July 25, 2025 • 49 mins
In this episode, Katelyn Donnelly from Avalanche VC shares her journey from McKinsey to becoming a venture capital leader. She discusses founding Pearson's corporate VC arm, her work with Delivery Associates, and insights into government projects. Katelyn offers career advice for new investors, trends in education, and transitioning into venture capital or private equity. The conversation also covers communication skills, portfolio strategies, cross-border investments, and the impact of AI on venture capital. The episode wraps up with audience questions on balancing VC goals with a full-time job and starting with SPVs.
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I ended up staying for eight months, and it wasthe fastest reforming education system on the
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planet.
And the senior partner asked me if I he wasthis global education system expert, and he he
asked if I'd like to be a chief of staff atPearson because he was leaving.
And I was like, all right, that sounds cool.
Like, I'll get to live in London.
And I'd never like thought much about theeducation industry, but, you know, it seemed
(00:25):
like a great opportunity.
And I thought I'd be there for a year.
And then I ended up staying for five and a halfbecause I had the opportunity to found
Pearson's corporate venture capital arm.
Welcome to The Investor, a podcast where I,Joel Palafinkel, your host, dives deep into the
minds of the world's most influentialinstitutional investors.
(00:49):
In each episode, we sit down with an investorto hear about their journeys and how global
markets are driving capital allocation.
So join us on this journey as we explore theseinsights.
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Alright.
So I think we are live here.
So really, really honored to have CaitlinDonnelly here.
She's a new friend and just excited to get someFaceTime with you.
We had a really good discussion a couple weeksago.
What I really enjoyed was just yourentrepreneurial story.
So kinda, you know, how you broke into to VCand kind of made that transition.
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So really excited to kind of share that withthe community as well and, and have everybody
hear your story of, you know, you reallysuccessfully scaled a business.
I remember you kind of talking through that.
So that was really great to hear that.
And, know, it was funny because there's been afew VCs recently that have wanted to be
founders.
And there's a lot of founders that are nowbecoming new LPs in VCs.
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So I guess the grass always seems greener.
So that's always interesting.
But welcome to the show, Caitlin.
Excited to, you know, just go deep on yourbackground and your your journey, and also
starting a firm.
I know you also have a website where you gothrough your investment thesis.
It's called obviously the future.
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So really excited to, to go deep on just yourthesis and, and hear what you're excited about.
But let's kick this off.
Let's hear a little more about, you know, yourbackground where you grew up and, and how you
came into VC.
Were you exposed to VC early in your career?
Was that something that you got exposed tolater?
For me, I knew nothing about VC early on.
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Was a tech person and then found out about itand broke in later in my career.
But excited to go deep and learn about you andyour background.
And again, once again, welcome to the show.
Yeah, thanks so much for having me.
So should I start from the beginning or?
Yeah, let's start from the beginning.
Let's hear, you know, where you grew up, whereyou studied and, and you know, and you started
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a couple businesses and then became aninvestor.
So let's, yeah, let's hear whatever you'reallowed to share.
Yeah, so I grew up born and raised inMinneapolis, Minnesota.
So mostly in the suburbs, but was downtown fora bit.
It was a great place to grow up and definitelyfeel like I have Midwestern roots, but I was
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always eager to like seek new frontiers andfind new experiences.
And I decided to go to Duke for school.
And I remember, going, we've been in Minnesotaand seeing like the brochure for Duke and
looking at it versus like Ivy League, it justseemed like a very innovative school, like a
school that had to be a little scrappy to getahead versus some of the established Ivies.
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That always really appealed to me.
And then when I was at Duke, I studiedeconomics and always wanted to like work in
investing and did my summer internship atMorgan Stanley on the sales and training desk.
But my senior year, I was the president of thestudent union.
And there I really had this opportunity torestructure the organization and run it as a
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business at a million dollar budget, largestbudget on campus.
And I always joke that my first ventureinvestment is we seeded the record like
recording studio in, at Duke, which are, thefirst album was like, what's that guy's name of
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like, like one of the, like a famous artist is,did like, did a song on that album.
So I was like, that was my first like VCinvestment organization that I was managing
that had all these different subcommittees.
I So you
kind of seeded the production of an album?
Or or did you see the studio?
Studio.
Oh, wow.
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That's cool.
Yeah.
It was and then they made their first album.
Mhmm.
I wonder which artist it was.
Was it TI or No.
TMI's from Atlanta.
Right?
It was the guy who did, like, waiting for myplane to come.
Like, why am I blinking on it right now?
He's the guy who walked across the country,like, barefoot, recently.
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Oh, I don't know.
Maybe we'll get some help from the audience aswe try to Oh,
God.
Blanking, but
I'm
sure it'll come to me like I have.
Yeah.
Like that.
So I graduated in 02/2008, and during my senioryear, had this offer to go to Morgan Stanley,
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and I took a class on VC and entrepreneurshipmy senior year, and the other thing that was,
it was kind of like a weird coincidence,everyone was going to investment banking and
consulting, except for this one guy who hadtaken a year and his high school friend had
founded this company called Box and he was theCFO and he was like, just trying to finish up
Duke or whatever.
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And we'd have these guest speakers come in andhe asked these like really specific questions
and like all the rest of us were like, oh,like, you know, who, like no real context.
But anyway, so that was this guy named Dylan,who was like one of the co founders of Box,
which I-
Oh, like box.com?
Yeah, yeah.
Oh, wow.
So he was in my senior year VC andentrepreneurship class.
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And then I, you could sort of see the likemarket turbulence at that time.
And I decided that instead of going to MorganStanley, was going to work at McKinsey instead
and in San Francisco.
So I joined the week that Bear and Lehmancollapsed.
Sure.
And ended up doing like all this cost cuttingand liquidity stress test for banks and cost
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cutting across Silicon Valley and, you know,like met different, it was like a very like
dour time in the And Bay I came out of that in2010, I guess, after my like two year period
and decided to do a third year.
And I saw this project on the pipeline to workwith the government of Pakistan to reform its
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education system.
And I was like, all right, that's totally weirdand different and unlike anything I've ever
done before.
And I'll do this for two months and then I'llcome back and work in tech.
I ended up staying for eight months and it wasthe fastest reforming education system on the
planet.
And the senior partner asked me if I, he wasthis global education system expert, and he
(07:42):
asked if I'd like to be a chief of staff atPearson because he was leaving.
And I was like, all right, that sounds cool.
Like, I'll get to live in London.
And I'd never like thought much about theeducation industry, but, you know, it seemed
like a great opportunity.
And I thought I'd be there for a year.
And then I ended up staying for five and a halfbecause I had the opportunity to found
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Pearson's corporate venture capital arm.
Oh, wow.
That's great.
In EdTech and education companies all over theworld and kind of set the strategy from the get
go, made the first investments, like set up theinvestment committee and got to do that full
stack.
And then also at the same time, saw Pearson'sLP investments and M and A activity globally,
and really did a lot of work on what the futureof education looked like and how the markets
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were developing.
And one of the papers that I wrote at that timewas called An Avalanche is Coming Higher
Education and the Revolution Ahead thatpredicted the rise of Coursera and MOOCs and
the unbundling of the higher ed sector.
And that's ultimately, you know, what I namedmy firm after was that analogy of mass
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disruption.
So I left Pearson, it's probably been like fiveyears now, five or six years, and I founded
this company called Delivery Associates withMichael, who is my mentor from McKinsey and a
couple other people.
And we work with governments to drive bigreform programs and deliver technology, never
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raised any money, and now have 160 peopleprojects all over the world, profitable,
growing, and I wanted to get back into earlystage venture and be an investor.
And so I started to invest my partner dividendsand proceeds into LP stakes in different funds
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where I really had conviction around a sectorand then started making angel investments that
I then warehoused and turned into the firstfund of Avalanche BC.
Yeah, no, that's great.
What are some things that you learned?
I'd love to double click a little more on justbuilding delivery associates.
So like how did you ideate the MVP and thenwhat's really challenging and what people don't
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really get to all the time is a series A.
So how did you really scale?
What was the scaling factor that helped you tokind of get from bootstrapping and maybe, you
know, first customers to really hyper growth toget to the next really serious milestones of
product market fit?
Yeah, so Delivery Associates is based on thismethodology called Deliverology, which is a
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framework for how you get governments todeliver results.
And when I was at McKinsey in Pakistan, we wereapplying that framework to the government
there, and it ended up being the fastestperforming education system in the world from a
low base.
And so ministers from around the world werecoming up to me and Michael, the senior
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partner, and we're like, how can we replicatewhat you did in Pakistan to our countries?
And Michael, you know, who was the seniorpartner had done this before in The UK and
developed VIP.
And so we had, there was definitely productmarket fit because, you know, governments need
to deliver.
This was a method that was developed within theBritish government originally, and was about
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productizing it and commercializing it, andthen putting together the organization that
could go win contracts.
And for us, I mean, to your point about theinflection point is we got maybe like two years
in a really large contract with a governmentthat was like multi year, multi million, and
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that allowed us to invest in our systems andthe capacity to go out and win a bunch more
contracts.
And the sales cycle is so long to win thesethings, but once you do, and assuming you like
do a really good job, then you can win the nextone.
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And the market is, it's like small, get to knowyou, they know you're not going away, like you
build a reputation for your work.
