February 18, 2025 • 39 mins
Dan Ahrens shares his journey from family influences to founding Left Lane Capital and raising a $630 million fund. He discusses the traits of great investors and offers advice for early career professionals, emphasizing the value of hustle and thinking like an owner. Dan explores evaluating investments, promoting from within, and operating efficiently. He provides insights on human-led sourcing in venture capital and overcoming career stagnation. The episode delves into identifying key traits in a team, starting a company in the current market, and balancing long-term and short-term thinking in investments. Dan reflects on past decisions and offers guidance for aspiring venture capitalists.
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Episode Transcript
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(00:00):
Raised $630,000,000 for that first fund.
What was your pitch?
The pitch was first and foremost, no.
You actually can build a huge business, and youcan do so in a way that is more reliable.
This is Dan Ahrens.
He runs a $2,000,000,000 investment firm in NewYork City that he started at just 29 years old.
I wanted to know what his secrets are.
So today, I had him here at our studio andasked him to teach me everything he knows about
(00:24):
investing.
What is the number one trait that makes a greatinvestor?
Curiosity.
There is a real advantage to knowing two timesmore than the next best investor.
For someone early in their career, what pieceof advice would you give them to get to a
position like you are in today?
The first thing, honestly, is
(00:45):
Dan, you're a beast.
You're the former vice president of a$90,000,000,000 investment firm.
And today, you run your own firm calledLeftLane Capital with over $2,000,000,000 in
assets under management.
For someone early in their career who might belistening to this, what piece of advice would
you give them to get to a position like you arein today?
(01:06):
I'd say it's really a couple things.
I'd say the first thing, honestly, is payattention to all of the little details, that
are going on around you.
I think as I think about my road to InsightPartners where I started my career in venture,
a number of steps along the way, I'd say eachone of those steps required me to really pay
(01:26):
attention to other people who previously werein my life and and who were able to to be
successful to understand what worked and whatdidn't.
I'll give one example from earlier on in in mylife.
I'm a venture capitalist now, but perhaps theearliest influence on me was one of my older
sisters.
So grew up in Saint Louis.
I had two older sisters, one of whom was nineyears older than me.
(01:48):
She's actually one of the world's leadingscientists and doctors specifically around
curing rare genetic diseases in small children.
So you look at that and you think, okay, whatdoes that have to do with anything that I'm
doing now?
Well, as I was growing up, I learned a coupleof different things from her.
I'd say the first thing really that I learnedwas just the level of conviction and self
(02:10):
belief it takes in order to do something that'sgenerally pretty highly improbable.
I'd say the second thing is just, frankly, hardwork and a complete lack of shyness.
Like, if you're especially if you're looking toget into venture or get into something that is
a competitive space, being willing to makeyourself the expert or the greatest expert that
(02:32):
you possibly can, learn everything around you,but then also reach out, get in front of
people, and just have, frankly, the theextroversion and hustle and effort to just make
it happen, I think, are probably the twobiggest things.
When you're paying attention to the details ofthe most successful people on the planet and
you study them, what are a few things thatyou've noticed that they all have in common?
(02:53):
Very surprisingly is a level of humility and anunderstanding of the importance of context and
the context you put yourself in relative to allof the things you're ultimately doing yourself.
I remember about a decade ago, I had my, myfinal round interviews at Insight Partners for
my first job in venture.
That point, I think Insight was on its eighthor its ninth fund.
(03:16):
They had proven themselves to be an institutionwith real staying power.
And I actually asked, managing partner, a mannamed Richard Wells was my last interview.
I asked him.
I was like, hey.
Why have you all been so successful?
And I expected to hear things around, oh, it'sbecause we look at it this way or we understand
this.
First thing he said was just, we ran we run agreat race, and we were super intentional about
(03:40):
the space that we wanted to play in.
And understanding that you as good or as strongor as smart as you think you are, minding your
context and actually actively managing thatcontext, be it the industry you're going after,
the problem you're trying to solve, the peopleyou're surrounding yourself with is incredibly
important.
And I think everybody that I talk to who's beensuper successful has really thought about it
(04:02):
that way.
The second thing that all of them have is acontinually renewable source of self belief.
You know, at this point, I've had the chance towork with almost a hundred different growth
investments, venture investments between mytime at Insight and and now my time at
Leftlane.
All of them, even and especially the those thathave gone on to very successful multibillion
(04:25):
dollar exits for twelve, eighteen, twenty fourmonths in each of those cases, there was a
point where we didn't know if the business wasultimately going to exist.
And the successful founders were the ones whowere able to find that belief not just for
themselves, but also for the entirety of theirteams and be able to instill that through an
organization.
So I think when you put those two thingstogether, those are two of the most common
(04:47):
themes, specifically within founders and peoplelooking to start companies that I've seen be
successful.
You mentioned hustle.
As much as it's talked about, I still thinkit's a little bit underrated.
You did what I'll I believe a lot more peopleshould do.
So instead of going to an MBA, you kinda justjumped right into it.
I think that if you wanna be successful asefficiently as possible, don't get an MBA.
(05:10):
Instead, I think you should learn from the mostsuccessful people in the world who are already
in the position that you want to be in.
And then go out, work for them, and take notesrelentlessly for two years and figure out what
do do they do differently, like you mentioned,that other people don't.
And then just reverse engineer what they dointo your own life and apply that.
And by the way, you don't end up with hundredsof thousands of dollars in debt along the way.
(05:35):
But what do you think about, an MBA and goingthrough that process?
So I understand the argument against an MBA,particularly when you are earlier on in your
career.
I I agree with the thesis that gettingpractical hands on experience to the extent
that you can, is ultimately going to trumpanything you're going to be able to learn in a
(05:57):
classroom.
And it also should, again, especially early inyour career, be available to you now that
there's more information available than everfor you to read, dig in on, make yourself an
expert, and then work to get yourself in frontof people who ultimately work with you.
I do think the MBA certainly has a place.
As I think about people who are mentors for me.
I can think of one person, right out of collegein in my BCG days.
(06:21):
He was actually a former army combat engineer.
And so he spent the first eight years of of hiscareer helping build bridges in Afghanistan.
And so for somebody like him coming back andbeing able to say, okay.
Now let me get the skills and let me spend twoyears of my life networking.
I think there's value to it.
But as you think about someone who's juststarting out, I would really if you wanna be in
business, really prioritize experience first.
And you decide to leave in
(06:43):
prioritize experience first.
And you decide to leave Insight to start yourown firm with your, with Harley and Vinny.
Why did you decide to leave Insight?
And what was so special about LeftLane when youfirst started and and still is that led you to
gain a competitive advantage against other VCfirms in the space?
Yeah.
So Harley, Vinny, and Jason, Schiedler, who whojoined us as well.
(07:05):
So I'd say the motivation behind it was a realconviction in the strategy that we were running
and a desire to, frankly, build somethingourselves.
So Insight Partners, for for those listeningwho may not know, really successful growth
equity, private equity, investment fundprimarily focused on enterprise software over
(07:27):
the last several decades.
So that's where, all of my partners and Istarted our careers, in in venture.
And Insight taught us a couple very importantthings.
I'd say, perhaps first and foremost, it wasbecoming an expert in your space and and on the
investment thesis that you wanted to run down.
Now for them, that was enterprise software, andthey started doing this in the mid to late
(07:49):
nineties.
It was an amazing choice, an amazing race, andand they've run it particularly well.
As I think about what our thesis has been overthe course of our careers, it's been a little
bit different.
Right?
Which is, you know, if enterprise software,which is an asset class that so much of the
industry has ultimately flocked to, It's been agreat asset class because of a couple things.
(08:11):
One, there have been technological tailwindsbehind it.
So you had, compute power move into the cloud,things move off premise.
You had more and more companies building on topof of these software solutions so that you
would end up with businesses who will becustomers of Salesforce for as long as they
exist.
Right?
When we looked at our space, we saw a differenttechnological tailwind and a much larger
(08:34):
opportunity.
So rather than focus on the, you know, couplehundred billion dollars a year of enterprise
software spend, we turned our eyes towards thenow $55,000,000,000,000 a year consumer market
and market of consumer spend in the Westernworld.
And we've seen a couple tailwinds that we thinkare actually even more transformational.
First and foremost, smartphone penetrationdating back from, you know, late two thousands
(09:00):
all the way through to to where we are today.
That enabled a complete transformation of theway that consumers use the Internet.
You know, it went from the place where you finda doctor's office, the place where you share
photos of your friends, to now it's actuallythe place you go to the doctor.
It's not where you find a tutor.
It's the place where you receive the tutoringservices.
(09:21):
So we saw this transformation where we thoughtInternet properties and things solving these
really lifelong problems for consumers wereboth going to be more available than ever
because of smartphone penetration.
