September 10, 2024 • 36 mins
What if the key to solving your remote work communication woes lies in a video messaging app? In this episode, we sit down with Josh Little, a seasoned entrepreneur, to unpack the story behind Volley, an asynchronous video messaging app designed to bridge the gaps left by tools like Slack and Zoom during the pandemic. Josh takes us through the exhilarating early days of Volley's development, from the viral response to an initial survey to the rapid prototyping that garnered early traction and significant interest from both users and investors.
The journey wasn't without its hurdles. We delve into the psychological barriers that professionals encounter with video messaging and the challenge of gaining user adoption in a high-risk, low-trust work environment. We discuss the iterative process of refining Volley's features and the stark contrast between workplace communication and more personal, low-risk environments. Despite promising signs from YouTubers and content creators, Volley faced insurmountable obstacles, prompting a pivot toward a consulting model.
Join us as we listen to Josh reflect on the emotional toll of entrepreneurial failure, sharing candid insights on the impact on his health, relationships, and investor expectations. He offers valuable lessons on resilience, the importance of perseverance, and the evolving landscape of asynchronous communication. Despite the setbacks, Josh remains optimistic and driven, believing that his best work is still ahead and determined to repay the trust of his early supporters.
This episode is sponsored by Ampleo. Ampleo offers fraction executives in finance, marketing, and HR to companies of all sizes. Visit ampleo.com to learn more.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
If we had enough capital to last long enough, we
would have figured it out, and alot of people feel like we did
figure it out right at the endwith the consulting piece
allowing asynchronousmicro-consulting.
You know, there's nothing thatdoes that and there are things
like intro that lets you booktime with an expert.
But, that's another synchronousmeeting.
What expert wants anothermeeting on their calendar, right
?
Wouldn't you just love amessage from somebody that had a
(00:21):
question for you that you couldlike get to on your walk?
And that's exactly what weoffered.
But we only had three months torun after that and we saw that
inflection point at the end andthen we're like we got to shut
it down because it was only like5k in monthly revenue that
we're even more painful.
Speaker 2 (00:36):
You're listening to the Real F Word, a podcast that
dives deep into the realities ofentrepreneurial failure, and
each episode features raw,unfiltered.
Welcome to the Real F Word.
I'm so delighted to have JoshLittle here.
(01:01):
He's a five times founder.
He's had plenty of success, buttoday we're not going to talk
about any of it.
We'll talk all about theexperience of building a company
that didn't realize itspotential, that you had to pivot
.
You had to change.
We're going to talk aboutfailure today and hopefully
you'll be open about what otherentrepreneurs can learn from
your experience so that they cande-risk the journey as they
(01:25):
build a product and launch acompany.
Thanks for being here, josh.
Of course, my pleasure.
Thanks for having me.
Tell me a little bit.
First of all, you've started alot of different businesses and
you've raised capital in twodifferent companies.
I want to talk specificallyabout your experience building
Volley.
Tell me a little bit about thejourney.
What was the origin of the ideaand what was the product?
Speaker 1 (01:46):
Yeah.
So when the pandemic hit, I waslooking for my next company,
looking for opportunities, andthe global pandemic or any major
change in society is always agood opportunity to kind of
reflect on what's going tochange, what's going to stay the
same, what's going to staychanged.
So I started thinking deeplyabout what, what effects the
(02:06):
pandemic would have.
Of course, in the early days wedidn't know how long it would
last or if this, you know howbig this problem was.
But companies were starting togo remote and I just knew
communication was going to theway we communicate at work was
going to change fundamentally,or it needed to change because
people were already.
You know what are your options.
You go remote, you're either onSlack, crack or Zoom Doom
(02:30):
either one.
It doesn't quite fit the bill,and I at the time happened to be
having some pretty deep,meaningful conversations with
friends on an app called MarcoPolo, which is a video messaging
app, and these conversationswere like every day, sort of
carrying on a conversation thatwas meaningful, we could get to
it when we wanted to, um, and wewouldn't have had these
(02:53):
conversations in real life, likewe would never have scheduled
time to meet to have thisconversation and you would never
have texted or Slack somebody.
The depth there.
So I felt like async video was,um, a solution to the problems
that were kind of plaguingremote work lack of
communication, loneliness,meeting fatigue those were the
top three.
And so I had the idea of likewhat if Marco Polo had a baby
(03:15):
with Slack?
What would that be like?
And started communicating thatidea, created some prototypes
and started sharing them withpeople, put out a survey I've
never had a survey actually goviral People started sharing
this survey and it just had alittle video of a prototype and
kind of a pitch and people atdifferent companies, government
agencies, started filling it outHundreds of people.
(03:36):
And I was like what?
And I just shared it, like onLinkedIn, and I was like, oh, so
I shut it down immediately andI was like we've got something.
So, and I was like, oh, so Ishut it down immediately and I
was like we've got something.
So pulled a team together,started building Volley May of
2020.
And within a few months, we hadkind of an MVP on iOS and we
realized pretty quickly just,you know, a single platform
(03:59):
wasn't going to be what weneeded.
We needed an Android app, weneeded a desktop app or a web
app.
So we started building thoseand by the fall we had those in
place and started doing aprivate beta.
We had about 700 companies thatwere interested in being early
adopters of Volley.
So we just kind of brought themin in cohorts and started
testing with them and, yeah,just trying to get the
(04:23):
groundswell going with Volley.
Speaker 2 (04:25):
Yeah, I remember the first time I was introduced to
the product.
I was an executive at a localtech business and our CEO said
hey, this is how we're going tocommunicate from now on.
And he would send us Volleys atnight with updates from the day,
and so I used the product and Iknow a lot of people that
continue to use it.
You went out and raised somecapital.
How much did you raise and whatwas the vision for the company
(04:46):
as you were pitching these VCsin Silicon Valley or some here
in Silicon Slopes?
What was that vision that youhad pitched to the investors?
Speaker 1 (04:54):
Yeah.
So it was kind of Marco Polofor work the ultimate team
communication platform.
That was the idea, and peoplewho knew Marco Polo all wondered
like, yeah, why isn't there aMarco Polo for work?
That makes sense, because MarcoPolo's user base was largely
families and lots of femalesactually moms that were
communicating, but it reallywasn't widely adopted at work.
(05:17):
So we were going to build aplatform and it was missing a
number of the features.
You would really need to have arobust messaging app with your
team.
So that was the original visionand we really didn't even need
to pitch it.
People who are hearing aboutwhat we're doing wanted to stuff
money in our pockets, and thiswas, you know, 2020, 2021.
This was the time when, youknow, venture money was flowing
like water, and so we raised 1.4initially, even before we
(05:42):
launched a product, and then,once we launched the product had
enough interest, we raisedanother 4.9 or 4.8.
Speaker 2 (05:48):
In your Series A.
Speaker 1 (05:49):
No, that was a seed round, all your seed round.
Speaker 2 (05:51):
Yeah, what was the expectation in terms of the
financial outcomes that thiscompany could drive for both you
and the management team and theinvestors?
Speaker 1 (05:59):
Yeah, well, I mean we were running the messaging app
playbook and if you look at likesuccessful messaging apps Slack
, telegram, signal, discord thatplaybook doesn't say, hey,
build a really greatmonetization strategy and then
launch a product.
It says build a really greatfree product that people adopt
and grows like wildfire.
(06:20):
Once you do, you're going tofigure out how to monetize this
thing.
So we were really running thatplaybook and because venture
money was so readily available,then we saw no end to our
ability to fundraise andcontinue to fundraise if things
went well.
So we didn't monetize out ofthe gate, building several
(06:40):
products before how much extraeffort and overhead it takes to
build like the whole system ofmonetization and help and
support and all the things thatgo along with that as well as
the.
you know the product that needsto support that.
So we want to just focus all onthe customer experience, free
product and yeah, so March orApril we raised the rest of the
(07:04):
6.3 that we raised for Volley.
Speaker 2 (07:06):
So you had a good team.
You guys have done it before.
You had venture backing some.
Silicon Valley investors, someinvestors here locally, probably
some family offices and angels.
You had a playbook.
There's other companies thathave done it before.
A lot was going right for you,so when were the first signals
that things might not be playingout exactly how you expected?
Speaker 1 (07:27):
Yeah.
So we got some signals prettyearly, but they weren't like
beware, turn around.
They were just like, ooh, thisis going to be harder than we
thought.
