happy to get you on the show today and,
you know, let's just dive rightin, let's tell the world what it
is you do for a living.
Speaker 1 (01:11):
For sure.
I'm Christian McKenzie.
I am the director of a fundcalled Lofty Ventures, so we're
based in Chicago and we investin early stage startups.
We're a generalist fund, so anyindustry, we invest across
industries.
Just they need to be pre-seedto seed stage and be based in
Chicago preferably, but we'vealso made some bets in the
(01:32):
Midwest.
I manage those deals.
We also do a ton of programming.
We have free classes for peoplewho want to break into angel
investing.
We have an angel syndicate sowe can spin those up.
If people want to invest incompanies, either, you know,
send us deals or make individualinvestments themselves.
And you know, we hostnetworking events, we host off
(01:53):
sites.
So we kind of do a lot ofthings, I think, for you know a
company in this space.
But yeah, I've been in venturefor a few years.
It's my third career, but Ienjoy it Awesome.
Speaker 2 (02:04):
So what does that mean to be in venture capital
world, right Like, how does yourday look, how does your week
look like, what are you lookingfor and how are you able to
connect with some of theorganizations that are looking
for some of this funding?
Speaker 1 (02:17):
Yeah.
So venture capital is it's highrisk, high return kind of
investing right.
So it's kind of for people whoalready have a well-balanced
portfolio and want to addsomething different in.
This is kind of like super highrisk, super high return, so you
could lose all of your money.
You can make it rich.
It's kind of runs the gambit.
(02:37):
And so what we do is we scoutprivately held small companies
in the startup space, so usuallytech backed right.
So a software company isnormally what we invest in and
with that investment we build arelationship with the founder.
So we help them along the waywith any support we can provide,
whether it's introducing themto other investors, getting them
(03:01):
some specialists to help them,maybe with sales or operations
or some of their legal needs.
That's kind of the support weprovide and the goal is to help
them get to a bigger stage sothat they're ready for bigger
companies right.
A growth stage venture capitalfund that makes bigger bets than
we do.
(03:21):
Our average check size is 100Kinto a company.
So once they get to the sizewhere they need a million
dollars or $5 million andthey're following that path, the
end goal is either beingacquired or going public.
So either getting acquired byanother company or a private
equity firm or IPO-ing, and whenthey hit that exit, that's when
(03:45):
everybody who invested in thecompany gets their return.
So that's an ideal exit.
But you know it's high risk.
Most startups fail and so if itfails you lose all of your
money.
So it's a very specific assetclass.
But it's exciting because youget to bet on people's dreams,
right?
A lot of people.
When we meet them, they justhave an idea.
I don't think you cannecessarily make your idea
(04:08):
happen without some support.
You know it doesn't have to beventure capital, it could be
loans, it could be crowdfunding,but it's exciting to play a
role in getting something offthe ground.
Speaker 2 (04:17):
Absolutely, and this is, you know, as you said, high
risk, high reward, but also kindof has to be a little patient
right.
Like this capital should not beexpecting a return within a few
months.
How long do you typically seefor some of these organizations
to start turning some returns?
Speaker 1 (04:35):
On average, people wait about 10 years for their
venture capital investments toactually show some sign of you
know some financial event thatthey can benefit from.
So since I'm three years intothis career, I have not
personally made bets that I'vehad exits.
Not big exits actually would bemore accurate.
So, yeah, it's the long gameand it's for people who, you
(04:58):
know, have a little extra cashto do something, I guess,
exciting with or a little morerisky, a little more you know, I
don't know dramatic, becauseyou know obviously a safer thing
is the stock market.
This is not the place you go tolike put your money and keep it
safe.
This is a place you go becauseyou want to be part of something
(05:19):
that could be big.
Speaker 2 (05:21):
That makes sense.
So tell me more about some ofthese additional supports.
Right, so it's not just thefunding.
Tell me more about some of thesupport that you all provide or
work with the entrepreneurs on.
Speaker 1 (05:32):
I would say me personally.
I think my one of mysuperpowers is networking.
So I've had people approach meand say I need help with I need
a general manager, I need achief of staff, I need someone
to do content and marketing,helping them locate those people
and hire them.
You know, and maybe it'sfractional at first until they
have enough money to bring themon full time, we can help them
(05:54):
with their hiring needs.
Outside of that, you know,helping introduce them to other
investors that are early stageand looking to work with early
stage companies.
Also getting them just likeaccess right If they need
clients, if they need to be putin front of more people that
could use their service orproduct.
We do that as well.
And you know kind of standardthings most firms offer are AWS
(06:19):
credits or you know anopportunity to use HR software
at a fraction of the fee younormally would.
Those are the type of things wecan also lend to entrepreneurs
if they need it.
Speaker 2 (06:30):
So what's your kind of ideal type of profile?
Right, If I'm an entrepreneurlistening to this, how do I know
if I should contact Christian?
Speaker 1 (06:39):
Yeah, I mean we like to be the first check-in, so we
like being contacted super early.
I would say someone who kind ofknows a venture capital is
right for them.
Which would you know?
To make it clear they have somesales, they have some customers
.
They've been, you know, at itfor probably at least a year.
(07:00):
They're reaching product marketfit, which means that you know,
sometimes you launch somethingand it's very hard to find the
right customer, it's very hardto find the right niche.
Right, you are marketing yourservice to people in Kentucky,
but really New Yorkers are theones that like it more.
Right, like finding all of thatout.
You're at like a turning pointwhere you have identified those
(07:21):
things and really you knowyou've exhausted all of your
options to make it grow and youjust the capital is really
what's holding you back and youcan explain the business case as
to why that's a good time tocontact someone like us.
Speaker 2 (07:36):
How are you also then proactively finding some
entrepreneurs, like in the techspace, right?
Is this going to conferences?
Is this like hosting events?
Speaker 1 (07:50):
Like, how do you, how do you just find folks out
there?
I would say we, um, we don'tstruggle to find companies to
invest in, to be honest, but wedo do a little of the networking
, just, you know, to make surewe're not overlooking, um,
anybody who would be a good fit.
So we do speaking engagements,we sponsor events.
Last weekend, a company calledEvent New War, which we haven't
invested in but we have a greatrelationship with, hosted a
curator summit, and so Imoderated a panel.
(08:11):
Lofty Ventures sponsored thatevent just to kind of get in
front of people building coolthings.
So we do some of that outreachand we also host our own events.
Last, well, no, I'm thinkingwe're in 2025, but we're still
in 2024.
Last, well, no, I'm thinkingwe're in 2025, but we're still
in 2024.
Over the summer, we had aglamping retreat for founders
and investors, and so it wasthree days at OffMap, which is a
(08:32):
glamping location we investedin, and so we took people out
there.
We had a former contestant fromthree survivors.
Do survivor theme challenges,just do some bonding, do you
know?
Have some fun and get to knowsome new people.
So we definitely do stuff likethat, um, as well.
Speaker 2 (08:51):
Okay.
So it seems like a a reallykind of two-way communication
that happens, where you all areeither hosting or, uh, joining
events where folks are alreadygathering, um, and also just
having a call for call for folksto contact you all.
Tell me, how'd you get into theventure capital space?
Speaker 1 (09:10):
That was.
I would not recommend doing itthe way I did it.
It took a very long time.
I think it took about fiveyears for me to do so.
So my background is fashionretail.
I was a buyer, so I wasselecting products to go in
stores and I really lovedworking with entrepreneurs and
getting to know their story andgetting to help them.