And then also, they were going to be able tocapture more wallet share than ever because,
again, there was just way more economics thatwere actually moving through the platforms as
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opposed to something that was going offplatform.
So we saw this thesis.
We saw a market where everybody was reallyfocused in the venture world pretty purely on
enterprise software.
And so we thought there was an opportunity toto build an organization and a and a fund that
was just dedicated to working with founders tosolve these problems.
(10:05):
It's a the the journey for m one finance, oneof our first investments out of our our first
fund at left lane relative to an enterprisesoftware company is absolutely night and day.
And so if we we felt if we built a team, anetwork, resources, a thesis just around
understanding that that we were gonna be ableto stand out.
And when you started your first fund, youraised $630,000,000 for that first fund.
(10:29):
How many meetings did it take to get to that?
Somewhere between 1,502,000.
And what
was your pitch?
So the pitch the first part of the pitch wasreally exactly what I just laid out to you.
It wasn't so much selling people on us.
Although, at the time, I was 29.
The oldest of my partners was 30.
So there was an element of establishingcredibility.
(10:51):
The pitch was first and foremost, no.
You actually can build a huge business in inconsumer, and you can do so in a way that is
more reliable.
Because if you think about limited partners,LPs, the people who invest in in our funds,
they'd gone through this wave of socialnetworks, let's say, where one out of every end
social network going after a particular spacewas ultimately going to win.
(11:14):
They went through a wave of low repeat, lowretention d to c brands, mattress brands, for
example, which had astonishing growth, but thenyou had no repeat customers.
And so, ultimately, there was real volatility.
So the default assumption from so many peoplewas that you just can't do this in consumer.
Right?
Like, this enterprise software is the onlyplace you can run a sustainable venture
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playbook.
And so the pitch always started with that, withexplaining the fact that there is a difference
between good venture, investable consumer andconsumer that really isn't venture investable.
And that that thesis started with the samereason the folks at Insight loved enterprise
and enterprise software which we learned from,starts with retention.
(11:56):
It starts with the fact that if you backcompanies that customers will be around for
ten, fifteen, twenty years, this becomes themost important thing that they're using on a
regular basis.
They're going to stick around.
And, I mean, I we've seen it, right, over thelast half decade where we had people at home
for COVID, usage of so many different tools andutilities spiked.
You had, capital more available than everbefore.
(12:19):
You had that pull back a bit.
But if you look at a lot of the companies wework with, because these were the types of
things that you don't cut when times get hard,that you really are building your life on top
of, then all those consumers persisted.
The companies or many of those consumerspersisted.
The companies are still doing great because ofthat resilience and that reliability.
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So it was finding a way to both convince peoplethat that was a viable strategy and then, of
course, you know, convince people on a firsttime fund where we were going with the the
super ambitious.
We're raising trying to raise 500.
We ended up raising $6.30, but convincingpeople to to make a bet on four relatively
young people running an ambitious strategy.
(13:00):
You mentioned your age.
You're 29 years old.
The oldest of your partners was 30.
I've noticed a couple of things about the agedynamic as a founder.
I've noticed one, in podcasting or, I guess, inmy instance, being young is definitely
certainly helpful to opening up the door.
Yeah.
But on the contrary, in sales, I've noticedthis this actually can be more of a negative
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than a positive.
And the reason why is especially if you arebuilding out a premium service offering and a
premium product.
If you're trying to sell that offering about asimilar price to somebody who might be, like,
ten years older than you, People mightquestion, like, hey.
Why should I trust someone who's ten yearsyounger to actually do this?
For maybe founders who are also pretty youngtrying to combat that, what would you tell
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them?
Make sure you understand what you're talkingabout.
And then secondly, quickly adapt to thelanguage that's already used by the people that
you're trying to work with.
I think if you can, in the first minute of aconversation with somebody, if you can
establish credibility with them about subjectmatter expertise in the content that you know,
(14:08):
immediately, some of the age concerns vanish.
The first I mentioned I was a strategyconsultant.
First thing I did out of, out of college, firstproject I worked on was working with steel
manufacturing, where I was as a 22 year old whoknew absolutely nothing about steel
manufacturing.
I was working with people who'd been in thesteel industry for three, four decades.
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And my job was, how can we convince them to dox, y, and z and and sort of achieve this
strategic goal or identify it?
And it was I was bad at the beginning.
The first month, two months, it reallystruggled.
But once we were able to get to a point whereit was understanding that language,
understanding the lingo, knowing that the firsttwo minutes of a conversation with somebody,
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that vertical takeoff is so important, if youcan nail that, eventually, the the credibility
concerns melt away, and you're speaking withsomebody as a peer as opposed to somebody
you're trying to impress.
You mentioned the 1,500, meetings.
I presume you've gotten hundreds of rejectionsthrough that.
More than that.
Yeah.
How do you deal with rejection?
Keep going.
(15:10):
I think you get the rejection.
You get feedback.
First thing we do, evaluate the feedback.
Is it valid?
Is it not valid?
Are there is there some way we can objectionfield and and counter this or not?
If so, we're gonna change the pitch a littlebit.
We'll change the messaging.
We'll make sure we have additional materials tomake sure that people get this specific point
about what it is that we're doing.
(15:31):
And if not, you know what?
We're just gonna keep going.
I think that's one of the advantages, that Ihave frankly as a VC relative to somebody
starting a company is I've had the chance towork with so many different founders and see
such an extraordinary level of rejection thatfounders face as they as they start a company
or start a career.
It's the norm.
(15:52):
It's just what is going to happen the vastmajority of the time.
And so I think if you're gonna go startsomething knowing that's the case and how to
use it effectively, let it roll off and keepgoing, super important.
I was listening to one of your cofounder'sinterviews, Harley Miller, on '20 BC.
And he said that to be successful early on in afund, even if you're an associate, you have to
think like an owner.
(16:13):
How do you do that?
It's a
good question.
If you're thinking like an owner rather thanthinking about how can you know, a typical
thing we'll hear from somebody, you know,junior in venture.
How can I get a deal done?
How can I start building a track record?
That drives great hustle and great drive.
That's awesome.
But it's not just how can I get deals done?
It's how can I get the right deals done, andhow can I have my these earliest seeds that I
(16:36):
plant in the ground be an enormously positivepart of of the track record?
Because the things that we were able to raisefund one of of of left lane on primarily were
things that were done across the the group ofour careers when we were associates, right,
when we were sorted at that stage.
You've invested in some pretty successfulcompanies now, like m one finance, Spilt
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Rewards.
What do you look for in the right deals?
First and foremost, will this product becomepart of the operating system of a consumer's
life?
So we are relentless at evaluating thecustomer's relationship with the product.
We're looking for longevity.
We're often and this is more of kind of ourquantitative approach where we will almost
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every deal that we do, we will look at raw,anonymized, of course, but raw transaction
data.
So every transaction that that somebody's everdone.
We'll also look at usage data.
How often are you opening an app?
How often are you, you know, if it's a savingsapp, checking your savings?
How often are you thinking about that?
And we'll do surveys.
We'll do all of this to put together a holisticview of, hey.
(17:44):
Is this going to be a bedrock of somebody'slife?
Is it not gonna be a bedrock of somebody'slife?
And so that node is the first thing that we'rereally looking for.
Does that exist or does that not?
I think you'll hear different people who investin consumer approach things differently.
That really sits at the top for us.
And then, obviously, market, tailwinds,competitors, you'll sort of run everything
(18:05):
through.
But our thesis and our bet is that that node,that customer, product relationship is
something that was under misunderstood, underunderstood, underanalyzed, and that there's
real alpha if we're able to understand thatbetter.
And the other culture that you emphasizedpretty, diligently at left lane is to promote
from within.
What does that mean, and why is it so importantfor your team?
(18:27):
It's really difficult to think like an owner ifthere's absolutely if there's very little
chance or no belief that you can become one.
I think that's one piece of it.
The second piece of it is if we're going toinvest as heavily in our culture as we do,
super important to us that the people who joinus around the table as partners be people who
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came through the ranks and and sort of rosethrough that culture.
So to that extent, you know, everybody whoworks at Left Line has long term incentives
with the fund.
Right?
Has carry in the funds to make sure thatthey're fully aligned.
We absolutely practice what we preach.
One of our honestly, one of our proudest daysis we had our first partner promotion, with
Matt Miller joining us.
(19:08):
He, you know, he was one of the absolute firstpeople here at at left lane, started as a
senior associate, rose the ranks all the waythrough.
We've got an incredibly deep, talented team aswell where we're hopeful that, more people will
join us, but it's super important to us.
You've operated with a quite a bit of speed.
This is something that I've noticed has been aconsistent theme on our show.
