November 19, 2024 • 59 mins
Joe Grover sits down with Jake Bengtzen, an innovative entrepreneur and the founder of Zipper.
They discuss the multi trillion dollar health care problem, the crazy premiums, extra fees and how Jake was on a mission to solve it, using his company: Zipper.
After 92 pitches, 7 investing angels, 18 months of grinding and paying himself only 3 times, he eventually hit rock bottom.
Jake realized the healthcare problem was too big to solve and it was time to shut down Zipper.
Jake shares, “There are a lot of people who choose unhappiness over uncertainty.” What matters most now, is what you are going to do after failing.
Growing up, he was exposed to the realities of entrepreneurship by his father and grandfather, both of whom started and ran small and medium sized businesses. As a young full-time college student, Jake networked his way into an entry level sales position at an up and coming Utah fintech startup called Finicity. It was an incredible journey where he took on various roles, including that of Chief of Staff. After the company was acquired by Mastercard for just under $1 Billion, Jake started contemplating making his own entrepreneurial jump.
This led to starting Zipper Health, a healthcare fintech startup focused on lowering the cost of healthcare for individuals and families. Rising healthcare costs is a problem that is near and dear to Jake.
Jake is a husband and father to 3 kids (with one more on the way at the time this episode was filmed).Outside of professional pursuits, Jake got hooked on triathlons about 10 years ago and has competed in Ironman. He is adamant about qualifying for the Ironman World Championships in Kona, Hawaii. Jake also loves playing pickup basketball, fly fishing, and golfing.
This episode was recorded on November 8th, 2024
-Links-
For Jake Bengtzen:
https://www.linkedin.com/in/jake-bengtzen-0a8ab365/
For Joe Grover:
https://www.linkedin.com/in/joelgrover/
#entrepreneurship #realfword #startups #Failure #zipper
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Welcome to the Real F Word.
I remember when I firstlaunched the podcast, it was
interesting because everyonewould reach out and say, hey,
you really need to talk to thisperson, or you really need to
talk to that person, and acouple of people, I think on
LinkedIn, said, hey, you shouldreally talk to Jake.
Jake has this experience andit's fresh right, it's only been
(00:23):
.
Speaker 2 (00:23):
It's very fresh August 19th, okay, probably two
and a half, almost three months.
Speaker 1 (00:29):
Three months and so like.
This is an experience thatyou're just coming out of
starting a company, raising alittle bit of capital, building
something that was meaningfuland making a difference in the
world, and having and you had toshut it down, and so today
we're going to unpack that alittle bit.
But let's let's go back evenearlier.
You spent a ton of time inFinTech, right?
You were like, worked forFinicity and MasterCard.
(00:51):
You were chief of staff, youhad a leadership role there.
Tell me about what led you toyour first entrepreneurial
endeavor.
Speaker 2 (01:00):
Yeah, you know I.
So I grew up in a house wheremy dad was an entrepreneur, my
grandparents were entrepreneurs.
It was something that I wasprivy to pretty early, both the
good that can come from it, butalso the struggles that exist.
Both my grandfathers had prettyrough stories when it came to
entrepreneurship failed ventures, things that went wrong, some
(01:23):
things that worked, and so itwas something that I just grew
up familiar with, and when I wasa sophomore in college, I ended
up going to lunch with thefounder of Finicity for the
purpose of trying to get hisadvice on whether or not I
should study finance oraccounting, and two months later
(01:45):
was my first day on the job atFinicity.
So my foray into a startup andinto this world for myself was
very much serendipitous, and theFinicity journey was really
exciting.
Like you mentioned, I heldvarious roles within the company
.
We got acquired by MasterCard,but towards the end I was chief
(02:06):
of staff, and that's really whenI started to think.
You know, it's great to see acompany start, grow, succeed,
but I want to be in that seat, Iwant to be in that chair.
I want to go through thatexperience, not for the sake of
(02:29):
just being a founder, butbecause I want to solve problems
at that level and there weresome problems that were really
near and dear to me and thosewere the ones that I actually
ended up going and trying tosolve and what else was it?
Speaker 1 (02:42):
It was the problem solving, being in the sea,
making the decisions, leadingthe vision and the strategy.
What else was it that?
What was the allure of doing iton your own versus cause cause?
Finicity was pretty large.
Mastercard is massive.
Speaker 2 (02:54):
Yeah, mastercard is huge.
Speaker 1 (02:56):
You're working for a massive organization and now
you're like, hey, I'm going tostart something from the ground
up.
Speaker 2 (03:01):
I love building.
I love creating.
One of the most fulfillingthings for me at Phenicity was
the ability to talk withsomebody, to hear them express
their problems and to thinkcreatively about.
There's nothing that perfectlysolves that.
How can we solve that?
I think one of the mostfulfilling things for me is
being in a situation wheresomething that I do or bring
(03:28):
changes someone in a positiveway, and entrepreneurship is all
about that.
It's all about how do I go andfind problems that no one solved
in a good way and solve them.
That was the allure to me.
It's not driven by the endresult, it's driven by I get to
wake up in the morning and I getto do something that hasn't
(03:50):
been done.
And there are a lot ofentrepreneurial ideas to me that
aren't exciting at all and it'sbecause they don't encapsulate
that like true, meaningfulmaking a difference.
I think about the quote wheremuch is given, much is required.
All the time I look at thecards I've been dealt Born in
(04:11):
Utah, lived in Canada for awhile, grown up, moved back and
then I've spent time in otherplaces around the world where
you see poverty and people whohave a lot less poverty and
people who have a lot less, andgoing through those makes you
realize you know I've got both aresponsibility but an amazing
(04:32):
opportunity to do somethingreally, really meaningful, and
to me that manifests the best.
In my opinion it doesn't haveto be everybody's opinion.
This is a truth to Jake, asI've explored who I am and what
I like, entrepreneurship is theway that that resonates for me.
Speaker 1 (04:53):
So not to jump to the punchline here, but does your
experience with Zipper, whichwe're going to talk about, does
it change your perspective onentrepreneurship?
Does it weaken your resolve?
Has it made you questionwhether or not, like you want to
do this again?
Speaker 2 (05:09):
Immediately thereafter?
Yes, two and a half threemonths later, absolutely not.
Speaker 1 (05:15):
It took.
It only took you three monthsand you're like I'm going to get
back on the saddle.
Speaker 2 (05:18):
That's amazing In my head actually doing it?
No, there's.
There's um, I'm going to do itdifferently.
I think is is.
Is the the punchline to that?
Uh, definitely, I love.
I love the journey, I love theexperience.
(05:39):
Selling did not make mequestion whether or not.
It made me question whether ornot being an entrepreneur is
what I want to do, but it wasmore.
It came more from like who am ILike, what am I doing?
It didn't come from it didn'tcome from a different place.
(06:00):
It was more introspectivequestioning Is this what I want
to do?
Who am I, what am I good at?
It was reflection, notdiscouragement.
Speaker 1 (06:07):
Yeah.
Speaker 2 (06:08):
It was all introspection, okay, and I'm not
over it yet.
It's not like I've moved on,right.
I still wake up every daywishing that I would have
figured it out.
I don't.
I don't think that feeling isgoing to go away immediately.
Speaker 1 (06:20):
Yeah, so tell me about zipperipper.
Okay, so did you start this?
This idea had been percolatingfor a while, and what's?
What's the problem that youwere solving and how did you get
this thing off the ground?
Speaker 2 (06:33):
Yeah, I think it's helpful to start a little bit
from the FinTech journey.
I started at Finicity having noidea what the world of FinTech
was.
I'm a sophomore in college.
I sit down on the first day andit's here's a list of a whole
bunch of companies you've neverheard of.
You got to call them, you gotto start trying to close them as
(06:54):
deals.
You got to bring them on ascustomers and I remember sitting
there thinking like this mightbe a, this might've been a bad
idea, because I'm a total fishout of water and as I started
getting into it, I fell in lovewith this concept of.
And for those who don't knowwhat Finicity is, there's a
competitor that we had that alot of people know called Plaid.
(07:17):
We did the same thing.
We were the infrastructure thatallowed people to connect their
bank accounts to apps.
So if you used Venmo orRobinhood, you've interacted
with the technology that we werebuilding, and there was
something amazing about howunlocking access to people's
bank accounts where they couldshare the information that lived
there in other places.
(07:38):
You know you could get lowerinterest rate loans, you could
send money to friends, you couldget and bypass a lot of the
fees that existed in financialservices.
That, to me, was reallymeaningful because I saw.
You know it doesn't make sense.
It's hard enough for money tobe made in certain situations.
(07:59):
That why does the place thatyou put it take from it right?
That was something that Ireally fell in love with.
I really enjoyed being a partof.
Well, I started you know, myfamily.
We had kids and you know, goingfrom being a couple where you
don't go and visit the doctor alot to having kids and
(08:22):
complications with having a babyI started to experience a part
of financial services that wasvery foreign to me, which was
the cost of healthcare andseeing how insurance worked and
how so affordable.
Right, the bills worked, yeah.
Speaker 1 (08:36):
Premiums of $1,700 a month.
Speaker 2 (08:39):
I've got a friend who said the greatest trick the
devil ever pulled was convincingpeople that out-of-pocket costs
don't include the insurancepremiums.
In 2023, the average cost for afamily of four just to have
insurance which is the premiumsyou pay monthly $24,000.
A lot of that is oblivious tous because our employers pay it.
(09:06):
It comes out of our paychecksdirectly, and so $24,000 a year
goes to paying for healthcarefor a family of four.
That does not include the moneythat you pay out of your own
pocket before you've even metyour $6,000 or $7,000 deductible
or your $15, know so brokenfifteen thousand dollars in out
of pocket costs and we all feelit, but no one can solve for it
(09:28):
and the costs just go up.
Speaker 1 (09:30):
I've never seen the car, I've never gone to a
renewal right oh, it never goesdown oh hey, guess what I'm
going to save you?
20 this year.
Speaker 2 (09:36):
It always goes up, that is hard like there's,
there's no relief in sight forincreasing premiums, at least in
the existing model.
Well, to talk about Zipper,that was the problem I wanted to
solve.
Speaker 1 (09:50):
Huge problem, billions, trillion dollar
problem.
I don't know how big thehealthcare industry is $4.5
trillion $4.5 trillion.
Speaker 2 (09:59):
And about half of that is funded by the 160
million people who get healthinsurance through their
employers.
It's like that's a big,meaningful problem.
I have directly felt the painof that.
I remember going to a doctor'svisit and it was a visiting
physician and that visitingphysician was not covered by my
(10:20):
insurance.
Yet the location that I went towas my insurance.
Yet the location that I went towas.
And for those who don'tunderstand the dynamic in
healthcare when a bill gets puttogether for you, you're billed
by both the facility and the doc.
The practitioner, yeah, andsometimes One is in network and
one is out.
And one isn't.
(10:40):
Yeah, and in insurance, thecost for something in network
versus something out of networkis totally different.
We got a $1,300 bill and I'mthinking to myself I pay a ton
of money every month for asolution or a product that's
supposed to pay for myhealthcare right, but it didn't.
(11:03):
So so experiences like thatover time led me to digging in
and trying to understand.
I understand, I get the FinTechworld, I understand how it
works.
Healthcare is one of thebiggest problems, and my thesis
was money is the root cause ofmost issues in healthcare, and
and I validated that, but not inthe way that I thought I would
(11:26):
Um, so that was the impetusbehind zipper.
It was personal experiences.
Plus, as I went out and talkedto people, it was ironic how the
financial pain oftentimesmimicked the emotional and
physical pain in healthcare.
That was.
That was absurd to me.
Yeah, still is.
Speaker 1 (11:46):
So what problem was zipper solving?
Speaker 2 (11:48):
We were trying to lower the cost of healthcare for
individuals.
Speaker 1 (11:51):
And how were you doing that?
Speaker 2 (11:52):
There are companies who advertise insurance as being
simple.
It is nothing.
No, it's never simple.
No, it thrives off ofcomplexity.
Do you think that's purposeful?
Do you think it?
Speaker 1 (12:05):
could be simple, or do you think it's just?
No, it thrives off ofcomplexity.
Do you think that's purposeful?
Do you think it could be simple, or do you think it's just
inherently complicated becauseof the way that our healthcare
system works?
Speaker 2 (12:14):
I don't think anybody .
I don't think most people whowork in the world of insurance
or healthcare.
I think the majority of peopleare amazing.
They do things for the rightreasons, I think, over time.
Insurance came about in 1943 asa solution to wage control.
I think the 81 years of boltingon additional solutions and
(12:38):
morphing it, I think that's theproblem.
Speaker 1 (12:40):
It's just like amalgamation of HMOs and PPOs
and HDHPs and HSAs, and FSAs.
Speaker 2 (12:52):
It's a system with a lot of baggage that's tried to
solve immediate, short-termproblems and, as the target has
moved, the baggage of solvingthe previous problem was brought
along to solving the next.