(09:31):
But you know, when you're in acorporate job, you just kind of
have that one role and so I waslike, okay, I gotta do something
different.
And one of the speakers was anexecutive coach and I said, hey,
I have a big idea, can you helpme with that?
And he's like, absolutely.
So I worked with him to thisday.
(09:53):
But what we did was I pivoted toa startup in the retail space
because I was like, if I don'thave tech experience, who's
going to take me seriously as aninvestor if I've never actually
worked for a startup?
And then I went to work forMeta in New York, specifically
on consumer accounts, which wasaligned with my background.
And then I applied to businessschool.
(10:14):
I went to NYU Sternunfortunately, unfortunately
during the pandemic.
So I had six months in personand then a year and a half
remote.
And then, after I graduated, Ilanded a role at an
institutional fund called RedState Adventures and I was there
for two years and I joinedLofty about six months ago, got
it.
Speaker 2 (10:32):
So just to make sure I understand that path right.
So did you go into businessschool knowing that you wanted
to get into venture capital, ordid you have another goal in
mind?
Speaker 1 (10:42):
I was going to kind of upskill and make that pivot.
So I went with the intentionlike I want to be in venture
capital and I'm using thisopportunity to intern.
I had probably about fiveinternships at funds when I was
in business school to intern, tobuild that case, to focus on
the skills that I would need tobe in venture.
(11:02):
That was, you know, like thenumber, the main goal.
Speaker 2 (11:05):
Did you know someone in the space or like what kind
of planted that seed for you tothink that this was a space that
made sense for you?
Speaker 1 (11:12):
Loosely.
I have a family friend who wentinto venture Very different
story than me and he did itafter going to business school
as well.
He went to Kellogg and he hashis own funds in the suburbs of
Chicago.
So like I had exposure to likehigh net worth individuals who
(11:33):
went into it.
I am not a high net worthindividual, I'm a child of an
immigrant.
I didn't grow up with excess inthat way to kind of launch my
own thing.
So I did have exposure but itwas nothing like it is today.
Like Shark Tank wasn't a bigdeal, you know, it wasn't fuzzy
and cool.
There weren't a ton of peoplethat looked like me launching
(11:54):
funds when I went into it.
So I think I just I knew likesomething was happening and I
wanted to be a part of it inthat space and so I think I
actually pivoted at a reallygood time, because I think it
would be much harder for me toget it now than it was when I
did break in.
Speaker 2 (12:11):
Do you have advice for folks that are looking to
break in today?
Speaker 1 (12:15):
Yeah, I think what worked for me and a lot of my
friends that were bringing inventure at the same time is
having great deal flow andsending those deals to funds.
So, just to take a step back,the bread and butter of every
venture capital fund is havingaccess to really great deals and
(12:37):
the top tier firms.
They get exclusive access.
Grads straight out of Stanfordor dropouts who launch something
very cool through theirnetworks already, but they're
obviously you know, that is oneI don't know prototype that
people try to.
It's called pattern matching.
They try to say, okay, a lot ofStanford dropouts had unicorns,
(12:58):
let's go after Stanforddropouts or grads.
But that doesn't that means itcould be overlooking a ton of
other people, right?
So if you are following, youknow the Entrepreneurship Center
on your campus or you aretalking to maybe economic
development corporations andresources like in your local,
your county, your city, and youcan say, hey, I think this deal
(13:19):
would be a good fit for you guys, you want to take a look at it.
That means something and thatresonates with people.
If you're sending them gooddeals, that's a good way to get
the conversation started.
Like, hey, I can scout, I don'twork here, I don't have the
resources to go to every singleconference or be in every room I
need to be in, but I'm doingwhat I can.
So I think that is a way tokind of start the conversation.
(13:43):
Get internships or, you know,get a, get a.
It's called a venture scout Ifyou want to do that just for a
fund as a freelancer, so thatreally helps.
And I think also, building yourpersonal brand matters more
than ever.
So writing articles, you know,doing thought pieces, letting
people know what you think, ifyou have a unique perspective,
you know, or a take on a sectoror a movement or a trend, I
(14:06):
think that could definitely helpbuild your credibility in this
space and people will startseeing it was.
You know.
This is a great resource for us.
We should consider, you know,bringing them on or working with
them in some capacity.
Speaker 2 (14:19):
What's your favorite part of your role?
Speaker 1 (14:21):
The networking, the meeting new people, the hearing
about their hopes and dreams,the rush, when you know the
excitement, that you see thatthey're really excited about
solving a problem.
Or you know, I think we try toat our fund.
We prefer to work with peoplewho are solving a problem, that
they have not trying to get richor become famous, because they
(14:43):
just kind of can't sleep untilthat problem is solved, right,
like just anything that bothersyou and you're just like up day
and night, like I got to makesure I have a solution for this
thing.
Those are the people we kind oflove to work with and so just
the excitement and the rush andjust helping, trying to play a
role in helping them get there,I think is the part I like.
(15:04):
The most.
Speaker 2 (15:05):
That makes a lot of sense.
What is the most challengingpart of your?
Speaker 1 (15:08):
role.
I would say maybe difficultpeople who are unnecessarily
difficult, right Like we're hereto help.
And I've definitely met peoplewho feel entitled to work with
us or demand money from us, oryou know it's not a reciprocal
relationship, it's they're notgoing into it thinking, okay,
they want to be helpful and Ialso you know it goes both ways
(15:30):
We've met people who just kindof want the money but don't want
to really tell us what's goingon with the company or work with
us or be transparent.
You know it's really hard tomake an investment in a company
if you don't actually know howthe company's doing, and so I
guess managing thoseexpectations and trying to find
really great people to work withI think is rare.
So if you run into somebody whodoesn't really want to work
(15:51):
with you and doesn't want it tobe a two-way relationship, that
kind of is not my favorite part,but it happens.
Speaker 2 (15:57):
In venture capital right.
As someone that is part of afund like this, how does someone
like you make money in theinterim right I know you
mentioned?
Typically it's about 10 yearsbefore a successful exit or some
returns start coming back intothe fund.
So how does someone like youcontinue to be employed or
(16:18):
continue to make money in theinterim between year one and
nine?
Speaker 1 (16:21):
Yeah.
So just like most desk jobs,you have a salary right that
comes out of management fees.
So you know you do havecompensation while you're
waiting to for the investmentsto pan out.
So that's how you would supportyourself.
But you know, I think anotherthing that you have to keep in
(16:42):
mind is that you know you areinvesting other people's money
right.
So if you don't perform well,people won't give you money for
your next fund and your nextfund, because you have a certain
amount of time that you deploythat capital and then it's gone
and then you have to fundraiseAgain.
Our model is a little different.
We function more like a familyoffice.
So that just means that we'renot necessarily going out and
(17:05):
asking people for money.
We have like a family that werepresent and we invest their
money.
But in most funds, like aninstitutional fund, you have to
kind of make those numbers toget to the next level and people
aren't going to work in nomatter who you are.
People don't want to work withyou if you don't have the great
returns right.
If they're losing money workingwith you, they're not going to
keep working with you.
So I guess that's a motivator.
(17:26):
If you're motivated by stress.
You always have to keep that inmind.
It's not oh great, I got thisjob, I can just sit here for 10
years.
No, you have to perform or thiscompany will cease.
So it's not like I'm doing itfor free, out of the goodness of
my heart, and I can only getpaid if the bets do well.
But we can only stay inbusiness if the investments do
(17:49):
well.