(19:28):
I interviewed this guy, which you mightactually you might actually wanna speak to.
His name is Zach Yadeghari.
He's, 17.
He's got a consumer app called Kallai.
And what they do is they scan food with 93%accuracy.
It'll tell you, like, the calories andinformation and everything in in the meal.
They do about 12,000,000 in ARR in high school.
(19:49):
And, I asked him, why do you think you've beenso successful?
And he said, it distills down to one thing,because I operate with speed.
When I decide to take action on something,build out a feature, start a company, build a
product, I just do it.
And meanwhile, when our competitors decide thatthey might wanna do something similar, it took
(20:10):
them three months to decide whether or not theyshould do it, and we're three months ahead.
But I think there's the other side of it whereI think if you operate too fast, where you're
just doing things just because they pop in yourmind and you're like, okay.
Let me go do that now.
You actually act more reckless.
Is there a right balance that you can createwith acting fast, but also efficiently and
(20:31):
being intentional about the decisions you make?
It's a there's so many ways you could go withthe speed conversation.
I think to answer the question directly, thereabsolutely is, the right balance to solve.
Where I've seen founders we've worked withbuilding companies be successful with this, so
they have a north star.
The north star is usually oriented around theproblem that they're ultimately solving.
(20:52):
And so if they know, for example, I recentlyled investment to a company called Rev AI,
which is AI that helps body shops, collisionshops repair the computers in your car as well.
So if they know that the core problem statementis right now, you know, 80% of the time,
certain shops aren't able to do certain repairson on computers, which leads to a worse
(21:15):
experience for everybody.
That's the problem they're solving.
Then the product roadmap, let's figure out thebest possible way to actually go solve that
specific problem.
If that's where we think the most economicvalue lies and where our greatest ability to
grow is, then every piece of our productroadmap.
We may try, you know, x, option of doing thisor y option of doing this.
(21:35):
But if that's the North Star, let's solve forthat and oscillate within that.
We've seen a bit less success is where thatNorth Star starts to move around and and the
end problem that you're ultimately solving.
But the the point around speed and the Cal AIstory of, you know, I'm able to win because we
go fast, Every investment, I think, in in justabout any kind of firm that you're evaluating,
(21:57):
there's always a really common question, whichis, aren't the incumbents going to do this?
Or isn't Amazon gonna do this?
Isn't Apple gonna do this?
Or somebody going to do this?
I worked with some, you know, large companiesat BCG and saw attempts at large companies
innovating.
The fact that an exceptionally talented team,let's say, in fintech or wealth management, for
example, can build a significant portion of apersonal budgeting app in three months, test
(22:21):
it, try it, To even get access to engineeringresources at a large existing financial
institution, that might take a year.
And then it's system and then there so Igenuinely believe in kinda organizational in in
large organizations having an endemic slownessto them where it's just difficult to steer the
ship.
And I think that that's not just an advantagethat happened that a company enjoys when
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they're first starting out.
It is something that DNA wise, if you canmaintain it, is gonna give you an advantage
throughout the entire building process.
And on the investing side, when you're sittingdown looking at companies, you're looking at
companies in new and totally differentindustries quite frequently, which means every
two to eight weeks, you kinda have to becomelike a micro expert on that industry.
(23:06):
What's the framework that you go through tounderstand as much as you can about an industry
in a short and condensed period of time aspossible?
Start with the problem.
How big is it?
How painful is it at the customer level?
Look at the alternative solutions to theproblem.
Do I think this problem is going to be biggeror smaller in five years?
How well does this company solve that problem?
(23:26):
You know, one of the biggest draws of poorventure capital returns or biggest drivers of
poor venture capital returns is when you arelooking investing into things that look cool or
feel cool but don't have same power and don'thave that.
So being very problem centric when we're firsttrying to really understand a new space and and
get up to speed.
And you're also trying to spend you spend a lotof time trying to find under the radar
(23:47):
companies.
I think that's where a lot of the valuecreation can be found.
What do you do to find companies that are underthe radar, but also highly investable and great
opportunities?
The first and first and foremost is knowingwhat good looks like.
Especially at early stage of a company, what'ssomething that has a high probability of of
being good or is running a race that we thinkis ultimately good.
(24:10):
And so that's when some of the things I talkedabout earlier around our strategy works because
of high retention.
Right?
So if something we don't think something canhave a ten year customer relationship, we're
simply not going to back it.
So taking all the opportunities, running itfirst through that filter.
And then from there, having a combination of anincredible team.
I mean, we've got 24 people on our investmentteam whose job it is is to see every possible
(24:34):
angle and every possible company.
And I firmly believe we have a a wonderful databackbone that takes credit card data and all
these different data sources, runs it throughan AI engine, and helps find it.
I think when you're talking about therelationship that exists between a VC and a
founder, that that sourcing absolutely has tobe human led.
And so we've got an incredible team whose jobit is is to take all the signals and data that
(24:56):
we have, add value in initial conversationswith founders, build trust, and get to a point
where, you know, ideally before other peopleare seeing it, we're able to to get in front of
it.
And then I'd say the a big part of that aswell, just getting on a plane.
I think that's a huge part of our culture.
I I think back to partner Vinny got married acouple years ago in in Southern California.
(25:19):
And the Thursday before the Saturday wedding,one of our, we have a UK office.
One of our London team members found an awesomedeal in in Hamburg, Germany.
He also actually came over for Vinny's weddingin Southern California.
So Saturday is the wedding.
The Thursday before, we're in a meeting.
We see that this is potentially an incredibleopportunity.
We're like, alright.
(25:40):
That that Sunday, right after morning after thewedding, we hopped the flight to to Hamburg via
at least one connection, and had a four hourstanding meeting, quite literally standing
because the CEO honestly, I think it was a testto see if we would ask to sit down, but we held
through it, jet lagged, and all got through thefour hour standing meeting and then moved on.
Right?
I think there's a there's a real element ofthat that's just core to the culture.
(26:02):
Yeah.
I noticed that too because, last year, it was,like, during spring break.
I was, like, I saw a conference that JackAltman was speaking at in San Francisco.
I was, like, oh, I should I should go out thereand fly out there.
Keep in mind, I've probably never flown outanywhere outside of Florida when I was, like,
three or four years old in my life.
So my parents were pretty hesitant.
They're like, why?
(26:23):
You don't need to get on the plane.
I'm sure you could just email him.
And, like, no.
I gotta go out and and try to see if I couldstrike up a conversation with him.
I was walking to Chipotle to get lunch afterone of the speakers was done speaking, and I
see him coming out the back entrance.
So I just walk up to him, like, hey, Jack.
This is what I'm doing.
Super generous with this time.
Spent, like, three or four minutes talking tome.
(26:44):
Didn't have to do that.
Yeah.
And at the end, I'm like, hey.
We got the show.
We'd love to have you on.
He's like, yeah.
I got a baby coming up in a few months, butI'll do it after.
I think just having those types ofconversations and just getting on the plane,
taking the train, going, taking the meeting,responding to that email, I think can be those
micro differences and micro, I guess, decisionscan be the thing that makes the difference
(27:05):
between making it and not.
I love the hustle, by the way.
That's awesome.
But we I mean, it's it's beyond just sort ofthat initial thing of of winning a deal.
There's also, look, the journey of a startup,as I mentioned earlier, is just never linear.
Like, there's always going to be ups and downsand changes because it can take ten, twelve
years to go from an investment to an exit.
(27:27):
And so if the foundation of the relationship isbuilt on, hey.
No.
We worked super hard.
We came here face to face.
We went to Germany or The Czech Republic orwherever, and we sat down.
We had a meal.
When that trust is established from thebeginning, it makes the the tough conversations
that you're gonna have over a decade just mucheasier if that's the orientation from the get
(27:48):
go.
This is more general, but there are people inthe audience who might be listening to this who
are kinda following the things that you'vementioned.
Maybe they're spending a lot of time grinding,hustling, getting on the plane, paying
attention to all the micro details, but theystill feel stuck.
How can someone who might be in that positionget unstuck?
There's two types of stuck.
There's short term stuck and long term stuck.
(28:11):
Short term stuck is maybe cheesy guys.
Get outside.
Go for a run.
Go if you're in a city, go to a differentneighborhood you don't normally spend time in.
Maybe don't bring your phone.
Don't look at it.
Just remove yourself from the problem thatyou're ultimately trying to solve.
Get some different experience or perspectiveeven if it's only for a few minutes.
(28:32):
For me, it's running.
I go over the the holidays.
I was working on a particular problem.
I I I live primarily in Chicago.
I went for a run.
It was 15 degrees outside.
I didn't care about the weather.
I responded and helped solve the problem afterthat.
I'd say more more seriously and more long term.