And so we live in a world wherethere's this giant archaic,
difficult-to-change system thatthrives off of incentives that
(13:13):
negatively impact consumers.
And so when I went in, it wassimply put I just want to lower
the cost of healthcare for Joe,for Jake, for people who work
really hard but end up paying$24,000 just to say that they
have insurance when they go tothe doctor's office and they're
paying a copay instead of payingthe price out of pocket.
(13:33):
Like that's it.
I want to lower the costbecause I think that there's a
lot of money that is wasted anduh, and that that was it, like
that was the basis.
I just want to solve thatproblem and the insight was
coming from the world offinicity, like if people can
share information directly fromtheir bank account with an app.
There's a lot of interesting,unique business models and
(13:56):
insights that that delivers,that lowers the cost of
financial services when you goto the doctor this is crazy to
me and you get a service.
Speaker 1 (14:05):
You have no idea how much that costs and if you ask,
which I've done so many times infact, in my background in fact,
my dad worked at a large brokerat the tail end of his career
for 15 years.
And so I kind of grew uptalking about consumer directed
healthcare and so my familiaritywith benefits comes from my, my
(14:25):
, really my even my childhood.
And the reality is, is when youask a doctor right, and I've
done it so many times, how muchis this going to cost?
They don't know.
They don't know the answer andonce in a while there'll be a
range or they'll give you to theoffice manager.
But it is shocking.
It's like going into a cardealership and saying, hey, I, I
(14:46):
, I like that car, I need thatcar.
And they're like perfect, hereyou go, here's your car, and
we'll send you the invoice in 30days and you're like is it 20 K
?
Is it 30 K?
Is it 50 K?
It's, it's, it's insane.
Speaker 2 (15:01):
It's again it's.
It's a.
It's a byproduct of the system.
Yeah, it's again.
It's a byproduct of the system.
Yeah, it's not that that doctordoesn't want to tell you no he
doesn't even know.
But if I'm a doctor and I sayit's going to cost you $200 and
the bill comes back later andit's $300, like how do you view
me now as your doctor?
Yeah, not great.
(15:21):
It also depends on whatinsurance you have, sure, what
plan you have, how much of yourdeductible you've already paid
out.
There's just so many factorsthat play into this that make it
complicated.
It's just really difficult.
Speaker 1 (15:34):
It's a multi-trillion dollar problem.
Was the problem too big for youto solve?
Speaker 2 (15:38):
Depends on what like how you frame the problem.
It depends on that.
How you frame the problem.
It depends on that.
Vcs love big TAMs but, as afounder, part of the journey, at
least from my perspective, waswe need to raise money and
(16:01):
saying healthcare is a $4.5trillion problem.
Speaker 1 (16:03):
it's almost too big.
I want to talk about TAM for asecond, though, because I think
that's a really great insightthere's for many, many years.
Right, it was always likeeveryone would just show up and
it was just like a huge TAM,like I don't really care about
the total addressable market.
I do care about the serviceableaddressable market, and what
(16:26):
percentage of that can I obtain?
And so you probably foundyourself getting really deep
into really understanding what'sthe pocket, what's the corner
of the market that you canservice with your solution or
with your product, and how muchof that can you actually obtain.
Right, and I think that's whenan entrepreneur is pitching and
I'm on the investor side andthey really understand that
deeply.
(16:46):
That to me is a strong signalthat they've done that work to
pare back the problem tosomething that they can actually
address as a startup withlimited resources, and then that
can be a land and expandapproach where they solve this
problem, then you can solveother problems and you can kind
of move to a larger obtainablemarket.
Speaker 2 (17:05):
Yeah, in the throes of trying to fundraise, I did
not think enough from a firstprinciples approach, zipper for
me was I had a previousco-founding experience in an
incubated startup but truly as aas a first time founder, zipper
was Zipper, was it?
I cared a lot about what otherpeople thought and I was
(17:30):
confident in my abilities.
But I was confident in theabilities of people who had
succeeded before and we had somereally amazing advisors who had
raised from top-name VCs in NewYork and Silicon Valley.
And the advice I got pertainingto TAM was like you want a big
(17:52):
TAM because VCs really like abig TAM.
Well, the truth is the VC caresabout your revenue because your
valuation and your success is onwhether or not you get to a100
million a year in revenue ormore.
That's kind of the VC measure.
Tam is just a way to say themarket's big enough where we can
get $100 million in revenue.
Well, there's a lot ofbusinesses who make a lot more
(18:15):
than $100 million in revenue who, when they're pitching
initially, their TAM is in $4.5trillion $4.5 trillion and so
it's a proxy for is there enoughroom here for us to make enough
money to have outsized?
Speaker 1 (18:32):
returns for you as a VC.
That's why the obtainablemarket that answers the question
whether or not it can be $100million in revenue in the next
five years, right.
Speaker 2 (18:40):
In 10 years, are there enough customers who want?
Well, in seven years if youthink of the math, seven or
eight years are there enoughcustomers who will want what
you've got, to the tune of $100million?
Speaker 1 (18:52):
and paying for it.
Speaker 2 (18:54):
That's what they really want, right?
Speaker 1 (18:55):
And you went out and pitched this.
How many times?
92.
Okay, I love it.
92.
How many times did you hear no?
Speaker 2 (19:05):
85.
And it's helpful to get context92,.
If you include the seven angelswho said yes and the 85 VCs who
said no, there were more.
Right, you know more angels andothers that we spoke with.
Speaker 1 (19:24):
Because the angels are the ones that ended up
funding the deal.
No institutional VC.
It was a little too early.
Speaker 2 (19:30):
We did have an institutional VC, but it was.
We believe in you and we'llgive you an angel-sized check.
25k or 50K check, it wasn't ohyeah, here's 500 grand or a
million dollars check it wasn't.
Speaker 1 (19:45):
oh yeah, here's 500 grand or a million dollars,
success or failure on thefundraising front, because I've,
I've done this many, many timesand I always, we always, keep
track right.
You have a sheet where you haveall the investors and you get
no after no, after no, after no,after no, after no Sometimes.
I think the most was 200.
I think we pitched when I wasraising money once to raise our
series a yeah, that sheet has150 funds on it.
Speaker 2 (20:12):
you know it's funny my perspective on failing as I
shut down the startup and beenreally introspective.
Looking back, I look at areaswhere we succeeded and areas
where we failed At the time,total failure.
It's really hard wheneverything about you and your
business depends on someone elsesaying yes, and that's how I
(20:35):
saw it.
And to fly to San Francisco andto go meet with A16Z and Sousa
Ventures and General Cast andeverybody else and to walk in
and be, all you know, excitedand confident and they respond
back like this is a really goodidea or we really like you as a
founder, yeah, and to either getghosted or to get you know, a
(20:58):
quick no a quick no, or to getan email that looked like, wow,
wow, someone really wasthoughtful in writing that out.
but they said no, and then sixweeks later you see one of those
investors funding a company.
Speaker 1 (21:12):
That is in the same space.
Speaker 2 (21:13):
That's very similar to the one that we were trying
to start.
That wore on me and I thought alot that raising money.
We idolize that a lot.
I think, as founders, we doit's not a point on the journey
(21:33):
to where you want to go.
It's almost like that's thejourney, like that's the
accomplishment, and it's not.
Speaker 1 (21:39):
Yeah.
Speaker 2 (21:40):
It is not at all.
It is not at all.
But when you're going throughit for the first time and when
you feel like you need two tothree million dollars to go and
execute on this idea that youreally believe in, when
everybody tells you no, that'shard.
You start to question things.
Like you said, I'm a goodfounder, but your actions say
(22:01):
otherwise.
For sure.
Or you know, I'm laying in bedat midnight and I'm on my
computer and you're just likeI'm doing everything I can to
try and make this work and I'mdependent on other people saying
yes, because, yeah, you know,like it really matters what
(22:21):
other people think, because ifeverybody hates it, then it
doesn't go anywhere.
Speaker 1 (22:26):
What's up, phil fans?
You know, as we've listened toso many guests on this podcast,
that the road to success isoften paved with failure, with a
lot of challenges and evenfull-on face plants.
But there's a thing that youcould do to help skip some of
those bumps and bruises, andthat's really where the
consultants at Amplio come in.
See, amplio offers fractionalexecutives in finance, marketing
(22:49):
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They've been in the trenches,they've built businesses,
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But here's the kicker They'velearned from those failures and
now they're applying all thatwisdom to your business to
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So you don't have to learn thehard way.
I mean, think about it.
Instead of stumbling around inthe dark and hoping you don't
(23:16):
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(23:39):
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I love your.
I mean, entrepreneurs reallytalk a lot about this, right.
Every time we raise money, wego to TechCrunch.
We're like we raised 5 million,10 million.
And I understand from amarketing perspective, as a
(23:59):
marketer, why we do that right,because it's a signal to the
market that we're buildingsomething of value.
It's been validated by top tierVCs.
It's a signal when we're tryingto recruit great talent, right.
So there's there's a reason wedo that.
But the reality is is we needto check ourselves, because the
day that money hits the bankaccount, we often like celebrate
and we do a closing dinner andwe're like yeah, we've arrived
(24:20):
and you have not even started.
Speaker 2 (24:22):
Like you're just taking on more responsibilities.
Speaker 1 (24:24):
All you did is just took on the like this massive
amount of stewardship for otherpeople's money and guess what?
The the stakes just got really,really high.
Did you feel that when youfinally raised the money, were
you like I'm off to the races,let's go?
Or did you feel that kind ofresponsibility set in Cause?
Losing your own money is onething.
(24:44):
Losing other people's moneyfeels different.
Speaker 2 (24:46):
Yeah, and I, and I lost my own money too.
Right Like I, I I put in um towhat, to me what was meaningful
you?
know, and it, you know, an angelwould put in that same amount
of money and you know, to themit didn't really matter.
It mattered a lot to me.
You know I've been insituations where, um, you know,
(25:07):
I've I've spent time with peoplein other countries who live off
of very meager amounts of moneyevery day, and so to come back
and to think like, oh, it'ssomeone else's money and they
have enough, so if I lose it,that's fine.
No that that money really meanssomething like effort was put
into making that and now theybelieve in me enough to give it
(25:28):
to me Like that's a big deal.
I paid myself three times in 18months Wow, and I feel even a
little bit guilty for doing that.
Yeah, no, steward is theperfect word.
I feel like as a founder.
You're a steward of the moneyyou raise.
(25:49):
You're a steward over thecareers of the people you hire.
You're also a steward overmaking life better for the
customers that you serve.
You're a steward in all.
You know all all the ways thatyou can frame that, in my
opinion, so when were the firstsignals?
Speaker 1 (26:08):
you raised some money , you built the product like
what are some of the positives?
You raised some money, youbuilt the product, like what are
some of the positives?
You're like, okay, we'regetting traction, some signals
that things were working out.
And then what were the veryfirst signs?
Speaker 2 (26:27):
the red flags that made you question like, uh-oh,
we don't have enough money, orthere's a product market fit
question, or acquisition costsare too high.
Yeah, yeah, uh.
For for me, coming coming atthis from an outsider, I
remember we got connected with ahealth insurance company and we
went in and had this meetingand it was, like you know,
everybody was excited.
Everybody was telling us theidea is so great, this is so
(26:48):
cool, what you guys are doing isso innovative.
I felt like we had arrived thatday like Like, oh great,
there's a massive healthinsurance plan, they're going to
pay us a lot of money, we'regoing to do a really good job.
As we started going down thepath with this company, it was a
lot of lip service.
It was a lot of people tellingus they liked us, they thought
(27:09):
this would work, this was agreat idea, it fits really well.
But then they started sayingthings like we need to put
together a business case beforewe take it to the actual
decision makers.
And I thought to myself, well,why can't we just talk to them?
And they started saying, well,you know, they, uh, they, they
just made up a lot of excusesand so I took a step back and
(27:31):
I'm like, okay, well, we'vetried to sell to health
insurance brokers, we've triedto sell to employers directly,
we've tried to sell to healthinsurance plans.
And the reason why we weretrying all of these is because
it's really hard to sellsomething direct to consumer and
healthcare.
Sure, because if you think backto the whole, getting like 160
(27:51):
million people access healthcarethrough their employer your
employer decides what healthplan you're on.
Like that's just, that's justhow it works, at least for the
majority of people in the UnitedStates.
And so for us, we thought, inorder to make an actual
difference, we've got to go andget in with those who make the
decisions upstream, and that wasinsurance.
(28:13):
That was the employer.
Well, going to the comment ofmoney is the root cause of most
issues in healthcare.
I thought it was the risingcosts.
What I didn't fully comprehendwas how the incentives work.
So here's the status quo inhealthcare.
Mm-hmm.
(28:33):
So here's the status quo inhealthcare.
You get health insurance fromyour employer.