Speaker 2 (17:49):
That makes sense.
So you have your salary.
Are there additional financialincentives if some of the
investments pan out really well?
Speaker 1 (17:58):
Yes, so, based on you know, whatever percentage
equity you take in a company,depending on how well it does,
you know, ideally, you'd want a10X your investment rate.
That's how a lot of the bigfunds continue to exist and have
billions of dollars of assetsunder management because they
(18:18):
betted on something that didreally, really well.
I think it's just waiting forthose bets to do well.
Speaker 2 (18:29):
That makes sense.
Yeah, so it sounds like as anorganization or as a fund, the
fund definitely makes theadditional returns.
I think what I'm hearing alsois as the person who found the
deal.
There's also some upside to youas an employee of the
organization to continue to findsome good fits.
Speaker 1 (18:44):
Yeah, and I would say that back to the venture
scouting that I mentioned.
If I were an outside venturescout and not a full-time
employee with my company,venture scouts also should get a
cut of the deal if it does well.
So there are other levers.
I don't know if lever is theright word, but there's other
things you can tap into forcompensation.
Speaker 2 (19:04):
That makes a lot of sense and I think accordingly.
So you're out there finding theright folks.
People shift jobs andeverything, but for the most
part if you're the folks thatare actually bringing in good
deals, there should be someincentives for that.
So that makes a lot of sense.
So how much money can someonemake in this type of field, in
venture capital generally?
Speaker 1 (19:24):
Like salary ranges.
I guess it depends on whatlevel you're at.
I think entry level.
I think you should expect ahundred K when you're moving up
to, you know, associate, seniorassociate the range is wide,
that could be.
You know, your associate, therange is wide.
That could be, you know,$125,000 to $250,000.
(19:47):
But again, you know, I thinkthis isn't a job that you can
just sit at for forever.
If you don't return the fundand have a profit, you can't
raise a second fund.
So I think that's probably whythe compensation structure is
that way.
And then I would say most ofthe people I know that are entry
level don't get carry, which isa percentage of the deal, but
once you're higher up you getcarry.
(20:08):
So that's the additionalincentive.
Right, the base is that salary,but if the deal pans out, then
you get a percentage of equityin the company and that's, I
think, where you could make moremoney potentially, because you
know you put in $10,000 and theyhave a 10x, you know 10 times
(20:28):
that you could walk home with.
Speaker 2 (20:30):
So I know earlier you mentioned starting a career.
More on the buyer side ofthings Would love to hear about
how did you even get there right?
So tell me, where'd you grow up, where were you born, what was
your upbringing like and whatdid you want to be when you were
like 15 years old?
Speaker 1 (20:47):
It's going to sound very shallow and silly.
I loved fashion my whole life.
I lived for prom and dressingup and, just you know, I did
some modeling.
You know nothing big.
And so I was like I need tolive in New York City, I need to
work in fashion.
So, from New Jersey, my parentsare preachers, they met in
(21:09):
seminary and you know, my dadimmigrated here from Jamaica for
school and so, you know, likemost immigrant parents, you know
, my dad is like yeah, I needyou to be a doctor or go into
computer programming, and I wasnot interested in any of those.
So I kind of wanted to provehim wrong.
I can make a living in fashion,which they didn't think I could
(21:33):
.
And so it was kind of likegoing into the green and saying,
ok, I have to take care ofmyself, they're not going to
support me going into fashion, Ihave to figure it out.
So I went to Spelman College inAtlanta for undergrad and the
school across the street, clarkAtlanta, had a fashion major
program.
So once I finished my coreclasses, I was taking classes
(21:53):
across the street as electivecredits, and when the recruiters
came to campus that were fromNew York and with retail, you
know I should.
I signed up for every interviewand you know I got an offer
from Macy's in New York and Iwas like, yeah, I'm in, that's
exactly where I need to be, I'min the right city, that's what I
want to do and it was I didn'tknow it at the time right, I was
(22:15):
just trying to get to New York.
It turned out to be a wonderfulexperience, training wise A lot
of retailers have trainingprograms, but at the time Macy's
was known as having one of thebest ones.
So I think for about threemonths I went into it, became a
trainee and it was a rotationalprogram, so you shadowed store
managers, you work with buyers,learn retail math.
(22:37):
You went on buying appointments, which means you go to like a
brand showroom and see whattheir collection is coming out
and how you make those decisionsbased on trend reports or based
on previous sales.
So I really think I got like areally great crash course in
breaking in for free, because Ipicked, you know, to work for
Macy's and I served for fiveyears.
(22:57):
So it was a great foundation,you know allowed me to be in New
York and go to fashion week andvolunteer and attend events and
network, and you know I sat onjunior boards of organizations
that supported the arts, sothat's that's how I started, not
knowing I would end up here,but you know it was an
experience I really loved.
Speaker 2 (23:18):
That's awesome.
So Jersey, originally Atlanta,so Spelman for school and then
back to New York.
So what then brings you toChicago?
How'd you end up there?
Speaker 1 (23:31):
Yeah.
So I think I am at the stage inlife where, to your point, when
you're 15, what do you want?
And I was like New York andfashion, and you know, when
you're no longer 15, and youknow all your money is eaten up
with rent, just to be in NewYork, it just kind of feels.
It didn't feel like I want itto sacrifice my retirement and
(23:54):
being comfortable just to say Ilive in New York anymore.
It was.
It was purely just like I hadjust kind of moved on to okay,
how do you get smarter?
You know, if you want to beable to angel invest, if you
want to be able to go toconferences and have new
experiences, you have to haveextra money to do that.
And I just didn't think I coulddo that in New York at the time
(24:14):
.
So purely it was, you know,looking for a major city,
looking for a nice quality oflife and looking for the ability
to have money to do interestingthings.
With All of this exposure Ihave to entrepreneurs and
investors who really, in theirfree time they're building
something in addition to the dayjob they have.
They're working with theirfriends to create professional
(24:36):
development groups and services,and I couldn't do that with if
I didn't have extra cash.
So I said, you know, where elsecould I thrive?
And Chicago has turned out tobe, you know, a really good
choice for me.
And also you know that firstjob I got after business school
was in Michigan, so I was kindof learning the Midwest and you
(24:57):
know where I might want to liveor where I might want to build a
life.
So you know, that's where I amnow.
Speaker 2 (25:04):
You know it's interesting because when you
look at just purely what youwant to do when you were 15 to
where you are now, they seempretty far apart.
But when you walk us throughthe story it actually makes a
lot of sense.
Speaker 1 (25:18):
I'm glad it does to you Tell, please can I have you
call my family.
Because, they're still worriedabout me, definitely.
Speaker 2 (25:25):
That's great.
That's great.
No, I think there's definitelya theme there, and you became an
entrepreneur to some of that aswell, and now being on the
other end of also kind ofsupporting entrepreneurs is just
, you know, I think itdefinitely.
There is a theme there, thereis a thread and something that
makes it all make sense.
Are there any books, podcasts,forms of media that you've
(25:47):
consumed that have helped shapeyou personally or professionally
that you just think peopleshould check this out?
Speaker 1 (25:53):
It's hard to pick one .
I definitely love to read andlove Audible.
I guess some of the classicsfor me that I probably pick up
every few years and read againand again are the Richest man in
Babylon or the Alchemist,because I think when I don't, I
read for information, not forentertainment, so they're really
(26:14):
nerdy and boring.