If you're feeling stuck, take a second andevaluate, like, what part of this do you feel
(28:53):
stuck on?
Is it is it a market and or problem issue?
In other words, is the track simply not longenough to run the race that you want to run, or
is it too cluttered to run the race that youwanna run?
Or are you feeling like you have somelimitation that you can identify to say, hey.
I'm not able to do this for x y z reason inwhich upskill.
(29:13):
I think it's a matter of, really, for thoselonger term conversations, thinking about, is
it there is it external?
Is it internal?
And then from there, working to to diagnose it.
I think that's a really good point.
And throughout your time investing, you've beeninvesting for nearly a decade now.
What is the number one trait that makes a greatinvestor?
Yeah.
(29:33):
Curiosity.
Curiosity.
I think that you need to when you're to yourpoint, doing these two to eight week micros you
know, sprints to become micro experts in agiven field, there is there is a real advantage
to knowing two times more than the next bestinvestor knows or the next best person knows.
(29:56):
And so getting to a point where you have thisdeep endemic curiosity where you see a problem
being solved, you need to understand where itis.
That's gonna help you find better deals, winbetter deals.
Importantly, you know, people VC, we talk a lotabout doing the investment.
As you're you know, I'm involved I've beeninvolved with now 20 plus boards over the
course of my career.
As you're a board member to and partner tofounders, that curiosity alongside of them is
(30:19):
also able to make you just a much betterthought partner.
And you're trying to become the best consumerinvestor and the best in your space.
To do that, you also need the best team.
How do you evaluate and distinguish a playersbetween b players and c players?
What what is so unique about them that you'reable to see early on?
(30:39):
Exactly why somebody is an a player, the spikethat they have, that can differ.
We have some folks who are exceptional atnetworking.
So they're able to meet everybody.
They become a gravitational pull in this space.
We have some folks who are exceptional one onone with founders, who are able to build
trusted relationships, some who justanalytically can see things ultimately in
(31:02):
different ways.
The underlying, commonalities that existbetween all of them is an ownership mentality.
So really caring about what they do, thinkingabout the big picture, absolute just hunger and
drive and continuing to push through things,and then empathy, honestly, and an
(31:23):
understanding for the people that they'reworking with.
So those three things underlie each of it, andthen you have the specific skills.
And so we'll we work with people.
You know, I think we're very intentional whenwe hire people around the goal is, hey.
We want you to become a partner here.
That's that's the goal that we have.
So we'll work with people very explicitly on,hey.
We need to work on this, or you did a great jobhere.
Work on that.
But those are some of the traits that we seereally distinguish the a players from the from
(31:47):
the b players.
And we've talked a little bit about thecompanies that you've invested in over at
Leftlane.
If you had to start a company today, right now,what space would it be in and why?
That's a great question.
I so for me, the thing I'm probably mostinterested in right now is the intersection
between personal finance and AI.
(32:08):
If you look at a lot of the deals that I'vedone or or worked on, just this idea of saving
families and households money and helpingpeople start businesses, finance businesses,
and run businesses.
Those are two of the themes that I think arekind of the the back room the backbone of my
career as an investor so far.
(32:28):
And when I look at what we've solved so far,one, I think the issue of, okay, can,
consumers, can small businesses get access tofinancial services?
Simply bringing them online was a monstrousstep.
Right?
And I think we've seen a lot of the benefitsthere.
As I look at the limitations, though, of onlinebut done by you, I think they're really clear.
(32:52):
Right now, there is so much information thatconsumers just don't know, unstructured
information that consumers, small businessowners don't know, don't have the time to know.
Everyone else has has other things that theyneed to do.
And the second, the process of actually usingthis information to do something with it is
extraordinarily opaque.
(33:12):
Like, I I'm a cofounder of a $2,000,000,000financial institution and bought a house
recently, there were huge swaths of it thatseemed esoteric, super complicated.
Right?
Both of those problems seem absolutely tailormade for for for AI to step in and and be able
to make it easier for folks and sort sort oftake us to the next generation of that.
(33:33):
I've seen the beginnings of some companies, Ithink, are interesting, but I think there's a
decade long plus, tailwind behind that that'sgonna just, frankly, improve outcomes for
everybody involved.
And we have a couple of closing questions thatwe like to wrap each interview up with.
One is, if I slid you over a phone and youcould call your 20 year old self Yeah.
(33:54):
Would you call?
And if so, what would you say?
My 20 year old self would be really freaked outif you gotta call for somebody.
No.
I so it's a good question.
I would call my 20 year old self.
I think the main thing that I would push thatperson to do is to just have far less fear or
(34:16):
concern of the downside of interactions andconversations.
Naturally, I'm a somewhat introverted person.
And so I think if I could go back and just say,hey.
Look.
No.
Go have that conversation.
Right?
Like, go get in front of that person.
Take that initial step.
I think the earlier you can start to do that,the network effects in your life are just
exponential and they compound.
So I would really push people in thatdirection.
(34:37):
And what's one rule that you live by that mostpeople don't?
One rule I live by that most people don't.
It's the first time I really have to stop andand think about something.
Probably the biggest thing within venture attimes, there can be a trade off between short
(34:57):
term outcomes, short term success, and thenlong term reputationally.
Right?
Like, what are you ultimately working towardsand building towards?
I think one of the things I try to focus on isunderstanding that our goal and our ambition at
LeftLion is to be successful for decades.
Right?
And so when that's your orientation and that'swhat you're pushing on, then the way that you
(35:19):
interact with founders, the way that youinteract with other investors.
You try to have that long term orientation.
I think we emphasize that.
I think you'll hear examples of other folks inthe industry maybe not necessarily doing that,
and that's one of the things we try to push on.
One interesting answer I'll give you to that,question was also Zach.
I asked him the same thing, and he said hewants to constantly reinforce that he has full
(35:41):
control on his life.
And here's what he mean by means by that.
When he got off the train he lives in LongIsland.
When he got off the train from Long Island toNew York to the studio, there are a few
different doors that he could go through.
The shortest one is what or the one closest tothe train is one pretty much everybody was
going into.
Made the most sense, most logical, etcetera.
(36:02):
But he thought, hey.
If my life's a simulation, I'll walk throughthat door.
But I wanna reinforce that I'm not in asimulation.
So I'm gonna go to the door all the way on theleft just because I can.
And he does this, like, all the time.
He'll make, like, micro decisions during theday.
Maybe instead of taking the shortest path to adestination, he'll spend an extra three minutes
walking a totally different block that wouldtake four or five minutes longer just because
(36:26):
he wants to reinforce that he has full controlon his life.
So that, I thought, was a pretty interestingway to think about it.
So when I was younger, I actually would gothrough a somewhat similar exercise of thinking
about, okay, well, probabilistically what pathshould I do and and was also somewhat focused
on that.
Then I had a kid, and I realized that I havevery little control over certain parts of
(36:50):
things.
It went out the window when my son startedwalking and decided to try to throw himself off
the back of my couch several times.
Then you gotta be logical and be like, alright.
I I should probably do something here.
Right?
That that's when I realized, like, seeing achild go through a fascination of simply
causing effects in life makes you understandthat you really need to be prepared to stop the
(37:10):
cause of various effects, come hell or highwater.
And to wrap it up here, what's one piece ofadvice you would give to somebody who's
listening right now who seems who has seen whatyou've done and, also wants to be able to
accomplish something similar?
With venture capital, the name of the game isfinding deals.
And so if you want to get into venture capital,act like you have the job now.
(37:31):
I think that's a cliche that people use, butwe've hired multiple people who got a foot in
the door simply by sending us deals or sendingus ideas, and ultimately getting in front of
us.
And so that is for VC, it's simple and superdifficult.
Get in front of great founders and bring usdeals.
Yeah.
And Jason Schuman from primary has a veryinteresting story along that path as well.
(37:53):
He started a shoe business in college at UMiami.
It didn't end up working out, but he moved outto Boston.
And, he's like, hey.
This venture capital thing seems prettyinteresting, but, like, I don't know how to get
a job in it.
So he would start sending deals for free.
This is before you could, you know, getcommissioned or or be be a scout for a firm.
He would send deals to VC firms in Boston forfree.
(38:16):
But, you know, he still had to pay the bills,so he'd drive for Uber at night.
And that's how he was able to get his first jobin ventures because one of his passengers was
actually a VC and was like, hey.
You you should probably we should probablytalk.
Super interesting path.
But I've noticed that one of the things he'stold me and I've always kept in the back of my
mind is if you can do the job before you getthe job, then you can get the job.
(38:38):
A %.
That's absolutely the right orientation,particularly when it comes to to venture.
Well, I think that's a great way to end it.
Thanks, Dan, for taking the time to join theshow.