And that was one of the biggest things that Ilearned that I bring to the entrepreneurs at
Avalanche is like, I've seen that like, can, Iwouldn't say like, yeah, I mean, struggle for
like a long time, like three or four years, butassuming that you don't give up and you really
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are focused on like what your customer wantsand delivering a really good customer
experience, you'll hit escape velocity assumingthat there's a real need there?
Yeah, that reminds me.
So there's a guy named Deb Neil.
He is in Singapore.
He founded Decacorn BC.
I think part of it is like his own personalwealth as like an evergreen fund.
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But one of the companies that he launched whichwas really successful was and he had a
liquidity event.
But what he did was he had one customer, Ithink it was in the Southeast Asian government,
and they needed like an insurance system.
And there was a bunch of legacy systems outthere, but because he was a small company, was
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able to kind of like, just kind of buildexactly what they needed.
And then I think they became so happy that theyreally marketed for him, especially if you can
build that trust.
Because most vendors, I mean most softwarecompanies, you get kind of a package and then
outside of the package, there's somecustomization.
But, you know, when I worked in B2B SaaS, thechallenge is like, especially if you work with
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a vendor like that, there's a lot of likethings on their pipeline, but they're not
planning to release those things until maybelike next year or something like that.
So you're kind of beholden to like the road.
You have your roadmap, but your hands are kindof tied because that software platform, they
have multiple customers.
So they're kind of, you know, managing abacklog of like multiple things.
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But I think to your point, if you can get thatfor it sounds like this is what you did.
You had that first anchor customer where, youknow, they they were really happy.
And then I think once you build that software,can probably resell it.
And then, know, you have the budget, so you canprobably invest in sales and more tech
resources to kind of add product success, I'massuming.
Right?
Yeah.
And then you, you know, hire smarter peoplethan yourself and, like, the different
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verticals, and then they create you know morevalue and it kind of compounds.
Yeah and then did you end up did you end upselling that company or is it just operating on
its own now and you kind of hired somebody tokind of run it I guess, or?
Yeah, so one of my partners is the CEO and heruns it, I'm on the board, still a shareholder,
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but yeah, operates more or less without my dayto day.
Yeah, no, that's so amazing to see that youwent through that experience because there's
just so much wisdom that you can hand off toportfolio companies, but also portfolio funds,
right?
So tell me how that experience has been beingan emerging LP.
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Really appreciate all the support that you'vebeen doing, obviously with my ecosystem too,
but what are some things that you've beenlearning as kind of being an emerging LP and
now kind of building your firm as well?
Yeah, so I am a big believer in theseavalanches, as you say that I write out in
obviously the future.
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So like my first LP investment was in a fundcalled Noetic Fund out of Canada that was
investing in psychedelics.
And my thesis there was like psychedelics asmedicine is going to happen.
And I wrote out this thesis and then I guess Ihad like found somebody who was starting this
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fund at the exact time and invested in it.
And one of the things that I think has been agreat innovation in the ecosystem over the last
five years is like, I wrote a 25 ks check,which, you know, it's not like, when I was
starting my career in 2000 and in SanFrancisco, like no one's gonna take a 25 ks
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check into their And fund, now you can be an LPfor the size of like a small angel check and
gain exposure to a sector that I'm like, I'mnot an expert, but these other people are.
And I'm, you know, it's good to get thatexpertise and exposure without having to do it
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yourself.
Yeah, mean, it's essentially like an indexfund.
And then I think if you have, you know, acohort of all these funds, it's an index fund
of index funds, right?
So that's kind of the way I've been looking atit.
But, you know, you can either hire somebody togo deep on psychedelics, or you can try to
figure it out yourself.
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But then there's still the whole process oflike taking that company to investment
committee, where like, if you just invest intoa fund, most of those funds have co investment
rights.
So you can, can, you know, not only do you getexposure to that sector in a risk diversified
way, but they can also bubble up specific dealsif you want, you know, if you want to double
down and actually have more of an exposure.
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So, I think that optionality is reallyexciting.
And, and for me, you know, with our fundcohort, know, the next cohort we're gonna have
somebody that only focuses on quantum.
We've had a few psychedelics funds.
So I think for me, it's really cool to havelike these mini experts in these themes.
And to your point, it is accessible these days,especially the smaller funds.
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Obviously, when you're looking at funds thatare all like Fund IV, the minimum is going to
be much bigger, but still just kind of gettingexposure.
It's a great learning to be kind of an angelLP, so it's definitely exciting.
John Robinson, who's on the call, he's he'sactually backed.
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He's a buddy of mine, but he's actually beeninvolved in a lot of funds as well.
So been been a super active LP.
Hey, John.
Hey.
Yeah, so tell us some.
So and then on the on the early stage directinvesting side, what are some learnings that
you you know, because you kind of built thatangel track record, and then kind of evolved
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into, you know, getting into your first close.
What's some advice that you would give topeople just starting out, especially with the
landscape right now with macro indicators?
What would you recommend?
Mean, the feedback I'm getting is, it's a goodtime to be a founder, right?
I mean, it's if you're gonna be able to closecapital, know, do it now.
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I would assume that's the same thing as anemerging manager as well.
And I'd also assume it's just people still haveto deploy capital, right?
So fund to funds and LPs for their job, theystill have to invest.
But that's just my standpoint.
We'd love to hear some of your thoughts onthat.
Yeah, you know, I think one of the importantthings to ask yourself, no matter who you are
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or what you're doing is what's so special aboutyou and like, what's unique about you and
what's your edge and why are you doing thethings that you're doing?
Because I think that, you know, you want to be,you know, successful, especially in
entrepreneurship and investing, it's so hard,like it is so, we're playing the most
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competitive game on the planet.
And so you have to have something that is gonnalike tip the odds in your favor.
And the reason I didn't do direct investingpsychedelics is because I'm like, I'm
interested, but like, I'm not gonna tip theodds in my favor, but I invest in like ed tech,
future of work companies that I've seen the usecase for the company that I built, like things
that I really know and like, especially in edtech, I it's, I can be like, Oh, well, I can
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introduce you to this person and this personand this person.
I can actually tilt like people like give, belike, all right, well, I can invest my money
and I can tilt the advantages in your favor.
And I think that in terms of likeentrepreneurship, like starting delivery
associates, like I'd already done, had thislike track record of doing the methodology and
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having a bit of a reputation in it.
And so I think that you have to find thingswhere you can tip the odds.
And it seems like it just, I think when youdon't try too hard, it seems like all these
different switches in your career just seemedpretty natural, right?
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And I think it seemed like it was a funadventure as you made all these changes, right?
Like the education project in Pakistan, you'relike, why not?
It seems like a great opportunity.
And I think having a positive mindset is whatopened up all these other amazing opportunities
where you got to really build corporate VC andalso kind of build an LP practice and you don't
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always get those kind of opportunities.
Yeah, it's
a lot easier to connect the dots going backthan you're like, like I remember people were
like, why are you like, the people who are inPakistan are dying to go to San Francisco.
Like, why would you go the opposite?
Like, one thought that was, that was a goodidea.
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I mean, that's a piece of career advice thatI've given.
I mean, one of my first jobs was in theMidwest, it was in Iowa.
And it was a really good company, know, I got Ibuilt some really good technical expertise, but
I think because it was in Iowa, and nobodywanted to go there.
They treated me really well, like I had a lotof perks and but you know, other people
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probably wanted to go to like the moreglamorous cities.
So sometimes there's some edge in going tothese less desirable states or regions.
I know some people that have gotten some reallygood jobs in BC, but they were in kind of like
the middle of nowhere, but otherwise it'd bedifficult to break in or even be an LP.
But like they need they need talent and they'rewilling to kind of make it worthwhile for some
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people, you know, the best I can.
So it's kind of kind of interesting.
But yeah, that was that was like a lifelearning for me just kind of being flexible on
on that kind of stuff.
For me now it's more difficult right now that Ihave a family.
I'm a little more stringent on like locationnow.
But I think early in your career, it's it'smuch easier.
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So yeah, definitely.
Yeah.
What are some high level trends that you'reseeing?
We talked about MOOCs, and we talked about kindof the future of education.
What's some of the hot theses that you'rethinking about now as you kind of write your
next submittal on your blog?
I have a draft for nobody wants to be like, Idon't wanna be your boss or like, nobody wants
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a boss.
I think it's like rise of like, some people arelike creator economy, or like freelance
economy, or like the sort of like Dow movementof being like, okay, these like hierarchies and
management theory is maybe not how people wantto engage, especially in like the knowledge and
software sectors in the future.
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And I think that that shift both culturally andlike having tech to enable it is really
powerful.
Yeah, I think it was Footwork.
I forgot the fund.
It's a fund called Footwork.
They're on the West Coast, pretty well knownfund, but they wrote a blog recently on just
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leverage that employees now have, like theshift of power is now coming to the employees.
It's obviously they have a much better say.
Think some of that might shift a little bitlike the economy.
But I think just the way that Gen Zs look atemployment, I feel that's different than the
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millennials.
Right.
And I think people, if they're not happy,they'll to your point, right, just try to build
something on their own or be a creator or haveside gigs as well to maybe augment their
current role.
So I think that's definitely a thing.
But I definitely think, know, especially withthe great resignation, I'm assuming that's
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probably a catalyst for more educationplatforms too, right?
Because people are kind of taking a break andmaybe re enabling skills that they didn't have.