And there were three what Iwould call blind sides.
The first was how how reticentpeople were to recording videos
of themselves.
We knew that was going to be aproblem because we know, not
(07:47):
everyone's comfortable.
Speaker 2 (07:48):
I kind of feel that right now Do you?
Speaker 1 (07:50):
Yeah, see, it doesn't bother.
I grew up with a video camerain my stitched to my hand.
Like made tons of videos when Iwas a kid have a.
YouTube channel, like it doesn'teven register for me, but I
know people are sensitive tothat, but we started seeing a
lot of that and they wouldn'tcome out and say I'm vain or I'm
, I don't like, I, I don't likeseeing myself.
(08:12):
They would say, oh, you guysneed filters, or like can I look
at something else while Irecord, or you know things like
that, and we're like what really?
And um, yeah, what we found outis like about 90 of people feel
that recording a video is likeakin to running naked through
times square for them, likepsychologically.
I mean, we've all taken lots ofvideos of other people on
(08:34):
vacations and whatnot.
Very few people have flippedtheir selfie camera around and
spoke and that that freaks themout.
That's not something I do,that's what youtubers do.
So we had that psychology.
That was kind of a blind side,not that it existed, but just
like how prevalent that feelingwas.
(08:55):
Second was the trust risk factor.
When you think about MarcoPolo's user base, if you think
about those conversations likefamilies, that's really high
trust, really low risk, wherethat video messaging has kind of
taken root.
But if you think about aworkplace, it's just the
opposite.
It's typically low trust,unfortunately pretty high risk
to put yourself out there, saysomething that's stupid, that
(09:16):
can be shared, that other peopleyou know can forward to others.
And so that risk, you know,especially as the team size grew
as the team size bigger, therisk felt even higher.
And then the third blind sidewas we didn't realize how much
communication apps are likereligion.
(09:37):
People really.
Hey, you want to use this appto communicate?
That's like, hey, do you wantto come to my church?
It's like that big of a deal topeople and we didn't realize
how big of a deal communicationapp fatigue was.
So those three things showed uppretty early, but none of them
were like deal breakers, none ofthem were like, okay, this is
(09:58):
not going to work.
They were all like you know,these are signals of this is
going to be harder to get towork than we thought.
And you know, like any earlytech product, we just had an MVP
and you know, at this point wedidn't have channels, we didn't
have spaces, we didn't have likea lot of the features that that
are table stakes for amessaging app, especially a
(10:19):
workplace communication app.
So we just we couldn't turnaround or go somewhere else
until we built channels, untilwe built until we had
transcripts.
We need transcripts.
We're not going to know untilwe build transcripts, right.
So we had to build those thingsand so the rest of 2021, it was
really, like you know, throwingfeatures at the problem, which
(10:41):
is never a good idea, but inthis case it's not a bad idea
because we knew even ourselvesthere was, we had a pretty.
We had to have pretty highmotivation to like not have some
of the things that we were usedto in Slack.
Speaker 2 (10:54):
And how big was the team at this point?
Speaker 1 (10:56):
Team at that point was like eight, and so it was
like seven or six engineers, adesigner and me and and yeah, so
we were just trying to getadoption, trying to get teams.
And then I would say the secondthing the next signal we
started seeing this is probablya few months in is we started to
see shark fins, and for thoseof you who don't know, a shark
(11:19):
fin is a graph that looks likeit's going well and then it
doesn't, and so it creates thislike shark fin, and we just saw
this at.
I have thousands of these.
We had thousands of teams adoptvolley.
Every fang company had multipleteams on volley and it was very
much the same like someonewould believe in it.
Somebody would say this is it,this is the future of
(11:39):
communication, kind of like youhad we're communicating on this
they'd invite everyone and andit'd go well until the weakest
link breaks the chain.
And that's another thing that wereally didn't understand is
it's not the CEO that decideswhat communication tool you use.
It's really like the weakestmember, so typically you would
(12:02):
run into Zeds.
So you'd have you know, if youhad a team of 20, a third of the
people would say hell, yes, athird of the people would be
like whatever, and then there'dbe another maybe not third, but
a couple of people who were justlike hell, no, I'm never going
to use it, I'm not going torecord videos of myself.
This thing is evil.
And and they would protest.
And there goes volley right.
Speaker 2 (12:21):
Over and, over and over again.
Every team that adopted it.
You had this pattern Not every.
Speaker 1 (12:25):
And that's the thing there was never and this is true
about most startups it's neverjust like it won't work.
No one will use it, it just.
We had thousands of teams thatwere using it in various levels
of success, right.
Speaker 2 (12:40):
This is the challenge right.
Is to look at the signalthrough the noise and it's tough
because there's so many.
As an entrepreneur, you want tosee all the positive examples
of adoption and marketpenetration and then you may
ignore some of those othersignals that wait a second.
There's 50% of the time, even40% of the time, they're just
not maintaining usage Right.
Speaker 1 (13:02):
Right and yeah.
So those were intimidating, butwe still had functionality and
features to build.
So by the end of the first yearwe kind of realized we're not
going to build our way out ofthis.
It's probably a different usecase, different market,
different workflow.
We're going to have to starthunting, and so we were tracking
everything dozens of signals ofdifferent use cases from, from,
(13:22):
you know, heavy equipment, uhsales in the field, to uh real
estate, to uh support, towhatever Um.
But the most promising signalthat we had at that time was
actually um creators, uhYouTubers that were using it to
um teach a class, to to umengage artists.
So a lot of these educationalYouTube channels will then have
(13:44):
a series of courses and then goalong with the courses, you have
this community where you'retalking about the work and
whatnot, and so we had, like allof the top five YouTube
strategists in the world usingVolley for their courses, for
the community side of theircourses, and we're like
interesting, and you want totalk about a demographic that's
comfortable recording videos ofthemselves youtubers, right.
(14:07):
so we started leaning into tothat small signal and started
building features for them andit started working.
2022 great growth inflection umand uh, we thought we had it
and we were starting to thinkabout monetization at the time.
And that's when uh, like whenSequoia and YC issued letters to
(14:27):
all their portfolio companies,venture winter set in, stock
market crashed and VC basicallyfroze and we didn't realize it
at the time how lasting of aneffect that would have.
We thought this was a hiccup.
So we did what everyone elsewas doing try to raise a little
bit more money.
You know, try to.
We reduced some of ourworkforce.
(14:49):
We went from like 12 to 10people so we weren't big ever
Just to try to extend our runway, which we did.
We got to over a year because wehad like six months of runway
in May of 2022.
And that happened.
So we extended the runway andwe thought we could weather it
out and we worked with thisaudience.
We tried to monetize.
(15:10):
We created a pro version ofVolley where you could pay for
extra features.
That wasn't it and we kind ofknew that wasn't it, but it only
took us three weeks to build.
So we shipped that and then westarted building.
What we eventually knew wouldprobably be more successful
would be allowing for people tocharge for experiences they
created on Volley.
So I think micro-consulting orpaid group programs.
(15:31):
It's kind of what our creatorsand coaches and consultants on
Volley were using it for, and sowe were just paving the cow
paths, doing what they weredoing and making it a lot easier
for them to monetize what theywere doing.
And making it a lot easier forthem to monetize whether,
instead of putting a stack ofStripe and Substack together
with Volley and we just builtthose features to allow you to
put in a number, create youroffer, send out your link and
(15:54):
it's all automatic.
So we made a hasty attempt,kind of nearer the end, to
monetize in that way.
That was also successful, greatgrowth, inflection but the
revenue was just not enough tosave the day and by that point,
all of our investors, like they,had already invested enough in
Volley.
(16:14):
Nobody wanted another bite ofthe apple.
I pitched 30 or so moreinvestors that were in the
creator monetization spacenothing, and at this point, end
of 2022, nobody's investing,like almost zero investments
were happening at the time, nomatter what anyone wants to say.
So we tried to sell it Couldn'tget a deal done.
(16:35):
We got close with, like,discord and Vimeo and a couple
others, but couldn't get a dealdone.
So, may of 2023, I had toannounce a shutdown because we
needed at least 60 days foreveryone to fulfill what they
just sold on Volley to be ableto do the consulting offer or
whatever.
Otherwise we'd have to refundall of that money.
(16:57):
So we did it and got it shutdown cleanly.
Speaker 2 (17:01):
Tell me about that decision to shut it down.
Yeah, what are theconversations you're having with
your investors, with yourmanagement team.