I appreciate it.
And if anyone's a founder, especially inconsumer or in any of the areas that Leftlane
invests in, feel free to take a look at theirwebsite in the episode description down below.
And thanks for joining.
Thanks, Simon.
Appreciate it.
Raised $630,000,000 for that first fund.
What was your pitch?
The pitch was first and foremost, no.
You actually can build a huge business, and youcan do so in a way that is more reliable.
This is Dan Ahrens.
He runs a $2,000,000,000 investment firm in NewYork City that he started at just 29 years old.
I wanted to know what his secrets are.
So today, I had him here at our studio andasked him to teach me everything he knows about
(00:24):
investing.
What is the number one trait that makes a greatinvestor?
Curiosity.
There is a real advantage to knowing two timesmore than the next best investor.
For someone early in their career, what pieceof advice would you give them to get to a
position like you are in today?
The first thing, honestly, is
(00:45):
Dan, you're a beast.
You're the former vice president of a$90,000,000,000 investment firm.
And today, you run your own firm calledLeftLane Capital with over $2,000,000,000 in
assets under management.
For someone early in their career who might belistening to this, what piece of advice would
you give them to get to a position like you arein today?
(01:06):
I'd say it's really a couple things.
I'd say the first thing, honestly, is payattention to all of the little details, that
are going on around you.
I think as I think about my road to InsightPartners where I started my career in venture,
a number of steps along the way, I'd say eachone of those steps required me to really pay
(01:26):
attention to other people who previously werein my life and and who were able to to be
successful to understand what worked and whatdidn't.
I'll give one example from earlier on in in mylife.
I'm a venture capitalist now, but perhaps theearliest influence on me was one of my older
sisters.
So grew up in Saint Louis.
I had two older sisters, one of whom was nineyears older than me.
(01:48):
She's actually one of the world's leadingscientists and doctors specifically around
curing rare genetic diseases in small children.
So you look at that and you think, okay, whatdoes that have to do with anything that I'm
doing now?
Well, as I was growing up, I learned a coupleof different things from her.
I'd say the first thing really that I learnedwas just the level of conviction and self
(02:10):
belief it takes in order to do something that'sgenerally pretty highly improbable.
I'd say the second thing is just, frankly, hardwork and a complete lack of shyness.
Like, if you're especially if you're looking toget into venture or get into something that is
a competitive space, being willing to makeyourself the expert or the greatest expert that
(02:32):
you possibly can, learn everything around you,but then also reach out, get in front of
people, and just have, frankly, the theextroversion and hustle and effort to just make
it happen, I think, are probably the twobiggest things.
When you're paying attention to the details ofthe most successful people on the planet and
you study them, what are a few things thatyou've noticed that they all have in common?
(02:53):
Very surprisingly is a level of humility and anunderstanding of the importance of context and
the context you put yourself in relative to allof the things you're ultimately doing yourself.
I remember about a decade ago, I had my, myfinal round interviews at Insight Partners for
my first job in venture.
That point, I think Insight was on its eighthor its ninth fund.
(03:16):
They had proven themselves to be an institutionwith real staying power.
And I actually asked, managing partner, a mannamed Richard Wells was my last interview.
I asked him.
I was like, hey.
Why have you all been so successful?
And I expected to hear things around, oh, it'sbecause we look at it this way or we understand
this.
First thing he said was just, we ran we run agreat race, and we were super intentional about
(03:40):
the space that we wanted to play in.
And understanding that you as good or as strongor as smart as you think you are, minding your
context and actually actively managing thatcontext, be it the industry you're going after,
the problem you're trying to solve, the peopleyou're surrounding yourself with is incredibly
important.
And I think everybody that I talk to who's beensuper successful has really thought about it
(04:02):
that way.
The second thing that all of them have is acontinually renewable source of self belief.
You know, at this point, I've had the chance towork with almost a hundred different growth
investments, venture investments between mytime at Insight and and now my time at
Leftlane.
All of them, even and especially the those thathave gone on to very successful multibillion
(04:25):
dollar exits for twelve, eighteen, twenty fourmonths in each of those cases, there was a
point where we didn't know if the business wasultimately going to exist.
And the successful founders were the ones whowere able to find that belief not just for
themselves, but also for the entirety of theirteams and be able to instill that through an
organization.
So I think when you put those two thingstogether, those are two of the most common
(04:47):
themes, specifically within founders and peoplelooking to start companies that I've seen be
successful.
You mentioned hustle.
As much as it's talked about, I still thinkit's a little bit underrated.
You did what I'll I believe a lot more peopleshould do.
So instead of going to an MBA, you kinda justjumped right into it.
I think that if you wanna be successful asefficiently as possible, don't get an MBA.
(05:10):
Instead, I think you should learn from the mostsuccessful people in the world who are already
in the position that you want to be in.
And then go out, work for them, and take notesrelentlessly for two years and figure out what
do do they do differently, like you mentioned,that other people don't.
And then just reverse engineer what they dointo your own life and apply that.
And by the way, you don't end up with hundredsof thousands of dollars in debt along the way.
(05:35):
But what do you think about, an MBA and goingthrough that process?
So I understand the argument against an MBA,particularly when you are earlier on in your
career.
I I agree with the thesis that gettingpractical hands on experience to the extent
that you can, is ultimately going to trumpanything you're going to be able to learn in a
(05:57):
classroom.
And it also should, again, especially early inyour career, be available to you now that
there's more information available than everfor you to read, dig in on, make yourself an
expert, and then work to get yourself in frontof people who ultimately work with you.
I do think the MBA certainly has a place.
As I think about people who are mentors for me.
I can think of one person, right out of collegein in my BCG days.
(06:21):
He was actually a former army combat engineer.
And so he spent the first eight years of of hiscareer helping build bridges in Afghanistan.
And so for somebody like him coming back andbeing able to say, okay.
Now let me get the skills and let me spend twoyears of my life networking.
I think there's value to it.
But as you think about someone who's juststarting out, I would really if you wanna be in
business, really prioritize experience first.
And you decide to leave in
(06:43):
prioritize experience first.
And you decide to leave Insight to start yourown firm with your, with Harley and Vinny.
Why did you decide to leave Insight?
And what was so special about LeftLane when youfirst started and and still is that led you to
gain a competitive advantage against other VCfirms in the space?
Yeah.
So Harley, Vinny, and Jason, Schiedler, who whojoined us as well.
(07:05):
So I'd say the motivation behind it was a realconviction in the strategy that we were running
and a desire to, frankly, build somethingourselves.
So Insight Partners, for for those listeningwho may not know, really successful growth
equity, private equity, investment fundprimarily focused on enterprise software over
(07:27):
the last several decades.
So that's where, all of my partners and Istarted our careers, in in venture.
And Insight taught us a couple very importantthings.
I'd say, perhaps first and foremost, it wasbecoming an expert in your space and and on the
investment thesis that you wanted to run down.
Now for them, that was enterprise software, andthey started doing this in the mid to late
(07:49):
nineties.
It was an amazing choice, an amazing race, andand they've run it particularly well.
As I think about what our thesis has been overthe course of our careers, it's been a little
bit different.
Right?
Which is, you know, if enterprise software,which is an asset class that so much of the
industry has ultimately flocked to, It's been agreat asset class because of a couple things.
(08:11):
One, there have been technological tailwindsbehind it.
So you had, compute power move into the cloud,things move off premise.
You had more and more companies building on topof of these software solutions so that you
would end up with businesses who will becustomers of Salesforce for as long as they
exist.
Right?
When we looked at our space, we saw a differenttechnological tailwind and a much larger
(08:34):
opportunity.
So rather than focus on the, you know, couplehundred billion dollars a year of enterprise
software spend, we turned our eyes towards thenow $55,000,000,000,000 a year consumer market
and market of consumer spend in the Westernworld.
And we've seen a couple tailwinds that we thinkare actually even more transformational.
First and foremost, smartphone penetrationdating back from, you know, late two thousands
(09:00):
all the way through to to where we are today.
That enabled a complete transformation of theway that consumers use the Internet.
You know, it went from the place where you finda doctor's office, the place where you share
photos of your friends, to now it's actuallythe place you go to the doctor.
It's not where you find a tutor.
It's the place where you receive the tutoringservices.
(09:21):
So we saw this transformation where we thoughtInternet properties and things solving these
really lifelong problems for consumers wereboth going to be more available than ever
because of smartphone penetration.
And then also, they were going to be able tocapture more wallet share than ever because,
again, there was just way more economics thatwere actually moving through the platforms as
(09:43):
opposed to something that was going offplatform.
So we saw this thesis.
We saw a market where everybody was reallyfocused in the venture world pretty purely on
enterprise software.