Your employer is not aninsurance expert, so they hire
or work with a broker orconsultant.
That broker or consultant ispaid by the insurance plan that
they represent.
And the way that insurancemakes more money is by raising
costs every year.
So if you follow that trend,it's really difficult to get a
(29:01):
lower cost health plan becausethe employer says, well, now
that drug's not covered andwe've got employees who need
that, I'm going to get yelled atbecause I just ruined this.
Speaker 1 (29:14):
For somebody Like there's this status quo or
there's this existing belief,yeah, I mean we just rolled out
benefits to a company and I hadpeople that said I can't work
here anymore because thebenefits are more expensive.
And so then as an employer, youhave to ask okay, what do you,
how do you deal with that?
Right, I mean, it is reallychallenging and some people are
happy and some people aren't,but everyone is going to be
(29:38):
spending a good chunk of theirincome, right, Making sure they
have this insurance policy.
Speaker 2 (29:42):
Yeah, and the whole idea of risk pooling.
It's like we're going to do onesize fits all.
Speaker 1 (29:46):
Yeah.
Speaker 2 (29:46):
But, but there's a point where that breaks down.
So, yeah, but, but there's apoint where that breaks down.
So the the red flag startedpopping up.
When you know we're talking tothe insurance company, it's not
moving.
We're starting to look at theother areas where we feel like
there's a good opportunity forproduct market fit, and then you
start connecting the dotsbetween you know what this party
wants and what this party wantsand how the decisions were made
(30:09):
and it was it was like, oh,wait a second by trying to lower
the cost at the employer level.
The insurance company doesn'twant that.
And you know, at the brokerlevel, there are some not great
brokers and there are some greatones, and there are some who
are transitioning from a we getpaid commission from insurance
(30:30):
to a just flat fee model.
But what's hard is they see athousand solutions all the time
and you know, okay, we'llrecommend this one if it's
proven.
Like, well, I'm a startup, likeI haven't proven this out, I
need someone to take a risk, forsure.
So we'll go to the employer andyou go to the employer and the
(30:59):
employer's like yeah, we, we buybenefits between July and
October.
And then, for sure, it startedto pop up when you know, the
health plan was just stallingout.
We were really excited about it, but we started to get
discouraged.
And we're looking at all theseother avenues and realizing that
(31:20):
there truly isn't an inflectionthat causes these parties to
want to lower the cost of healthcare in the way that we thought
there would be.
And that was hard.
That was one of those, becauseit's a channel play.
Speaker 1 (31:35):
You have to sell them through these channels.
You can't go direct to consumerand that's where the most pain
is.
Yes, employers have pain too.
Employers have to cover a goodportion of those premiums.
They have pain as well.
They totally have pain, butthey're relying on their brokers
right To really recommend thesolutions for their health plans
and their benefits.
Speaker 2 (31:54):
Yeah, and there are very few people within the
benefits function and this isnot anything against the
function and I understand whythey think this way.
I say all the time, likefirefighters, don't start fires.
Speaker 1 (32:07):
Yeah.
Speaker 2 (32:08):
A lot of people in benefits.
They deal with fires all dayand the last thing they want to
do is introduce a big ragingfire, which is our health plan
is completely changing.
We're going to pay less money,but it's not what you're used to
.
Speaker 1 (32:23):
There are some really interesting, more innovative
models.
There's some health plans herein Utah that are smaller, that
are trying to solve parts ofthat big multi-trillion dollar
problem, and I've been in theseconversations where like, should
we have a new health plan overhere doing some really
innovative things, lower cost orCigna?
(32:44):
or Aetna or Blue Cross, blueShield or know name the health
plan, and there's a risk.
And honestly, I don't thinkbrokers, I don't think HR
leaders, I don't think you knowpeople recommending benefits
have an incentive to beinnovative.
Right, they have an incentiveto maintain the status quo, even
(33:06):
if it's not because of thefinancial incentives, it's just
more of a hassle.
And so I can understand in thisspace how a new concept that
can solve a problem there'll besome resistance, and even if
they love the idea, thedecision-making process takes so
long.
So what's the learning therefor an entrepreneur?
You're in the early salesconversations for the solution
(33:28):
and you're like people aregiving you positive
reinforcement, like, oh, this isgreat, you're solving a problem
, great job, but then it's notmoving along.
Speaker 2 (33:35):
Yeah, for me.
I learned quickly that the signof someone liking it is willing
to buy it.
Period, period.
Speaker 1 (33:43):
Sign a contract.
Pay me money.
Yes, stop stop listening to allthe feedback positive from VCs
that won't write the check andlike it feels good to get all
the positive reinforcement andpeople like on LinkedIn saying,
wow, what a great problem tosolve.
I love this.
But, are they willing to like?
Open up their checkbook right,open up their wallet, put your
money where your mouth is?
Speaker 2 (34:03):
Yes, exactly, and you know there's a lot of
entrepreneurs and founders whotalk about you.
Know you sell.
Speaker 1 (34:12):
Yes.
Speaker 2 (34:13):
Sell, design, build.
Yep, I a hundred percentbelieve that and I for me, I
don't think it's like like.
I think there are situationswhere you can do it differently.
But if you want to look at aframework to start from and to
build upon, it's really magicalwhen you have a good enough
vision and people who buy inenough to say I'll pay you ahead
(34:34):
of time.
Now you know they can pay aheadof time and that money counts
towards getting the product inthe future, when it's ready, and
you give it back to them if youdon't make it.
It's just the, the act of themwilling to say solving this
problem is worth X amount ofmoney to us and we'll give it to
you now, knowing that that'sgoing to equate to you doing a
better job of solving it.
(34:55):
That's the real sell.
Speaker 1 (34:56):
That's the sell.
How you define sell matters.
A lot Money exchanges hands.
That's right.
You can't go out and say, willyou buy this?
Because that's what a lot ofentrepreneurs do and everyone
says yes, I had a of employerstell me.
Speaker 2 (35:06):
Yes, I went to a previous employer with 25,000
people who was like I want this.
Yes, I'll buy it, I'll buy it.
Speaker 1 (35:13):
And then you show up with the product and they're
like and you get the demo andthey're like, oh uh, this, this
is great.
Speaker 2 (35:20):
And again it's like the health insurance plan
conversation it's I like this, Iwant this.
I'm afraid to show it to thepeople who actually buy it.
Speaker 1 (35:28):
There's 15 people that have to opine on this and
there's misaligned incentivesSitting around a big table and
yeah, okay, so that was learningnumber one Learning, number one
.
So you're finding yourselfhaving a hard time selling
through in these conversations,so you're starting to look at
other channels, right, oh?
Speaker 2 (35:43):
I'm exploring every pivot.
Speaker 1 (35:46):
Okay, like thinking about product pivots, thinking
about different applications,like how did you work through
that?
Because I mean, this was an 18month journey, so it wasn't like
you're at this for five years,so you had to move kind of fast.
You weren't paying yourself.
You didn't have a lot of runwayright, hired a handful of
people right.
You have a founding teambuilding products, selling
marketing.
Speaker 2 (36:06):
Yeah, four people, and at a point I just said, all
right, stop, here's what we'regoing to do.
We are going to identify areaswhere we think there are
opportunities for innovationthat align with the mission that
we have and are somewhat withinthe realm of the technology we
had built.
And we spent six weeks and,like engineers, me, everybody,
(36:32):
it was all out blitz to talk toas many of them as possible, and
it was that that, to me, wasthe most invigorating part of
the journey at zipper.
It was, you know, we had man,we met with hundreds of people
and it was LinkedIn, coldconnections.
It was, hey, you know, I talkedto you.
Can you introduce me to anybodywho has?
(36:53):
you know, this job function,this job function, this job
function.
And we explored I mean, weexplored building a health plan.
We explored functional medicine.
We explored utilizationmanagement, which is, you know,
how do you make things moreefficient at the insurance level
explored prior authorizations.
We explored clinical workflows.
(37:13):
We explored you know why is itthat we do all of this research?
to come up with medical, bettermedical like practices and
procedures, yet it takes 10years for it to get adopted in
the real world like we exploredall of these things and I think
(37:34):
the the big learning from all ofthose was there were a few that
were really interesting basedon the problem we want to solve,
which was lowering the cost ofcare for a consumer, but they
were really, really complicated,like, for example, starting a
health plan.
Speaker 1 (37:51):
Sure.
Speaker 2 (37:51):
It requires a lot of money and you know it didn't
feel like our strong suit wasgoing and building a health
insurance plan and after 18months of hitting your head
against a wall and thinking youcan make a difference in an
industry that really needs it.
My biggest concern and what ledto me grappling with this
(38:12):
decision to shut it down or notwas we're out of money.
We're not paying ourselves.
Financial runway is low.
Like to be totally candid andhonest, it was to the point
where I've got two months beforeI'm paying my mortgage out of a
heloc.
It's like I'm using the equityin my house to pay down the loan
(38:33):
on my house.
Speaker 1 (38:35):
So you are out of gas , you're empty running on fumes.
Speaker 2 (38:38):
Personally, I've got three young kids, you've got a
family.
I've got a family.
I've got a fourth on the waynow which is new.
That was not, um, that did notfactor into my decision at the
time because that was not partof it, but it was like there's
(39:00):
some real tough decisions thatwe have to make.
You know, do we feel like thereis enough of an inflection,
enough of something moving inthe direction that will help
lower the cost of healthcare forconsumers?
That merits us raising money orgoing in this specific
direction and having theconfidence that it will work out
.
And going through all of thethings that we went through, I
mean, we were grinding likecrazy to try and figure it out
(39:22):
and there were a few things that, um, you had some legs, like
the utilization management.
That one had legs, but thewhole, but the whole problem we
were solving was how do we helpthe insurance company hold on to
more of the money that they get?
It wasn't how can we lower thecost of care.
It was how do we help insurancenot pay doctors?
(39:47):
How do we help them hit that20% number?
So, not mission-driven, it wasnot mission-driven it was.
Speaker 1 (39:50):
we can go make money and build a business.
Did know how do we help themhit that 20% number.
So not mission driven it wasnot mission driven it was.
Speaker 2 (39:53):
we can go make money and build a business.
Did I want to do that?
I didn't Cause.
That's not why I got into it.
Speaker 1 (39:58):
If you, had more time , if you had more money, would
you have kept kept going?
Speaker 2 (40:09):
Because it's not a not a lot of time to build
anything.
Speaker 1 (40:11):
No, it's.
It's not a not a lot of time tobuild anything no, it's, it's
not, and so like I guess myquestion is like if you had
twice, as you know, three years,if you had five years?
Speaker 2 (40:23):
yeah, I, I think I would have, because this is
where we get into failure.
When I was was in high school.
There's this movie called GloryRoad and it talks about the
Texas Western basketball teamwhich was the first team to play
five African-Americans at onetime and in the national
(40:47):
championship there were sevenpeople who played for Texas
Western and they were allAfrican American.
And the movie Glory Road ittalks about the story of how
revolutionary that was.
One of my favorite movies.
I absolutely love it, and oneof the players on the team came
and spoke to my basketball teamin high school and in the movie
there's a scene.
His name is Neville Shedd.
(41:07):
He gets hit in the face.
He's like bleeding.
He comes, he goes off the courtand he comes back with a
catcher's mask on.
He says coach, I'm ready toplay.
Well, prior to that he wasstruggling.
He wasn't giving it his all andthe coach knew that he had more
in him.
And the coach said to himNeville, you quit now, you quit
(41:29):
every day for the rest of yourlife.
I'm a sophomore in high school.
I meet him.
I admire him to the end of theearth for what he did and what
he went through.
So I write that quote on anindex card and it's in my
(41:50):
bedroom and it a quote that,like just, is ingrained in my
head.
So I get to this point withzipper and the first thing I
think to myself is I'm not aquitter, because if I quit now,
I quit every day the rest of mylife.
(42:10):
If I wouldn't have had somewhatof a forcing function to really
dig in and think about that, ofcourse I would have kept going.
I would have said we've got themoney, we'll just pivot, we'll
figure something else out, likewe'll continue to try and solve
this problem.
I am grateful that I had someof those forcing functions,
because not only did it, youknow, force us into making a
(42:33):
decision, it also made merethink what that quote means.
I still believe it, I stilllove the quote, but the way I
think about it now is differentthan how I thought about it
every single day up to thatpoint, because to me, quitting
and failure are two verydifferent things, but in that
moment they were the same thingand that weighed on me.
(42:55):
I couldn't sleep.
I was really grumpy.
At home, you know, my kidswould do one little thing that
annoyed me and I would just likeI couldn't handle it.
And so, yeah, we.
And so, yeah, we would still begoing, I think.
(43:22):
But for reasons that I nowbelieve, I'm grateful that it
went the way that it went,because of the personal learning
that came from it.
I think it's so much morepowerful in the learning.
Like part of entrepreneurshipfor me is the learning and the
growth.