Speaker 1 (17:08):
Tell me about that, yeah, I mean everyone is eyes
wide open.
I've been told I'm quite goodat investor updates and team
updates Like I share openly.
Everyone can see the P&L,everyone can see what everyone's
making.
You know, like I'm verytransparent when running a
company, so I do weekly updateswith the team.
Everyone knows what's going onwhere we're at.
(17:29):
So they're getting theplay-by-play.
Investors get monthly updates,but they're very in-depth.
So all the investors that werepaying attention to my monthly
updates knew exactly what wasgoing on, felt like we were
making all the right moves.
You know it was either monetize, sell it or raise money.
Those are the three options,you know.
And nope, nope and nope,unfortunately.
(17:51):
So everyone was kind of eyeswide open in the know when we
got to that place and you know Iwould say we had dozens of
contemporaries.
Like a lot of people were kindof smelling that same signal
that I was when the pandemic hit.
You know that communication isgoing to change and async video
is a solution, so that we haddozens of other companies that
(18:14):
were kind of competitors orcopycats or whatever you want to
say, and we did better than anyof them, which I'm proud to say
, but just not good enough notescape velocity.
We never reached escapevelocity and, given the
trajectory, I just couldn't seeit happening Like if we had six
more months or 12 more months.
We needed years, not monthsmore.
Speaker 2 (18:37):
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What was the toughestconversation you had as you shut
down something you had beenbuilding and were excited about
and had an interesting productgreat investor group trajectory
at one point.
Speaker 1 (20:08):
Well, I mean that's why I say investors who were
paying attention, because therewere a couple of investors that
just weren't paying attentionand they didn't know all of the
things that we did, didn't careto understand the full story and
they felt like we just gave up,right, and so those
conversations were hard to oneinvestor, like try to rip me up
on LinkedIn and like if you onlyknew, if you only knew.
(20:32):
But you know, 98% of investorssaid things like you guys ran a
flawless performance, like yourexecution was near flawless.
And I really feel like.
I feel like I did the best workof my life.
I built the best product I'veever built in my life.
Um, and I you know, I hang myhead pretty high based on the
(20:52):
work that we did Didn't see thescore on the scoreboard like
we'd like to see, but lookingback, it's hard to find like
obvious gaps or holes or baddecisions that we I'm not saying
there weren't hindsight.
Well, that's what I want totalk about, cause it's hard to
find like obvious gaps or holesor bad decisions.
I'm not saying there weren't.
Speaker 2 (21:06):
Hindsight's easy.
Well, that's what I want totalk about, because it's easy to
attribute our failures tocircumstances or economy or
capital constraints, competitivedynamics that are outside of
our control.
But, like for entrepreneursthat are listening, what are the
things inside of your controlthat you would have done
differently?
What are some of the keylearnings your control that you
would have done differently?
What are some of the the keylearnings, some things you won't
(21:28):
do again.
Speaker 1 (21:30):
Yeah, I think I probably this is easy in
hindsight in in unfortunately.
I do feel like, given the data Ihad, I'd probably do the exact
stinking same thing, you know,if I had the same data moving
forward.
But we should have.
We should have pivoted a littleearlier from the team thing,
but that's what everyoneinvested in, that's what
(21:51):
everyone thought like.
This is the time for thisproduct.
We just had to get it right,you know.
So we didn't want to move awayfrom that too fast.
And another thing in this I canargue both sides of this.
Another thing we probablyshould have done was monetize
from day one.
Um, but that's not themessaging playbook and um, uh,
(22:12):
and while that would have helpedus orient on a willingness to
pay, like a user that's willingto pay and build around them, it
may not have helped us find,ultimately, what I think would
have been successful with iswhich is that consulting,
coaching, you know, monetizingexperiences you're creating on
Volley, that product.
Because I think if we monetizedfrom day one, we would have
(22:35):
monetized something very similarto what Slack and other team
communications products aredoing and we would have found a
handful of people that werewilling to pay.
Like I said, it wasn't a zerothat you um, and we would have
just oriented around them andnever looked further.
So we probably should havemonetized earlier, but I could
also see where that would havegot us stuck in the mud earlier.
Speaker 2 (22:58):
For sure, tell me about the like.
We sometimes ignore thepersonal cost of building
something and it failing.
Speaker 1 (23:05):
Yeah.
Speaker 2 (23:06):
How did you deal with this kind of emotionally?
What was your kind of reactionin the quiet moments where
you're sitting playing guitar orsinging.
Speaker 1 (23:13):
I know you're a musician.
Speaker 2 (23:15):
How are you feeling?
Speaker 1 (23:17):
Oh yeah, just demoralized, humbled, all the
words, like confused, cause it'snot like I wasn't doing
something that I knew I shouldbe doing, like I was doing
everything that I could possiblythink of, and so was the rest
of the team, and and when you'rein a situation like that and
and you're just not seeing, youknow you're just not seeing it
(23:41):
work, it's, it's reallyfrustrating, you know you're
just not seeing it work, it'sreally frustrating.
And you know how did I dealwith it?
Food, food's a, it's a goodmedicine, like it's effective,
it works.
Speaker 2 (23:53):
So I gained like 50 pounds.
50 pounds, yeah, I put on 50pounds.
Yeah what?
Speaker 1 (23:57):
was your food of choice?
Oh, nachos, nachos, right, it'sthe most delicious thing you
can put together on the earth.
No, I don't know.
How are your sleeping patterns?
Sleep is good.
Yeah, I've always slept.
Good.
Speaker 2 (24:12):
So not a problem, Talk to me about your family
relationships some of your maybeco-founder relationships.
What was the on any type ofpersonal relationship that you
had?
Speaker 1 (24:23):
Yeah, you know, other than the couple of investors
that weren't quite payingattention, I I feel like they're
stronger, stronger, like Ithink most investors that were
in volley would probably bet onme again, as crazy as that
sounds that you know, if I had anew idea this month and was
going to pull the team togetherjust based on how we executed
(24:46):
like it was, it was a.
We played a really good game.
I'm proud of that.
But, uh, you know, it's alwayshard to not return somebody's
money.
Um, you know, at a minimum Iwant to be able to return their
money, right, um, uh, but Ican't imagine a situation where
we hadn't and and family.
You know, my wife and kids know,they know the game we're
(25:09):
playing and you know, if you'regoing to ride a horse, you're
going to fall off Like there's.
There's no way around it.
And if you ride a horse, aslong as I have, you know, you're
going to get some bumps andbruises, and I've had them
before.
So this is just another one ofthem.
Unfortunately, brews, and I'vehad them before, so this was
just another one of them,unfortunately.
Speaker 2 (25:31):
Yeah, that was my experience too when I drove once
from St George to Ogden in oneday and I started early in the
morning and I just met with abunch of the local investors
that I had raised money fromsome family offices, some of the
angels- that you probably knowwell and I remember sitting at a
coffee shop up in Ogden right,and I was actually pretty
distraught.
Speaker 1 (25:44):
Yeah.
Speaker 2 (25:44):
I'd lost more than 6 million bucks, um, but this
particular investor hadsupported me in a couple of
different ventures and I satthere and I was a little
emotional and I just apologized.
I said it's gone Like there'sthere's no way to recoup the
equity.
I've lost all of yourinvestment.
And it was um.
It was extraordinary to see hisresponse to that.
(26:06):
He asked how are you doing?
How's?
your family, and he looked at meand said essentially what some
of your investors said, whichwas, if you came to me today
asking me to invest in you again, I would do it.
I was prepared for eitheroutcome here, and that, to me,
was maybe the most profoundconversation I've ever had with
an investor, more than investorsapplauding you when you're
(26:28):
succeeding to have an investorsupport you when you've failed
is really heartwarming anduplifting and encouraging.
It may be the single mostconfidence building comment
anyone has ever told me, becauseit's in the face of like me
losing.
I probably lost a milliondollars of his money.
Right, he was one of.
He wasn't our largest investor,but he was someone I had a
(26:50):
personal relationship with andthat was incredibly painful and
it sounds like you had some ofthose experiences as well.
Speaker 1 (26:55):
I had a lot of those conversations.
Yeah, one in particular JacobMullins of Shasta Ventures,
which is a VC firm in the BayArea.
They put a million and he wasprobably more ready to shut
Volley down.
Not probably he was more readyto shut Volley down than I was,
period, just because he had sawhow hard we had worked.