And so we thought there was an opportunity toto build an organization and a and a fund that
was just dedicated to working with founders tosolve these problems.
(10:05):
It's a the the journey for m one finance, oneof our first investments out of our our first
fund at left lane relative to an enterprisesoftware company is absolutely night and day.
And so if we we felt if we built a team, anetwork, resources, a thesis just around
understanding that that we were gonna be ableto stand out.
And when you started your first fund, youraised $630,000,000 for that first fund.
(10:29):
How many meetings did it take to get to that?
Somewhere between 1,502,000.
And what
was your pitch?
So the pitch the first part of the pitch wasreally exactly what I just laid out to you.
It wasn't so much selling people on us.
Although, at the time, I was 29.
The oldest of my partners was 30.
So there was an element of establishingcredibility.
(10:51):
The pitch was first and foremost, no.
You actually can build a huge business in inconsumer, and you can do so in a way that is
more reliable.
Because if you think about limited partners,LPs, the people who invest in in our funds,
they'd gone through this wave of socialnetworks, let's say, where one out of every end
social network going after a particular spacewas ultimately going to win.
(11:14):
They went through a wave of low repeat, lowretention d to c brands, mattress brands, for
example, which had astonishing growth, but thenyou had no repeat customers.
And so, ultimately, there was real volatility.
So the default assumption from so many peoplewas that you just can't do this in consumer.
Right?
Like, this enterprise software is the onlyplace you can run a sustainable venture
(11:35):
playbook.
And so the pitch always started with that, withexplaining the fact that there is a difference
between good venture, investable consumer andconsumer that really isn't venture investable.
And that that thesis started with the samereason the folks at Insight loved enterprise
and enterprise software which we learned from,starts with retention.
(11:56):
It starts with the fact that if you backcompanies that customers will be around for
ten, fifteen, twenty years, this becomes themost important thing that they're using on a
regular basis.
They're going to stick around.
And, I mean, I we've seen it, right, over thelast half decade where we had people at home
for COVID, usage of so many different tools andutilities spiked.
You had, capital more available than everbefore.
(12:19):
You had that pull back a bit.
But if you look at a lot of the companies wework with, because these were the types of
things that you don't cut when times get hard,that you really are building your life on top
of, then all those consumers persisted.
The companies or many of those consumerspersisted.
The companies are still doing great because ofthat resilience and that reliability.
(12:40):
So it was finding a way to both convince peoplethat that was a viable strategy and then, of
course, you know, convince people on a firsttime fund where we were going with the the
super ambitious.
We're raising trying to raise 500.
We ended up raising $6.30, but convincingpeople to to make a bet on four relatively
young people running an ambitious strategy.
(13:00):
You mentioned your age.
You're 29 years old.
The oldest of your partners was 30.
I've noticed a couple of things about the agedynamic as a founder.
I've noticed one, in podcasting or, I guess, inmy instance, being young is definitely
certainly helpful to opening up the door.
Yeah.
But on the contrary, in sales, I've noticedthis this actually can be more of a negative
(13:21):
than a positive.
And the reason why is especially if you arebuilding out a premium service offering and a
premium product.
If you're trying to sell that offering about asimilar price to somebody who might be, like,
ten years older than you, People mightquestion, like, hey.
Why should I trust someone who's ten yearsyounger to actually do this?
For maybe founders who are also pretty youngtrying to combat that, what would you tell
(13:45):
them?
Make sure you understand what you're talkingabout.
And then secondly, quickly adapt to thelanguage that's already used by the people that
you're trying to work with.
I think if you can, in the first minute of aconversation with somebody, if you can
establish credibility with them about subjectmatter expertise in the content that you know,
(14:08):
immediately, some of the age concerns vanish.
The first I mentioned I was a strategyconsultant.
First thing I did out of, out of college, firstproject I worked on was working with steel
manufacturing, where I was as a 22 year old whoknew absolutely nothing about steel
manufacturing.
I was working with people who'd been in thesteel industry for three, four decades.
(14:29):
And my job was, how can we convince them to dox, y, and z and and sort of achieve this
strategic goal or identify it?
And it was I was bad at the beginning.
The first month, two months, it reallystruggled.
But once we were able to get to a point whereit was understanding that language,
understanding the lingo, knowing that the firsttwo minutes of a conversation with somebody,
(14:49):
that vertical takeoff is so important, if youcan nail that, eventually, the the credibility
concerns melt away, and you're speaking withsomebody as a peer as opposed to somebody
you're trying to impress.
You mentioned the 1,500, meetings.
I presume you've gotten hundreds of rejectionsthrough that.
More than that.
Yeah.
How do you deal with rejection?
Keep going.
(15:10):
I think you get the rejection.
You get feedback.
First thing we do, evaluate the feedback.
Is it valid?
Is it not valid?
Are there is there some way we can objectionfield and and counter this or not?
If so, we're gonna change the pitch a littlebit.
We'll change the messaging.
We'll make sure we have additional materials tomake sure that people get this specific point
about what it is that we're doing.
(15:31):
And if not, you know what?
We're just gonna keep going.
I think that's one of the advantages, that Ihave frankly as a VC relative to somebody
starting a company is I've had the chance towork with so many different founders and see
such an extraordinary level of rejection thatfounders face as they as they start a company
or start a career.
It's the norm.
(15:52):
It's just what is going to happen the vastmajority of the time.
And so I think if you're gonna go startsomething knowing that's the case and how to
use it effectively, let it roll off and keepgoing, super important.
I was listening to one of your cofounder'sinterviews, Harley Miller, on '20 BC.
And he said that to be successful early on in afund, even if you're an associate, you have to
think like an owner.
(16:13):
How do you do that?
It's a
good question.
If you're thinking like an owner rather thanthinking about how can you know, a typical
thing we'll hear from somebody, you know,junior in venture.
How can I get a deal done?
How can I start building a track record?
That drives great hustle and great drive.
That's awesome.
But it's not just how can I get deals done?
It's how can I get the right deals done, andhow can I have my these earliest seeds that I
(16:36):
plant in the ground be an enormously positivepart of of the track record?
Because the things that we were able to raisefund one of of of left lane on primarily were
things that were done across the the group ofour careers when we were associates, right,
when we were sorted at that stage.
You've invested in some pretty successfulcompanies now, like m one finance, Spilt
(16:58):
Rewards.
What do you look for in the right deals?
First and foremost, will this product becomepart of the operating system of a consumer's
life?
So we are relentless at evaluating thecustomer's relationship with the product.
We're looking for longevity.
We're often and this is more of kind of ourquantitative approach where we will almost
(17:22):
every deal that we do, we will look at raw,anonymized, of course, but raw transaction
data.
So every transaction that that somebody's everdone.
We'll also look at usage data.
How often are you opening an app?
How often are you, you know, if it's a savingsapp, checking your savings?
How often are you thinking about that?
And we'll do surveys.
We'll do all of this to put together a holisticview of, hey.
(17:44):
Is this going to be a bedrock of somebody'slife?
Is it not gonna be a bedrock of somebody'slife?
And so that node is the first thing that we'rereally looking for.
Does that exist or does that not?
I think you'll hear different people who investin consumer approach things differently.
That really sits at the top for us.
And then, obviously, market, tailwinds,competitors, you'll sort of run everything
(18:05):
through.
But our thesis and our bet is that that node,that customer, product relationship is
something that was under misunderstood, underunderstood, underanalyzed, and that there's
real alpha if we're able to understand thatbetter.
And the other culture that you emphasizedpretty, diligently at left lane is to promote
from within.
What does that mean, and why is it so importantfor your team?
(18:27):
It's really difficult to think like an owner ifthere's absolutely if there's very little
chance or no belief that you can become one.
I think that's one piece of it.
The second piece of it is if we're going toinvest as heavily in our culture as we do,
super important to us that the people who joinus around the table as partners be people who
(18:47):
came through the ranks and and sort of rosethrough that culture.
So to that extent, you know, everybody whoworks at Left Line has long term incentives
with the fund.
Right?
Has carry in the funds to make sure thatthey're fully aligned.
We absolutely practice what we preach.
One of our honestly, one of our proudest daysis we had our first partner promotion, with
Matt Miller joining us.
(19:08):
He, you know, he was one of the absolute firstpeople here at at left lane, started as a
senior associate, rose the ranks all the waythrough.
We've got an incredibly deep, talented team aswell where we're hopeful that, more people will
join us, but it's super important to us.
You've operated with a quite a bit of speed.
This is something that I've noticed has been aconsistent theme on our show.
(19:28):
I interviewed this guy, which you mightactually you might actually wanna speak to.
His name is Zach Yadeghari.
He's, 17.
He's got a consumer app called Kallai.
And what they do is they scan food with 93%accuracy.