Is that something you're seeing as well?
Some of that for sure.
I think the biggest thing that COVID has doneor this period is actually in K-twelve where
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parents have pulled their kids from the publiceducation system and done homeschooling, pods,
micro learning, and they have not come back.
And so now you're seeing more of these likeeducation savings accounts of like how can
governments give, I mean, everything's kind ofpoliticized, right?
So like voucher being a dirty word, butbasically like direct subsidies for parents to
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be able to make, to choose what they send theirkid, like where they send their kids for
K-twelve.
And then I think like Gen Z is kind of likewizened up to student debt and they've seen
millennials go through, know, take out theseloans, not be able, not have them translate to
like, and get a return on investment into theworkplace.
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And they're like, well, wait, I could, youknow, like learn web three for free and get a
job being a community manager and then buildthis network and navigate these online
communities.
And so I think that like I'm not investing inany companies that augment the existing
secondary system.
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You know, like you're looking for things thatare going to completely transform it because I
don't think that it can be reformed from theinside.
Yeah, what are your thoughts on just gifted andtalented programs?
Because I feel like it seems like such anexclusive capability to get access to that.
And I think there's been some movements now tomake that more accessible.
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But I always felt that they should just havethat every school.
They should have kind of like a gifted andtalented department because especially in New
York and as you know, right, like the kids haveto go like somewhere on the Upper East Side and
they have to test into it.
But I feel like that that is not as enablingto, you know, because there's probably a lot of
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people that are gifted and talented, there justisn't enough room, right?
So I feel like they're trying to make that massadopted.
Then another thing I would ask is what isgifted and talented?
Like what somebody believes gifted and talentedis maybe different than somebody else, right?
So it's like we're just following this personthat has defined that you're gifted and
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talented.
So I don't know if you have any strong thoughtson that and just kind of how that plays into
the educational system.
Well, I think when you open access up topeople, you're like, well, why do you have to
go to the Upper East Side to go to some likegifted and talented program?
And I think, you know, one of the big companiesthat just got raised a big round was synthesis
school, which is like the unified-
Is it Elon Musk's school?
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I think it's basically like they took the techand the pedagogy and then have built a new
product off of it, But you're like, all right,I mean, it's kind of inaccessible right now
because I think it's around $200 a month ofprice point, which is pretty high for most
parents, but you're
like,
anyone can go join that, right?
So like, you don't need to be gifted andtalented, you just need sign up.
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And so now as long as you have access to acomputer and, you know, your parents can pay
out of pocket or this is where the state couldbegin to provide subsidies, The world's your
oyster and you can learn with kids all over theworld and you can pick your own, you know, the
things that you're interested in and yeah, likegifted and talented traditionally used to mean
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probably that like, you were good at math andlogic and like maybe we're a good writer.
And I mean, there's lots of people who aregifted and talented at TikTok videos and coding
experiments and so many niches.
Yeah,
I mean, thing that came across my mindrecently, was Kevin O'Leary, he posted
(28:24):
something saying that he used to think it wascritical to study computer science or business.
But he specifically said, the skill of beingable to communicate a complex message in like
fifteen seconds is going to be super important.
And I've kind of gone through that experiencerecently because I submitted something to an
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accelerator and I struggled for a long timetrying to say everything that I needed to say
in one minute as a video because it reallyreally makes you concise and precise.
Have to really clearly cut a lot of the noiseand you might have to skip some screens when
you're demoing something but it really reallyis you know, inspiring because it just kind of
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forces you to really deliver a message.
I can't imagine how difficult it would be tokind of do a startup pitch in fifteen seconds.
Yeah.
But even a minute, minute actually, dependingon how you look at it, it is enough time to
kind of deliver the one liner and deliver theproblem.
But I think that's still a difficult skill thatsome people might struggle with, because people
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might be super detailed, and they want to shareall the nuances.
And you kind of miss really the main point.
And I think that's kind of the balance.
So I think that's kind of a skill that'sprobably just as important as being an
engineer.
Because if you're building something sobrilliant, but nobody can really understand who
the customer is, then it's it really is kind ofa lost cause.
(29:58):
Yeah.
Well, maybe you can, know, I know we got a fewmore minutes.
Any advice you would give to people that arestarting their career transitioning from maybe
a non finance degree to venture or privateequity?
That they're trying to get into venture privateequity?
(30:21):
I think that quality of people really matters.
So really research the people that you want towork with, and then think about how you can add
value to them, and then tailor your approachand outreach to the people you want to work
(30:42):
with, and build a relationship with them overtime.
And really think about like what is the rolethat you're looking for and like do be
basically doing that role before you kind ofever ask like ever ask for a job or someone's
time like and I think you'll be able to standout from the crowd and develop a relationship.
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Like I'm surprised at how many people, or sortof the lack of people who really do like a
tailored, like high quality ask or think aboutkind of like adding value or, you know.
Yeah, no, I agree.
How important, know, I just spoke with somebodyearlier this afternoon and, you know, their
(31:31):
feedback, they kind of had a similar journey toyou and I where they came from kind of a non
traditional path, but they were saying thatkind of the banking financial modeling isn't as
important, but it's really kind of therelationship building and really
thoughtfulness.
Would you agree with that?
Guess are there any specific hard skills thatyou would recommend people to brush up on if
(31:54):
they're trying to break in for the first time?
Has that changed?
Because I know before it might still be thecase.
I mean, is still kind of a pedigree focusedindustry, but I do see that changing, but would
be curious to hear your take on that.
I think as you go, so when you start at preseed, like there's a lot more like or seed
(32:16):
because there's a lot less out there.
You don't have to be so like analytical andprescriptive, but as you get farther up, it's
so analytical and so precise.
Also when you're managing other people's money,like the bar is just, and standards are really
high.
And so I think more than it even being like apedigree point of thing is like, I see people
(32:40):
who maybe don't come from the, don't have thepedigree, but it's not really like the pedigree
or not, it's like the standards andexpectations, like going through McKinsey, you
were ground down, like every little detail hasto be right structured thinking, you know, it
was a more intense training program thanundergrad.
(33:01):
And I don't think it can be like understatedhow important that level of precision and skill
is, especially if you're like managing otherpeople's money at scale.
So yeah, I think it's good that there's peoplefrom different backgrounds, but also just the
bar is high for a reason, you know.
(33:22):
Yeah, I'd like to take a couple minutes also totalk about portfolio construction, right?
So I think that may be an interesting topicthat I haven't talked about in a while.
So what you know, how did you go about yourportfolio construction, thinking about how many
checks you want to write, know, the sector, thestage and then kind of, you know, what your
goals were for first close?
(33:44):
Any advice you would give to someone who's, youknow, maybe had an angel track record?
And now they're like, wow, I think I'm going tostart thinking about maybe getting some first
angel checks into, into my fund?
Would you recommend them building a frameworkaround portfolio construction?
Well, my first fund was small, it was like amillion dollars.
(34:07):
I kind of anchored it and I did 20, it wasn'ttotally precise, but like 25 ks checks and I
did 36 unique investments and then two followons.
And
the check sizes were like, I wanted reallydiverse.
(34:32):
I wasn't going into hot rounds, like I wantedthe valuations to be low, which has turned out
to be good.
I wanted to get a lot of reps in because Iwanted to be able to get, you know, to learn
and grow.
And then I was also offering my LPs adiversified portfolio.
(34:53):
So I can't remember exactly what the number is,but it's like, at least have to have 20, maybe
25, maybe even like ideally 40 investments ifyou're gonna hit the power lots, I have one
really gonna be a winner.
Sure.
And so I wanted follow that.
What was the range that you were trying to stayin for evaluation?
(35:18):
Were you trying to stay in like this six under10,000,000?
6 to Pre
seed, I wanted to do definitely under 10.
I just did the analytics on this for theportfolio and my seed post, my average pre seed
post money valuation is like 6,600,000.0.
Okay.
And my average seed is just under 20.
(35:40):
So
I feel pretty good about that, all thingsconsidered.
Did you do any cross border investments?
I don't know if you know Kalsum, but yeah,she's she knew.
So she was in my one of my past cohorts, butjust a trend that I learned from her and just
other VCs that are investing in Africa, India,Southeast Asia, you can get like an amazing
(36:04):
company and like the valuation is, you know,sometimes I mean it's much higher now, but
probably two years ago you get like a rocketship company for like, I've seen some of them
for like 4 to 6,000,000.
Now it's now it's at par, you know, and you'vegot Tiger Global investing in a lot of deals.
But did you you do any cross border deals kindof in emerging markets to kind of learn about
(36:29):
those sectors or?
Well, I cut my teeth when I was at Pearson inemerging markets.
Yeah.
And like I've known Kelsoon or known of hersince 2011, because I lived in Pakistan.
And honestly, like I've looked at people in TheUS like investing money in emerging markets and
(36:52):
I'm like, you have to have risk, like thosemarkets are tricky.
Like it's tough.
It's not like, I think that people haveunderestimated some of the risks there and I'd
much rather be an LP in fund, someone whoreally understands those markets, knows all the
people, can spend time with the entrepreneursthan people who are just like, hey, this looks
(37:14):
like a cheap deal in Pakistan or in Nigeria orwhatever because like, know, there's a huge
information.
You're shooting blind, yeah.
I think that's good too because if you investin someone talented like Khalsum, you know they
have a lot of these emerging managers.