And, just like you know,michael Jordan has this famous
quote like I missed 9,000 shots,I lost 300 games 26 times.
(43:43):
I was trusted to make the gamewinning shot and I missed it.
Like failure is crucial on thepath to success.
And now I look back at that andI think you know it wasn't that
I missed a shot.
It's kind of like I lost a gameand it hurts, but I've done a
better job of forgetting whathappened in terms of the outcome
(44:07):
, while remembering the journeyin terms of the learning, and
spending more time on what's tocome rather than the thing that
I can't change, that's behind me.
Speaker 1 (44:20):
When we talked, I think, I remarked that you're
just in such a healthy headspaceand it took me seven years.
Bubba Page was on this podcast.
Speaker 2 (44:31):
I've listened to that one yeah, yeah, he's like.
Speaker 1 (44:32):
It took me seven years and then I thought, oh man
, I wish that I would.
I could have had thisconversation with you 15, 10
years ago, you know, because itwould have probably changed the
way I process my own failures inbusiness and entrepreneurship.
I think it's mature, it'sinsightful.
I love this idea that quittingand failure and entrepreneurship
(44:53):
.
I think it's mature, it'sinsightful.
I love this idea that quittingand failure are different.
Speaker 2 (44:56):
How are they different?
One of the things I did, Ilooked up the definition of
failure, webster's dictionary.
One of them is lack of success.
I was like ouch, I feel that Istumbled upon instead of looking
at definitions, looking atsynonyms for failure.
One of them was negligence.
(45:20):
I was like that's reallyinteresting.
What is negligence?
Negligence is just likecarelessness.
It's like am I being careless?
No, I care so deeply about this.
(45:44):
To me, quitting when I comparethem, quitting is like I'm just,
I'm giving up, like I'm notcaring anymore.
Where, to me, failure was?
I tried and it didn't work.
So when I look at that quotenow, like you quit now, you quit
every day for the rest of yourlife.
I hope you're failing all thetime.
I hope you're trying to pushthe envelope and innovate and do
meaningful things.
I love sports.
Right, the individual who wonthe batting average in the MLB
(46:10):
this year.
I'm not a big baseball fanwhich is weird because this is
the stat that I use but, like onmy totem pole of sports,
baseball's at the bottom 3-3-2.
So 33.2% of the time that hesteps up to the plate, he is
quote-unquote successful.
Yet he is the absolute best inbaseball.
So when I think about failureand quitting, quitting is like
(46:34):
you know I'm, I'm just going tostop trying at anything.
Speaker 1 (46:37):
I'm not going to step up to the plate again.
Speaker 2 (46:38):
Yeah, I'm not going to step up to the plate again.
Speaker 1 (46:40):
Yeah, cause I'm exhausted, cause I'm yeah.
Seven out of 10 times I can'thit the ball.
Speaker 2 (46:45):
Yeah, failing is I stepped up and I swung.
Failing is I stepped up and Iswung.
Or even sometimes you don'tswing and you and you strike out
.
That's okay, it's.
It's the whole analogy of like,yeah, you fall over, but you
get back up.
And getting up doesn't meangoing to the same thing.
That's the other thing aboutfailure.
I was talking to anentrepreneur recently.
(47:06):
I absolutely love him.
Being so close to him has beenhelpful in this journey and he's
incredibly successful on theoutside.
On the inside, he's open withme about some of the struggles
he has and he said what wouldhappen if your business failed?
He's like, oh man, I can't evenimagine it would be so
(47:27):
devastating.
I was like, okay, I understandthat I felt that way a few
months ago, but now I feel free.
And it's because I think youand I talked about this, saying
there are a lot of people whochoose unhappiness over
(47:49):
uncertainty, and for me, thefear of failure was more about
what happens after the failurethan the failure itself.
It wasn't I feared shutting itdown.
Speaker 1 (48:01):
Yeah.
Speaker 2 (48:06):
But I feared more waking up the next morning, not
building zipper, having twomonths before I'm paying the
decision to shut it down was notthe thing that scared you the
most?
It was like, now, what it wasscary.
Shutting it down it was not thething that scared you the most,
(48:28):
it was like it was scary.
Shutting it down was scary, butit's a small event in a longer
journey of like okay, yeah, weshut it down, but what's going
to happen to my team?
You know what's going to happento me.
Like, what am I going to donext?
I feel lost.
Shutting this down because partof me, like I have this hole in
my heart, like Zipper was ahuge part of me.
They were like who's Jake?
(48:48):
I'm, like I'm the co-founderand CEO of Zipper.
That's who I am.
That's who I am.
August 19th I woke up and I'mnow a failed founder with no
money in the bank and this deepfeeling of I'm worthless because
everything I was I.
(49:10):
If you look at the otherdefinition, you know, a lack of
success.
I, if you look at the otherdefinition, you know a lack of
success and it was like.
You know, I wake up every dayand put on sweats and like meh,
you know it was hard, it stillis hard, but being able to
forget and say you know failureis, the experiment didn't work
(49:32):
and I'm pivoting.
Speaker 1 (49:33):
Yeah.
Speaker 2 (49:33):
Whereas quitting is, I just give up.
Speaker 1 (49:36):
I'm not going to give up.
I'm not going to try anymore.
Speaker 2 (49:38):
I'm going to pivot and you know, I'm still figuring
out what's next.
I'm in the pivot, it's stillvery fresh, but I'm in a much
better headspace.
Speaker 1 (49:49):
It's amazing.
Thank you just for being sovulnerable and open and raw
about the whole experience, andI know it's fresh.
I often think about the wordresilience and I think on
perseverance and I think this isthese are the characteristics
that we look for in greatentrepreneurs and we're like
(50:12):
they never give up, right.
We hear this and I think we weretoo narrow in how we define
that.
We're like we they never giveup on whatever investment or
whatever you know venturethey're involved in.
Right, and I've found myself,um, actually creating a larger
financial and business failurebecause I wasn't going to give
up and I and I wasn't going toquit.
(50:33):
And it was myopic, because thereality is, we can actually
minimize the magnitude of thefailure if we make the decision
earlier.
And there's always this, thisreally nagging question for an
entrepreneur.
That's why I asked you thequestion If you had more money
or time, would you still bedoing this?
You might have had $25 millionor a hundred million dollars and
(50:53):
five years, and you still bedoing this.
You might have had $25 millionor a hundred million dollars and
five years and you still wouldnot have solved the $4 trillion
problem.
And so I just challengeentrepreneurs who are listening
to this to ask themselves isthis the moment where I'm not
going to quit as an entrepreneur, but I need to close this
(51:14):
chapter?
And because this business, thisproduct, this market, this sales
motion is not working?
And if you have the courage todo that earlier in that journey,
you actually minimize that Ifyou would have been doing this
for three or four or five years,you could have been in a worse
spot and you might have solvedfor it.
But this hyper I, this hyperoptimism that more money or more
(51:36):
time will help solve for thelack of sales traction or poor
uni economics, for I'm just likebroadly speaking and and like
that is something that I thinkwe have to guard against as
entrepreneurs.
What are your thoughts on that?
Speaker 2 (51:52):
We totally idolize people who go through really
difficult things and come out ontop, and oftentimes we look at
ourselves through that same lensof it almost shouldn't be
working because that means thatif I succeed, it's all that much
better.
And going back to the way thatI framed my thinking, then
(52:12):
that's what I based my answeroff of.
I'm grateful that we wereforced to stop because it made
me change the way that I thinkabout this.
Um, I don't.
Resilience is not.
Yeah, it's not, it's not myopic, right you?
You talk about it being broader.
(52:33):
For me, it was, um, yeah, I'mgoing to mourn this, but I'm
going to be really introspectiveand I'm going to learn and grow
from it and I'm going tocontinue to try.
Like, one of the things that Idid was I put out a LinkedIn
post and I was very vulnerable,like you know what.
We failed.
We shut it down.
It hurts and it stings.
The amount of people inhealthcare who are executives or
(53:00):
founders, who reached out to mepersonally and expressed the
feelings that they have of I'vebeen doing this for years and
it's not working and it'sdriving me crazy.
That actually blew me away.
It was like, oh hey, I feel thesame thing you feel and I've
been feeling this for a whileand we're five years in and it's
(53:20):
not working.
That hurt, because I'm lookingat them like, oh man, that could
have happened to me.
It's, you know.
Back to entrepreneurship andsuccess.
Success for me has always beenthrough the eyes of others and I
(53:42):
think it's really.
I'm not, I'm not perfect atthis, I'm still trying.
I'm struggling with this, um,you know, because I'll go to
events.
I went to one recently with abunch of founders and it's like
well, what are you working on?
Well, I'm working on being abetter human being right now and
figuring out who I am.
It's such a great honest answer.
It's hard because, people lookat that and they think, well,
(54:04):
you're not interesting, oryou're not going to get me to
this, or you're not.
You know we tend to judge yeah.
Speaker 1 (54:10):
This has been insightful and I was so grateful
and I am so excited to seewhat's next.
In fact, when you first satdown, I said, do you know?
And you're like, not yet, I'mdoing some consulting, I'm
figuring it out, but like Ithink that the key is is that
you're you're probably going tobe batting 300 and and so you're
going to step up to the plateagain.
(54:30):
You're going to take anotherswing and you might take one or
two more, but you're going totake another swing and you might
take one or two more, butyou're going to get that bat on
that ball and it's going to befun to watch that.
And the LinkedIn posts will bedifferent.
And the learning from successis valuable, but the deep
learning, not just aboutbusiness and entrepreneurship,
but about who you are and whatyou're made of and what matters
(54:53):
to you and how you want tooperate.
That learning, um, it comesfrom challenge, comes from the
grind, it comes from, maybe, aneventual business failure, and
that doesn't define you as anentrepreneur at all.
In fact, that the responseyou're getting from this
LinkedIn post, which I want youto actually share.
Uh, as we conclude, I want youto read it, if you're willing?
Speaker 2 (55:16):
Yeah, do you have it?
Yeah, I got it right here.
Yeah, you're on my phone, solet me.
Speaker 1 (55:20):
I haven't read this.
Speaker 2 (55:21):
I took a long time to write this, by the way.
Speaker 1 (55:23):
Honestly, when I read it, I reached out and said, hey
, we need to talk, because Iloved that.
So close.
In proximity to the moment youshut that down, you were on
LinkedIn saying this is whathappened.
This is how I feel about it.
But that response from thecommunity should also tell you
something that you're.
You can't define yourself bythe outcome of zipper alone, and
(55:45):
neither you know the thecommunity is not defining you by
this outcome.
They're defining you and andthey're really defining you by
your response to the outcome.
And so I think this is what's soprofound about your LinkedIn
post, so go ahead and read it.
Speaker 2 (56:01):
Okay, I'll read it, and quickly.
Before I read this, I had aninvestor tell me you know, the
best entrepreneurs run aroundwalls, run through walls, under
walls, over walls, but they alsoknow which walls to stop.
And I think my post is somewhatalong those lines, so I'll read
(56:22):
this.
I haven't read this in a while.
This was probably the beginningof September.
We made the difficult decisiona couple weeks ago to shut down
Zipper.
Yeah, so many good things in mylife have come from not giving
up and digging deeper wheneverything and everyone else
said that it was okay to give up.
(56:43):
Part of what made this decisionso difficult was the wrestle
with whether or not shuttingdown the company was giving up
TLDR.
Our decision to shut downZipper is not giving up.
Starting a company and being afounder is hard.
The highs are higher and thelows are lower.
We had a few highs and our fairshare of lows over the past 16
(57:03):
months.
Everyone asks how it is going,and at times that question is
really hard to answer out loud.
Most people think companybuilding is hard, but they
quickly replace those thoughtsby idolizing those who are
successful in terms of bigfundraising, announcements and
exits.
There are fewer people who,while respecting and admiring
those who beat the odds, see itfor what it actually is the
(57:27):
blood, sweat and tears of givingit your all every day to solve
a problem that you deeply careabout.
Most of the time.
That process isn't glamorous,and that is why I love company
building.
The best things in life are onthe other side of hard.
It didn't turn out as we hadhoped, but we will keep grinding
in other ways to solve theproblems in this world that need
to be solved.
We are not done putting in theblood, sweat and tears to make a
(57:49):
difference.
We will just be making thatdifference in other ways.
I'm so grateful for those whogave their money, time, advice
and more to zipper over the past16 months, and I said so.
What is the next thing?
Not sure yet, but I'm workingon figuring that out as we speak
.
My goal is, and always will bemaking a dent in the world
onward and upward.
Speaker 1 (58:08):
Okay, love it.
Thank you, jake, the caught.
The responses to your messagewere so powerful and I love this
one.
10 out of 10 would no will withan exclamation point.
All caps back you again.
Like that to me is so powerfulright.
Tim, he's got your back man.
Speaker 2 (58:28):
We'll throw a shout out here to Tim.