It'll tell you, like, the calories andinformation and everything in in the meal.
They do about 12,000,000 in ARR in high school.
(19:49):
And, I asked him, why do you think you've beenso successful?
And he said, it distills down to one thing,because I operate with speed.
When I decide to take action on something,build out a feature, start a company, build a
product, I just do it.
And meanwhile, when our competitors decide thatthey might wanna do something similar, it took
(20:10):
them three months to decide whether or not theyshould do it, and we're three months ahead.
But I think there's the other side of it whereI think if you operate too fast, where you're
just doing things just because they pop in yourmind and you're like, okay.
Let me go do that now.
You actually act more reckless.
Is there a right balance that you can createwith acting fast, but also efficiently and
(20:31):
being intentional about the decisions you make?
It's a there's so many ways you could go withthe speed conversation.
I think to answer the question directly, thereabsolutely is, the right balance to solve.
Where I've seen founders we've worked withbuilding companies be successful with this, so
they have a north star.
The north star is usually oriented around theproblem that they're ultimately solving.
(20:52):
And so if they know, for example, I recentlyled investment to a company called Rev AI,
which is AI that helps body shops, collisionshops repair the computers in your car as well.
So if they know that the core problem statementis right now, you know, 80% of the time,
certain shops aren't able to do certain repairson on computers, which leads to a worse
(21:15):
experience for everybody.
That's the problem they're solving.
Then the product roadmap, let's figure out thebest possible way to actually go solve that
specific problem.
If that's where we think the most economicvalue lies and where our greatest ability to
grow is, then every piece of our productroadmap.
We may try, you know, x, option of doing thisor y option of doing this.
(21:35):
But if that's the North Star, let's solve forthat and oscillate within that.
We've seen a bit less success is where thatNorth Star starts to move around and and the
end problem that you're ultimately solving.
But the the point around speed and the Cal AIstory of, you know, I'm able to win because we
go fast, Every investment, I think, in in justabout any kind of firm that you're evaluating,
(21:57):
there's always a really common question, whichis, aren't the incumbents going to do this?
Or isn't Amazon gonna do this?
Isn't Apple gonna do this?
Or somebody going to do this?
I worked with some, you know, large companiesat BCG and saw attempts at large companies
innovating.
The fact that an exceptionally talented team,let's say, in fintech or wealth management, for
example, can build a significant portion of apersonal budgeting app in three months, test
(22:21):
it, try it, To even get access to engineeringresources at a large existing financial
institution, that might take a year.
And then it's system and then there so Igenuinely believe in kinda organizational in in
large organizations having an endemic slownessto them where it's just difficult to steer the
ship.
And I think that that's not just an advantagethat happened that a company enjoys when
(22:45):
they're first starting out.
It is something that DNA wise, if you canmaintain it, is gonna give you an advantage
throughout the entire building process.
And on the investing side, when you're sittingdown looking at companies, you're looking at
companies in new and totally differentindustries quite frequently, which means every
two to eight weeks, you kinda have to becomelike a micro expert on that industry.
(23:06):
What's the framework that you go through tounderstand as much as you can about an industry
in a short and condensed period of time aspossible?
Start with the problem.
How big is it?
How painful is it at the customer level?
Look at the alternative solutions to theproblem.
Do I think this problem is going to be biggeror smaller in five years?
How well does this company solve that problem?
(23:26):
You know, one of the biggest draws of poorventure capital returns or biggest drivers of
poor venture capital returns is when you arelooking investing into things that look cool or
feel cool but don't have same power and don'thave that.
So being very problem centric when we're firsttrying to really understand a new space and and
get up to speed.
And you're also trying to spend you spend a lotof time trying to find under the radar
(23:47):
companies.
I think that's where a lot of the valuecreation can be found.
What do you do to find companies that are underthe radar, but also highly investable and great
opportunities?
The first and first and foremost is knowingwhat good looks like.
Especially at early stage of a company, what'ssomething that has a high probability of of
being good or is running a race that we thinkis ultimately good.
(24:10):
And so that's when some of the things I talkedabout earlier around our strategy works because
of high retention.
Right?
So if something we don't think something canhave a ten year customer relationship, we're
simply not going to back it.
So taking all the opportunities, running itfirst through that filter.
And then from there, having a combination of anincredible team.
I mean, we've got 24 people on our investmentteam whose job it is is to see every possible
(24:34):
angle and every possible company.
And I firmly believe we have a a wonderful databackbone that takes credit card data and all
these different data sources, runs it throughan AI engine, and helps find it.
I think when you're talking about therelationship that exists between a VC and a
founder, that that sourcing absolutely has tobe human led.
And so we've got an incredible team whose jobit is is to take all the signals and data that
(24:56):
we have, add value in initial conversationswith founders, build trust, and get to a point
where, you know, ideally before other peopleare seeing it, we're able to to get in front of
it.
And then I'd say the a big part of that aswell, just getting on a plane.
I think that's a huge part of our culture.
I I think back to partner Vinny got married acouple years ago in in Southern California.
(25:19):
And the Thursday before the Saturday wedding,one of our, we have a UK office.
One of our London team members found an awesomedeal in in Hamburg, Germany.
He also actually came over for Vinny's weddingin Southern California.
So Saturday is the wedding.
The Thursday before, we're in a meeting.
We see that this is potentially an incredibleopportunity.
We're like, alright.
(25:40):
That that Sunday, right after morning after thewedding, we hopped the flight to to Hamburg via
at least one connection, and had a four hourstanding meeting, quite literally standing
because the CEO honestly, I think it was a testto see if we would ask to sit down, but we held
through it, jet lagged, and all got through thefour hour standing meeting and then moved on.
Right?
I think there's a there's a real element ofthat that's just core to the culture.
(26:02):
Yeah.
I noticed that too because, last year, it was,like, during spring break.
I was, like, I saw a conference that JackAltman was speaking at in San Francisco.
I was, like, oh, I should I should go out thereand fly out there.
Keep in mind, I've probably never flown outanywhere outside of Florida when I was, like,
three or four years old in my life.
So my parents were pretty hesitant.
They're like, why?
(26:23):
You don't need to get on the plane.
I'm sure you could just email him.
And, like, no.
I gotta go out and and try to see if I couldstrike up a conversation with him.
I was walking to Chipotle to get lunch afterone of the speakers was done speaking, and I
see him coming out the back entrance.
So I just walk up to him, like, hey, Jack.
This is what I'm doing.
Super generous with this time.
Spent, like, three or four minutes talking tome.
(26:44):
Didn't have to do that.
Yeah.
And at the end, I'm like, hey.
We got the show.
We'd love to have you on.
He's like, yeah.
I got a baby coming up in a few months, butI'll do it after.
I think just having those types ofconversations and just getting on the plane,
taking the train, going, taking the meeting,responding to that email, I think can be those
micro differences and micro, I guess, decisionscan be the thing that makes the difference
(27:05):
between making it and not.
I love the hustle, by the way.
That's awesome.
But we I mean, it's it's beyond just sort ofthat initial thing of of winning a deal.
There's also, look, the journey of a startup,as I mentioned earlier, is just never linear.
Like, there's always going to be ups and downsand changes because it can take ten, twelve
years to go from an investment to an exit.
(27:27):
And so if the foundation of the relationship isbuilt on, hey.
No.
We worked super hard.
We came here face to face.
We went to Germany or The Czech Republic orwherever, and we sat down.
We had a meal.
When that trust is established from thebeginning, it makes the the tough conversations
that you're gonna have over a decade just mucheasier if that's the orientation from the get
(27:48):
go.
This is more general, but there are people inthe audience who might be listening to this who
are kinda following the things that you'vementioned.
Maybe they're spending a lot of time grinding,hustling, getting on the plane, paying
attention to all the micro details, but theystill feel stuck.
How can someone who might be in that positionget unstuck?
There's two types of stuck.
There's short term stuck and long term stuck.
(28:11):
Short term stuck is maybe cheesy guys.
Get outside.
Go for a run.
Go if you're in a city, go to a differentneighborhood you don't normally spend time in.
Maybe don't bring your phone.
Don't look at it.
Just remove yourself from the problem thatyou're ultimately trying to solve.
Get some different experience or perspectiveeven if it's only for a few minutes.
(28:32):
For me, it's running.
I go over the the holidays.
I was working on a particular problem.
I I I live primarily in Chicago.
I went for a run.
It was 15 degrees outside.
I didn't care about the weather.
I responded and helped solve the problem afterthat.
I'd say more more seriously and more long term.
If you're feeling stuck, take a second andevaluate, like, what part of this do you feel
(28:53):
stuck on?
Is it is it a market and or problem issue?
In other words, is the track simply not longenough to run the race that you want to run, or
is it too cluttered to run the race that youwanna run?