But the common thread betweenthe two is, you know, your life
journey is not linear, right,and if you get too hyper-focused
on a specific outcome and aspecific way to get there, you
miss life, and so and they, theyhave an undercurrent of, like
you know, building wealth andand just, you know, basic things
(26:35):
that you can do to kind ofprepare for a future.
But really it's about, like,learning to just allow the
journey, you to be led on ajourney, and not be so
prescriptive about how it looks,and that I find that comforting
because I think you know, Ifeel like I've had a lot of
lives right, when you're achildhood immigrant and you
(26:56):
really only have enough to likeyou have a roof over your head
and food to eat, but you mightnot have enough to like go to
the best school in the world or,you know, go to France with
your friends for fun, right Likeyou get creative and you might
feel like, oh, why don't I havethat?
Or that's holding me back fromwhere I want to be.
You're not allowing yourself tobe open, to be surprised by a
different way to get there.
(27:17):
You know, I've had a lot ofpeople kind of look out for me
and do things I didn't expectand got me places I never
thought I would be, and so thosebooks remind me of that.
And then I can't say I listento a lot of podcasts but there's
like one or two sub stacks thatI'm like that's pretty good.
I can't say a lot of people'sare a lot of people's you know
and just kind of like stuff Ialready know or already heard.
(27:39):
I want to say it's called FeedMe is my favorite one right now.
It's like a fashion journalistbut she has like she covers
politics, culture, all thethings, and that one I like.
Every time I read it I'm likeI'm so glad I like came across
this.
But Emily Sunderberg, feed Meis her subsect, so yeah.
Speaker 2 (28:02):
Are there any career hacks or career cheat codes that
you feel like you've acquiredor mastered along the way that
you're like if folks knew thisearlier, they would do this or
they should consider doing this.
Speaker 1 (28:16):
I feel like I'm a little proud of, like my cold
email game.
It's you know iterations of it.
But there are two things Istill do if I'm trying to get in
front of somebody that I'mhaving difficulty getting in
touch with.
One is you know, sometimes yougo to a conference and you can't
make it to every singlebreakout session or every single
you know speech.
(28:36):
You know, either you can'tafford the ticket to go to those
or it was just there was aconflict in all the things you
want to go to, and so sometimeswhat I'll do is like, oh man, I
wish I could have gotten infront of that person.
I will go on LinkedIn, eventhough I think they might be
doing away with the hashtags,but I'll click the hashtag from
the conference and I will lookup that person, like what their,
(29:00):
how their panel went, what weresome of the takeaways, what
people are posting about it, andyou know I'll message them and
I'll be like hey, I saw thisconference, I saw that you spoke
.
I'm so sorry I missed it.
These are some of the things Itook away just from based on the
LinkedIn conversations about it.
It sounded impactful.
Do you mind if I do a follow-upwith you just to get the
information.
I didn't have a chance to getit and I'm so sorry it was
scheduled at this time and I wasin this room, but I promise I
(29:22):
was there just personalizing it.
I get a lot of cold messagesthat are just like hi, we have
things in common and we knowpeople in common.
Do you want to chat for 30minutes?
And I'm like, oh my God, I getthose like five a day.
There's no way I can just chatwith random people because they
feel like it Right, like tell mewhy, tell me what I can do for
you, tell me what you're tryingto get at specifically and I can
(29:44):
opt in or not.
So that's kind of worked for me.
And then I tell this to like mymentees all the time.
I'm a mentor with thisorganization called Gen Z VCs
for people who want to breakinto venture and are early in
their career.
A lot of people aren't going toturn down a speaking engagement
.
Right, that's free press forthem.
(30:13):
So say I did this when I was atStern.
I created a series of firesidechats with venture capitalists
in the specific industries Iwanted to work in with one of
our entrepreneurship centers andI moderated them and so my name
is now aligned with GPs offunds and so that allowed me to
have the conversation, to getinternships, to get in front of
(30:33):
them, to network with them, toget introductions.
So I would say, be thoughtfuland have something to offer and
not just say, hey, I want yourtime, just because I want it.
To say this is why I want yourtime, this is why I could feel
it was beneficial and I did myresearch before even reaching
out to you, so you don't evenhave to fill in the blanks.
I'm going to actually ask somekind of hard hitting questions
(30:56):
because I know who I'm talkingto and I know what I want to
talk about.
Speaker 2 (30:59):
These are some great cheat codes.
I appreciate that, and it alsogoes back to the networking
piece of your role being yourfavorite part.
It all comes together when yougive away the cheat code, so
that's helpful.
Thank you, yeah.
Is there anything else wehaven't discussed that the world
should know about?
Christian?
Speaker 1 (31:15):
I think I'm in a stage where I'm getting in touch
with my roots and allowing thatto kind of be shared outwardly.
So you know, not that I wasever like embarrassed by who I
was, but I just never talkedabout being Jamaican or being
the child of an immigrant.
And, depending on where yourfamily's from or you know what
you guys are going through, somefamilies ask you to assimilate
(31:38):
right, and so an example of thatis that my, the dialect of
Jamaica, is Patois, and myfather never spoke it in front
of me as a kid because he wantedme to speak proper English, and
you know not have any issueswith my pronunciation or you
know being treated a certain waybased on how I pronounce things
, and you know, I think I can'tspeak Patois today, which I wish
(31:59):
I could, and I actually, youknow, have like a text.
It's like an app that changesmy text back and forth from
Patois, just to like send myfriends who are also Jamaican,
and so I'm leaning into myheritage a little more.
That being said, so now whenit's Caribbean American Heritage
Month, I post about all of thepeople in the venture and
startup space who are ofCaribbean descent, just if you
(32:24):
want to follow them or learnmore about us.
I host a dinner party series forinvestors.
It wasn't Caribbean specific atfirst, but the more people I
talked in the space are like Ididn't know that about you.
That's really cool.
It's like huh, maybe we shouldhave like a Caribbean VC event.
So I'm hosting one coming upsoon with people that I've been
sharing about who I am and myjourney, which has been kind of
fun.
And then in Chicago, which youknow obviously doesn't have as
(32:46):
large a Korean population as theEast coast, I've had to go out
of my way to find great Jamaicanfood or make friends with my
same background and I have likea little crew now we have a
group chat and we go to moviesand we have dinner parties and
it's been a fun thing that Inever leaned into, but I am now
and it just makes you knowChicago feel a little more like
home.
It's not New Jersey or New York, but it's still a special place
(33:09):
and so that's been fun.
Speaker 2 (33:11):
Thank you for joining us on Career Cheat Code today.
I really appreciate your time.
Speaker 1 (33:14):
Yeah, thanks for having me.
Speaker 2 (33:15):
I hope you enjoyed this episode.
If you did and believe on themission we're on, please like,
rate and subscribe to thispodcast on whatever platform
you're using, and share thispodcast with your friends and
your networks.
Make sure you follow us onInstagram and LinkedIn at Career
Cheat Code and tell us peopleor careers you would like to see
highlighted.
See you next week with somemore cheat codes.
Peace.
My parents are preachers.
They met in seminary and, youknow, my dad immigrated here
from Jamaica for school and so,you know, like most immigrant
parents, you know, my dad islike, yeah, I need you to be a
doctor or, you know, go intocomputer programming.
And I was not interested in anyof those.
(00:20):
So I kind of wanted to provehim wrong, like I can make a
living, you know, in fashion,which they didn't think I could.
And so it was kind of like, youknow, going into the green and
saying, ok, I want to take careof myself.
They're not going to support megoing into fashion.
I have to figure it out.