They don't have that rigor and really, reallystrict discipline and you know just really,
(37:39):
really strong vetting process, won't they won'tget to their next fund.
So I think that's what gives me confidence inthe fund managers.
And yeah, you're right.
I I would be shooting blind, like just tryingto get some arbitrage with a direct deal.
What I have done is like, she's someone thatwould be a really good co investor for me
(38:01):
because I'd like, all right, I'm an educationor future work specialist.
You know the market super well.
So we'd be really great, like complimentary coinvestors.
So I would always try and like co invest withon the same terms as an investor like that.
Yeah.
No, absolutely.
I've done that a few times with some LPs too.
And I would say that's been that's been agreat, you know, piece of feedback that I've
gotten from people just kind of building thatco investment relationship.
(38:24):
And then if you've done like three or fourdeals together, then sometimes those people may
want to just support you and just come intoyour fund as well.
So that's also been kind of a win win.
Have you used the tool?
I'm a power user of tactic.
I'm assuming I don't know how long Tactic hasbeen around, but I'm assuming like when you did
your early portfolio construction, was probablylike all in Excel.
(38:48):
But I'm like a power user.
Don't know if you've used Tactic, but it's likeone of my favorite products now.
Yeah.
Yeah.
I really like too.
I actually have both an Excel model and thenI've been on on Tactic.
Yeah.
So yeah.
So I'm pretty good friends with Anubhav and I Idid like a live stream with him like two, I
(39:09):
think last week because I just wanted to learnall the new enhancements that he had.
I was like, you know, I might as well justshare this with everybody.
So we just kind of did it live.
So it got me up to speed and I just kind ofshared it.
But I think that's really exciting with Venturetwo.
There's just a lot of new tools that people canuse to kind of, you know, start these funds
(39:30):
much faster than before.
I think before it was a lot more opaque andthere's a lot more content and community around
it, which I think is enabling a lot morecapital coming into the funds, which
essentially will be going into the portfoliocompanies as well.
So that's also
I think is good about it is that it's basicallycommoditizing a lot of the back end part of
(39:54):
venture, but it does put the onus on, I think,fund managers to actually be able to add value
to the companies, because anyone can now like,you know, use that no code tool and come up
with a portfolio.
So like, that's not the hard part.
The hard part is building companies that makethings that people want that are going that
don't fall apart because of co founder likeDynamics or a bad board member or all the
(40:21):
things that are not commoditized.
Yeah, no, that's a good point.
Yeah, I mean, I think when you have too muchautomation and you have too many AI portals
that are serving deals up, then you becomeobsolete, right?
So I don't think that will happen anytime soonbecause I think there's still an art to using
(40:42):
your judgment, right?
Because I think beyond the numbers you'relooking at human beings, And you're kind of
judging their character and deciding if youwant to spend the next seven years still on
that journey with them.
So sometimes just the algos may not always beable to pick that up I would say.
So never say never but
(41:03):
Or the problem is it becomes like sleepy captable money you know, because like, people who
are investing based on an algorithm are notgoing to pick up the phone on like Saturday
night when your CTO is thinking about quitting,you know.
Yeah, sure.
Yeah, no, absolutely.
I think those are, I mean, it's great when thetimes are great, but I think, you know, the
(41:27):
value also comes when there's tough times andthey can have somebody to call and kind of get
through that because you have a vested interestin them being successful as well.
Yeah, exactly.
Yeah.
Well, you know, I really appreciate all yourtime, you know, maybe I'll open it up for a few
questions if people have any.
So anybody on the call have any questions?
There was one in the chat?
(41:50):
Well, someone, won't say who it is because itwas the direct message asked what is adding
value to me?
Oh, okay.
And I think it was like in what this personasked the question when we were discussing, you
know, intros breaking into the sector.
I think sourcing a deal, like a good deal isalways adding value.
(42:13):
It's always value additive.
Like not just like a random one, but if you'relike, oh, I really like saw this company, think
it's really interesting for these reasons.
Like that's always a topic that like I'minterested in that I'd engage on.
That was helpful.
John, I know you pinged me asking if you couldask a question, you got a question?
(42:34):
Yeah, thanks Joel, and thank you very much forthis talk.
This has been great, Caitlin, appreciate it.
I am kind of in a situation where I was tryingto get active with Joel's help.
I've been networking a lot.
I was trying to get I have an Angelistsyndicate and I was trying to kind of get off
(42:55):
the ground.
And I made some connections.
But then, you know, I to I got laid off fromwork and I had to find a new job.
So I got the new job.
That's good.
But I just, it's hard now to kind of dice mytime up in the way that I want to, to give the
attention that I need to, to my VC connectionsand the people that I'm the startups that I'm
(43:17):
working with.
So I was just wondering if it's more like atime question.
Was just wondering if you could, any insightsyou might have on just how to split time if
your full time job is outside of VC?
I think it's incredibly difficult.
Like, think about time management every day.
I'm like, how do I manage time?
(43:38):
I think it's probably quality over quantity.
So like narrowing your focus and your world.
And so for me going even between from fund oneto fund two, I kind of narrowed the focus of
the companies that I was interested in and thenqualified for LPs in my fund and really was
like, all right, I'm gonna go after like thecompanies that are 95% likely to be in my sweet
(44:06):
spot and only take those meetings.
And then for LPs, I'm like, okay, is thisperson really like, do they already really like
me?
Are they interested in my sector?
Do they write checks?
And like only take those meetings and not chaseafter like all of the other like noise.
So I think it's really about focus and thenstrictly prioritizing what's gonna move the
(44:27):
needle for whatever your objective is.
Yeah, that's really good advice.
Thanks so much.
Appreciate that.
Yeah, cool.
Any any other questions?
We'll take maybe one more and then give Caitlinher time back.
Hey, Joel had one question.
Sure.
Hi Caitlin.
Thank you for your time this evening.
(44:48):
As you were getting started in launching yourown fund, did you ever invest through SPVs
early on?
I have invested through SPVs.
I will say like, oh, it's not true when I didlike, it's not totally true, but whenever I was
(45:09):
like invested in Angel List SPV where I didn'tknow the founder, like I didn't have a
connection with them before, it's kind of justbeen like a financial investment almost just
like buying Microsoft stock on Vanguard orsomething, it's not like anything exciting to
me and I feel like I get no information abouthow the company is doing and so.
(45:34):
Well, guess to be more clear, I meant it as didyou start an SPV on your own and use that to
fund the business?
Build a track record?
No.
Okay, got it.
So did you go straight to like starting yourown firm basically when you were ready?
Yeah, I started at Angel Invest my own money.
(45:54):
Then like one of the things that's great aboutstarting a successful company is that you then
have, you're like, you can go to your cofounders and like other people that you've made
money for or whatever and get them to likeinvest in you.
I mean, I think that it's, I know thatdifferent people have different models that,
like there's some people who are very active onTwitter and have these big like marketing
(46:18):
presence, like that's not me, I'm like morelike introverted, but like deeply expert in
what I do.
And you know, I kind of went to my friends thatI knew this could be like a good fit for were
high net worth individuals.
(46:38):
And like, one of the things that I see now thatwasn't the case when I was young is like people
who are really young trying to break into VC.
And I'm like, I can do it now because I'm in mymid thirties and my friends are like partners
at managing directors at banks, partners atconsulting firms, like they're like wealthy
(46:58):
accredited investors.
Like there's no way I'd be able to do that whenI was 25, you know?
Got it.
Yeah, one more thing that I'll, oh, go ahead,Manveer. Had
Had one more anecdote to add to that, but goahead.
One final point just to get, I guessclarification is your, would you, I heard you
mentioned EdTech multiple times, would you saythat's your core emphasis?
(47:20):
I'd say it's the area that for better or worse,I know the most about.
And I say for better or worse because I bring,like you bring your full bias of like, well,
that won't work.
Like I've seen this, it's failed.
And so sometimes it's good to be like a littlebit naive, I think about a sector.
(47:42):
So, but that's one that I just like mentioned alot because it's very easy for me.
Got it, thank you.
One thing I was gonna say is, I spoke to an LPlast week and you know, and I've heard this
too.
I mean, LPs through the diligence process maywant to talk to portfolio companies to kind of
(48:02):
hear what like the portfolio companies sayabout the VC.
But you can't really do that if you just, youknow, did these small checks into angel list
because you can't, you know, you haven'treally, you can't really number one contact the
founder and they won't have anything to sayabout you.
So that's the benefit of kind of justpersonally kind of like what you did and I've
done the same thing, kind of personallyinvested on the cap table and hopefully those
(48:26):
founders you built enough goodwill where youcan get in at a decent minimum.
Yeah, yeah, cool.
Awesome.
Well, hey, thank you so much, Caitlin.
I know you're super busy, so I really, reallyappreciate you being generous with your time
and sharing your story.
We all learned a lot, so appreciate it andappreciate the friendship and have a good rest
(48:46):
of the week.
Hopefully, hopefully the weather is continuingto stay pleasant for the next few days.
Absolutely.
Thank you so much for having me on.
This has been great.
Yeah, absolutely.
Take care.
I ended up staying for eight months, and it wasthe fastest reforming education system on the
(00:05):
planet.
And the senior partner asked me if I he wasthis global education system expert, and he he
asked if I'd like to be a chief of staff atPearson because he was leaving.