(27:16):
And if you work that hard atsomething it'll go.
And if it's not going, you justdon't have product market fit,
it's not the right time, or it'snot the right time or not the
right product or whatever.
Um, and you know, in a lot ofthe conversations he would, yeah
, ask about me and and everytime he'd be like, okay, what
are you guys doing next?
Like we'll back it, like let'sbuild something else.
(27:37):
And I was like, oh man, that'sawesome for you to say, but I'm
pretty tired and I'm going totake a nap so I want to take a
couple of weeks or months ofnaps.
So not sure that I'm ready totake another bite yet or another
swing.
Speaker 2 (27:50):
Yeah, that's certainly how I felt after my
last venture, as I startedplaying guitar again after 20
years and skied a lot and justhad to breathe because, of that
intensity.
I mean, like when you're tryingto solve a puzzle, it feels
kind of impossible.
You're trying everything right,you're modifying the product,
You're throwing features at theproduct, you're talking to
customers You're working onpartnerships, right, you're
(28:12):
looking for an acquisition, astrategic investor like, and
you're just like tryingeverything and anything right To
get this to go and it's notgoing.
It's emotionally exhausting.
Speaker 1 (28:22):
Yeah, it's mentally taxing.
Speaker 2 (28:24):
It's humbling.
Yeah, for sure, for sure.
Do you think the outcome wouldhave been different if you would
have had more capital?
Speaker 1 (28:30):
Because it's easy to blame.
Speaker 2 (28:31):
I've always thought oh well, if I had more capital,
like I could have like pushedthrough and figured out the
right product, market fit,figured out the right customer,
built the feature set mycustomers wanted.
Speaker 1 (29:08):
Yes.
Speaker 2 (29:08):
If we had more.
Speaker 1 (29:09):
Let me try to unpack that I that gives us the benefit
of time and space.
That lets you say what you needto say, move on with your day,
have a meaningful conversationwhen you come back to it and
listen to others on 2X and youcan speak seven times faster
than like all of the thingsabout async video, I can't
believe that a global pandemicdidn't change people's sentiment
there.
(29:29):
I can't believe it.
But at the same time I don'tknow what's coming down the road
that's going to change people'ssentiment.
It could be Elon tweetssomething.
It could be some global, Idon't know some other product,
but I do know the TikTok andSnapchat generation are a lot
more comfortable with asyncvideo than than um existing
(29:52):
generations that are in chargein the workforce.
Right, my kids are all about itall day, every day all day,
every day.
My kids don't even type anythingin Google, they just talk to
Google and we're Siri, right, soI see a future generation that,
um, that would so if we, if wehad enough capital to last long
enough, we would have figured itout, and a lot of people feel
like we did figure it out rightat the end with the consulting
(30:15):
piece allowing asynchronousmicro-consulting.
You know, there's nothing thatdoes that, and there are things
like intro that lets you booktime with an expert but, that's
another synchronous meeting.
What expert wants anothermeeting on their calendar, right
?
Wouldn't you just love amessage from somebody that had a
question for you that you couldlike get to on your walk?
And that's exactly what weoffered.
But we only had three months torun after that and we saw that
(30:39):
inflection point at the end andthen we're like we got to shut
it down because it was only like5k in monthly revenue that
we're getting Even more painful.
Speaker 2 (30:46):
right, it's because you're like, ah, we had it.
Speaker 1 (30:49):
We had it right there .
Speaker 2 (30:55):
So tell me about the word failure.
We don't use it.
I mean, we probably have onlysaid it a few times in this
whole conversation.
I understand like, asentrepreneurs, we try to frame
failure in ways that maybeprotect ourselves from
acknowledging our owndeficiencies or decision making.
Do you feel like Volley was afailure?
Speaker 1 (31:06):
It depends on what question you're asking.
I failed to return capital tomy investors.
So, yes, I failed at doing that.
I didn't fail at building agreat product, building a killer
team, engaging our users,building a product that some
people loved.
I didn't fail at executing aswell as anyone could at that
(31:30):
venture.
So I didn't fail at thosethings.
We just failed getting theproduct to reach the measure of
its creation.
You kind of like you said it'strue potential.
We failed at figuring out theexact right mix for the right
people at the right time to getit there and ultimately, how
does this failure change yourperspective of entrepreneurship,
(31:52):
or has it?
Speaker 2 (31:53):
I mean, is it going to change the way you build your
next business?
I know that you're stillworking on Volley right it
sounds like there's still afuture.
So the Volley story hasn't beenit's not fully over.
Speaker 1 (32:04):
I've acquired it.
We've rebuilt it and relaunchedit.
It's just a product that needsto exist.
It's too dang good to see itjust go in the trash.
So I don't know if it's a greatfinancial move, but it's a
labor of love and it also thestory's not over, so I get to
save that right.
We'll just see what happens.
And our plan is just let Volleygrow organically over time.
(32:26):
And it grows, you know 5% to10% a week and you know those
gains stack up over timeorganically.
People invite other people insome stick some stone.
We'll keep bugs fixed, buildsome new features and we'll see
where it goes.
But it's it's not a full-timeeffort for anyone on the team at
this point.
Um, labor of love, but how hasit changed me?
(32:47):
I think you'd have to be apsychopath just to like not be
phased at all by by anexperience like this.
Um, because a lot of the peopleI raised money from were my
friends, close friends, um, andmany have become friends now,
right, and so I raised a bunchof money for my friends that I
(33:08):
wasn't able to return, um, andthat that hurts, you know, and
it makes me a little gun shy, itmakes me worried about
potentially doing that again.
And do I really have it?
And ask, ask some of thosefoundational questions.
But I, I came from ruralMichigan where I worked in
restaurants and I was a highschool teacher, you know, and,
(33:29):
and I've made my way through allthe twists and changes to be an
entrepreneur, you know, and,and I've made my way through all
the twists and changes to be anentrepreneur, to be a tech
entrepreneur, I, I, I dosomething where people will give
me millions of dollars to buildmy dream willingly, and you
can't, you can't think thatthat's not a privilege, you know
.
So it's an absolute privilege todo what I do.
(33:50):
Um, it is confidence shaking tohave a failure, but, um, but
I'm honored to do what I do andI feel like if, if I don't do it
, it's not filling the measureof my creation.
Uh, doing what I potentiallycould do, like being a tech
entrepreneur, is the highestpaid potential career in the
world right, if you get it right.
You know, like the richestfolks on earth did what I do and
(34:13):
and I'm good enough to thinkthat I, I could do that if I, if
I got the right product in theright time, the right team and
um, just got to find that soyou're gonna get back on the
horse get back on the horse.
Maybe not this week but, uh,maybe this year we'll see.
I've got seven ideas that I'mkind of playing around with.
Speaker 2 (34:29):
Yeah, thank you for your candor about just the
personal costs, the emotionaltoll it takes, Certainly the
pain of raising money frompeople that we care about, our
friends and investors, and notbeing able to return that money.
Like that's, I think, the storythat we often overlook when we
glorify the successes right.
(34:50):
And we see the entrepreneursthat take companies public and
sell for hundreds of millions ofdollars.
It's easy to focus on that, andreally the outcome that you
experienced happens most of thetime, but we rarely talk about
those outcomes, and then that'swhere I think the richest
lessons and learning are inthose, and so you've shared your
insight in a way that I justreally appreciate, josh, and if
(35:10):
you came to me and you wereraising money, I would bet on
you too, because I feel likethat the accumulation of those
experiences actually de-risksthe journey for you and for your
investors moving forward.
Speaker 1 (35:24):
I really think so.
I really feel like my best workis ahead.
I feel like Volley was the bestwork of my life.
Didn't show on the scoreboard,but all of those lessons and
learnings are paid forward tothe next thing right um, and and
so I'm excited about it.
Speaker 2 (35:38):
Not sure what that is , but I'm excited about whatever
that is yeah, I always havethis like vision in my mind of
like, um, you know, if I, if Iever hit the grand slam, right,
I'm going back and driving fromsaint george to ogden again and
just like handing checks out andjust saying thank you so much
for believing in me.
That one didn't turn out butthis one did, and it was really
on the back of those investorsand those experiences and that
(36:03):
capital that they entrusted mewith, that I was able to get to
an outcome, a really positivefinancial outcome.
Speaker 1 (36:10):
So, anyway, now that's public, so I guess all my
investors will be like I'll bewaiting at the cafe for the
check.