Speaker 2 (00:36):
Welcome to Career Cheat Code.
In this podcast, you'll hearhow everyday people impact the
world through their careers.
Learn about their journey,career hacks and obstacles along
the way.
Whether you're already havingthe impact you want or are
searching for it, this is thepodcast for you.
All right, Welcome to the show.
Speaker 1 (00:52):
Thanks.
Speaker 2 (00:54):
How are you doing today?
Speaker 1 (00:55):
Good, you know I'm not much of a fall person, I
prefer summer.
But you know it'll be okay,Awesome.
Speaker 2 (01:04):
Well, I'm happy to get you on the show today and,
you know, let's just dive rightin, let's tell the world what it
is you do for a living.
Speaker 1 (01:11):
For sure.
I'm Christian McKenzie.
I am the director of a fundcalled Lofty Ventures, so we're
based in Chicago and we investin early stage startups.
We're a generalist fund, so anyindustry, we invest across
industries.
Just they need to be pre-seedto seed stage and be based in
Chicago preferably, but we'vealso made some bets in the
(01:32):
Midwest.
I manage those deals.
We also do a ton of programming.
We have free classes for peoplewho want to break into angel
investing.
We have an angel syndicate sowe can spin those up.
If people want to invest incompanies, either, you know,
send us deals or make individualinvestments themselves.
And you know, we hostnetworking events, we host off
(01:53):
sites.
So we kind of do a lot ofthings, I think, for you know a
company in this space.
But yeah, I've been in venturefor a few years.
It's my third career, but Ienjoy it Awesome.
Speaker 2 (02:04):
So what does that mean to be in venture capital
world, right Like, how does yourday look, how does your week
look like, what are you lookingfor and how are you able to
connect with some of theorganizations that are looking
for some of this funding?
Speaker 1 (02:17):
Yeah.
So venture capital is it's highrisk, high return kind of
investing right.
So it's kind of for people whoalready have a well-balanced
portfolio and want to addsomething different in.
This is kind of like super highrisk, super high return, so you
could lose all of your money.
You can make it rich.
It's kind of runs the gambit.
(02:37):
And so what we do is we scoutprivately held small companies
in the startup space, so usuallytech backed right.
So a software company isnormally what we invest in and
with that investment we build arelationship with the founder.
So we help them along the waywith any support we can provide,
whether it's introducing themto other investors, getting them
(03:01):
some specialists to help them,maybe with sales or operations
or some of their legal needs.
That's kind of the support weprovide and the goal is to help
them get to a bigger stage sothat they're ready for bigger
companies right.
A growth stage venture capitalfund that makes bigger bets than
we do.
(03:21):
Our average check size is 100Kinto a company.
So once they get to the sizewhere they need a million
dollars or $5 million andthey're following that path, the
end goal is either beingacquired or going public.
So either getting acquired byanother company or a private
equity firm or IPO-ing, and whenthey hit that exit, that's when
(03:45):
everybody who invested in thecompany gets their return.
So that's an ideal exit.
But you know it's high risk.
Most startups fail and so if itfails you lose all of your
money.
So it's a very specific assetclass.
But it's exciting because youget to bet on people's dreams,
right?
A lot of people.
When we meet them, they justhave an idea.
I don't think you cannecessarily make your idea
(04:08):
happen without some support.
You know it doesn't have to beventure capital, it could be
loans, it could be crowdfunding,but it's exciting to play a
role in getting something offthe ground.
Speaker 2 (04:17):
Absolutely, and this is, you know, as you said, high
risk, high reward, but also kindof has to be a little patient
right.
Like this capital should not beexpecting a return within a few
months.
How long do you typically seefor some of these organizations
to start turning some returns?
Speaker 1 (04:35):
On average, people wait about 10 years for their
venture capital investments toactually show some sign of you
know some financial event thatthey can benefit from.
So since I'm three years intothis career, I have not
personally made bets that I'vehad exits.
Not big exits actually would bemore accurate.
So, yeah, it's the long gameand it's for people who, you
(04:58):
know, have a little extra cashto do something, I guess,
exciting with or a little morerisky, a little more you know, I
don't know dramatic, becauseyou know obviously a safer thing
is the stock market.
This is not the place you go tolike put your money and keep it
safe.
This is a place you go becauseyou want to be part of something
(05:19):
that could be big.
Speaker 2 (05:21):
That makes sense.
So tell me more about some ofthese additional supports.
Right, so it's not just thefunding.
Tell me more about some of thesupport that you all provide or
work with the entrepreneurs on.
Speaker 1 (05:32):
I would say me personally.
I think my one of mysuperpowers is networking.
So I've had people approach meand say I need help with I need
a general manager, I need achief of staff, I need someone
to do content and marketing,helping them locate those people
and hire them.
You know, and maybe it'sfractional at first until they
have enough money to bring themon full time, we can help them
(05:54):
with their hiring needs.
Outside of that, you know,helping introduce them to other
investors that are early stageand looking to work with early
stage companies.
Also getting them just likeaccess right If they need
clients, if they need to be putin front of more people that
could use their service orproduct.
We do that as well.
And you know kind of standardthings most firms offer are AWS
(06:19):
credits or you know anopportunity to use HR software
at a fraction of the fee younormally would.
Those are the type of things wecan also lend to entrepreneurs
if they need it.
Speaker 2 (06:30):
So what's your kind of ideal type of profile?
Right, If I'm an entrepreneurlistening to this, how do I know
if I should contact Christian?
Speaker 1 (06:39):
Yeah, I mean we like to be the first check-in, so we
like being contacted super early.
I would say someone who kind ofknows a venture capital is
right for them.
Which would you know?
To make it clear they have somesales, they have some customers
.
They've been, you know, at itfor probably at least a year.
(07:00):
They're reaching product marketfit, which means that you know,
sometimes you launch somethingand it's very hard to find the
right customer, it's very hardto find the right niche.
Right, you are marketing yourservice to people in Kentucky,
but really New Yorkers are theones that like it more.
Right, like finding all of thatout.
You're at like a turning pointwhere you have identified those
(07:21):
things and really you knowyou've exhausted all of your
options to make it grow and youjust the capital is really
what's holding you back and youcan explain the business case as
to why that's a good time tocontact someone like us.
Speaker 2 (07:36):
How are you also then proactively finding some
entrepreneurs, like in the techspace, right?
Is this going to conferences?
Is this like hosting events?
Speaker 1 (07:50):
Like, how do you, how do you just find folks out
there?
I would say we, um, we don'tstruggle to find companies to
invest in, to be honest, but wedo do a little of the networking
, just, you know, to make surewe're not overlooking, um,
anybody who would be a good fit.
So we do speaking engagements,we sponsor events.
Last weekend, a company calledEvent New War, which we haven't
invested in but we have a greatrelationship with, hosted a
curator summit, and so Imoderated a panel.
(08:11):
Lofty Ventures sponsored thatevent just to kind of get in
front of people building coolthings.
So we do some of that outreachand we also host our own events.
Last, well, no, I'm thinkingwe're in 2025, but we're still
in 2024.
Last, well, no, I'm thinkingwe're in 2025, but we're still
in 2024.
Over the summer, we had aglamping retreat for founders
and investors, and so it wasthree days at OffMap, which is a
(08:32):
glamping location we investedin, and so we took people out
there.
We had a former contestant fromthree survivors.
Do survivor theme challenges,just do some bonding, do you
know?
Have some fun and get to knowsome new people.
So we definitely do stuff likethat, um, as well.