And I was like, all right, that sounds cool.
Like, I'll get to live in London.
And I'd never like thought much about theeducation industry, but, you know, it seemed
(00:25):
like a great opportunity.
And I thought I'd be there for a year.
And then I ended up staying for five and a halfbecause I had the opportunity to found
Pearson's corporate venture capital arm.
Welcome to The Investor, a podcast where I,Joel Palafinkel, your host, dives deep into the
minds of the world's most influentialinstitutional investors.
(00:49):
In each episode, we sit down with an investorto hear about their journeys and how global
markets are driving capital allocation.
So join us on this journey as we explore theseinsights.
(01:17):
Alright.
So I think we are live here.
So really, really honored to have CaitlinDonnelly here.
She's a new friend and just excited to get someFaceTime with you.
We had a really good discussion a couple weeksago.
What I really enjoyed was just yourentrepreneurial story.
So kinda, you know, how you broke into to VCand kind of made that transition.
(01:38):
So really excited to kind of share that withthe community as well and, and have everybody
hear your story of, you know, you reallysuccessfully scaled a business.
I remember you kind of talking through that.
So that was really great to hear that.
And, know, it was funny because there's been afew VCs recently that have wanted to be
founders.
And there's a lot of founders that are nowbecoming new LPs in VCs.
(02:01):
So I guess the grass always seems greener.
So that's always interesting.
But welcome to the show, Caitlin.
Excited to, you know, just go deep on yourbackground and your your journey, and also
starting a firm.
I know you also have a website where you gothrough your investment thesis.
It's called obviously the future.
(02:21):
So really excited to, to go deep on just yourthesis and, and hear what you're excited about.
But let's kick this off.
Let's hear a little more about, you know, yourbackground where you grew up and, and how you
came into VC.
Were you exposed to VC early in your career?
Was that something that you got exposed tolater?
For me, I knew nothing about VC early on.
(02:43):
Was a tech person and then found out about itand broke in later in my career.
But excited to go deep and learn about you andyour background.
And again, once again, welcome to the show.
Yeah, thanks so much for having me.
So should I start from the beginning or?
Yeah, let's start from the beginning.
Let's hear, you know, where you grew up, whereyou studied and, and you know, and you started
(03:06):
a couple businesses and then became aninvestor.
So let's, yeah, let's hear whatever you'reallowed to share.
Yeah, so I grew up born and raised inMinneapolis, Minnesota.
So mostly in the suburbs, but was downtown fora bit.
It was a great place to grow up and definitelyfeel like I have Midwestern roots, but I was
(03:32):
always eager to like seek new frontiers andfind new experiences.
And I decided to go to Duke for school.
And I remember, going, we've been in Minnesotaand seeing like the brochure for Duke and
looking at it versus like Ivy League, it justseemed like a very innovative school, like a
school that had to be a little scrappy to getahead versus some of the established Ivies.
(03:58):
That always really appealed to me.
And then when I was at Duke, I studiedeconomics and always wanted to like work in
investing and did my summer internship atMorgan Stanley on the sales and training desk.
But my senior year, I was the president of thestudent union.
And there I really had this opportunity torestructure the organization and run it as a
(04:19):
business at a million dollar budget, largestbudget on campus.
And I always joke that my first ventureinvestment is we seeded the record like
recording studio in, at Duke, which are, thefirst album was like, what's that guy's name of
(04:40):
like, like one of the, like a famous artist is,did like, did a song on that album.
So I was like, that was my first like VCinvestment organization that I was managing
that had all these different subcommittees.
I So you
kind of seeded the production of an album?
Or or did you see the studio?
Studio.
Oh, wow.
(05:00):
That's cool.
Yeah.
It was and then they made their first album.
Mhmm.
I wonder which artist it was.
Was it TI or No.
TMI's from Atlanta.
Right?
It was the guy who did, like, waiting for myplane to come.
Like, why am I blinking on it right now?
He's the guy who walked across the country,like, barefoot, recently.
(05:24):
Oh, I don't know.
Maybe we'll get some help from the audience aswe try to Oh,
God.
Blanking, but
I'm
sure it'll come to me like I have.
Yeah.
Like that.
So I graduated in 02/2008, and during my senioryear, had this offer to go to Morgan Stanley,
(05:46):
and I took a class on VC and entrepreneurshipmy senior year, and the other thing that was,
it was kind of like a weird coincidence,everyone was going to investment banking and
consulting, except for this one guy who hadtaken a year and his high school friend had
founded this company called Box and he was theCFO and he was like, just trying to finish up
Duke or whatever.
(06:07):
And we'd have these guest speakers come in andhe asked these like really specific questions
and like all the rest of us were like, oh,like, you know, who, like no real context.
But anyway, so that was this guy named Dylan,who was like one of the co founders of Box,
which I-
Oh, like box.com?
Yeah, yeah.
Oh, wow.
So he was in my senior year VC andentrepreneurship class.
(06:33):
And then I, you could sort of see the likemarket turbulence at that time.
And I decided that instead of going to MorganStanley, was going to work at McKinsey instead
and in San Francisco.
So I joined the week that Bear and Lehmancollapsed.
Sure.
And ended up doing like all this cost cuttingand liquidity stress test for banks and cost
(06:56):
cutting across Silicon Valley and, you know,like met different, it was like a very like
dour time in the And Bay I came out of that in2010, I guess, after my like two year period
and decided to do a third year.
And I saw this project on the pipeline to workwith the government of Pakistan to reform its
(07:18):
education system.
And I was like, all right, that's totally weirdand different and unlike anything I've ever
done before.
And I'll do this for two months and then I'llcome back and work in tech.
I ended up staying for eight months and it wasthe fastest reforming education system on the
planet.
And the senior partner asked me if I, he wasthis global education system expert, and he
(07:42):
asked if I'd like to be a chief of staff atPearson because he was leaving.
And I was like, all right, that sounds cool.
Like, I'll get to live in London.
And I'd never like thought much about theeducation industry, but, you know, it seemed
like a great opportunity.
And I thought I'd be there for a year.
And then I ended up staying for five and a halfbecause I had the opportunity to found
(08:04):
Pearson's corporate venture capital arm.
Oh, wow.
That's great.
In EdTech and education companies all over theworld and kind of set the strategy from the get
go, made the first investments, like set up theinvestment committee and got to do that full
stack.
And then also at the same time, saw Pearson'sLP investments and M and A activity globally,
and really did a lot of work on what the futureof education looked like and how the markets
(08:29):
were developing.
And one of the papers that I wrote at that timewas called An Avalanche is Coming Higher
Education and the Revolution Ahead thatpredicted the rise of Coursera and MOOCs and
the unbundling of the higher ed sector.
And that's ultimately, you know, what I namedmy firm after was that analogy of mass
(08:52):
disruption.
So I left Pearson, it's probably been like fiveyears now, five or six years, and I founded
this company called Delivery Associates withMichael, who is my mentor from McKinsey and a
couple other people.
And we work with governments to drive bigreform programs and deliver technology, never
(09:16):
raised any money, and now have 160 peopleprojects all over the world, profitable,
growing, and I wanted to get back into earlystage venture and be an investor.
And so I started to invest my partner dividendsand proceeds into LP stakes in different funds
(09:41):
where I really had conviction around a sectorand then started making angel investments that
I then warehoused and turned into the firstfund of Avalanche BC.
Yeah, no, that's great.
What are some things that you learned?
I'd love to double click a little more on justbuilding delivery associates.
So like how did you ideate the MVP and thenwhat's really challenging and what people don't
(10:07):
really get to all the time is a series A.
So how did you really scale?
What was the scaling factor that helped you tokind of get from bootstrapping and maybe, you
know, first customers to really hyper growth toget to the next really serious milestones of
product market fit?
Yeah, so Delivery Associates is based on thismethodology called Deliverology, which is a
(10:35):
framework for how you get governments todeliver results.
And when I was at McKinsey in Pakistan, we wereapplying that framework to the government
there, and it ended up being the fastestperforming education system in the world from a
low base.
And so ministers from around the world werecoming up to me and Michael, the senior
(10:57):
partner, and we're like, how can we replicatewhat you did in Pakistan to our countries?
And Michael, you know, who was the seniorpartner had done this before in The UK and
developed VIP.
And so we had, there was definitely productmarket fit because, you know, governments need
to deliver.
This was a method that was developed within theBritish government originally, and was about
(11:21):
productizing it and commercializing it, andthen putting together the organization that
could go win contracts.
And for us, I mean, to your point about theinflection point is we got maybe like two years
in a really large contract with a governmentthat was like multi year, multi million, and
(11:45):
that allowed us to invest in our systems andthe capacity to go out and win a bunch more
contracts.
And the sales cycle is so long to win thesethings, but once you do, and assuming you like
do a really good job, then you can win the nextone.
(12:07):
And the market is, it's like small, get to knowyou, they know you're not going away, like you
build a reputation for your work.
And that was one of the biggest things that Ilearned that I bring to the entrepreneurs at
Avalanche is like, I've seen that like, can, Iwouldn't say like, yeah, I mean, struggle for
like a long time, like three or four years, butassuming that you don't give up and you really
(12:29):
are focused on like what your customer wantsand delivering a really good customer
experience, you'll hit escape velocity assumingthat there's a real need there?
Yeah, that reminds me.