Here we go, joe.
Yeah, where is it at man?
That's right.
Thank you so much, josh, ofcourse.
Yeah, thanks for having me.
I'm Josh Little and I failedwhile daring greatly.
Speaker 2 (36:24):
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.
If we had enough capital to last long enough, we
would have figured it out, and alot of people feel like we did
figure it out right at the endwith the consulting piece
allowing asynchronousmicro-consulting.
You know, there's nothing thatdoes that and there are things
like intro that lets you booktime with an expert.
But, that's another synchronousmeeting.
What expert wants anothermeeting on their calendar, right
?
Wouldn't you just love amessage from somebody that had a
(00:21):
question for you that you couldlike get to on your walk?
And that's exactly what weoffered.
But we only had three months torun after that and we saw that
inflection point at the end andthen we're like we got to shut
it down because it was only like5k in monthly revenue that
we're even more painful.
Speaker 2 (00:36):
You're listening to the Real F Word, a podcast that
dives deep into the realities ofentrepreneurial failure, and
each episode features raw,unfiltered.
Welcome to the Real F Word.
I'm so delighted to have JoshLittle here.
(01:01):
He's a five times founder.
He's had plenty of success, buttoday we're not going to talk
about any of it.
We'll talk all about theexperience of building a company
that didn't realize itspotential, that you had to pivot
.
You had to change.
We're going to talk aboutfailure today and hopefully
you'll be open about what otherentrepreneurs can learn from
your experience so that they cande-risk the journey as they
(01:25):
build a product and launch acompany.
Thanks for being here, josh.
Of course, my pleasure.
Thanks for having me.
Tell me a little bit.
First of all, you've started alot of different businesses and
you've raised capital in twodifferent companies.
I want to talk specificallyabout your experience building
Volley.
Tell me a little bit about thejourney.
What was the origin of the ideaand what was the product?
Speaker 1 (01:46):
Yeah.
So when the pandemic hit, I waslooking for my next company,
looking for opportunities, andthe global pandemic or any major
change in society is always agood opportunity to kind of
reflect on what's going tochange, what's going to stay the
same, what's going to staychanged.
So I started thinking deeplyabout what, what effects the
(02:06):
pandemic would have.
Of course, in the early days wedidn't know how long it would
last or if this, you know howbig this problem was.
But companies were starting togo remote and I just knew
communication was going to theway we communicate at work was
going to change fundamentally,or it needed to change because
people were already.
You know what are your options.
You go remote, you're either onSlack, crack or Zoom Doom
(02:30):
either one.
It doesn't quite fit the bill,and I at the time happened to be
having some pretty deep,meaningful conversations with
friends on an app called MarcoPolo, which is a video messaging
app, and these conversationswere like every day, sort of
carrying on a conversation thatwas meaningful, we could get to
it when we wanted to, um, and wewouldn't have had these
(02:53):
conversations in real life, likewe would never have scheduled
time to meet to have thisconversation and you would never
have texted or Slack somebody.
The depth there.
So I felt like async video was,um, a solution to the problems
that were kind of plaguingremote work lack of
communication, loneliness,meeting fatigue those were the
top three.
And so I had the idea of likewhat if Marco Polo had a baby
(03:15):
with Slack?
What would that be like?
And started communicating thatidea, created some prototypes
and started sharing them withpeople, put out a survey I've
never had a survey actually goviral People started sharing
this survey and it just had alittle video of a prototype and
kind of a pitch and people atdifferent companies, government
agencies, started filling it outHundreds of people.
(03:36):
And I was like what?
And I just shared it, like onLinkedIn, and I was like, oh, so
I shut it down immediately andI was like we've got something.
So, and I was like, oh, so Ishut it down immediately and I
was like we've got something.
So pulled a team together,started building Volley May of
2020.
And within a few months, we hadkind of an MVP on iOS and we
realized pretty quickly just,you know, a single platform
(03:59):
wasn't going to be what weneeded.
We needed an Android app, weneeded a desktop app or a web
app.
So we started building thoseand by the fall we had those in
place and started doing aprivate beta.
We had about 700 companies thatwere interested in being early
adopters of Volley.
So we just kind of brought themin in cohorts and started
testing with them and, yeah,just trying to get the
(04:23):
groundswell going with Volley.
Speaker 2 (04:25):
Yeah, I remember the first time I was introduced to
the product.
I was an executive at a localtech business and our CEO said
hey, this is how we're going tocommunicate from now on.
And he would send us Volleys atnight with updates from the day,
and so I used the product and Iknow a lot of people that
continue to use it.
You went out and raised somecapital.
How much did you raise and whatwas the vision for the company
(04:46):
as you were pitching these VCsin Silicon Valley or some here
in Silicon Slopes?
What was that vision that youhad pitched to the investors?
Speaker 1 (04:54):
Yeah.
So it was kind of Marco Polofor work the ultimate team
communication platform.
That was the idea, and peoplewho knew Marco Polo all wondered
like, yeah, why isn't there aMarco Polo for work?
That makes sense, because MarcoPolo's user base was largely
families and lots of femalesactually moms that were
communicating, but it reallywasn't widely adopted at work.
(05:17):
So we were going to build aplatform and it was missing a
number of the features.
You would really need to have arobust messaging app with your
team.
So that was the original visionand we really didn't even need
to pitch it.
People who are hearing aboutwhat we're doing wanted to stuff
money in our pockets, and thiswas, you know, 2020, 2021.
This was the time when, youknow, venture money was flowing
like water, and so we raised 1.4initially, even before we
(05:42):
launched a product, and then,once we launched the product had
enough interest, we raisedanother 4.9 or 4.8.
Speaker 2 (05:48):
In your Series A.
Speaker 1 (05:49):
No, that was a seed round, all your seed round.
Speaker 2 (05:51):
Yeah, what was the expectation in terms of the
financial outcomes that thiscompany could drive for both you
and the management team and theinvestors?
Speaker 1 (05:59):
Yeah, well, I mean we were running the messaging app
playbook and if you look at likesuccessful messaging apps Slack
, telegram, signal, discord thatplaybook doesn't say, hey,
build a really greatmonetization strategy and then
launch a product.
It says build a really greatfree product that people adopt
and grows like wildfire.
(06:20):
Once you do, you're going tofigure out how to monetize this
thing.
So we were really running thatplaybook and because venture
money was so readily available,then we saw no end to our
ability to fundraise andcontinue to fundraise if things
went well.
So we didn't monetize out ofthe gate, building several
(06:40):
products before how much extraeffort and overhead it takes to
build like the whole system ofmonetization and help and
support and all the things thatgo along with that as well as
the.
you know the product that needsto support that.
So we want to just focus all onthe customer experience, free
product and yeah, so March orApril we raised the rest of the
(07:04):
6.3 that we raised for Volley.
Speaker 2 (07:06):
So you had a good team.
You guys have done it before.
You had venture backing some.
Silicon Valley investors, someinvestors here locally, probably
some family offices and angels.
You had a playbook.
There's other companies thathave done it before.
A lot was going right for you,so when were the first signals
that things might not be playingout exactly how you expected?
Speaker 1 (07:27):
Yeah.
So we got some signals prettyearly, but they weren't like
beware, turn around.
They were just like, ooh, thisis going to be harder than we
thought.
And there were three what Iwould call blind sides.
The first was how how reticentpeople were to recording videos
of themselves.
We knew that was going to be aproblem because we know, not
(07:47):
everyone's comfortable.
Speaker 2 (07:48):
I kind of feel that right now Do you?
Speaker 1 (07:50):
Yeah, see, it doesn't bother.
I grew up with a video camerain my stitched to my hand.
Like made tons of videos when Iwas a kid have a.
YouTube channel, like it doesn'teven register for me, but I
know people are sensitive tothat, but we started seeing a
lot of that and they wouldn'tcome out and say I'm vain or I'm
, I don't like, I, I don't likeseeing myself.
(08:12):
They would say, oh, you guysneed filters, or like can I look
at something else while Irecord, or you know things like
that, and we're like what really?
And um, yeah, what we found outis like about 90 of people feel
that recording a video is likeakin to running naked through
times square for them, likepsychologically.
I mean, we've all taken lots ofvideos of other people on
(08:34):
vacations and whatnot.
Very few people have flippedtheir selfie camera around and
spoke and that that freaks themout.
That's not something I do,that's what youtubers do.