Speaker 2 (08:51):
Okay.
So it seems like a a reallykind of two-way communication
that happens, where you all areeither hosting or, uh, joining
events where folks are alreadygathering, um, and also just
having a call for call for folksto contact you all.
Tell me, how'd you get into theventure capital space?
Speaker 1 (09:10):
That was.
I would not recommend doing itthe way I did it.
It took a very long time.
I think it took about fiveyears for me to do so.
So my background is fashionretail.
I was a buyer, so I wasselecting products to go in
stores and I really lovedworking with entrepreneurs and
getting to know their story andgetting to help them.
(09:31):
But you know, when you're in acorporate job, you just kind of
have that one role and so I waslike, okay, I gotta do something
different.
And one of the speakers was anexecutive coach and I said, hey,
I have a big idea, can you helpme with that?
And he's like, absolutely.
So I worked with him to thisday.
(09:53):
But what we did was I pivoted toa startup in the retail space
because I was like, if I don'thave tech experience, who's
going to take me seriously as aninvestor if I've never actually
worked for a startup?
And then I went to work forMeta in New York, specifically
on consumer accounts, which wasaligned with my background.
And then I applied to businessschool.
(10:14):
I went to NYU Sternunfortunately, unfortunately
during the pandemic.
So I had six months in personand then a year and a half
remote.
And then, after I graduated, Ilanded a role at an
institutional fund called RedState Adventures and I was there
for two years and I joinedLofty about six months ago, got
it.
Speaker 2 (10:32):
So just to make sure I understand that path right.
So did you go into businessschool knowing that you wanted
to get into venture capital, ordid you have another goal in
mind?
Speaker 1 (10:42):
I was going to kind of upskill and make that pivot.
So I went with the intentionlike I want to be in venture
capital and I'm using thisopportunity to intern.
I had probably about fiveinternships at funds when I was
in business school to intern, tobuild that case, to focus on
the skills that I would need tobe in venture.
(11:02):
That was, you know, like thenumber, the main goal.
Speaker 2 (11:05):
Did you know someone in the space or like what kind
of planted that seed for you tothink that this was a space that
made sense for you?
Speaker 1 (11:12):
Loosely.
I have a family friend who wentinto venture Very different
story than me and he did itafter going to business school
as well.
He went to Kellogg and he hashis own funds in the suburbs of
Chicago.
So like I had exposure to likehigh net worth individuals who
(11:33):
went into it.
I am not a high net worthindividual, I'm a child of an
immigrant.
I didn't grow up with excess inthat way to kind of launch my
own thing.
So I did have exposure but itwas nothing like it is today.
Like Shark Tank wasn't a bigdeal, you know, it wasn't fuzzy
and cool.
There weren't a ton of peoplethat looked like me launching
(11:54):
funds when I went into it.
So I think I just I knew likesomething was happening and I
wanted to be a part of it inthat space and so I think I
actually pivoted at a reallygood time, because I think it
would be much harder for me toget it now than it was when I
did break in.
Speaker 2 (12:11):
Do you have advice for folks that are looking to
break in today?
Speaker 1 (12:15):
Yeah, I think what worked for me and a lot of my
friends that were bringing inventure at the same time is
having great deal flow andsending those deals to funds.
So, just to take a step back,the bread and butter of every
venture capital fund is havingaccess to really great deals and
(12:37):
the top tier firms.
They get exclusive access.
Grads straight out of Stanfordor dropouts who launch something
very cool through theirnetworks already, but they're
obviously you know, that is oneI don't know prototype that
people try to.
It's called pattern matching.
They try to say, okay, a lot ofStanford dropouts had unicorns,
(12:58):
let's go after Stanforddropouts or grads.
But that doesn't that means itcould be overlooking a ton of
other people, right?
So if you are following, youknow the Entrepreneurship Center
on your campus or you aretalking to maybe economic
development corporations andresources like in your local,
your county, your city, and youcan say, hey, I think this deal
(13:19):
would be a good fit for you guys, you want to take a look at it.
That means something and thatresonates with people.
If you're sending them gooddeals, that's a good way to get
the conversation started.
Like, hey, I can scout, I don'twork here, I don't have the
resources to go to every singleconference or be in every room I
need to be in, but I'm doingwhat I can.
So I think that is a way tokind of start the conversation.
(13:43):
Get internships or, you know,get a, get a.
It's called a venture scout Ifyou want to do that just for a
fund as a freelancer, so thatreally helps.
And I think also, building yourpersonal brand matters more
than ever.
So writing articles, you know,doing thought pieces, letting
people know what you think, ifyou have a unique perspective,
you know, or a take on a sectoror a movement or a trend, I
(14:06):
think that could definitely helpbuild your credibility in this
space and people will startseeing it was.
You know.
This is a great resource for us.
We should consider, you know,bringing them on or working with
them in some capacity.
Speaker 2 (14:19):
What's your favorite part of your role?
Speaker 1 (14:21):
The networking, the meeting new people, the hearing
about their hopes and dreams,the rush, when you know the
excitement, that you see thatthey're really excited about
solving a problem.
Or you know, I think we try toat our fund.
We prefer to work with peoplewho are solving a problem, that
they have not trying to get richor become famous, because they
(14:43):
just kind of can't sleep untilthat problem is solved, right,
like just anything that bothersyou and you're just like up day
and night, like I got to makesure I have a solution for this
thing.
Those are the people we kind oflove to work with and so just
the excitement and the rush andjust helping, trying to play a
role in helping them get there,I think is the part I like.
(15:04):
The most.
Speaker 2 (15:05):
That makes a lot of sense.
What is the most challengingpart of your?
Speaker 1 (15:08):
role.
I would say maybe difficultpeople who are unnecessarily
difficult, right Like we're hereto help.
And I've definitely met peoplewho feel entitled to work with
us or demand money from us, oryou know it's not a reciprocal
relationship, it's they're notgoing into it thinking, okay,
they want to be helpful and Ialso you know it goes both ways
(15:30):
We've met people who just kindof want the money but don't want
to really tell us what's goingon with the company or work with
us or be transparent.
You know it's really hard tomake an investment in a company
if you don't actually know howthe company's doing, and so I
guess managing thoseexpectations and trying to find
really great people to work withI think is rare.
So if you run into somebody whodoesn't really want to work
(15:51):
with you and doesn't want it tobe a two-way relationship, that
kind of is not my favorite part,but it happens.
Speaker 2 (15:57):
In venture capital right.
As someone that is part of afund like this, how does someone
like you make money in theinterim right I know you
mentioned?
Typically it's about 10 yearsbefore a successful exit or some
returns start coming back intothe fund.
So how does someone like youcontinue to be employed or
(16:18):
continue to make money in theinterim between year one and
nine?
Speaker 1 (16:21):
Yeah.
So just like most desk jobs,you have a salary right that
comes out of management fees.
So you know you do havecompensation while you're
waiting to for the investmentsto pan out.
So that's how you would supportyourself.
But you know, I think anotherthing that you have to keep in
(16:42):
mind is that you know you areinvesting other people's money
right.
So if you don't perform well,people won't give you money for
your next fund and your nextfund, because you have a certain
amount of time that you deploythat capital and then it's gone
and then you have to fundraiseAgain.
Our model is a little different.
We function more like a familyoffice.
So that just means that we'renot necessarily going out and
(17:05):
asking people for money.
We have like a family that werepresent and we invest their
money.
But in most funds, like aninstitutional fund, you have to
kind of make those numbers toget to the next level and people
aren't going to work in nomatter who you are.