So there's a guy named Deb Neil.
He is in Singapore.
He founded Decacorn BC.
I think part of it is like his own personalwealth as like an evergreen fund.
(12:50):
But one of the companies that he launched whichwas really successful was and he had a
liquidity event.
But what he did was he had one customer, Ithink it was in the Southeast Asian government,
and they needed like an insurance system.
And there was a bunch of legacy systems outthere, but because he was a small company, was
(13:10):
able to kind of like, just kind of buildexactly what they needed.
And then I think they became so happy that theyreally marketed for him, especially if you can
build that trust.
Because most vendors, I mean most softwarecompanies, you get kind of a package and then
outside of the package, there's somecustomization.
But, you know, when I worked in B2B SaaS, thechallenge is like, especially if you work with
(13:34):
a vendor like that, there's a lot of likethings on their pipeline, but they're not
planning to release those things until maybelike next year or something like that.
So you're kind of beholden to like the road.
You have your roadmap, but your hands are kindof tied because that software platform, they
have multiple customers.
So they're kind of, you know, managing abacklog of like multiple things.
(13:55):
But I think to your point, if you can get thatfor it sounds like this is what you did.
You had that first anchor customer where, youknow, they they were really happy.
And then I think once you build that software,can probably resell it.
And then, know, you have the budget, so you canprobably invest in sales and more tech
resources to kind of add product success, I'massuming.
Right?
Yeah.
And then you, you know, hire smarter peoplethan yourself and, like, the different
(14:19):
verticals, and then they create you know morevalue and it kind of compounds.
Yeah and then did you end up did you end upselling that company or is it just operating on
its own now and you kind of hired somebody tokind of run it I guess, or?
Yeah, so one of my partners is the CEO and heruns it, I'm on the board, still a shareholder,
(14:42):
but yeah, operates more or less without my dayto day.
Yeah, no, that's so amazing to see that youwent through that experience because there's
just so much wisdom that you can hand off toportfolio companies, but also portfolio funds,
right?
So tell me how that experience has been beingan emerging LP.
(15:05):
Really appreciate all the support that you'vebeen doing, obviously with my ecosystem too,
but what are some things that you've beenlearning as kind of being an emerging LP and
now kind of building your firm as well?
Yeah, so I am a big believer in theseavalanches, as you say that I write out in
obviously the future.
(15:25):
So like my first LP investment was in a fundcalled Noetic Fund out of Canada that was
investing in psychedelics.
And my thesis there was like psychedelics asmedicine is going to happen.
And I wrote out this thesis and then I guess Ihad like found somebody who was starting this
(15:46):
fund at the exact time and invested in it.
And one of the things that I think has been agreat innovation in the ecosystem over the last
five years is like, I wrote a 25 ks check,which, you know, it's not like, when I was
starting my career in 2000 and in SanFrancisco, like no one's gonna take a 25 ks
(16:10):
check into their And fund, now you can be an LPfor the size of like a small angel check and
gain exposure to a sector that I'm like, I'mnot an expert, but these other people are.
And I'm, you know, it's good to get thatexpertise and exposure without having to do it
(16:31):
yourself.
Yeah, mean, it's essentially like an indexfund.
And then I think if you have, you know, acohort of all these funds, it's an index fund
of index funds, right?
So that's kind of the way I've been looking atit.
But, you know, you can either hire somebody togo deep on psychedelics, or you can try to
figure it out yourself.
(16:51):
But then there's still the whole process oflike taking that company to investment
committee, where like, if you just invest intoa fund, most of those funds have co investment
rights.
So you can, can, you know, not only do you getexposure to that sector in a risk diversified
way, but they can also bubble up specific dealsif you want, you know, if you want to double
down and actually have more of an exposure.
(17:13):
So, I think that optionality is reallyexciting.
And, and for me, you know, with our fundcohort, know, the next cohort we're gonna have
somebody that only focuses on quantum.
We've had a few psychedelics funds.
So I think for me, it's really cool to havelike these mini experts in these themes.
And to your point, it is accessible these days,especially the smaller funds.
(17:33):
Obviously, when you're looking at funds thatare all like Fund IV, the minimum is going to
be much bigger, but still just kind of gettingexposure.
It's a great learning to be kind of an angelLP, so it's definitely exciting.
John Robinson, who's on the call, he's he'sactually backed.
(17:54):
He's a buddy of mine, but he's actually beeninvolved in a lot of funds as well.
So been been a super active LP.
Hey, John.
Hey.
Yeah, so tell us some.
So and then on the on the early stage directinvesting side, what are some learnings that
you you know, because you kind of built thatangel track record, and then kind of evolved
(18:15):
into, you know, getting into your first close.
What's some advice that you would give topeople just starting out, especially with the
landscape right now with macro indicators?
What would you recommend?
Mean, the feedback I'm getting is, it's a goodtime to be a founder, right?
I mean, it's if you're gonna be able to closecapital, know, do it now.
(18:35):
I would assume that's the same thing as anemerging manager as well.
And I'd also assume it's just people still haveto deploy capital, right?
So fund to funds and LPs for their job, theystill have to invest.
But that's just my standpoint.
We'd love to hear some of your thoughts onthat.
Yeah, you know, I think one of the importantthings to ask yourself, no matter who you are
(18:59):
or what you're doing is what's so special aboutyou and like, what's unique about you and
what's your edge and why are you doing thethings that you're doing?
Because I think that, you know, you want to be,you know, successful, especially in
entrepreneurship and investing, it's so hard,like it is so, we're playing the most
(19:21):
competitive game on the planet.
And so you have to have something that is gonnalike tip the odds in your favor.
And the reason I didn't do direct investingpsychedelics is because I'm like, I'm
interested, but like, I'm not gonna tip theodds in my favor, but I invest in like ed tech,
future of work companies that I've seen the usecase for the company that I built, like things
that I really know and like, especially in edtech, I it's, I can be like, Oh, well, I can
(19:48):
introduce you to this person and this personand this person.
I can actually tilt like people like give, belike, all right, well, I can invest my money
and I can tilt the advantages in your favor.
And I think that in terms of likeentrepreneurship, like starting delivery
associates, like I'd already done, had thislike track record of doing the methodology and
(20:12):
having a bit of a reputation in it.
And so I think that you have to find thingswhere you can tip the odds.
And it seems like it just, I think when youdon't try too hard, it seems like all these
different switches in your career just seemedpretty natural, right?
(20:34):
And I think it seemed like it was a funadventure as you made all these changes, right?
Like the education project in Pakistan, you'relike, why not?
It seems like a great opportunity.
And I think having a positive mindset is whatopened up all these other amazing opportunities
where you got to really build corporate VC andalso kind of build an LP practice and you don't
(20:56):
always get those kind of opportunities.
Yeah, it's
a lot easier to connect the dots going backthan you're like, like I remember people were
like, why are you like, the people who are inPakistan are dying to go to San Francisco.
Like, why would you go the opposite?
Like, one thought that was, that was a goodidea.
(21:18):
I mean, that's a piece of career advice thatI've given.
I mean, one of my first jobs was in theMidwest, it was in Iowa.
And it was a really good company, know, I got Ibuilt some really good technical expertise, but
I think because it was in Iowa, and nobodywanted to go there.
They treated me really well, like I had a lotof perks and but you know, other people
(21:38):
probably wanted to go to like the moreglamorous cities.
So sometimes there's some edge in going tothese less desirable states or regions.
I know some people that have gotten some reallygood jobs in BC, but they were in kind of like
the middle of nowhere, but otherwise it'd bedifficult to break in or even be an LP.
But like they need they need talent and they'rewilling to kind of make it worthwhile for some
(22:04):
people, you know, the best I can.
So it's kind of kind of interesting.
But yeah, that was that was like a lifelearning for me just kind of being flexible on
on that kind of stuff.
For me now it's more difficult right now that Ihave a family.
I'm a little more stringent on like locationnow.
But I think early in your career, it's it'smuch easier.
(22:24):
So yeah, definitely.
Yeah.
What are some high level trends that you'reseeing?
We talked about MOOCs, and we talked about kindof the future of education.
What's some of the hot theses that you'rethinking about now as you kind of write your
next submittal on your blog?
I have a draft for nobody wants to be like, Idon't wanna be your boss or like, nobody wants
(22:50):
a boss.
I think it's like rise of like, some people arelike creator economy, or like freelance
economy, or like the sort of like Dow movementof being like, okay, these like hierarchies and
management theory is maybe not how people wantto engage, especially in like the knowledge and
software sectors in the future.
(23:12):
And I think that that shift both culturally andlike having tech to enable it is really
powerful.
Yeah, I think it was Footwork.
I forgot the fund.
It's a fund called Footwork.
They're on the West Coast, pretty well knownfund, but they wrote a blog recently on just
(23:34):
leverage that employees now have, like theshift of power is now coming to the employees.
It's obviously they have a much better say.
Think some of that might shift a little bitlike the economy.
But I think just the way that Gen Zs look atemployment, I feel that's different than the
(23:58):
millennials.
Right.
And I think people, if they're not happy,they'll to your point, right, just try to build
something on their own or be a creator or haveside gigs as well to maybe augment their
current role.
So I think that's definitely a thing.
But I definitely think, know, especially withthe great resignation, I'm assuming that's
(24:20):
probably a catalyst for more educationplatforms too, right?