Tim was the one who told methat comment that I gave right
before I read the post which isthe best entrepreneurs know.
You know they run through walls.
They run around walls, but theyknow which ones to stop at.
Speaker 1 (58:41):
Is he the one that said it?
That was Tim.
This is so insightful.
I want you to look at thecamera and say whatever you want
as your parting thought.
Just a declarative statement.
Speaker 2 (58:50):
My name is Jake Benson.
I'm a failed startup founderwith my first company, zipper,
and failure and quitting are twovery different things.
Speaker 1 (59:00):
I love it.
That's perfect, jake, you'reawesome.
Speaker 2 (59:03):
Joe, thank you.
Speaker 1 (59:04):
Thanks for tuning in to the Real F Word.
The Real F Word is failure, andremember that failure is a
stepping stone, it's not just astumbling block.
Join us next time as wecontinue to explore the journey
of resilience and growth,without ignoring the true costs
personally, professionally andfinancially that comes with
failure.
Keep learning, keep growing andkeep embracing the real stories
of entrepreneurship.
(59:24):
See you next time.
Welcome to the Real F Word.
I remember when I firstlaunched the podcast, it was
interesting because everyonewould reach out and say, hey,
you really need to talk to thisperson, or you really need to
talk to that person, and acouple of people, I think on
LinkedIn, said, hey, you shouldreally talk to Jake.
Jake has this experience andit's fresh right, it's only been
(00:23):
.
Speaker 2 (00:23):
It's very fresh August 19th, okay, probably two
and a half, almost three months.
Speaker 1 (00:29):
Three months and so like.
This is an experience thatyou're just coming out of
starting a company, raising alittle bit of capital, building
something that was meaningfuland making a difference in the
world, and having and you had toshut it down, and so today
we're going to unpack that alittle bit.
But let's let's go back evenearlier.
You spent a ton of time inFinTech, right?
You were like, worked forFinicity and MasterCard.
(00:51):
You were chief of staff, youhad a leadership role there.
Tell me about what led you toyour first entrepreneurial
endeavor.
Speaker 2 (01:00):
Yeah, you know I.
So I grew up in a house wheremy dad was an entrepreneur, my
grandparents were entrepreneurs.
It was something that I wasprivy to pretty early, both the
good that can come from it, butalso the struggles that exist.
Both my grandfathers had prettyrough stories when it came to
entrepreneurship failed ventures, things that went wrong, some
(01:23):
things that worked, and so itwas something that I just grew
up familiar with, and when I wasa sophomore in college, I ended
up going to lunch with thefounder of Finicity for the
purpose of trying to get hisadvice on whether or not I
should study finance oraccounting, and two months later
(01:45):
was my first day on the job atFinicity.
So my foray into a startup andinto this world for myself was
very much serendipitous, and theFinicity journey was really
exciting.
Like you mentioned, I heldvarious roles within the company
.
We got acquired by MasterCard,but towards the end I was chief
(02:06):
of staff, and that's really whenI started to think.
You know, it's great to see acompany start, grow, succeed,
but I want to be in that seat, Iwant to be in that chair.
I want to go through thatexperience, not for the sake of
(02:29):
just being a founder, butbecause I want to solve problems
at that level and there weresome problems that were really
near and dear to me and thosewere the ones that I actually
ended up going and trying tosolve and what else was it?
Speaker 1 (02:42):
It was the problem solving, being in the sea,
making the decisions, leadingthe vision and the strategy.
What else was it that?
What was the allure of doing iton your own versus cause cause?
Finicity was pretty large.
Mastercard is massive.
Speaker 2 (02:54):
Yeah, mastercard is huge.
Speaker 1 (02:56):
You're working for a massive organization and now
you're like, hey, I'm going tostart something from the ground
up.
Speaker 2 (03:01):
I love building.
I love creating.
One of the most fulfillingthings for me at Phenicity was
the ability to talk withsomebody, to hear them express
their problems and to thinkcreatively about.
There's nothing that perfectlysolves that.
How can we solve that?
I think one of the mostfulfilling things for me is
being in a situation wheresomething that I do or bring
(03:28):
changes someone in a positiveway, and entrepreneurship is all
about that.
It's all about how do I go andfind problems that no one solved
in a good way and solve them.
That was the allure to me.
It's not driven by the endresult, it's driven by I get to
wake up in the morning and I getto do something that hasn't
(03:50):
been done.
And there are a lot ofentrepreneurial ideas to me that
aren't exciting at all and it'sbecause they don't encapsulate
that like true, meaningfulmaking a difference.
I think about the quote wheremuch is given, much is required.
All the time I look at thecards I've been dealt Born in
(04:11):
Utah, lived in Canada for awhile, grown up, moved back and
then I've spent time in otherplaces around the world where
you see poverty and people whohave a lot less poverty and
people who have a lot less, andgoing through those makes you
realize you know I've got both aresponsibility but an amazing
(04:32):
opportunity to do somethingreally, really meaningful, and
to me that manifests the best.
In my opinion it doesn't haveto be everybody's opinion.
This is a truth to Jake, asI've explored who I am and what
I like, entrepreneurship is theway that that resonates for me.
Speaker 1 (04:53):
So not to jump to the punchline here, but does your
experience with Zipper, whichwe're going to talk about, does
it change your perspective onentrepreneurship?
Does it weaken your resolve?
Has it made you questionwhether or not, like you want to
do this again?
Speaker 2 (05:09):
Immediately thereafter?
Yes, two and a half threemonths later, absolutely not.
Speaker 1 (05:15):
It took.
It only took you three monthsand you're like I'm going to get
back on the saddle.
Speaker 2 (05:18):
That's amazing In my head actually doing it?
No, there's.
There's um, I'm going to do itdifferently.
I think is is.
Is the the punchline to that?
Uh, definitely, I love.
I love the journey, I love theexperience.
(05:39):
Selling did not make mequestion whether or not.
It made me question whether ornot being an entrepreneur is
what I want to do, but it wasmore.
It came more from like who am ILike, what am I doing?
It didn't come from it didn'tcome from a different place.
(06:00):
It was more introspectivequestioning Is this what I want
to do?
Who am I, what am I good at?
It was reflection, notdiscouragement.
Speaker 1 (06:07):
Yeah.
Speaker 2 (06:08):
It was all introspection, okay, and I'm not
over it yet.
It's not like I've moved on,right.
I still wake up every daywishing that I would have
figured it out.
I don't.
I don't think that feeling isgoing to go away immediately.
Speaker 1 (06:20):
Yeah, so tell me about zipperipper.
Okay, so did you start this?
This idea had been percolatingfor a while, and what's?
What's the problem that youwere solving and how did you get
this thing off the ground?
Speaker 2 (06:33):
Yeah, I think it's helpful to start a little bit
from the FinTech journey.
I started at Finicity having noidea what the world of FinTech
was.
I'm a sophomore in college.
I sit down on the first day andit's here's a list of a whole
bunch of companies you've neverheard of.
You got to call them, you gotto start trying to close them as
(06:54):
deals.
You got to bring them on ascustomers and I remember sitting
there thinking like this mightbe a, this might've been a bad
idea, because I'm a total fishout of water and as I started
getting into it, I fell in lovewith this concept of.
And for those who don't knowwhat Finicity is, there's a
competitor that we had that alot of people know called Plaid.
(07:17):
We did the same thing.
We were the infrastructure thatallowed people to connect their
bank accounts to apps.
So if you used Venmo orRobinhood, you've interacted
with the technology that we werebuilding, and there was
something amazing about howunlocking access to people's
bank accounts where they couldshare the information that lived
there in other places.
(07:38):
You know you could get lowerinterest rate loans, you could
send money to friends, you couldget and bypass a lot of the
fees that existed in financialservices.
That, to me, was reallymeaningful because I saw.
You know it doesn't make sense.
It's hard enough for money tobe made in certain situations.
(07:59):
That why does the place thatyou put it take from it right?
That was something that Ireally fell in love with.
I really enjoyed being a partof.
Well, I started you know, myfamily.
We had kids and you know, goingfrom being a couple where you
don't go and visit the doctor alot to having kids and
(08:22):
complications with having a babyI started to experience a part
of financial services that wasvery foreign to me, which was
the cost of healthcare andseeing how insurance worked and
how so affordable.
Right, the bills worked, yeah.
Speaker 1 (08:36):
Premiums of $1,700 a month.
Speaker 2 (08:39):
I've got a friend who said the greatest trick the
devil ever pulled was convincingpeople that out-of-pocket costs
don't include the insurancepremiums.
In 2023, the average cost for afamily of four just to have
insurance which is the premiumsyou pay monthly $24,000.
A lot of that is oblivious tous because our employers pay it.
(09:06):
It comes out of our paychecksdirectly, and so $24,000 a year
goes to paying for healthcarefor a family of four.
That does not include the moneythat you pay out of your own
pocket before you've even metyour $6,000 or $7,000 deductible
or your $15, know so brokenfifteen thousand dollars in out
of pocket costs and we all feelit, but no one can solve for it
(09:28):
and the costs just go up.
Speaker 1 (09:30):
I've never seen the car, I've never gone to a
renewal right oh, it never goesdown oh hey, guess what I'm
going to save you?
20 this year.
Speaker 2 (09:36):
It always goes up, that is hard like there's,
there's no relief in sight forincreasing premiums, at least in
the existing model.
Well, to talk about Zipper,that was the problem I wanted to
solve.
Speaker 1 (09:50):
Huge problem, billions, trillion dollar
problem.
I don't know how big thehealthcare industry is $4.5
trillion $4.5 trillion.
Speaker 2 (09:59):
And about half of that is funded by the 160
million people who get healthinsurance through their
employers.
It's like that's a big,meaningful problem.
I have directly felt the painof that.
I remember going to a doctor'svisit and it was a visiting
physician and that visitingphysician was not covered by my
(10:20):
insurance.
Yet the location that I went towas my insurance.
Yet the location that I went towas.
And for those who don'tunderstand the dynamic in
healthcare when a bill gets puttogether for you, you're billed
by both the facility and the doc.
The practitioner, yeah, andsometimes One is in network and
one is out.
And one isn't.
(10:40):
Yeah, and in insurance, thecost for something in network
versus something out of networkis totally different.
We got a $1,300 bill and I'mthinking to myself I pay a ton
of money every month for asolution or a product that's
supposed to pay for myhealthcare right, but it didn't.
(11:03):
So so experiences like thatover time led me to digging in
and trying to understand.
I understand, I get the FinTechworld, I understand how it
works.
Healthcare is one of thebiggest problems, and my thesis
was money is the root cause ofmost issues in healthcare, and
and I validated that, but not inthe way that I thought I would
(11:26):
Um, so that was the impetusbehind zipper.
It was personal experiences.
Plus, as I went out and talkedto people, it was ironic how the
financial pain oftentimesmimicked the emotional and
physical pain in healthcare.
That was.
That was absurd to me.
Yeah, still is.
Speaker 1 (11:46):
So what problem was zipper solving?
Speaker 2 (11:48):
We were trying to lower the cost of healthcare for
individuals.
Speaker 1 (11:51):
And how were you doing that?
Speaker 2 (11:52):
There are companies who advertise insurance as being
simple.
It is nothing.
No, it's never simple.
No, it thrives off ofcomplexity.
Do you think that's purposeful?
Do you think it?
Speaker 1 (12:05):
could be simple, or do you think it's just?
No, it thrives off ofcomplexity.
Do you think that's purposeful?
Do you think it could be simple, or do you think it's just
inherently complicated becauseof the way that our healthcare
system works?
Speaker 2 (12:14):
I don't think anybody .
I don't think most people whowork in the world of insurance
or healthcare.
I think the majority of peopleare amazing.
They do things for the rightreasons, I think, over time.
Insurance came about in 1943 asa solution to wage control.
I think the 81 years of boltingon additional solutions and
(12:38):
morphing it, I think that's theproblem.
Speaker 1 (12:40):
It's just like amalgamation of HMOs and PPOs
and HDHPs and HSAs, and FSAs.
Speaker 2 (12:52):
It's a system with a lot of baggage that's tried to
solve immediate, short-termproblems and, as the target has
moved, the baggage of solvingthe previous problem was brought
along to solving the next.
And so we live in a world wherethere's this giant archaic,
difficult-to-change system thatthrives off of incentives that
(13:13):
negatively impact consumers.
And so when I went in, it wassimply put I just want to lower
the cost of healthcare for Joe,for Jake, for people who work
really hard but end up paying$24,000 just to say that they
have insurance when they go tothe doctor's office and they're
paying a copay instead of payingthe price out of pocket.
(13:33):
Like that's it.
I want to lower the costbecause I think that there's a
lot of money that is wasted anduh, and that that was it, like
that was the basis.
I just want to solve thatproblem and the insight was
coming from the world offinicity, like if people can
share information directly fromtheir bank account with an app.