So we had that psychology.
That was kind of a blind side,not that it existed, but just
like how prevalent that feelingwas.
(08:55):
Second was the trust risk factor.
When you think about MarcoPolo's user base, if you think
about those conversations likefamilies, that's really high
trust, really low risk, wherethat video messaging has kind of
taken root.
But if you think about aworkplace, it's just the
opposite.
It's typically low trust,unfortunately pretty high risk
to put yourself out there, saysomething that's stupid, that
(09:16):
can be shared, that other peopleyou know can forward to others.
And so that risk, you know,especially as the team size grew
as the team size bigger, therisk felt even higher.
And then the third blind sidewas we didn't realize how much
communication apps are likereligion.
(09:37):
People really.
Hey, you want to use this appto communicate?
That's like, hey, do you wantto come to my church?
It's like that big of a deal topeople and we didn't realize
how big of a deal communicationapp fatigue was.
So those three things showed uppretty early, but none of them
were like deal breakers, none ofthem were like, okay, this is
(09:58):
not going to work.
They were all like you know,these are signals of this is
going to be harder to get towork than we thought.
And you know, like any earlytech product, we just had an MVP
and you know, at this point wedidn't have channels, we didn't
have spaces, we didn't have likea lot of the features that that
are table stakes for amessaging app, especially a
(10:19):
workplace communication app.
So we just we couldn't turnaround or go somewhere else
until we built channels, untilwe built until we had
transcripts.
We need transcripts.
We're not going to know untilwe build transcripts, right.
So we had to build those thingsand so the rest of 2021, it was
really, like you know, throwingfeatures at the problem, which
(10:41):
is never a good idea, but inthis case it's not a bad idea
because we knew even ourselvesthere was, we had a pretty.
We had to have pretty highmotivation to like not have some
of the things that we were usedto in Slack.
Speaker 2 (10:54):
And how big was the team at this point?
Speaker 1 (10:56):
Team at that point was like eight, and so it was
like seven or six engineers, adesigner and me and and yeah, so
we were just trying to getadoption, trying to get teams.
And then I would say the secondthing the next signal we
started seeing this is probablya few months in is we started to
see shark fins, and for thoseof you who don't know, a shark
(11:19):
fin is a graph that looks likeit's going well and then it
doesn't, and so it creates thislike shark fin, and we just saw
this at.
I have thousands of these.
We had thousands of teams adoptvolley.
Every fang company had multipleteams on volley and it was very
much the same like someonewould believe in it.
Somebody would say this is it,this is the future of
(11:39):
communication, kind of like youhad we're communicating on this
they'd invite everyone and andit'd go well until the weakest
link breaks the chain.
And that's another thing that wereally didn't understand is
it's not the CEO that decideswhat communication tool you use.
It's really like the weakestmember, so typically you would
(12:02):
run into Zeds.
So you'd have you know, if youhad a team of 20, a third of the
people would say hell, yes, athird of the people would be
like whatever, and then there'dbe another maybe not third, but
a couple of people who were justlike hell, no, I'm never going
to use it, I'm not going torecord videos of myself.
This thing is evil.
And and they would protest.
And there goes volley right.
Speaker 2 (12:21):
Over and, over and over again.
Every team that adopted it.
You had this pattern Not every.
Speaker 1 (12:25):
And that's the thing there was never and this is true
about most startups it's neverjust like it won't work.
No one will use it, it just.
We had thousands of teams thatwere using it in various levels
of success, right.
Speaker 2 (12:40):
This is the challenge right.
Is to look at the signalthrough the noise and it's tough
because there's so many.
As an entrepreneur, you want tosee all the positive examples
of adoption and marketpenetration and then you may
ignore some of those othersignals that wait a second.
There's 50% of the time, even40% of the time, they're just
not maintaining usage Right.
Speaker 1 (13:02):
Right and yeah.
So those were intimidating, butwe still had functionality and
features to build.
So by the end of the first yearwe kind of realized we're not
going to build our way out ofthis.
It's probably a different usecase, different market,
different workflow.
We're going to have to starthunting, and so we were tracking
everything dozens of signals ofdifferent use cases from, from,
(13:22):
you know, heavy equipment, uhsales in the field, to uh real
estate, to uh support, towhatever Um.
But the most promising signalthat we had at that time was
actually um creators, uhYouTubers that were using it to
um teach a class, to to umengage artists.
So a lot of these educationalYouTube channels will then have
(13:44):
a series of courses and then goalong with the courses, you have
this community where you'retalking about the work and
whatnot, and so we had, like allof the top five YouTube
strategists in the world usingVolley for their courses, for
the community side of theircourses, and we're like
interesting, and you want totalk about a demographic that's
comfortable recording videos ofthemselves youtubers, right.
(14:07):
so we started leaning into tothat small signal and started
building features for them andit started working.
2022 great growth inflection umand uh, we thought we had it
and we were starting to thinkabout monetization at the time.
And that's when uh, like whenSequoia and YC issued letters to
(14:27):
all their portfolio companies,venture winter set in, stock
market crashed and VC basicallyfroze and we didn't realize it
at the time how lasting of aneffect that would have.
We thought this was a hiccup.
So we did what everyone elsewas doing try to raise a little
bit more money.
You know, try to.
We reduced some of ourworkforce.
(14:49):
We went from like 12 to 10people so we weren't big ever
Just to try to extend our runway, which we did.
We got to over a year because wehad like six months of runway
in May of 2022.
And that happened.
So we extended the runway andwe thought we could weather it
out and we worked with thisaudience.
We tried to monetize.
(15:10):
We created a pro version ofVolley where you could pay for
extra features.
That wasn't it and we kind ofknew that wasn't it, but it only
took us three weeks to build.
So we shipped that and then westarted building.
What we eventually knew wouldprobably be more successful
would be allowing for people tocharge for experiences they
created on Volley.
So I think micro-consulting orpaid group programs.
(15:31):
It's kind of what our creatorsand coaches and consultants on
Volley were using it for, and sowe were just paving the cow
paths, doing what they weredoing and making it a lot easier
for them to monetize what theywere doing.
And making it a lot easier forthem to monetize whether,
instead of putting a stack ofStripe and Substack together
with Volley and we just builtthose features to allow you to
put in a number, create youroffer, send out your link and
(15:54):
it's all automatic.
So we made a hasty attempt,kind of nearer the end, to
monetize in that way.
That was also successful, greatgrowth, inflection but the
revenue was just not enough tosave the day and by that point,
all of our investors, like they,had already invested enough in
Volley.
(16:14):
Nobody wanted another bite ofthe apple.
I pitched 30 or so moreinvestors that were in the
creator monetization spacenothing, and at this point, end
of 2022, nobody's investing,like almost zero investments
were happening at the time, nomatter what anyone wants to say.
So we tried to sell it Couldn'tget a deal done.
(16:35):
We got close with, like,discord and Vimeo and a couple
others, but couldn't get a dealdone.
So, may of 2023, I had toannounce a shutdown because we
needed at least 60 days foreveryone to fulfill what they
just sold on Volley to be ableto do the consulting offer or
whatever.
Otherwise we'd have to refundall of that money.
(16:57):
So we did it and got it shutdown cleanly.
Speaker 2 (17:01):
Tell me about that decision to shut it down.
Yeah, what are theconversations you're having with
your investors, with yourmanagement team.
Speaker 1 (17:08):
Tell me about that, yeah, I mean everyone is eyes
wide open.
I've been told I'm quite goodat investor updates and team
updates Like I share openly.
Everyone can see the P&L,everyone can see what everyone's
making.
You know, like I'm verytransparent when running a
company, so I do weekly updateswith the team.
Everyone knows what's going onwhere we're at.
(17:29):
So they're getting theplay-by-play.
Investors get monthly updates,but they're very in-depth.
So all the investors that werepaying attention to my monthly
updates knew exactly what wasgoing on, felt like we were
making all the right moves.
You know it was either monetize, sell it or raise money.
Those are the three options,you know.
And nope, nope and nope,unfortunately.
(17:51):
So everyone was kind of eyeswide open in the know when we
got to that place and you know Iwould say we had dozens of
contemporaries.
Like a lot of people were kindof smelling that same signal
that I was when the pandemic hit.
You know that communication isgoing to change and async video
is a solution, so that we haddozens of other companies that
(18:14):
were kind of competitors orcopycats or whatever you want to
say, and we did better than anyof them, which I'm proud to say
, but just not good enough notescape velocity.