Because people are kind of taking a break andmaybe re enabling skills that they didn't have.
Is that something you're seeing as well?
Some of that for sure.
I think the biggest thing that COVID has doneor this period is actually in K-twelve where
(24:45):
parents have pulled their kids from the publiceducation system and done homeschooling, pods,
micro learning, and they have not come back.
And so now you're seeing more of these likeeducation savings accounts of like how can
governments give, I mean, everything's kind ofpoliticized, right?
So like voucher being a dirty word, butbasically like direct subsidies for parents to
(25:05):
be able to make, to choose what they send theirkid, like where they send their kids for
K-twelve.
And then I think like Gen Z is kind of likewizened up to student debt and they've seen
millennials go through, know, take out theseloans, not be able, not have them translate to
like, and get a return on investment into theworkplace.
(25:27):
And they're like, well, wait, I could, youknow, like learn web three for free and get a
job being a community manager and then buildthis network and navigate these online
communities.
And so I think that like I'm not investing inany companies that augment the existing
secondary system.
(25:49):
You know, like you're looking for things thatare going to completely transform it because I
don't think that it can be reformed from theinside.
Yeah, what are your thoughts on just gifted andtalented programs?
Because I feel like it seems like such anexclusive capability to get access to that.
And I think there's been some movements now tomake that more accessible.
(26:10):
But I always felt that they should just havethat every school.
They should have kind of like a gifted andtalented department because especially in New
York and as you know, right, like the kids haveto go like somewhere on the Upper East Side and
they have to test into it.
But I feel like that that is not as enablingto, you know, because there's probably a lot of
(26:31):
people that are gifted and talented, there justisn't enough room, right?
So I feel like they're trying to make that massadopted.
Then another thing I would ask is what isgifted and talented?
Like what somebody believes gifted and talentedis maybe different than somebody else, right?
So it's like we're just following this personthat has defined that you're gifted and
(26:53):
talented.
So I don't know if you have any strong thoughtson that and just kind of how that plays into
the educational system.
Well, I think when you open access up topeople, you're like, well, why do you have to
go to the Upper East Side to go to some likegifted and talented program?
And I think, you know, one of the big companiesthat just got raised a big round was synthesis
school, which is like the unified-
Is it Elon Musk's school?
(27:14):
I think it's basically like they took the techand the pedagogy and then have built a new
product off of it, But you're like, all right,I mean, it's kind of inaccessible right now
because I think it's around $200 a month ofprice point, which is pretty high for most
parents, but you're
like,
anyone can go join that, right?
So like, you don't need to be gifted andtalented, you just need sign up.
(27:36):
And so now as long as you have access to acomputer and, you know, your parents can pay
out of pocket or this is where the state couldbegin to provide subsidies, The world's your
oyster and you can learn with kids all over theworld and you can pick your own, you know, the
things that you're interested in and yeah, likegifted and talented traditionally used to mean
(28:02):
probably that like, you were good at math andlogic and like maybe we're a good writer.
And I mean, there's lots of people who aregifted and talented at TikTok videos and coding
experiments and so many niches.
Yeah,
I mean, thing that came across my mindrecently, was Kevin O'Leary, he posted
(28:24):
something saying that he used to think it wascritical to study computer science or business.
But he specifically said, the skill of beingable to communicate a complex message in like
fifteen seconds is going to be super important.
And I've kind of gone through that experiencerecently because I submitted something to an
(28:48):
accelerator and I struggled for a long timetrying to say everything that I needed to say
in one minute as a video because it reallyreally makes you concise and precise.
Have to really clearly cut a lot of the noiseand you might have to skip some screens when
you're demoing something but it really reallyis you know, inspiring because it just kind of
(29:12):
forces you to really deliver a message.
I can't imagine how difficult it would be tokind of do a startup pitch in fifteen seconds.
Yeah.
But even a minute, minute actually, dependingon how you look at it, it is enough time to
kind of deliver the one liner and deliver theproblem.
But I think that's still a difficult skill thatsome people might struggle with, because people
(29:35):
might be super detailed, and they want to shareall the nuances.
And you kind of miss really the main point.
And I think that's kind of the balance.
So I think that's kind of a skill that'sprobably just as important as being an
engineer.
Because if you're building something sobrilliant, but nobody can really understand who
the customer is, then it's it really is kind ofa lost cause.
(29:58):
Yeah.
Well, maybe you can, know, I know we got a fewmore minutes.
Any advice you would give to people that arestarting their career transitioning from maybe
a non finance degree to venture or privateequity?
That they're trying to get into venture privateequity?
(30:21):
I think that quality of people really matters.
So really research the people that you want towork with, and then think about how you can add
value to them, and then tailor your approachand outreach to the people you want to work
(30:42):
with, and build a relationship with them overtime.
And really think about like what is the rolethat you're looking for and like do be
basically doing that role before you kind ofever ask like ever ask for a job or someone's
time like and I think you'll be able to standout from the crowd and develop a relationship.
(31:07):
Like I'm surprised at how many people, or sortof the lack of people who really do like a
tailored, like high quality ask or think aboutkind of like adding value or, you know.
Yeah, no, I agree.
How important, know, I just spoke with somebodyearlier this afternoon and, you know, their
(31:31):
feedback, they kind of had a similar journey toyou and I where they came from kind of a non
traditional path, but they were saying thatkind of the banking financial modeling isn't as
important, but it's really kind of therelationship building and really
thoughtfulness.
Would you agree with that?
Guess are there any specific hard skills thatyou would recommend people to brush up on if
(31:54):
they're trying to break in for the first time?
Has that changed?
Because I know before it might still be thecase.
I mean, is still kind of a pedigree focusedindustry, but I do see that changing, but would
be curious to hear your take on that.
I think as you go, so when you start at preseed, like there's a lot more like or seed
(32:16):
because there's a lot less out there.
You don't have to be so like analytical andprescriptive, but as you get farther up, it's
so analytical and so precise.
Also when you're managing other people's money,like the bar is just, and standards are really
high.
And so I think more than it even being like apedigree point of thing is like, I see people
(32:40):
who maybe don't come from the, don't have thepedigree, but it's not really like the pedigree
or not, it's like the standards andexpectations, like going through McKinsey, you
were ground down, like every little detail hasto be right structured thinking, you know, it
was a more intense training program thanundergrad.
(33:01):
And I don't think it can be like understatedhow important that level of precision and skill
is, especially if you're like managing otherpeople's money at scale.
So yeah, I think it's good that there's peoplefrom different backgrounds, but also just the
bar is high for a reason, you know.
(33:22):
Yeah, I'd like to take a couple minutes also totalk about portfolio construction, right?
So I think that may be an interesting topicthat I haven't talked about in a while.
So what you know, how did you go about yourportfolio construction, thinking about how many
checks you want to write, know, the sector, thestage and then kind of, you know, what your
goals were for first close?
(33:44):
Any advice you would give to someone who's, youknow, maybe had an angel track record?
And now they're like, wow, I think I'm going tostart thinking about maybe getting some first
angel checks into, into my fund?
Would you recommend them building a frameworkaround portfolio construction?
Well, my first fund was small, it was like amillion dollars.
(34:07):
I kind of anchored it and I did 20, it wasn'ttotally precise, but like 25 ks checks and I
did 36 unique investments and then two followons.
And
the check sizes were like, I wanted reallydiverse.
(34:32):
I wasn't going into hot rounds, like I wantedthe valuations to be low, which has turned out
to be good.
I wanted to get a lot of reps in because Iwanted to be able to get, you know, to learn
and grow.
And then I was also offering my LPs adiversified portfolio.
(34:53):
So I can't remember exactly what the number is,but it's like, at least have to have 20, maybe
25, maybe even like ideally 40 investments ifyou're gonna hit the power lots, I have one
really gonna be a winner.
Sure.
And so I wanted follow that.
What was the range that you were trying to stayin for evaluation?
(35:18):
Were you trying to stay in like this six under10,000,000?
6 to Pre
seed, I wanted to do definitely under 10.
I just did the analytics on this for theportfolio and my seed post, my average pre seed
post money valuation is like 6,600,000.0.
Okay.
And my average seed is just under 20.
(35:40):
So
I feel pretty good about that, all thingsconsidered.
Did you do any cross border investments?
I don't know if you know Kalsum, but yeah,she's she knew.
So she was in my one of my past cohorts, butjust a trend that I learned from her and just
other VCs that are investing in Africa, India,Southeast Asia, you can get like an amazing
(36:04):
company and like the valuation is, you know,sometimes I mean it's much higher now, but
probably two years ago you get like a rocketship company for like, I've seen some of them
for like 4 to 6,000,000.
Now it's now it's at par, you know, and you'vegot Tiger Global investing in a lot of deals.
But did you you do any cross border deals kindof in emerging markets to kind of learn about
(36:29):
those sectors or?
Well, I cut my teeth when I was at Pearson inemerging markets.
Yeah.
And like I've known Kelsoon or known of hersince 2011, because I lived in Pakistan.
And honestly, like I've looked at people in TheUS like investing money in emerging markets and
(36:52):
I'm like, you have to have risk, like thosemarkets are tricky.
Like it's tough.
It's not like, I think that people haveunderestimated some of the risks there and I'd
much rather be an LP in fund, someone whoreally understands those markets, knows all the
people, can spend time with the entrepreneursthan people who are just like, hey, this looks
(37:14):
like a cheap deal in Pakistan or in Nigeria orwhatever because like, know, there's a huge
information.