There's a lot of interesting,unique business models and
(13:56):
insights that that delivers,that lowers the cost of
financial services when you goto the doctor this is crazy to
me and you get a service.
Speaker 1 (14:05):
You have no idea how much that costs and if you ask,
which I've done so many times infact, in my background in fact,
my dad worked at a large brokerat the tail end of his career
for 15 years.
And so I kind of grew uptalking about consumer directed
healthcare and so my familiaritywith benefits comes from my, my
(14:25):
, really my even my childhood.
And the reality is, is when youask a doctor right, and I've
done it so many times, how muchis this going to cost?
They don't know.
They don't know the answer andonce in a while there'll be a
range or they'll give you to theoffice manager.
But it is shocking.
It's like going into a cardealership and saying, hey, I, I
(14:46):
, I like that car, I need thatcar.
And they're like perfect, hereyou go, here's your car, and
we'll send you the invoice in 30days and you're like is it 20 K
?
Is it 30 K?
Is it 50 K?
It's, it's, it's insane.
Speaker 2 (15:01):
It's again it's.
It's a.
It's a byproduct of the system.
Yeah, it's again.
It's a byproduct of the system.
Yeah, it's not that that doctordoesn't want to tell you no he
doesn't even know.
But if I'm a doctor and I sayit's going to cost you $200 and
the bill comes back later andit's $300, like how do you view
me now as your doctor?
Yeah, not great.
(15:21):
It also depends on whatinsurance you have, sure, what
plan you have, how much of yourdeductible you've already paid
out.
There's just so many factorsthat play into this that make it
complicated.
It's just really difficult.
Speaker 1 (15:34):
It's a multi-trillion dollar problem.
Was the problem too big for youto solve?
Speaker 2 (15:38):
Depends on what like how you frame the problem.
It depends on that.
How you frame the problem.
It depends on that.
Vcs love big TAMs but, as afounder, part of the journey, at
least from my perspective, waswe need to raise money and
(16:01):
saying healthcare is a $4.5trillion problem.
Speaker 1 (16:03):
it's almost too big.
I want to talk about TAM for asecond, though, because I think
that's a really great insightthere's for many, many years.
Right, it was always likeeveryone would just show up and
it was just like a huge TAM,like I don't really care about
the total addressable market.
I do care about the serviceableaddressable market, and what
(16:26):
percentage of that can I obtain?
And so you probably foundyourself getting really deep
into really understanding what'sthe pocket, what's the corner
of the market that you canservice with your solution or
with your product, and how muchof that can you actually obtain.
Right, and I think that's whenan entrepreneur is pitching and
I'm on the investor side andthey really understand that
deeply.
(16:46):
That to me is a strong signalthat they've done that work to
pare back the problem tosomething that they can actually
address as a startup withlimited resources, and then that
can be a land and expandapproach where they solve this
problem, then you can solveother problems and you can kind
of move to a larger obtainablemarket.
Speaker 2 (17:05):
Yeah, in the throes of trying to fundraise, I did
not think enough from a firstprinciples approach, zipper for
me was I had a previousco-founding experience in an
incubated startup but truly as aas a first time founder, zipper
was Zipper, was it?
I cared a lot about what otherpeople thought and I was
(17:30):
confident in my abilities.
But I was confident in theabilities of people who had
succeeded before and we had somereally amazing advisors who had
raised from top-name VCs in NewYork and Silicon Valley.
And the advice I got pertainingto TAM was like you want a big
(17:52):
TAM because VCs really like abig TAM.
Well, the truth is the VC caresabout your revenue because your
valuation and your success is onwhether or not you get to a100
million a year in revenue ormore.
That's kind of the VC measure.
Tam is just a way to say themarket's big enough where we can
get $100 million in revenue.
Well, there's a lot ofbusinesses who make a lot more
(18:15):
than $100 million in revenue who, when they're pitching
initially, their TAM is in $4.5trillion $4.5 trillion and so
it's a proxy for is there enoughroom here for us to make enough
money to have outsized?
Speaker 1 (18:32):
returns for you as a VC.
That's why the obtainablemarket that answers the question
whether or not it can be $100million in revenue in the next
five years, right.
Speaker 2 (18:40):
In 10 years, are there enough customers who want?
Well, in seven years if youthink of the math, seven or
eight years are there enoughcustomers who will want what
you've got, to the tune of $100million?
Speaker 1 (18:52):
and paying for it.
Speaker 2 (18:54):
That's what they really want, right?
Speaker 1 (18:55):
And you went out and pitched this.
How many times?
92.
Okay, I love it.
92.
How many times did you hear no?
Speaker 2 (19:05):
85.
And it's helpful to get context92,.
If you include the seven angelswho said yes and the 85 VCs who
said no, there were more.
Right, you know more angels andothers that we spoke with.
Speaker 1 (19:24):
Because the angels are the ones that ended up
funding the deal.
No institutional VC.
It was a little too early.
Speaker 2 (19:30):
We did have an institutional VC, but it was.
We believe in you and we'llgive you an angel-sized check.
25k or 50K check, it wasn't ohyeah, here's 500 grand or a
million dollars check it wasn't.
Speaker 1 (19:45):
oh yeah, here's 500 grand or a million dollars,
success or failure on thefundraising front, because I've,
I've done this many, many timesand I always, we always, keep
track right.
You have a sheet where you haveall the investors and you get
no after no, after no, after no,after no, after no Sometimes.
I think the most was 200.
I think we pitched when I wasraising money once to raise our
series a yeah, that sheet has150 funds on it.
Speaker 2 (20:12):
you know it's funny my perspective on failing as I
shut down the startup and beenreally introspective.
Looking back, I look at areaswhere we succeeded and areas
where we failed At the time,total failure.
It's really hard wheneverything about you and your
business depends on someone elsesaying yes, and that's how I
(20:35):
saw it.
And to fly to San Francisco andto go meet with A16Z and Sousa
Ventures and General Cast andeverybody else and to walk in
and be, all you know, excitedand confident and they respond
back like this is a really goodidea or we really like you as a
founder, yeah, and to either getghosted or to get you know, a
(20:58):
quick no a quick no, or to getan email that looked like, wow,
wow, someone really wasthoughtful in writing that out.
but they said no, and then sixweeks later you see one of those
investors funding a company.
Speaker 1 (21:12):
That is in the same space.
Speaker 2 (21:13):
That's very similar to the one that we were trying
to start.
That wore on me and I thought alot that raising money.
We idolize that a lot.
I think, as founders, we doit's not a point on the journey
(21:33):
to where you want to go.
It's almost like that's thejourney, like that's the
accomplishment, and it's not.
Speaker 1 (21:39):
Yeah.
Speaker 2 (21:40):
It is not at all.
It is not at all.
But when you're going throughit for the first time and when
you feel like you need two tothree million dollars to go and
execute on this idea that youreally believe in, when
everybody tells you no, that'shard.
You start to question things.
Like you said, I'm a goodfounder, but your actions say
(22:01):
otherwise.
For sure.
Or you know, I'm laying in bedat midnight and I'm on my
computer and you're just likeI'm doing everything I can to
try and make this work and I'mdependent on other people saying
yes, because, yeah, you know,like it really matters what
(22:21):
other people think, because ifeverybody hates it, then it
doesn't go anywhere.
Speaker 1 (22:26):
What's up, phil fans?
You know, as we've listened toso many guests on this podcast,
that the road to success isoften paved with failure, with a
lot of challenges and evenfull-on face plants.
But there's a thing that youcould do to help skip some of
those bumps and bruises, andthat's really where the
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I love your.
I mean, entrepreneurs reallytalk a lot about this, right.
Every time we raise money, wego to TechCrunch.
We're like we raised 5 million,10 million.
And I understand from amarketing perspective, as a
(23:59):
marketer, why we do that right,because it's a signal to the
market that we're buildingsomething of value.
It's been validated by top tierVCs.
It's a signal when we're tryingto recruit great talent, right.
So there's there's a reason wedo that.
But the reality is is we needto check ourselves, because the
day that money hits the bankaccount, we often like celebrate
and we do a closing dinner andwe're like yeah, we've arrived
(24:20):
and you have not even started.
Speaker 2 (24:22):
Like you're just taking on more responsibilities.
Speaker 1 (24:24):
All you did is just took on the like this massive
amount of stewardship for otherpeople's money and guess what?
The the stakes just got really,really high.
Did you feel that when youfinally raised the money, were
you like I'm off to the races,let's go?
Or did you feel that kind ofresponsibility set in Cause?
Losing your own money is onething.
(24:44):
Losing other people's moneyfeels different.
Speaker 2 (24:46):
Yeah, and I, and I lost my own money too.
Right Like I, I I put in um towhat, to me what was meaningful
you?
know, and it, you know, an angelwould put in that same amount
of money and you know, to themit didn't really matter.
It mattered a lot to me.
You know I've been insituations where, um, you know,
(25:07):
I've I've spent time with peoplein other countries who live off
of very meager amounts of moneyevery day, and so to come back
and to think like, oh, it'ssomeone else's money and they
have enough, so if I lose it,that's fine.
No that that money really meanssomething like effort was put
into making that and now theybelieve in me enough to give it
(25:28):
to me Like that's a big deal.
I paid myself three times in 18months Wow, and I feel even a
little bit guilty for doing that.
Yeah, no, steward is theperfect word.
I feel like as a founder.
You're a steward of the moneyyou raise.
(25:49):
You're a steward over thecareers of the people you hire.
You're also a steward overmaking life better for the
customers that you serve.
You're a steward in all.
You know all all the ways thatyou can frame that, in my
opinion, so when were the firstsignals?
Speaker 1 (26:08):
you raised some money , you built the product like
what are some of the positives?
You raised some money, youbuilt the product, like what are
some of the positives?
You're like, okay, we'regetting traction, some signals
that things were working out.
And then what were the veryfirst signs?
Speaker 2 (26:27):
the red flags that made you question like, uh-oh,
we don't have enough money, orthere's a product market fit
question, or acquisition costsare too high.
Yeah, yeah, uh.
For for me, coming coming atthis from an outsider, I
remember we got connected with ahealth insurance company and we
went in and had this meetingand it was, like you know,
everybody was excited.
Everybody was telling us theidea is so great, this is so
(26:48):
cool, what you guys are doing isso innovative.
I felt like we had arrived thatday like Like, oh great,
there's a massive healthinsurance plan, they're going to
pay us a lot of money, we'regoing to do a really good job.
As we started going down thepath with this company, it was a
lot of lip service.
It was a lot of people tellingus they liked us, they thought
(27:09):
this would work, this was agreat idea, it fits really well.
But then they started sayingthings like we need to put
together a business case beforewe take it to the actual
decision makers.
And I thought to myself, well,why can't we just talk to them?
And they started saying, well,you know, they, uh, they, they
just made up a lot of excusesand so I took a step back and
(27:31):
I'm like, okay, well, we'vetried to sell to health
insurance brokers, we've triedto sell to employers directly,
we've tried to sell to healthinsurance plans.
And the reason why we weretrying all of these is because
it's really hard to sellsomething direct to consumer and
healthcare.
Sure, because if you think backto the whole, getting like 160
(27:51):
million people access healthcarethrough their employer your
employer decides what healthplan you're on.
Like that's just, that's justhow it works, at least for the
majority of people in the UnitedStates.
And so for us, we thought, inorder to make an actual
difference, we've got to go andget in with those who make the
decisions upstream, and that wasinsurance.
(28:13):
That was the employer.
Well, going to the comment ofmoney is the root cause of most
issues in healthcare.
I thought it was the risingcosts.
What I didn't fully comprehendwas how the incentives work.
So here's the status quo inhealthcare.
Mm-hmm.
(28:33):
So here's the status quo inhealthcare.
You get health insurance fromyour employer.
Your employer is not aninsurance expert, so they hire
or work with a broker orconsultant.
That broker or consultant ispaid by the insurance plan that
they represent.
And the way that insurancemakes more money is by raising
costs every year.
So if you follow that trend,it's really difficult to get a
(29:01):
lower cost health plan becausethe employer says, well, now
that drug's not covered andwe've got employees who need
that, I'm going to get yelled atbecause I just ruined this.
Speaker 1 (29:14):
For somebody Like there's this status quo or
there's this existing belief,yeah, I mean we just rolled out
benefits to a company and I hadpeople that said I can't work
here anymore because thebenefits are more expensive.
And so then as an employer, youhave to ask okay, what do you,
how do you deal with that?
Right, I mean, it is reallychallenging and some people are
happy and some people aren't,but everyone is going to be
(29:38):
spending a good chunk of theirincome, right, Making sure they
have this insurance policy.
Speaker 2 (29:42):
Yeah, and the whole idea of risk pooling.
It's like we're going to do onesize fits all.
Speaker 1 (29:46):
Yeah.
Speaker 2 (29:46):
But, but there's a point where that breaks down.