People don't want to work withyou if you don't have the great
returns right.
If they're losing money workingwith you, they're not going to
keep working with you.
So I guess that's a motivator.
(17:26):
If you're motivated by stress.
You always have to keep that inmind.
It's not oh great, I got thisjob, I can just sit here for 10
years.
No, you have to perform or thiscompany will cease.
So it's not like I'm doing itfor free, out of the goodness of
my heart, and I can only getpaid if the bets do well.
But we can only stay inbusiness if the investments do
(17:49):
well.
Speaker 2 (17:49):
That makes sense.
So you have your salary.
Are there additional financialincentives if some of the
investments pan out really well?
Speaker 1 (17:58):
Yes, so, based on you know, whatever percentage
equity you take in a company,depending on how well it does,
you know, ideally, you'd want a10X your investment rate.
That's how a lot of the bigfunds continue to exist and have
billions of dollars of assetsunder management because they
(18:18):
betted on something that didreally, really well.
I think it's just waiting forthose bets to do well.
Speaker 2 (18:29):
That makes sense.
Yeah, so it sounds like as anorganization or as a fund, the
fund definitely makes theadditional returns.
I think what I'm hearing alsois as the person who found the
deal.
There's also some upside to youas an employee of the
organization to continue to findsome good fits.
Speaker 1 (18:44):
Yeah, and I would say that back to the venture
scouting that I mentioned.
If I were an outside venturescout and not a full-time
employee with my company,venture scouts also should get a
cut of the deal if it does well.
So there are other levers.
I don't know if lever is theright word, but there's other
things you can tap into forcompensation.
Speaker 2 (19:04):
That makes a lot of sense and I think accordingly.
So you're out there finding theright folks.
People shift jobs andeverything, but for the most
part if you're the folks thatare actually bringing in good
deals, there should be someincentives for that.
So that makes a lot of sense.
So how much money can someonemake in this type of field, in
venture capital generally?
Speaker 1 (19:24):
Like salary ranges.
I guess it depends on whatlevel you're at.
I think entry level.
I think you should expect ahundred K when you're moving up
to, you know, associate, seniorassociate the range is wide,
that could be.
You know, your associate, therange is wide.
That could be, you know,$125,000 to $250,000.
(19:47):
But again, you know, I thinkthis isn't a job that you can
just sit at for forever.
If you don't return the fundand have a profit, you can't
raise a second fund.
So I think that's probably whythe compensation structure is
that way.
And then I would say most ofthe people I know that are entry
level don't get carry, which isa percentage of the deal, but
once you're higher up you getcarry.
(20:08):
So that's the additionalincentive.
Right, the base is that salary,but if the deal pans out, then
you get a percentage of equityin the company and that's, I
think, where you could make moremoney potentially, because you
know you put in $10,000 and theyhave a 10x, you know 10 times
(20:28):
that you could walk home with.
Speaker 2 (20:30):
So I know earlier you mentioned starting a career.
More on the buyer side ofthings Would love to hear about
how did you even get there right?
So tell me, where'd you grow up, where were you born, what was
your upbringing like and whatdid you want to be when you were
like 15 years old?
Speaker 1 (20:47):
It's going to sound very shallow and silly.
I loved fashion my whole life.
I lived for prom and dressingup and, just you know, I did
some modeling.
You know nothing big.
And so I was like I need tolive in New York City, I need to
work in fashion.
So, from New Jersey, my parentsare preachers, they met in
(21:09):
seminary and you know, my dadimmigrated here from Jamaica for
school and so, you know, likemost immigrant parents, you know
, my dad is like yeah, I needyou to be a doctor or go into
computer programming, and I wasnot interested in any of those.
So I kind of wanted to provehim wrong.
I can make a living in fashion,which they didn't think I could
(21:33):
.
And so it was kind of likegoing into the green and saying,
ok, I have to take care ofmyself, they're not going to
support me going into fashion, Ihave to figure it out.
So I went to Spelman College inAtlanta for undergrad and the
school across the street, clarkAtlanta, had a fashion major
program.
So once I finished my coreclasses, I was taking classes
(21:53):
across the street as electivecredits, and when the recruiters
came to campus that were fromNew York and with retail, you
know I should.
I signed up for every interviewand you know I got an offer
from Macy's in New York and Iwas like, yeah, I'm in, that's
exactly where I need to be, I'min the right city, that's what I
want to do and it was I didn'tknow it at the time right, I was
(22:15):
just trying to get to New York.
It turned out to be a wonderfulexperience, training wise A lot
of retailers have trainingprograms, but at the time Macy's
was known as having one of thebest ones.
So I think for about threemonths I went into it, became a
trainee and it was a rotationalprogram, so you shadowed store
managers, you work with buyers,learn retail math.
(22:37):
You went on buying appointments, which means you go to like a
brand showroom and see whattheir collection is coming out
and how you make those decisionsbased on trend reports or based
on previous sales.
So I really think I got like areally great crash course in
breaking in for free, because Ipicked, you know, to work for
Macy's and I served for fiveyears.
(22:57):
So it was a great foundation,you know allowed me to be in New
York and go to fashion week andvolunteer and attend events and
network, and you know I sat onjunior boards of organizations
that supported the arts, sothat's that's how I started, not
knowing I would end up here,but you know it was an
experience I really loved.
Speaker 2 (23:18):
That's awesome.
So Jersey, originally Atlanta,so Spelman for school and then
back to New York.
So what then brings you toChicago?
How'd you end up there?
Speaker 1 (23:31):
Yeah.
So I think I am at the stage inlife where, to your point, when
you're 15, what do you want?
And I was like New York andfashion, and you know, when
you're no longer 15, and youknow all your money is eaten up
with rent, just to be in NewYork, it just kind of feels.
It didn't feel like I want itto sacrifice my retirement and
(23:54):
being comfortable just to say Ilive in New York anymore.
It was.
It was purely just like I hadjust kind of moved on to okay,
how do you get smarter?
You know, if you want to beable to angel invest, if you
want to be able to go toconferences and have new
experiences, you have to haveextra money to do that.
And I just didn't think I coulddo that in New York at the time
(24:14):
.
So purely it was, you know,looking for a major city,
looking for a nice quality oflife and looking for the ability
to have money to do interestingthings.
With All of this exposure Ihave to entrepreneurs and
investors who really, in theirfree time they're building
something in addition to the dayjob they have.
They're working with theirfriends to create professional
(24:36):
development groups and services,and I couldn't do that with if
I didn't have extra cash.
So I said, you know, where elsecould I thrive?
And Chicago has turned out tobe, you know, a really good
choice for me.
And also you know that firstjob I got after business school
was in Michigan, so I was kindof learning the Midwest and you
(24:57):
know where I might want to liveor where I might want to build a
life.
So you know, that's where I amnow.
Speaker 2 (25:04):
You know it's interesting because when you
look at just purely what youwant to do when you were 15 to
where you are now, they seempretty far apart.
But when you walk us throughthe story it actually makes a
lot of sense.
Speaker 1 (25:18):
I'm glad it does to you Tell, please can I have you
call my family.
Because, they're still worriedabout me, definitely.
Speaker 2 (25:25):
That's great.
That's great.
No, I think there's definitelya theme there, and you became an
entrepreneur to some of that aswell, and now being on the
other end of also kind ofsupporting entrepreneurs is just
, you know, I think itdefinitely.
There is a theme there, thereis a thread and something that
makes it all make sense.