Or are you feeling like you have somelimitation that you can identify to say, hey.
I'm not able to do this for x y z reason inwhich upskill.
(29:13):
I think it's a matter of, really, for thoselonger term conversations, thinking about, is
it there is it external?
Is it internal?
And then from there, working to to diagnose it.
I think that's a really good point.
And throughout your time investing, you've beeninvesting for nearly a decade now.
What is the number one trait that makes a greatinvestor?
Yeah.
(29:33):
Curiosity.
Curiosity.
I think that you need to when you're to yourpoint, doing these two to eight week micros you
know, sprints to become micro experts in agiven field, there is there is a real advantage
to knowing two times more than the next bestinvestor knows or the next best person knows.
(29:56):
And so getting to a point where you have thisdeep endemic curiosity where you see a problem
being solved, you need to understand where itis.
That's gonna help you find better deals, winbetter deals.
Importantly, you know, people VC, we talk a lotabout doing the investment.
As you're you know, I'm involved I've beeninvolved with now 20 plus boards over the
course of my career.
As you're a board member to and partner tofounders, that curiosity alongside of them is
(30:19):
also able to make you just a much betterthought partner.
And you're trying to become the best consumerinvestor and the best in your space.
To do that, you also need the best team.
How do you evaluate and distinguish a playersbetween b players and c players?
What what is so unique about them that you'reable to see early on?
(30:39):
Exactly why somebody is an a player, the spikethat they have, that can differ.
We have some folks who are exceptional atnetworking.
So they're able to meet everybody.
They become a gravitational pull in this space.
We have some folks who are exceptional one onone with founders, who are able to build
trusted relationships, some who justanalytically can see things ultimately in
(31:02):
different ways.
The underlying, commonalities that existbetween all of them is an ownership mentality.
So really caring about what they do, thinkingabout the big picture, absolute just hunger and
drive and continuing to push through things,and then empathy, honestly, and an
(31:23):
understanding for the people that they'reworking with.
So those three things underlie each of it, andthen you have the specific skills.
And so we'll we work with people.
You know, I think we're very intentional whenwe hire people around the goal is, hey.
We want you to become a partner here.
That's that's the goal that we have.
So we'll work with people very explicitly on,hey.
We need to work on this, or you did a great jobhere.
Work on that.
But those are some of the traits that we seereally distinguish the a players from the from
(31:47):
the b players.
And we've talked a little bit about thecompanies that you've invested in over at
Leftlane.
If you had to start a company today, right now,what space would it be in and why?
That's a great question.
I so for me, the thing I'm probably mostinterested in right now is the intersection
between personal finance and AI.
(32:08):
If you look at a lot of the deals that I'vedone or or worked on, just this idea of saving
families and households money and helpingpeople start businesses, finance businesses,
and run businesses.
Those are two of the themes that I think arekind of the the back room the backbone of my
career as an investor so far.
(32:28):
And when I look at what we've solved so far,one, I think the issue of, okay, can,
consumers, can small businesses get access tofinancial services?
Simply bringing them online was a monstrousstep.
Right?
And I think we've seen a lot of the benefitsthere.
As I look at the limitations, though, of onlinebut done by you, I think they're really clear.
(32:52):
Right now, there is so much information thatconsumers just don't know, unstructured
information that consumers, small businessowners don't know, don't have the time to know.
Everyone else has has other things that theyneed to do.
And the second, the process of actually usingthis information to do something with it is
extraordinarily opaque.
(33:12):
Like, I I'm a cofounder of a $2,000,000,000financial institution and bought a house
recently, there were huge swaths of it thatseemed esoteric, super complicated.
Right?
Both of those problems seem absolutely tailormade for for for AI to step in and and be able
to make it easier for folks and sort sort oftake us to the next generation of that.
(33:33):
I've seen the beginnings of some companies, Ithink, are interesting, but I think there's a
decade long plus, tailwind behind that that'sgonna just, frankly, improve outcomes for
everybody involved.
And we have a couple of closing questions thatwe like to wrap each interview up with.
One is, if I slid you over a phone and youcould call your 20 year old self Yeah.
(33:54):
Would you call?
And if so, what would you say?
My 20 year old self would be really freaked outif you gotta call for somebody.
No.
I so it's a good question.
I would call my 20 year old self.
I think the main thing that I would push thatperson to do is to just have far less fear or
(34:16):
concern of the downside of interactions andconversations.
Naturally, I'm a somewhat introverted person.
And so I think if I could go back and just say,hey.
Look.
No.
Go have that conversation.
Right?
Like, go get in front of that person.
Take that initial step.
I think the earlier you can start to do that,the network effects in your life are just
exponential and they compound.
So I would really push people in thatdirection.
(34:37):
And what's one rule that you live by that mostpeople don't?
One rule I live by that most people don't.
It's the first time I really have to stop andand think about something.
Probably the biggest thing within venture attimes, there can be a trade off between short
(34:57):
term outcomes, short term success, and thenlong term reputationally.
Right?
Like, what are you ultimately working towardsand building towards?
I think one of the things I try to focus on isunderstanding that our goal and our ambition at
LeftLion is to be successful for decades.
Right?
And so when that's your orientation and that'swhat you're pushing on, then the way that you
(35:19):
interact with founders, the way that youinteract with other investors.
You try to have that long term orientation.
I think we emphasize that.
I think you'll hear examples of other folks inthe industry maybe not necessarily doing that,
and that's one of the things we try to push on.
One interesting answer I'll give you to that,question was also Zach.
I asked him the same thing, and he said hewants to constantly reinforce that he has full
(35:41):
control on his life.
And here's what he mean by means by that.
When he got off the train he lives in LongIsland.
When he got off the train from Long Island toNew York to the studio, there are a few
different doors that he could go through.
The shortest one is what or the one closest tothe train is one pretty much everybody was
going into.
Made the most sense, most logical, etcetera.
(36:02):
But he thought, hey.
If my life's a simulation, I'll walk throughthat door.
But I wanna reinforce that I'm not in asimulation.
So I'm gonna go to the door all the way on theleft just because I can.
And he does this, like, all the time.
He'll make, like, micro decisions during theday.
Maybe instead of taking the shortest path to adestination, he'll spend an extra three minutes
walking a totally different block that wouldtake four or five minutes longer just because
(36:26):
he wants to reinforce that he has full controlon his life.
So that, I thought, was a pretty interestingway to think about it.
So when I was younger, I actually would gothrough a somewhat similar exercise of thinking
about, okay, well, probabilistically what pathshould I do and and was also somewhat focused
on that.
Then I had a kid, and I realized that I havevery little control over certain parts of
(36:50):
things.
It went out the window when my son startedwalking and decided to try to throw himself off
the back of my couch several times.
Then you gotta be logical and be like, alright.
I I should probably do something here.
Right?
That that's when I realized, like, seeing achild go through a fascination of simply
causing effects in life makes you understandthat you really need to be prepared to stop the
(37:10):
cause of various effects, come hell or highwater.
And to wrap it up here, what's one piece ofadvice you would give to somebody who's
listening right now who seems who has seen whatyou've done and, also wants to be able to
accomplish something similar?
With venture capital, the name of the game isfinding deals.
And so if you want to get into venture capital,act like you have the job now.
(37:31):
I think that's a cliche that people use, butwe've hired multiple people who got a foot in
the door simply by sending us deals or sendingus ideas, and ultimately getting in front of
us.
And so that is for VC, it's simple and superdifficult.
Get in front of great founders and bring usdeals.
Yeah.
And Jason Schuman from primary has a veryinteresting story along that path as well.
(37:53):
He started a shoe business in college at UMiami.
It didn't end up working out, but he moved outto Boston.
And, he's like, hey.
This venture capital thing seems prettyinteresting, but, like, I don't know how to get
a job in it.
So he would start sending deals for free.
This is before you could, you know, getcommissioned or or be be a scout for a firm.
He would send deals to VC firms in Boston forfree.
(38:16):
But, you know, he still had to pay the bills,so he'd drive for Uber at night.
And that's how he was able to get his first jobin ventures because one of his passengers was
actually a VC and was like, hey.
You you should probably we should probablytalk.
Super interesting path.
But I've noticed that one of the things he'stold me and I've always kept in the back of my
mind is if you can do the job before you getthe job, then you can get the job.
(38:38):
A %.
That's absolutely the right orientation,particularly when it comes to to venture.
Well, I think that's a great way to end it.
Thanks, Dan, for taking the time to join theshow.
I appreciate it.
And if anyone's a founder, especially inconsumer or in any of the areas that Leftlane
invests in, feel free to take a look at theirwebsite in the episode description down below.
And thanks for joining.
Thanks, Simon.
Appreciate it.
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