So, yeah, but, but there's apoint where that breaks down.
So the the red flag startedpopping up.
When you know we're talking tothe insurance company, it's not
moving.
We're starting to look at theother areas where we feel like
there's a good opportunity forproduct market fit, and then you
start connecting the dotsbetween you know what this party
wants and what this party wantsand how the decisions were made
(30:09):
and it was it was like, oh,wait a second by trying to lower
the cost at the employer level.
The insurance company doesn'twant that.
And you know, at the brokerlevel, there are some not great
brokers and there are some greatones, and there are some who
are transitioning from a we getpaid commission from insurance
(30:30):
to a just flat fee model.
But what's hard is they see athousand solutions all the time
and you know, okay, we'llrecommend this one if it's
proven.
Like, well, I'm a startup, likeI haven't proven this out, I
need someone to take a risk, forsure.
So we'll go to the employer andyou go to the employer and the
(30:59):
employer's like yeah, we, we buybenefits between July and
October.
And then, for sure, it startedto pop up when you know, the
health plan was just stallingout.
We were really excited about it, but we started to get
discouraged.
And we're looking at all theseother avenues and realizing that
(31:20):
there truly isn't an inflectionthat causes these parties to
want to lower the cost of healthcare in the way that we thought
there would be.
And that was hard.
That was one of those, becauseit's a channel play.
Speaker 1 (31:35):
You have to sell them through these channels.
You can't go direct to consumerand that's where the most pain
is.
Yes, employers have pain too.
Employers have to cover a goodportion of those premiums.
They have pain as well.
They totally have pain, butthey're relying on their brokers
right To really recommend thesolutions for their health plans
and their benefits.
Speaker 2 (31:54):
Yeah, and there are very few people within the
benefits function and this isnot anything against the
function and I understand whythey think this way.
I say all the time, likefirefighters, don't start fires.
Speaker 1 (32:07):
Yeah.
Speaker 2 (32:08):
A lot of people in benefits.
They deal with fires all dayand the last thing they want to
do is introduce a big ragingfire, which is our health plan
is completely changing.
We're going to pay less money,but it's not what you're used to
.
Speaker 1 (32:23):
There are some really interesting, more innovative
models.
There's some health plans herein Utah that are smaller, that
are trying to solve parts ofthat big multi-trillion dollar
problem, and I've been in theseconversations where like, should
we have a new health plan overhere doing some really
innovative things, lower cost orCigna?
(32:44):
or Aetna or Blue Cross, blueShield or know name the health
plan, and there's a risk.
And honestly, I don't thinkbrokers, I don't think HR
leaders, I don't think you knowpeople recommending benefits
have an incentive to beinnovative.
Right, they have an incentiveto maintain the status quo, even
(33:06):
if it's not because of thefinancial incentives, it's just
more of a hassle.
And so I can understand in thisspace how a new concept that
can solve a problem there'll besome resistance, and even if
they love the idea, thedecision-making process takes so
long.
So what's the learning therefor an entrepreneur?
You're in the early salesconversations for the solution
(33:28):
and you're like people aregiving you positive
reinforcement, like, oh, this isgreat, you're solving a problem
, great job, but then it's notmoving along.
Speaker 2 (33:35):
Yeah, for me.
I learned quickly that the signof someone liking it is willing
to buy it.
Period, period.
Speaker 1 (33:43):
Sign a contract.
Pay me money.
Yes, stop stop listening to allthe feedback positive from VCs
that won't write the check andlike it feels good to get all
the positive reinforcement andpeople like on LinkedIn saying,
wow, what a great problem tosolve.
I love this.
But, are they willing to like?
Open up their checkbook right,open up their wallet, put your
money where your mouth is?
Speaker 2 (34:03):
Yes, exactly, and you know there's a lot of
entrepreneurs and founders whotalk about you.
Know you sell.
Speaker 1 (34:12):
Yes.
Speaker 2 (34:13):
Sell, design, build.
Yep, I a hundred percentbelieve that and I for me, I
don't think it's like like.
I think there are situationswhere you can do it differently.
But if you want to look at aframework to start from and to
build upon, it's really magicalwhen you have a good enough
vision and people who buy inenough to say I'll pay you ahead
(34:34):
of time.
Now you know they can pay aheadof time and that money counts
towards getting the product inthe future, when it's ready, and
you give it back to them if youdon't make it.
It's just the, the act of themwilling to say solving this
problem is worth X amount ofmoney to us and we'll give it to
you now, knowing that that'sgoing to equate to you doing a
better job of solving it.
(34:55):
That's the real sell.
Speaker 1 (34:56):
That's the sell.
How you define sell matters.
A lot Money exchanges hands.
That's right.
You can't go out and say, willyou buy this?
Because that's what a lot ofentrepreneurs do and everyone
says yes, I had a of employerstell me.
Speaker 2 (35:06):
Yes, I went to a previous employer with 25,000
people who was like I want this.
Yes, I'll buy it, I'll buy it.
Speaker 1 (35:13):
And then you show up with the product and they're
like and you get the demo andthey're like, oh uh, this, this
is great.
Speaker 2 (35:20):
And again it's like the health insurance plan
conversation it's I like this, Iwant this.
I'm afraid to show it to thepeople who actually buy it.
Speaker 1 (35:28):
There's 15 people that have to opine on this and
there's misaligned incentivesSitting around a big table and
yeah, okay, so that was learningnumber one Learning, number one
.
So you're finding yourselfhaving a hard time selling
through in these conversations,so you're starting to look at
other channels, right, oh?
Speaker 2 (35:43):
I'm exploring every pivot.
Speaker 1 (35:46):
Okay, like thinking about product pivots, thinking
about different applications,like how did you work through
that?
Because I mean, this was an 18month journey, so it wasn't like
you're at this for five years,so you had to move kind of fast.
You weren't paying yourself.
You didn't have a lot of runwayright, hired a handful of
people right.
You have a founding teambuilding products, selling
marketing.
Speaker 2 (36:06):
Yeah, four people, and at a point I just said, all
right, stop, here's what we'regoing to do.
We are going to identify areaswhere we think there are
opportunities for innovationthat align with the mission that
we have and are somewhat withinthe realm of the technology we
had built.
And we spent six weeks and,like engineers, me, everybody,
(36:32):
it was all out blitz to talk toas many of them as possible, and
it was that that, to me, wasthe most invigorating part of
the journey at zipper.
It was, you know, we had man,we met with hundreds of people
and it was LinkedIn, coldconnections.
It was, hey, you know, I talkedto you.
Can you introduce me to anybodywho has?
(36:53):
you know, this job function,this job function, this job
function.
And we explored I mean, weexplored building a health plan.
We explored functional medicine.
We explored utilizationmanagement, which is, you know,
how do you make things moreefficient at the insurance level
explored prior authorizations.
We explored clinical workflows.
(37:13):
We explored you know why is itthat we do all of this research?
to come up with medical, bettermedical like practices and
procedures, yet it takes 10years for it to get adopted in
the real world like we exploredall of these things and I think
(37:34):
the the big learning from all ofthose was there were a few that
were really interesting basedon the problem we want to solve,
which was lowering the cost ofcare for a consumer, but they
were really, really complicated,like, for example, starting a
health plan.
Speaker 1 (37:51):
Sure.
Speaker 2 (37:51):
It requires a lot of money and you know it didn't
feel like our strong suit wasgoing and building a health
insurance plan and after 18months of hitting your head
against a wall and thinking youcan make a difference in an
industry that really needs it.
My biggest concern and what ledto me grappling with this
(38:12):
decision to shut it down or notwas we're out of money.
We're not paying ourselves.
Financial runway is low.
Like to be totally candid andhonest, it was to the point
where I've got two months beforeI'm paying my mortgage out of a
heloc.
It's like I'm using the equityin my house to pay down the loan
(38:33):
on my house.
Speaker 1 (38:35):
So you are out of gas , you're empty running on fumes.
Speaker 2 (38:38):
Personally, I've got three young kids, you've got a
family.
I've got a family.
I've got a fourth on the waynow which is new.
That was not, um, that did notfactor into my decision at the
time because that was not partof it, but it was like there's
(39:00):
some real tough decisions thatwe have to make.
You know, do we feel like thereis enough of an inflection,
enough of something moving inthe direction that will help
lower the cost of healthcare forconsumers?
That merits us raising money orgoing in this specific
direction and having theconfidence that it will work out
.
And going through all of thethings that we went through, I
mean, we were grinding likecrazy to try and figure it out
(39:22):
and there were a few things that, um, you had some legs, like
the utilization management.
That one had legs, but thewhole, but the whole problem we
were solving was how do we helpthe insurance company hold on to
more of the money that they get?
It wasn't how can we lower thecost of care.
It was how do we help insurancenot pay doctors?
(39:47):
How do we help them hit that20% number?
So, not mission-driven, it wasnot mission-driven it was.
Speaker 1 (39:50):
we can go make money and build a business.
Did know how do we help themhit that 20% number.
So not mission driven it wasnot mission driven it was.
Speaker 2 (39:53):
we can go make money and build a business.
Did I want to do that?
I didn't Cause.
That's not why I got into it.
Speaker 1 (39:58):
If you, had more time , if you had more money, would
you have kept kept going?
Speaker 2 (40:09):
Because it's not a not a lot of time to build
anything.
Speaker 1 (40:11):
No, it's.
It's not a not a lot of time tobuild anything no, it's, it's
not, and so like I guess myquestion is like if you had
twice, as you know, three years,if you had five years?
Speaker 2 (40:23):
yeah, I, I think I would have, because this is
where we get into failure.
When I was was in high school.
There's this movie called GloryRoad and it talks about the
Texas Western basketball teamwhich was the first team to play
five African-Americans at onetime and in the national
(40:47):
championship there were sevenpeople who played for Texas
Western and they were allAfrican American.
And the movie Glory Road ittalks about the story of how
revolutionary that was.
One of my favorite movies.
I absolutely love it, and oneof the players on the team came
and spoke to my basketball teamin high school and in the movie
there's a scene.
His name is Neville Shedd.
(41:07):
He gets hit in the face.
He's like bleeding.
He comes, he goes off the courtand he comes back with a
catcher's mask on.
He says coach, I'm ready toplay.
Well, prior to that he wasstruggling.
He wasn't giving it his all andthe coach knew that he had more
in him.
And the coach said to himNeville, you quit now, you quit
(41:29):
every day for the rest of yourlife.
I'm a sophomore in high school.
I meet him.
I admire him to the end of theearth for what he did and what
he went through.
So I write that quote on anindex card and it's in my
(41:50):
bedroom and it a quote that,like just, is ingrained in my
head.
So I get to this point withzipper and the first thing I
think to myself is I'm not aquitter, because if I quit now,
I quit every day the rest of mylife.
(42:10):
If I wouldn't have had somewhatof a forcing function to really
dig in and think about that, ofcourse I would have kept going.
I would have said we've got themoney, we'll just pivot, we'll
figure something else out, likewe'll continue to try and solve
this problem.
I am grateful that I had someof those forcing functions,
because not only did it, youknow, force us into making a
(42:33):
decision, it also made merethink what that quote means.
I still believe it, I stilllove the quote, but the way I
think about it now is differentthan how I thought about it
every single day up to thatpoint, because to me, quitting
and failure are two verydifferent things, but in that
moment they were the same thingand that weighed on me.
(42:55):
I couldn't sleep.
I was really grumpy.
At home, you know, my kidswould do one little thing that
annoyed me and I would just likeI couldn't handle it.
And so, yeah, we.
And so, yeah, we would still begoing, I think.
(43:22):
But for reasons that I nowbelieve, I'm grateful that it
went the way that it went,because of the personal learning
that came from it.
I think it's so much morepowerful in the learning.
Like part of entrepreneurshipfor me is the learning and the
growth.
And, just like you know,michael Jordan has this famous
quote like I missed 9,000 shots,I lost 300 games 26 times.
(43:43):
I was trusted to make the gamewinning shot and I missed it.
Like failure is crucial on thepath to success.
And now I look back at that andI think you know it wasn't that
I missed a shot.
It's kind of like I lost a gameand it hurts, but I've done a
better job of forgetting whathappened in terms of the outcome
(44:07):
, while remembering the journeyin terms of the learning, and
spending more time on what's tocome rather than the thing that
I can't change, that's behind me.
Speaker 1 (44:20):
When we talked, I think, I remarked that you're
just in such a healthy headspaceand it took me seven years.
Bubba Page was on this podcast.
Speaker 2 (44:31):
I've listened to that one yeah, yeah, he's like.
Speaker 1 (44:32):
It took me seven years and then I thought, oh man
, I wish that I would.
I could have had thisconversation with you 15, 10
years ago, you know, because itwould have probably changed the
way I process my own failures inbusiness and entrepreneurship.
I think it's mature, it'sinsightful.