We never reached escapevelocity and, given the
trajectory, I just couldn't seeit happening Like if we had six
more months or 12 more months.
We needed years, not monthsmore.
Speaker 2 (18:37):
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
(19:00):
and HR, and these are peoplewho've experienced a lot.
They've been in the trenches,they've built businesses,
they've failed.
But here's the kicker They'velearned from those failures and
now they're applying all thatwisdom to your business to
support you.
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
hit the wall, you could bringsomeone in who's already mapped
(19:23):
out that room dark and hopingyou don't hit the wall.
You could bring someone inwho's already mapped out that
room right.
Amplio consultants and expertshave worked with and for
numerous companies of all sizesand they've gathered insights on
what works and where to focusand how to actually grow your
business efficiently.
So, while we embrace failure onthis podcast, there is no rule
that says you have to fail ateverything yourself.
So check out Amplio and see howtheir fractional executives can
(19:46):
help your business move forwardand avoid those painful
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Sometimes the smartest move islearning from someone else's
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Visit Ampliocom to learn more.
What was the toughestconversation you had as you shut
down something you had beenbuilding and were excited about
and had an interesting productgreat investor group trajectory
at one point.
Speaker 1 (20:08):
Well, I mean that's why I say investors who were
paying attention, because therewere a couple of investors that
just weren't paying attentionand they didn't know all of the
things that we did, didn't careto understand the full story and
they felt like we just gave up,right, and so those
conversations were hard to oneinvestor, like try to rip me up
on LinkedIn and like if you onlyknew, if you only knew.
(20:32):
But you know, 98% of investorssaid things like you guys ran a
flawless performance, like yourexecution was near flawless.
And I really feel like.
I feel like I did the best workof my life.
I built the best product I'veever built in my life.
Um, and I you know, I hang myhead pretty high based on the
(20:52):
work that we did Didn't see thescore on the scoreboard like
we'd like to see, but lookingback, it's hard to find like
obvious gaps or holes or baddecisions that we I'm not saying
there weren't hindsight.
Well, that's what I want totalk about, cause it's hard to
find like obvious gaps or holesor bad decisions.
I'm not saying there weren't.
Speaker 2 (21:06):
Hindsight's easy.
Well, that's what I want totalk about, because it's easy to
attribute our failures tocircumstances or economy or
capital constraints, competitivedynamics that are outside of
our control.
But, like for entrepreneursthat are listening, what are the
things inside of your controlthat you would have done
differently?
What are some of the keylearnings your control that you
would have done differently?
What are some of the the keylearnings, some things you won't
(21:28):
do again.
Speaker 1 (21:30):
Yeah, I think I probably this is easy in
hindsight in in unfortunately.
I do feel like, given the data Ihad, I'd probably do the exact
stinking same thing, you know,if I had the same data moving
forward.
But we should have.
We should have pivoted a littleearlier from the team thing,
but that's what everyoneinvested in, that's what
(21:51):
everyone thought like.
This is the time for thisproduct.
We just had to get it right,you know.
So we didn't want to move awayfrom that too fast.
And another thing in this I canargue both sides of this.
Another thing we probablyshould have done was monetize
from day one.
Um, but that's not themessaging playbook and um, uh,
(22:12):
and while that would have helpedus orient on a willingness to
pay, like a user that's willingto pay and build around them, it
may not have helped us find,ultimately, what I think would
have been successful with iswhich is that consulting,
coaching, you know, monetizingexperiences you're creating on
Volley, that product.
Because I think if we monetizedfrom day one, we would have
(22:35):
monetized something very similarto what Slack and other team
communications products aredoing and we would have found a
handful of people that werewilling to pay.
Like I said, it wasn't a zerothat you um, and we would have
just oriented around them andnever looked further.
So we probably should havemonetized earlier, but I could
also see where that would havegot us stuck in the mud earlier.
Speaker 2 (22:58):
For sure, tell me about the like.
We sometimes ignore thepersonal cost of building
something and it failing.
Speaker 1 (23:05):
Yeah.
Speaker 2 (23:06):
How did you deal with this kind of emotionally?
What was your kind of reactionin the quiet moments where
you're sitting playing guitar orsinging.
Speaker 1 (23:13):
I know you're a musician.
Speaker 2 (23:15):
How are you feeling?
Speaker 1 (23:17):
Oh yeah, just demoralized, humbled, all the
words, like confused, cause it'snot like I wasn't doing
something that I knew I shouldbe doing, like I was doing
everything that I could possiblythink of, and so was the rest
of the team, and and when you'rein a situation like that and
and you're just not seeing, youknow you're just not seeing it
(23:41):
work, it's, it's reallyfrustrating, you know you're
just not seeing it work, it'sreally frustrating.
And you know how did I dealwith it?
Food, food's a, it's a goodmedicine, like it's effective,
it works.
Speaker 2 (23:53):
So I gained like 50 pounds.
50 pounds, yeah, I put on 50pounds.
Yeah what?
Speaker 1 (23:57):
was your food of choice?
Oh, nachos, nachos, right, it'sthe most delicious thing you
can put together on the earth.
No, I don't know.
How are your sleeping patterns?
Sleep is good.
Yeah, I've always slept.
Good.
Speaker 2 (24:12):
So not a problem, Talk to me about your family
relationships some of your maybeco-founder relationships.
What was the on any type ofpersonal relationship that you
had?
Speaker 1 (24:23):
Yeah, you know, other than the couple of investors
that weren't quite payingattention, I I feel like they're
stronger, stronger, like Ithink most investors that were
in volley would probably bet onme again, as crazy as that
sounds that you know, if I had anew idea this month and was
going to pull the team togetherjust based on how we executed
(24:46):
like it was, it was a.
We played a really good game.
I'm proud of that.
But, uh, you know, it's alwayshard to not return somebody's
money.
Um, you know, at a minimum Iwant to be able to return their
money, right, um, uh, but Ican't imagine a situation where
we hadn't and and family.
You know, my wife and kids know,they know the game we're
(25:09):
playing and you know, if you'regoing to ride a horse, you're
going to fall off Like there's.
There's no way around it.
And if you ride a horse, aslong as I have, you know, you're
going to get some bumps andbruises, and I've had them
before.
So this is just another one ofthem.
Unfortunately, brews, and I'vehad them before, so this was
just another one of them,unfortunately.
Speaker 2 (25:31):
Yeah, that was my experience too when I drove once
from St George to Ogden in oneday and I started early in the
morning and I just met with abunch of the local investors
that I had raised money fromsome family offices, some of the
angels- that you probably knowwell and I remember sitting at a
coffee shop up in Ogden right,and I was actually pretty
distraught.
Speaker 1 (25:44):
Yeah.
Speaker 2 (25:44):
I'd lost more than 6 million bucks, um, but this
particular investor hadsupported me in a couple of
different ventures and I satthere and I was a little
emotional and I just apologized.
I said it's gone Like there'sthere's no way to recoup the
equity.
I've lost all of yourinvestment.
And it was um.
It was extraordinary to see hisresponse to that.
(26:06):
He asked how are you doing?
How's?
your family, and he looked at meand said essentially what some
of your investors said, whichwas, if you came to me today
asking me to invest in you again, I would do it.
I was prepared for eitheroutcome here, and that, to me,
was maybe the most profoundconversation I've ever had with
an investor, more than investorsapplauding you when you're
(26:28):
succeeding to have an investorsupport you when you've failed
is really heartwarming anduplifting and encouraging.
It may be the single mostconfidence building comment
anyone has ever told me, becauseit's in the face of like me
losing.
I probably lost a milliondollars of his money.
Right, he was one of.
He wasn't our largest investor,but he was someone I had a
(26:50):
personal relationship with andthat was incredibly painful and
it sounds like you had some ofthose experiences as well.
Speaker 1 (26:55):
I had a lot of those conversations.
Yeah, one in particular JacobMullins of Shasta Ventures,
which is a VC firm in the BayArea.
They put a million and he wasprobably more ready to shut
Volley down.
Not probably he was more readyto shut Volley down than I was,
period, just because he had sawhow hard we had worked.
(27:16):
And if you work that hard atsomething it'll go.
And if it's not going, you justdon't have product market fit,
it's not the right time, or it'snot the right time or not the
right product or whatever.
Um, and you know, in a lot ofthe conversations he would, yeah
, ask about me and and everytime he'd be like, okay, what
are you guys doing next?