You're shooting blind, yeah.
I think that's good too because if you investin someone talented like Khalsum, you know they
have a lot of these emerging managers.
They don't have that rigor and really, reallystrict discipline and you know just really,
(37:39):
really strong vetting process, won't they won'tget to their next fund.
So I think that's what gives me confidence inthe fund managers.
And yeah, you're right.
I I would be shooting blind, like just tryingto get some arbitrage with a direct deal.
What I have done is like, she's someone thatwould be a really good co investor for me
(38:01):
because I'd like, all right, I'm an educationor future work specialist.
You know the market super well.
So we'd be really great, like complimentary coinvestors.
So I would always try and like co invest withon the same terms as an investor like that.
Yeah.
No, absolutely.
I've done that a few times with some LPs too.
And I would say that's been that's been agreat, you know, piece of feedback that I've
gotten from people just kind of building thatco investment relationship.
(38:24):
And then if you've done like three or fourdeals together, then sometimes those people may
want to just support you and just come intoyour fund as well.
So that's also been kind of a win win.
Have you used the tool?
I'm a power user of tactic.
I'm assuming I don't know how long Tactic hasbeen around, but I'm assuming like when you did
your early portfolio construction, was probablylike all in Excel.
(38:48):
But I'm like a power user.
Don't know if you've used Tactic, but it's likeone of my favorite products now.
Yeah.
Yeah.
I really like too.
I actually have both an Excel model and thenI've been on on Tactic.
Yeah.
So yeah.
So I'm pretty good friends with Anubhav and I Idid like a live stream with him like two, I
(39:09):
think last week because I just wanted to learnall the new enhancements that he had.
I was like, you know, I might as well justshare this with everybody.
So we just kind of did it live.
So it got me up to speed and I just kind ofshared it.
But I think that's really exciting with Venturetwo.
There's just a lot of new tools that people canuse to kind of, you know, start these funds
(39:30):
much faster than before.
I think before it was a lot more opaque andthere's a lot more content and community around
it, which I think is enabling a lot morecapital coming into the funds, which
essentially will be going into the portfoliocompanies as well.
So that's also
I think is good about it is that it's basicallycommoditizing a lot of the back end part of
(39:54):
venture, but it does put the onus on, I think,fund managers to actually be able to add value
to the companies, because anyone can now like,you know, use that no code tool and come up
with a portfolio.
So like, that's not the hard part.
The hard part is building companies that makethings that people want that are going that
don't fall apart because of co founder likeDynamics or a bad board member or all the
(40:21):
things that are not commoditized.
Yeah, no, that's a good point.
Yeah, I mean, I think when you have too muchautomation and you have too many AI portals
that are serving deals up, then you becomeobsolete, right?
So I don't think that will happen anytime soonbecause I think there's still an art to using
(40:42):
your judgment, right?
Because I think beyond the numbers you'relooking at human beings, And you're kind of
judging their character and deciding if youwant to spend the next seven years still on
that journey with them.
So sometimes just the algos may not always beable to pick that up I would say.
So never say never but
(41:03):
Or the problem is it becomes like sleepy captable money you know, because like, people who
are investing based on an algorithm are notgoing to pick up the phone on like Saturday
night when your CTO is thinking about quitting,you know.
Yeah, sure.
Yeah, no, absolutely.
I think those are, I mean, it's great when thetimes are great, but I think, you know, the
(41:27):
value also comes when there's tough times andthey can have somebody to call and kind of get
through that because you have a vested interestin them being successful as well.
Yeah, exactly.
Yeah.
Well, you know, I really appreciate all yourtime, you know, maybe I'll open it up for a few
questions if people have any.
So anybody on the call have any questions?
There was one in the chat?
(41:50):
Well, someone, won't say who it is because itwas the direct message asked what is adding
value to me?
Oh, okay.
And I think it was like in what this personasked the question when we were discussing, you
know, intros breaking into the sector.
I think sourcing a deal, like a good deal isalways adding value.
(42:13):
It's always value additive.
Like not just like a random one, but if you'relike, oh, I really like saw this company, think
it's really interesting for these reasons.
Like that's always a topic that like I'minterested in that I'd engage on.
That was helpful.
John, I know you pinged me asking if you couldask a question, you got a question?
(42:34):
Yeah, thanks Joel, and thank you very much forthis talk.
This has been great, Caitlin, appreciate it.
I am kind of in a situation where I was tryingto get active with Joel's help.
I've been networking a lot.
I was trying to get I have an Angelistsyndicate and I was trying to kind of get off
(42:55):
the ground.
And I made some connections.
But then, you know, I to I got laid off fromwork and I had to find a new job.
So I got the new job.
That's good.
But I just, it's hard now to kind of dice mytime up in the way that I want to, to give the
attention that I need to, to my VC connectionsand the people that I'm the startups that I'm
(43:17):
working with.
So I was just wondering if it's more like atime question.
Was just wondering if you could, any insightsyou might have on just how to split time if
your full time job is outside of VC?
I think it's incredibly difficult.
Like, think about time management every day.
I'm like, how do I manage time?
(43:38):
I think it's probably quality over quantity.
So like narrowing your focus and your world.
And so for me going even between from fund oneto fund two, I kind of narrowed the focus of
the companies that I was interested in and thenqualified for LPs in my fund and really was
like, all right, I'm gonna go after like thecompanies that are 95% likely to be in my sweet
(44:06):
spot and only take those meetings.
And then for LPs, I'm like, okay, is thisperson really like, do they already really like
me?
Are they interested in my sector?
Do they write checks?
And like only take those meetings and not chaseafter like all of the other like noise.
So I think it's really about focus and thenstrictly prioritizing what's gonna move the
(44:27):
needle for whatever your objective is.
Yeah, that's really good advice.
Thanks so much.
Appreciate that.
Yeah, cool.
Any any other questions?
We'll take maybe one more and then give Caitlinher time back.
Hey, Joel had one question.
Sure.
Hi Caitlin.
Thank you for your time this evening.
(44:48):
As you were getting started in launching yourown fund, did you ever invest through SPVs
early on?
I have invested through SPVs.
I will say like, oh, it's not true when I didlike, it's not totally true, but whenever I was
(45:09):
like invested in Angel List SPV where I didn'tknow the founder, like I didn't have a
connection with them before, it's kind of justbeen like a financial investment almost just
like buying Microsoft stock on Vanguard orsomething, it's not like anything exciting to
me and I feel like I get no information abouthow the company is doing and so.
(45:34):
Well, guess to be more clear, I meant it as didyou start an SPV on your own and use that to
fund the business?
Build a track record?
No.
Okay, got it.
So did you go straight to like starting yourown firm basically when you were ready?
Yeah, I started at Angel Invest my own money.
(45:54):
Then like one of the things that's great aboutstarting a successful company is that you then
have, you're like, you can go to your cofounders and like other people that you've made
money for or whatever and get them to likeinvest in you.
I mean, I think that it's, I know thatdifferent people have different models that,
like there's some people who are very active onTwitter and have these big like marketing
(46:18):
presence, like that's not me, I'm like morelike introverted, but like deeply expert in
what I do.
And you know, I kind of went to my friends thatI knew this could be like a good fit for were
high net worth individuals.
(46:38):
And like, one of the things that I see now thatwasn't the case when I was young is like people
who are really young trying to break into VC.
And I'm like, I can do it now because I'm in mymid thirties and my friends are like partners
at managing directors at banks, partners atconsulting firms, like they're like wealthy
(46:58):
accredited investors.
Like there's no way I'd be able to do that whenI was 25, you know?
Got it.
Yeah, one more thing that I'll, oh, go ahead,Manveer. Had
Had one more anecdote to add to that, but goahead.
One final point just to get, I guessclarification is your, would you, I heard you
mentioned EdTech multiple times, would you saythat's your core emphasis?
(47:20):
I'd say it's the area that for better or worse,I know the most about.
And I say for better or worse because I bring,like you bring your full bias of like, well,
that won't work.
Like I've seen this, it's failed.
And so sometimes it's good to be like a littlebit naive, I think about a sector.
(47:42):
So, but that's one that I just like mentioned alot because it's very easy for me.
Got it, thank you.
One thing I was gonna say is, I spoke to an LPlast week and you know, and I've heard this
too.
I mean, LPs through the diligence process maywant to talk to portfolio companies to kind of
(48:02):
hear what like the portfolio companies sayabout the VC.
But you can't really do that if you just, youknow, did these small checks into angel list
because you can't, you know, you haven'treally, you can't really number one contact the
founder and they won't have anything to sayabout you.
So that's the benefit of kind of justpersonally kind of like what you did and I've
done the same thing, kind of personallyinvested on the cap table and hopefully those
(48:26):
founders you built enough goodwill where youcan get in at a decent minimum.
Yeah, yeah, cool.
Awesome.
Well, hey, thank you so much, Caitlin.
I know you're super busy, so I really, reallyappreciate you being generous with your time
and sharing your story.
We all learned a lot, so appreciate it andappreciate the friendship and have a good rest
(48:46):
of the week.
Hopefully, hopefully the weather is continuingto stay pleasant for the next few days.
Absolutely.
Thank you so much for having me on.
This has been great.
Yeah, absolutely.
Take care.
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