I love this idea that quittingand failure and entrepreneurship
(44:53):
.
I think it's mature, it'sinsightful.
I love this idea that quittingand failure are different.
Speaker 2 (44:56):
How are they different?
One of the things I did, Ilooked up the definition of
failure, webster's dictionary.
One of them is lack of success.
I was like ouch, I feel that Istumbled upon instead of looking
at definitions, looking atsynonyms for failure.
One of them was negligence.
(45:20):
I was like that's reallyinteresting.
What is negligence?
Negligence is just likecarelessness.
It's like am I being careless?
No, I care so deeply about this.
(45:44):
To me, quitting when I comparethem, quitting is like I'm just,
I'm giving up, like I'm notcaring anymore.
Where, to me, failure was?
I tried and it didn't work.
So when I look at that quotenow, like you quit now, you quit
every day for the rest of yourlife.
I hope you're failing all thetime.
I hope you're trying to pushthe envelope and innovate and do
meaningful things.
I love sports.
Right, the individual who wonthe batting average in the MLB
(46:10):
this year.
I'm not a big baseball fanwhich is weird because this is
the stat that I use but, like onmy totem pole of sports,
baseball's at the bottom 3-3-2.
So 33.2% of the time that hesteps up to the plate, he is
quote-unquote successful.
Yet he is the absolute best inbaseball.
So when I think about failureand quitting, quitting is like
(46:34):
you know I'm, I'm just going tostop trying at anything.
Speaker 1 (46:37):
I'm not going to step up to the plate again.
Speaker 2 (46:38):
Yeah, I'm not going to step up to the plate again.
Speaker 1 (46:40):
Yeah, cause I'm exhausted, cause I'm yeah.
Seven out of 10 times I can'thit the ball.
Speaker 2 (46:45):
Yeah, failing is I stepped up and I swung.
Failing is I stepped up and Iswung.
Or even sometimes you don'tswing and you and you strike out
.
That's okay, it's.
It's the whole analogy of like,yeah, you fall over, but you
get back up.
And getting up doesn't meangoing to the same thing.
That's the other thing aboutfailure.
I was talking to anentrepreneur recently.
(47:06):
I absolutely love him.
Being so close to him has beenhelpful in this journey and he's
incredibly successful on theoutside.
On the inside, he's open withme about some of the struggles
he has and he said what wouldhappen if your business failed?
He's like, oh man, I can't evenimagine it would be so
(47:27):
devastating.
I was like, okay, I understandthat I felt that way a few
months ago, but now I feel free.
And it's because I think youand I talked about this, saying
there are a lot of people whochoose unhappiness over
(47:49):
uncertainty, and for me, thefear of failure was more about
what happens after the failurethan the failure itself.
It wasn't I feared shutting itdown.
Speaker 1 (48:01):
Yeah.
Speaker 2 (48:06):
But I feared more waking up the next morning, not
building zipper, having twomonths before I'm paying the
decision to shut it down was notthe thing that scared you the
most?
It was like, now, what it wasscary.
Shutting it down it was not thething that scared you the most,
(48:28):
it was like it was scary.
Shutting it down was scary, butit's a small event in a longer
journey of like okay, yeah, weshut it down, but what's going
to happen to my team?
You know what's going to happento me.
Like, what am I going to donext?
I feel lost.
Shutting this down because partof me, like I have this hole in
my heart, like Zipper was ahuge part of me.
They were like who's Jake?
(48:48):
I'm, like I'm the co-founderand CEO of Zipper.
That's who I am.
That's who I am.
August 19th I woke up and I'mnow a failed founder with no
money in the bank and this deepfeeling of I'm worthless because
everything I was I.
(49:10):
If you look at the otherdefinition, you know, a lack of
success.
I, if you look at the otherdefinition, you know a lack of
success and it was like.
You know, I wake up every dayand put on sweats and like meh,
you know it was hard, it stillis hard, but being able to
forget and say you know failureis, the experiment didn't work
(49:32):
and I'm pivoting.
Speaker 1 (49:33):
Yeah.
Speaker 2 (49:33):
Whereas quitting is, I just give up.
Speaker 1 (49:36):
I'm not going to give up.
I'm not going to try anymore.
Speaker 2 (49:38):
I'm going to pivot and you know, I'm still figuring
out what's next.
I'm in the pivot, it's stillvery fresh, but I'm in a much
better headspace.
Speaker 1 (49:49):
It's amazing.
Thank you just for being sovulnerable and open and raw
about the whole experience, andI know it's fresh.
I often think about the wordresilience and I think on
perseverance and I think this isthese are the characteristics
that we look for in greatentrepreneurs and we're like
(50:12):
they never give up, right.
We hear this and I think we weretoo narrow in how we define
that.
We're like we they never giveup on whatever investment or
whatever you know venturethey're involved in.
Right, and I've found myself,um, actually creating a larger
financial and business failurebecause I wasn't going to give
up and I and I wasn't going toquit.
(50:33):
And it was myopic, because thereality is, we can actually
minimize the magnitude of thefailure if we make the decision
earlier.
And there's always this, thisreally nagging question for an
entrepreneur.
That's why I asked you thequestion If you had more money
or time, would you still bedoing this?
You might have had $25 millionor a hundred million dollars and
(50:53):
five years, and you still bedoing this.
You might have had $25 millionor a hundred million dollars and
five years and you still wouldnot have solved the $4 trillion
problem.
And so I just challengeentrepreneurs who are listening
to this to ask themselves isthis the moment where I'm not
going to quit as an entrepreneur, but I need to close this
(51:14):
chapter?
And because this business, thisproduct, this market, this sales
motion is not working?
And if you have the courage todo that earlier in that journey,
you actually minimize that Ifyou would have been doing this
for three or four or five years,you could have been in a worse
spot and you might have solvedfor it.
But this hyper I, this hyperoptimism that more money or more
(51:36):
time will help solve for thelack of sales traction or poor
uni economics, for I'm just likebroadly speaking and and like
that is something that I thinkwe have to guard against as
entrepreneurs.
What are your thoughts on that?
Speaker 2 (51:52):
We totally idolize people who go through really
difficult things and come out ontop, and oftentimes we look at
ourselves through that same lensof it almost shouldn't be
working because that means thatif I succeed, it's all that much
better.
And going back to the way thatI framed my thinking, then
(52:12):
that's what I based my answeroff of.
I'm grateful that we wereforced to stop because it made
me change the way that I thinkabout this.
Um, I don't.
Resilience is not.
Yeah, it's not, it's not myopic, right you?
You talk about it being broader.
(52:33):
For me, it was, um, yeah, I'mgoing to mourn this, but I'm
going to be really introspectiveand I'm going to learn and grow
from it and I'm going tocontinue to try.
Like, one of the things that Idid was I put out a LinkedIn
post and I was very vulnerable,like you know what.
We failed.
We shut it down.
It hurts and it stings.
The amount of people inhealthcare who are executives or
(53:00):
founders, who reached out to mepersonally and expressed the
feelings that they have of I'vebeen doing this for years and
it's not working and it'sdriving me crazy.
That actually blew me away.
It was like, oh hey, I feel thesame thing you feel and I've
been feeling this for a whileand we're five years in and it's
(53:20):
not working.
That hurt, because I'm lookingat them like, oh man, that could
have happened to me.
It's, you know.
Back to entrepreneurship andsuccess.
Success for me has always beenthrough the eyes of others and I
(53:42):
think it's really.
I'm not, I'm not perfect atthis, I'm still trying.
I'm struggling with this, um,you know, because I'll go to
events.
I went to one recently with abunch of founders and it's like
well, what are you working on?
Well, I'm working on being abetter human being right now and
figuring out who I am.
It's such a great honest answer.
It's hard because, people lookat that and they think, well,
(54:04):
you're not interesting, oryou're not going to get me to
this, or you're not.
You know we tend to judge yeah.
Speaker 1 (54:10):
This has been insightful and I was so grateful
and I am so excited to seewhat's next.
In fact, when you first satdown, I said, do you know?
And you're like, not yet, I'mdoing some consulting, I'm
figuring it out, but like Ithink that the key is is that
you're you're probably going tobe batting 300 and and so you're
going to step up to the plateagain.
(54:30):
You're going to take anotherswing and you might take one or
two more, but you're going totake another swing and you might
take one or two more, butyou're going to get that bat on
that ball and it's going to befun to watch that.
And the LinkedIn posts will bedifferent.
And the learning from successis valuable, but the deep
learning, not just aboutbusiness and entrepreneurship,
but about who you are and whatyou're made of and what matters
(54:53):
to you and how you want tooperate.
That learning, um, it comesfrom challenge, comes from the
grind, it comes from, maybe, aneventual business failure, and
that doesn't define you as anentrepreneur at all.
In fact, that the responseyou're getting from this
LinkedIn post, which I want youto actually share.
Uh, as we conclude, I want youto read it, if you're willing?
Speaker 2 (55:16):
Yeah, do you have it?
Yeah, I got it right here.
Yeah, you're on my phone, solet me.
Speaker 1 (55:20):
I haven't read this.
Speaker 2 (55:21):
I took a long time to write this, by the way.
Speaker 1 (55:23):
Honestly, when I read it, I reached out and said, hey
, we need to talk, because Iloved that.
So close.
In proximity to the moment youshut that down, you were on
LinkedIn saying this is whathappened.
This is how I feel about it.
But that response from thecommunity should also tell you
something that you're.
You can't define yourself bythe outcome of zipper alone, and
(55:45):
neither you know the thecommunity is not defining you by
this outcome.
They're defining you and andthey're really defining you by
your response to the outcome.
And so I think this is what's soprofound about your LinkedIn
post, so go ahead and read it.
Speaker 2 (56:01):
Okay, I'll read it, and quickly.
Before I read this, I had aninvestor tell me you know, the
best entrepreneurs run aroundwalls, run through walls, under
walls, over walls, but they alsoknow which walls to stop.
And I think my post is somewhatalong those lines, so I'll read
(56:22):
this.
I haven't read this in a while.
This was probably the beginningof September.
We made the difficult decisiona couple weeks ago to shut down
Zipper.
Yeah, so many good things in mylife have come from not giving
up and digging deeper wheneverything and everyone else
said that it was okay to give up.
(56:43):
Part of what made this decisionso difficult was the wrestle
with whether or not shuttingdown the company was giving up
TLDR.
Our decision to shut downZipper is not giving up.
Starting a company and being afounder is hard.
The highs are higher and thelows are lower.
We had a few highs and our fairshare of lows over the past 16
(57:03):
months.
Everyone asks how it is going,and at times that question is
really hard to answer out loud.
Most people think companybuilding is hard, but they
quickly replace those thoughtsby idolizing those who are
successful in terms of bigfundraising, announcements and
exits.
There are fewer people who,while respecting and admiring
those who beat the odds, see itfor what it actually is the
(57:27):
blood, sweat and tears of givingit your all every day to solve
a problem that you deeply careabout.
Most of the time.
That process isn't glamorous,and that is why I love company
building.
The best things in life are onthe other side of hard.
It didn't turn out as we hadhoped, but we will keep grinding
in other ways to solve theproblems in this world that need
to be solved.
We are not done putting in theblood, sweat and tears to make a
(57:49):
difference.
We will just be making thatdifference in other ways.
I'm so grateful for those whogave their money, time, advice
and more to zipper over the past16 months, and I said so.
What is the next thing?
Not sure yet, but I'm workingon figuring that out as we speak
.
My goal is, and always will bemaking a dent in the world
onward and upward.
Speaker 1 (58:08):
Okay, love it.
Thank you, jake, the caught.
The responses to your messagewere so powerful and I love this
one.
10 out of 10 would no will withan exclamation point.
All caps back you again.
Like that to me is so powerfulright.
Tim, he's got your back man.
Speaker 2 (58:28):
We'll throw a shout out here to Tim.
Tim was the one who told methat comment that I gave right
before I read the post which isthe best entrepreneurs know.
You know they run through walls.
They run around walls, but theyknow which ones to stop at.
Speaker 1 (58:41):
Is he the one that said it?
That was Tim.
This is so insightful.
I want you to look at thecamera and say whatever you want
as your parting thought.
Just a declarative statement.
Speaker 2 (58:50):
My name is Jake Benson.
I'm a failed startup founderwith my first company, zipper,
and failure and quitting are twovery different things.
Speaker 1 (59:00):
I love it.
That's perfect, jake, you'reawesome.
Speaker 2 (59:03):
Joe, thank you.
Speaker 1 (59:04):
Thanks for tuning in to the Real F Word.
The Real F Word is failure, andremember that failure is a
stepping stone, it's not just astumbling block.
Join us next time as wecontinue to explore the journey
of resilience and growth,without ignoring the true costs
personally, professionally andfinancially that comes with
failure.
Keep learning, keep growing andkeep embracing the real stories
of entrepreneurship.
(59:24):
See you next time.
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