Like we'll back it, like let'sbuild something else.
(27:37):
And I was like, oh man, that'sawesome for you to say, but I'm
pretty tired and I'm going totake a nap so I want to take a
couple of weeks or months ofnaps.
So not sure that I'm ready totake another bite yet or another
swing.
Speaker 2 (27:50):
Yeah, that's certainly how I felt after my
last venture, as I startedplaying guitar again after 20
years and skied a lot and justhad to breathe because, of that
intensity.
I mean, like when you're tryingto solve a puzzle, it feels
kind of impossible.
You're trying everything right,you're modifying the product,
You're throwing features at theproduct, you're talking to
customers You're working onpartnerships, right, you're
(28:12):
looking for an acquisition, astrategic investor like, and
you're just like tryingeverything and anything right To
get this to go and it's notgoing.
It's emotionally exhausting.
Speaker 1 (28:22):
Yeah, it's mentally taxing.
Speaker 2 (28:24):
It's humbling.
Yeah, for sure, for sure.
Do you think the outcome wouldhave been different if you would
have had more capital?
Speaker 1 (28:30):
Because it's easy to blame.
Speaker 2 (28:31):
I've always thought oh well, if I had more capital,
like I could have like pushedthrough and figured out the
right product, market fit,figured out the right customer,
built the feature set mycustomers wanted.
Speaker 1 (29:08):
Yes.
Speaker 2 (29:08):
If we had more.
Speaker 1 (29:09):
Let me try to unpack that I that gives us the benefit
of time and space.
That lets you say what you needto say, move on with your day,
have a meaningful conversationwhen you come back to it and
listen to others on 2X and youcan speak seven times faster
than like all of the thingsabout async video, I can't
believe that a global pandemicdidn't change people's sentiment
there.
(29:29):
I can't believe it.
But at the same time I don'tknow what's coming down the road
that's going to change people'ssentiment.
It could be Elon tweetssomething.
It could be some global, Idon't know some other product,
but I do know the TikTok andSnapchat generation are a lot
more comfortable with asyncvideo than than um existing
(29:52):
generations that are in chargein the workforce.
Right, my kids are all about itall day, every day all day,
every day.
My kids don't even type anythingin Google, they just talk to
Google and we're Siri, right, soI see a future generation that,
um, that would so if we, if wehad enough capital to last long
enough, we would have figured itout, and a lot of people feel
like we did figure it out rightat the end with the consulting
(30:15):
piece allowing asynchronousmicro-consulting.
You know, there's nothing thatdoes that, and there are things
like intro that lets you booktime with an expert but, that's
another synchronous meeting.
What expert wants anothermeeting on their calendar, right
?
Wouldn't you just love amessage from somebody that had a
question for you that you couldlike get to on your walk?
And that's exactly what weoffered.
But we only had three months torun after that and we saw that
(30:39):
inflection point at the end andthen we're like we got to shut
it down because it was only like5k in monthly revenue that
we're getting Even more painful.
Speaker 2 (30:46):
right, it's because you're like, ah, we had it.
Speaker 1 (30:49):
We had it right there .
Speaker 2 (30:55):
So tell me about the word failure.
We don't use it.
I mean, we probably have onlysaid it a few times in this
whole conversation.
I understand like, asentrepreneurs, we try to frame
failure in ways that maybeprotect ourselves from
acknowledging our owndeficiencies or decision making.
Do you feel like Volley was afailure?
Speaker 1 (31:06):
It depends on what question you're asking.
I failed to return capital tomy investors.
So, yes, I failed at doing that.
I didn't fail at building agreat product, building a killer
team, engaging our users,building a product that some
people loved.
I didn't fail at executing aswell as anyone could at that
(31:30):
venture.
So I didn't fail at thosethings.
We just failed getting theproduct to reach the measure of
its creation.
You kind of like you said it'strue potential.
We failed at figuring out theexact right mix for the right
people at the right time to getit there and ultimately, how
does this failure change yourperspective of entrepreneurship,
(31:52):
or has it?
Speaker 2 (31:53):
I mean, is it going to change the way you build your
next business?
I know that you're stillworking on Volley right it
sounds like there's still afuture.
So the Volley story hasn't beenit's not fully over.
Speaker 1 (32:04):
I've acquired it.
We've rebuilt it and relaunchedit.
It's just a product that needsto exist.
It's too dang good to see itjust go in the trash.
So I don't know if it's a greatfinancial move, but it's a
labor of love and it also thestory's not over, so I get to
save that right.
We'll just see what happens.
And our plan is just let Volleygrow organically over time.
(32:26):
And it grows, you know 5% to10% a week and you know those
gains stack up over timeorganically.
People invite other people insome stick some stone.
We'll keep bugs fixed, buildsome new features and we'll see
where it goes.
But it's it's not a full-timeeffort for anyone on the team at
this point.
Um, labor of love, but how hasit changed me?
(32:47):
I think you'd have to be apsychopath just to like not be
phased at all by by anexperience like this.
Um, because a lot of the peopleI raised money from were my
friends, close friends, um, andmany have become friends now,
right, and so I raised a bunchof money for my friends that I
(33:08):
wasn't able to return, um, andthat that hurts, you know, and
it makes me a little gun shy, itmakes me worried about
potentially doing that again.
And do I really have it?
And ask, ask some of thosefoundational questions.
But I, I came from ruralMichigan where I worked in
restaurants and I was a highschool teacher, you know, and,
(33:29):
and I've made my way through allthe twists and changes to be an
entrepreneur, you know, and,and I've made my way through all
the twists and changes to be anentrepreneur, to be a tech
entrepreneur, I, I, I dosomething where people will give
me millions of dollars to buildmy dream willingly, and you
can't, you can't think thatthat's not a privilege, you know
.
So it's an absolute privilege todo what I do.
(33:50):
Um, it is confidence shaking tohave a failure, but, um, but
I'm honored to do what I do andI feel like if, if I don't do it
, it's not filling the measureof my creation.
Uh, doing what I potentiallycould do, like being a tech
entrepreneur, is the highestpaid potential career in the
world right, if you get it right.
You know, like the richestfolks on earth did what I do and
(34:13):
and I'm good enough to thinkthat I, I could do that if I, if
I got the right product in theright time, the right team and
um, just got to find that soyou're gonna get back on the
horse get back on the horse.
Maybe not this week but, uh,maybe this year we'll see.
I've got seven ideas that I'mkind of playing around with.
Speaker 2 (34:29):
Yeah, thank you for your candor about just the
personal costs, the emotionaltoll it takes, Certainly the
pain of raising money frompeople that we care about, our
friends and investors, and notbeing able to return that money.
Like that's, I think, the storythat we often overlook when we
glorify the successes right.
(34:50):
And we see the entrepreneursthat take companies public and
sell for hundreds of millions ofdollars.
It's easy to focus on that, andreally the outcome that you
experienced happens most of thetime, but we rarely talk about
those outcomes, and then that'swhere I think the richest
lessons and learning are inthose, and so you've shared your
insight in a way that I justreally appreciate, josh, and if
(35:10):
you came to me and you wereraising money, I would bet on
you too, because I feel likethat the accumulation of those
experiences actually de-risksthe journey for you and for your
investors moving forward.
Speaker 1 (35:24):
I really think so.
I really feel like my best workis ahead.
I feel like Volley was the bestwork of my life.
Didn't show on the scoreboard,but all of those lessons and
learnings are paid forward tothe next thing right um, and and
so I'm excited about it.
Speaker 2 (35:38):
Not sure what that is , but I'm excited about whatever
that is yeah, I always havethis like vision in my mind of
like, um, you know, if I, if Iever hit the grand slam, right,
I'm going back and driving fromsaint george to ogden again and
just like handing checks out andjust saying thank you so much
for believing in me.
That one didn't turn out butthis one did, and it was really
on the back of those investorsand those experiences and that
(36:03):
capital that they entrusted mewith, that I was able to get to
an outcome, a really positivefinancial outcome.
Speaker 1 (36:10):
So, anyway, now that's public, so I guess all my
investors will be like I'll bewaiting at the cafe for the
check.
Here we go, joe.
Yeah, where is it at man?
That's right.
Thank you so much, josh, ofcourse.
Yeah, thanks for having me.
I'm Josh Little and I failedwhile daring greatly.
Speaker 2 (36:24):
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.
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