Are there any books, podcasts,forms of media that you've
(25:47):
consumed that have helped shapeyou personally or professionally
that you just think peopleshould check this out?
Speaker 1 (25:53):
It's hard to pick one .
I definitely love to read andlove Audible.
I guess some of the classicsfor me that I probably pick up
every few years and read againand again are the Richest man in
Babylon or the Alchemist,because I think when I don't, I
read for information, not forentertainment, so they're really
(26:14):
nerdy and boring.
But the common thread betweenthe two is, you know, your life
journey is not linear, right,and if you get too hyper-focused
on a specific outcome and aspecific way to get there, you
miss life, and so and they, theyhave an undercurrent of, like
you know, building wealth andand just, you know, basic things
(26:35):
that you can do to kind ofprepare for a future.
But really it's about, like,learning to just allow the
journey, you to be led on ajourney, and not be so
prescriptive about how it looks,and that I find that comforting
because I think you know, Ifeel like I've had a lot of
lives right, when you're achildhood immigrant and you
(26:56):
really only have enough to likeyou have a roof over your head
and food to eat, but you mightnot have enough to like go to
the best school in the world or,you know, go to France with
your friends for fun, right Likeyou get creative and you might
feel like, oh, why don't I havethat?
Or that's holding me back fromwhere I want to be.
You're not allowing yourself tobe open, to be surprised by a
different way to get there.
(27:17):
You know, I've had a lot ofpeople kind of look out for me
and do things I didn't expectand got me places I never
thought I would be, and so thosebooks remind me of that.
And then I can't say I listento a lot of podcasts but there's
like one or two sub stacks thatI'm like that's pretty good.
I can't say a lot of people'sare a lot of people's you know
and just kind of like stuff Ialready know or already heard.
(27:39):
I want to say it's called FeedMe is my favorite one right now.
It's like a fashion journalistbut she has like she covers
politics, culture, all thethings, and that one I like.
Every time I read it I'm likeI'm so glad I like came across
this.
But Emily Sunderberg, feed Meis her subsect, so yeah.
Speaker 2 (28:02):
Are there any career hacks or career cheat codes that
you feel like you've acquiredor mastered along the way that
you're like if folks knew thisearlier, they would do this or
they should consider doing this.
Speaker 1 (28:16):
I feel like I'm a little proud of, like my cold
email game.
It's you know iterations of it.
But there are two things Istill do if I'm trying to get in
front of somebody that I'mhaving difficulty getting in
touch with.
One is you know, sometimes yougo to a conference and you can't
make it to every singlebreakout session or every single
you know speech.
(28:36):
You know, either you can'tafford the ticket to go to those
or it was just there was aconflict in all the things you
want to go to, and so sometimeswhat I'll do is like, oh man, I
wish I could have gotten infront of that person.
I will go on LinkedIn, eventhough I think they might be
doing away with the hashtags,but I'll click the hashtag from
the conference and I will lookup that person, like what their,
(29:00):
how their panel went, what weresome of the takeaways, what
people are posting about it, andyou know I'll message them and
I'll be like hey, I saw thisconference, I saw that you spoke
.
I'm so sorry I missed it.
These are some of the things Itook away just from based on the
LinkedIn conversations about it.
It sounded impactful.
Do you mind if I do a follow-upwith you just to get the
information.
I didn't have a chance to getit and I'm so sorry it was
scheduled at this time and I wasin this room, but I promise I
(29:22):
was there just personalizing it.
I get a lot of cold messagesthat are just like hi, we have
things in common and we knowpeople in common.
Do you want to chat for 30minutes?
And I'm like, oh my God, I getthose like five a day.
There's no way I can just chatwith random people because they
feel like it Right, like tell mewhy, tell me what I can do for
you, tell me what you're tryingto get at specifically and I can
(29:44):
opt in or not.
So that's kind of worked for me.
And then I tell this to like mymentees all the time.
I'm a mentor with thisorganization called Gen Z VCs
for people who want to breakinto venture and are early in
their career.
A lot of people aren't going toturn down a speaking engagement
.
Right, that's free press forthem.
(30:13):
So say I did this when I was atStern.
I created a series of firesidechats with venture capitalists
in the specific industries Iwanted to work in with one of
our entrepreneurship centers andI moderated them and so my name
is now aligned with GPs offunds and so that allowed me to
have the conversation, to getinternships, to get in front of
(30:33):
them, to network with them, toget introductions.
So I would say, be thoughtfuland have something to offer and
not just say, hey, I want yourtime, just because I want it.
To say this is why I want yourtime, this is why I could feel
it was beneficial and I did myresearch before even reaching
out to you, so you don't evenhave to fill in the blanks.
I'm going to actually ask somekind of hard hitting questions
(30:56):
because I know who I'm talkingto and I know what I want to
talk about.
Speaker 2 (30:59):
These are some great cheat codes.
I appreciate that, and it alsogoes back to the networking
piece of your role being yourfavorite part.
It all comes together when yougive away the cheat code, so
that's helpful.
Thank you, yeah.
Is there anything else wehaven't discussed that the world
should know about?
Christian?
Speaker 1 (31:15):
I think I'm in a stage where I'm getting in touch
with my roots and allowing thatto kind of be shared outwardly.
So you know, not that I wasever like embarrassed by who I
was, but I just never talkedabout being Jamaican or being
the child of an immigrant.
And, depending on where yourfamily's from or you know what
you guys are going through, somefamilies ask you to assimilate
(31:38):
right, and so an example of thatis that my, the dialect of
Jamaica, is Patois, and myfather never spoke it in front
of me as a kid because he wantedme to speak proper English, and
you know not have any issueswith my pronunciation or you
know being treated a certain waybased on how I pronounce things
, and you know, I think I can'tspeak Patois today, which I wish
(31:59):
I could, and I actually, youknow, have like a text.
It's like an app that changesmy text back and forth from
Patois, just to like send myfriends who are also Jamaican,
and so I'm leaning into myheritage a little more.
That being said, so now whenit's Caribbean American Heritage
Month, I post about all of thepeople in the venture and
startup space who are ofCaribbean descent, just if you
(32:24):
want to follow them or learnmore about us.
I host a dinner party series forinvestors.
It wasn't Caribbean specific atfirst, but the more people I
talked in the space are like Ididn't know that about you.
That's really cool.
It's like huh, maybe we shouldhave like a Caribbean VC event.
So I'm hosting one coming upsoon with people that I've been
sharing about who I am and myjourney, which has been kind of
fun.
And then in Chicago, which youknow obviously doesn't have as
(32:46):
large a Korean population as theEast coast, I've had to go out
of my way to find great Jamaicanfood or make friends with my
same background and I have likea little crew now we have a
group chat and we go to moviesand we have dinner parties and
it's been a fun thing that Inever leaned into, but I am now
and it just makes you knowChicago feel a little more like
home.
It's not New Jersey or New York, but it's still a special place
(33:09):
and so that's been fun.
Speaker 2 (33:11):
Thank you for joining us on Career Cheat Code today.
I really appreciate your time.
Speaker 1 (33:14):
Yeah, thanks for having me.
Speaker 2 (33:15):
I hope you enjoyed this episode.
If you did and believe on themission we're on, please like,
rate and subscribe to thispodcast on whatever platform
you're using, and share thispodcast with your friends and
your networks.
Make sure you follow us onInstagram and LinkedIn at Career
Cheat Code and tell us peopleor careers you would like to see
highlighted.
See you next week with somemore cheat codes.
Peace.
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